"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech

E67: Navigating the Era of "AI Slop" in Accounting with Luke Frye

Wed, 01 Apr 2026 07:00:00 -0000

In this episode, Sasha Orloff sits down with Luke Frye, founder of LukeFrye.co, to trace his decade-long journey through foundational fintech pioneers like Bench and Pilot and explore how AI is shifting the accountant's role from manual data entry to "architecting" financial systems and human-centric advisory.

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Puzzle

📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/lukefrye/

https://lukefrye.co/

X/SOCIAL:

@LukeFrye (Luke)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:37) Intro

(02:14) From Wyoming To Techstars

(05:49) Bench origin story

(07:11) Automating accounting tension

(09:20) Bench growth playbook

(11:06) Early sales and scale

(14:28) Sponsors: Notion | Puzzle

(15:53) Bench cracks and incentives

(18:59) Tax experiment trainwreck

(21:38) Solo practice to Pilot

(23:51) Pilot tech stack shift

(24:48) Sales ops balance

(26:36) From Pilot to Rivet

(27:18) Why Puzzle mattered

(29:17) Modern tax software gap

(31:12) Automation limits today

(34:33) AI makes us human

(37:06) Where firms should start

(39:19) Vision values planning

(42:43) Future firm architect

(44:57) Wrap

E66: Engineering the Modern Accounting Firm with Greg Capitolo of Attivo Partners

Tue, 24 Mar 2026 07:00:00 -0000

In this episode, Sasha Orloff speaks with Greg Capitolo, Co-founder and Partner at Attivo Partner, to discuss how fractional finance teams are transitioning from manual bookkeeping to AI-driven advisory roles, emphasizing the shift toward "real-time data-driven decision making" over traditional month-end closes.

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Puzzle

📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/gregcapitolo/

http://www.attivopartners.com

X/SOCIAL:

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:39) Intro

(02:07) Meet Greg Capitolo of Attivo Partner

(03:26) Who Attivo serves

(04:07) Why VCs recommend

(06:40) Founder trigger points

(08:50) AI outlook

(10:59) AI boosts advisory

(15:19) Creating 10x accountants

(19:51) Sponsors: Notion | Puzzle

(21:14) Pricing and billing shift

(23:41) Choosing AI tools

(27:06) Human in the loop

(30:22) Accounting needs accountants

(32:09) Real time data

(35:14) Tool evaluation framework

(38:54) Growth mindset future

(40:56) Wrap

E65: a16z-backed Stuut CEO Tarek Alaruri on Why Legacy AR Software Failed and How AI Fixes It

Wed, 14 Jan 2026 08:00:00 -0000

In this episode, Sasha Orloff speaks with Tarek Alaruri, CEO and Co-founder of Stuut, about raising a Series A from Andreessen Horowitz to build an AI-powered accounts receivable platform that automates the entire AR function—from credit and collections to cash application and disputes—delivering a 40% reduction in DSO in the first six months compared to the 3% improvement from legacy software, while implementing in just 3.6 days for mid-market and Fortune 100 companies.

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Puzzle

📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/tarekalaruri/

https://www.stuut.ai/

X/SOCIAL:

@TAlaruri (Tarek)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:42) Intro

(01:25) Interview with Tarek Alaruri, CEO of Stuut

(01:50) Problem with traditional accounts receivable

(03:31) How AI is transforming accounts receivable

(05:39) Stuut's mission and impact

(08:17) Future of AI in finance

(09:55) Customer experience and AI solutions

(11:35) Evolution of AI and business processes

(14:04) Sponsors: Notion | Puzzle

(15:31) Eliminating clicks with Stuut

(17:07) AI in B2B transactions

(21:56) Role of AR teams today and tomorrow

(23:38) Fundraising insights and strategies

(30:46) Building enterprise AI and future outlook

(35:12) Wrap

E64: Numeral CEO Sam Ross: Why I Abandoned My Profitable Business to Raise $50M for Something "Boring"

Wed, 07 Jan 2026 09:00:00 -0000

In this episode, Sasha Orloff sits down with Sam Ross, co-founder and CEO of Numeral and former product leader at Teespring and Airbnb, about raising Series B funding from Mayfield (following Benchmark's Series A and Uncork's seed) to build what he calls "the most boring AI company"—an end-to-end sales tax automation platform that uses AI to eliminate the manual burden of multi-state and international tax compliance for e-commerce and SaaS businesses, transforming a traditionally services-heavy industry into a fully automated solution that handles everything from nexus analysis and registration to filings and government correspondence.

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Puzzle

📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/sambross/

https://www.numeral.com

X/SOCIAL:

@SpamRoss (Sam)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:49) Intro

(01:22) Guest Introduction: Sam Ross

(01:44) Most boring AI company

(03:54) AI and sales tax

(06:08) Origin story and early challenges

(10:56) Building the business and first customers

(13:14) Sponsors: Notion | Puzzle

(14:36) Sales tax compliance and solutions

(17:12) Automating mail and customer engagement

(18:24) E-commerce and tax compliance challenges

(19:40) Marketplace tax exposure issues

(22:15) Government complexities and physical mail

(23:54) Founding story and funding journey

(30:55) AI innovations in tax compliance

(33:11) Future of AI and browser automation

(34:33) Wrap

E63: Reverse Engineering Venture Capital with Metal's Usman Gul

Wed, 17 Dec 2025 08:30:00 -0000

In this episode, Sasha Orloff speaks with Usman Gul, founder and CEO of Metal, about building an AI-driven operating system for fundraising backed by Y Combinator and Andreessen Horowitz that helps founders avoid wasting 80% of their investor meetings by using data-driven insights to identify the most likely investors based on historical funding patterns, industry benchmarks, and relationship intelligence across over 500,000 venture rounds.

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Puzzle

📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/gulsf/

http://www.metal.so

X/SOCIAL:

@usmangul (Usman)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:44) Intro

(01:28) Meet Usman Gul from Metal

(01:59) Genesis of Metal

(04:32) Metal's AI-driven fundraising solutions

(08:08) Common fundraising mistakes and solutions

(13:24) Sponsors: Notion | Puzzle

(14:15) Importance of modern tools for startups

(21:40) Metal manifesto

(24:35) Key indicators for successful fundraising

(25:53) Telling the right story to investors

(26:44) Challenges and insights from previous ventures

(27:13) Evolution of investor targeting

(28:38) Predictive intelligence and the future of Metal

(30:41) Current state of fundraising tools

(36:53) Building Metal with minimal capital

(39:19) Advice for founders on fundraising

(47:29) Wrap

E62: From Divvy FP&A to Parallel Founder: How Renato Villanueva Built the Tool Finance Actually Wants

Wed, 10 Dec 2025 08:30:00 -0000

In this episode, Sasha Orloff speaks with Renato Villanueva, Founder and CEO of Parallel, about his journey from finance professional at Divvy to raising $2.4 million from Bain Capital and K5 Tokyo Black for an AI-powered FP&A platform that helps founders model financial scenarios and make confident growth decisions. Renato shares lessons on building products founders are passionate about rather than forced wedges, nurturing investor relationships, and how Parallel's approach has enabled customers to achieve significant growth—including one company that scaled from planning one sales hire to four, ultimately raising one of Utah's biggest Series A rounds.

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Puzzle

📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

RECOMMENDED IN THIS EPISODE:

⁠https://www.linkedin.com/in/villanuevar/⁠

https://www.getparallel.com/

X/SOCIAL:

@_renatov (Renato)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(01:24) Intro

(02:09) Meet Renado Villanueva

(02:38) Renado's journey to founding Parallel

(04:02) Moment of decision

(04:45) Building the deck and quitting the job

(09:20) Challenges and insights in fundraising

(11:05) What Parallel actually does

(14:24) Sponsors: Notion | Puzzle

(15:49) Parallel’s target sweet spot

(16:49) Common mistakes founders make

(19:30) AI's role in finance decision-making

(20:15) Balancing flexibility and opinion in software

(23:11) Who should use Parallel?

(25:06) Excel vs. Parallel: Finding the right balance

(27:06) Evolution of FP&A tools

(31:24) Lessons learned from building Parallel

(35:34) Building and trusting a team

(38:31) Future of Parallel

(39:47) Wrap

E61: Maxima's $41M Mission: Automating Enterprise Accounting Close with AI

Wed, 03 Dec 2025 08:00:00 -0000

In this episode, Sasha Orloff talks with Yogi Goel, Co-founder and CEO of Maxima, about raising $41 million from Kleiner Perkins and RedPoint Ventures to build an agentic AI platform for enterprise accounting that automates journal entries, reconciliations, and variance analysis for complex companies, helping them close their books 2-3 days faster with 98% automation while strengthening SOX controls and freeing accountants from mundane tasks.

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Puzzle

📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/yogi-goel/

https://www.maxima.ai/

X/SOCIAL:

@maxima_dot_ai (Maxima)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:50) Intro

(01:34) Introducing Yogi Goel and Maxima

(02:08) Problem with traditional accounting

(04:50) Birth of Maxima

(07:03) Maxima's solutions and innovations

(11:19) Sponsors: Notion | Puzzle

(12:43) Customer success stories

(25:08) Future of accounting with AI

(27:10) Fundraising and growth

(29:53) Advice for founders and CFOs

(34:15) Embracing AI: Overcoming fear and finding solutions

(35:56) Getting in touch with Maxima

(36:17) Story behind the name 'Maxima'

(37:01) Wrap

E60: Deel's COO on Scaling to $17.3B Valuation (and Where They Go From Here)

Thu, 20 Nov 2025 07:45:00 -0000

In this episode, Sasha Orloff sits down with Dan Westgarth, COO of Deel, to explore how the company scaled to 37,000 customers, processes $22B in payroll, and recently raised a $300M Series E to power global hiring in 150 countries. They dive into the future of back-office automation, including real-time payroll, AI-driven operations, and the push toward a unified, seamless global HR and accounting stack.

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Puzzle

📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/dan-westgarth-710650a4/

https://www.deel.com/

X/SOCIAL:

@DanWestgarth (Dan)

@deel (Deel)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:44) Introduction to Tech Finance

(01:25) Meet Dan Westgarth, COO of Deel

(02:18) Dan's journey with Revolut

(06:22) Building Deel's global infrastructure

(08:33) Managing global operations

(12:06) Expanding Deel's services

(19:56) Importance of consolidation

(21:15) Sponsors: Notion | Puzzle

(22:55) Common mistakes startups make

(24:09) Onboarding and implementation challenges

(25:46) Customer engagement and feedback

(28:23) Recruiting and hiring strategies

(31:27) Future of accounting and payroll

(40:53) Real-time payroll processing

(44:09) Wrap

E59: Why AI Tax Tools Fail the QSBS Test, with Nick Abouzeid of Rivet

Wed, 12 Nov 2025 08:00:00 -0000

In this episode, Sasha Orloff talks with Nick Abouzeid, Co-founder and CEO of Rivet, about raising venture capital from XYZ, Haystack, and other angels to build a modern tax and accounting firm that serves 600+ category-defining companies like Cursor by combining world-class tax practitioners with custom-built software infrastructure, delivering premium responsive service while challenging the traditional accounting firm model of unresponsive service and outdated technology.

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Puzzle

📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

RECOMMENDED IN THIS EPISODE:

https://www.rivet.tax

https://www.linkedin.com/in/nickabouzeid/

X/SOCIAL:

@nickabouzeid (Nick)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:36) Intro

(01:21) Meet Nick Abouzeid, CEO of Rivet

(01:57) Rivet unique approach to tax services

(02:52) Challenges in the tax preparation market

(06:59) Human element in AI-powered tax services

(09:33) Journey to venture capital

(14:29) Sponsors: Notion | Puzzle

(15:54) Scaling and surprises in building Rivet

(18:23) Open roles and team dynamics

(19:00) Feedback and roadmap development

(19:24) International hiring and cost efficiency

(20:40) Data integration challenges

(21:23) Future of AI in accounting

(22:58) Complexity in tax code and software

(23:30) Human expertise vs. AI

(32:23) Pricing models in tax preparation

(34:26) Client success stories

(36:29) Looking forward: New hires and future plans

(37:16) Wrap

E58: The future of M&A is AI? With Blake Hutchison, CEO of Flippa

Fri, 24 Oct 2025 09:00:00 -0000

In this episode, Sasha Orloff sits down with Blake Hutchison, CEO of Flippa, to discuss the launch of Lauren AI—Flippa’s new AI tool transforming how online businesses are bought and sold. They explore how Lauren AI uses proprietary data and machine learning to enhance deal sourcing, automate buyer outreach, and streamline deal structuring. The conversation also dives into how AI is reshaping small business M&A, making exits and acquisitions more accessible, efficient, and competitive for entrepreneurs worldwide.

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Puzzle

📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

RECOMMENDED IN THIS EPISODE:

https://flippa.com/product/dealsourcing/

https://www.linkedin.com/in/blakehutchison

X/SOCIAL:

@Flippa (Flippa)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:32) Intro

(01:01) Interview with Blake Hutchison, CEO of Flippa

(01:45) Introducing Lauren AI

(02:15) How Lauren AI Enhances deal sourcing

(07:05) Real-life example of Lauren AI in action

(13:08) Sponsors: Notion | Puzzle

(14:35) Matching engine and AI capabilities

(17:38) Buyer experience and mandate creation

(19:21) Lauren AI: Enhancing buyer profiles

(21:33) Outreach and CRM integration

(23:59) AI's role in M&A processes

(28:33) Leveling the playing field for small buyers

(31:11) Fair pricing and exit readiness

(37:04) Wrap

E57: Lessons from Brex, SVB, a16z: How Jason Mok Spots What Founders Need Before They Know It

Thu, 25 Sep 2025 07:00:00 -0000

In this episode, Sasha Orloff sits down with Jason Mok, VP & GM of Startups at Brex, about the company's evolution from credit cards to a comprehensive financial platform and their new partnership with Puzzle to offer "one-click accounting" that automatically sets up bookkeeping for startups during Brex onboarding, eliminating the friction that typically delays founders from getting proper financial infrastructure in place from day one.

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Puzzle

📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/jasonmok/

https://www.brex.com/

X/SOCIAL:

@jasonmok (Jason)

@brexHQ (Brex)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:50) Intro

(01:18) Live from Brex offices with Jason Mock

(02:19) Early days of Brex and startup credit challenges

(04:20) Silicon Valley bank's role in the startup ecosystem

(12:26) From SVB to Andreessen Horowitz

(18:50) Sponsors: Notion | Puzzle

(20:13) Bridging the knowledge gap for first-time founders

(22:48) Joining Brex during a time of change

(28:02) Starting at Brex: Initial goals and challenges

(28:52) Evolving role and team growth

(29:39) Bespoke go-to-market strategies

(32:08) Defining startups at Brex

(36:54) Importance of accounting for startups

(42:25) Introducing one-click accounting

(46:52) Partnerships and future vision

(55:13) Wrap

E56: 5,000 Startups Later: Tax Lessons Every Founder Needs with Joe Faris

Wed, 17 Sep 2025 08:45:00 -0000

In this episode, Sasha Orloff talks with Joe Faris, founder of Accountalent, about his four decades of helping over 5,000 startups navigate tax and accounting challenges, covering critical founder lessons from 83B elections and R&D tax credits to payroll compliance and bookkeeping best practices that can save startups from costly mistakes and penalties.

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Puzzle

📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/farisjoe/

https://accountalent.com/

X/SOCIAL:

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:55) Intro

(01:24) Meet Joe Ferris: Startup tax expert

(03:24) Joe's journey: From Shell oil to startups

(06:46) Birth of Accountalent

(09:14) Navigating the financial crisis

(13:32) Adventures in IPOs and legal battles

(19:33) Sponsors: Notion | Puzzle

(21:18) Lessons for founders: Payroll pitfalls

(23:21) Introduction to payroll medic

(23:39) Understanding tax compliance for startups

(26:37) Importance of bookkeeping

(27:55) Unbook keeper for founders

(29:08) Setting up and managing bookkeeping systems

(35:44) Role of RD tax credits

(38:32) Lessons learned from working with startups

(39:51) Impact of good accounting and tax strategy

(42:29) Wrap

E55: First Round and YC-Backed Startup 'Eliminating Business Bullshit' | Josh Wymer, CEO of CentralHQ

Fri, 05 Sep 2025 09:00:00 -0000

In this episode, Sasha Orloff talks with Josh Wymer, Co-founder and CEO of Central HQ, about raising $8.6 million from First Round Capital and Y Combinator to build an AI-first back office solution that eliminates business compliance tasks through Slack-based automation, helping startups handle payroll, taxes, and HR without the administrative burden that typically comes with traditional software.

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Puzzle

📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

RECOMMENDED IN THIS EPISODE:

⁠⁠https://www.linkedin.com/in/joshwymer/

https://centralhq.com/

X/SOCIAL:

@jbwyme (Josh)

@CentralHQX (Central HQ)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(01:03) Intro

(01:46) The unavoidable hassles

(02:20) Meet Josh Wymer: The mission to eliminate business BS

(02:57) Complexity of payroll and compliance

(04:48) Central’s vision: Simplifying the back office

(07:19) Challenges and innovations in payroll solutions

(10:10) Sponsors: Notion | Puzzle

(11:35) Future of AI in business operations

(18:42) Power of LLMs and AI in streamlining tasks

(21:42) Origin of the tagline

(23:41) Investor reactions and brand strategy

(24:36) Challenges in a competitive market

(25:32) Focusing on founders and SMBs

(28:51) Learning and iterating as a startup

(33:21) Misunderstandings and common mistakes

(36:44) Future of startups and SMBs

(38:42) Wrap

E54: Filling the Gap Between QuickBooks and NetSuite with SoftLedger CEO Ben Taylor

Wed, 27 Aug 2025 08:30:00 -0000

In this episode, Sasha Orloff talks with Ben Taylor, CEO & Co-founder of SoftLedger, about bootstrapping a modern, API-first general ledger that helps finance teams manage multi-entity businesses beyond QuickBooks without the complexity of Netsuite.

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Puzzle

RECOMMENDED IN THIS EPISODE:

⁠https://www.linkedin.com/in/bentaylor8/

⁠https://softledger.com

X/SOCIAL:

@SoftLedger (SoftLedger)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:40) Intro

(01:09) Meet Ben Taylor, CEO & Co-founder of SoftLedger

(02:36) Origin story of SoftLedger

(03:11) Target market and unique selling points

(07:14) Evolution of the accounting software market

(08:21) AI in accounting: Opportunities and challenges

(11:08) Sponsors: Notion | Puzzle

(12:31) SoftLedger's approach to AI integration

(17:34) Choosing the right accounting software for complex enterprises

(19:16) Customer success stories: Eco G energy

(22:31) Challenges and surprises in building accounting software

(26:58) Importance of multi-entity consolidation

(31:53) Fundraising journey and efficient growth

(34:16) Future plans and market expansion

(37:03) Wrap

E53: How AI Agents are Replacing Manual Accounting Work with Truewind CEO Alex Lee

Wed, 06 Aug 2025 07:00:00 -0000

In this episode, Sasha Orloff and Alex Lee, Co-founder & CEO of Truewind, to discuss how his company is transforming accounting with AI-powered automation—streamlining tasks like data reconciliation and deposit matching from hours to minutes. They explore Truewind’s journey, recent funding led by Thomson Reuters and Row Capital, and the future of accounting through AI, autonomous agents, and customer-centric innovation.

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠⁠⁠

Puzzle

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/alexlee611/

https://www.truewind.ai/

X/SOCIAL:

@AlexLee611 (Alex)

@truewindai (Truewind)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:28) Intro

(01:07) Guest Introduction: Alex Lee from Truewind

(02:27) Origin of Truewind

(06:18) Impact of AI on accounting

(08:24) Adoption of AI in accounting

(09:59) Future of finance and accounting teams

(12:09) Truewind's approach and strategy

(15:13) Role of automation in accounting

(17:12) Sponsors: Notion | Puzzle

(18:49) Digital staff accountant concept

(19:53) Exploring AI features in finance

(21:07) Government regulations and data sharing

(22:23) Exciting news: Fundraising success

(24:08) Customer-centric approach to product development

(24:57) Advice for founders on fundraising

(27:15) Defining success for Truewind

(35:55) Future of finance and AI integration

(37:08) Wrap

E52: Building a Viral Contract Platform: Will Hubbard, CEO of Agree

Wed, 30 Jul 2025 07:00:00 -0000

This week, Sasha Orloff sits down with Will Hubbard, Founder & COO of Agree, about building an all-in-one platform that streamlines contracting, invoicing, billing, and payments. They explore Agree’s rapid growth, recent $7.2M seed round, and how AI and user-centered design are shaping the future of finance tech.

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠⁠

Puzzle

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/wbhub/

https://agree.com/

X/SOCIAL:

@wbhub (Will)

@AgreeHQ (Agree)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:41) Intro

(01:23) Meet Will Hubbard: The story behind Agree

(02:19) Agree: All-in-one contracting and invoicing platform

(02:54) Evolution of Agree: From venture fund to B2B payments

(03:54) Delightful user experience of Agree

(06:06) Importance of design in accounting software

(06:57) The Why Now: Bundling contracting and invoicing

(08:51) Innovative features and AI-driven development

(13:38) Sponsors: Notion | Puzzle

(15:03) Favorite features: Tracking and reminders

(17:34) Surprising use cases and rapid development

(20:03) Viral growth of Agree.com

(21:22) Story behind Agree.com

(23:25) Challenges in naming a company

(24:57) Raising the next round of funding

(27:26) Future plans and product development

(29:11) Advice for finance leaders and founders

(34:22) Future of finance: Humans plus software

(35:37) Wrap

E51: Ramp for Revenue: The Tabs Playbook for Faster Cash Flow with CEO Ali Hussain

Thu, 24 Jul 2025 08:05:00 -0000

In this episode, Sasha Orloff talks with Ali Hussain, CEO of Tabs, discuss how the company is using AI to modernize revenue and collections management, reduce DSO, and boost efficiency for finance teams. They discuss Ali’s journey from PhD dropout to fintech founder, Tabs’ $25M raise, and how the platform is reshaping B2B finance operations.

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠

Puzzle

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/ali-hussain786

https://tabs.inc/

X/SOCIAL:

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(01:04) Intro

(01:43) Meet Ali Hussain

(03:20) Vision behind Tabs

(07:41) Challenges and opportunities in finance automation

(11:06) Future of finance teams

(15:29) Sponsors: Notion | Puzzle

(16:53) Case study: Success with Statik

(19:09) Example of Tabs in action

(19:49) Future of AI in finance

(21:41) Agentic future and trust

(23:52) Building operational software

(27:32) Favorite features and lessons learned

(30:32) Venture capital and market opportunity

(34:05) Advice for founders

(36:58) Future plans and excitement

(41:41) Wrap

E50: Zuora CFO Todd McElhatton on Why 70% of Finance Stacks Hold Back Growth

Mon, 21 Jul 2025 08:00:00 -0000

This week, Sasha Orloff and Zuora CFO Todd McElhatton discuss the growing complexity of finance operations and the critical role of AI in modern accounting. They talk about the insights from the 'Modern Finance Leader' report, strategies for overcoming legacy systems, and practical advice for finance leaders navigating technological change.

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠

Puzzle

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/todd-mcelhatton-2140761/

https://www.zuora.com/resource/modern-finance-leader-report/_

X/SOCIAL:

@Zuora (Zuora)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:43) Intro

(01:11) Season 2 focus: Accounting and technology

(01:30) Insights from the Modern Finance Leader Report

(02:13) Interview with Todd McElhatton: Challenges in finance technology

(05:34) The modernization Catch 22

(09:08) AI and the future of finance

(13:46) Sponsors: Notion | Puzzle

(15:26) Practical advice for finance leaders

(16:53) Zuora's impact and client success

(19:20) Role of AI and automation

(21:13) Building a 'Yes' department

(23:27) Advice for new finance leaders

(25:46) Transforming existing finance teams

(30:14) Strategic investment in technology

(32:22) Evolving role of CFOs

(34:21) Joining Zuora and making an impact

(35:29) Client success and product value

(36:39) Wrap

E49: Why Accel Backed Campfire to Build the Modern GL, with John Glasgow, CEO

Wed, 16 Jul 2025 08:30:00 -0000

In this episode, Sasha Orloff talks with John Glasgow, CEO & CFO of Campfire, about building an AI-native ERP system that streamlines finance workflows through automation and faster month-end close. Fresh from raising $35 million, John shares insights on modernizing legacy systems, the challenges of building complex financial software, and why now is the right time to innovate in accounting tech.

SPONSORS:

Notion

Puzzle

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/johnglasgow

https://campfire.ai/

X/SOCIAL:

@john__glasgow (John)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:22) Intro

(01:00) Guest introduction: John Glasgow

(01:51) Journey of Campfire

(05:05) Challenges and innovations in accounting software

(06:47) Shift to modern GL and AI integration

(11:21) Sponsors: Notion | Puzzle

(13:29) Real-world impact and case studies

(19:11) Fundraising and future plans

(20:01) Partnering with John Lockett and Excel

(21:06) AI conference and bigger investments

(21:48) Challenges of a seed-backed business

(22:50) Advice for founders in big industries

(23:36) Product velocity and customer trust

(25:51) Future plans and milestones

(29:24) Origin of Campfire

(30:53) Message to finance leaders and founders

(34:05) Future of finance and AI

(36:13) Wrap

E48: Why Sequoia Invested $25M in Accounting Software with Rillet CEO Nicolas Kopp

Wed, 09 Jul 2025 08:00:00 -0000

This week, Sasha Orloff and Nicolas Kopp, CEO & Founder at Rillet, discuss how Rillet is transforming accounting by leveraging AI to streamline processes, improve efficiency, and build lean finance teams. They also talk about the company’s $25 million funding from Sequoia, the importance of clean data, and Rillet’s customer-focused approach.

SPONSORS:

Notion

Puzzle

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/nicolas-kopp/

https://www.rillet.com/

X/SOCIAL:

@nicckopp (Nicolas)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(01:00) Intro

(01:28) Meet Nicolas Kopp from Rillet

(02:23) Rillet's mission and market

(03:11) Founding story and challenges

(05:27) Building a modern GL

(11:27) Future of finance teams

(14:56) Real-world examples and success stories

(16:39) Sponsors: Notion | Puzzle

(18:03) AI-powered ERP

(21:28) Building a business with substance

(22:03) Investor perception and challenges

(22:46) Customer obsession and success

(24:31) Advice for founders

(27:49) The Sequoia effect

(30:47) Future milestones and product vision

(32:23) Customer feedback and obsession

(38:47) Wrap

E47: Agentic Commerce, Stablecoins, and Global Trends with Cindy Turner, CPO of Worldpay

Thu, 12 Jun 2025 07:00:00 -0000

This week, Sasha Orloff and Worldpay Chief Product Officer Cindy Turner explore the shifting digital payments landscape—from stablecoins and agentic tech to global trends in account-to-account payments, regional behaviors, regulatory influences, and innovations like buy now, pay later.

SPONSORS:

Notion

Puzzle

RECOMMENDED IN THIS EPISODE:

⁠https://www.linkedin.com/in/lucinda-turner/

⁠http://www.worldpay.com

X/SOCIAL:

@Worldpay_Global (Worldpay)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:58) Intro

(01:40) Meet Cindy Turner: Chief Product Officer of Worldpay

(02:08) Cindy Turner's career journey

(06:41) Global payments report

(10:01) Account-to-Account payments: A global perspective

(13:15) Sponsors: Notion | Puzzle

(14:55) Unlocking Open Banking

(17:10) E-commerce and digital payments trends

(20:33) Impact of surcharging in Australia

(21:56) Surcharging trends in the US

(23:23) Cash dominance in certain countries

(26:03) Rise of buy now, pay later

(29:39) Future of payments: Agentic commerce

(33:59) Stablecoins and the future of payments

(37:29) Optimizing payments for businesses

(38:50) Wrap

E46: Ex-Plaid CTO on Why Tax is the Ultimate AI Challenge, with Jean-Denis Greze

Wed, 21 May 2025 07:00:00 -0000

In this episode, Sasha Orloff talks with Jean-Denis Greze, Co-founder and CEO of Town, about building an AI-powered tax solution for SMBs, exploring the startup’s origin, the balance between automation and human expertise, strategic market targeting, funding insights, and the transformative potential of AI in tax preparation.

SPONSORS:

Notion

Puzzle

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/jeandenisgreze/

https://town.com/

X/SOCIAL:

@jgreze (Jean)

@TownTaxCo (Town)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:48) Intro

(01:20) Jean-Denis Greze: The origin story of Town

(02:10) Challenges and opportunities in business tax prep

(03:41) Role of AI in automating tax preparation

(05:50) Market dynamics and constraints in tax services

(15:49) Sponsors: Notion | Puzzle

(17:14) Unique needs of small businesses

(24:38) Future of AI in tax preparation

(26:12) Segmenting the small business market

(27:15) Building trust and scaling AI

(37:14) Exploring AI agents and their potential

(47:21) Fundraising and future plans

(50:57) Wrap

E45: Artisan: Stop Hiring Humans, with Jaspar Carmichael-Jack

Wed, 30 Apr 2025 07:00:00 -0000

This week, Sasha Orloff sits down with Jaspar Carmichael-Jack, Founder & CEO of Artisan, about how their AI employees like Ava are transforming sales and workflows by integrating software into cohesive ecosystems, highlighting breakthroughs in AI capabilities, the balance between automation and human input, and the future of work.

SPONSORS:

Notion

Puzzle

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/jaspar-carmichael-jack/

https://www.artisan.co/

X/SOCIAL:

@jasparcjack (Jaspar)

@GetArtisanAI (Artisan)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:38) Intro

(01:08) Jaspar Carmichael-Jack, Founder & CEO of Artisan

(02:53) Concept and evolution of Artisan

(04:09) Challenges and iterations in AI development

(05:09) Expanding Artisan's capabilities

(08:33) Future of AI in the workplace

(10:34) Sponsors: Notion | Puzzle

(11:58) From better data to smarter responses

(13:24) Funding and growth journey

(16:44) Balancing AI and human labor

(27:26) Fun and unusual use cases for AI

(28:45) Final thoughts and lessons learned

(31:09) Wrap

E44: From $2B to $80B: Wealthfront CFO Alan Imberman’s 10-Year Journey

Wed, 23 Apr 2025 07:00:00 -0000

In this episode, Sasha Orloff is joined Alan Imberman, CFO of Wealthfront, about how a client-first philosophy, transparent access, innovative products like S&P 500 Direct Indexing, and strategic use of machine learning have helped Wealthfront grow to $80 billion in assets and 1 million customers, while delivering lower fees, better rates, and sustainable wealth-building strategies.

SPONSORS:

Notion

Puzzle

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/alan-imberman-cfa-aab2371/

https://www.wealthfront.com/

X/SOCIAL:

@Wealthfront (Wealthfront)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:48) Intro

(01:16) Interview with Alan, CFO of Wealthfront

(01:54) Wealthfront's vision and growth

(03:24) Innovative financial products

(04:19) Profitability and business model

(06:03) New product launches and strategies

(15:18) Tax loss harvesting and direct indexing

(17:43) Sponsors: Notion | Puzzle

(19:23) Wealthfront’s tax strategy triumph

(23:13) Bond ladders explained

(28:11) Future of Wealthfront and AI in finance

(33:41) Advice for founders and finance leaders

(36:01) Wrap

E43: The CFO's Blockbuster vs Netflix Moment: AI Adoption with Wouter Born

Wed, 16 Apr 2025 07:00:00 -0000

This week, Sasha Orloff is joined by Wouter Born, a finance, AI influencer, and General Partner at Born Capital to discuss how AI is reshaping the CFO role and financial tech stack, drawing lessons from Netflix’s rise over Blockbuster, emphasizing innovation, practical AI adoption, and financial storytelling.

SPONSORS:

Notion

Puzzle

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/wouterborn/

https://cfooffice.io/

X/SOCIAL:

@wouter_born (Wouter)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:58) Intro

(01:26) Meet Wouter Born: From founder to AI influencer

(02:39) Wouter entrepreneurial journey

(05:30) Evolution of CFOs in the age of AI

(07:28) Practical AI Tips for CFOs and Founders

(13:01) Future tech stack for CFOs

(17:15) Sponsors: Notion | Puzzle

(18:40) Changing role of CFOs

(21:30) Importance of storytelling in finance

(23:32) Leveraging AI for financial storytelling

(25:54) Building financial tools with AI

(28:51) Future of CFO tech stack

(34:54) Practical advice for AI prompting

(38:39) Connecting with the community

(39:53) Wrap

E42: Can AI predict the next unicorn. Crunchbase says yes with 95% accuracy.

Wed, 09 Apr 2025 07:00:00 -0000

This week, Sasha Orloff sits down with Megh Gautam, Chief Product Officer of Crunchbase, to explore the company’s evolution into an AI-driven intelligence platform, discussing its 95% unicorn prediction accuracy, AI-powered user experiences, pricing challenges, and insights for founders, investors, and job seekers.

SPONSORS:

Notion

Puzzle

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/meghbartma/

https://www.crunchbase.com/

X/SOCIAL:

@crunchbase

@skyspeak (Megh)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:35) Intro

(01:03) Megh Gautam, Crunchbase's Chief Product Officer

(01:48) Megh’s journey to Crunchbase

(04:26) Transitioning Crunchbase to an AI company

(07:06) Crunchbase's AI and data insights

(09:45) User engagement and product development

(14:58) Sponsors: Notion | Puzzle

(16:22) Forbes article on Crunchbase's AI model

(24:58) Pricing strategies and user experience

(29:33) Future of AI in product management

(35:53) Conclusion and future collaboration

(38:27) Wrap

E41: Surprising Trends from Deel's Data with Ben Cohen

Wed, 02 Apr 2025 07:00:00 -0000

This week, Sasha Orloff sits down with Ben Cohen, Head of Data from Deel to discuss the company's 2025 Global Hiring Report, covering trends in Gen Z salaries, rising demand for finance roles, global workforce management challenges, domestic hiring shifts, employee termination rates, and the tools Deel provides to support global hires, with an emphasis on trust and asynchronous decision-making for productivity.

SPONSORS:

Notion

Puzzle

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/benjamin-cohen-0618308/

https://www.deel.com/

X/SOCIAL:

@deel

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:40) Intro

(01:51) Understanding Deal's global hiring report

(02:38) Insights on data utilization

(04:42) Collaboration and data storytelling

(08:23) Generational workforce trends

(08:41) Gen Z's impact on the workforce

(13:59) Sponsors: Notion | Puzzle

(15:39) Global hiring trends and challenges

(19:49) Introduction to global hiring trends

(20:28) Surprising rise of accountants

(22:52) Impact of AI on job market

(25:31) Employee terminations and market trends

(30:01) Tools and insights for global hiring

(33:06) Best practices for a global workforce

(36:33) Data analysis tools

(38:15) Wrap

E40: The $500 Domain That Became a Multi-Million Dollar AI Tax Assistant with Kash Ali of TaxGPT

Thu, 27 Mar 2025 07:00:00 -0000

This week, Sasha Orloff is joined by Kash Ali, Founder and CEO of TaxGPT, who shares how a personal tax issue led to the platform’s creation, its rapid growth after Greg Brockman’s GPT-4 demo, investor interest from Marc Cuban and Jason Calacanis, its shift from a consumer tool to a B2B AI assistant for accountants, its unique advantages over general AI, and his own journey from Pakistan to Silicon Valley, culminating in Y Combinator and a vision for the future of AI-driven tax assistance.

SPONSORS:

Notion

Puzzle

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/chkashifali/

https://www.taxgpt.com/

X/SOCIAL:

@AskTaxGPT

@ChKashifAli (Kash)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:45) Intro

(01:14) Meet Kash Ali: The Journey Begins

(01:35) Inception of TaxGPT

(02:41) From side project to startup

(04:16) Securing the domain and early success

(07:13) Kash Ali's background and path to Silicon Valley

(13:11) Evolution of TaxGPT

(13:33) Sponsors: Notion | Puzzle

(14:59) TaxGPT's unique value proposition

(19:28) Future of TaxGPT and AI integration

(20:44) Evolution of AI models

(21:48) Enhancing workflows with frontier models

(23:03) Importance of prompting in AI

(28:13) Journey to Y Combinator

(29:55) Fundraising success and future vision

(33:06) Future of accounting and AI

(40:16) Adopting AI solutions in accounting firms

(41:29) Wrap

E39: The AI Economy: How Agents Will Transact Without Us, with Don Gossen CEO of Nevermined

Wed, 19 Mar 2025 07:00:00 -0000

This week, Sasha Orloff sits down with Donald Gossen, CEO of Nevermined, to explore the future of AI-driven payments, highlighting the company's vision for AI agents with independent accounts and transaction protocols, the challenges of dynamic payment systems, the role of blockchain in security, and Nevermined's journey in enabling decentralized AI-to-AI transactions.

SPONSORS:

Notion

Puzzle

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/donald-gossen-40ab96/

https://nevermined.io/

X/SOCIAL:

@Nevermined_io

@dongossen (Donald)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Preview

(00:50) Intro

(01:18) Overview of AI-to-AI payments and decentralized finance

(02:34) Vision behind Nevermined

(04:01) Challenges in AI payment systems

(05:34) Nevermined: The PayPal of AI

(06:52) Future of AI commerce

(11:46) Real-world applications and security

(13:54) Sponsors: Notion | Puzzle

(15:17) Security & trust in AI transactions

(19:39) Evolution of AI agents

(27:45) Building Nevermined and fundraising

(32:31) Wrap

E38: AI-Powered Tax Solutions are Really Here, with Fifteenth Founder Ankur Dahiya

Wed, 12 Mar 2025 08:20:00 -0000

This week, Sasha Orloff is joined by Ankur Dahiya, CEO and founder of Fifteenth, a B2B fintech startup using AI to modernize the tax industry, as they discuss his journey from navigating complex stock options at Flexport to transforming CPA services, the challenges of scaling a tax-focused business, the role of AI in automating tax processes, and his vision for more efficient, accessible tax advisory following a successful funding round.

SPONSORS:

Notion

Puzzle

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/ankurdahiya/

https://www.fifteenth.com

X/SOCIAL:

@sashaorloff (Sasha)

@ankurd (Ankur)

TIMESTAMPS:

(00:00) Intro

(01:37) Guest Introduction: Ankur Dahiya

(02:24) Problem with taxes

(03:01) Birth of Fifteenth

(08:33) Combining human expertise with AI

(12:22) Future of AI in tax solutions

(14:40) Sponsors: Notion | Puzzle

(16:03) Managing personal finances

(19:42) Fundraising and building the team

(25:49) Challenges and advice for founders

(27:55) Tax tips for founders and engineers

(33:12) Wrap

E37: Using AI and Humans to Fix Accounting w/ Matt Tait, CEO of Decimal

Thu, 06 Feb 2025 08:00:00 -0000

In this first episode of Season 2, Sasha Orloff is joined by Matt Tait, CEO of Decimal, to discuss the rise of AI in accounting, Decimal’s recent acquisition of KPMG Spark, and their new strategic partnership with Puzzle. Matt also covers his journey building Decimal, the balance of human expertise in a tech-driven world, and the industry’s future.

SPONSORS:

Puzzle

Found

Found provides small business owners tools to track expenses, calculate taxes, manage cashflow, send invoices and more. Open a Found account for free at https://found.com/econ102

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/mtait83/

https://www.decimal.com/

X/SOCIAL:

@GoDecimal (Decimal)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00) Intro

(00:59) Season 2 changes

(01:48) Exciting times in accounting

(03:12) Interview with Matt Tate, CEO of Decimal

(04:22) Rise and fall of Bench

(06:18) Challenges in the accounting industry

(13:03) Founding and vision of Decimal

(16:46) Sponsors: Puzzle | Found

(18:34) Acquisition of KPMG Spark

(23:11) Team collaboration and roadmap insights

(23:45) Scaling with Puzzle's AI native ledger

(24:31) Evaluating technology partnerships

(28:59) Role of trust and accountability in accounting

(29:43) AI's impact on client experience

(31:08) Human interaction vs. full automation

(36:22) Future of AI in accounting

(43:34) Implementing AI tools at scale

(45:14) Wrap

E36: From Quill to AI: The Evolution of Accounting with David Hartley, former CIO and CPA

Thu, 19 Dec 2024 08:00:00 -0000

In the final episode of season one, Sasha Orloff is joined by David Hartley, a seasoned CPA with over 30 years of experience, as they explore the evolution of accounting from the 15th century to today's AI-driven landscape and discuss how the profession adapts to technological change while preserving its core value of trust.

—

🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse.

—

Highlights from the Episode:

Accounting profession is facing its most significant period of change, with AI and automation creating both challenges and opportunities for practitioners at all levels.
There's currently a major pipeline issue in accounting - with 75% of CPAs approaching retirement age and not enough new talent entering the field.
Despite technological advances, the fundamental need for trust and human interpretation in accounting remains paramount, suggesting AI will augment rather than replace accountants.

—

RECOMMENDED PODCAST:

Check out Modern Relationships, where Erik Torenberg interviews tech power couples and leading thinkers to explore how ambitious people actually make partnerships work. Founders Fund's Delian Asparouhov and researcher Nadia Asparouhova kick off the series with an unfiltered conversation about their relationship evolution.

Apple: https://podcasts.apple.com/us/podcast/id1786227593

Spotify: https://open.spotify.com/show/5hJzs0gDg6lRT6r10mdpVg

YouTube: https://www.youtube.com/@ModernRelationshipsPod

SPONSOR:

📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you - try it for free at https://www.notion.com/upstreampod

—

LINKS:

https://www.linkedin.com/in/davehartley/

—

X/SOCIAL:

@sashaorloff (Sasha)

E35: How to Not Be in the Bottom 90% of Acquisitions with Andrew Gazdecki

Thu, 12 Dec 2024 08:00:00 -0000

In this episode, Sasha Orloff is joined by Andrew Gazdecki, founder of Acquire.com, who shares his expertise on successfully selling companies, maximizing exit value, and key lessons from his own acquisition experiences, with over $500 million in closed deals.

—

🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse.

—

Highlights from the Episode:

Creating a competitive process with multiple potential buyers is crucial for maximizing exit value - "if you have one buyer, you have no buyer"
Proper preparation and documentation (clean financials, confidential information memorandum) significantly speeds up the acquisition process and builds buyer confidence
Being transparent about business challenges upfront ("bruises and all") builds trust and allows you to control the narrative around potential objections

RECOMMENDED PODCAST:

Apple: https://podcasts.apple.com/us/podcast/id1786227593

Spotify: https://open.spotify.com/show/5hJzs0gDg6lRT6r10mdpVg

YouTube: https://www.youtube.com/@ModernRelationshipsPod

—

SPONSOR:

—

LINKS:

Acquire: https://acquire.com/

https://www.linkedin.com/in/agazdecki/

—

X/SOCIAL:

@acquiredotcom (Acquire)

@agazdecki (Andrew)

@sashaorloff (Sasha)

—

TIMESTAMPS:

(00:00) Intro

(02:10) Personal lessons from selling Business Apps

(03:50) Building Acquire.com from personal experience

(06:49) First acquisition story with ESW Capital

(09:28) Negotiating terms and tax considerations

(12:20) Story of Altcoin acquisition

(13:53) Sponsor: Notion

(15:15) Experience at Spiff and path to Acquire.com

(18:35) Maximizing exit value strategies

(25:47) Process of listing on Acquire.com

(27:36) Types of buyers and deal sizes

(29:34) Success stories and notable deals

(32:57) Future plans for Acquire.com

(34:04) Wrap

E34: AI Finance Agents & The CHARGE Framework: JustPaid's Vision for Modern AR

Thu, 05 Dec 2024 08:00:00 -0000

This week, Sasha Orloff sits down with JustPaid founders Daniel Kivatinos, a successful YC founder behind the first iPad medical records company, and Anelya Grant, a Kazakhstan immigrant who built an accounting practice for YC startups, about how their unique backgrounds inspired them to tackle the critical challenge of accounts receivable automation with an AI-powered platform. For full show notes, visit: https://highlightai.com/share/309bb91f-34ee-4052-88e5-28718a9101da

—

🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse.

—

SPONSOR:

—

LINKS:

Streamlining Accounts Receivable: Transforming an Overlooked Cornerstone of Business Operations: https://www.justpaid.ai/blog/streamlining-accounts-receivable

JustPaid: https://www.justpaid.ai

https://www.linkedin.com/in/kivatinos/

https://www.linkedin.com/in/anelya/

—

X/SOCIAL:

@getjustpaid (JustPaid)

@danielkivatinos (Daniel)

@sashaorloff (Sasha)

E33: Growth Levers: A PayPal Veteran's Guide to Startup Success | Matt Lerner on the CRAFTED. Podcast

Tue, 26 Nov 2024 08:30:00 -0000

Today, we’re sharing a special episode from our friends at the Webby Awards-honored CRAFTED. podcast. In this conversation, Dan Blumberg interviews growth expert, SYSTM founder, and former PayPal leader Matt Lerner about his book 'Growth Levers,' offering actionable strategies for startups to identify the 10% of efforts that drive 90% of growth. They discuss common startup pitfalls, the mindset shift to customer-centric thinking, JTBD-style interviewing, and the importance of rapid experimentation. For full show notes, visit: https://highlightai.com/share/af10e152-f30a-403e-805f-d234eb40109a

—

🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse.

—

Check out Dan Blumberg's CRAFTED. where he interviews founders of high growth startups, including from Lattice, Gusto, Moov, Monte Carlo, Customer.io and our own Sasha Orloff!

Apple: https://podcasts.apple.com/us/podcast/crafted-the-tech-podcast-for-founders-makers/id1649355311

Spotify: https://open.spotify.com/show/3xtU2V1jRP89aI1ULRN2GI?si=b5753bd5be14494c

—

SPONSOR:

—

LINKS:

Matt Lerner's company: https://www.systm.co/

CRAFTED. podcast: https://crafted.fm

Growth Levers: https://www.amazon.com/dp/173842622X

—

LinkedIn:

Matt Lerner https://www.linkedin.com/in/matthewlerner/

Dan Blumberg https://www.linkedin.com/in/dblums/

Sasha Orloff https://www.linkedin.com/in/sashaorloff/

E32: AI is Solving Finance’s Biggest Problem - And It’s Not What You Think, with Nicolas Boucher

Thu, 21 Nov 2024 08:00:00 -0000

This week, Nicolas Boucher, a finance influencer with nearly a million LinkedIn followers, shares his journey from corporate finance to becoming a content creator and educator, discuss the impact of AI on finance jobs, and how he uses platforms like LinkedIn to share valuable financial insights. For full show notes, visit: https://highlightai.com/share/af10e152-f30a-403e-805f-d234eb40109a

—

🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse.

—

RECOMMENDED PODCAST: Unpack Pricing

Dive into the dark arts of SaaS pricing with Metronome CEO Scott Woody and tech leaders. Learn how strategic pricing drives explosive revenue growth in today's biggest companies like Snowflake, Cockroach Labs, Dropbox and more.

Apple: https://podcasts.apple.com/us/podcast/id1765716600

Spotify: https://open.spotify.com/show/38DK3W1Fq1xxQalhDSueFg

—

SPONSOR:

—

LINKS:

AI Finance Club: https://ai-finance.club/

https://www.linkedin.com/in/bouchernicolas/

—

X/SOCIAL:

@BoucherNicolas (Nicolas)

@sashaorloff (Sasha)

E31: When 3.6 Million Users Need a New Home with Copilot Money's Andrés Ugarte

Thu, 14 Nov 2024 08:00:00 -0000

This week, Sasha Orloff is joined by Andrés Ugarte to explore the rise of Copilot Money after Mint's shutdown announcement, sharing his journey from frustrated user to founder of a privacy-focused personal finance app, and discussing the challenges of building a product-driven company in a shifting financial landscape. For full show notes, visit: https://highlightai.com/share/31895f5b-d783-4eaa-ab11-ac3214b21ddb

—

RECOMMENDED PODCAST: Unpack Pricing

Apple: https://podcasts.apple.com/us/podcast/id1765716600

Spotify: https://open.spotify.com/show/38DK3W1Fq1xxQalhDSueFg

—

SPONSOR:

🌎ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy.

💳 Imagine total control over your company's spending with Rippling Spend, the all-in-one platform for expense reports, corporate cards, and bill pay. Control spend, set custom approval chains, and close your books 3x faster. Visit https://www.rippling.com/turpentine for a free demo and one month free trial.

LINKS:

Copilot Money: https://copilot.money/

https://www.linkedin.com/in/andresugarte/

X/SOCIAL:

@chuga (Andrés)

@sashaorloff (Sasha)

E30: Paul Barnhurst (The FP&A Guy) on What CEOs Want from FP&A

Thu, 31 Oct 2024 07:00:00 -0000

In this episode of Turpentine Finance, host Sasha Orloff sits down with Paul Barnhurst, a passionate FP&A educator and content creator who shares insights on financial planning & analysis, teaching methodologies, and the evolution of financial tools. For full show notes, visit: https://highlightai.com/share/1823b417-abe8-49bb-8f00-d673e24077b1

📰Be notified early when Turpentine drops new publication: https://www.turpentine.co/exclusiveaccess

RECOMMENDED PODCAST: Unpack Pricing

Apple: https://podcasts.apple.com/us/podcast/id1765716600

Spotify: https://open.spotify.com/show/38DK3W1Fq1xxQalhDSueFg

SPONSOR:

🌎ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy.

💳 Imagine total control over your company's spending with Rippling Spend, the all-in-one platform for expense reports, corporate cards, and bill pay. Control spend, set custom approval chains, and close your books 3x faster. Visit https://www.rippling.com/turpentine for a free demo and one month free trial.

LINKS:

The FP&A Guy: https://www.thefpandaguy.com/

https://www.linkedin.com/in/TheFPandAGuy/

X/SOCIAL:

@sashaorloff

E29: Bootstrapped to $640M: Brad Wiskirchen on M&A, Board Management, and Decision-Making

Thu, 24 Oct 2024 07:00:00 -0000

In this episode, host Sasha Orloff interviews Brad Wiskirchen about his journey with Kount, the AI-driven fraud prevention company he bootstrapped and sold to Equifax for $640 million, while sharing insights from his experience as a founder and now a partner at CVC Capital Partners. For full show notes, visit: https://highlightai.com/share/eec1be56-ae04-4afc-bb24-7ed8523b2176

📰Be notified early when Turpentine drops new publication: https://www.turpentine.co/exclusiveaccess

RECOMMENDED PODCAST: Unpack Pricing

Apple: https://podcasts.apple.com/us/podcast/id1765716600

Spotify: https://open.spotify.com/show/38DK3W1Fq1xxQalhDSueFg

SPONSOR:

LINKS:

Kount: https://kount.com/

https://www.linkedin.com/in/bradwiskirchen/

X/SOCIAL:

@sashaorloff

@KountInc

E28: Airbase CFO Aneal Vallurupalli on Acquisitions, the Chief “Friction” Officer, and Spend Management

Thu, 17 Oct 2024 07:00:00 -0000

In this episode, Sasha Orloff is joined by Aneal Vallurupalli, CFO at Airbase, who drops insights on modern spend management and his journey from M&A to leading finance at a Paylocity acquisition target. Aneal discusses his career trajectory, the impactful role of a CFO in spend management, and how Airbase revolutionizes non-payroll spends in the AI era. Aneal also offers essential advice to CFOs navigating today’s dynamic financial landscape.

🔥 Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/

SPONSORS:

ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Trusted by Notion, Anthropic, and Vanta. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy.

LINKS:

Airbase: https://www.airbase.com/

X/SOCIAL:

@sashaorloff

@AVallurupalli

TIMESTAMPS:

(00:00) Preview

(01:16) Intro

(01:43) Meet Aneal Vallurupalli, CFO of Airbase

(02:28) Understanding Airbase's spend management

(04:33) Aneal’s journey to Airbase

(08:08) Evolution and impact of Airbase

(09:43) Role and strategy as CFO

(17:34) Sponsor: Anrok

(18:59) Balancing flexibility and control in spend management

(21:36) Importance of change management

(23:58) Memorable customer success stories

(27:35) Evolution of software in the CFO's office

(31:21) Trends in selling to different industries

(37:08) Future of Airbase and business spend management

(39:36) Insights on M&A and career journey

(43:37) Reflections on buy-side and sell-side experiences

(45:39) Wrap

E27: Architecting a Global Marketplace for M&A with Flippa CEO Blake Hutchison

Thu, 10 Oct 2024 07:00:00 -0000

In this episode, Sasha Orloff sits down with Blake Hutchison, CEO of Flippa, the leading platform for buying and selling online businesses. Blake shares insights from his career (Xero, Lonely Planet, Good44), and explains how Flippa operates as the ‘investment bank for the 99%,’ providing a marketplace for subscale business transactions. The episode dives into the opportunities presented by the marketplace, key deal characteristics, and the different buyer segments. They also discuss the importance of financial literacy for subscale businesses, provide tips for first-time buyers, and offer predictions for the future of flipping businesses.

🔥Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/

RECOMMENDED PODCAST:

🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel.

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937

Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz

SPONSORS:

RIPPLING

Imagine total control over your company’s spending with Rippling Spend, the all-in-one platform for expense reports, corporate cards, and bill pay. Control spend, set custom approval chains, and close your books 3x faster. Visit https://www.rippling.com/turpentine for a free demo and one month free trial.

ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy.

LINKS:

Flippa: https://flippa.com/

https://www.linkedin.com/in/blakehutchison/

X/SOCIAL:

@sashaorloff

@Flippa

TIMESTAMPS:

(00:00) Preview

(01:20) Intro

(02:26) Blake's career journey

(03:37) Flippa: The investment bank for the 99%

(05:55) Focus on digital assets

(07:20) Selling and buying on Flippa

(14:20) Buyer types and market dynamics

(18:30) Sponsors: Rippling | Anrok

(21:22) Investing in digital assets

(26:28) Navigating the first-time buyer market

(28:05) Buyer intent and market trends

(33:47) Common deal breakers in business sales

(36:46) Financial literacy and cloud accounting

(44:27) Future trends in online business flipping

(47:47) Getting started with Flippa

(49:02) Wrap

E26: Why Finance Software is About to Change, with Sapphire Ventures' Jane Lee and Aditya Reddy

Thu, 03 Oct 2024 07:00:00 -0000

In this episode, Sasha Orloff welcomes Jane Lee and Aditya Reddy of Sapphire Ventures to unpack their paper, “Rise of the Next Gen CFO,” which features a market map of CFO tools and identifies key trends and predictions. Jane and Aditya discuss how finance roles are transforming, the convergence of finance and data science, the influence of AI, and emerging investment strategies in this fast-paced sector.

Nothing presented within this podcast is intended to constitute investment advice, and under no circumstances should any information provided herein be used or considered as an offer to sell or a solicitation of an offer to buy an interest in any investment fund managed by Sapphire Ventures (“Sapphire”). Information provided reflects Sapphires’ views as of a time, whereby such views are subject to change at any point and Sapphire shall not be obligated to provide notice of any change. No assumptions should be made that investments or strategies described were or will be profitable. Due to various risks and uncertainties, actual events, results or the actual experience may differ materially from those reflected or contemplated in these statements. Nothing contained in this podcast may be relied upon as a guarantee or assurance as to the future success of any particular company or strategy. Past performance is not indicative of future results.

SPONSORS:

NETSUITE: More than 40,000 businesses have already upgraded to NetSuite by Oracle, the #1 cloud ERP bringing accounting, financial management, inventory, HR, into ONE proven platform. Download the CFO's guide to AI and Machine Learning at https://netsuite.com/102

METAVIEW is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics

OMNEKY is an omnichannel creative generation platform that lets you launch hundreds of thousands of ad iterations that actually work customized across all platforms, with a click of a button. Omneky combines generative AI and real-time advertising data. Mention "Cog Rev" for 10% off https://www.omneky.com/

LINKS:

Rise of the Next Gen CFO: https://sapphireventures.com/blog/rise-of-the-next-gen-cfo-the-evolution-of-finances-role-and-tech-stack/

Sapphire Ventures: https://sapphireventures.com/

X/SOCIAL:

@sashaorloff

@leejane09

@adityareddy97

TIMESTAMPS:

(00:00) Preview

(00:53) Intro

(01:18) Viral market map by Sapphire Ventures

(02:23) Rise of the Next Gen CFO

(06:25) Key findings from the paper

(10:57) Impact of AI on finance

(18:09) Sponsors: Anrok | Netsuite

(20:36) Complexities with crypto assets

(24:22) AI affecting different industries

(28:22) Investment insights from Sapphire Ventures

(34:58) Sponsors: Metaview | Omneky

(36:27) Platform risks

(41:06) Sapphire Ventures' focus

(43:37) Wrap

E25: What Separates Good From Great Treasury, with Eugene Spevakov

Thu, 26 Sep 2024 07:00:00 -0000

In this episode, Sasha Orloff is joined by Eugene Spevakov, the Treasurer and Head of Corporate FP&A at 6sense, treasury expert, and veteran CFO. Sasha and Eugene dive deep into the Treasury function: how it differs across industries, how a scaling startup will know when it’s time to hire for the role, how to structure the function, and what separates a great treasurer from merely good. Eugene offers a masterclass on leveraging treasury to drive growth, improve cash flow, and allocate risk strategically in an uncertain world.

🔥Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/

RECOMMENDED PODCAST:

🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel.

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937

Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz

SPONSORS:

LINKS:

https://www.linkedin.com/in/eugene-spevakov-cfa/

6sense: https://6sense.com/

X/SOCIAL:

@sashaorloff

TIMESTAMPS:

(00:00) Preview

(00:49) Intro

(01:14) Understanding treasury

(02:22) Meet Eugene Spevakov: A treasury expert

(03:39) Basics of treasury functions

(05:40) Real-world treasury challenges and risks

(09:12) Industry-specific treasury insights

(14:07) Sponsors: Anrok | Netsuite

(16:30) Treasury in software companies

(22:32) Risk management and allocation

(27:29) Sponsors: Metaview | Omneky

(28:58) When to hire a treasury professional

(30:07) Understanding and managing business risks

(32:40) Challenges and solutions in treasury functions

(37:08) Role and excitement of treasury

(43:12) Tools and resources for treasury management

(47:40) Advice for building a treasury function

(50:32) Wrap

E24: The ROI of Storytelling: Camille Ricketts (ex-Notion, FRR, Tesla)on Content as a Business Driver

Thu, 19 Sep 2024 07:00:00 -0000

In this episode, Sasha Orloff sits down with Camille Ricketts, former Co-Head of Marketing at Notion, Editor of First Round Review and Elon’s comms manager at Tesla, to talk about the ROI of content as a growth driver. Camille, currently a partner at XYZ Venture Capital, played a key role in persuading Sasha years ago to invest in content as a revenue channel. In this episode she shares her invaluable insights from her roles at Notion, Tesla, and First Round Review. Tune in to hear Camille’s compelling arguments for CEOs and VPs about the strategic value of content marketing. This is a must-listen for founders, finance leaders, and anyone eager to leverage content for growth.

🔥Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/

RECOMMENDED PODCAST:

🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel.

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937

Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz

SPONSORS:

NETSUITE: More than 37,000 businesses have already upgraded to NetSuite by Oracle, the #1 cloud financial system bringing accounting, financial management, inventory, HR, into ONE proven platform. If you're looking for an ERP platform, get a one-of-a-kind flexible financing program on NetSuite: https://netsuite.com/102

BRAVE: Get first-party targeting with Brave’s private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/brave-ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign.

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LINKS:

https://www.linkedin.com/in/camillericketts/

XYZ: https://www.xyz.vc/

X/SOCIAL:

@sashaorloff

@camillericketts

TIMESTAMPS:

(00:00) Episode Preview

(00:58) Conversation with Camille Ricketts

(02:11) Camille's journey at Notion

(04:34) Content as a measurable growth strategy

(12:00) Effective use of testimonials and case studies

(15:45) Case studies and emotional engagement

(17:54) Sponsors: Netsuite | Metaview

(19:41) Measuring content success

(24:25) Tactical tips for effective call to action

(26:08) Figma and Stripe

(27:37) Founding story of First Round Review

(30:30) Sponsors: Brave | Omneky

(31:52) Iterating content formats and overcoming fear

(37:04) Role of AI in content creation

(42:57) Insights from Tesla and preparing for the unexpected

(47:24) Wrap

E23: “Founder Mode"? Setting the Record Straight with Jim Cook

Thu, 12 Sep 2024 08:05:00 -0000

When Y Combinator's Paul Graham released his viral essay "Founder Mode," it sparked a firestorm in the tech world. Based on a private talk by Airbnb's Brian Chesky and endorsed by the likes of Elon Musk and Patrick Collison, the piece garnered over 20 million views. Enter Jim Cook, legendary Silicon Valley CFO (Netflix, Intuit, Mozilla) who just wrote a counterargument to set the record straight. Cook challenges the simplistic notion of founder supremacy — where only 10% succeed — and offers a different Leadership Mode framework for building high-performance, generational companies.

🔥Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/

RECOMMENDED PODCAST:

🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. They unpack their hottest takes on the future of tech, business, venture, investing, and politics.

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937

Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz

YouTube: https://www.youtube.com/@ThisWontLastpodcast

SPONSORS:

LINKS:

Cook’s Playbooks https://jcookflix.substack.com/

Founder Mode PG https://paulgraham.com/foundermode.html

Lenny’s Podcast episode with Brian Chesky https://www.youtube.com/watch?v=4ef0juAMqoE

Product-CEO Paradox by Ben Horowitz https://a16z.com/why-founders-fail-the-product-ceo-paradox/

Hard Thing About Hard Things by Ben Horowitz https://a16z.com/books/the-hard-thing-about-hard-things/

Scaling People with Claire Hughes Johnson https://www.goodreads.com/book/show/63063173-scaling-people

X/SOCIAL:

@sashaorloff

@cookflix

TIMESTAMPS:

(00:00) Episode preview

(00:26) Intro

(00:51) Founder Mode essay

(04:13) Challenges of polarized arguments

(07:44) Importance of leadership mode

(10:59) Balancing founder and scaling modes

(15:01) Sponsors: Netsuite | Metaview

(16:49) Trust and transparency in leadership

(20:41) Importance of creating a culture

(24:57) Leading with values and behaviors

(29:48) Sponsors: Brave | Omneky

(31:13) Importance of documentation

(36:45) Balancing founder and manager roles

(39:06) Structuring ownership and accountability

(43:06) Founders as Coaches and Captains

(48:12) Specialized operators in finance

(50:41) Scaling company to public

(53:50) Wrap

E22: Evolution of the CFO Role, Compensation, and Interview Success with Chris Sands of the F Suite

Thu, 05 Sep 2024 09:56:00 -0000

In this episode, Sasha Orloff is joined by Chris Sands, Head of Jobs at The F Suite, to discuss the landscape of finance leadership and career advancement in 2024. Sands unpacks the changing role of CFOs and how to navigate compensation from the vantage point of CFOs (and the CEOs hiring for the role). This episode offers invaluable insights on how to stay relevant, adaptable, and ahead of the curve in your finance career.

🔥Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/

RECOMMENDED PODCAST:

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937

Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz

YouTube: https://www.youtube.com/@ThisWontLastpodcast

SPONSORS:

LINKS:

http://fsuite.co

https://www.fsuite.co/compensation-survey

http://lsuite.co

http://www.thesuite.com

X/SOCIAL:

@sashaorloff

@chris_sands_

TIMESTAMPS:

(00:00) Episode preview

(01:16) Intro

(01:40) Meet Chris Sands: Head of Jobs at The F Suite

(03:06) Evolving role of the CFO

(09:11) Strategies for aspiring CFOs

(12:29) Candidate-first approach in recruitment

(13:56) Then vs Now: Hiring CFOs

(19:14) Preparing candidate for interviews

(22:53) Sponsors: Netsuite | Metaview

(24:40) Best practices in recruiting finance teams

(26:19) Role of CFO in the hiring process

(27:28) Advice for recruiting CFOs

(29:28) Sponsors: Brave | Omneky

(30:56) Key traits of a great CFO

(32:52) Evolution of CFO roles

(34:10) Misconceptions on job search

(37:56) CFO compensation insights

(44:49) Negotiation strategies for CFOs

(48:04) Non-negotiable compensation offers

(48:59) F Suite: Building a community for CFOs

(52:39) Wrap

E21: From Silicon Valley to Lake Tahoe Ski Resort CFO | Valerie Burman

Thu, 29 Aug 2024 07:00:00 -0000

In this episode, Sasha Orloff is joined by Valerie Burman, CFO of Sugar Bowl Resort in Lake Tahoe and former VP at Workday and SAP, shares her unique journey from being an executive at Silicon Valley tech companies to becoming the CFO of a ski resort. Valerie talks about her philosophy on building the dream team, the importance of understanding business acumen in a CFO role, and strategies for achieving long-term liquidity. She also reflects on hard won lessons from multiple M&As and corpdev.

Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/

RECOMMENDED PODCAST:

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937

Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz

YouTube: https://www.youtube.com/@ThisWontLastpodcast

SPONSORS:

More than 37,000 businesses have already upgraded to NetSuite by Oracle, the #1 cloud financial system bringing accounting, financial management, inventory, HR, into ONE proven platform. If you're looking for an ERP platform, get a one-of-a-kind flexible financing program on NetSuite: https://netsuite.com/102

Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics

X/SOCIAL:

Sasha on X: @sashaorloff

Valerie's LinkedIn: https://www.linkedin.com/in/burmanval/

TIMESTAMPS:

(00:00) Introduction

(01:45) Valerie Berman: From tech to Tahoe

(03:00) Transitioning to Sugar Bowl

(05:21) Day one as CFO: Skiing and listening

(07:02) Unique aspects of Sugar Bowl

(08:13) Balancing fun and financials

(13:05) Sponsors: Netsuite | Metaview

(14:54) Measuring success and setting goals

(24:27) Navigating seasonal business challenges

(30:00) Building a dream team at Sugar Bowl

(32:24) Sponsors: Brave | Omneky

(33:46) Insights on M&A and corporate development

(36:24) Decision making in private companies

(42:02) Significant role of cultural alignment

(46:07) Advice for aspiring CFOs

(48:06) Closing remarks and outro

E20: Rishi Garg’s M&A Playbooks from Twitter and Square

Thu, 22 Aug 2024 07:00:00 -0000

In this episode, Rishi Garg, former Head of Corporate Development at Twitter and Square, shares insider knowledge on tech acquisitions. He explains when companies should start considering M&A and the three key approaches: tops down, bottoms up, and strategy influence. Rishi reveals how he managed up to 15 deals in 12 months and why integration is crucial for M&A success. He debunks common M&A misconceptions and discusses the "sins of omission" - deals he regrets not making. The conversation shifts to his current role as a VC at Mayfield Fund, offering a unique perspective on both sides of acquisitions.

LINKS:

https://www.twitter.com/rishigarg

https://www.mayfield.com/

RECOMMENDED PODCAST:

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937

Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz

YouTube: https://www.youtube.com/@ThisWontLastpodcast

SPONSORS:

The Brave search API can be used to assemble a data set to train your AI models and help with retrieval augmentation at the time of inference. All while remaining affordable with developer first pricing, integrating the Brave search API into your workflow translates to more ethical data sourcing and more human representative data sets. Try the Brave search API for free for up to 2000 queries per month at https://brave.com/api

Omneky:

X/SOCIAL:

@sashaorloff

@rishigarg (Rishi)

TIMESTAMPS:

(00:00:00) Introduction

(00:02:53) How companies should think about M&A and corp dev

(00:06:58) Signs that a company is ready to consider M&A

(00:11:37) Different approaches to M&A: tops down, bottoms up, and strategy influencing

(00:16:52) How to start building an M&A team

(00:18:16) Sponsors: Netsuite | Metaview

(00:22:15) Misconceptions about M&A in Silicon Valley

(00:26:53) Valuation considerations in M&A deals

(00:34:31) Current state of M&A market and opportunities

(00:38:24) Sponsors: Omneky | Brave

(00:39:47) How M&A deals happen and relationship building

(00:45:55) Reasons why M&A deals don't work out

(00:51:50) Transition to Rishi's experience as a venture capitalist

(00:57:50) Advice for founders considering M&A

(01:02:09) Rishi's current interests in investing, particularly in AI and new platforms

E19: From Lean Startup to Long-Term Thinking: Eric Ries Reinvents the Stock Exchange

Thu, 15 Aug 2024 07:00:00 -0000

In this episode of Turpentine Finance, Sasha sits down with Eric Ries, author of "The Lean Startup" and founder of the Long-Term Stock Exchange (LTSE). Ries shares the challenging journey of creating a new national securities exchange designed to promote long-term thinking in public companies. He discusses the obstacles faced in gaining SEC approval, the misconceptions about corporate governance, and why many companies struggle with balancing short-term pressures and long-term vision. Ries offers valuable insights for CEOs and CFOs considering going public or dual-listing, emphasizing the importance of aligning investors with a company's long-term mission. This conversation explores how rethinking capital allocation and corporate structure can lead to more sustainable, successful businesses.

LINKS:

The LTSE: https://ltse.com/

The Lean Startup: https://theleanstartup.com/

Listen here at: https://www.ericriesshow.com/

RECOMMENDED PODCAST

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937

Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz

YouTube: https://www.youtube.com/@ThisWontLastpodcast

SPONSORS:

RIPPLING SPEND:

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NETSUITE

BRAVE:

X/SOCIAL:

@sashaorloff

@ericries (Eric)

TIMESTAMPS:

(00:00:00) - Introduction and opening quote from Eric Ries

(00:02:18) - Explanation of what the Long-Term Stock Exchange (LTSE) is

(00:07:11) - Eric's background and journey to founding LTSE

(00:14:29) - The challenge of convincing investors to fund LTSE

(00:16:03) - Sponsors: Netsuite | Rippling Spend

(00:21:47) - Eric's experience navigating the SEC approval process

(00:29:38) - Sponsor: Omneky

(00:31:30) - Discussion on how companies are notified of SEC approval

(00:42:36) - Challenges and questions companies ask behind the scenes

(00:50:36) - Brief mention of companies listed on LTSE

(00:58:36) - The importance of allocating shares to long-term investors

(01:01:21) - What's next for LTSE and Eric Ries

(01:02:49) - Closing remarks and outro

E18: Jody Padar, CPA, on Solving Accounting's Incentive Misalignment Using Radical Pricing

Thu, 08 Aug 2024 07:00:00 -0000

In this episode, Sasha sits down with Jody Padar, the Radical CPA, 3x author, to discuss the incentive misalignment in accounting firms, and how radical pricing can solve it. Jody shares her insights on the evolving landscape of accounting, discussing the need for firms to adapt to new technologies, embrace value-based pricing, and shift from traditional hourly billing models. She emphasizes the importance of redefining the accountant-client relationship in the digital age, advocating for a more advisory-focused approach. Jody also addresses the challenges facing the accounting profession, including talent shortages and the impact of automation, while offering her vision for the future of accounting firms.

🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj

This show is a part of the Turpentine podcast network. Learn more: https://www.turpentine.co

Get Turpentine Finance directly in your inbox. Subscribe to our newsletter at https://turpentine-finance.beehiiv.com/ and receive key takeaways from each episode

RECOMMENDED PODCASTS:

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937

Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz

YouTube: https://www.youtube.com/@ThisWontLastpodcast

LINKS:

Radical Pricing by Jody Padar: https://cpatrendlines.com/shop/jp24pri-jody-padar-radical-pricing-how-to-optimize-profits-delight-clients-and-build-a-top-value-firm-jp24pri/

Connect with Jody on Linkedin: https://www.linkedin.com/in/jody-padar-18a9711

SPONSORS:

📈 NetSuite has 25 years of providing financial software for all your business needs. More than 36,000 businesses have already upgraded to NetSuite by Oracle, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you’re looking for an ERP platform head to NetSuite: http://netsuite.com/zen - NetSuite has extended a one-of-a-kind flexible financing program for a few more weeks.

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TIMESTAMPS:

(00:00:00) Episode preview

(00:01:05) Introduction to Turpentine Finance Podcast

(00:01:31) Meet Jody: The Radical CPA

(00:03:06) The disconnect in accounting firms

(00:05:53) Jody's journey into accounting

(00:07:23) Innovating in a firm with technology and cloud solutions

(00:12:58) Challenges in changing the pricing model

(00:18:04) The role of automation in accounting

(00:24:32) Innovative constraints in small firms

(00:25:33) Realizing pricing as the core problem

(00:27:20) Transitioning to value-based pricing

(00:36:01) The role of AI and technology in accounting

(00:37:41) The future of bookkeeping firms

(00:39:56) Reimagining the accounting profession

(00:43:04) Strengthening accountant-client relationships

(00:47:39) Training the next generation of accountants

(00:49:40) Conclusion and final thoughts

E17: Why a16z is All-In on AI for Finance Teams with Partner Seema Amble

Thu, 01 Aug 2024 07:00:00 -0000

In this episode, Sasha sits down with Seema Amble, Partner at Andreessen Horowitz. Seema shares her research on the transformation of the CFO’s office, and how generative AI is powering financial teams. She discusses how AI can empower CFOs and finance teams to focus on strategic rather manual tasks, increasing client communication through automation, the impact of AI on valuations in service businesses such as law and accounting, and the progression from “service as a software” vs “software as a service”. Seema also discusses investing cycles, and how AI adoption in enterprise might follow the trajectory of other technologies, beginning with consumer adoption first.

🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj

This show is a part of the Turpentine podcast network. Learn more: https://www.turpentine.co

Get Turpentine Finance directly in your inbox. Subscribe to our newsletter at https://turpentine-finance.beehiiv.com/ and receive key takeaways from each episode

RECOMMENDED PODCASTS:

🎙️1 to 100 | Hypergrowth Companies Worth Joining

Every week we sit down with the founder of a hyper-growth company you should consider joining. Our goal is to give you the inside story behind breakout, early stage companies potentially worth betting your career on. This season, discover how the founders of Modal Labs, Clay, Mercor, and more built their products, cultures, and companies.

Spotify:https://open.spotify.com/show/70NOWtWDY995C8qDqojxGw

Apple: https://podcasts.apple.com/podcast/id1762756034

SPONSORS:

NETSUITE

COMMANDBAR

BABBEL

LINKS:

The CFO in Crisis: https://a16z.com/the-cfo-in-crisis-mode-modern-times-call-for-new-tools/

Death, Taxes, and Accounting: https://a16z.com/generative-ai-in-accounting/

X/SOCIAL

@seema_amble (Seema)

@sashaorloff (Sasha)

TIMESTAMPS:

(00:00:00) Introduction to Turpentine Finance Podcast

(00:01:44) Discussing the CFO in Crisis Mode article

(00:02:10) Challenges faced by CFOs with legacy software

(00:06:35) The pyramid graph of finance team tasks and market insights

(00:15:10) Generative AI's impact on finance

(00:16:24) Emerging trends and changes in the market

(00:20:14) The rise of bundled solutions in finance

(00:22:49) Death, taxes, and AI: Transforming accounting

(00:24:33) The excitement of AI in accounting

(00:26:42) Challenges and opportunities in AI adoption

(00:29:29) Incentive alignment and talent development in service businesses

(00:32:36) The future of services as software

(00:34:14) AI's impact on business models and valuation

(00:38:17) Andreessen Horowitz's AI investment strategy

(00:40:07) Future trends and predictions in AI

(00:44:12) Engaging with Andreessen Horowitz

(00:45:18) Conclusion and call to action

E16: CFO Dilemmas Decoded: Growth vs. Profit, VC vs. PE, and M&A Insights w/ Dan Fletcher, CFO of Planful

Fri, 26 Jul 2024 05:28:00 -0000

In this episode of Turpentine Finance, Sasha sits down with Dan Fletcher, CFO of Planful. They discuss how CFOs can build trust with the CEO and the board, balancing growth and profitability across different company stages, the nuances of working with VC versus PE investors, and more. Dan also shares his perspective of working at Planful, building infrastructure for CFOs.

🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj

This show is a part of the Turpentine podcast network. Learn more: https://www.turpentine.co

Get Turpentine Finance directly in your inbox. Subscribe to our newsletter at https://turpentine-finance.beehiiv.com/ and receive key takeaways from each episode

RECOMMENDED PODCASTS:

🎙️1 to 100 | Hypergrowth Companies Worth Joining

Spotify:https://open.spotify.com/show/70NOWtWDY995C8qDqojxGw

Apple: https://podcasts.apple.com/podcast/id1762756034

SPONSORS:

NETSUITE

COMMANDBAR

BABBEL

LINKS:

https://planful.com/

X/SOCIAL:

Dan Fletcher on Linkedin: https://www.linkedin.com/in/danfletchersf/

@sashaorloff (Sasha's X)

TIMESTAMPS:

(00:00) The best advice for growth and profitability

(02:13) Meet Dan Fletcher: Navigating CFO challenges

(02:57) Stakeholder management for CFOs

(04:22) Building trust with the CEO

(08:30) Growth vs. profitability: A balanced approach

(17:28) Navigating M&A discussions

(20:43) Preparing for board meetings

(25:08) Common questions CFOs face

(25:45) The importance of knowing your business

(26:24) The role of the CFO in board meetings

(27:22) Differences between venture-backed and private equity-backed boards

(29:00) Career path to CFO: CPA vs. corporate finance

(33:53) Essential skills for aspiring CFOs

(35:04) The role of the controller in strategic finance

(37:07) Planful's success and CFO insights

(43:02) Future of AI in financial planning

(45:28) Conclusion and final thoughts

E15: Building Tax Compliance for Tech Companies with Michelle Valentine, Cofounder and CEO of Anrok

Thu, 18 Jul 2024 08:15:00 -0000

In this episode, Sasha sits down with Michelle Valentine, Co-founder and CEO of Anrok, the tax compliance infrastructure for the internet economy. They discuss the complexities of sales tax in the digital age, the historical context, regulatory changes, and challenges faced by startups operating online. Michelle shares her journey from VC at Index Ventures to founding Anorak and provides valuable advice for finance leaders and founders on navigating sales tax issues effectively.

🔥 Apply to join over 400 Founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj

This show is a part of the Turpentine podcast network. Learn more: https://www.turpentine.co

Get Turpentine Finance directly in your inbox. Subscribe to our newsletter at https://turpentine-finance.beehiiv.com/ and receive key takeaways from each episode

RECOMMENDED PODCASTS:

🎙️1 to 100 | Hypergrowth Companies Worth Joining

Spotify:https://open.spotify.com/show/70NOWtWDY995C8qDqojxGw

Apple: https://podcasts.apple.com/podcast/id1762756034

SPONSORS:

NETSUITE

COMMANDBAR

BABBEL

LINKS:

https://www.anrok.com/

X/SOCIAL:

@sashaorloff (Sasha)

@_vltn (Michelle)

TIMESTAMPS:

(00:00) Episode preview

(01:12) The complexity of sales tax in the digital age

(03:40) The evolution of sales tax laws

(05:41) The impact of remote work and Supreme Court rulings

(07:20) Local vs. state tax compliance

(10:47) How Anrok solves sales tax issues

(12:25) The importance of early sales tax compliance

(15:13) Anrok's approach to sales tax management

(18:30) Address data quality and sales tax

(24:06) Common misconceptions about tax responsibility

(26:45) From venture capitalist to founder

(28:01) Building a strong founding team

(32:57) The why now for Anrok

(35:41) Advice for founders and finance teams

(39:49) The role of accounting firms and fractional CFOs

(42:47) Anrok's vision and future

E14: Revenue Models 101 & the New Stack with Riya Grover, CEO of Sequence

Thu, 11 Jul 2024 07:00:00 -0000

In this episode, Sasha sits down with Riya Grover, CEO and Cofounder of Sequence, to discuss the evolving landscape of B2B revenue models and pricing strategies. They dive deep into the challenges modern software companies face in managing complex hybrid pricing models and the increasing adoption of usage and hybrid-based pricing. Riya also shares Sequence's approach to unifying the quote-to-cash process, bridging the gap between sales and finance teams, the limitations of traditional revenue management tools, and much more.

🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj

This show is a part of the Turpentine podcast network. Learn more: https://www.turpentine.co

Get Turpentine Finance directly in your inbox. Subscribe to our newsletter at https://turpentine-finance.beehiiv.com/ and receive key takeaways from each episode

RECOMMENDED PODCAST:

🎙️ Second Opinion - A new podcast for health-tech insiders from Christina Farr of the Second Opinion newsletter. Join Christina Farr, Luba Greenwood, and Ash Zenooz every week as they challenge industry experts with tough questions about the best bets in health-tech.

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1759267211

Spotify: https://open.spotify.com/show/0A8NwQE976s32zdBbZw6bv

📈 ECON 102 W/ NOAH SMITH - Keeping econ entertaining - Noahpinion author Noah Smith and Erik Torenberg break down business news and politics every week.

Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH

Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812

SPONSORS:

NETSUITE

COMMANDBAR

BABBEL

LINKS:

https://www.sequencehq.com

X/SOCIAL

@sashaorloff (Sasha)

@Riya_78 (Riya)

TIMESTAMPS

(00:00:00) Introduction to revenue management challenges

(00:02:07) Evolution of revenue models

(00:04:23) Hybrid pricing and usage-based models

(00:05:32) Complexities in revenue management

(00:06:46) Modern sales and finance operations

(00:09:38) Driving factors behind revenue model changes

(00:15:12) Software evolution and challenges

(00:36:57) Sequence: simplifying quote to revenue

(00:40:42) Closing thoughts and advice for finance teams

E13: Architecting IPO Readiness from Day One with Nadia Asoyan, Formerly of Square, Robinhood, and Strike

Thu, 27 Jun 2024 07:57:00 -0000

In this episode, Sasha sits down with Nadia Asoyan, former CFO of Strike, Robinhood, and Controller at Square. Nadia shares her journey from EY to Silicon Valley's top fintech rocketships, offering invaluable insights on transitioning from accounting to CFO positions. She discusses the challenges of IPO readiness, the evolution of financial processes in fast-growth startups, and the delicate balance between growth and profitability. Nadia also provides candid advice for aspiring CFOs, emphasizing the importance of cross-functional partnerships and data literacy.

🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj

This show is a part of the Turpentine podcast network. Learn more: https://www.turpentine.co

Get Turpentine Finance directly in your inbox. Subscribe to our newsletter at https://turpentine-finance.beehiiv.com/ and receive key takeaways from each episode

RECOMMENDED PODCAST:

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1759267211

Spotify: https://open.spotify.com/show/0A8NwQE976s32zdBbZw6bv

📈 ECON 102 W/ NOAH SMITH - Keeping econ entertaining - Noahpinion author Noah Smith and Erik Torenberg break down business news and politics every week.

Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH

Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812

SPONSORS:

NETSUITE

COMMANDBAR

BABBEL

LINKS:

Strike: https://strike.me/

X/SOCIAL

@sashaorloff

@NadiaAsoyan

TIMESTAMPS:

(00:00) Introduction

(01:06) Nadia’s Accounting Origins

(04:17) Big Four Lessons

(07:38) Square's Early Days

(09:03) The Audit to In-House Transition

(11:22) IPO Readiness at Square

(17:05) Building Processes at Robinhood

(18:21) Sponsors: Netsuite | CommandBar

(21:00) Attracting Founders

(24:30) Expanding Responsibilities

(28:18) Evolving Processes

(28:42) Sponsors: Babbel | Attio

(32:33) Advice for Accounting Professionals

(35:05) Board Management and Fundraising

(42:00) Board Meetings

(45:20) Growth vs. Profitability

(48:32) Counterintuitive Advice

(50:00) Misconceptions and Unsolved Problems

(54:41) Square IPO Challenges

(59:48) Complexity and Automation

(1:04:10) Free Products and Hyper Growth

(1:07:01) Pricing Models

(1:10:22) Budget Setting

(1:14:20 ) Wrap

E12: Customer Obsession Meets Unit Economics: Product-Finance Harmony w/ Gusto's CPO Tomer London

Fri, 21 Jun 2024 13:49:00 -0000

In this episode, Tomer London, co-founder and Chief Product Officer at Gusto, shares insights into aligning product and finance teams for responsible growth. He dives deep into the frameworks and practices Gusto employed to make trade-offs between core products, expansion opportunities, and moonshot ideas - all while maintaining a relentless focus on customer needs and healthy unit economics. Tomer discusses Gusto's thoughtful, iterative approach to product development, avoiding the pitfalls of pursuing growth at all costs. He provides a candid look into Gusto's fundraising philosophy and managing the product-finance relationship through the company's evolution from startup to industry leader.

🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj

This show is a part of the Turpentine podcast network. Learn more: https://www.turpentine.co

Get Turpentine Finance directly in your inbox. Subscribe to our newsletter at https://turpentine-finance.beehiiv.com/ and receive key takeaways from each episode

RECOMMENDED PODCAST:

Apple Podcasts: https://podcasts.apple.com/us/podcast/id1759267211

Spotify: https://open.spotify.com/show/0A8NwQE976s32zdBbZw6bv

📈 ECON 102 W/ NOAH SMITH - Keeping econ entertaining - Noahpinion author Noah Smith and Erik Torenberg break down business news and politics every week.

Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH

Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812

---

SPONSORS:

ATTIO

📊 Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine

NETSUITE

COMMANDBAR

BABBEL

LINKS:

gusto.com

X/SOCIAL

@sashaorloff

@tomerlondon

TIMESTAMPS:

(00:00) Intro

(01:25) Landing on Payroll

(03:46) Payroll as a Wedge

(05:20:)The Importance of Emotional Pain Points

(07:23) Dream Big, Make it Real

(13:06) The Three Horizons Framework

(15:07) The Importance of Product & Finance Alignment

(17:08) Sponsor: NetSuite | Attio

(21:00) Milestones and Accountability

(24:00) Killing Products

(28:30) Staying Focused Amidst Competition

(30:39) Sponsor: beehiiv | Babbel

(34:00) Fundraising Strategy

(36:46) Evolving Thinking on Profitability

(40:25) The Power of Customer Connection

(42:00) The Future of Gusto

(43:12) Wrap

E11: CFO Whisperer Jim Cook of Netflix, Intuit, & Mozilla: "Stop Trying To Be Precise"

Thu, 13 Jun 2024 08:36:00 -0000

In this episode, Sasha sits down with Jim Cook, dubbed the CFO Whisperer, after 30 years in Silicon Valley as CFO at Netflix, Intuit, and Mozilla. Jim shares CFO hiring mistakes and the misunderstandings most board members and investors have about the CFO role, why being precise is the finance professional’s Achilles heel, tactical advice for impactful communication in board meetings, and more.

🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj

This show is a part of the Turpentine podcast network. Learn more: https://www.turpentine.co

RECOMMENDED PODCAST:

Patrick McKenzie (@patio11) talks to experts who understand the complicated but not unknowable systems we rely on. You might be surprised at how quickly Patrick and his guests can put you in the top 1% of understanding for stock trading, tech hiring, and more.

Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH

Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812

📈 ECON 102 W/ NOAH SMITH - Keeping econ entertaining - Noahpinion author Noah Smith and Erik Torenberg break down business news and politics every week.

Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH

Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812

---

SPONSORS:

ATTIO

NETSUITE

BEEHIIV

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LINKS:

Jim's Linkedin: https://www.linkedin.com/in/cookflix

Benchboard: https://www.benchboard.com/

X/SOCIAL:

@sashaorloff (Sasha)

@cookflix (Jim)

TIMESTAMPS

(00:00) Preview and Intro

(03:19) Early lessons from Intuit

(05:28) Evolution of finance teams

(09:06) Customer-centric finance

(11:14) Effective stakeholder management

(12:47) Strategic decision making in finance

(15:39) Board meetings preparation

(19:04) Sponsor: Netsuite | Attio

(21:07) Meaningful discussions on board meetings

(24:07) How to be a successful CEO

(31:38) Sponsor: Beehiiv | Babbel

(34:11) Early days of Netflix

(37:05) Monetization strategies

(44:14) Hiring the right CFO

(47:26) Interview question for a CFO candidate

(49:35) Introducing BenchBoard

(53:38) Common skills and advice

(57:19) Wrap

E10: How OpenAI Controller Sowmya Raganathan Uses AI to Superpower Accounting

Thu, 06 Jun 2024 06:19:00 -0000

OpenAI Controller Sowmya Ranganathan sits with Sasha Orloff to share accounting insights from her experience at Square, Rippling, and OpenAI. She discusses automation and using AI in accounting, how difficult software motivated her to make the move to Controller at Rippling, and how she’s streamlining the accounting workflow at OpenAI, where she is currently Controller. Sowmya also explains how AI is making accounting easier and why future accounting teams may be small and broadly skilled.

🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj

RECOMMENDED PODCAST:

Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH

Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812

📈 ECON 102 W/ NOAH SMITH - Keeping econ entertaining - Noahpinion author Noah Smith and Erik Torenberg break down business news and politics every week.

Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH

Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812

---

This show is a part of the Turpentine podcast network. Learn more: https://www.turpentine.co

---

SPONSORS:

ATTIO

NETSUITE

BEEHIIV

BRAVE

🎯Get first-party targeting with Brave’s private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/brave-ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign.

---

This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co.

---

X/SOCIAL:

https://twitter.com/sashaorloff (Sasha)

https://twitter.com/heysowmya (Sowmya)

---

TIMESTAMPS:

(00:00) Preview and Intro

(02:51) Soumya's Journey: From Square to Rippling

(03:14) Challenges and Learnings in Public Accounting

(07:30) Automation in Accounting: A Necessity

(10:02) Joining Rippling: Building from the Ground Up

(11:47) Balancing Controls and Growth in Startups

(14:52) Sponsor: NetSuite | Attio

(16:52) Putting On the Auditor's Hat

(18:24) What If There's No Buy-in from Management?

(21:02) Stepping into OpenAI and Embracing AI in Accounting

(24:12) Transforming Accounting with ChatGPT

(25:35) Real-World Applications and Success Stories

(26:29) Future of AI in Accounting

(29:44) OpenAI's Accounting Team and Processes

(30:02) Sponsor: Beehiiv | Brave

(33:12) Innovative Tools and Systems

(37:36) Advice for Future Accountants

(45:30) Addressing Fear of AI in Accounting

(47:41) Wrap

E9: An Insider's Guide After $2B of M&A with Serial CFO Steve Love of Sift, Dialpad, and Heap

Thu, 30 May 2024 07:00:00 -0000

In this conversation, Steve Love, a seasoned CFO with over $1 billion raised from VCs and $2 billion in M&A transaction experience, pulls back the curtain on high-stakes M&A. Love shares his insights from overseeing complex acquisitions like Heap's purchase of a complementary "session replay" company and Heap's eventual sale to ContentSquare. He candidly discusses navigating challenges, aligning stakeholders, prepping for diligence, and making strategic M&A decisions as a CFO. Whether you're a CFO, finance professional or simply M&A-curious, Love's tactics for evaluating targets, modeling forecasts, negotiating terms, and executing integrations provide a rare behind-the-scenes look at what it really takes to architect successful transactions.

🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj

RECOMMENDED PODCAST:

📈 ECON 102 W/ NOAH SMITH - Keeping econ entertaining - Noahpinion author Noah Smith and Erik Torenberg break down business news and politics every week.

Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH

Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812

SPONSORS:

NETSUITE

BEEHIIV

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BRAVE

---

LINKS:

https://sift.com/

X/SOCIAL:

@sashaorloff (Sasha)

@SteveLoveCFO (Steve)

TIMESTAMPS:

(00:00:00) Intro and preview

(00:01:24) Steve Love's impressive background

(00:02:39) Diving into M&A: When and why to acquire

(00:03:34) Case study: Heap's product acquisition

(00:05:17) Evaluating market players and integration challenges

(00:13:29) Integration and transition best practices

(00:17:43) Sponsor: NetSuite | Attio

(00:20:21) The biggest surprise after acquisition

(00:22:33) The first thing CFOs do after signing

(00:32:29) Sponsor: Beehiiv | Brave

(00:33:02) Negotiating severance packages

(00:37:34) Executing a sell-side transaction

(00:37:55) Handling market checks and bankers

(00:49:52) Differences between private and public company sales

(01:02:13) Biggest misconceptions about a CFO's role

(01:03:03) Wrap

E8: When Your Biggest Competitor Crashes, with Mercury CEO Immad Akhund

Thu, 23 May 2024 07:00:00 -0000

How do you navigate the tide turn when your competitor collapses during one of the biggest banking crises in recent history? In this conversation, Sasha Orloff sits down with Immad Akhund, founder and CEO of Mercury*. Immad pulls back the curtain on the chaos and critical decisions made when Silicon Valley Bank fell. From mobilizing an all-hands effort to rapidly onboard new customers to developing new product features virtually overnight to instill confidence, Immad provides an unvarnished look at crisis management and steadfast leadership during turbulent times. He also shares insights on Mercury's customer-first approach to building, how rising interest rates transformed their business model, and how he thinks about investing in new product initiatives by allocating internal resources like venture investments.

*Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust, Members FDIC.

🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj

---

SPONSOR:

Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine

---

Recommended Podcast: Company Breakdowns

Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. Profiled this season: Databricks, Reddit, Twilio, Copart + more.

Spotify: https://open.spotify.com/show/0epyYBAxLeF0PsNagdDJAJ

Apple: https://podcasts.apple.com/us/podcast/company-breakdowns/id1743119197

📈 ECON 102 W/ NOAH SMITH - Keeping econ entertaining - Noahpinion author Noah Smith and Erik Torenberg break down business news and politics every week.

Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH

Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812

---

LINKS:

https://mercury.com/

---

X/SOCIAL:

@sashaorloff (Sasha)

@Immad (Immad)

---

TIMESTAMPS:

(00:00) Preview

(01:15) Intro

(02:23) Immad’s Journey to founding Mercury and being a serial entrepreneur

(02:37) Immad’s learnings after founding three startups

(06:54) Learnings from being a YC partner and angel investor

(08:54) What gets Immad excited about investing

(10:17) Why Series A vs seed stage investing

(12:18) Building the banking solution

(13:49) The moment when Immad knew Mercury was the right thing

(16:12) How interest rates affect Mercury

(18:48) Silicon Valley Bank collapse and what was happening at Mercury

(23:50) SVB failed, why is Mercury safe?

(24:00) Mercury Vault’s inception and increasing FDIC insurance to 3 million

(25:56) Would Immad do anything differently going back to the SVB collapse?

(27:41) How Mercury’s team was able to remain calm and adapt

(29:21) Launching new products within a startup: product innovation

(31:12) Having a longterm mindset when launching new products

(33:49) Thinking about product launches internally like they’re startups

(36:37) Breadth vs depth in a market

(40:30) Something about Mercury a lot of people don’t know today

(43:50) Number one piece of advice for founders

(44:26) Wrap

E7: The Dealmaker’s Secrets: Steve McLaughlin on Crafting a Fundraising Story Worth $33B, CEO of FT Partners

Thu, 16 May 2024 07:00:00 -0000

In this conversation, Sasha Orloff sits down with Steve McLaughlin, CEO and Managing Partner of FT Partners. Steve provides an insider’s look into the high-stakes world of capital raising and dealmaking for high-growth private companies. From being Goldman Sachs’ Former Head of Fintech to founding FT Partners, a global fintech investment firm, McLaughlin shares his strategies for crafting compelling narratives that unlock massive fundraising rounds - like the $33 billion valuation for Revolut and a $100 million plus raise for Sam Altman’s Worldcoin. They dive deep into storytelling, the importance of product over marketing spend, founder red flags, and much more.

🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj

This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co

---

RECOMMENDED PODCAST:

📈 ECON 102 W/ NOAH SMITH - Keeping econ entertaining - Noahpinion author Noah Smith and Erik Torenberg break down business news and politics every week.

Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH

Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812

---

SPONSORS:

---

Recommended Podcast: Company Breakdowns

Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. First episode is on Rubrik - which just IPO'd. Coming up this season: Databricks, Reddit + more,

Spotify

Apple

---

LINKS:

https://ftpartners.com/

X/SOCIAL:

@sashaorloff (Sasha)

@FTPartners (Steve)

TIMESTAMPS:

(00:00:00) The art of storytelling in high-growth company valuations

(00:01:31) A capital whisperer's journey

(00:02:26) Inside FTPartners: Shaping the fintech universe

(00:04:33) The intricacies of capital raising and M&A

(00:07:39) Crafting the perfect capital raise story

(00:14:13) The complex world of investor networks

(00:16:41) Maximizing value beyond valuation

(00:19:05) A deep dive into successful storytelling and strategic selling

(00:22:57) The philosophy of business growth and valuation

(00:23:33) Understanding the founder's journey and ambitions

(00:24:32) The role of investment bankers in raising capital

(00:25:46) The importance of choosing the right banker

(00:28:17) Revolut's success story: A case study

(00:36:07) Strategic advice on growth vs. profitability

(00:39:01) Reflecting on capital raising experiences and red flags

(00:41:06) The evolution of FT Partners

(00:46:12) Closing thoughts and acknowledgements

E6: Behind the Scenes of General Catalyst: The VC Firm's Financial Operations with CFO, Mark Allen

Fri, 10 May 2024 07:00:00 -0000

Ever wondered what the financial operations look like when you have billions in AUM at a top-tier VC firm?

In this episode, Sasha sits down with Mark Allen, CFO at General Catalyst. Mark discusses the non-obvious complexities of managing billions in assets across hundreds of portfolio companies, from capital reserve strategies, geographical breakdowns, to reporting requirements. He shares candid insights on navigating intense moments like the Silicon Valley Bank collapse, tech innovations being adopted by VC firms, how being a fund’s CFO comprises two roles of being CFO of a fund and a firm, advice for CFOs coming to pitch at General Catalyst, and much more.

This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co

---

SPONSORS:

---

Recommended Podcast: Company Breakdowns

Spotify

Apple

📈 ECON 102 W/ NOAH SMITH - Keeping econ entertaining - Noahpinion author Noah Smith and Erik Torenberg break down business news and politics every week.

Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH

Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812

---

LINKS:

https://www.generalcatalyst.com/team/mark-allen

X/SOCIAL:

@sashaorloff (Sasha)

@generalcatalyst

TIMESTAMPS:

(00:00) Preview + Intro

(02:37) Mark Allen’s Journey to Being CFO of General Catalyst (GC)

(06:23) How the VC business model works

(08:44) Power law and reserves

(08:44) FP&A at a fund and capital reserve strategies

(11:20) Investment mix / geographical jurisdictions

(14:05) How GC maintains line of sight into their portfolio companies

(14:51) Sponsor: Attio

(17:04) Tools that Mark uses and revolutions in tools for CFOs

(19:12) Using AI for DDQs

(21:23) Inflection points in GC’s history

(24:19) Transition from hundreds of millions to billions of dollars in AUM

(26:01) Critical decision points for GC and Mark

(30:14) Sponsor: Turpentine

(30:58) Advice for CFOs on building trust with their leadership

(33:03) The importance of relationships as a CFO

(36:20) How General Catalyst’s work culture has changed after the pandemic

(39:18) Biggest misconceptions about being CFO at VC fund

(41:26) Advice for CFOs pitching to VCs

(42:26) Wrap

E5: Bringing Fun Back to Finance: Redesigning Business Modelling with Runway’s Siqi Chen, CEO

Thu, 02 May 2024 07:00:00 -0000

Get an inside look at Runway - the visually stunning finance platform that's breaking conventions and captivating users with its approach to making finance fun again.

In this interview, founder and CEO Siqi Chen shares the arduous 3-year journey of iterating on the product from its inception during a meeting with the a16z team, working alongside early design partners, and the key inflection points that transformed Runway into what it is today. He emphasizes the importance of storytelling, having the data from different company functions centralized and in communication with each other, and fostering a culture where work, and finance in particular, is genuinely fun. Whether you're in finance or appreciate great product design, this is a must-watch episode.

This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co

---

SPONSORS:

---

Recommended Podcast: Company Breakdowns

Spotify

Apple

📈 ECON 102 W/ NOAH SMITH - Keeping econ entertaining - Noahpinion author Noah Smith and Erik Torenberg break down business news and politics every week.

Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH

Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812

---

LINKS MENTIONED:

Runway Financial: https://runway.com/

Sandbox VR: https://sandboxvr.com/

X/SOCIAL:

@sashaorloff (Sasha)

@blader (Siqi)

@runwayco (Runway)

TIMESTAMPS:

(00:00) Introduction to Runway and Siqi Chen

(01:30) Background and Inspiration for Runway

(08:25) Challenges and Pivot during COVID-19

(12:29) Raising Capital and Product Iteration

(14:57) Sponsor: Attio

(16:25) Balancing Feature Parity and Novelty

(17:30) arly Design Partners and Customers

(19:36) Building an Audience and Storytelling

(23:01) Mission and Vision of Runway

(26:13) Convincing Users to Leave Excel

(38:05) Demo of Runway

(41:45) Development and Design Process

(42:49) Product Features and Future Plans

(44:43) Company Culture and Team

(46:45) Future of Runway

E4: Can Turning Down a Huge Upround Lead to a Greater Outcome? FloQast CFO Razzak Jallow Proves It Can

Thu, 25 Apr 2024 07:00:00 -0000

In this episode, Sasha sits down with Razzak Jallow, CFO at FloQast, to discuss the evolving role of the modern CFO as a strategic partner across the organization. They dive into how he builds trust with the CEO, his approach to fostering product innovation responsibly, and why he turned down a financing round that would have doubled FloQast's valuation. Razzak also offers advice for aspiring CFOs on evaluating their first CFO role, skills like "precision Q&A", and hiring great talent

This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co

---

SPONSORS:

---

Recommended Podcast: Company Breakdowns

Spotify

Apple

📈 ECON 102 W/ NOAH SMITH - Keeping econ entertaining - Noahpinion author Noah Smith and Erik Torenberg break down business news and politics every week.

Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH

Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812

---

X/Twitter:

@sashaorloff (Sasha)

@floqast (Floqast)

@turpentinemedia

TIMESTAMPS:

(00:00) Preview

(02:22) How Razzak would describe the role of CFO

(02:55) Razzak’s superpowers: hiring and working with different people

(04:28) Building trust with different colleagues across different functions and cultures

(06:31) How to be the office of “how to” rather than “no”

(08:47) Having an effective discussion when there isn’t a right answer

(11:47) Changing the culture from being a no shop to a let’s be a partner shop

(14:26) Precision Q&A

(15:24) Sponsor: Attio

(17:22) What is FloQast

(19:34) Taking on the first CFO role and evaluating fit

(21:45) Deciding not to raise at a higher valuation and why

(25:20) Having a cash war chest

(27:02) Balancing product innovation and financial discipline as CFO

(30:00) The early milestones in a new product that unlock more capital

(31:32) Getting alignment on what payback on a new product should be

(38:16) Advice to future CFOs and an underrated skill people should work on more

(41:39) Building trust with your CEO

(45:27) Wrap

E3: Chris Bakke on Negotiating with Elon Musk and Setting Up An M&A from Day One (3x exits)

Thu, 18 Apr 2024 07:00:00 -0000

Ever wonder what it's like to get a call from Elon Musk, wanting to buy your company?

In this episode, Sasha sits down with serial entrepreneur Chris Bakke to find out. Chris is the co-founder behind several successful startups, including Laskie, which was acquired by Elon Musk's X, and Interviewed, acquired by Indeed. Chris shares insights on: building a content-driven growth strategy as a founder that's led to his 200k+ follower base, navigating the M&A process and negotiating a deal directly with Musk, transitioning from founder to his current role in building X's job search platform, and much more.

This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co

---

SPONSORS:

---

Recommended Podcast: Company Breakdowns

Spotify

Apple

📈 ECON 102 W/ NOAH SMITH - Keeping econ entertaining - Noahpinion author Noah Smith and Erik Torenberg break down business news and politics every week.

Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH

Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812

---

X/Twitter:

@sashaorloff (Sasha)

@chrisjbakke (Chris)

@turpentinemedia

TIMESTAMPS:

(00:00) Chris Bakke Intro

(02:49) Laskie and what got Chris excited about it

(04:03) Content as a growth strategy

(07:29) How Chris found his content voice

(12:50) What’s the next thing in content

(19:32) Best practices as a founder to set up M&A as a future path

(24:36) Getting Indeed as a partner, investor, and acquirer of Interviewed

(26:51) Laskie’s M&A Story

(29:13) How Chris ended up talking to Elon about Laskie and Twitter recruiting

(35:11) What Chris would’ve done differently at Indeed

(37:12) Common mistakes and misconceptions during the M&A process

(45:00) Chris’ most memorable X post, not of his own

(46:22) Wrap

E2: When COVID Hits and You are CFO at Instacart with Sagar Sanghvi

Thu, 11 Apr 2024 07:00:00 -0000

In this episode, Sasha sits down with Sagar Sanghvi, Current Partner at Accel and former CFO at Instacart. They discuss how Sagar drove the change in financial culture at Instacart and adapted rapidly to Whole Food’s acquisition by Amazon, scaling Instacart during the COVID pandemic, the balance between growth at all costs and unit economics, Sagar’s transition from CFO at Instacart to being Partner at the venture firm Accel, and much more.

This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co

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SPONSORS:

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Recommended Podcast: Company Breakdowns

Spotify

Apple

📈 ECON 102 W/ NOAH SMITH - Keeping econ entertaining - Noahpinion author Noah Smith and Erik Torenberg break down business news and politics every week.

Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH

Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812

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LINKS:

https://www.accel.com/people/sagar-sanghvi

X/SOCIAL:

@sashaorloff (Sasha)

@spsanghvi4 (Sagar)

@turpentinemedia

CONTACT:

sps@accel.com

TIMESTAMPS:

(00:00) Preview and Intro

(02:30) Sagar's time at Instacart

(04:29) Training from Goldman and KKR

(06:58) When to transition to unit economic focus instead of growth at all costs

(08:31) The process of changing a financial culture at a company

(10:57) Advice for CFOs in driving culture with a founder where financial discipline is not present yet

(13:39) Sponsor: Attio

(14:55) How do you bring colleagues from other functions into alignment

(17:22) Amazon's acquisition of Whole Foods and Instacart's internal dynamics

(20:17) Signs that Amazon's acquisition of Whole Foods was a positive infection for Instacart

(21:43) Instacart's wartime and tactical parts of Sagar's job during wartimes

(24:04) Size of Instacart's finance team

(25:10) What Sagar would have done differently in response to the acquisition

(27:54) Sagar's VP of Strategy transition to CFO at Instacart

(30:13) Balancing growth versus profitability

(36:27) Instacart during COVID and lockdown

(40:41) Sagar's transition to Accel and VC

(44:59) Advice for CFOs positioning themselves to VC

(47:34) What gets Sagar excited about a deal?

(49:58) Wrap

E1: Making Decisions in Hyper Growth with Former WeWork Strategic CFO Casey Woo

Mon, 08 Apr 2024 07:00:00 -0000

In the debut episode of Turpentine Finance, host Sasha Orloff sits down with Casey Woo, Founder of Operator's Guild, GP at Fog Ventures, and WeWork's former Global Head of Strategic Finance. They unpack the value of being a business-first CFO, the lessons learned from working in pressure-cooker settings like WeWork, how CEOs can evaluate CFOs (and vice versa), and frameworks for being a career 'specialist generalist'.

This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co

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SPONSORS:

---

Recommended Podcast:

Company Breakdowns

Spotify

Apple

📈 ECON 102 W/ NOAH SMITH

Keeping econ entertaining - Noahpinion author Noah Smith and Erik Torenberg break down business news and politics every week.

Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH

Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812