"Turpentine Finance" with Sasha Orloff | Startup Finance, Leadership, CFO Strategy Turpentine

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

BEEHIIV
🐝 Head to Beehiiv, the newsletter platform built for growth, to power your own. Connect with premium brands, scale your audience, and deliver a beautiful UX that stands out in an inbox. Go to https://beehiiv.com and use code “MOZ” for 20% off your first three months

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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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.
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X/SOCIAL:
https://twitter.com/sashaorloff (Sasha)
https://twitter.com/heysowmya (Sowmya)
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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

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.

SPONSORS:
📊 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
📈 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.

BEEHIIV
🐝 Power your newsletter with Beehiiv, the newsletter platform built for growth. Connect with premium brands, scale your audience, and deliver a beautiful UX that stands out in an inbox. Head to https://Beehiiv.com and use code "MOZ" for 20% off your first three months

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.
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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
(00:08:20) Operational considerations post-acquisition
(00:10:22) The role of the CFO in M&A
(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
(00:24:34) Acquihire vs. product acquisition
(00:32:29) Sponsor: Beehiiv | Brave
(00:33:02) Negotiating severance packages
(00:35:02) Pre-negotiating terms at hiring
(00:37:34) Executing a sell-side transaction
(00:37:55) Handling market checks and bankers
(00:39:26) Preparing for M&A discussions
(00:43:10) Navigating first meetings with acquiring CFOs
(00:45:01) Challenges in cross-border acquisitions
(00:49:52) Differences between private and public company sales
(00:53:08) Maximizing buyer interest and value
(00:55:23) Lessons from previous M&A experiences
(00:58:36) Career reflections and advice for aspiring CFOs
(01:02:13) Biggest misconceptions about a CFO's role
(01:03:03) Wrap

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.
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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
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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
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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.

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LINKS:
https://mercury.com/

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X/SOCIAL:
@sashaorloff (Sasha)
@Immad (Immad)

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TIMESTAMPS:

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.

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

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SPONSORS:
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. First episode is on Rubrik - which just IPO'd. Coming up this season: Databricks, Reddit + more,
Spotify
Apple
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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.
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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

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

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SPONSORS:
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. First episode is on Rubrik - which just IPO'd. Coming up this season: Databricks, Reddit + more,
Spotify
Apple
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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.

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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

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

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SPONSORS:
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. First episode is on Rubrik - which just IPO'd. Coming up this season: Databricks, Reddit + more,
Spotify
Apple

---
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.

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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