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

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

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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. 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

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

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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.

---

X/Twitter:
@sashaorloff (Sasha)
@floqast (Floqast)
@turpentinemedia

TIMESTAMPS:

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

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

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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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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

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
---

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: 
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

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
---
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:
Operator's Guild: https://operators-guild.com/
Fog Ventures: https://www.fog.ventures/
Casey's Linkedin: https://www.linkedin.com/in/caseywoo
Casey's contact: hello@operators-guild.com
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X/Twitter
@sashaorloff (Sasha)
@caseyswoo (Casey)
@FogVentures (Fog)
@turpentinemedia
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TIMESTAMPS:
(00:00) Preview
(02:00) Life as a banker
(04:06) Story following numbers or numbers following story
(04:39)How banking prepared Casey for working in a startup's finance team
(07:00) Deciding that working in a startup is a right fit
(09:10)Hiring a CFO
(11:20) Advice for bankers transitioning to operating roles
(12:41) First things to accomplish when stepping into a role
(14:05) Sponsor: Attio
(14:52) Interview question to see if a founder takes finance seriously
(16:16) Advice for CFOs to change the dynamic that finance has in the company
(18:08)Casey's time at WeWork as CFO for Western US and Canada
(22:00) Casey's experience being Global Head of Strategic Finance at WeWork
(29:40 Advice for founders in dealing with different growth or recessive cycles
(32:57) Probabilities
(34:00) Time spent on fundraising vs supporting the founder as a CFO
(35:26) Operator's Guild and Generalists
(42:00) How can operators thrive in a transition role
(47:28) The number one piece of advice Casey would give to CFOs
(49:38) Wrap