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

May 30 2024 50 mins 30

A podcast where Sasha Orloff talks to CFOs, founders, and finance leaders at the best tech companies about what it takes to architect success. Our guests speak candidly about big business inflections, market curveballs and how they approach decision-making to tease out tactics and mental models you can use for when the pressure is on. You’ll hear stories from Instacart, Mercury, OpenAI, Andreessen Horowitz, Netflix, Runway, and more. Topics frequently touched upon M&A, Market Downturn, Macro, PMF, Fundraising, Financial Forecasting, Headcount, Equity.

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

May 30 2024 64 mins  
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 challe

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

May 23 2024 47 mins  
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 custom

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

May 16 2024 48 mins  
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 f

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

May 10 2024 44 mins  
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

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

May 02 2024 49 mins  
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 i

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

Apr 25 2024 46 mins  
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 f

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

Apr 18 2024 47 mins  
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 stra

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

Apr 11 2024 50 mins  
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 Inst

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

Apr 08 2024 50 mins  
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 be