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

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

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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 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

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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/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

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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/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
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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: 
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
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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:
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

Today is a special episode where CJ Gustafson and Sasha Orloff (3x founder and current CEO of Puzzle) go deep on the CFO-CEO mindsets…and talk podcasting. They cover: highlights and memorable advice from CJ’s 50+ interviews on this feed, how to have impact as a CFO & CEO, the challenges of building finance software, each host’s biggest mistakes, and how to make a successful podcast. Turpentine Finance hosted by Sasha Orloff will debut later this week and this season will feature firsthand stories from guests about the greatest inflection moments in the history of Mercury, OpenAI, Andressen Horowitz, Netflix, Runway, and more.

📅 Turpentine Finance hosted by Sasha Orloff debuts on 4/4/24.

CJ's Run The Numbers continues with great new content over on:
Apple: https://podcasts.apple.com/us/podcast/run-the-numbers/id1723787140
Spotify: https://open.spotify.com/show/0zQCkklNnVgMD364kCW5SV
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SPONSORS:

Maxio is the only billing and financial operations platform that was purpose built for B2B SaaS. They're helping SaaS finance teams automate billing and revenue recognition, manage collections and payments, and put together investor grade reporting packages. 🚀 Request a demo at www.maxio.com/runthenumbers for 10% off your first year.

NetSuite provides financial software for all your business needs. More than 37,000 thousand companies have already upgraded to NetSuite, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you're looking for an ERP platform ✅ NetSuite: https://netsuite.com/metrics and get a customized KPI checklist.

Thoropass provides complete compliance management, continuous monitoring, and security audits through intuitive software and expert guidance – allowing you to do business with confidence. Learn more: https://bit.ly/Thoropass 🔒

Tropic is the next-generation Procurement Platform that’s helping modern CFOs take control of their budgets and bottom line. By combining approval workflows, supplier management, and pricing benchmarks all in one place, Tropic makes savings opportunities easy to find and act on. 🌴 Visit www.tropicapp.io/metrics to learn how.

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FOLLOW US ON X:
@sashaorloff (Sasha)
@cjgustafson222 (CJ)
@turpentinemedia

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TIMESTAMPS
(00:00) A Hilarious Start
(00:33) Starting a Podcast
(02:25) Exploring the CEO-CFO Relationship
(04:09) Two Superpowers of CFOs
(07:52) From Content Creation to Building Run the Numbers
(11:11) Sponsor: Maxio | NetSuite
(13:41) Lessons CJ Learned from Episode 1 Onwards
(17:37) Creating Content and Finding the Right Audience
(22:28) Sports, Seasonality and Unique Business Models
(28:44) Challenges of Building Puzzle.io
(31:46) AI Revolution in Finance
(35:29) Sponsor: Thoropass | Tropic
(38:00) Building the Turpentine Finance Podcast
(40:23) Sasha's Career Mess-Up
(46:50) Building Something Bigger (and Still Have a Bit of Hair)
(53:40) Sasha's Frameworks for Managing Time and Impact
(57:39) Spinning Your Own Thing and Betting on Yourself
(1:02:04): Wrap