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 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

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 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

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 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

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 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

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 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

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 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

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 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

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 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

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 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

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. --

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. —

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. —

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 —

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 — 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:

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 — 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:

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 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:

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 --

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 --

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.

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.

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: 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. 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

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.

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.

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.

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.

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:

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:

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/ RECOMMENDED PODCAST Founder, entrepreneur, and best-selling author of The Lean Startup Eric Ries discusses how to build profitable companies for the long-term benefit of society. Ries talks with world-class technologists, thought leaders, and executives working to create a new ecosystem of trustworthy organizations with limitless potential for growth and a deep commitment to purpose. Together, they uncover the tools and methods to ensure the next generation of companies are designed to maximize human flourishing for generations. Guests have included founders from Facebook, LinkedIn, Zapier, TaskRabbit, and many others. Listen here at: https://www.ericriesshow.com/ SPONSORS: RIPPLING SPEND: 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 rippling.com/spend for a free demo and one month free trial. 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: 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 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 (00:36:13) - Types of teams LTSE likes to work with (00:42:36) - Challenges and questions companies ask behind the scenes (00:50:36) - Brief mention of companies listed on LTSE (00:53:12) - Advice for CEOs and CFOs thinking about going public (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

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. --

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.  --

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. --

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. --

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.

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.

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.

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

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

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:

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. --- 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 --- 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. --- LINKS: https://mercury.com/ --- X/SOCIAL: @sashaorloff (Sasha) @Immad (Immad) --- 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 --- 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. --- 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 --- 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. --- 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 --- 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. --- 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 --- 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 --- 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 --- 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 --- 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) @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 --- 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. --- 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 --- 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. --- 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 --- X/Twitter @sashaorloff (Sasha) @caseyswoo (Casey) @FogVentures (Fog) @turpentinemedia --- 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.

In this episode, CJ discusses the business of global payments and B2B fintech with Camilla Matias Morais, COO of Brex. Camilla came up in the FP&A world and is a stellar guide to Brex's strategic bets and moats. Also covered is how she balances the COO role of risk management and company strategy while also being in the weeds with customer feedback. — **PSA: Run The Numbers has a new Spotify and Apple show link. Follow the links to subscribe and ensure you'll never miss an episode Apple: https://podcasts.apple.com/us/podcast/run-the-numbers/id1723787140 Spotify: https://open.spotify.com/show/0zQCkklNnVgMD364kCW5SV — 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.

In this episode, CJ talks with the original duo of the HR Heretics podcast, Kelli Dragovich and Nolan Church about tech layoffs in 2024. Kelli and Nolan hold no punches and give straight answers to tough questions on layoffs, the job market, and employment best practices. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a one-of-a-kind flexible financing program until April 15th, 2024. — PSA: Run The Numbers has a new Spotify and Apple show link. Follow the links to subscribe and ensure you'll never miss an episode Apple: https://podcasts.apple.com/us/podcast/run-the-numbers/id1723787140 Spotify: https://open.spotify.com/show/0zQCkklNnVgMD364kCW5SV — RECOMMENDED PODCAST: HR Heretics Join Nolan Church and Kelli Dragovich for unfiltered conversations with people leaders, investors, and CEOS. Dive deep into the kind of leadership-level strategy that often happens behind closed doors.  Substack: https://hrheretics.substack.com/ Spotify: https://open.spotify.com/show/1WML9AfadzaH9WCR4HHqbZ — 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.

In this episode CJ is joined by Fred Havemeyer, a leading sell-side equity analyst from Macquarie specializing in AI and software research within the US, delve deep into AI's impact on the near term role of a CFO. Fred offers an unparalleled analysis of how to quantify productivity gains with AI, the difference between the metrics the sell side uses versus operators and their day to day models. They also cover what company valuations are an art and a science. — PSA: Run The Numbers has a new Spotify and Apple show link. Follow the links to subscribe and ensure you'll never miss an episode Apple: https://podcasts.apple.com/us/podcast/run-the-numbers/id1723787140 Spotify: https://open.spotify.com/show/0zQCkklNnVgMD364kCW5SV — 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.

Todd Rakow, CFO of Gladly joins CJ for this deep dive into usage-based revenue models, strategic finance leadership, and the complexities of managing growth and headcount in line with ARR. Todd shares tons of tactical insights, including building out the usage-based model, forecasting customer usage patterns, commissioning sales reps, and teaching your teams to distinguish between reoccurring and recurring revenue. If you're looking for an ERP head to NetSuite: https://netsuite.com/metrics and get a one-of-a-kind flexible financing program until April 15th, 2024. — PSA: Run The Numbers has a new Spotify and Apple show link. Follow the links to subscribe and ensure you'll never miss an episode Apple: https://podcasts.apple.com/us/podcast/run-the-numbers/id1723787140 Spotify: https://open.spotify.com/show/0zQCkklNnVgMD364kCW5SV — 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.