"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech

In this episode, Sasha Orloff sits down with Luke Frye, founder of LukeFrye.co, to trace his decade-long journey through foundational fintech pioneers like Bench and Pilot and explore how AI is shifting the accountant's role from manual data entry to "architecting" financial systems and human-centric advisory. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/lukefrye/ https://lukefrye.co/ -- X/SOCIAL: @LukeFrye (Luke) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:37) Intro (02:14) From Wyoming To Techstars (05:49) Bench origin story (07:11) Automating accounting tension (09:20) Bench growth playbook (11:06) Early sales and scale (14:28) Sponsors: Notion | Puzzle (15:53) Bench cracks and incentives (18:59) Tax experiment trainwreck (21:38) Solo practice to Pilot (23:51) Pilot tech stack shift (24:48) Sales ops balance (26:36) From Pilot to Rivet (27:18) Why Puzzle mattered (29:17) Modern tax software gap (31:12) Automation limits today (34:33) AI makes us human (37:06) Where firms should start (39:19) Vision values planning (42:43) Future firm architect (44:57) Wrap

In this episode, Sasha Orloff speaks with Greg Capitolo, Co-founder and Partner at Attivo Partner, to discuss how fractional finance teams are transitioning from manual bookkeeping to AI-driven advisory roles, emphasizing the shift toward "real-time data-driven decision making" over traditional month-end closes. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/gregcapitolo/ http://www.attivopartners.com -- X/SOCIAL: @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:39) Intro (02:07) Meet Greg Capitolo of Attivo Partner (03:26) Who Attivo serves (04:07) Why VCs recommend (06:40) Founder trigger points (08:50) AI outlook (10:59) AI boosts advisory (15:19) Creating 10x accountants (19:51) Sponsors: Notion | Puzzle (21:14) Pricing and billing shift (23:41) Choosing AI tools (27:06) Human in the loop (30:22) Accounting needs accountants (32:09) Real time data (35:14) Tool evaluation framework (38:54) Growth mindset future (40:56) Wrap

In this episode, Sasha Orloff speaks with Tarek Alaruri, CEO and Co-founder of Stuut, about raising a Series A from Andreessen Horowitz to build an AI-powered accounts receivable platform that automates the entire AR function—from credit and collections to cash application and disputes—delivering a 40% reduction in DSO in the first six months compared to the 3% improvement from legacy software, while implementing in just 3.6 days for mid-market and Fortune 100 companies. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/tarekalaruri/ https://www.stuut.ai/ -- X/SOCIAL: @TAlaruri (Tarek) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:42) Intro (01:25) Interview with Tarek Alaruri, CEO of Stuut (01:50) Problem with traditional accounts receivable (03:31) How AI is transforming accounts receivable (05:39) Stuut's mission and impact (08:17) Future of AI in finance (09:55) Customer experience and AI solutions (11:35) Evolution of AI and business processes (14:04) Sponsors: Notion | Puzzle (15:31) Eliminating clicks with Stuut (17:07) AI in B2B transactions (21:56) Role of AR teams today and tomorrow (23:38) Fundraising insights and strategies (30:46) Building enterprise AI and future outlook (35:12) Wrap

In this episode, Sasha Orloff sits down with Sam Ross, co-founder and CEO of Numeral and former product leader at Teespring and Airbnb, about raising Series B funding from Mayfield (following Benchmark's Series A and Uncork's seed) to build what he calls "the most boring AI company"—an end-to-end sales tax automation platform that uses AI to eliminate the manual burden of multi-state and international tax compliance for e-commerce and SaaS businesses, transforming a traditionally services-heavy industry into a fully automated solution that handles everything from nexus analysis and registration to filings and government correspondence. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/sambross/ https://www.numeral.com -- X/SOCIAL: @SpamRoss (Sam) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:49) Intro (01:22) Guest Introduction: Sam Ross (01:44) Most boring AI company (03:54) AI and sales tax (06:08) Origin story and early challenges (10:56) Building the business and first customers (13:14) Sponsors: Notion | Puzzle (14:36) Sales tax compliance and solutions (17:12) Automating mail and customer engagement (18:24) E-commerce and tax compliance challenges (19:40) Marketplace tax exposure issues (22:15) Government complexities and physical mail (23:54) Founding story and funding journey (30:55) AI innovations in tax compliance (33:11) Future of AI and browser automation (34:33) Wrap

In this episode, Sasha Orloff speaks with Usman Gul, founder and CEO of Metal, about building an AI-driven operating system for fundraising backed by Y Combinator and Andreessen Horowitz that helps founders avoid wasting 80% of their investor meetings by using data-driven insights to identify the most likely investors based on historical funding patterns, industry benchmarks, and relationship intelligence across over 500,000 venture rounds. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/gulsf/ http://www.metal.so -- X/SOCIAL: @usmangul (Usman) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:44) Intro (01:28) Meet Usman Gul from Metal (01:59) Genesis of Metal (04:32) Metal's AI-driven fundraising solutions (08:08) Common fundraising mistakes and solutions (13:24) Sponsors: Notion | Puzzle (14:15) Importance of modern tools for startups (21:40) Metal manifesto (24:35) Key indicators for successful fundraising (25:53) Telling the right story to investors (26:44) Challenges and insights from previous ventures (27:13) Evolution of investor targeting (28:38) Predictive intelligence and the future of Metal (30:41) Current state of fundraising tools (36:53) Building Metal with minimal capital (39:19) Advice for founders on fundraising (47:29) Wrap

In this episode, Sasha Orloff speaks with Renato Villanueva, Founder and CEO of Parallel, about his journey from finance professional at Divvy to raising $2.4 million from Bain Capital and K5 Tokyo Black for an AI-powered FP&A platform that helps founders model financial scenarios and make confident growth decisions. Renato shares lessons on building products founders are passionate about rather than forced wedges, nurturing investor relationships, and how Parallel's approach has enabled customers to achieve significant growth—including one company that scaled from planning one sales hire to four, ultimately raising one of Utah's biggest Series A rounds. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: ⁠https://www.linkedin.com/in/villanuevar/⁠ https://www.getparallel.com/ -- X/SOCIAL: @_renatov (Renato) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (01:24) Intro (02:09) Meet Renado Villanueva (02:38) Renado's journey to founding Parallel (04:02) Moment of decision (04:45) Building the deck and quitting the job (09:20) Challenges and insights in fundraising (11:05) What Parallel actually does (14:24) Sponsors: Notion | Puzzle (15:49) Parallel’s target sweet spot (16:49) Common mistakes founders make (19:30) AI's role in finance decision-making (20:15) Balancing flexibility and opinion in software (23:11) Who should use Parallel? (25:06) Excel vs. Parallel: Finding the right balance (27:06) Evolution of FP&A tools (31:24) Lessons learned from building Parallel (35:34) Building and trusting a team (38:31) Future of Parallel (39:47) Wrap

In this episode, Sasha Orloff talks with Yogi Goel, Co-founder and CEO of Maxima, about raising $41 million from Kleiner Perkins and RedPoint Ventures to build an agentic AI platform for enterprise accounting that automates journal entries, reconciliations, and variance analysis for complex companies, helping them close their books 2-3 days faster with 98% automation while strengthening SOX controls and freeing accountants from mundane tasks. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/yogi-goel/ https://www.maxima.ai/ -- X/SOCIAL: @maxima_dot_ai (Maxima) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:50) Intro (01:34) Introducing Yogi Goel and Maxima (02:08) Problem with traditional accounting (04:50) Birth of Maxima (07:03) Maxima's solutions and innovations (11:19) Sponsors: Notion | Puzzle (12:43) Customer success stories (25:08) Future of accounting with AI (27:10) Fundraising and growth (29:53) Advice for founders and CFOs (34:15) Embracing AI: Overcoming fear and finding solutions (35:56) Getting in touch with Maxima (36:17) Story behind the name 'Maxima' (37:01) Wrap

In this episode, Sasha Orloff sits down with Dan Westgarth, COO of Deel, to explore how the company scaled to 37,000 customers, processes $22B in payroll, and recently raised a $300M Series E to power global hiring in 150 countries. They dive into the future of back-office automation, including real-time payroll, AI-driven operations, and the push toward a unified, seamless global HR and accounting stack. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/dan-westgarth-710650a4/ https://www.deel.com/ -- X/SOCIAL: @DanWestgarth (Dan) @deel (Deel) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:44) Introduction to Tech Finance (01:25) Meet Dan Westgarth, COO of Deel (02:18) Dan's journey with Revolut (06:22) Building Deel's global infrastructure (08:33) Managing global operations (12:06) Expanding Deel's services (19:56) Importance of consolidation (21:15) Sponsors: Notion | Puzzle (22:55) Common mistakes startups make (24:09) Onboarding and implementation challenges (25:46) Customer engagement and feedback (28:23) Recruiting and hiring strategies (31:27) Future of accounting and payroll (40:53) Real-time payroll processing (44:09) Wrap

In this episode, Sasha Orloff talks with Nick Abouzeid, Co-founder and CEO of Rivet, about raising venture capital from XYZ, Haystack, and other angels to build a modern tax and accounting firm that serves 600+ category-defining companies like Cursor by combining world-class tax practitioners with custom-built software infrastructure, delivering premium responsive service while challenging the traditional accounting firm model of unresponsive service and outdated technology. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: https://www.rivet.tax https://www.linkedin.com/in/nickabouzeid/ -- X/SOCIAL: @nickabouzeid (Nick) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:36) Intro (01:21) Meet Nick Abouzeid, CEO of Rivet (01:57) Rivet unique approach to tax services (02:52) Challenges in the tax preparation market (06:59) Human element in AI-powered tax services (09:33) Journey to venture capital (14:29) Sponsors: Notion | Puzzle (15:54) Scaling and surprises in building Rivet (18:23) Open roles and team dynamics (19:00) Feedback and roadmap development (19:24) International hiring and cost efficiency (20:40) Data integration challenges (21:23) Future of AI in accounting (22:58) Complexity in tax code and software (23:30) Human expertise vs. AI (32:23) Pricing models in tax preparation (34:26) Client success stories (36:29) Looking forward: New hires and future plans (37:16) Wrap

In this episode, Sasha Orloff sits down with Blake Hutchison, CEO of Flippa, to discuss the launch of Lauren AI—Flippa’s new AI tool transforming how online businesses are bought and sold. They explore how Lauren AI uses proprietary data and machine learning to enhance deal sourcing, automate buyer outreach, and streamline deal structuring. The conversation also dives into how AI is reshaping small business M&A, making exits and acquisitions more accessible, efficient, and competitive for entrepreneurs worldwide. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: https://flippa.com/product/dealsourcing/ https://www.linkedin.com/in/blakehutchison -- X/SOCIAL: @Flippa (Flippa) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:32) Intro (01:01) Interview with Blake Hutchison, CEO of Flippa (01:45) Introducing Lauren AI (02:15) How Lauren AI Enhances deal sourcing (07:05) Real-life example of Lauren AI in action (13:08) Sponsors: Notion | Puzzle (14:35) Matching engine and AI capabilities (17:38) Buyer experience and mandate creation (19:21) Lauren AI: Enhancing buyer profiles (21:33) Outreach and CRM integration (23:59) AI's role in M&A processes (28:33) Leveling the playing field for small buyers (31:11) Fair pricing and exit readiness (37:04) Wrap

In this episode, Sasha Orloff sits down with Jason Mok, VP & GM of Startups at Brex, about the company's evolution from credit cards to a comprehensive financial platform and their new partnership with Puzzle to offer "one-click accounting" that automatically sets up bookkeeping for startups during Brex onboarding, eliminating the friction that typically delays founders from getting proper financial infrastructure in place from day one. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/jasonmok/ https://www.brex.com/ -- X/SOCIAL: @jasonmok (Jason) @brexHQ (Brex) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:50) Intro (01:18) Live from Brex offices with Jason Mock (02:19) Early days of Brex and startup credit challenges (04:20) Silicon Valley bank's role in the startup ecosystem (12:26) From SVB to Andreessen Horowitz (18:50) Sponsors: Notion | Puzzle (20:13) Bridging the knowledge gap for first-time founders (22:48) Joining Brex during a time of change (28:02) Starting at Brex: Initial goals and challenges (28:52) Evolving role and team growth (29:39) Bespoke go-to-market strategies (32:08) Defining startups at Brex (36:54) Importance of accounting for startups (42:25) Introducing one-click accounting (46:52) Partnerships and future vision (55:13) Wrap

In this episode, Sasha Orloff talks with Joe Faris, founder of Accountalent, about his four decades of helping over 5,000 startups navigate tax and accounting challenges, covering critical founder lessons from 83B elections and R&D tax credits to payroll compliance and bookkeeping best practices that can save startups from costly mistakes and penalties. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/farisjoe/ https://accountalent.com/ -- X/SOCIAL: @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:55) Intro (01:24) Meet Joe Ferris: Startup tax expert (03:24) Joe's journey: From Shell oil to startups (06:46) Birth of Accountalent (09:14) Navigating the financial crisis (13:32) Adventures in IPOs and legal battles (19:33) Sponsors: Notion | Puzzle (21:18) Lessons for founders: Payroll pitfalls (23:21) Introduction to payroll medic (23:39) Understanding tax compliance for startups (26:37) Importance of bookkeeping (27:55) Unbook keeper for founders (29:08) Setting up and managing bookkeeping systems (35:44) Role of RD tax credits (38:32) Lessons learned from working with startups (39:51) Impact of good accounting and tax strategy (42:29) Wrap

In this episode, Sasha Orloff talks with Josh Wymer, Co-founder and CEO of Central HQ, about raising $8.6 million from First Round Capital and Y Combinator to build an AI-first back office solution that eliminates business compliance tasks through Slack-based automation, helping startups handle payroll, taxes, and HR without the administrative burden that typically comes with traditional software. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: ⁠⁠https://www.linkedin.com/in/joshwymer/ https://centralhq.com/ -- X/SOCIAL: @jbwyme (Josh) @CentralHQX (Central HQ) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (01:03) Intro (01:46) The unavoidable hassles (02:20) Meet Josh Wymer: The mission to eliminate business BS (02:57) Complexity of payroll and compliance (04:48) Central’s vision: Simplifying the back office (07:19) Challenges and innovations in payroll solutions (10:10) Sponsors: Notion | Puzzle (11:35) Future of AI in business operations (18:42) Power of LLMs and AI in streamlining tasks (21:42) Origin of the tagline (23:41) Investor reactions and brand strategy (24:36) Challenges in a competitive market (25:32) Focusing on founders and SMBs (28:51) Learning and iterating as a startup (33:21) Misunderstandings and common mistakes (36:44) Future of startups and SMBs (38:42) Wrap

In this episode, Sasha Orloff talks with Ben Taylor, CEO & Co-founder of SoftLedger, about bootstrapping a modern, API-first general ledger that helps finance teams manage multi-entity businesses beyond QuickBooks without the complexity of Netsuite. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: ⁠https://www.linkedin.com/in/bentaylor8/ ⁠https://softledger.com -- X/SOCIAL: @SoftLedger (SoftLedger) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:40) Intro (01:09) Meet Ben Taylor, CEO & Co-founder of SoftLedger (02:36) Origin story of SoftLedger (03:11) Target market and unique selling points (07:14) Evolution of the accounting software market (08:21) AI in accounting: Opportunities and challenges (11:08) Sponsors: Notion | Puzzle (12:31) SoftLedger's approach to AI integration (17:34) Choosing the right accounting software for complex enterprises (19:16) Customer success stories: Eco G energy (22:31) Challenges and surprises in building accounting software (26:58) Importance of multi-entity consolidation (31:53) Fundraising journey and efficient growth (34:16) Future plans and market expansion (37:03) Wrap

In this episode, Sasha Orloff and Alex Lee, Co-founder & CEO of Truewind, to discuss how his company is transforming accounting with AI-powered automation—streamlining tasks like data reconciliation and deposit matching from hours to minutes. They explore Truewind’s journey, recent funding led by Thomson Reuters and Row Capital, and the future of accounting through AI, autonomous agents, and customer-centric innovation. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/alexlee611/ https://www.truewind.ai/ -- X/SOCIAL: @AlexLee611 (Alex) @truewindai (Truewind) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:28) Intro (01:07) Guest Introduction: Alex Lee from Truewind (02:27) Origin of Truewind (06:18) Impact of AI on accounting (08:24) Adoption of AI in accounting (09:59) Future of finance and accounting teams (12:09) Truewind's approach and strategy (15:13) Role of automation in accounting (17:12) Sponsors: Notion | Puzzle (18:49) Digital staff accountant concept (19:53) Exploring AI features in finance (21:07) Government regulations and data sharing (22:23) Exciting news: Fundraising success (24:08) Customer-centric approach to product development (24:57) Advice for founders on fundraising (27:15) Defining success for Truewind (35:55) Future of finance and AI integration (37:08) Wrap

This week, Sasha Orloff sits down with Will Hubbard, Founder & COO of Agree, about building an all-in-one platform that streamlines contracting, invoicing, billing, and payments. They explore Agree’s rapid growth, recent $7.2M seed round, and how AI and user-centered design are shaping the future of finance tech. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/wbhub/ https://agree.com/ -- X/SOCIAL: @wbhub (Will) @AgreeHQ (Agree) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:41) Intro (01:23) Meet Will Hubbard: The story behind Agree (02:19) Agree: All-in-one contracting and invoicing platform (02:54) Evolution of Agree: From venture fund to B2B payments (03:54) Delightful user experience of Agree (06:06) Importance of design in accounting software (06:57) The Why Now: Bundling contracting and invoicing (08:51) Innovative features and AI-driven development (13:38) Sponsors: Notion | Puzzle (15:03) Favorite features: Tracking and reminders (17:34) Surprising use cases and rapid development (20:03) Viral growth of Agree.com (21:22) Story behind Agree.com (23:25) Challenges in naming a company (24:57) Raising the next round of funding (27:26) Future plans and product development (29:11) Advice for finance leaders and founders (34:22) Future of finance: Humans plus software (35:37) Wrap

In this episode, Sasha Orloff talks with Ali Hussain, CEO of Tabs, discuss how the company is using AI to modernize revenue and collections management, reduce DSO, and boost efficiency for finance teams. They discuss Ali’s journey from PhD dropout to fintech founder, Tabs’ $25M raise, and how the platform is reshaping B2B finance operations. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/ali-hussain786 https://tabs.inc/ -- X/SOCIAL: @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (01:04) Intro (01:43) Meet Ali Hussain (03:20) Vision behind Tabs (07:41) Challenges and opportunities in finance automation (11:06) Future of finance teams (15:29) Sponsors: Notion | Puzzle (16:53) Case study: Success with Statik (19:09) Example of Tabs in action (19:49) Future of AI in finance (21:41) Agentic future and trust (23:52) Building operational software (27:32) Favorite features and lessons learned (30:32) Venture capital and market opportunity (34:05) Advice for founders (36:58) Future plans and excitement (41:41) Wrap

This week, Sasha Orloff and Zuora CFO Todd McElhatton discuss the growing complexity of finance operations and the critical role of AI in modern accounting. They talk about the insights from the 'Modern Finance Leader' report, strategies for overcoming legacy systems, and practical advice for finance leaders navigating technological change. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/todd-mcelhatton-2140761/ https://www.zuora.com/resource/modern-finance-leader-report/_ -- X/SOCIAL: @Zuora (Zuora) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:43) Intro (01:11) Season 2 focus: Accounting and technology (01:30) Insights from the Modern Finance Leader Report (02:13) Interview with Todd McElhatton: Challenges in finance technology (05:34) The modernization Catch 22 (09:08) AI and the future of finance (13:46) Sponsors: Notion | Puzzle (15:26) Practical advice for finance leaders (16:53) Zuora's impact and client success (19:20) Role of AI and automation (21:13) Building a 'Yes' department (23:27) Advice for new finance leaders (25:46) Transforming existing finance teams (30:14) Strategic investment in technology (32:22) Evolving role of CFOs (34:21) Joining Zuora and making an impact (35:29) Client success and product value (36:39) Wrap

In this episode, Sasha Orloff talks with John Glasgow, CEO & CFO of Campfire, about building an AI-native ERP system that streamlines finance workflows through automation and faster month-end close. Fresh from raising $35 million, John shares insights on modernizing legacy systems, the challenges of building complex financial software, and why now is the right time to innovate in accounting tech. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/johnglasgow https://campfire.ai/ -- X/SOCIAL: @john__glasgow (John) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:22) Intro (01:00) Guest introduction: John Glasgow (01:51) Journey of Campfire (05:05) Challenges and innovations in accounting software (06:47) Shift to modern GL and AI integration (11:21) Sponsors: Notion | Puzzle (13:29) Real-world impact and case studies (19:11) Fundraising and future plans (20:01) Partnering with John Lockett and Excel (21:06) AI conference and bigger investments (21:48) Challenges of a seed-backed business (22:50) Advice for founders in big industries (23:36) Product velocity and customer trust (25:51) Future plans and milestones (29:24) Origin of Campfire (30:53) Message to finance leaders and founders (34:05) Future of finance and AI (36:13) Wrap

This week, Sasha Orloff and Nicolas Kopp, CEO & Founder at Rillet, discuss how Rillet is transforming accounting by leveraging AI to streamline processes, improve efficiency, and build lean finance teams. They also talk about the company’s $25 million funding from Sequoia, the importance of clean data, and Rillet’s customer-focused approach. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠⁠https://puzzle.io/⁠⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/nicolas-kopp/ https://www.rillet.com/ -- X/SOCIAL: @nicckopp (Nicolas) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (01:00) Intro (01:28) Meet Nicolas Kopp from Rillet (02:23) Rillet's mission and market (03:11) Founding story and challenges (05:27) Building a modern GL (11:27) Future of finance teams (14:56) Real-world examples and success stories (16:39) Sponsors: Notion | Puzzle (18:03) AI-powered ERP (21:28) Building a business with substance (22:03) Investor perception and challenges (22:46) Customer obsession and success (24:31) Advice for founders (27:49) The Sequoia effect (30:47) Future milestones and product vision (32:23) Customer feedback and obsession (38:47) Wrap

This week, Sasha Orloff and Worldpay Chief Product Officer Cindy Turner explore the shifting digital payments landscape—from stablecoins and agentic tech to global trends in account-to-account payments, regional behaviors, regulatory influences, and innovations like buy now, pay later. -- 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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠⁠https://puzzle.io/⁠⁠⁠ -- RECOMMENDED IN THIS EPISODE: ⁠https://www.linkedin.com/in/lucinda-turner/ ⁠http://www.worldpay.com -- X/SOCIAL: @Worldpay_Global (Worldpay) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:58) Intro (01:40) Meet Cindy Turner: Chief Product Officer of Worldpay (02:08) Cindy Turner's career journey (06:41) Global payments report (10:01) Account-to-Account payments: A global perspective (13:15) Sponsors: Notion | Puzzle (14:55) Unlocking Open Banking (17:10) E-commerce and digital payments trends (20:33) Impact of surcharging in Australia (21:56) Surcharging trends in the US (23:23) Cash dominance in certain countries (26:03) Rise of buy now, pay later (29:39) Future of payments: Agentic commerce (33:59) Stablecoins and the future of payments (37:29) Optimizing payments for businesses (38:50) Wrap

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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠⁠https://puzzle.io/⁠⁠ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/jeandenisgreze/ https://town.com/ -- X/SOCIAL: @jgreze (Jean) @TownTaxCo (Town) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:48) Intro (01:20) Jean-Denis Greze: The origin story of Town (02:10) Challenges and opportunities in business tax prep (03:41) Role of AI in automating tax preparation (05:50) Market dynamics and constraints in tax services (15:49) Sponsors: Notion | Puzzle (17:14) Unique needs of small businesses (24:38) Future of AI in tax preparation (26:12) Segmenting the small business market (27:15) Building trust and scaling AI (37:14) Exploring AI agents and their potential (47:21) Fundraising and future plans (50:57) Wrap

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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at ⁠https://puzzle.io/⁠ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/jaspar-carmichael-jack/ https://www.artisan.co/ -- X/SOCIAL: @jasparcjack (Jaspar) @GetArtisanAI (Artisan) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:38) Intro (01:08) Jaspar Carmichael-Jack, Founder & CEO of Artisan (02:53) Concept and evolution of Artisan (04:09) Challenges and iterations in AI development (05:09) Expanding Artisan's capabilities (08:33) Future of AI in the workplace (10:34) Sponsors: Notion | Puzzle (11:58) From better data to smarter responses (13:24) Funding and growth journey (16:44) Balancing AI and human labor (27:26) Fun and unusual use cases for AI (28:45) Final thoughts and lessons learned (31:09) Wrap

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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/alan-imberman-cfa-aab2371/ https://www.wealthfront.com/ -- X/SOCIAL: @Wealthfront (Wealthfront) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:48) Intro (01:16) Interview with Alan, CFO of Wealthfront (01:54) Wealthfront's vision and growth (03:24) Innovative financial products (04:19) Profitability and business model (06:03) New product launches and strategies (15:18) Tax loss harvesting and direct indexing (17:43) Sponsors: Notion | Puzzle (19:23) Wealthfront’s tax strategy triumph (23:13) Bond ladders explained (28:11) Future of Wealthfront and AI in finance (33:41) Advice for founders and finance leaders (36:01) Wrap

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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/wouterborn/ https://cfooffice.io/ -- X/SOCIAL: @wouter_born (Wouter) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:58) Intro (01:26) Meet Wouter Born: From founder to AI influencer (02:39) Wouter entrepreneurial journey (05:30) Evolution of CFOs in the age of AI (07:28) Practical AI Tips for CFOs and Founders (13:01) Future tech stack for CFOs (17:15) Sponsors: Notion | Puzzle (18:40) Changing role of CFOs (21:30) Importance of storytelling in finance (23:32) Leveraging AI for financial storytelling (25:54) Building financial tools with AI (28:51) Future of CFO tech stack (34:54) Practical advice for AI prompting (38:39) Connecting with the community (39:53) Wrap

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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/meghbartma/ https://www.crunchbase.com/ -- X/SOCIAL: @crunchbase @skyspeak (Megh) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:35) Intro (01:03) Megh Gautam, Crunchbase's Chief Product Officer (01:48) Megh’s journey to Crunchbase (04:26) Transitioning Crunchbase to an AI company (07:06) Crunchbase's AI and data insights (09:45) User engagement and product development (14:58) Sponsors: Notion | Puzzle (16:22) Forbes article on Crunchbase's AI model (24:58) Pricing strategies and user experience (29:33) Future of AI in product management (35:53) Conclusion and future collaboration (38:27) Wrap

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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/benjamin-cohen-0618308/ https://www.deel.com/ -- X/SOCIAL: @deel @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:40) Intro (01:51) Understanding Deal's global hiring report (02:38) Insights on data utilization (04:42) Collaboration and data storytelling (08:23) Generational workforce trends (08:41) Gen Z's impact on the workforce (13:59) Sponsors: Notion | Puzzle (15:39) Global hiring trends and challenges (19:49) Introduction to global hiring trends (20:28) Surprising rise of accountants (22:52) Impact of AI on job market (25:31) Employee terminations and market trends (30:01) Tools and insights for global hiring (33:06) Best practices for a global workforce (36:33) Data analysis tools (38:15) Wrap

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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/chkashifali/ https://www.taxgpt.com/ -- X/SOCIAL: @AskTaxGPT @ChKashifAli (Kash) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:45) Intro (01:14) Meet Kash Ali: The Journey Begins (01:35) Inception of TaxGPT (02:41) From side project to startup (04:16) Securing the domain and early success (07:13) Kash Ali's background and path to Silicon Valley (13:11) Evolution of TaxGPT (13:33) Sponsors: Notion | Puzzle (14:59) TaxGPT's unique value proposition (19:28) Future of TaxGPT and AI integration (20:44) Evolution of AI models (21:48) Enhancing workflows with frontier models (23:03) Importance of prompting in AI (28:13) Journey to Y Combinator (29:55) Fundraising success and future vision (33:06) Future of accounting and AI (40:16) Adopting AI solutions in accounting firms (41:29) Wrap

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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/donald-gossen-40ab96/ https://nevermined.io/ -- X/SOCIAL: @Nevermined_io @dongossen (Donald) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:50) Intro (01:18) Overview of AI-to-AI payments and decentralized finance (02:34) Vision behind Nevermined (04:01) Challenges in AI payment systems (05:34) Nevermined: The PayPal of AI (06:52) Future of AI commerce (11:46) Real-world applications and security (13:54) Sponsors: Notion | Puzzle (15:17) Security & trust in AI transactions (19:39) Evolution of AI agents (27:45) Building Nevermined and fundraising (32:31) Wrap

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 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/ -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/ankurdahiya/ https://www.fifteenth.com -- X/SOCIAL: @sashaorloff (Sasha) @ankurd (Ankur) -- TIMESTAMPS: (00:00) Intro (01:37) Guest Introduction: Ankur Dahiya (02:24) Problem with taxes (03:01) Birth of Fifteenth (08:33) Combining human expertise with AI (12:22) Future of AI in tax solutions (14:40) Sponsors: Notion | Puzzle (16:03) Managing personal finances (19:42) Fundraising and building the team (25:49) Challenges and advice for founders (27:55) Tax tips for founders and engineers (33:12) Wrap

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. -- SPONSORS: Puzzle 📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/ Found Found provides small business owners tools to track expenses, calculate taxes, manage cashflow, send invoices and more. Open a Found account for free at https://found.com/econ102 -- RECOMMENDED IN THIS EPISODE: https://www.linkedin.com/in/mtait83/ https://www.decimal.com/ -- X/SOCIAL: @GoDecimal (Decimal) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Intro (00:59) Season 2 changes (01:48) Exciting times in accounting (03:12) Interview with Matt Tate, CEO of Decimal (04:22) Rise and fall of Bench (06:18) Challenges in the accounting industry (13:03) Founding and vision of Decimal (16:46) Sponsors: Puzzle | Found (18:34) Acquisition of KPMG Spark (23:11) Team collaboration and roadmap insights (23:45) Scaling with Puzzle's AI native ledger (24:31) Evaluating technology partnerships (28:59) Role of trust and accountability in accounting (29:43) AI's impact on client experience (31:08) Human interaction vs. full automation (36:22) Future of AI in accounting (43:34) Implementing AI tools at scale (45:14) Wrap

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. — 🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse. — Highlights from the Episode: Accounting profession is facing its most significant period of change, with AI and automation creating both challenges and opportunities for practitioners at all levels. There's currently a major pipeline issue in accounting - with 75% of CPAs approaching retirement age and not enough new talent entering the field. Despite technological advances, the fundamental need for trust and human interpretation in accounting remains paramount, suggesting AI will augment rather than replace accountants. — RECOMMENDED PODCAST: Check out Modern Relationships, where Erik Torenberg interviews tech power couples and leading thinkers to explore how ambitious people actually make partnerships work. Founders Fund's Delian Asparouhov and researcher Nadia Asparouhova kick off the series with an unfiltered conversation about their relationship evolution. Apple: https://podcasts.apple.com/us/podcast/id1786227593 Spotify: https://open.spotify.com/show/5hJzs0gDg6lRT6r10mdpVg YouTube: https://www.youtube.com/@ModernRelationshipsPod -- SPONSOR: 📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you - try it for free at https://www.notion.com/upstreampod — LINKS: https://www.linkedin.com/in/davehartley/ — X/SOCIAL: @sashaorloff (Sasha)

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. — 🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse. — Highlights from the Episode: Creating a competitive process with multiple potential buyers is crucial for maximizing exit value - "if you have one buyer, you have no buyer" Proper preparation and documentation (clean financials, confidential information memorandum) significantly speeds up the acquisition process and builds buyer confidence Being transparent about business challenges upfront ("bruises and all") builds trust and allows you to control the narrative around potential objections -- RECOMMENDED PODCAST: Check out Modern Relationships, where Erik Torenberg interviews tech power couples and leading thinkers to explore how ambitious people actually make partnerships work. Founders Fund's Delian Asparouhov and researcher Nadia Asparouhova kick off the series with an unfiltered conversation about their relationship evolution. Apple: https://podcasts.apple.com/us/podcast/id1786227593 Spotify: https://open.spotify.com/show/5hJzs0gDg6lRT6r10mdpVg YouTube: https://www.youtube.com/@ModernRelationshipsPod — SPONSOR: 📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you - try it for free at https://www.notion.com/upstreampod — LINKS: Acquire: https://acquire.com/ https://www.linkedin.com/in/agazdecki/ — X/SOCIAL: @acquiredotcom (Acquire) @agazdecki (Andrew) @sashaorloff (Sasha) — TIMESTAMPS: (00:00) Intro (02:10) Personal lessons from selling Business Apps (03:50) Building Acquire.com from personal experience (06:49) First acquisition story with ESW Capital (09:28) Negotiating terms and tax considerations (12:20) Story of Altcoin acquisition (13:53) Sponsor: Notion (15:15) Experience at Spiff and path to Acquire.com (18:35) Maximizing exit value strategies (25:47) Process of listing on Acquire.com (27:36) Types of buyers and deal sizes (29:34) Success stories and notable deals (32:57) Future plans for Acquire.com (34:04) Wrap

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 — 🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse. — SPONSOR: 📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you - try it for free at https://www.notion.com/upstreampod — LINKS: Streamlining Accounts Receivable: Transforming an Overlooked Cornerstone of Business Operations: https://www.justpaid.ai/blog/streamlining-accounts-receivable JustPaid: https://www.justpaid.ai https://www.linkedin.com/in/kivatinos/ https://www.linkedin.com/in/anelya/ — X/SOCIAL: @getjustpaid (JustPaid) @danielkivatinos (Daniel) @sashaorloff (Sasha)

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 — 🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse. — 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: 📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you - try it for free at https://www.notion.com/upstreampod — LINKS: Matt Lerner's company: https://www.systm.co/ CRAFTED. podcast: https://crafted.fm Growth Levers: https://www.amazon.com/dp/173842622X — LinkedIn: Matt Lerner https://www.linkedin.com/in/matthewlerner/ Dan Blumberg https://www.linkedin.com/in/dblums/ Sasha Orloff https://www.linkedin.com/in/sashaorloff/

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 — 🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse. — 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: 📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you - try it for free at https://www.notion.com/product/ai?utm_source=podcasts&utm_medium=upstreampod — LINKS: AI Finance Club: https://ai-finance.club/ https://www.linkedin.com/in/bouchernicolas/ — X/SOCIAL: @BoucherNicolas (Nicolas) @sashaorloff (Sasha)

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: 🌎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. 💳 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 https://www.rippling.com/turpentine for a free demo and one month free trial. 📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you - try it for free at https://www.notion.com/product/ai?utm_source=podcasts&utm_medium=upstreampod -- LINKS: Copilot Money: https://copilot.money/ https://www.linkedin.com/in/andresugarte/ -- X/SOCIAL: @chuga (Andrés) @sashaorloff (Sasha)

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 -- 📰Be notified early when Turpentine drops new publication: https://www.turpentine.co/exclusiveaccess -- 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: -- 🌎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. 💳 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 https://www.rippling.com/turpentine for a free demo and one month free trial. -- LINKS: The FP&A Guy: https://www.thefpandaguy.com/ https://www.linkedin.com/in/TheFPandAGuy/ -- X/SOCIAL: @sashaorloff

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 -- 📰Be notified early when Turpentine drops new publication: https://www.turpentine.co/exclusiveaccess -- 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: 🌎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. 💳 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 https://www.rippling.com/turpentine for a free demo and one month free trial. -- LINKS: Kount: https://kount.com/ https://www.linkedin.com/in/bradwiskirchen/ -- X/SOCIAL: @sashaorloff @KountInc

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. 🔥 Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/ -- 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. Trusted by Notion, Anthropic, and Vanta. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy. -- LINKS: Airbase: https://www.airbase.com/ -- X/SOCIAL: @sashaorloff @AVallurupalli -- TIMESTAMPS: (00:00) Preview (01:16) Intro (01:43) Meet Aneal Vallurupalli, CFO of Airbase (02:28) Understanding Airbase's spend management (04:33) Aneal’s journey to Airbase (08:08) Evolution and impact of Airbase (09:43) Role and strategy as CFO (17:34) Sponsor: Anrok (18:59) Balancing flexibility and control in spend management (21:36) Importance of change management (23:58) Memorable customer success stories (27:35) Evolution of software in the CFO's office (31:21) Trends in selling to different industries (37:08) Future of Airbase and business spend management (39:36) Insights on M&A and career journey (43:37) Reflections on buy-side and sell-side experiences (45:39) Wrap

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. 🔥Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/ -- RECOMMENDED PODCAST: 🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937 Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz -- SPONSORS: RIPPLING 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 https://www.rippling.com/turpentine for a free demo and one month free trial. 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. -- LINKS: Flippa: https://flippa.com/ https://www.linkedin.com/in/blakehutchison/ -- X/SOCIAL: @sashaorloff @Flippa -- TIMESTAMPS: (00:00) Preview (01:20) Intro (02:26) Blake's career journey (03:37) Flippa: The investment bank for the 99% (05:55) Focus on digital assets (07:20) Selling and buying on Flippa (14:20) Buyer types and market dynamics (18:30) Sponsors: Rippling | Anrok (21:22) Investing in digital assets (26:28) Navigating the first-time buyer market (28:05) Buyer intent and market trends (33:47) Common deal breakers in business sales (36:46) Financial literacy and cloud accounting (44:27) Future trends in online business flipping (47:47) Getting started with Flippa (49:02) Wrap

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. 🔥Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/ -- RECOMMENDED PODCAST: 🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937 Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz -- 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: https://www.linkedin.com/in/eugene-spevakov-cfa/ 6sense: https://6sense.com/ -- X/SOCIAL: @sashaorloff -- TIMESTAMPS: (00:00) Preview (00:49) Intro (01:14) Understanding treasury (02:22) Meet Eugene Spevakov: A treasury expert (03:39) Basics of treasury functions (05:40) Real-world treasury challenges and risks (09:12) Industry-specific treasury insights (14:07) Sponsors: Anrok | Netsuite (16:30) Treasury in software companies (22:32) Risk management and allocation (27:29) Sponsors: Metaview | Omneky (28:58) When to hire a treasury professional (30:07) Understanding and managing business risks (32:40) Challenges and solutions in treasury functions (37:08) Role and excitement of treasury (43:12) Tools and resources for treasury management (47:40) Advice for building a treasury function (50:32) Wrap

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. 🔥Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/ -- RECOMMENDED PODCAST: 🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937 Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz -- SPONSORS: 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 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 BRAVE: Get first-party targeting with Brave’s private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/brave-ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign. 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: https://www.linkedin.com/in/camillericketts/ XYZ: https://www.xyz.vc/ -- X/SOCIAL: @sashaorloff @camillericketts -- TIMESTAMPS: (00:00) Episode Preview (00:58) Conversation with Camille Ricketts (02:11) Camille's journey at Notion (04:34) Content as a measurable growth strategy (12:00) Effective use of testimonials and case studies (15:45) Case studies and emotional engagement (17:54) Sponsors: Netsuite | Metaview (19:41) Measuring content success (24:25) Tactical tips for effective call to action (26:08) Figma and Stripe (27:37) Founding story of First Round Review (30:30) Sponsors: Brave | Omneky (31:52) Iterating content formats and overcoming fear (37:04) Role of AI in content creation (42:57) Insights from Tesla and preparing for the unexpected (47:24) Wrap

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. 🔥Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/ -- RECOMMENDED PODCAST: 🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. They unpack their hottest takes on the future of tech, business, venture, investing, and politics. Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937 Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz YouTube: https://www.youtube.com/@ThisWontLastpodcast -- SPONSORS: 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 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 BRAVE: Get first-party targeting with Brave’s private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/brave-ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign. 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: Cook’s Playbooks https://jcookflix.substack.com/ Founder Mode PG https://paulgraham.com/foundermode.html Lenny’s Podcast episode with Brian Chesky https://www.youtube.com/watch?v=4ef0juAMqoE Product-CEO Paradox by Ben Horowitz https://a16z.com/why-founders-fail-the-product-ceo-paradox/ Hard Thing About Hard Things by Ben Horowitz https://a16z.com/books/the-hard-thing-about-hard-things/ Scaling People with Claire Hughes Johnson https://www.goodreads.com/book/show/63063173-scaling-people -- X/SOCIAL: @sashaorloff @cookflix -- TIMESTAMPS: (00:00) Episode preview (00:26) Intro (00:51) Founder Mode essay (04:13) Challenges of polarized arguments (07:44) Importance of leadership mode (10:59) Balancing founder and scaling modes (15:01) Sponsors: Netsuite | Metaview (16:49) Trust and transparency in leadership (20:41) Importance of creating a culture (24:57) Leading with values and behaviors (29:48) Sponsors: Brave | Omneky (31:13) Importance of documentation (36:45) Balancing founder and manager roles (39:06) Structuring ownership and accountability (43:06) Founders as Coaches and Captains (48:12) Specialized operators in finance (50:41) Scaling company to public (53:50) Wrap

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. 🔥Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/ -- RECOMMENDED PODCAST: 🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. They unpack their hottest takes on the future of tech, business, venture, investing, and politics. Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937 Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz YouTube: https://www.youtube.com/@ThisWontLastpodcast -- SPONSORS: 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 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 BRAVE: Get first-party targeting with Brave’s private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/brave-ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign. 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: http://fsuite.co https://www.fsuite.co/compensation-survey http://lsuite.co http://www.thesuite.com -- X/SOCIAL: @sashaorloff @chris_sands_ -- TIMESTAMPS: (00:00) Episode preview (01:16) Intro (01:40) Meet Chris Sands: Head of Jobs at The F Suite (03:06) Evolving role of the CFO (09:11) Strategies for aspiring CFOs (12:29) Candidate-first approach in recruitment (13:56) Then vs Now: Hiring CFOs (19:14) Preparing candidate for interviews (22:53) Sponsors: Netsuite | Metaview (24:40) Best practices in recruiting finance teams (26:19) Role of CFO in the hiring process (27:28) Advice for recruiting CFOs (29:28) Sponsors: Brave | Omneky (30:56) Key traits of a great CFO (32:52) Evolution of CFO roles (34:10) Misconceptions on job search (37:56) CFO compensation insights (44:49) Negotiation strategies for CFOs (48:04) Non-negotiable compensation offers (48:59) F Suite: Building a community for CFOs (52:39) Wrap

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: 🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. They unpack their hottest takes on the future of tech, business, venture, investing, and politics. Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937 Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz YouTube: https://www.youtube.com/@ThisWontLastpodcast -- SPONSORS: 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 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 BRAVE: Get first-party targeting with Brave’s private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/brave-ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign. 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/ -- X/SOCIAL: Sasha on X: @sashaorloff Valerie's LinkedIn: https://www.linkedin.com/in/burmanval/ -- TIMESTAMPS: (00:00) Introduction (01:45) Valerie Berman: From tech to Tahoe (03:00) Transitioning to Sugar Bowl (05:21) Day one as CFO: Skiing and listening (07:02) Unique aspects of Sugar Bowl (08:13) Balancing fun and financials (13:05) Sponsors: Netsuite | Metaview (14:54) Measuring success and setting goals (24:27) Navigating seasonal business challenges (30:00) Building a dream team at Sugar Bowl (32:24) Sponsors: Brave | Omneky (33:46) Insights on M&A and corporate development (36:24) Decision making in private companies (42:02) Significant role of cultural alignment (46:07) Advice for aspiring CFOs (48:06) Closing remarks and outro

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: 🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. They unpack their hottest takes on the future of tech, business, venture, investing, and politics. Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937 Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz YouTube: https://www.youtube.com/@ThisWontLastpodcast SPONSORS: 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 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 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 Omneky: 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/ X/SOCIAL: @sashaorloff @rishigarg (Rishi) TIMESTAMPS: (00:00:00) Introduction (00:02:53) How companies should think about M&A and corp dev (00:06:58) Signs that a company is ready to consider M&A (00:11:37) Different approaches to M&A: tops down, bottoms up, and strategy influencing (00:16:52) How to start building an M&A team (00:18:16) Sponsors: Netsuite | Metaview (00:22:15) Misconceptions about M&A in Silicon Valley (00:26:53) Valuation considerations in M&A deals (00:34:31) Current state of M&A market and opportunities (00:38:24) Sponsors: Omneky | Brave (00:39:47) How M&A deals happen and relationship building (00:45:55) Reasons why M&A deals don't work out (00:51:50) Transition to Rishi's experience as a venture capitalist (00:57:50) Advice for founders considering M&A (01:02:09) Rishi's current interests in investing, particularly in AI and new platforms

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/ Listen here at: https://www.ericriesshow.com/ RECOMMENDED PODCAST 🎙️ This Won't Last - Eavesdrop on Keith Rabois, Kevin Ryan, Logan Bartlett, and Zach Weinberg's monthly backchannel. They unpack their hottest takes on the future of tech, business, venture, investing, and politics. Apple Podcasts: https://podcasts.apple.com/us/podcast/id1765665937 Spotify: https://open.spotify.com/show/2HwSNeVLL1MXy0RjFPyOSz YouTube: https://www.youtube.com/@ThisWontLastpodcast 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 (00:42:36) - Challenges and questions companies ask behind the scenes (00:50:36) - Brief mention of companies listed on LTSE (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