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

• E62: From Divvy FP&A to Parallel Founder: How Renato Villanueva Built the Tool Finance Actually Wants

  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

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• E61: Maxima's $41M Mission: Automating Enterprise Accounting Close with AI

  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

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• E60: Deel's COO on Scaling to $17.3B Valuation (and Where They Go From Here)

  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

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• E59: Why AI Tax Tools Fail the QSBS Test, with Nick Abouzeid of Rivet

  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

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• E58: The future of M&A is AI? With Blake Hutchison, CEO of Flippa

  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

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