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.
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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/
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RECOMMENDED IN THIS EPISODE:
https://flippa.com/product/dealsourcing/
https://www.linkedin.com/in/blakehutchison
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X/SOCIAL:
@Flippa (Flippa)
@sashaorloff (Sasha)
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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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38:01
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38:01
E57: Lessons from Brex, SVB, a16z: How Jason Mok Spots What Founders Need Before They Know It
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.
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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/
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RECOMMENDED IN THIS EPISODE:
https://www.linkedin.com/in/jasonmok/
https://www.brex.com/
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X/SOCIAL:
@jasonmok (Jason)
@brexHQ (Brex)
@sashaorloff (Sasha)
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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
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56:11
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56:11
E56: 5,000 Startups Later: Tax Lessons Every Founder Needs with Joe Faris
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.
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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/
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RECOMMENDED IN THIS EPISODE:
https://www.linkedin.com/in/farisjoe/
https://accountalent.com/
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X/SOCIAL:
@sashaorloff (Sasha)
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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
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43:03
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43:03
E55: First Round and YC-Backed Startup 'Eliminating Business Bullshit' | Josh Wymer, CEO of CentralHQ
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.
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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/
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RECOMMENDED IN THIS EPISODE:
https://www.linkedin.com/in/joshwymer/
https://centralhq.com/
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X/SOCIAL:
@jbwyme (Josh)
@CentralHQX (Central HQ)
@sashaorloff (Sasha)
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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
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39:55
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39:55
E54: Filling the Gap Between QuickBooks and NetSuite with SoftLedger CEO Ben Taylor
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.
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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/
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RECOMMENDED IN THIS EPISODE:
https://www.linkedin.com/in/bentaylor8/
https://softledger.com
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X/SOCIAL:
@SoftLedger (SoftLedger)
@sashaorloff (Sasha)
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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
Sobre "Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
On Tech Finance, host Sasha Orloff brings you inside the office of the CFO - covering major tech finance news including funding announcements, deals, product launches, and emerging players shaping B2B fintech. We break down the week's biggest developments in finance tech and accounting, and explore how finance leaders are putting AI to work.
Tech Finance is brought to you by Puzzle, the modern accounting platform with an AI-first ledger, built for speed, automation, and real time decision making. Learn more: puzzle.io
Tech Finance is part of the Turpentine podcast network. Learn more: turpentine.co
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