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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 …
Published on 8 hours ago
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 explo…
Published on 2 weeks, 5 days ago
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 wi…
Published on 1 month, 2 weeks ago
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 le…
Published on 1 month, 3 weeks ago
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 t…
Published on 2 months, 1 week ago
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 bey…
Published on 2 months, 2 weeks ago
E53: How AI Agents are Replacing Manual Accounting Work with Truewind CEO Alex Lee
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 …
Published on 3 months ago
E52: Building a Viral Contract Platform: Will Hubbard, CEO of Agree
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…
Published on 3 months, 1 week ago
E51: Ramp for Revenue: The Tabs Playbook for Faster Cash Flow with CEO Ali Hussain
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 te…
Published on 3 months, 2 weeks ago
E50: Zuora CFO Todd McElhatton on Why 70% of Finance Stacks Hold Back Growth
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 'Mod…
Published on 3 months, 3 weeks ago