Podcast Episodes
Back to Search
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 8 hours 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 1 week, 5 days 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 3 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 1 month, 1 week 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 1 month, 2 weeks 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 1 month, 3 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 1 month, 3 weeks ago
E49: Why Accel Backed Campfire to Build the Modern GL, with John Glasgow, CEO
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. …
Published on 2 months ago
E48: Why Sequoia Invested $25M in Accounting Software with Rillet CEO Nicolas Kopp
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 t…
Published on 2 months, 1 week ago
E47: Agentic Commerce, Stablecoins, and Global Trends with Cindy Turner, CPO of Worldpay
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 paymen…
Published on 3 months ago