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.

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🎙️ 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

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SPONSORS:

RIPPLING

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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.

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LINKS:

Flippa: https://flippa.com/

https://www.linkedin.com/in/blakehutchison/

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X/SOCIAL:

@sashaorloff

@Flippa

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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