holding-company
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Dominic Wells and the trouble with thinking bigger
An English teacher in Taiwan learned to build websites, then to buy businesses. Taking Onfolio public gave Dominic Wells a larger stage - and a much less forgiving set of numbers.
Sieva Kozinsky and the business of staying
He built a marketplace for college notes, then began buying companies he hoped never to sell. At Enduring Ventures, Sieva Kozinsky is testing what happens when an owner trades the exit clock for a much longer calendar.
Nick Swenson and the art of leaving room
A Minneapolis credit investor became the operator of an aviation holding company. At Air T, Nick Swenson is testing how far patient capital and independent teams can travel together.
Fernando De Leon and the education of an owner
Before he founded Leon Capital Group, Fernando De Leon crossed the border for school and traded translation fees for a stake in the future. His career keeps returning to the same question: who gets to own what comes next?
Justin Yoshimura
Justin Yoshimura is the founder, chairman, and CEO of CSC Generation, an AI-native retail holding company that acquires and modernizes established brands such as Sur La Table, Z Gallerie, and One Kings Lane. A high-school dropout who built a million-dollar cell-phone marketplace as a teenager, he went on to found the Y Combinator-backed loyalty platform 500friends (acquired by Merkle in 2014) and made the Forbes 30 Under 30 list. Today he runs CSC Generation as a Constellation Software-style roll-up, buying distressed retailers and rebuilding them on data, automation, and CSC's proprietary Genesis platform.
Andrew Wilkinson
Andrew Wilkinson is a Canadian entrepreneur, investor, and author who built Tiny - a publicly traded holding company (TSX: TINY) often called 'the Berkshire Hathaway of the internet' - from a one-man design agency he started with $200 at age 20. Having dropped out of university after less than a year, he transformed a $6.50/hour barista gig into a billion-dollar empire of 32+ internet businesses including Dribbble, AeroPress, Letterboxd, and Serato. His 2024 memoir 'Never Enough: From Barista to Billionaire' became a USA Today bestseller and candidly explores why wealth didn't bring happiness, his ADHD diagnosis, and his commitment to giving away most of his fortune through the Giving Pledge.
Greg Isenberg
Greg Isenberg is the CEO and co-founder of Late Checkout, an 8-figure bootstrapped holding company that builds community-first internet businesses. Known as 'The Community Guy' in startup circles, he has two startup exits under his belt (5by to StumbleUpon, Islands to WeWork), hosts The Startup Ideas Podcast (top 0.1% tech podcast), writes a Substack newsletter with 150K+ subscribers, and has built a 500K+ following on X by giving away startup ideas for free. His ACP Framework (Audience-Community-Product) has become a widely adopted playbook for modern founders.