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EPISODE · Apr 27, 2026 · 1H 12M
Justin Yoshimura - Resurrecting & Rolling Up Retail - [Joys of Compounding, EP. 35]
from Joys of Compounding · host Colossus | Investing & Business Podcasts
Our teacher today is Justin Yoshimura, founder and CEO of CSC Generation, a profitable commerce platform doing over a billion dollars in annual revenue across brands including Sur La Table, Backcountry, and One Kings Lane. As we explore what it takes to build an enduring company in a sector most investors have written off, we turn to Justin's unconventional path, one that challenges familiar assumptions about credentials, capital structure, and the future of retail. Justin shares how he stopped attending school around the age of sixteen and built his own curriculum through entrepreneurship, selling cell phones on eBay as a teenager before founding a loyalty program SaaS company that was acquired by Merkle in his early twenties. He describes the influences that shaped CSC's design, including a Warren Buffett obsessed father and the long term holding company model he watched David Williams build at Merkle, and explains why he rejected the traditional buy and flip playbook in favor of permanent ownership backed by patient, contrarian capital. This special session explores Justin's approach to acquiring retail brands in transition, the AI native operating system called Genesis that has turned loss making companies profitable within the first year of ownership, and the lessons he has carried through COVID, tariffs, and a decade of building a contrarian business in an industry many had written off. Please enjoy class with Justin Yoshimura. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at colossus.com/subscribe. ----- This episode is brought to you by https://www.portraitanalytics.ai/ - your centralized resource for AI-powered idea generation, thesis monitoring, and personalized report building. Built by buy-side investors, for investment professionals. We work in the background, helping surface stock ideas and thesis signposts to help you monetize every insight. In short, we help you understand the story behind the stock chart, and get to "go, or no-go" 10x faster than before. Sign-up for a free trial today at https://www.portraitresearch.com ----- This episode is brought to you by Eight Sleep — the Pod is a smart mattress cover designed to improve sleep by automatically cooling or heating your bed throughout the night. Built on the science that your body needs to cool down to reach deep sleep, it tracks your sleep and adjusts in real time to help you get better rest, recovery, and overall sleep quality. No wearables required. Use the code JOYS at https://www.eightsleep.com/joys for up to $350 off the Pod 5. ----- Joys of Compounding is a property of Pine Grove Studios in collaboration with Colossus, LLC. For more episodes of Joys of Compounding, visit colossus.com/episodes. Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Follow us on Twitter: @Buhrman_Rick | @PaulBuser | @colossusmag Timestamps (00:00:00) Welcome to Joys of Compounding (00:04:20) Episode Intro: Justin Yoshimura (00:07:02) Justin's Early Life and Childhood (00:10:20) Developing an Entrepreneurial Spirit (00:12:08) Building a Cell Phone Marketplace (00:14:39) Resilience as a Skill (00:16:26) Lessons from Y Combinator & Merkle (00:19:25) Why Choose Retail (00:22:12) Brands That Hit a Growth Wall (00:25:18) CSC's Founding Story (00:27:33) Direct Buy: CSC's First Deal (00:29:29) Justin's Fundraising Journey (00:32:15) Navigating the COVID Boom-Bust (00:36:19) Death by a Thousand Cuts in Retail (00:38:06) Competing for Deals (00:40:41) Lessons from the Tariff Shock (00:43:00) Backcountry Case Study (00:45:23) CSC's Genesis Platform (00:49:31) How AI is Changing Companies (00:52:01) Building an AI-First Culture (00:55:57) Hiring Well in the AI Era (00:58:09) Incentive Structures & Retention (01:01:40) Looking Ahead: CSC's Next Decade (01:05:08) Solving the Biggest Risk in Retail (01:08:30) The Decline of Search Traffic to Retailers (01:10:56) Closing Advice for Young People
What this episode covers
Our teacher today is Justin Yoshimura, founder and CEO of CSC Generation, a profitable commerce platform doing over a billion dollars in annual revenue across brands including Sur La Table, Backcountry, and One Kings Lane. As we explore what it takes to build an enduring company in a sector most investors have written off, we turn to Justin's unconventional path, one that challenges familiar assumptions about credentials, capital structure, and the future of retail. Justin shares how he stopped attending school around the age of sixteen and built his own curriculum through entrepreneurship, selling cell phones on eBay as a teenager before founding a loyalty program SaaS company that was acquired by Merkle in his early twenties. He describes the influences that shaped CSC's design, including a Warren Buffett obsessed father and the long term holding company model he watched David Williams build at Merkle, and explains why he rejected the traditional buy and flip playbook in favor of permanent ownership backed by patient, contrarian capital. This special session explores Justin's approach to acquiring retail brands in transition, the AI native operating system called Genesis that has turned loss making companies profitable within the first year of ownership, and the lessons he has carried through COVID, tariffs, and a decade of building a contrarian business in an industry many had written off. Please enjoy class with Justin Yoshimura. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at colossus.com/subscribe. ----- This episode is brought to you by https://www.portraitanalytics.ai/ - your centralized resource for AI-powered idea generation, thesis monitoring, and personalized report building. Built by buy-side investors, for investment professionals. We work in the background, helping surface stock ideas and thesis signposts to help you monetize every insight. In short, we help you understand the story behind the stock chart, and get to "go, or no-go" 10x faster than before. Sign-up for a free trial today at https://www.portraitresearch.com ----- This episode is brought to you by Eight Sleep — the Pod is a smart mattress cover designed to improve sleep by automatically cooling or heating your bed throughout the night. Built on the science that your body needs to cool down to reach deep sleep, it tracks your sleep and adjusts in real time to help you get better rest, recovery, and overall sleep quality. No wearables required. Use the code JOYS at https://www.eightsleep.com/joys for up to $350 off the Pod 5. ----- Joys of Compounding is a property of Pine Grove Studios in collaboration with Colossus, LLC. For more episodes of Joys of Compounding, visit colossus.com/episodes. Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Follow us on Twitter: @Buhrman_Rick | @PaulBuser | @colossusmag Timestamps (00:00:00) Welcome to Joys of Compounding (00:04:20) Episode Intro: Justin Yoshimura (00:07:02) Justin's Early Life and Childhood (00:10:20) Developing an Entrepreneurial Spirit (00:12:08) Building a Cell Phone Marketplace (00:14:39) Resilience as a Skill (00:16:26) Lessons from Y Combinator & Merkle (00:19:25) Why Choose Retail (00:22:12) Brands That Hit a Growth Wall (00:25:18) CSC's Founding Story (00:27:33) Direct Buy: CSC's First Deal (00:29:29) Justin's Fundraising Journey (00:32:15) Navigating the COVID Boom-Bust (00:36:19) Death by a Thousand Cuts in Retail (00:38:06) Competing for Deals (00:40:41) Lessons from the Tariff Shock (00:43:00) Backcountry Case Study (00:45:23) CSC's Genesis Platform (00:49:31) How AI is Changing Companies (00:52:01) Building an AI-First Culture (00:55:57) Hiring Well in the AI Era (00:58:09) Incentive Structures & Retention (01:01:40) Looking Ahead: CSC's Next Decade (01:05:08) Solving the Biggest Risk in Retail (01:08:30) The Decline of Search Traffic to Retailers (01:10:56) Closing Advice for Young People
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Justin Yoshimura - Resurrecting & Rolling Up Retail - [Joys of Compounding, EP. 35]
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