My guest is businessman and investor Andrew Wilkinson, who has made a career out of channeling his entrepreneurial spirit, but he knows that sometimes that energy can be a double-edged sword.
We discuss the lessons learned acquiring 40 companies, why he struggled to find happiness and what changed, mimetic desire, competing with venture-backed companies, h ... Show More
Sep 15
Tobi Lütke: AI Agents, Better Decisions, and the Future of Work
Shopify founder and CEO Tobi Lütke joins Shane Parrish to discuss AI agents, better decision-making, and the future of work. He explains how he uses an AI council to examine his hardest decisions and why taste, judgment, and responsibility become more valuable as AI becomes more ... Show More
1h 5m
Mar 2023
TIP540: Lessons in Life and Business from a Self-Made Billionaire w/ Andrew Wilkinson
Trey chats with billionaire entrepreneur and investor, Mr. Andrew Wilkinson. They discuss various topics, including self-care and parenting, as well as exciting deals he collaborated on with Bill Ackman and Howard Marks. Andrew is the co-founder of Tiny, which has been called the ... Show More
1h 2m
Jul 2025
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny)
Andrew Wilkinson is the co‑founder of Tiny, a holding company that quietly owns more than three dozen profitable internet and consumer brands, including Dribbble and the AeroPress coffee maker. Starting as a teenage barista and web designer, he’s created a portfolio approaching $ ... Show More
1h 28m
Oct 2022
Asking Billionaire Investor - Andrew Wilkinson - How To Prepare For The Economic Collapse
Episode 371: Shaan Puri (@ShaanVP) and Sam Parr (@TheSamParr) talk to billionaire investor, Andrew Wilkinson (@awilkinson), about winterizing your business and finances, taking random lunches, and why renting is better than buying.
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Links:
* Tiny
* Bridgebase
* DealMaker
* O ... Show More
1h 26m
Nov 2025
I Ranked the Best & WORST Businesses to Start Before 2026 | Andrew Wilkinson
Which business model should you start? Get Andrew's cheat sheet with his full ranking and real profit margins here: https://clickhubspot.com/dge Episode 762: What’s the best business to start in 2026? Agencies, SaaS, Restaurants, Real Estate, Marketplaces. Angel Investing; Andrew ... Show More
1h 20m
Apr 2020
#63 with Andrew Wilkinson - Buying cash-flowing internet companies, starting job boards and building no code projects
Sam (@thesamparr) and Shaan (@shaanvp) are joined today by Andrew Wilkinson (@awilkinson) who is the co-founder of Tiny (tinycapital.com) - the internet version of Berkshire Hathaway. Shaan also launched a newsletter version of the podcast, subscribe to it to receive startup idea ... Show More
1h 18m
Oct 2021
Dopamine Fasts, Cruise Ship Investing, and Elon Musk vs. Jeff Bezos Feuds with Andrew Wilkinson, Co-Founder of Tiny
Andrew Wilkinson (@awilkinson), Co-Founder of Tiny, joins Sam Parr (@theSamParr) and Shaan Puri (@ShaanVP) to talk about how he found joy through a four-week dopamine fast, why it can be better to make safer “cruise ship investments” rather than startup investments, how Andrew’s ... Show More
1h 27m
Oct 2020
MFM x Trends: How to Hire a CEO to Run Your Company with Andrew Wilkinson
The best business hack ever: Learn how to hire CEOs to run your company. This is a short preview of a special edition episode for Trends subscribers. In this ep, we talk to Andrew Wilkinson, founder of Tiny...a startup conglomerate that owns 20 different companies, each with thei ... Show More
18m 17s