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 Wilkinson has played every game.
He built 38 companies, lost $10 million, ... Show More
Jul 2022
Andrew Wilkinson: Tiny Holdings
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 happin ... Show More
1h 15m
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
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
Oct 2024
6 startup ideas from the tech Warren Buffett (make $120k/mo)
Join me as I chat with Andrew Wilkinson, Co-Founder of Tiny, as we explore innovative startup ideas, and his frameworks for finding and building startupsTimestamps
00:00 Intro
01:55 Startup Idea 1: Robot Lawn-mowing Service/Directory
17:54 Startup Idea 2: CPAP alternatives for Sl ... Show More
53m 45s
>> Get The Book (Buy Back Your Time): https://bit.ly/3pCTG78 >> Subscribe to My Newsletter: https://bit.ly/3Not every business is worth starting, and some will waste years of your life. I’ve built 7 multimillion-dollar companies and coached hundreds of ... Show More
