Interviews, Podcasts & Press

Andrew Wilkinson: AI Agents Do My Job

• ·How I run my business with AI
• ·Building Deep Personality for relationships
• ·Using OpenClaw to automate tasks

#136 Decoding Success with Andrew Wilkinson Part 1

• ·My journey from barista to billionaire
• ·Lessons from my memoir Never Enough
• ·How I built Tiny's portfolio companies

From Espresso Shots to a Billionaire Empire: Andrew Wilkinson's Quiet Blueprint

• ·How I started my first business
• ·Buying profitable internet companies
• ·Why I love playing pickleball

Opus 4.5 Changed How Andrew Wilkinson Works and Lives

• ·Building an AI relationship counselor
• ·Creating a custom email client
• ·Automating my personal life with AI

I Ranked the Best & Worst Businesses to Start Before 2026

• ·Ranking the best businesses for 2026
• ·Why I swore off starting businesses
• ·Lessons learned from failed startups

I've Run 75+ Businesses. Here's Why You're Chasing the Wrong Idea.

• ·Why boring businesses beat sexy ideas
• ·How I lost $10 million
• ·Using AI to automate my work

Why We Hate Agencies – Andrew Wilkinson on Burnout, Delegation & Building Tiny

• ·Why I hate agency life
• ·How I learned to delegate
• ·The shift from starting to buying businesses

The AI Automation Blueprint: From Barista to Billionaire

• ·How I automate my business with AI
• ·Why competition is increasing in software
• ·Building a $20 million AR business

Re-Up: I'm Worth ~$500M. Here's What I Regret Spending On

• ·Why I feel guilty about luxury spending
• ·What I regret spending my money on
• ·How I evaluate worth in purchases

How I Bought 35+ Businesses and Built a $240M HoldCo At 38

• ·Building a $240 million holding company
• ·Why I dropped out of journalism school
• ·How I started my first tech news site

From Barista to Billionaire (Mo Money Same Problems)

• ·Why money creates new problems
• ·Lessons from my barista days
• ·How I navigated my billionaire journey

Andrew Wilkinson: Never Enough? Barista → 40+ Businesses & Tiny

• ·Why I discovered I have ADHD
• ·How I built a business at 12
• ·Meeting Steve Jobs at 15

A Billionaire's Brutally Honest Advice if You Want Financial Freedom

• ·Why I value delegation in business
• ·The paradox of happiness in success
• ·My approach to financial freedom

How I Made My First $1M - The Andrew Wilkinson Story

• ·From barista to web designer
• ·Winning $25,000 business pitch
• ·Building a portfolio of 30 companies

Andrew Wilkinson On Going From A Barista To A Billionaire

• ·How I assess the AI investment landscape
• ·Why I focus on community-driven businesses
• ·The importance of quick payback periods

It's Easy to Spend but Hard to Spend Well

• ·Why I chartered a €200K yacht
• ·Owning multiple homes as a job
• ·How I approach spending wisely

Andrew Wilkinson Interview (for Never Enough Podcast)

• ·Why I interviewed Derek Sivers
• ·Lessons from my memoir Never Enough
• ·How I built my personal brand

A Masterclass On Hiring A CEO To Run Your Company

• ·How I hire CEOs for Tiny
• ·My biggest hiring mistakes
• ·Why I prioritize cultural fit

How I Lost $10,000,000

• ·How I lost $10 million
• ·What I learned from failure
• ·Why I kept going after loss

From Barista to Billions

• ·How I went from barista to billionaire
• ·Building a 40+ company conglomerate
• ·Why I dropped out of college

DTC Archive: Tiny's Andrew Wilkinson: Hero's Journey from Barista to Empire Builder

• ·Why I prefer bootstrapping over VC
• ·Acquiring AeroPress and its significance
• ·Lessons learned from hiring and firing CEOs

Andrew Wilkinson's $20,000 to $260,000,000 Story

• ·How I grew my portfolio to $260 million
• ·Why I prefer boring business strategies
• ·Meeting Charlie Munger and its impact

VTJ Live with Sahil Bloom and Andrew Wilkinson at the Vancouver Playhouse

• ·Strategies for scaling my companies
• ·Escaping the daily grind
• ·Leveraging frameworks for success

Andrew Wilkinson: $100M Yacht Party, Recent Investments & More Billionaire Sh*t

• ·Why I invested in Twitter experiments
• ·How I built MetaLab's profitability
• ·Insights from billionaire conversations

Why Is Andrew Wilkinson Monetizing His Twitter Followers?

• ·How I make $800,000 on Twitter
• ·Why I started Tiny from MetaLab profits
• ·What I learned from billionaires recently

Andrew Wilkinson - Co-Founder, Tiny

• ·Building Tiny's diverse portfolio
• ·Lessons from my memoir 'Never Enough'
• ·Navigating challenges in startup investments

Lessons in Life and Business from a Self-Made Billionaire

• ·Why I merged Tiny with WeCommerce
• ·How I learned from selling my first business
• ·Why bootstrapping shaped my investment strategy

Getting Rich Quick Sucks - How to Get Rich Slow

• ·Why getting rich slow is better
• ·My case for cash-flowing businesses
• ·Lessons from compounding wealth

The Hardest And Easiest Businesses To Start

• ·Ranking hardest businesses to start
• ·Why I love SaaS models
• ·The appeal of consumer brands

How To Prepare For The Economic Collapse

• ·How I prepare for economic downturns
• ·Why I'm holding cash for acquisitions
• ·My thoughts on renting versus buying homes

Building an Empire

• ·Lessons from acquiring 40 companies
• ·Why I stopped chasing happiness
• ·Understanding mimetic desire in business

Why You Need A Digital Detox with Andrew Wilkinson

• ·How I manage tech addiction
• ·Why I embrace creative boredom
• ·Building my personal board of advisors

Tiny Goes Public & How to Structure a HoldCo

• ·How I structured Tiny going public
• ·Why I paid $50,000 for lunch with Bill Ackman
• ·My partnership journey with Chris Sparling

Andrew Wilkinson: Investing vs. Operating, De-risking Leverage, and The Best Part About Business

• ·How I de-risked leverage in business
• ·Why I prefer operating over investing
• ·The best part about running companies

Andrew Wilkinson (founder of Tiny Inc. and co-founder of WeCommerce) - The Worst Job in the World

• ·Why I call running an agency terrible
• ·My worst job at McDonald's
• ·How bad jobs build character

Tiny Office Hours - Episode #3 with Shane Parrish

• ·Why I value networking in business
• ·How I approach cold emailing
• ·The challenges of operating a holding company

The Secretive Billionaire Who Acquired Burger King

• ·Why I launched a local news business
• ·The secretive billionaire who bought Burger King
• ·How I grew MetaLab into a multi-million dollar agency

Buying Wonderful Internet Businesses with Andrew Wilkinson, Founder of Tiny

• ·Why I focus on wonderful businesses
• ·My investment thesis at Tiny
• ·How I evaluate fair prices

How One Man Started 5 Billion Dollar Companies

• ·Why I admire Brad Jacobs' strategy
• ·How I define different entrepreneur types
• ·Why boring businesses can thrive

Co-Founder of Tiny Capital

• ·How I source investment opportunities
• ·My approach to company diligence
• ·Why I believe in compounding growth

Andrew Wilkinson - Tiny Capital

• ·My journey from designer to investor
• ·Taking WeCommerce public journey
• ·Lessons learned from building Tiny

Andrew Wilkinson on Bringing the Buffett Approach to Startups, WeCommerce, Slack & More

• ·Why I bought Dribbble and Girlboss
• ·The Slack design story
• ·How I built Tiny with profits

The Next Warren Buffett

• ·Why I compare myself to Buffett
• ·The discipline behind Tiny's compounding
• ·How I built my investment strategy

Building The Internet's Berkshire Hathaway, Going Public & Munger's Mental Models

• ·Why I built my own Berkshire Hathaway
• ·Going public via SPAC
• ·Learning inversion from Charlie Munger

Andrew Wilkinson's Tiny Tech Empire

• ·How I acquire internet businesses
• ·Why my holding company strategy works
• ·The importance of operational excellence

The 2020 MFM Award Show

• ·Co-hosting the 2020 MFM Award Show
• ·Why I love year-end reflections
• ·Memorable moments from the awards

Becoming an Entrepreneur with Andrew Wilkinson

• ·Bootstrapping MetaLab from scratch
• ·Building Tiny as a holding company
• ·Finding meaning in entrepreneurship

Pomp Podcast #427: Andrew Wilkinson on Why He Buys Certain Companies

• ·Why I love buying service businesses
• ·How I built MetaLab from scratch
• ·The importance of launchpad businesses

How Tiny Capital Created a Portfolio of Companies Doing >$100M A Year

• ·Building Tiny on my own terms
• ·Creating a $100M revenue portfolio
• ·Leveraging agency cash flow effectively

The Warren Buffett of the Internet Returns

• ·The Warren Buffett of the Internet thesis
• ·Why I invest in long-term businesses
• ·Lessons from my third MFM appearance

Could Joe Rogan Make More Money Without Spotify? Andrew Wilkinson on Subscriptions vs Ads

• ·Why I believe Joe Rogan got ripped off
• ·The value of subscription over ads
• ·How Howard Stern's deal changed podcasting

How the No Code Movement Helps Ideas Grow into Profitable Businesses

• ·How I built Tiny's website in 24 hours
• ·Why I love the no-code movement
• ·My investment in Flytographer's growth

Tiny Capital Co-Founder Describes the Venture Capital Graveyard and How the VC Industry is Changing

• ·Why I see venture capital as addiction
• ·Buying Meteor from Andreessen Horowitz
• ·How I help businesses become sustainable

Pomp Podcast #306: Andrew Wilkinson On Building Profitable Businesses With No Funding

• ·Building a portfolio of 25 companies
• ·How I transitioned from agency to investor
• ·Why I prioritize founder-led businesses

Berkshire.com: How Tiny Is Building The Berkshire Of The Internet

• ·Why I buy profitable internet businesses
• ·Closing deals in 15-30 days
• ·How I got my MBA in high school

Q&A with Andrew Wilkinson, Co-founder of Tiny

• ·How I source deals for Tiny
• ·Why my portfolio includes Letterboxd
• ·The operating model behind Tiny

Buying Cash-Flowing Internet Companies

• ·Buying cash-flowing internet companies
• ·Starting job boards for revenue
• ·Building no-code projects for growth

Andrew Wilkinson's Lessons Learned From Building Tiny

• ·My worst job at McDonald's
• ·Why I want New Zealand-style businesses
• ·The importance of character-building jobs

Designing a New Way To Do Business

• ·How I optimized my life around saying no
• ·My evolution from designer to investor
• ·Why I focus on life profitability

How Andrew Wilkinson Bootstrapped a Multi-Million Dollar Design Agency (Part 1)

• ·How I bootstrapped my design agency
• ·Why I started with a tip jar
• ·Scaling from barista to CEO

How a Guy in Canada Built 3 Multi-Million Dollar Businesses by Age 30 (Part 2)

• ·Building MetaLab before age 30
• ·How I grew Flow to success
• ·Creating Pixel Union's business model

The Story Behind Andrew Wilkinson's Flow App

• ·Building the Flow app from scratch
• ·Lessons learned from shipping Flow
• ·How I approached task management design

Taking Small Smart Steps with Andrew Wilkinson, MetaLab

• ·How I design a business around my desires
• ·My early playbook for landing clients
• ·Why people fail in business

Andrew Wilkinson / MetaLab

• ·The original MetaLab story
• ·How I built my first company
• ·Lessons learned before Tiny existed

How Andrew Wilkinson went from cat furniture to a billionaire empire

• ·How I built Tiny without venture capital
• ·Getting diagnosed with ADHD at 37
• ·Why I stopped drinking

ANDREW WILKINSON: From Barista to Billionaire & Building The Berkshire of the Internet

• ·How I built my own Berkshire Hathaway
• ·Why I focus on anti-goals
• ·Taking Tiny public with a billion dollar valuation

How Tiny's Andrew Wilkinson is Building the Berkshire of the Internet

• ·Building the Berkshire Hathaway of the internet
• ·Why I prefer simple, predictable businesses
• ·How I found my first profitable venture

From Barista to Billionaire with Andrew Wilkinson from Tiny.com

• ·Why I believe AI increases competition
• ·Building a $20 million AR business
• ·How I automate people-dependent businesses

Tiny Ltd (TINY.V) – The IPO of Andrew Wilkinson

• ·Why I chose to IPO Tiny
• ·My approach to capital allocation
• ·Pitching Tiny to microcap investors

Andrew Wilkinson's Lessons Learned From Building Tiny

• ·My worst job at McDonald's
• ·How I built Tiny from MetaLab
• ·Lessons from acquiring Dribbble

Andrew Wilkinson - Buying Profitable Tech Businesses, Crypto's Future, Losing $10M

• ·Buying Pixel Union back for five times
• ·My $10 million loss story
• ·Taking WeCommerce public on TSX

Tiny Capital: Building the Internet's Berkshire Hathaway

• ·Why I consider Tiny a holding company
• ·How I built a diverse portfolio
• ·The importance of long-term investing

Interview with Andrew Wilkinson

My First Million Live Event With Andrew Wilkinson (Austin Part 1)

Live Q&A With My First Million + Andrew Wilkinson (Austin Part 2)