Andrew Wilkinson

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 $300 million in yearly sales (and he was personally worth over $1 billion at one point)—all without ever raising venture capital.

7 skills 10 insights

AI & Technology Skills

The long-term trajectory of AI suggests a shift toward 'omniscient' agents that can manage entire business functions, potentially displacing traditional knowledge work.

"I think the fundamental question is, do all jobs just become a single prompt? For example, does a CEO just grow the business while making the customers happy and turning a profit... and it is able to..."
58:43

AI agents can replace high-level administrative functions by creating complex, automated workflows for email, scheduling, and research.

"I have just basically tried to take every single thing a human could do in my inbox and automate it with Lindy... It's like having the world's most reliable employee who costs $200 a month and works 2..."
43:10

Modern AI coding tools allow non-technical founders to build and deploy functional web applications through natural language 'vibe coding.'

"Replit is basically a vibe coding platform. You can literally go into it and say, 'I want to make a website for my sound software business... and it'll go and design a pretty impressive website. But t..."
48:08

When evaluating consumer robotics or hardware, look for products that utilize advanced machine vision and 'Waymo-style' engineering rather than basic sensors.

"I finally got one that actually works. It's called the Matic Vacuum... basically, I think it's like former Google Engineers basically built like a mini Waymo car. So it has machine vision and it will..."
01:23:16

Hiring & Teams Skills

Interviewing for senior roles should focus on finding natural alignment between the candidate's 'default' strategy and the business's actual needs.

"To a man with a hammer, everything looks like a nail... I want to be nodding along. I want to go, that's exactly what I would do or that's way smarter than my idea. And then I just leave them alone be..."
39:39

Doubt is a powerful signal in hiring; if you are questioning a candidate's long-term fit, they are likely not the 'superstar' you need.

"The kind of heuristic I have is if I ever think, should I fire this person even once, I should fire them immediately. It has always been a signal, at least for me, that when someone's a superstar, I c..."
38:12

Leadership Skills

Effective leadership involves identifying your 'superpower' and aggressively delegating everything else to avoid being trapped in a 'job' rather than a business.

"I think they really need to lean into what I call lazy leadership, which is how do I get away from the things I hate as quickly as humanly possible? How do I be Teflon for tasks?"
11:26

Micromanaging or forcing ideas on leaders leads to poor execution; true delegation requires letting the person in charge own the strategy.

"I've also found people will shoot themselves in the foot. If I tell them an idea in a board meeting and I say, 'I really need you to try this,' it never works because usually they sandbag it... They w..."
41:06

Product Management Skills

The most profitable businesses are often found in unglamorous niches where high demand exists but competition is low, preserving margins.

"Charlie Munger, Warren Buffett's longtime business partner, has this amazing quote. He says, 'Fish where the fish are.' And he gives this example, he says, 'If you're a fisherman and you see a large p..."
06:26

A space littered with 'dead bodies' (failed startups) usually indicates a fundamentally flawed business model that even great execution cannot fix.

"The biggest mistakes I've made have been going into business models where other people have repeatedly failed and thinking, I can do this better... you can't take a brilliant management team and chang..."
23:37