🎙️ Podcast Notes: Andrew Wilkinson - I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea.
In this episode of Lenny's Podcast, Andrew Wilkinson, co-founder of Tiny, a holding company owning over 40 profitable internet and consumer brands like Dribbble and AeroPress, shares his journey from teenage barista to building a $300 million portfolio without venture capital. Having started or been involved in over 75 businesses, Wilkinson offers actionable insights on entrepreneurship, productivity, mental health, and the future of work. Below is a detailed breakdown of the key topics discussed.
1. Background and Journey
Andrew Wilkinson began his career as a teenage barista and web designer, eventually co-founding Tiny, often dubbed the "Berkshire Hathaway of the Internet." Tiny owns a diverse portfolio of over 40 businesses, generating nearly $300 million in annual revenue. Unlike many entrepreneurs, Wilkinson bootstrapped his ventures, avoiding venture capital, and at one point was personally worth over $1 billion. His story is one of starting small, learning from failures, and scaling through acquisition rather than relentless startup creation.
2. "Fish Where the Fish Are" – Finding Great Startup Ideas
Wilkinson’s core advice for entrepreneurs is inspired by Charlie Munger: "Fish where the fish are." This means targeting high-margin, low-competition niches rather than chasing oversaturated markets.
- Key Principles:
- Start Small: He compares entrepreneurship to weightlifting—beginners shouldn’t try to "deadlift 300 pounds" with complex ideas like AI startups. His first success, a web design agency (Metalab), was simple and provided immediate wins, building his confidence.
- Avoid Crowded Markets: Popular ideas like cafes or restaurants are tough due to high competition and low margins. Instead, he suggests "boring" niches like pest control or government form-filling software, where fewer people compete.
- Leverage Unfair Advantages: Wilkinson emphasizes aligning business ideas with personal passions and unique skills. For example, his background as a barista led to acquiring AeroPress, and his love for movies connected him to Letterboxd.
- Pitfalls to Avoid:
- Industries with repeated failures (e.g., bars, local news) often have structural challenges no amount of brilliance can overcome.
- "Sexy" ideas in hyper-competitive fields (e.g., project management software like his failed Flow venture) can burn cash against venture-backed giants.
- Practical Tip: Use AI tools like ChatGPT or Claude to analyze potential business models before committing.
3. AI-Powered Productivity Stack
Wilkinson has embraced AI to supercharge his productivity, replacing many tasks once handled by a human assistant. His "agent stack" includes:
- Lindy: A workflow automation tool managing his inbox and calendar.
- Filters unnecessary emails (e.g., archiving "cool, that works" replies).
- Labels time-sensitive messages for quick action.
- Drafts responses to simple queries (e.g., lunch invites) with multiple-choice options.
- Adds emojis to calendar events for visual clarity.
- Replit: A coding platform for rapid web development, allowing him to build projects solo in styles like Stripe’s design.
- Limitless: A wearable device recording his day, enabling queries like "What did I promise today?" or analyzing conversations (e.g., relationship disputes).
- Others: Claude for writing, ChatGPT for general tasks, and Gemini for large datasets (e.g., medical records).
These tools save time, reduce stress, and let Wilkinson focus on high-value decisions, showcasing AI’s practical impact on daily life.
4. Evaluating Companies with Buffett-Style "Moats"
Wilkinson shifted from starting businesses to buying them, inspired by Warren Buffett’s calm, deliberate approach. At Tiny, he evaluates companies in under 15 minutes using these criteria:
- Competitive Moats: Looks for advantages like strong brands (e.g., AeroPress) or network effects (e.g., Letterboxd’s film community) that ensure longevity and pricing power.
- Resilience: Prefers businesses "hard to mess up," with systems not reliant on one person.
- Lazy Leadership: Once acquired, Tiny leaves management intact, only replacing founders with CEOs if needed. He hires self-starters and avoids micromanaging.
- Management Insight: Wilkinson’s heuristic reflects his belief that fit trumps potential: "If I ever think ‘should I fire this person?’ I should do it immediately". CEOs must align with the business’s needs without needing heavy coaching.
5. When to Shut Down a Startup Idea
Wilkinson shares telltale signs an idea isn’t worth pursuing:
- Overcrowded Markets: If many have failed before (e.g., his pizzeria or bar ventures), structural issues likely persist.
- No Early Wins: Ideas needing massive upfront effort without quick validation (e.g., his $10 million loss on Flow) drain resources.
- Misaligned Passion: A business you’d hate running long-term (e.g., pressure washing unless scaled) becomes a job, not a venture.
He advises starting small, validating fast, and pivoting if the "fish aren’t biting."
6. Mental Health Journey: From Anxiety to Clarity
Despite his success, Wilkinson battled anxiety and ADHD, which money couldn’t fix. His turning points:
- Anxiety: Realizing success didn’t quiet his "nasty inner voice," he tried SSRIs in 2020. Within days, it turned "Times Square into a quiet library," offering relief no external achievement could.
- ADHD: Diagnosed after a cognitive test (despite skepticism), he found medication sharpened his focus. With 30% of entrepreneurs sharing this trait, he urges others to explore it.
- Reframing Wealth: He redirected wealth to philanthropy, reducing personal stress and finding purpose beyond accumulation.
Wilkinson advocates addressing mental health directly via medication or otherwise, over chasing external validation.
7. The Future of Work and AI Predictions
Wilkinson predicts AI will automate most knowledge work within five years, comparing today’s tools to the "Palm Treo phase" before an "iPhone moment" of accessibility.
- Impact: Jobs like research, admin, and even coding may vanish, but he’s optimistic about new roles in human connection (e.g., companionship, creativity).
- Advice:
- New Grads: Master AI tools now to build wealth and stay competitive.
- Workers: Adapt quickly, as "someone good with AI will replace you."
- Kids: Focus on socialization and passion; specific skills are unpredictable.
He sees a world of abundance where status might shift to soft skills like humor or pickleball prowess.
Closing Thoughts
Wilkinson’s conversation blends tactical business advice with raw personal reflection. His "fish where the fish are" framework, AI-driven productivity, and Buffett-inspired evaluation methods offer a playbook for entrepreneurs. His mental health insights and AI predictions challenge listeners to rethink success and adaptation in a rapidly changing world.
For those inspired, Wilkinson invites business sellers to contact Tiny and interesting folks visiting Victoria, Canada, to grab coffee.
Crepi il lupo! 🐺