Andrew Wilkinson
Co-founder of Tiny
Andrew Wilkinson is the co-founder of Tiny, a holding company owning multiple internet and consumer brands such as Dribbble and AeroPress. Starting as a web designer, he has built a portfolio valued at nearly $300 million in annual sales while maintaining a focus on bootstrapping rather than venture capital.
Episodes (1)
Insights (10)
Easy Choices, Hard Life; Hard Choices, Easy Life
quotesAndrew shares the life motto he regularly relies on.
Tiny Created as Founder-Friendly Acquirer
case studies lessonsAfter a painful sale process, Andrew created Tiny to purchase companies like AeroPress and Dribbble in a founder-friendly way.
Bold Ask Led to Steve Jobs Meeting
case studies lessonsAs a 17-year-old blogger Andrew asked to interview Steve Jobs, got first in line at an Apple Store tour, and learnt that bold asks can pay off.
Funding Path Depends on Business Model, Not Growth Ambition
strategic thinkingDecide funding path by matching capital intensity and competitive moats rather than assuming bootstrap limits growth.
Boring Businesses Have Less Competition
strategic thinkingChoosing boring, unflashy sectors lowers competition and increases chances of building a profitable company.
Being the Buyer You Wish You Had
leadership perspectivesAndrewās philosophy is to act as the empathetic buyer he wished he'd had, avoiding the private-equity āsuitā mindset.
Entrepreneurs with ADHD Delegate to Compensate
strategic thinkingAndrew explains that entrepreneurs with ADHD can offset weak executive function by delegating tasks and putting robust systems around themselves.
Fish Where VCs Don't Go
strategic thinkingTarget markets too small for VC interest so you are not battling capital-fuelled competitors.
Success Is Choosing Your Own Game
leadership perspectivesSuccess can mean a calm, headphone-on craft life not billion-dollar domination, so choose your game deliberately.
Fish Where Fish Are, Not Where Fishermen Compete
strategic thinkingAndrew cites Charlie Mungerās rule of finding uncrowded, high-yield pondsāniches with few competitors and better margins.