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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

quotes

Andrew shares the life motto he regularly relies on.

1h 23m

Tiny Created as Founder-Friendly Acquirer

case studies lessons

After a painful sale process, Andrew created Tiny to purchase companies like AeroPress and Dribbble in a founder-friendly way.

1h 26m

Bold Ask Led to Steve Jobs Meeting

case studies lessons

As 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.

1h 24m

Funding Path Depends on Business Model, Not Growth Ambition

strategic thinking

Decide funding path by matching capital intensity and competitive moats rather than assuming bootstrap limits growth.

25m

Boring Businesses Have Less Competition

strategic thinking

Choosing boring, unflashy sectors lowers competition and increases chances of building a profitable company.

20m

Being the Buyer You Wish You Had

leadership perspectives

Andrew’s philosophy is to act as the empathetic buyer he wished he'd had, avoiding the private-equity ā€˜suit’ mindset.

1h 26m

Entrepreneurs with ADHD Delegate to Compensate

strategic thinking

Andrew explains that entrepreneurs with ADHD can offset weak executive function by delegating tasks and putting robust systems around themselves.

1h 18m

Fish Where VCs Don't Go

strategic thinking

Target markets too small for VC interest so you are not battling capital-fuelled competitors.

30m

Success Is Choosing Your Own Game

leadership perspectives

Success can mean a calm, headphone-on craft life not billion-dollar domination, so choose your game deliberately.

28m

Fish Where Fish Are, Not Where Fishermen Compete

strategic thinking

Andrew cites Charlie Munger’s rule of finding uncrowded, high-yield ponds—niches with few competitors and better margins.

5m