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

In this special episode, co-hosts Sean and Sam give a warm introduction to Andrew Wilkinson, founder of Tiny—an investment and holding company that owns ten different software companies. Following Andrew's popular previous appearance, this episode is a unique 'Ask Me Anything' format where listeners can directly engage with him.

Andrew discusses his approach to finding reliable CEOs for the companies they acquire. He primarily uses his network, seeking recommendations from existing executives who understand the market. The ideal CEOs are those who have previously succeeded in similar roles, ensuring they can replicate success without needing extensive oversight.

Andrew shares his admiration for Warren Buffett and Charlie Munger, highlighting Munger's 'lattice work of mental models' as particularly insightful. He encourages listeners to read Buffett's writings, claiming they offer invaluable lessons in business and investing.

While starting a business can feel like 'black magic', Andrew asserts that growing companies relies on established processes and best practices, particularly in marketing and pricing strategies. He stresses the importance of effective incentives for driving employee performance.

Andrew provides recommendations on business biographies that have shaped his thinking. Notable mentions include 'Shoe Dog' by Phil Knight and 'Buffett: The Making of an American Capitalist' by Roger Lowenstein. He emphasizes that these books reveal the hard realities behind success.

Reflecting on his experience with a failed restaurant venture, Andrew emphasizes the unanticipated challenges of the food industry, such as slim margins and high employee turnover. He contrasts this with the tech sector, where he now finds more satisfaction and understanding.

Andrew values 'scrappiness' in candidates, looking for individuals who drive projects forward with urgency and creativity. He notes the importance of pairing dynamic individuals with those capable of steady follow-through.

Despite residing in Victoria, Canada, Andrew finds ways to connect with entrepreneurs outside typical tech hubs through local networks and strategic cold emails. He emphasizes that common entrepreneurial challenges unite all business types.

Andrew reveals that most of his investments come from personal capital, but he is exploring opportunities to raise a fund to tackle upcoming market opportunities. He discusses the balance of investing with a deep understanding of business.

Andrew critiques the conventional advice of taking risks in one's twenties, advocating instead for investments with stable returns. He encourages aspiring entrepreneurs to seek profitability and consistency in their ventures.

Andrew concludes by reflecting on life lessons regarding happiness derived from relationships and community rather than material possessions. He highlights the importance of lifelong learning and adaptability.