Ranking The Best And Worst Businesses To Start w/ Billionaire Investor Andrew Wilkinson (#386)

About this video

Andrew Wilkinson joins Sam and Shaan to discuss his journey building and investing in internet businesses, from early ventures like Pixel Union to his current holding company Tiny. He shares lessons from failed experiments (e-commerce, restaurants) and successful acquisitions, explains his philosophy on business difficulty rankings, and introduces Tenzing, a new investment bank he’s launching for bootstrap founders.

Key takeaways

• Andrew moved from thinking he knew nothing about investing (2014) to building expertise in eight years by obsessively reading Warren Buffett and value investing books, demonstrating that intensive focus over time can take you from bottom to top of an industry
• Different business models have vastly different difficulty levels—brick-and-mortar and physical goods businesses with many employees are hardest, agencies are medium, and asset-light software businesses like job boards are easiest because they scale with minimal overhead
• Warren Buffett’s 1972 letter to See’s Candy CEO reveals he was deeply operational and detail-oriented about merchandising, store design, and marketing psychology, not just a passive capital allocator—he actively influenced businesses to create value
• Andrew’s failed ventures (e-commerce furniture, restaurants) taught him as much as his successes by showing him what brutal businesses look like, which helped him recognize quality businesses later—luck played a role in surviving early failures rather than abandoning entrepreneurship altogether
• Tenzing, Andrew’s new investment bank venture, aims to help bootstrap founders access capital, do M&A, and understand financing options they didn’t know existed (like R&D tax credits), filling a gap where traditional investment bankers won’t work with smaller businesses

Episode details: published November 17, 2022 · 197K views · 1:25:09 long. Summary written by Self Growth Videos from the episode itself. The business ideas, figures and results discussed are the hosts’ and guests’ own claims, shared as brainstorming and entertainment — not verified facts and not investment advice.

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