Tiny Created as Founder-Friendly Acquirer

Situation

Andrew Wilkinson had previously sold a business and found the experience extremely negative
He encountered private equity buyers who were disconnected from founders' experiences - describing them as "douchebags" who "showed up in our office in suits" using terminology founders didn't understand
This negative experience created a gap in the market for a more founder-friendly acquisition approach
Andrew had already built successful businesses and had capital to deploy in a different way

Founded Tiny (Tiny.com) specifically to become "the buyer we wish we could have sold to"
Established a philosophy of minimal interference with acquired companies
Developed a clear acquisition thesis focused on businesses with competitive advantages that would endure
Implemented a hands-off management approach: "When Tiny buys a company we generally just leave them alone"
Maintained existing management teams whenever possible: "If they already have management in place we say nothing changes"
Created a policy where "no one should know that we've even bought them" - preserving company culture and operations

Acquired companies with strong moats, particularly focusing on network effects and strong brands
Purchased companies across various sectors including:
- Dribbble (design social network)
- Letterboxd (film review social network)
- AeroPress (coffee maker)
- Serato (DJ software)
Bootstrapped the business "from zero to hundreds of millions of dollars in value"
Grew to own approximately 40 businesses

Successfully scaled to nearly $300 million in revenue across portfolio companies
Built a holding company often called "the Berkshire Hathaway of the internet"
Created an alternative exit path for founders who want their companies to continue operating with minimal disruption
Established a reputation as a founder-friendly acquirer
Maintained the unique cultures and operations of acquired businesses
Demonstrated that bootstrapped companies can reach significant scale without venture capital

Solve your own pain point: Andrew created the solution he wished existed when selling his own company
Minimal interference maximizes value: The hands-off approach preserves what made acquired companies successful
Focus on sustainable competitive advantages: Look for businesses with "moats" like network effects or strong brands that are "hard to mess up"
Founder empathy creates differentiation: Understanding founders' concerns creates a competitive advantage in acquisitions
Management continuity preserves value: Keeping existing teams intact maintains operational excellence
Acquisition criteria clarity: Having specific parameters (happy customers, happy employees, competitive advantages) creates focus
Long-term holding creates different incentives: Unlike PE firms seeking quick exits, a permanent holding strategy allows for different decision-making