- Travis Jamison transitioned from serial entrepreneur to full-time investor after several liquidity events.
- He avoids investing in tech startups due to disruption risks despite believing they’re great for building wealth.
- His capital allocation focuses on small, boring, decades-old businesses that are hard to kill and generate steady returns.
- He participates in search funds, independent sponsor deals, and roll-ups, rather than angel or venture investing.
- He targets companies in the $4–30 million enterprise value range, often in industries like HVAC, pool services, and rehab centers.
- Roll-ups allow him to buy add-on companies cheaply, combine them, and benefit from multiple expansion.
- He diversifies across industries to avoid concentration risks and aims to build a portfolio of around 30 small businesses.
- He sees the lower middle market as more attractive than larger private equity deals due to lower entry multiples.
- He views business as the most fun game to play and continues investing for identity and enjoyment, not just money.
- For AI, he invests in companies largely unaffected by it, seeing boring businesses as safer than trying to pick AI winners.
- AI should be viewed as a powerful leverage tool, allowing individuals and businesses to achieve far greater output with fewer resources.
- Blue-collar industries like HVAC, plumbing, and construction are less exposed to AI disruption in the near term, making them relatively safer sectors.
- Many companies deliberately keep their AI use quiet to avoid tipping off competitors or losing their edge.
- Because the long-term trajectory of AI is unpredictable, investors should avoid over-concentration and treat exposure as part of a balanced portfolio.
- The most effective strategy is to swing at the “easy pitches”—investments with clear fundamentals—rather than forcing deals in uncertain or hype-driven areas.
For more information, visit the show notes at https://moneytreepodcast.com/investing-in-legacy-businesses-travis-jamison-746