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Travis Jamison shares his journey from serial entrepreneur to full-time investing in legacy businesses, explaining that while tech is great for building, it’s risky for investing. He allocates capital into small, decades-old businesses via search funds, independent sponsors, and roll-ups, aiming for diversification, steady cash flow, and multiple expansion.

Travis views AI less as a direct investment opportunity and more as a tool for operating businesses that are resilient to technological change. AI’s rapid evolution makes predicting its exact impact nearly impossible, so investors should approach private businesses with careful bet sizing, strong due diligence, and awareness of risks.

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

0:00.0	Welcome to the Money Tree Investing Podcast. Stock market, wealth, personal finance, value stocks, invest in your life. Hello, Smart Money Free Podcast listeners. Welcome to this week's show. My name is Kirk Chisholm and I'll be your host. So today I'm joined with Travis Jameson. How you're doing today, Travis? Yeah, fantastic, Kirk. Thanks for having me here.
0:21.7	Glad to having the show. Well, for those listeners who don't know you, tell us a bit about your
0:25.2	background, what you do. I've been a historically a serial entrepreneur. Created SaaS companies,
0:30.3	marketing agencies, e-commerce products, physical goods, health goods, communities, a little bit of
0:35.0	everything, no rhyme and reason. But then after some liquidity events,
0:38.5	I slowly shifted to more of like a capital allocator. So now I'm basically a full-time investor
0:43.6	who basically invest in the more boring businesses out there. I find that interesting.
0:48.3	You made your bread and butter in SaaS, e-com, all those things, and now you're into different
0:52.9	industries. What made you want to do that
0:55.8	as opposed to just going out and doing the same thing you're good at over and over again?
1:00.2	I think that if someone is building a business from scratch, there's a large argument to be made
1:07.0	to do it something related to tech. It's cheap to get off the ground. It's easier. You can scale
1:12.7	really quickly, but kind of notice that investing in those types of businesses is a very different
1:17.9	story. They can be disrupted somewhat easily. Three years can go by and the technology can change
1:23.0	and suddenly it's useless. So I think it's a great place to make money, but to invest, I'm not as convinced. So I want to deploy my capital that I've earned into companies that have been around for decades and will most likely continue to be around for decades while earning good returns along the way. That's kind of a strategy and it's going to be working pretty well. I've seen a lot of allocators, people who've had exits, and they'll come back and
1:44.8	they'll invest in angel investing, or they'll do the same thing over and over again, or they'll just
1:49.0	leave all together and just invest in passively and they can focus on other things. What makes you
1:54.7	want to keep in the game versus just doing something completely different? I think the game of
2:00.0	like business and investing is probably
2:01.5	the most fun game that exists. The money is nice, but past a certain point, it's kind of just
2:07.2	like a points game, right? It's just a fun thing to do. It's what my identity is tied with.
2:11.5	I would be kind of lost without it because I don't have anything to replace it really.
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Investing in Legacy Businesses Beats Chasing Tech Trends with Travis Jamison

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