In this episode, I talk with Brad Morehead, Partner and Head of the Business Services Fund at Shore Capital Partners, who has also been a CEO, a CFO, a business professor, and a founder who built and sold his own company. We talk about business models: why the way a company acquires and keeps customers tells you more about how to build it than the industry it sits in, and what that means when you can group companies across a portfolio of nearly 70 by model rather than by end market. Brad walks through how models evolve, from founder-led selling to professionalized sales and from break/fix work to recurring revenue, and how a future-state org chart, the right board member, and a new set of KPIs carry a company through that shift. He also shares the lesson from a mentor that he now teaches younger investors: when someone tells you an idea didn't work, ask why, because you cannot be wrong when you are asking a question. We close with his own experience being acquired by a buyer in the exact same industry with a completely different model, which he compares to trying to build something with Legos and an Erector Set.

Strategic Themes:

• Group companies by business model, not by industry, because a pest control business and a veterinary practice that both sell direct to consumers have more to teach each other than two companies that merely share an end market
• Draw the future-state org chart before you change the model, then design the transition structure, systems, and KPIs (attach rate, cross-sell, recurring revenue) that get you there
• Ask why when a founder says "we tried that and it didn't work," because the question gets you to the root cause, validates the person in front of you, and cannot be wrong
• Recognize the watch-outs that come with a model alongside its upside, because negative working capital or a subsidized customer acquisition model can let a company grow itself out of cash

Chapters:

1. 00:00 – Introduction
2. 02:00 – What a Business Model Actually Is
3. 05:29 – From Break/Fix to Recurring Revenue
4. 11:43 – The Power of Why
5. 14:40 – If I Gave You an Extra Million Dollars
6. 17:52 – Negative Working Capital Is a Good Thing, Until It Isn't
7. 19:40 – Legos and an Erector Set