The Decision That Comes Before the Deal
Every entrepreneur faces the same recurring moment: an opportunity appears, the pitch sounds promising, and the pressure to act quickly builds. I have been in that position dozens of times across accounting, hospitality, healthcare, and real estate. What I have learned is that the quality of the decision depends entirely on the quality of the questions you ask before you commit.
Too many investments fail not because the opportunity was bad, but because the decision-making process was rushed or incomplete. The best opportunities do not require you to abandon careful thinking. They reward it.
Does This Align With What I Already Know?
The first question I ask is whether the opportunity fits within my areas of competence. Diversification is valuable, but only when it builds on a foundation you understand. Investing in hospitality made sense because I had experience managing operations, understanding customer behavior, and working with franchises. Expanding into healthcare through Healthy Heart Clinic was a natural extension of my interest in community wellness and preventative care.
When an opportunity requires you to learn an entirely new industry from scratch while also deploying capital, you are compounding risk unnecessarily. That does not mean you should never enter a new field, but it does mean you need to be honest about the learning curve and whether you have the time, resources, and support to navigate it.
Can I Afford for This to Fail?
This question is not about pessimism. It is about reality. Every investment carries risk, and the goal is not to eliminate risk but to ensure that a failure would not destabilize everything else you have built.
I evaluate every opportunity against my existing obligations: family, ongoing businesses, existing debt, and long-term commitments. If a deal requires me to over-leverage or divert resources away from stable operations, it does not matter how attractive the return looks on paper. The downside is too high.
A good investment is one where success accelerates your progress and failure does not break you. Anything outside that range deserves serious reconsideration.
Who Else Is Involved?
People matter more than most business plans acknowledge. I look closely at who I would be working with: their track record, their values, and their approach to problem-solving under pressure.
Partnerships fail when expectations are unclear or when one party operates with a different definition of integrity. I have turned down financially sound opportunities because the people involved did not demonstrate the kind of discipline or transparency I require. Conversely, I have moved forward on deals that looked complex on paper because I trusted the people running them.
You cannot audit someone’s character in a due diligence report. You learn it through observation, conversation, and time. If you do not have that clarity, slow down.
What Problem Does This Solve?
Every successful business solves a real problem. If I cannot articulate what problem the opportunity addresses and who it serves, I do not invest.
This applies whether the opportunity is a new restaurant location, a real estate development, or a consulting engagement. The clearer the problem, the easier it is to measure whether the solution is working. Vague value propositions lead to vague results.
When I invested in Osmow’s franchises, the value was clear: accessible, high-quality food in neighborhoods with demand and limited options. When I founded the Truman Foundation, the focus was equally specific: long-term, sustainable solutions to poverty and lack of opportunity, not short-term relief. Clarity of purpose makes execution simpler.
Does This Move Me Toward My Long-Term Goals?
Short-term gains are tempting, but they are only worth pursuing if they do not distract from what you are building over the next decade.
I measure every opportunity against my long-term objectives: financial stability for my family, businesses that create value for others, and the ability to contribute meaningfully through philanthropy. If an investment does not advance at least one of those goals, it is not worth my time regardless of its profitability.
This filter has helped me avoid opportunities that were financially attractive but operationally draining or misaligned with my values. Opportunity cost is real. Saying yes to the wrong thing means saying no to something better.
What Is the Exit Strategy?
I think about exits before I enter. That does not mean I plan to leave quickly, but it does mean I want to understand how value is realized and under what conditions I would walk away.
For some investments, the exit is a sale. For others, it is operational maturity where the business runs independently. For philanthropic work, the exit is achieving a sustainable model that no longer requires my direct involvement.
Knowing how a commitment ends helps me evaluate whether it is worth beginning.
The Discipline of Saying No
The hardest part of investing is not finding opportunities. It is saying no to most of them. Every deal sounds good in a pitch. The difference between successful entrepreneurs and everyone else is the willingness to walk away when the answers to these questions are not clear.
I have passed on deals that later succeeded, and I have watched others struggle with investments I declined. Neither outcome bothers me. The goal is not to catch every opportunity. It is to commit only to the ones that fit your strategy, your capacity, and your values.
Discipline is what allows you to act quickly when the right opportunity does appear, because you have not overextended yourself chasing everything else.