Most people play Monopoly to win. Entrepreneurs play it to survive long enough to control the board. Cheryl LaTray, founder of LaTray Unlimited, sees business ownership the same way. It is not about one lucky move. It is about positioning, patience, and knowing when to take a calculated risk instead of sitting on the sidelines.
Cheryl’s perspective comes from years of real world experience making decisions where comfort was rarely an option and flexibility was often the advantage.
Here is what business owners can learn from how she plays the game.
1. Entrepreneurs Think Several Moves Ahead
Cheryl does not look at today’s deal in isolation. She looks at how it affects the next five decisions.
“You cannot just think about the property you are buying. You have to think about what it allows you to do next.”
Many business owners get stuck reacting. Cheryl plans. She understands that short term discomfort can unlock long term leverage.
2. Cash Sitting Still Is Not Always Safe
In Monopoly, holding cash feels comfortable. In business, it can quietly hold you back.
Cheryl believes money should have a purpose.
“Sometimes the biggest risk is doing nothing because you are afraid to make the wrong move.”
Entrepreneurs who never deploy capital miss opportunities that never come back around.
3. Flexibility Beats Perfection
Cheryl has pivoted more times than she can count. Market shifts, personal changes, unexpected challenges. None of them followed a script.
“You have to be willing to change the plan without panicking.”
She treats pivots as strategy adjustments, not failures. The goal stays the same even when the path changes.
4. Comfort Is Expensive
One of Cheryl’s strongest beliefs is that comfort has a hidden cost.
“If everything feels safe, you are probably not growing.”
Entrepreneurs who protect comfort too aggressively often limit their upside. Growth usually requires stepping into uncertainty before clarity shows up.
5. Know When to Buy, Hold, or Walk Away
Not every opportunity deserves a yes. Cheryl is disciplined about choosing when to move and when to pass.
She evaluates:
- Timing
- Downside risk
- Long term leverage
- What the opportunity unlocks next
“Sometimes walking away is the smartest move you can make.”
6. Risk Tolerance Is a Skill
Cheryl does not believe people are born with high risk tolerance. She believes it is developed.
“You build tolerance by making decisions and living with the outcome.”
Each move builds confidence and clarity for the next one.
7. The Goal Is Control, Not Flash
In Monopoly, flashy moves often lose. Control wins. Cheryl applies the same thinking to business.
“The goal is not to look successful. It is to stay in the game long enough to win it.”
That mindset shapes how she builds, invests, and plans for the long term.
Key Takeaways
- Entrepreneurs must think several moves ahead
- Cash comfort can limit growth
- Flexibility is more valuable than perfect plans
- Risk tolerance is built through action
- Walking away can be a strategic win
- Long term control beats short term excitement
📩 Connect with Cheryl LaTray
Company: LaTray Unlimited
LinkedIn: Cheryl LaTray
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