An Entrepreneur’s Success Depends on the Quality of Their Questions

What I Learned From My First Months as a Paid Coach

When I decided to get into coaching entrepreneurs, I had some high-minded ideas on how I wanted to help. I learned that what I think they need and what they need are two different things. I thought they needed holistic advice on business, family, and faith. After all, it is clear to me these three elements are closely interrelated.

What entrepreneurs need is someone who can help them grow their business. This doesn’t mean I was wrong on the holistic approach, but unless I can help them grow their business, they don’t have time for anything else.

This idea of being a coach intrigued me.

I saw myself as the wise, grey-haired man sitting in his easy chair by the fire, pipe in hand, doling out pearls of wisdom. I pictured entrepreneurs saying, “That was amazing. Thanks for that wonderful bit of wisdom. You changed my life.”

What I found was something I really already knew: entrepreneurs are busy. They aren’t looking for wisdom. They are looking for answers. Sometimes they simply need to start asking the right questions so they can discover the thing that is inhibiting their company’s growth.

The key is to define and decide.

This is where I’ve been a big help. So much is coming at entrepreneurs, they often can’t seem to define the problem they are trying to solve. Caught in a busy loop, they waste lots of time.

They are working hard every minute of every day but sometimes aren’t sure they are working on the right thing. This leads to working on everything. There are so many problems to be addressed, they can’t see the forest for the trees.

This is where they’ve told me I’ve helped.

I bring focus. I help define the problem. Then I bring experience to the solution. Here are a few of the needs I’ve helped entrepreneurs address:

  1. Defining their ideal business prospect.
  2. Succinctly describing the problem their business solves.
  3. Figuring out where the leverage is in the sales channels.
  4. Moving an entrepreneur from inside focused to outside focused.
  5. Building meaningful market relationships.
  6. Finding and hiring top performers.
  7. Understanding their market’s dynamics and their interdependencies.
  8. Knowing when to raise money. How to do it. How to structure a deal which will be attractive to investors.
  9. Showing how to get to profitability and sustainability sooner rather than later.
  10. Building value while building a business versus simply enjoying cash flow.
  11. Teaching how to present their company for sale or investment or how to close a deal.
  12. Getting the company’s message right in a speech, website, or conference.

The holistic conversations happen.

The conversations happen in the midst of defining and solving entrepreneurial problems. I’m not a shrink, and I’m not a pastor. I’m a businessman and investor. I understand entrepreneurs. I know how they think and how they process. I instinctively know what they want and see the shortfalls in how they are going about trying to get it.

They create something from nothing.

I love entrepreneurs. They are my favorite people. They see the unseeable in the market they address. I’m drawn to them. I get them. I’ve worked with entrepreneurs my whole life. I want to find ways to use my experience to help them achieve their goal of growing their company.


My coaching rates are between $1,500 to $10,000 per month with a six-month initial commitment, followed by quarterly commitments. The rate is based on your expected return on investment. Generally speaking, the bigger the business, the more there is to work with, the higher the leverage, and the higher the fee.

If this is something you would like to explore, email me at and put “Coaching Relationship” in the subject line. I have 2 coaching slots left.