Coaching for Coaches is a High Yield Investment

What do you think of when you hear the term “moneyball”?

Do you think of the Michael Lewis book? Do you think of the actually quite good movie they made with Brad Pitt?

Do you draw a blank (please don’t)?


In my re-emergence into entrepreneurship I’ve had to wade back into social media vectors I hoped to never touch again. I’m guessing because I’m (almost) 40 and have two kids, I’ve been targeted for all sorts of influencers in “investing”.

I find myself almost always making the same critique. Most of the “genius” investing strategies are sort of reverse engineered. So, for example, trust this guy because he invested in Google when people were like “what’s a search engine?” or trust another person because he got in on Apple in the 1990s when it seemed like everyone but my family thought they were going out of business.

It’s weirdly designed for a social media environment where clout is built around having a lot of “followers”. But if an overwhelming amount of people follow something, does it turn out to be a buy low sell high proposition for most of them? By sheer probability, it does not.

So here’s my pitch, based off the podcast I recorded earlier this week with Trever Gray. If you are a coach, and want to make the biggest positive impact on your team, yourself and your family, invest in some coaching.

Right now, if you get into private coaching, that’s not where the money is. Coaches, for the most part, are not wealthy people. They are not thinking about investment in themselves because it doesn’t seem like an option.

Earlier this year I debuted a six week coaching module for coaches. I asked one coach how much they would have otherwise spent on themselves had they not forked over the $210 for my course. The answer is all too obvious: nothing.


My favorite author Nassim Nicholas Taleb has a saying that goes something like this:

Never ask a doctor what you should do. Ask them what THEY would in your situation.

Never ask a chef what’s good on the menu, ask what they eat.

Basically, don’t trust decisions that other people tell you to make, figure out what decisions they make when they have skin in the game.

So you might read what I’m writing here as a bald plea to hire me to be your coach. To be honest, I’m pretty confident that I’ll be full up coaching on that front sooner rather than later, regardless of whether anyone reads this blog.

So instead I’m offering free advice. It’s not advice that I think you should do, I’ll tell you what I DO. I invest in coaching for myself.

Before I had even turned the page and devoted myself full time to this business in January 2023, I had already hired not one, but two coaches to help me. Before I’d cashed a single check for anything Chris DeSantis coaching related, I had committed nearly $10,000 in investment to something that I would never be able to quantify with an earnings statement.

The first person I hired was Nikki Kett, without whom I can’t even imagine how the launch of my business would have gone without. The coaching she has provided me in terms of emotional management paid for themselves in real time.

The branching possibilities from the progress I made with Nikki mean that I expect to reap many times what I paid over the course of my career. Not to mention the unquantifiable value to my relationships with my wife, my children and the people I work with.

The second person I hired is Sherri Fisher. Sherri is probably less familiar to people within the swimming world. I reached out to Sherri for help after I finally, fully admitted to myself that I was struggling with ADHD.

Sherri has a made a career out of helping people “like me”. I walked away with a completely different understanding of how I could make the way I’m wired work for me. In essence, take the positivity that I had in the video above and multiply it by a factor of ten and you might approximate what I consider the opportunities from my “learning disability”.

So don’t take my advice to hire coaching because you think it’s what I want you to do. It’s what I did, it’s what I plan on doing for the future, even though I didn’t “know” what the exact dollar and cents payoff for me was going to be.

Ultimately if you’re coaching you’re part of an organization that is investing in the experience for athletes in your program. There has been an explosive growth in people who will bring consultant-coaches in to work with athletes on their team.

Only a smart few are getting where the real biggest opportunity is, however. Coaches are a force multiplier. Investing in coaching is the “Moneyball” investment of our time for coaches everywhere. Go where everyone else is going to want to go, when the opportunity is cheap and available.