First Stage Investor

New Pick: Invest in the Future of Sports Coaching

New Pick: Invest in the Future of Sports Coaching
By Teddy Lyons
Date March 30, 2023

In the article


Valuation $15,000,000
Total Raised $445,923

Golf is my favorite sport. There is nothing better than teeing it up early on a Sunday morning. 

But here’s the problem. I’m pretty bad. And unless you’ve put in an enormous amount of time to develop your game, you are probably pretty bad too. 

Golf is an incredibly technical sport that requires expensive lessons and equipment to improve. (If you want proof that pure “athleticism” won’t make you good at golf, check out NBA great Charles Barkley’s swing.)

Despite the difficulty of the game, golf’s popularity is skyrocketing. In 2020, the number of golfers in the U.S. grew by 2% — the largest increase in 17 years. And by the end of 2020, there was a 14% increase in rounds recorded — the highest gain since 1997. 

Golf has also attracted a whole new demographic of players, particularly Gen Z. A recent study showed that Gen Z and younger millennials make up 27% of new golfers every year. The generations that grew up with smartphones and social media are picking up golf in droves.

Capitalizing on this shift is Skillest, a remote golf-coaching app with hundreds of qualified coaches providing high-quality video lessons. 

Using Skillest is simple.

  1. First you filter for coaches through the app’s search tool. You can select coaches who are based near your location or in a different country. You then send a recording of your swing to your coach.
  2. Your coach will respond with a screen recording of your swing, drawing lines and indicating where your swing issues lie.
  3. Your coach will then film themselves on the range showing you exactly what drills you need to be working on and what you should be feeling in order to improve.
  4. You record yourself working on the drills and post them back to the app.
  5. Your coach will then message you on whether you are performing the drill correctly or need to tweak it.

I got a lesson from Keith Bennett, a golf coach from Scottsdale. And I can confidently say that I have found my lifelong coach. My swing has improved DRAMATICALLY, and I’ve never felt better about my game. 

I can testify that this app is phenomenal from a customer standpoint.

But do coaches like it?

In short, absolutely. 

Most of the coaches on the Skillest app are PGA professionals. This means that many of them have coaching jobs at country clubs. So users get to learn from trained professionals who teach golf for a living. And Skillest allows coaches to make thousands of extra dollars per month with little additional effort. And the best part? Coaches can set their own prices. 

If a coach is just starting out on Skillest, they can set low prices to attract new golfers. If a coach is well known or has a large social media following, they can set higher prices. 

This freedom has led to something remarkable. Without any nudging from Skillest, coaches are promoting Skillest to their in-person clients and social media pages. 

My coach has a very active Instagram page with more than 100,000 followers. He is constantly posting and promoting Skillest to his following and continuing to draw in new customers. Coaches are acting as the sales force for Skillest, and the benefit for Skillest is enormous. Coaches are providing close to $5 million in free advertising per year. 

Without spending much on marketing, Skillest is projecting its customers will spend more than $4.5 million on the platform in 2023. Last year platform spend was $2.7 million. There are more than 200 coaches on the platform who have at least one paying customer, and this number continues to grow. Between 2,000 and 3,000 new users make an account on Skillest every month. And platform spend by Skillest customers has been growing steadily year over year. 

So how does Skillest make money? 

It takes 15% of the fees from each transaction. Additionally, coaches are charged $49 per month for using the platform. Given how much coaches make on the platform, they have not pushed back whatsoever on being charged this nominal amount. 

Market Upside

So we know that coaches love the platform and are continually bringing in new customers. Now we must look at Skillest from an investor perspective.

The company is raising at a $15 million valuation. So, accounting for dilution, the company must exit for around $250 million for us to easily see a 10x return (the minimum we look for as startup investors). 

In my eyes, the company needs to get to $100 million in platform spend to make this possible. How will it get there? Let’s do some back-of-the-envelope math.

There are 50,000 teaching pros worldwide. Each coach on Skillest brings in $10,000 in platform spend on average. If Skillest can bring in 20% of those teaching pros, the company will hit $100 million in platform spend. That doesn’t include the $5.9 million Skillest would earn from the $49 monthly coach fee. 

For most two-sided marketplaces, I would consider this highly improbable. There is a company called Hidrent that offers handyman services performed exclusively by firefighters. If you told me that that company needed to get 33% of firefighters on the platform, I would say that is impossible.

But the golf community is different. Golf pros are at the golf course teaching golf from 9 to 5. Afterwards, they are free to do as they please. With an additional couple of hours per day teaching golf remotely, they can make thousands of extra dollars per month. 

This is simply a no-brainer in every sense of the word, and I strongly believe that Skillest can get there through aggressive marketing and search engine optimization. Its current Wefunder raise will help the company do just that. 

Skillest can get to $100 million in platform spend on golf alone. But the company has bigger plans. Due to popular demand, the company will add tennis, swimming, baseball, and basketball to the platform in the near future. A successful launch of new sports will easily get the company to $100 million in platform spend. 

I spoke to CEO Brian Park twice and asked him every question in the book about Skillest. He co-founded Yahoo! Messenger and clearly has a knack for scaling disruptive technologies. I strongly believe in him and his ability to move Skillest in the right direction. 

If you want to invest in the future of sports coaching, I would highly recommend investing in Skillest.

Deal Details
Startup: Skillest
Security type: SAFE
Valuation cap: $15 million
Minimum investment: $100
Where to invest: Wefunder
Deadline: April 30, 2023

How to Invest

Skillest is raising capital on Wefunder. If you don’t already have an account, you can sign up for one here.

Once you’re logged in, visit the Skillest raise page. Be sure to review the deal page and offering documents thoroughly before making an investment. When you’re ready, click the red “invest” button. Enter in the amount you want to invest, starting as low as $100, and then move through the required steps. Make sure that your investment is confirmed, and then you’re good to go.


Startup investing is inherently risky, and startup investors should expect to hold their investments without liquidity for five to 10 years. Never invest more money than you can afford to lose.

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