If you’re new here, let me introduce myself. And if you’re not new here, why haven’t you sent this to your friends who need to know more about youth sports yet?

I’m Doug Freeman. I grew up in Lakeland, Florida. Played junior college ball, then D2, then independent professional baseball. Coached at the junior college level. Started Prep Baseball Florida, then started Groupbook to service hotels and tech partners in group travel. Sold both.

So I’ve had quite a ride. In my Free Time, I share my insights on youth sports, what you should actually expect, plus business, AI, acquisitions, some culture, and really whatever I think is important or relevant. I’ll have some initiatives I want to push, but mostly I want to talk about what’s important today, in an ever-changing landscape, from my perspective.

In partnership with

The ice cream shop that makes money when it's cold

28 Wishes sells ice cream in Los Angeles. Below 70°F, sales fall about 20%. The weather is out of their hands. Rent isn't.

So the owners started putting about $20 a day into Kalshi weather markets, taking the cold side. The days that keep customers away now pay something back.

This is hedging. Big companies have done it for decades, buying protection against bad weather, fuel spikes and rising rates. It used to take a broker, a trading desk, and an order size no corner shop could meet.

Kalshi opens it up. Contracts on weather, fuel prices, inflation, tariffs and regulation, starting at a few dollars. Take a position on the outcome that would hurt you. If it hits, the payout softens it. If it doesn't, the contract expires and the good month was the point.

LETTER (from Doug’s Oct 28 dictation, light edit only)

Private equity is the villain of youth sports right now. At least, that is the story going around.

There is a lot of bad press, and some of it is earned. New data just came out showing participation dropping for lower income families while the top end keeps growing. That is certainly not good. Nobody who loves this world should be happy about that.

But I want to slow down and talk about what private equity actually is, because most of the argument skips that part.

Private equity is pooled money from investors. A firm raises a fund, buys businesses, tries to make them bigger and better run, and sells them a few years later for more than it paid. The goal is a return. That is it. Not charity. Not evil. A business model.

I talk to a lot of these folks. They certainly see a financial opportunity. They are not blind to the optics either. They know how this looks to a parent writing a check.

So what is there to be done? If I had every answer I would have implemented them yesterday. Here is what I do believe.

More investment into coaches, facilities, clubs, and events helps. Professionalizing assets helps. Making it easier to access, and making it possible for brands and companies to get a real return, helps. A bigger ecosystem means more opportunities, for more kids, in more places.

We can argue the alternatives. Fund local volunteer run events better. Give national governing bodies more control. Let government intervention suddenly become a good thing. Congress is already in this conversation, with a bill that would ban private equity from youth sports outright and a tax credit proposal on the other side.

Here is where I land. Athletics is about competition. So is business. Bring on good, well run businesses and capitalism. Let customers speak with their wallets and their decisions. The operators who serve families well will grow. The ones who squeeze families will get found out, by parents, by competitors, and now by Congress too.

Capital is not the villain. Bad operators are.

The take: what private equity actually buys.

Private equity does not buy a sport. It buys businesses inside the sport. Tournaments, leagues, facilities, software platforms. The pitch to investors is simple. Youth sports is a $40 billion market, fragmented, mostly run on spreadsheets and volunteers, and families already pay. Roll up the pieces, professionalize them, and the whole thing runs better and makes more money.

That pitch is why private equity’s share of youth sports deals jumped from 27% to 37% in a year. Wall Street is not betting on bats and balls. It is betting on the businesses around them.

Here is the question that decides whether that is good or bad for your family. Does the investment go into coaches, facilities, and better events? Or does it go into fees, forced hotel stays, and streaming charges? Both versions exist right now. The first version grows the sport. The second version is why parents are suing and Congress is holding hearings.

The test is simple. Watch where the money lands. If a tournament gets better fields, better refs, and a schedule that respects your weekend, that is investment working. If the only thing that changes is the price and the hotel you are forced to book, that is extraction wearing an investment costume.

Quick hits.

Participation among kids ages 6 to 12 in households earning $25,000 or less fell 7% in 2025, while every higher income bracket grew. The gap between the richest and poorest kids is now 24.8 points, up from 14.5 in 2022. a new national participation report

Parents filed a class action suit against a youth hockey operator, claiming families were forced into designated hotels, charged fees they were never told about, and that the operator collected kickbacks from hotel partners. a class action suit filed this month

A bill in Congress would ban private equity from youth sports entirely, and a House hearing in June took up the commercialization of the sport. a bill in Congress and a June hearing

A January 2026 survey of 922 youth sports parents found 81% pay attention to a brand that sponsors their child’s program, versus 54% for a pro team sponsor, and 80% would pick the youth sponsor’s product over a similar one. Only 3% felt negatively about brands being involved at all. a January 2026 survey of 922 youth sports parents

The average family now spends $1,016 a year on one child’s primary sport, up 46% in five years, and families total more than $40 billion a year. the cost numbers behind the crisis

One model gaining ground shifts the bill from parents to brands, with sponsorship revenue directed back toward lower costs for families. a model that shifts the bill to brands

Something fun.

I am in Dallas this week, and I will say this for the city. The food scene is incredible. Fajitas one day, sushi the next, and all of it walkable. Dallas is a great place to visit and an even better place to eat. I have eaten my way through this trip and I am not done yet.

Doug

P.S. Know a parent arguing about this one right now? Forward this to them. That is how Free Time grows.

Own a sports company, or any company, really? I’ve exited two of my own, and I’m actively helping owners raise money privately or sell. If that’s a conversation you want to have, book a call.

Parent in the middle of the youth sports ride who wants one-on-one guidance? Book here.