MY WINS AND MY LOSSES

My wins are my brands.

"My wins are my brands. When i believed my money was better off spent on ME."

- Dan Castle

I spent years putting money behind other people's companies and ideas. Some worked. More than one did not. The clearest lesson in my record is not that I learned how to pick better outside bets. It is that my best use of money, time and judgment has been building brands I control.

This page is the honest accounting.

The losses

Money in someone else's company is still someone else's company.

The loss side should name what I believed, what happened, what I got wrong and what the experience changed. No spin, no blaming the market and no pretending a loss became a win because it taught me something.

Ample Hills Creamery

I was an investor in Ample Hills Creamery. I believed the brand could become something much bigger than it was. The company filed for bankruptcy in 2020, and the investment went with it.

What I got wrong: I believed a brand people loved would find its way to a business that worked. My money was in the company. The decisions were not mine.

What changed afterward: I stopped confusing a beloved product with a sound business. If I cannot see the economics and influence the decisions, I would rather build the brand myself.

Convoy Trucking

I was an investor in Convoy, the digital freight company. At its peak it was one of the most heavily funded startups in logistics. It shut down in 2023 anyway.

What I got wrong: I confused a big valuation and famous investors with a durable business. The money I had at risk came with no control over the outcome.

What changed afterward: I stopped treating other people's confidence as evidence. The only bet where I control the result is the one I build myself.

The outside win

Sweetgreen

Sweetgreen was the outside bet that won, and it became the bridge to my own brand.

"i sold sweetgreen stock at its height and invested all of it in castleflexx"

- Dan Castle

I sold the stock at its height. Then I took all of that money and put it into CastleFlexx.

Sweetgreen matters here because the return did more than prove I could make a good outside investment. It gave me the capital to stop being a passenger in someone else's company and fund a product and brand I controlled.

The turn

The outside win funded the bet on me.

I did not take the Sweetgreen return and look for another company's stock. I invested all of it in CastleFlexx.

That was the turn: from betting on which company might win to making myself responsible for the win.

Instead of putting money behind someone else's decisions, I put it behind a product I created, a brand I owned and outcomes I could change.

That is when the record changed.

My brands

CastleFlexx

CastleFlexx began with a problem I had lived with for more than a decade. I created the product, secured the intellectual property and built the business from the ground up.

What worked

- A patented product platform with US and international protection

- Adoption by professional athletes, team staff, chiropractors and physical therapists

- Approval for use by the Atlanta Braves during home and away games, including the 2021 World Series season

- More than 50,000 customers reported by the company

- A 2022 GOOD DESIGN Award

What it proved: When I put my money behind my own judgment, I could do more than advise the business. I could build it.

Jooni

Jooni is the next version of that decision: take a real problem, create the product and build the brand around something I own.

Jooni is still in progress. It does not belong in the victory column because I say it will work. It belongs on this page because it shows where I choose to place the bet now: on my own ability to create, operate and carry the result.

Proof beyond ownership

Ronald Acuña Jr.

I sourced and helped close a seven-figure endorsement partnership for Ronald Acuña Jr. The platform partner, exact value and deal terms remain confidential.

This was not my brand or my investment. It was proof that the same judgment works in dealmaking: find the value, structure the opportunity and stay with the negotiation until it closes.

Martha Stewart

At Martha Stewart, I helped lead the business through a renewed period of growth and negotiated major multi-year partnerships.

It taught me how a founder's name, standards and point of view can become a commercial system without losing what made the brand matter.

The assessment

My wins are my brands.

The outside investments made one thing clear. I do my best work when I am responsible for the whole result: the idea, the money, the product, the brand and the decisions.

That does not mean every brand I build will win. It means I know where my conviction has earned the strongest return.

Bring me the decision that matters.

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