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Off To The Races with Max Siegelman of Siegelman Stable
Episode 2: Great Things With Adrian Williams
In a world where we could have just about everything we want at a moment’s notice, we have to pick and choose where we allocate our energy and always remember that while good things are fleeting,
Great Things Take Time
If you’ve ever wanted to take a risk, build a business, and work for yourself, today’s newsletter is for you. The second episode of Great Things features Max Siegelman, the founder of Siegelman Stable, and is a true testament to the methodical work it takes to pursue a passion and grow your business.
If you were forwarded this email, you can subscribe and join the Great Things Take Time Community to get content from me (and Frankie) every Wednesday.

I am upset about this horse talk. Dogs > horses. I shall pout from over here.
Today's Thoughts
Off To The Races
Home alone, with his favorite artist, Future, playing in the background, was when the idea hatched in Max Siegelman’s mind to create the foundation of what is now Siegelman Stable. Now, it’s been more than half a decade since Max started his company, Siegelman Stable, and even longer since I’ve known him.
Funny enough, we met more than seven years ago in a workout class. See? I’ve always been able to talk while doing burpees 😉 But in all seriousness, to get true insight into someone's character, take them to a workout class and see how they approach a challenge laid out before them. It’s how I started to learn more about Max, and while I believed in his vision, I’ll even admit that I never expected the brand to have grown into what it is today.
My mistake.

Let me be clear, learning about someone’s character through fitness has nothing to do with how fast or strong someone is; it has everything to do with how they approach what’s presented to them. Do they attack what’s in front of them with the best they can give? Or do they look for shortcuts and cheat themselves? What is their attitude like? When I met Max, he approached each class with determination and a goal in mind, but also a level of kindness that drew me to wanting to be his friend. Most of our friendship was rooted in the fitness world until he started showing up with these hats he’d designed.
When we got together outside of the gym, I started to hear about his new project: creating memorabilia for his family centering around his mom’s work in sports media, and his dad’s racing stable, Siegelman Racing Stable, founded in 1982. His dad’s work had a long legacy of training horses for harness racing included titles and trophies, but also encompassed charity work through several charities that brought geriatric and well-mannered horses to interact with military veterans, children with autism, pediatric cancer patients, and inner-city kids.

From a text from Max, somewhere at some time
Originally, he was just creating hats for his family and friends. Think- matching shirts for a trip to Disney, Christmas PJs, or family reunion shirts - just a touch more elevated. Soon, outside interest pushed him to slowly start to expand and begin putting the product up for sale. Some of his early days were spent sending out inquiries and packing up hats in his studio apartment to ship out to various power players across the sports world, music industry, and other key public figures in hopes that someone would like the merch enough to wear it. As things started to take off, so high was his output of shipping boxes that Max gifted custom hats to the local UPS driver who handled the shipments.

Things paid off, and eventually, Future, the man whose music was the soundtrack when Max’s original inspiration hit, was photographed wearing one of Max’s early hats.
As Siegelman Stable’s reach grew, and his collection made it into the hands of people like Steph Curry, Kendall Jenner, Aaron Judge, Dwayne Wade, The Chainsmokers, and both Biebers, he still presented as the same Max that I knew, but it was clear that there was more depth to him than I had realized.

The tenacity that he had brought to his workouts was evident in the growth Siegelman Stable was seeing. I hadn’t even considered who he was outside of the fitness studio, but it was a great reminder to see people outside of their surface presentation.
Max’s journey is an inspiring one, and there was no doubt he was a perfect subject for the Great Things With series. In the episode below, you can hear in Max’s own words about how he views his journey and the advice he has for those looking to start their own business, but as an outsider looking in, there are a few things that stand out to me from his story:
Being Your Own Boss Is Hard
First, it’s that being your own boss is hard. He has a team, but at the end of the day, it comes down to him to make the decision on anything. Whether it be shipping, logistics, the store, or distribution, he’s accountable for every decision. This means that there is really no such thing as a vacation; you have to be prepared to take a call if there is something time-sensitive. There is no practice round, no trial period; every decision he makes impacts the future of his business. He can’t just step back and let someone above him take over; he is the someone higher.
In a way, being his own boss has been helpful for Max because I see how much he appreciates time off now. That man’s mind works at a million miles an hour; he always has a new idea and is such a forward thinker, but now getting to turn it off is valuable to him. He’s not a straight practitioner of hustle culture.
Going At It Alone Only Takes You Halfway
If you talk to Max, he’s clear that much of the brand’s success has come from his fiancée, Karoline Spenning. When she stepped in to help, she brought a new perspective, and her influence pushed the brand from streetwear and hats to what I would describe in my uninitiated view as being pop culture meets luxury. (What can I say, Car-man is not always good about describing non-car things).

Max and Karoline (far right) at a Siegelman Stable x Muhammad Ali event
Together, they have formed a force where no detail is left to be forgotten. Everything is deliberately done in a certain way that creates an experience, however you interact with the brand. If you’ve visited their SoHo popup store, you’ll see this on full display with the care taken in how the curtains hang. The two of them complement each other perfectly and made the business even stronger, proof that Great success doesn’t always come from going at it alone.

Behind the scenes several years ago
Finding people who can inject their expertise into something makes for a more unique product. Of course, there is the saying “too many cooks in the kitchen,” but when you find strategic partners like Max has in Karoline, there is no option but for things to flourish. There is a fine balance between holding the reins tight and letting things develop organically, and when you have another mind expanding your viewpoint, you’re going to see things materialize in ways you could only dream of.
You’re Going to Need Courage and Dedication
The beginnings of Siegelman Stable were created in the late nights, early mornings, lunch breaks, and the in-between moments; it wasn’t the main focus for a while. He was essentially working three jobs, consulting work, his role at Outfront Media, and Siegelman Stable, which meant he had to be dedicated with small steps to make his passion work; it wasn’t always an easy and clear singular action he needed take. It wasn’t until things took off and there weren’t enough hours in the day for everything that Max eventually had to concede and drop a few things off his plate to take on Siegelman Stable full-time. Then, it was off to the races (all the pun intended), and Siegelman Stable has started to hit its stride.

Most people have a self-prescribed path and can’t imagine stepping off it, but no matter what your life looks like, it can be scary to take a leap from the certain to the unknown. Of course, Max was relatively young when it was time to make the switch to being full-time with his business, but I still see it as requiring immense courage to make the switch. Whether the change comes with new schedules, new roles, or financial stability, going after a Great Thing takes courage. Never undersell that or forget it. It doesn’t make you weak; it means you care.
Your Passion Will Grow It
Max didn’t start with a plan to start a business and then search for a direction; he started with a direction and poured passion into it that caused it to grow. With a strong foundation, it made it easier to expand because there wasn’t any ambiguity around what the brand meant to him; the brand identity was clear, and he wasn’t just making things for the sake of making them. I also believe it’s the reason the brand continues to go strong; there is meaningful substance behind it, honoring his family’s legacy and giving back to those in need of equine therapy, as a portion of the brand’s proceeds go to charitable work. This base also ties into the final point…
Don’t Lose Yourself
Sometimes, success can change a person for the worse, but if anything, the success of his company changed him for the better. Max is still the same Max he’s always been. He’s grown in many ways, but it’s in an expansion of himself, not a new persona. Because he is doing something rooted in purpose, he doesn’t need to put on airs to fit in new spaces; he presents who and what he is without fear (well, from my angle at least). In the Great Things Series so far, both Chef Mario and Max have this in common: they’ve put their energy into a passion that has caused it to stand out from others. If they were to lose themselves, they would lose the aspect that makes their product so unique. It can be tough when you hear from others that you should be doing something a different way, but you’ll never regret staying true to yourself.
Your Turn
From the outside, building one’s Great Things and seeing success can look like a lightning strike, but more often than not, it’s filled with long nights and behind-the-scenes work doing what needs to be done. As Max says in the video below, if you’re looking to make a switch or build something on your own, his best advice is to find the time for the things you’re passionate about. But the best time to start? That’s an easy one to answer… now. Next thing you know, you’re off to the races.
Tune in every few weeks for more episodes of Great Things on IG, Tiktok and full episodes on YouTube.
Know of a Great Thing that we should spotlight?
Moments with Maurice
If you only pause to reflect on your life for one moment today, do it now.
Max’s story of intentional creation is one that many others have shared when building their Great Things. Perhaps you’re already on that journey now? Take some time to reflect on what things look like for you.
Prompt: Great Things don’t wait for perfect timing. What are you building, and how can you make space for it while staying true to who you are?
Your turn! Journal your answer, or if you find yourself sharing the progress of your Great Things on social, tag me at @greatthingswith_adrian so I can join in on cheering you along!
![]() | What’s Got Me Smilin’ |
Because no matter what, there is always something to smile about.
Damn, I Put My Foot In This
Each week I’ve been committing to making at least one meal that’s a tad bit more complicated than normal, and boy did this one hit. This week, after getting all my stress and tension out by cutting up parsley so that it resembled dust, I made a warming coconut chicken thigh dish.
Try it if you like…
1.5 Can of coconut milk
1 cup of Chicken stock
2 tablespoons of tomato paste
1/2 onion
3 cloves on garlic
Parsley
1 tablespoon of flour
Sear chicken thighs and remove.
Add remaining ingredients to pan, cook for 5 minutes and then add chicken thighs back
Sure, if you don’t squeeze your glutes then no one else will, but if you don’t sear your (chicken) thighs…
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The Downshift
It’s the final countdown with the G80 M3 and I hit up J&B Body Works to see the progress. I know it feels like every week is the final step, but I don’t want to rush this process. To me, this is something special and I want to leave the crash and any other negative feelings behind in 2025.

Have a certain topic you want me to dive into in these newsletters? Send it here or reply back to this email.
![]() | See You Next Time |
Remember:

-Adrian




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