Huddle Up's 2023 Changes: You Either Evolve Or You Disappear
Huddle Up's 2023 Changes: You Either Evolve Or You Disappear
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Friends,
I hope everyone had a nice holiday break. I spent the week hanging out with family and eating delicious food, and I definitely didn’t work out as much as I should have.
But I also spent a lot of time thinking about my business and this newsletter — where it started, how far we have come, and what it might look like ten years from now.
The majority of reflection revolved around gratitude. For those that don’t know, I have four brothers. We grew up playing every sport you could imagine — basketball, football, baseball, etc. — and I have loved sports for as long as I can remember (the 2006 Rose Bowl between Texas and USC is still the best game I have ever watched).
But while I always dreamed of working in sports, I can’t say I actually believed it would happen.
At first, I wanted to be a sports agent. Who doesn't love Jerry Maguire, right? Well, I spent time at Octagon, a sports agency in Washington, DC, and applied for 100+ positions across the industry, but it eventually became clear that path might be unattainable, or at least not look like how I initially imagined it.
So I followed my other passion for business and accepted a job on Wall Street. I obtained all the relevant licenses (Series 7, Series 63, etc.) and devoted thousands of hours to learning everything I could about fixed-income sales, trading, and research.
It was a good job. I was working at a top firm, making good money, and I wasn’t oblivious to the fact that many people would kill to be in that position. But even with success brewing on the surface, I wasn’t truly happy.
For example, in September 2019, I remember sitting in our office on Park Avenue. It was right after my birthday, and when I looked around the room, I saw people 2-3x my age doing similar work — for those that don’t know, the promotion path in finance is very structured, and you can pretty much map out your future 20+ years down the line.
This made me ask myself a very simple question: is this the type of job and career I want to do for the next 30+ years, and if so, will I be happy with that decision?
The answer was an immediate no. And to be honest, it still kind of shocks me how quickly I came to that decision — but it was vividly clear in the moment.
So I opened up a webpage and immediately started a Substack publication. I had no idea what it would be at the time, but I had seen other people succeed on the platform, and I thought exploring it as an option might be interesting.
But things don’t always go as planned. I wrote a few different drafts in the Substack app over the following week, but work got busy and I didn’t feel great about any single idea, so I put it on the back burner and never launched it.
Then the pandemic hit, and that changed everything. We were all instructed to work from home, and while that left many people in a state of fear of the unknown, it allowed me to remove myself from the situation and think clearly.
And that’s what ultimately led me to launch this newsletter.
It has evolved, of course. Many of you probably don’t even know this, but the first version was simply links to articles that I thought were interesting, both current and historical, with a brief summary detailing why people should care.
I would wake up at 5 AM each morning to write the newsletter before work. I didn’t have any writing experience, and I still cringe today when I read some of the early emails.
But it didn’t matter. I felt there was untapped demand for sports business content in the market, and I finally felt genuinely energized by the work I was creating.
So I kept going. I committed to writing the newsletter every day for six months, no matter what. I asked family and friends to sign up, read it, and provide feedback. I started a Twitter account to reach new audiences, and I expanded my comfort zone.
And to my surprise, things began to move. My girlfriend at the time (now wife) became the first subscriber right before the launch — she has supported this vision since day one, so thank you, Lexi! — and I ended the first day with 50 subscribers.
My writing then slowly started to get better. I changed the email structure to include more personal opinion and analysis. I started writing daily Twitter threads to help with marketing, and I networked like crazy to get people to share them.
And the craziest part is that it worked. I sent the first email in July 2020, and roughly two and a half years later, this email will go out to more than 75,000 people.
This hasn’t been easy, of course. I have spent thousands of hours working on this newsletter, often at the expense of time with family and friends. I published 100+ Twitter threads over six months (basically every day). I have made too many mistakes to count, and my body probably hates me for the frequent lack of sleep.
Still, this newsletter has undoubtedly been the most rewarding thing I’ve ever done. I get to talk about the money and business behind sports for a living. I have interviewed people like Lance Armstrong, Dana White, and Gary Vaynerchuk. I climbed Mount Kilimanjaro with Chris Long’s foundation and personally raised more than $20,000 for water-stressed areas in Eastern Africa.
But most importantly, I have built a global community of more than 600,000 people with similar interests from all walks of life. Now that’s amazing.
Still, that doesn’t mean I am always satisfied with the outcome. I made a promise to myself when I started this newsletter that I would individually review each email and only press send if it met a certain level of quality — I know your time is precious, and it was extremely important to me that I didn’t waste it.
But self-reflection is essential, and I can’t honestly say that I have lived up to that standard.
My business now includes this newsletter, social media, YouTube, podcasting, investing, and consulting, and while I have been able to hire some great people to help along the way, I often feel the quality of this email suffers as a result of me spreading myself too thin — and I *hate* that feeling.
So I have decided to implement a few changes this year. Going forward, instead of receiving this email each morning, Monday through Friday, you will receive three emails each week. This will include at least two sports business deep dives (similar to what you receive now), and the third will be a relevant long-form video or podcast.
My hope is that by reducing the number of newsletters sent each week, I will be able to focus on quality. This will make the deep dives a bit longer to read, but they will contain much better research, analysis, and opinion.
So please email me if you have any questions. I don’t have all the answers, and this might eventually change again, but I will always over-communicate when necessary, and my mission will never change: to be the world’s best source for sports business.
Thank you for your support, as always. I hope everyone has a great day, and we’ll talk on Wednesday.
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If you are not a subscriber of Huddle Up, join 75,000+ other professional athletes, business executives, and casual sports fans that receive it directly in their inbox each morning — it’s free.
Thank you Joe! I've suscribed to many newsletters over the year, and this is by far the best one head and shoulders above the rest. Genuinely enjoying reading each day. Good luck in 2023!
Great stuff! A great reminder for me too for self-reflection, and focussing on quality.