Brooks Dyroff discusses Walk-On Holdings

We recently sat down with Brooks Dyroff, a 29-year-old entrepreneur who left Blackstone one year ago to start his own media holding company. While this story might not pertain exclusively to real estate, we were simply curious as to why someone would leave a Private Equity firm to start a newsletter. Dyroff sat down with us to discuss his new company, Walk-On Holdings, which owns and operates three digital media brands: Tag The Flag, The Street Sheet, and Pregame Skate. More on all of these below.

Brooks, can you give us a little bit of background about yourself?

BD: Absolutely. I grew up in Boulder, Colorado, which, to this day, is my favorite city in the world. For my last two years of high school, I went to Phillips Academy in Andover and then moved 40 minutes down the road for 4 years at Boston College. In 2013, I graduated from BC and moved to New York where my first job was at J.P. Morgan. After about two years, I moved a few blocks north on Park Ave., and worked for three years at Blackstone. In the spring of 2018, I left Blackstone and started my own media holding company, called Walk-On Holdings.

I gather you’re a hockey player.

BD: Yes, I was and I still play. I was fortunate enough to play for Boston College where we had a great run during my time there. Currently, when I’m in New York I play with the St. Nicks hockey team at Chelsea Piers. They’re just an awesome group of guys who couldn’t have been more welcoming when I moved to the city. For any hockey fans out there, Hobey Baker actually played for the St. Nicks. The history of the club is amazing. 

Got it. Tell us about your time at J.P. Morgan.

BD: J.P. Morgan was a perfect fit for me professionally right out of school. My time at the bank gave me great exposure to pretty much everything going on in the world of finance. I met some great people and learned about everything from analyzing stocks to assessing more complex alternative assets. To that end, when I was at J.P. Morgan I specifically remember Jon Gray, (the current COO of Blackstone) coming into pitch the first BREP Asia fund. His energy and Blackstone’s presence in the building was palpable and I remember thinking I want to do what they do. 

So is that when you made the switch to Blackstone?

BD: Well, not immediately, but that is when I knew I wanted to work for them. 

Tell me about the switch and ultimately what you ended up doing for them.

BD: Switching was slow with numerous interviews, but ultimately I landed a position in their real estate division in the spring of 2015. I ended up working on the debt side of the business with a focus on the private funds. During my three years at the firm, I was based in the U.S. but also had the chance to work overseas as well. 

When you say overseas, where else did you work?

BD: I worked in Blackstone’s London office from September 2017 to March 2018, which was incredible. I met people in the UK office and was closer to some of the work being done in Europe which was a great learning experience. 

Why did you decide to leave?

BD: Leaving Blackstone was an incredibly hard decision, but I always knew I wanted to start my own company. My dad is my hero and he started his own small business so for as long as I can remember that’s what I wanted to do. When I was 17 I started a non-profit organization called CEO4Teens with my best friend from Boulder. I’m proud to say that since its inception we’ve raised six-figures of scholarship money for hundreds of teenagers in Bali, Indonesia and also created a high school GED program which has sponsored kids in the Boston area. This was my first experience with owning and operating my own “business” and I’ve had the itch to do that for a living ever since. 

Can you give us some background on what you did end up starting?

BD: For sure, last summer I launched a general holding company called Walk-On Holdings. Right now, Walk-On Holdings is the parent company for three brands: Tag The Flag, The Street Sheet, and Pregame Skate.

Can you tell us a little bit about each brand? 

BD: Absolutely, in a nutshell, this is how I describe them:

Tag The Flag is a multi-media brand dedicated to uniting our country and making Americans smarter. We post pictures of the American Flag on our Instagram and Facebook pages to bring our country together and we are home to America’s only nonpartisan morning briefing, which we trademarked as “America’s Newsletter“. Personally, I’m sick of the partisan divide in our country right now, which I think comes to light most aggressively in the news. Most people don’t have all day to sift through the insane amount of content which is slanted towards one side or the other. The goal of “America’s Newsletter” from Tag The Flag is to give readers a nonpartisan briefing that they can read in less than 3-4 minutes to start their day. It comes out at 6 AM EST every Monday through Friday.

The Street Sheet is a newsletter that gets published once a week on Sundays. The five-minute briefing gives subscribers everything they need to know about the world of business and finance including a weekly market review, upcoming week preview, and deep dives on specific headlines in the VC, IPO, PE, and M&A spaces. 

Pregame Skate is our hockey-specific brand. We host live conference calls with NHL players coaches and scouts every month. These conference calls mimic live events that hockey fans and families can attend from anywhere.  

Where does the name Walk-On Holdings come from?

BD: My grandpa walked-on to Ohio State’s football team and won the Rose Bowl, and my mom walked-on to University Of Colorado’s Ski team and won a national championship. I was a recruited walk-on to Boston College’s hockey team where we had a great four years. I thought it was fitting and I like the idea of having to continually prove yourself for a spot, an opportunity, or just a chance at success.  

At the one-year mark, how are all of these brands doing?

BD: They’re doing well. Across all channels, we have over 225,000 subscribers. It’s a good start but there’s still more room to grow.