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An Interview with Brooks Dyroff

Brooks Dyroff, CEO & Founder of Walk-On Holdings (Credit: LinkedIn)

We recently sat down with Brooks Dyroff, a 29-year-old entrepreneur who left Blackstone just about a 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 one of the best Real Estate Private Equity firms in the world to start, wait for it… a newsletter? If you’re as curious as we were, then we think you’ll find this profile extremely fascinating and come to believe that Dyroff is certainly someone to watch along with his new company, Walk-On Holdings, which currently owns and operates three digital media brands: Tag The Flag, The Street Sheet, and Pregame Skate. More on all of these below. Some of the questions and answers have been edited for brevity and clarity.

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.

And you were a hockey player, is that right? Do you still play?

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. So speaking of J.P. Morgan tell us about your time there.

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. 

All of this sounds great, which begs the question: why did you 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.  

This all sounds interesting, but why would you leave Blackstone to write newsletters?

BD: I think newsletters are one of the most overlooked media products, despite seeming somewhat antiquated. If done correctly, I think they can generate a surprising amount of revenue, with relatively low overhead and expenses. Secondly, I think building an email list can help you launch other verticles whether that’s an app, a magazine, podcast, events, etc. 

So maybe it’s a stretch, but what made you do this 180-degree turn and switch from Real Estate to Media. Is there any correlation? 

BD: I would argue there is, or at least I approach the way I’m building Walk-On Holdings somewhat similarly to how you might build a real estate fund with a handful of physical assets. For me, each newsletter is a property. It might not be a physical property but that doesn’t mean you can’t touch and develop them. For example, Tag The Flag and “America’s Newsletter” is simply an intellectual property that is protected by the USPTO. Secondly, each property has developers, property managers, and brokers. My developers develop code instead of molding brick-and-mortar; my property managers make sure the property is being taken care of – this could be a writer or a UX/UI professional for example; my brokers help sell the space for advertising. Last but not least, the most important rule of real estate: location, location, location, applies to what I’m doing as well. For me, the location just happens to be in your inbox almost like a billboard that people drive by on their way to work. 

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. 

You can subscribe to all of Dyroff’s newsletters below and we wish Brooks the best of luck moving forward.

Tag The Flag Sign Up
The Street Sheet Sign Up
Pregame Skate Sign Up

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