The Rebooting
The Rebooting Show
Introducing The Rebooting Show

Introducing The Rebooting Show

The debut episode features FOS CEO Adam White

Subscribe on Apple Podcasts — more platforms coming soon.

After a year break from podcasting, I’ve finally started anew with The Rebooting Show, a weekly audio and video discussion that goes into the details of building sustainable media businesses with those building them. (The video is still in the works, and it will take a bit of time before the podcast feed is available on Apple and Spotify. Apologies.) The goal for the show is to focus on the mechanics and execution since I believe too much is generally made of “vision” in the media business. There aren’t a ton of secrets; those who succeed tend to simply excel at executing the details. 

My goal is to get beyond the PR spin that’s, unfortunately, a feature of most business podcasts. I always knew a podcast would likely suck if multiple PR people showed up with the guest. It was nearly guaranteed if the guest then took out a sheet of talking points. You’d be surprised how many big media executives feel uncomfortable simply answering questions about what, in theory, they’re responsible for doing.

My plan is to break the podcast into mini-seasons of five episodes focused on a theme. This first season is focused on modern B2B media businesses, a topic near to my own experience. B2B has long been treated as something of a backwater, at best a stepping stone to consumer titles. That’s always sold B2B short. There are many terrible, old school B2B publishers and events companies, but there are a new crop of modern players emerging who are still focused on going deep on the ins and outs of their business areas but do so with a higher focus on in-depth reporting, slick packaging and diverse business models. In many ways, I think consumer media can learn more from B2B than vice versa since B2B has always focused on direct connections (often through email), communities and diverse business models that aren’t reliant on advertising.

That’s why I wanted to talk to Adam White, the CEO of FOS, home to Front Office Sports and Sports Section. Adam started Front Office Sports while still a student at the University of Miami in 2014. His cobbled-together Wix site was meant as a foot into a sports marketing career but grew to the point where Adam made the plunge into starting a business out of it.

I’ve always liked Front Office Sports and how Adam and his team have thoughtfully built the company and continued to execute. In our conversation, we discuss the origins of Front Office Sports, the white space they saw in the market, their approach to differentiation, and the decision to build off their B2B base with newsletters aimed at a wider consumer audience.

Some highlights from our discussion:

The importance of talking to your audience

FOS began as an informational interview project Adam did one summer during college. Putting them online seemed a no-brainer. There wasn’t a product roadmap or a business plan, but Adam listened to what he was being told. Many of the interviews veered toward career advice, giving him insight into needs in the market. “What they told me all the time was these young professionals that work in sports don’t get accolades.” That led to what in retrospect was FOS’s breakout moment: The Rising 25 awards in 2017. “It’s been the most impactful thing we’ve done,” he said.

Not having money is a gift

Investment firm Steins backed FOS in 2018, but Front Office Sports took a bootstrapped path. That turned out to be a blessing in disguise in retrospect. “If we had the money before we did the informational interviews, we wouldn’t be having this conversation. We would have never figured it out. They told us everything we should do.” That gave FOS a leg up after it did have money to grow the business because it knew what it needed to do -- and didn’t waste money figuring it out by pursuing expensive and foolhardy paths. There’s no pivoting to video when you don’t have the money for the pivot. 

Sports is a giant category

There’s power at intersections. Increasingly, what were once thought of as defined categories are rubbing up against each other, even overlapping. Think of how athletes have become fashion icons, investors, crypto boosters and more. The business of sports is much more than tickets, concessions and TV deals. “Nobody said they’d make the business of sports sexy and cool,” Adam said. “We’re trying to build a publication that Mark Cuban reads and the general counsel of Netflix reads.”

Nothing is perfect, especially early on

The original Front Office Sports site was white text on a black background with a $40 logo. Needless to say, it wasn’t perfect. But it allowed them to learn and establish credibility with its core early adopters that paid off in the long run. “People will give you some grace as long as you're trying to be different, provide them with value and not ask for anything in return,” Adam said. 

Shoot your shot

The breakthrough moment on the business side of FOS was getting Anheuser-Busch as the headline sponsor of Rising 25. Adam and his cofounder Russ Wilde didn’t know what to charge, settled on the round number of $100,000. And to their surprise, A-B said yes. “That was massive at the time,” Adam said. 

I hope you enjoy the episode and welcome your feedback. I plan to send this second edition of The Rebooting newsletter every Monday with the background of the episode and highlights, as well as “5 things to check out.” I’m sensitive to not overwhelming people’s inboxes so I will continue to improve these to make sure they’re worth your time.

One other note on the sponsorship model I’m trying. I’ve written about how the editorial model needs to match the business model. I plan to apply that thinking here. Each season will (I hope) have an underwriting sponsor, usually someone whose business is focused on working with publishers to create sustainable business models. The fifth episode of the season will feature the sponsor in the same format as the other podcasts. I’ll approach these interviews the same way as I do any other. (These episodes will be labeled “Spotlight” in the podcast feed.) This approach was inspired by what Packy McCormick is doing at Not Boring with his sponsored Deep Dives.  Big thanks to Bernard Urban and Silverblade Partners for being my launch sponsor. I really like the approach Silverblade is taking to solve a real issue for publishers that I’ve experienced firsthand.

The media business moves incredibly fast, only the financial system underpinning it slogs along like molasses. That gap needs to be filled, leaving publishers with few good options, from revolving credit lines to drawing down equity capital. Many traditional lenders aren’t experienced in the long payment cycles in the media business. Enter Silverblade Partners, a strategic finance partner with the experience to work closely with senior management and banking partners to provide liquidity, better payment terms and higher credit limits. Learn more about how Silverblade Partners accelerates cash flow in the advertising media sector.

5 things to check out

Bored Ape Yacht Club is important to study if you’re trying to get your heads around the web3/crypto/NFT mania. This deep dive podcast by Colossus is a great primer. I’m going to write more soon, but my bet is the media company of the not-too-distant future will have a lot of characteristics of BAYC.

Workweek is a new player in the rebundling of media, focused on business newsletters. Workweek is looking for a middle ground between the freedom and independence of rolling solo with the reality that most “creators” like health insurance, paid vacation and support. Some won’t like giving up their rights to their content in exchange for security, but everyone has a different risk profile. Bonus: Workweek founder Adam Ryan has a media-focused newsletter, Perpetual

Naturally, the breathless hype of the newsletter boom is followed by the trough of disappointment. Building a business is hard, go figure. What’s more, there are many new skills to learn. After all, what did people think all those people who weren’t in the newsroom did all day? Going independent — much like everything in life — isn’t for everyone. That’s why I’m glad to see Workweek, Smooth Ops, The Atlantic and others building alternative models.

Speaking of Substack, it now has generated 1 million paid subscriptions. Sometimes I think Substack doesn’t get enough credit for providing what’s in essence a media business in a box. That’s not to say it’s easy — see above — but the Substack model is enabling many writers to chart their own path. One data point Substack is touting: The top 10 writers on the platform have generated $20 million in revenue.

In a world of “community-adjusted EBITDA,” we might as well give publishers “theoretical revenue” for their subscriptions businesses that absolutely don’t prop up big subscriber numbers with cut-rate introductory offers. Another reminder to take with a grain of salt the big showy top-line subscribers/subscriptions number.

Thanks for reading all the way to the bottom. Please drop me a note with any thoughts, objections or reasons why I should believe the Eagles can make the playoffs because it is very much a mathematical possibility. My email is

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The Rebooting
The Rebooting Show
The Rebooting Show gets into the weeds with those building and operating media businesses, giving an open view into how the smartest people in the media business are building sustainable media businesses.