Superpath’s Next Chapter

As of November 5, 2025, Superpath has a new CEO and owner. Yes, I sold Superpath and it’s now in the very capable hands of its new owner, Alex Hilleary.

I always hoped this would happen, but running a business is like running a marathon. If you’re thinking about the finish at mile 3, you’re in for a long day. You have to run the mile you’re in. I’ve been running those miles for 5.5 years and now it’s time to pass the baton.

Good vibes

Over the summer, I got an email from Alex Hilleary. He’d been an early Superpath member (way back in 2019) and we’d spoken a few times over the years.

Back in 2018, he’d co-founded a business called Gather, which he sold to ChartHop in 2022. At both Gather and ChartHop, he leaned on content and community as the pillars of his GTM strategy and it worked wonderfully.

This summer turned out to be a great time to reconnect. He was finishing up his work at ChartHop and was planning to create a new community using all the things he’d learned at Gather and ChartHop but with the freedom to be an independent business. What he described sounded a lot like what I’d been working at Superpath. This conversation filled me with energy and led to another and another. The vibes were excellent.

On our second or third call, Alex raised the possibility of acquiring Superpath rather than starting a new business. He loved what we’d built and had tons of ideas to improve the member experience. I was caught off guard. I’d recently completed a buyout of my business partner and had my own list of ideas for the future of the business. But after mulling it a bit, I decided that this was worth exploring.

Making a deal

Alex flew to Vail and we spent a day running through the business and talking about what a deal might look like. A week later, he made a formal offer, we each engaged a lawyer and started working on the deal, which we closed on November 5. Alex now owns the significant majority of Superpath, though I kept a minority share and will stay on as an advisor, contributor and, of course, a member. I’ll still be doing the podcast with Eric and Chloe, writing blog posts and hanging around Slack. I care deeply about this community and am so thrilled that I can still be part of it.

I didn’t expect for this to happen, but when he raised the idea, something clicked in my mind. Selling to an individual, and specifically, Alex was something I hadn’t really considered. He didn’t want to chop it up for parts or jack up prices to squeeze money out of it, he wants to sit in the driver’s seat and run the business himself. Every community must have this person to thrive.

There is some tension between the world of community and that of business. A community must create far more value than it actually captures. It can never put financial incentives ahead of member needs. And still, the community must generate revenue. I think of it as “win-win” revenue: it’s good for the customer and therefore good for the business.

This is an investment for Alex, but it’s not a private equity deal. There will be no enshittification. Alex is an experienced founder and understands what it means to work both on and in the business. Superpath is about to become an important part of his life’s work. If there’s one thing I’ve learned working with Alex for these last few months, it’s that he gives a shit. This is exactly what a community needs from its leader.

I’ll let Alex share his plans for the business, but we’ve talked through a number of ways to improve the membership. My goal has always been to offer the hands-down absolute best community for content marketers. Alex and I are fully aligned on that vision and he’s going to take it up a notch. Existing members can expect even more from their membership and you’ll soon see some new marketing around the upgrades that he’ll be rolling out.

A new chapter

I’ve been working on Superpath full-time since June of 2020. I’ve taken on a handful of small side projects during that time, but my heart, soul and time have always been in Superpath. It’s been such a wonderful journey and while I’ll still be around, I am entering a new phase of my life and career.

And if I’m being fully transparent, I was a bit burned out. I’ve mostly worked on this business alone, starting in the early days of COVID. It was surreal signing this deal sitting at the same desk I sat in when Walter and I formed the business 5.5 years ago. So much has happened since then.

Superpath has become a well-known brand in the content space. I grew the community to 24,000 free members and later transitioned it to a paid-only model. I stood up a marketplace that for a time processed more than $1 million/year in payments to freelancers. Superpath has helped people find jobs and mentors and friends. I acquired Help a B2B Writer. We’ve worked with incredible partners. Our podcast is 125 episodes and counting.

I also worked on every holiday and every vacation. I took three days of leave when my daughter was born. (Thankfully, I got smart and hired Eric to run the show for a month when my son was born a few years later.) I navigated a stressful trademark dispute. I spent more time working with lawyers and accountants than I care to remember.

Now that my wife and I have two young kids, my world and priorities are different. Running a business is rewarding and sometimes stressful. I never asked for it to be easy. I did it for the challenge and my wish was granted. And frankly, I’m extremely proud of what I’ve built. Superpath has made a small but meaningful dent in the universe. I plan to start another business one day, but the timing here is perfect for me. I’m ready to support and advise Alex as he takes the helm.

I am so immensely grateful to all of our members, partners and customers. And special shout outs to Eric Doty, Cierra Loflin, Kisha Velasquez, Chloe Thompson, Walter Chen, my endlessly patient and supportive wife and the many other wonderful people who have been on this journey with me.

Superpath is a platform for people to connect, and these connections have provided so much meaning and happiness in my life over the years. What a great ride it’s been so far.

Here’s to the future of Superpath and the future of content. I hope you’ll stick around for the next chapter because it’s going to be even better than the last.

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