This week, I handed Holloway's CEO reins over to my co-founder, Josh Levy. As we built Holloway over the last four years, I got the chance to explore the depths of my love for research, writing, and sharing stories. My belief in the purpose and mission of this company hasn’t wavered, but over the last six months I found myself wishing I could be a full-time independent creator. And at the end of July Josh and I came up with a way for me to do that.
As a company, we're in a powerful position, and I continue to be enthusiastic about Holloway's future. This summer, we published two new books, signed eight additional authors, created our first print editions, and built publishing infrastructure that streamlines our print and digital production processes. We’re on track to build an alternative to the Amazon Kindle monolith by empowering authors to publish and market their books on the web.
Josh is the right person to lead Holloway. Over the last four years, he’s driven the development of the Holloway Reader and sculpted each Holloway Guide. He’s been instrumental in closing deals with authors and he’s pushed the frontier of what it means to be a digital publisher.
As for me, I'll remain on the board and continue to be involved with several projects in a significant way at Holloway.
How We Got Here
A combination of factors led me to decide it was time to hand the reins over to Josh. The first was an intense period of taking stock on life, work, the universe, and everything, thanks to the many events of 2020. The second was a slow burn of watching friends have the courage to begin new career chapters as independent creators. And the third involved getting an idea that kept drawing me in despite doing my best to ignore it.
In 2019, we published my first book, and I wrote a weekly newsletter. I loved it. For the first time in my life, I felt like the writer I had hoped I'd become since I was a teenager. I remember walking up 5th Avenue with our Senior Editor, Rachel Jepsen, when she, responding to something I said, told me “You're such a writer.” That meant the world to me.
As COVID hit, I felt overwhelmed. I dealt with a bout of depression for the first time since 2017. I tried to journal my way out of the crisis, and one thing I realized was that without a book or a newsletter to write, I felt like I'd lost a big part of myself. In April and May, I watched my friend Nathan Baschez pursue a new career as an independent writer with his newsletter, Divinations. I envied Nathan.
During the same time, I listened to friends struggle with personal and professional relationships, and I realized how the fact that people chose to come to me in these moments was something I should pay attention to. I enjoy listening and doing my best to help. I started four companies with different people each time--relationships between co-founders are something I think about a lot, and something I’ve had a lot of experience getting wrong and getting right and learning why.
In a rare bright moment in 2020, I got on my feet and began to gain new perspective after my girlfriend, Kate, and I decided to get an apartment in San Francisco after being on opposite sides of the country for a year. I turned to Kate one night and told her that I loved Holloway and our team, but I was feeling drawn to explore something--something I needed my experience at Holloway to discover. What if I spent the next few years researching, writing, and helping co-founders learn how to form and nurture healthy relationships?
I started to write another book.
After a while, I felt like I was cheating on Holloway, sneaking off at night to outline and draft. I didn’t want to wait until 2025 to pursue the project, and after everything that had happened this year, and someone I trusted to turn to, I realized I didn’t have to.
So I told Josh what I was thinking, and as he and I were planning for the next phase of Holloway in the summer, we decided we’d restructure the company with him at the helm, enabling me to pursue this new project. It was anything but easy, but I'm proud that he and I were able to work this out.
As for the scope of my new venture, it's a work in progress, but one of the principles I've laid out is to work in public. My number one objective is to get to the heart of what separates co-founders with healthy relationships (with each other, at home, and with their team) from co-founders with toxic ones. I hope it’ll be considered a sequel to Noam Wasserman's The Founder's Dilemmas. I plan on publishing a portion of my writing for free and making another portion paid, and I'm creating a podcast to share interviews when folks feel comfortable going on the record.
A big part of why I’m doing this is because of what I’ve learned about publishing from working on Holloway. I think the breakout authors of the next decade will be those who write in public on Twitter, Medium, Substack, and any other platforms that give writers the tools to build a supportive audience as they learn and share. I hope to publish my book on co-founder relationships on Holloway one day, and I encourage others to think about Holloway as a place to roll your newsletters and blogs up into beautiful digital and print books.
In addition to creating, I'm committing myself to learning and working hands-on to help other founders. My first step was to enroll in The Hudson Institute's coach certification program. If you’ve considered hiring a coach, I begin my certification in January, but I’d love to start getting my sea legs this fall.
If this excites you, please sign up for my mailing list in the green box below. If you have ideas you’d like to share, or you’re interested in speaking with me about coaching, please shoot me an email at firstname.lastname@example.org.
Working on Holloway has been one of the greatest joys in my life. I'd like to thank Josh Levy, Rachel Jepsen, Dmitriy Kharchenko, Hope Hackett, Courtney Nash, and Vahe Hovhannisyan, and to our investors, my friends, and my family.
I’m grateful for the team’s support in this decision, and I'm extra grateful to Josh Levy for stepping up and taking on the responsibility of leading the company.
Looking forward to what’s next,
How You Can Help
→ If you know any co-founders (or groups of co-founders) who would be willing to speak with me (on the record is a plus, but not required), I'd love an introduction.
→ If you know anyone with experience working with a coach, I'd love to speak with them to learn how I can offer the most value.
→ If you’re interested in learning more about Holloway, as an author, investor, etc. You can still reach out to me, or you’re welcome to speak directly with Josh, too, at email@example.com.