Transitioning from Coursedog

In 2023, I made the decision to step away from my role as the founding CEO at Coursedog. For anyone thinking about selling or contemplating their next mission - I hope this will be helpful. 

Deciding to Transition (2 weeks before transitioning)

After dropping out of college and grinding for 5 years: my cofounder Nick and I had begun to feel that Coursedog had reached a stable inflection point where we might be able to transition away from our roles running the company. The company was growing very quickly, with a great executive team, 100 people - and we had successfully facilitated a liquidity event - and something about the eeriness of how “stable” everything felt felt just a bit wrong. 

Personally - I felt that the principal reason for starting the business was some combination of ego/vanity, a remnant of my immature brain from starting the business by dropping out of college - and not something that I felt was “selfless”. I loved the team, the company - but it didn’t feel to me like I had really had the chance to take a deep breath and consider what could I really do to make the maximum positive impact in the world? And in some way I felt deeply unsafe in the stability - like, is this what I’ve been working for this whole time? 

And as such - I decided to transition from CEO at Coursedog, the company that I had devoted every waking hour for the last six years of my life toward. 

Having the Conversation about Leaving

The hardest part for me about deciding to leave was feeling like I was letting folks down. I had told folks after our secondary round that I had planned to stay on for the foreseeable future - and I felt like I had a massive ethical crisis in feeling like I was letting everyone down. That my hopes and dreams for the company were just another bullshit founder aphorism and not something real.

It’s hard to leave something you love - but when I did, I got a lot of hugs, tears - and a big weight had been lifted from my shoulders. 

Life-Post Transition (1-12 months from transitioning)

For a few weeks, it was exhilarating: I had thought that I might want to start a company around meditation (the thing I was most passionate about) and perhaps build a consumer product that could create a lot of joy for folks…

I suppose every second time exited founder thinks that finding product-market fit again is going to be some joy-ride. At some point when I was blindly sending embarrassing LinkedIn messages to folks at OpenAI and brain researchers I realized - holy shit - I’m totally fucking lost! Then when being lost hurts the ego too much - you say I’m going to start a venture incubator and start ten companies!

Exuberance of the sale quickly turned into flailing. The new normal of not having something to grind on was very hard. Like every founder: the first idea I had on meditation turned out to be a very bad one. And over the course of the next year - I basically woke up like a zombie, banged my head against the wall while thinking through BCI, meditation - anything that would take me out of what I had been previously working on and that I thought would be helpful in the world!!! I turned my back more or less on all the skills I had developed and imagined being like Elon Musk and going in a completely different direction.

It was probably the hardest year of my life. Obviously - it was incredible to not have to worry about money and having to work anymore - but in the same time I was in the trough of purposelessness - and my guiding light was to take all of my frustrations about my prior life as a #SaaS guy and run as far away from it as possible.

The “running” toward something else was a way of mentally justifying transitioning from the company. You have to always say it was for a reason - for some higher purpose - that it was good - and yet in the loneliness I felt a lot of sadness. I also started to get anxiety for the first time in my life that was really challenging.

What also made me feel sad is that the business I had left was truthfully: doing much better than I could have expected. The remaining team was as motivated as ever. And yet my heart felt elsewhere. I was flailing: like a magikarp (#pokemon)

Learning to Love Again (1 year post-transition)

At some point, I started to work on Starbridge: I had learned a ton about selling to gov + edu and hated a bunch of the sales tools we used at Coursedog. No one understood that the most relevant buying signals when selling to gov & edu were RFPs, competitor contract expirations, grants, meeting mentions - and they definitely weren’t helping us take action on any of these critical signals. We were spending hours writing RFPs & drafting up outbound messages”

My initial reaction was something like: fuck! Someone needs to start this business, maybe I can help them out. And then it was like a bad shrooms trip while looking in the mirror - I was like. Is that me????? Is it me that should start this business? Why did I fucking sell my first business dealing with all this government & education bullshit and then want to do it again?

However - as I started to explore the idea I just felt like I was skating, dangerous (as I knew too much) and just having fun again. And I really was very delicate and careful about thinking about the forever mission - I didn’t want to end up with the same love of business but not love of mission as Coursedog. While at first I had gotten upset at myself for being so excited about something so similar to my last company - I realized quickly that if we got this right and reduced the cost to innovate in government & education by 1000x, it would be meaningful to so many people, not as some bullshit silicon valley aphorism, but I felt it in my heart. And kinda forgot that growing and having customers that rely on you inherently just makes you feel purpose. The best thing I did during this time was be super gentle with myself: letting myself fall in love with the mission - and to just be really positive and think bigger than I could have ever imagined.

Loving Again (1.5 years post-transition)

Last month, I was sitting in Hawaii next to one of my closest friends Vinay who wrote this article about his life & challenges after selling his business. 

While he was writing his article, I was responding to customer tickets for the new business like a madman, now sitting in Hawaii on a “vacation”, sipping water from a meaty coconut. 

I felt for Vinay deeply and the purposelessness that I felt after selling  - but also it felt like a hazy memory - I was back to building, shipping - doing the hard things - now drinking a coconut. 

I had just closed a $10m seed round. And I was fucking pissed when I all of a sudden spilled my coconut water on my keyboard and ended up stranded without a computer in the middle of fucking nowhere Hawaii when I should have been in the office in NYC!!!

But god damn - the rush of that customer ticket and my broken keyboard - I felt alive again.