Reflection, closing chapters and new beginnings

Hi friend,

For the last decade I’ve been taking time around Christmas to reflect, which should not come as a surprise to most of you. This year was a bit different for me, because with Rise we had a pretty rough year. Yesterday we announced that after months of trying to fundraise we weren’t able to secure follow up funding for the company. I’m pretty proud on our extensive blog with our full story, where we shared both the highs and lows. But with all this going on, it was weird to try and plan for this new year as I usually do, since I actually have zero clue to what I’m going to do next.

Still, my annual review was a super valuable exercise. In my day to day I’m focused on what each week could bring. I’m pragmatic, optimistic and forward looking. But taking time to let everything that happened sink in made me aware that while my weeks were fun, there was a longer arc, a theme even, of setbacks. Being present and forward looking helps, but in my case it shielded me from the insight that it was a real struggle.

Even more than different editions, the introspection helped figure out what was the right call for us and for myself. For me, that means sticking around in the same Google Doc for longer than feels comfortable. And, thanks to the helpful suggestion from Ernst-Jan Pfauth, I loaded my reflection doc into NotebookLM and chatted with my notes. AI functioned as my sparring partner to help uncover blind spots, I asked it to step into a therapist role and made it react as if it was my manager reviewing my notes. It does not replace a human. But it helped me with the first point: sticking around with my notes longer than I would otherwise, and make myself dig just a little deeper. You want to get those uncomfortable questions.

We worked on Rise for over four years. We aimed big: the tools we use at work are not great, to put it mildly. And we wanted to not just offer an addition to what existed, but a complete replacement. The chance of succeeding was low, as is the default for startups. We always knew that. And while we didn’t make it, we made it pretty far. We built a beautiful product and we worked on that with a wonderful team.

And so I continue to be deeply frustrated by the fact that our companies, governments and basically everything around us runs on products built by Microsoft and Google. Companies that earn most their money with other things, like Ads and renting out cloud services. I’m still dreaming of a company that has the success of other companies and teams at heart. Rise was not the answer, but I’ll be following closely to see who tries next.

As the first month of the year is almost behind us, I’d love to hear from you what you took away from your reflection this year. If there was any question that was particularly helpful, which one was it? I’d love to compile a fresh set and share that here in a few weeks. And if you haven’t found a moment to do a bit of digging for yourself, I’d love to encourage you to set aside some time to still do it. Don’t park it for 11 months.

Don’t be a stranger if you have ideas you want to pitch. My inbox is open.

Rick