2025 Reflections
Work was a bit of a roller coaster this year. I had some ups. I had some downs. What I’m most happy about is ending the year on a high. And having faith I can have that snowball into 2026. Ending on a high note is a big deal.
The first part of the year was hard. I was an IC and I was hustling but not getting the results I wanted. I had some deals I loved, but I wasn’t moving the needle. I felt stuck. It was frustrating.
Jonny and Read both went on their 3 month sabbatical. The coordination was terrible. It left me with a lot on my shoulders. The IC stuff came extremely easy because I got all of Jonny’s leads. But more importantly, I leaned into leadership. And I was successful. We grew and exceeded expectations. I was proud.
Then Jonny and Read came back, and I shifted back to IC. There was the incorrect presumption that Jonny would assume the role of "master orchestrator". In practice, he crushes deals and is our best sales person, spokesman, and external face of Wefunder. He’s a different kind of leader. Me moving back to IC, and Jonny also being an IC, created a leadership vacuum, which caused me a lot of frustration.
Leadership
I was on a soapbox, crying out for Wefunder to invest in leadership. When I was exhausted from my lonely soapbox, I took matters into my own hands. I took a swing at filling the leadership vacuum I was so frustrated by. I assumed informal control over the majority of the team, and put all my eggs into the “leadership” bucket. It turned out to be emotional fuel.
My dad shared a graph about the “most leveraged professional skills”. AI was high on the list. It’s becoming a more clear “known” that AI competence is going to be more relevant and important in this next chapter of our world — and especially true if your career is in tech. It’s the next “Internet”. At some point that needs to be on deck for me.
I’m making a deliberate decision to not go down the AI path right now.
Because in that same graph my dad sent me, the next “grouping” of most sought after professional skills oriented around leadership. Leadership and social influence. Systems thinking. Talent Management. Empathy and active listening. Resilience, flexibility, and agility.
These fit into the "I like this" and "I'm good at this" and "there's more upside". Leadership is the never ending skillset that I want to develop and pursue. I’m going all in on leadership, and it feels good to have direction and scope. Leadership could be the path for my next 20 years.
There's a risk in being too forward with the "stake in the ground". My approach is one with stealth and quiet intention. I've been through too many cycles to get too excited. This will evolve. There will be more down cycles. I will, with absolute certainty, say "fuck this" at some point. But time and experience has also taught me that this is part of the process. It's directional. It ebbs and flows.
Are we climbing the right mountain? Sometimes it's hard to tell from the weeds. This is a quick eagles eye spot check.
Cheerleading
One of my favorite learnings in 2025 was the value of being a good cheerleader. A skill my grandma taught me.
There are many things in my work that are easy to say and extremely hard to do. Raising capital is a bag of worms. Founders are more frequently stressed, emotionally drained, and struggling to keep it together. There’s a lot of nuance in reading that in another person, and showing up as a good cheerleader. Being a good listener. Not having a menu of advice, but rather a menu of questions. Being a sounding board for founders to process the challenges around their business. And most importantly, finding the right way to say “you got this”, “you’re on the right track”, “keep going!”. Far more nuanced in practice than in theory.
I suppose that’s the value of 6.5 years. At face value you can see my situation as stagnant. I’ve been doing the same job for 6.5 years. On paper, it’s a “grow or die” dilemma. Leave Wefunder, take bigger swings at learning. Start my next company.
But the job is people. And people are complex. It’s a never ending puzzle, and this year specifically, I think I did learn and grow and expand on the topic of people. Maybe not on paper. But deep down I feel there’s a difference in how I think about the people I talk to every day. An elevated pulse on humanity and emotions. How to show up as a positive influence and valued cheerleader.
I’m doubling down on Wefunder. This shit is fun.