Reflections
It appears, I’ve been hiking through the vast red rock valleys of Southern Utah. Beautiful forest, huge rocks, big inclines, and epic views. The world is my oyster. My body hurts, but I’m having a lot of fun.
Then I stumble into the Narrows in Zion. The “womb” of Mother Earth. A slot canyon with orders of magnitude energy. The vast beauty condensed into a hallway of towering rock walls hundreds of feet high. Completely consumed, I slowly make my way through the river, and with each turn I become more amazed than the last. I keep going. This is new. This whole thing is epic.
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2025 was a weird year.
On one hand, there’s joy and excitement for the new life ahead.
On the other, the process of “bringing a human into this universe” was more emotionally taxing than I anticipated.
I’m still working through that process, and my guess is that it will be a long process. There are a lot of dimensions to it.
I wish I weren’t so heady. But I am. It’s my greatest strength. And my greatest weakness.
Life Just Got Narrow
Chatting with friends? Now we’re chatting about pregnancy. And the “new life” and challenges that await us. Every time. It’s more annoying than helpful. And I’m good on your unsolicited advice.
With Julia, it’s the main topic of discussion, a daily pulse on the shifts of each day as the baby grows from an olive to a canteloupe. I feel helpless to help.
And, most prominently, within my own head, those thoughts seem to be a constant trickle of rain.
Some rain is good. I appreciate the time to prepare.
Rain all day every day is bad. Flash flood alert.
It’s just been too long. There’s only so many times you can have someone tell you, or think to yourself, “say goodbye to sleep”. I’m exhausted of the topic of being exhausted. I get it. I’m ready to start.
Presence and Long Term Perspective
Presence is a noble and aspirational goal. Enjoy where you’re at. Don’t look ahead. Focus on now. I value this as a leading principle.
Long term thinking also relevant. A few years is nothing in the greater story of one’s life. Before you know it, the baby is a kid, and then a teenager, and then an adult. And you are on your own again with the rest of your life to experience on your terms. Enjoy each stage. Consider the bigger picture.
Finding the right balance between these two is tricky in practice. The presence of 2025 feels long and drawn out. The long term thinking seems so distant. The past nine months has felt like years. How this all comes together in the next year feels lightyears away.
Longest days, shortest years. Yeah. Not sure that’s “energizing” in concept or practice.
These pieces are part of the process. A lot of the time, it’s hard to think of this process as fun. But I’m looking forward to the rewards. It’s the cake on the carrot, as they say.
Rewards
The challenges in losing (and grieving) my own individuality. The anxiety in keeping this baby alive. The 24/7 attention to survival. The lack of sleep. “Baby Proofing My Life”. The chaos ahead. Challenges stacked.
I’m sure there will be moments, when I look back to where I’m at now, and say in a frustrated and sarcastic tone — “what rush, bro?”.
But where I’m at now lacks reward. It’s like waiting in a very long line. With each hour in line, or month in pregnancy, I get slightly more irritable and frustrated. No reward, just slightly less people in front of you in line.
When Jack comes, all of those challenges will come true. But I will also have a daily dose of reward. A smile. A laugh. A nap. A centimeter of progress in one of a million things that make up a human. Daily reminders that what I’m doing is extremely cool.
So I welcome the challenge — as I so look forward to the daily reward from the challenge.
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FUN!!!!!
In an effort for this blog post to not be completely consumed with the singular omnipresent thing that’s driving me mad. I also had a sick year.
The most fun activity of this day. Going through all my photos!
— Skiing! My favorite thing. When you find that moment when everything clicks. The weather, the snow, the run, gear, the music, the spirit. I’ve had many of those moments, and I cherish them. The Tahoe back country expansion and new gear, the week of epic snow in Mammoth. 20+ days, 6 new mountains (Snowbird, Winter Park, Jackson Hole, and Vermont). Each one unique, providing those peaks of physical, emotional, spiritual.
— Hiking. A 69 mile trek on the PCT. A new “level” unlocked. New friends. A deep desire to keep doubling down. A love for the pain and preparation and process. A very fun and challenging day scaling a 14ker in Colorado. A huge 17 mile day in Idyllwild. A cold and wet hike in Vermont. Seeing the epic forests of Olympic, and adding to my long list of sick mountain hikes, with an epic birthday hike in the North Cascades.
— Trips. The baby moon at Disneyworld and the epic beach days in Florida. Disc golf in Colorado. Kayaking a cross a huge lake in the middle of Texas while drunk with Jonny. Exploring New Orleans with friends old and new. An epic 1,000 mile tour of Washington State. Late nights and over indulgence with friends — and relaxing “refuel” weeks with Julia in Idyllwild. Good hangs with Nate and Jonny and Suz in New York. The Kansas City blowout and the train. The Kiva reunion and late nights at Seacliff with homies.
— Music. Dancing in the rain to Artbat, my favorite minute of the entire year. Going super super hard at Justice. The joy of the Turnstile show. Zakk Sabbath, Thrice, Rickshaw, Mayhem mosh pits. Brand New, Paul McCartney, Charley Crockett, Meatbodies, Oliver Hazard, Air, and The Devil Makes Three. Lots of really good shows.
— More Music. Music league and records. Hundreds of new CDs and vinyl. The joy of the weekend pop into Folk Arts or Vinyl Junkies. The love of the hunt. The joy of picking something with intention and having it create the energy in the room. The fun in Music League. And then more Music League. And then more! The explosion of new music from that. And the catalyst for friendship and banter. The best.
— Moments. Padres games with friends and Padres games alone. Dodger World Series. Game 7. Fishing with Sonny and Josh. The night at Turf Club with all the homies. Nights in San Clemente with Josh and Bryon. The SDFC playoff run.
— Disc Golf. Maintaining a 5 year run of 3:30 Tuesday disc golf. An extreme loyalty, shared amongst 3 friends and a dog, a weekly treat for all of us. The life skill of intention and commitment and priorities and friendship and fun — all developed in the best way. We all subscribe and we all benefit. AND I FINALLY GOT MY FUCKING ACE!!!!!!!!!
— Blu is still rocking. 16 years strong. I feel more and more lucky with each year we have her. I didn’t know if she’d make it to Jack, but that’s looking likely, which makes me so happy. Her endurance on the full disc golf every week amazes me. She’s tuned into some annoying things, but to me, they are special. The begging is out of control, but I love it. The 7:00 PM ball time routine. She’s yelping all the time. The nesting of her bed. The joy of the new beds we got her. The sweetness of the cuddle at the end of the day. The mornings when you really wanna go on a walk. I cherish each year with gratitude and my heart expands. I owe a lot to her.
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That’s a long list. 2025 didn’t feel over the top, but writing it out makes it feel that 2025 was way over the top. That’s good. That’s what we’re doing here. Working hard. Playing hard. Having fun. Dozens of memories picked up with each month. You hold onto those forever. This is the currency of a life well lived.
Ambition is so frequently positioned around your career. I appreciate that I’ve been able to really stretch and apply ambition to the fun parts of life. And many times, combining work with fun. Ambition for living could be a tagline.
I also believe there might be a “moderation” question. Will having a kid decrease the volume? If so, will I value these experiences more? How will this evolve with each year? Will it be as rich a list? Is rich in quantity or quality or both? To what extent do I have agency? Whatever the answer (and no need for your fucking opinions), I hope and trust the universe will deliver.
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Work
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.