Zap's Wrap December 15th

hi friends,

I have a lot to share this week…

Big news: I just made investments #23 and #24 into startups!!!

Investment #23: Finch Claims

Founded by Tom, Finch is an AI-native claims operating system.

Why I’m excited about this one:

I met Tom years ago when he moved from SF to Nashville while building Candid AI. The moment you meet him, you know he’s a builder. Not the pitch-deck kind, the “I’ll just start and figure it out” kind.

Before Finch, Tom was employee #7 at Carta, then went on to build two additional startups. He’s seen scale early and knows what it takes to go from zero to real.

When he was looking for his next role, I introduced him to Tristan at Edgevanta (investment #22 of mine!!). Tom helped build a new engineering team and then, unsurprisingly, the itch to build again returned.

So he did what he always does: launched.

Website up. Paid pilots sold. Full-time commitment. Finch was born!!!

Tom is rare in that he’s both a coder and a seller. He doesn’t wait for permission, he ships, sells, and keeps building.

Last year, Sydney from Focal VC moved to Nashville. A few months ago, she hosted a dinner in town with her team, Pascal and Daniel. Since then I’ve been trying to do a deal with them and I am super excited that only a few months later they are leading the preseed round into Finch (and their first Nashville founder)!

Tom now joins my portfolio as my 4th insurtech founder (Alongside District Cover, Elysian, & InRev). Somehow, I’ve learned way more about insurance than I ever planned to in my life and honestly, I’m not mad about it 😄 

More to come on #24 next week!!!

I have 1 bad photo with Tom from founder poker night lol. He used to be a pro player!!!

Some other updates:

Some tough, but vulnerable updates:

• I raised an SPV that ultimately fell apart and that was really hard. I believe deeply in giving more than I take. I try to bet on people who share that belief, who value trust and long-term relationships over short-term wins. When a Lighthouse founder made a promise to me and didn’t honor it, it was one of the more difficult moments I’ve had to navigate. The longer I do this, the more I’m learning that when something like this falls apart, it’s often a blessing in disguise. I have no interest in working with people who aren’t trustworthy, even when walking away is painful or inconvenient. What made this especially hard was feeling like I let others down, people who had chosen to invest in me. That weight sits differently. It forces me to reflect on what I can do better. For example, setting expectations up front and continuing to check in on them. I learned that not every deal is meant to happen. Sometimes my win is simply learning who I don’t want to build with, before it costs me more.

  I already spend a lot of time on founder diligence beyond the pitch: how someone treats people, how they follow through, how they show up when things get hard. Experiences like this are a reminder of why that part of the work matters so much.

• I was sick a lot last month and I feel like I didn’t end the year as strong as I’d like. I’m really focusing on taking care of myself so I can hit Q1 hard.

Some more optimistic, exciting updates:

• I helped 3 Lighthouse founders get lead term sheets in December. One is Finch, but I’m really excited to share about the other 2 startups when the time is right. Really big founder wins are on their way!

• District Cover closed their 6M Series A. This deal was a bit outside of my thesis being later stage, but I couldn’t miss an opportunity to invest into Patrick + team.

• A Nashville startup, Watt Data, is officially real! Jared, Mike, & John have formed a dream team. One to watch!

• I helped form another seller + coder team! Super pumped to see Eric and Christopher team up to build OneTap. They help multi-location restaurants manage, book, and pay for maintenance repairs.

• I took a trip to SF. It was my first time spending time there professionally. I learned the important lesson that it is the same as startups and investors everywhere else, there is just 100x more of it in Silicon Valley! I am planning a Lighthouse founder field trip back there in late February, especially for founders raising a round.

Startup jobs

• I have 2 startups hiring someone to be their marketing hire #1. If that fits your skillset, let me know!

• I have an ai e-commerce startup hiring for a Junior product manager.

• A manufacturing startup is hiring someone to lead sales in TN

• Unity is hiring for an Enterprise Sales Lead

• A construction tech startup is hiring for a junior customer success role.

Events

• Cofounder Connect, Tuesday, January 13th

  • I’ve helped form 10 cofounder teams so it felt like time to host an event focused on it (: Come and share what you’re building.

Personal

I went to Esalen, a retreat center in Big Sur. Our retreat was about Oscar Ichazo’s Enneagram teachings. It was wonderful!!

Come visit me at in-person office hours weekly on Thursdays. Since I’ve been sick, these have been pretty spotty, but I’m hoping to get back into the rhythm!!

to the moon,

zap⚡