Reflecting on 2024: The Good, The Hard, and What’s Ahead

Hi Friends,

As 2024 winds down, I’ve been thinking about everything this year brought. Moments that stretched me. Lessons I didn’t expect. Memories I’ll hold on to for years. It’s been a mix of highs and lows. The kind of year that reminds me of how much growth comes from both.

As 2025 approaches (yep, hard for me to believe), I wanted to take a moment to reflect on this past year. Here’s a look at what stood out, what challenged me, and a few predictions for 2025. Thanks for being part of this journey with me!

🥳 Highlights from 2024:

• Building Next Wave NYC: One of the most meaningful projects this year was launching Flybridge’s Next Wave NYC. I’ve always believed in the power of community, and seeing this come to life alongside founders and investors in the city has been incredibly rewarding.

• Family Time: My daughter Charlie turned one this year, a milestone that brought more laughter, chaos, and perspective than I could have imagined. Traveling to the Philippines to meet Cat’s family was a trip I’ll never forget (though I could do without another 24-hour flight anytime soon). My son, Holden, has continued to grow into an incredible person and has been a super helpful big brother along the way. We’ve had the chance to bond even more and to become “friends” even at this young age just as my Father and I are now.

• Portfolio Wins: A big part of this year was watching some of the companies I’ve invested in hit new levels of growth. One raised its Series A shortly after our seed round. A lot can happen quickly when the founders are focused and driven.

• Two Years Sober: This year marked two years without alcohol. This choice has brought clarity and calm into so many parts of my life. Staying present for my family and my work has been the most rewarding part of this journey.

• Joining The Pitch: Getting invited to The Pitch podcast as a guest this year was a real highlight (and getting invited back again was the cherry on top)! I love hearing founders share their stories and ideas, and it’s always energizing to be part of those conversations. We even got to back a few of the startups.

• Recognition: Being named one of Business Insider’s Rising VCs was a meaningful moment. It’s always nice to be recognized, and being included alongside so many talented peers was a reminder of why I love this work. Although it’s hilarious after nearly a decade in venture LOL. Whatevs, I’ll take it.

😓 Lowlights from 2024:

• Friends Shut Down: Supporting founders is one of the most fulfilling parts of my work, but this year, I saw a few companies I’d worked with for years have to shut down. Not every journey ends the way we hope.

• Work-Life Boundaries: My son Holden gave me a hard truth this year. He noticed that I was spending too much time on my phone. He now gives me “time-outs” to put me in my place. While I’ve gotten better, I still have room to improve.

• Liquidity in Venture: The first half of 2024 was tough. Exits were moving slower than usual. Things picked up later in the year with deals like Nasuni and Zest AI, but it was a long wait to get there.

🚀 Looking Ahead to 2025:

• Small Teams Can Do Big Things: This year has shown how much smaller teams can accomplish with the right tools and focus. Big ideas don’t always need big budgets. Startups are achieving more with less (today that company is north of $30M in ARR).

• AI is Changing Everything: Two years after ChatGPT launched, AI is making a real impact across industries. From education to finance to healthcare, it’s helping people solve practical problems.

• Better Market Conditions: IPOs and M&A deals are increasing, creating more opportunities for founders to build and for funds to perform. In 2025, more companies may consider early liquidity options like dividends or secondary sales.

• NYC’s Growing Momentum: New York continues to attract talent and innovation, and I’m looking forward to seeing its startup community grow next year. Flybridge and I are fully invested in this city.

• Time for What Matters: On a personal level, I’d like to spend more time with my family in 2025 and being more intentional about how I use my time. If 2024 was a year of lessons, 2025 will be about putting those lessons into practice.

📌 Jesse’s Picks:

5 things that were on my mind this year:

• Time Arbitrage: As an early-stage founder, your single greatest asset is your time. Focus is the only way to develop a product or business that maximizes your time wisely.

• Napkin Math: Years ago, I invested in Squire, a platform for finding barbers. It sounded pretty basic, but they nailed it regarding straightforward calculations.

• Missed Shots: I had a shot at investing in 30 Madison. I could have owned 20% of what’s now worth over $1 Billion. Every VC has more than one "the one that got away" story.

• Stop Solving For VCs: As a founder, your job isn’t to optimize for what VCs want. Massive rounds. Hypergrowth. Or billion-dollar exits. It’s to build a valuable company.

• Supernetworks: High-touch support for founders doesn’t scale by hiring more people. It scales by rethinking how networks work. Helping founders help each other.

📸 This Year in Photos

Thank you for being part of this journey. Here’s to 2025.

Jesse