One of my favorite authors and thinkers is C.S. Lewis. In his great book The Four Loves, he writes that friendship is born "at the moment when one man says to another, 'What! You too? I thought I was the only one.'" That perfectly captures how I felt when I first met Landon.

We were both in our early 20’s. We both had ambitious visions for what Chicago's tech community could become post-Covid, and we both believed Chicago had the talent to compete with the coasts. We also shared the blessing, and sometimes the burden, of careers that accelerated faster than our age. Early on, I often found it difficult to relate to people in my peer group. Then I met Landon.

For the first time in adulthood, I had a friend my age who understood the unique dynamics of an unconventional career path. Your wins don't sound like bragging, and your setbacks don't sound like ingratitude. We quickly became inseparable. If I had a dollar for every time someone came up to me at an event and asked, "Where's Landon?" I'd be rich enough to buy the Bulls and finally turn things around.

We do share our iPhone locations, so maybe next time I'll just start giving people his exact coordinates.

Today, Landon leads Drive Capital's Chicago office, overseeing the firm's investments across the region. Drive is $2.5B fund and was an early investor in companies such as Duolingo, Hallow, and Udacity. Beyond investing, Landon also writes Landon'sLoop, one of Chicago's most-read newsletters covering business and civic news. More recently, he launched OneTwoLoop, an initiative focused on revitalizing Chicago's engineering job market.

Landon is the ultimate side-quester. I believe in focusing on one or two things and doing them exceptionally well. Landon somehow manages to do ten things at once and excel at all of them. It's a trait that started early. During high school, he even had a brief career as a rapper. I won't share the link here (trust me, it’s for your own good), but I've been forced to listen to those songs over the years, often against my will.

I'm excited to have LC join the newsletter this week. Hope you have fun reading.

I've always loved bringing people together. Growing up, that meant making videos with friends, serving as the social chair of my fraternity, and becoming the VP of DePaul my senior year. Today, it means building communities for founders and builders in Chicago.

For the past five years, I've been obsessed with creating spaces where ambitious people can find co-founders, customers, and opportunities. Too many people assume those connections only happen in places like SF or New York. I've spent my career trying to prove otherwise.

The most meaningful part isn't the events themselves. It's seeing what happens afterward. Companies get started, careers change, investments happen, and friendships form.

Creating environments where people discover what's possible is what gives my life meaning.

Honestly none of them.

I've never viewed accomplishments as finish lines. I've always been more interested in momentum than arrival.

When I was running my podcast, there were people who told me, "Reach back out in a year." Most people would move on. I wrote their names down and followed up anyway. Eventually, many of those conversations happened.

That's how I've approached most goals in life. I celebrate wins when they happen, but I don't spend much time sitting in them. Every milestone tends to expand my view of what's possible next.

I'm not really chasing satisfaction. I'm chasing growth.

Ambition has opened doors I never could've imagined. It's introduced me to incredible people, put me in rooms I never expected to be in, and given me opportunities to build communities, invest in founders, and contribute to Chicago's startup ecosystem.

At the same time, ambition can make life move very fast.

One lesson I've had to learn is that relationships are built through consistency, not intensity. It's easy to focus on the next project, event, or goal. Slowing down doesn't come naturally to me.

Lately, I've been more intentional about creating space for the people and things that matter most, whether that's family, my relationship, faith, or simply being present.

Ambition creates opportunities. Presence helps you appreciate them.

Honestly, it has nothing to do with work.

I recently got a dog, and she's brought a level of presence into my life that I didn't realize I was missing. No matter how busy the day gets, she needs attention, care, and time. She doesn't care about meetings, newsletters, investments, or events.

I'm also proud that I talk to my family every day. As life gets busier, it's easy to convince yourself you'll call tomorrow. I've tried to make sure tomorrow doesn't become next week.

Neither of those things will ever appear on a resume, but they're probably more important than anything that does.

I became obsessed with making Chicago more founder-centric.

When I looked around the ecosystem, I saw plenty of rooms filled with investors and service providers. Those groups play an important role, but I kept asking myself the same question: where are the founders?

Builders should be at the center of any startup ecosystem. Founders meeting founders. Engineers meeting engineers. People creating things together.

That belief led me to spend a lot of time organizing hackathons, founder dinners, co-working days, and builder communities. Some people questioned the obsession. I never did.

I've seen firsthand what happens when the right people end up in the same room. 

Doubling down on builders was one of the best decisions I've made.

That I'm never going to be the person who focuses on just one thing.

For a long time, I felt pressure to pick a lane. The advice is everywhere: find one thing and ignore everything else.

I've realized that's just not how I'm wired.

I'm passionate about investing, writing, community building, technology, music, civic engagement, and a handful of other things. On the surface they can seem disconnected, but they're all driven by the same themes: bringing people together, creating opportunities, and helping people discover what's possible.

Some people are specialists. I'm a connector.

The moment I stopped fighting that and started embracing it, everything made a lot more sense.