Five Years of LongJump

In 2015, I was raising the first round for WiseApple and most of our initial funding came from a handful of Chicago founders and Northwestern alumni who had built companies here and took a bet on me and my co-founder. Over time I kept meeting founders who were every bit as good but didn’t have those relationships.

Fast forward a few years and many of the people who had written those first angel checks had moved on to running institutional Seed/Series A funds, creating a vacuum in true early stage funding in Chicago outside of a few angel groups. So in 2021, a group of founder-operators co-founded LongJump: Brian Luerssen, Garry Cooper, Ablorde Ashigbi, Kristen Sonday and Tim Grace. I joined as a venture partner in 2022 and took over as managing partner in 2023. LongJump was essentially a bet on the city’s founders. We didn’t think Chicago had a talent problem; we thought it had an access problem. Great founders weren’t getting funded because they didn’t have the right networks. We deliberately built a diverse partnership with different networks, and pooled capital from some of the city’s top tech founders and operators to start writing those early checks ourselves.

Our first check went out in fall 2021. Five years later, we’re Chicago’s most active institutional investor at the pre-seed stage. We’ve invested in 48 companies, and we’ve been the very first money in more than 80% of the time. Together, our companies have raised over $85M and counting. With our second fund, we’ve invested $870K over the last 15 months, and those companies have already raised roughly $22 for every $1 we’ve put in.

More important than the fundraising numbers, the companies are working. Evergreen is scaling nationally as one of the country’s fastest-growing new food brands and made the Inc. 5000. Seven of this year’s 1871 Momentum Awards finalists were LongJump portfolio companies, and Eventnoire took home the Social Impact Award. Rise Reforming just finished YC, and we were one of only two investors before the program. Nara Health, which we backed in a pre-seed round, has since raised nearly $14M, including from Khosla Ventures and Long Journey Ventures.

I think being first really matters because of what comes with our check. We’ve spent five years building what we believe is the best network in Chicago for a founder at the very beginning: founders who have done it before, operators, customers, investors, and LPs who have built companies here themselves. The Raise, our program that teaches founders how to run a fundraising process, came out of that work. Our 2026 cohort of 15 companies closed nearly $4.4M within six months of the program. Going in, none of the founders felt very confident about fundraising. Coming out, 77% did. More and more of my calls start with a founder we’ve backed telling me about another founder we should meet. Being useful to the ecosystem is how we see the best companies first.

We also back a wider range of companies than people expect. Houndsy is profitable, also made the Inc. 5000, and will grow more than 250% this year. LongJump is the only institutional fund that’s invested in the company. A lot of the founders we meet now look more like Houndsy than like the typical venture pitch. They’re using AI to do with a small team what used to take a big one, and they don’t plan to raise round after round.

That makes the first check matter more. If companies can get much further on much less capital, the question stops being who can raise the biggest Series A and becomes who makes sure a great founder gets the first investment, before everyone else knows their name. That was the gap LongJump was built to fill in 2021. I think it matters even more now.

Heading into our next five years, our focus is the same: be the first check for founders building great businesses. We’ll keep working alongside the other organizations doing this work instead of recreating what they do well. And we’ll keep bringing successful founders back in as customers, mentors, angels and LPs, and as the person who takes a call from a founder two years behind them.