Mike Schatzman is a managing partner and emerging fund manager based in Chicago. With a background as a successful 3x exited entrepreneur, Mike transitioned into venture capital and fund management. He focuses on early-stage investing, particularly in applied AI verticals, leveraging his extensive network of founders, advisors, and investor groups to source, evaluate, and add value to deals. Mike’s hands-on experience as an operator informs his strategic approach to investing and supporting founders.

ORIGIN STORY
How did you get started and what has your journey been like so far?

Mike: I’ve spent time in corporate America, was an entrepreneur with successful exits, and have invested across all major asset classes. I’ve also advised many first-time entrepreneurs. My journey has touched the entire ecosystem - entrepreneurship, corporate, investing, and advisory. I backed into being a VC and emerging manager, and I think what sets us apart is that my partners and I have been in their shoes and can add real, strategic value to founders. Early-stage investing is hard, fun, and stressful, but I love what I do.

ROLE SPECIFIC:

What has the switch been like for you going from entrepreneur to fund manager?

Mike: It’s just so different. When you’re an entrepreneur, you’re a mile deep and an inch wide—you’re building a company, hands-on, in the thick of it. As an emerging manager, you’re a couple inches deep and a mile wide; you’re focused on a lot of different things. Both are hard, just different types of stress and challenges. Now, I can step back and see the bigger picture, instead of being right in the middle of everything.

How has your investment thesis evolved, especially with the focus on AI?

Mike: When you’re an emerging fund manager with a 10-year horizon, you have to be flexible. A lot changes in 4-5 years, and nowadays it can change weekly with AI. In Fund I, we focused on applied AI vertical and horizontal businesses, which we see a bright future for the next decade. But you always leave room to pivot subtly within your strategy.

Since you invest across multiple verticals, how do you handle due diligence in different industries?

Mike: We have an incredible network of advisors and exited founders and are in a lot of specialized groups. Our team starts the diligence, then we bring in domain experts as needed. If we didn’t have this network, we’d need a much larger team. That’s a major differentiator for us—our network lets us handle a wide range of industries effectively, and not many emerging managers have that kind of reach.

How did you build your team?

Mike: All through personal relationships over the course of 5 or 6 years of networking and investing; building trusted relationships doesn’t happen overnight. Some people have come and gone, but now we have a strong, aligned team. Some are waiting for us to finish raising capital before their value kicks in.

DEAL DESK:

Do you have a favorite or creative deal that stands out?

Mike: One of the most interesting deals was right before we launched our fund. I was called by some lawyers in Florida about an entrepreneur with deep insurance and tech experience. I didn’t know much about insurance, but I dug in, loved the founder and his business plan, negotiated the valuation down by half, and put the deal together. It became a fund investment and has performed outstandingly since day 1.

When you’re looking at deals, do you focus more on metrics or the founder?

Mike: At the end of the day, the founder reigns king. You want to see they’ve really thought through their business and projections, even if things pivot. It’s also important to make sure the other boxes are checked, so we look for founder-market fit, early traction, product built, and the potential for a big addressable market as well.

MISTAKES:

What are the biggest mistakes you’ve seen GPs, LPs, or founders make?

Mike: For GPs, it’s FOMO—investing just because big names are in or following the leaders without doing your own homework. The “big boys” have massive amounts of capital and need to place bets everywhere, but that doesn’t mean you should follow blindly. Strong cap tables are very important, but you need your own validation and memos showing your thinking. Rushing decisions or skipping in-person meetings are also common mistakes. For significant investments, you have to meet the founders in person.

OUTSIDE THE FUND:

What non-work activity helps you be better at your job?

Mike: Golf. I play a lot of golf when I can, so that just keeps my mind fresh, installs patience, and then, just really helps me, because when you play golf, your mind is on the goal. The game really forces you to take your mind away from whatever might be bothering you, so that is something that really helps me out a lot, and I enjoy doing it.

Any book or podcast recommendations?

Mike: Everyone likes the All-In Podcast. One of my favorite books is Setting the Table by Danny Meyer—it’s about service and hospitality but applies to all business: understanding your audience, asking the right questions, connecting the dots.

FOR THE BEGINNER:

For those wanting to break into fund management, what’s the best place to start?

Mike: The best way is to jump in and get your feet wet. Don’t wait for the perfect opportunity—it rarely comes right away. Start somewhere, get the experience, and doors will open.

Best advice you’ve received or would give your younger self?

Mike: Don’t be afraid to ask for help. It’s not a weakness—it’s a strength to know where you need support. I wish I’d done it more when I was younger.

FOR THE EXPERT:

Mike’s fund is currently raising for Fund Two, targeting $40 million with a first close at $15 million (about half already soft-circled).

What sets Mike’s group apart: