Over the years, a #GiveFirst network will reward its members time and time again. Troy Henikoff looks back at 2009, when he first encountered Techstars and was so inspired he started his own accelerator—with some help from the Techstars Network. A decade later, that accelerator is now Techstars Chicago, and Troy is Managing Director of MATH Ventures. You never know where #GiveFirst will take you—but you do know you’ll never have to go it alone.

How does a startup ecosystem grow? #GiveFirst is one essential element.

Troy Henikoff, Managing Director of MATH Ventures and Co-founder of Excelerate Labs, which became Techstars Chicago, remembers the early days of Chicago’s startup ecosystem, and how #GiveFirst helped it grow.

One of the difficult things about describing the impact of #GiveFirst is that, over time, there are so many effects. Troy spends time in this episode telling stories about how giving and mentoring have changed his life and the lives of lots of founders, in Chicago, Boulder, and beyond.

It’s a tangled web of awesome, where a decade after Troy’s first interaction with Techstars, there are so many winners it’s hard to keep track. And the wins just keep piling up.

Companies, resources, and people mentioned in this podcast:


The God Particle: If the Universe is the Answer, What is the Question? By Leon Lederman with Dick Teresi

How the Internet Happened: From Netscape to the iPhone, by Brian McCullough

I2A Ventures

Illinois Mathematics and Science Academy

Leon Lederman

Lurie Children’s Hospital of Chicago

MATH Venture Partners

Next Big Sound – acquired by Pandora

Next Big Ventures

Sam Yagan

Sandbox Industries

Edited highlights from the conversation:

The origins of Techstars Chicago, and the power of a Give First network:

David: We’re really excited to have Troy on Give First today. Troy is one of the partners and founders of MATH Venture Partners, and we’ve known Troy for a long time. Troy is one of the reasons that Techstars is in Chicago, he was the managing director at Techstars Chicago and before that at Excelerate Labs, which was a fantastic accelerator. So we have a lot of history with Troy. Troy, welcome to the show. We’re really glad to have you today.

A lot of people might have heard the story of how we first met and how Excelerate Labs and Techstars came together. But a lot of people haven’t. I think it’s a really interesting story, so I wanted to give you some space to talk about that.

Troy: Yeah, it was fascinating. In 2008 I had been teaching entrepreneurship at Northwestern for awhile and I had some students in my class who were just different: Alex, David, and Samir. They were better than any other students I had had up to that point. When they did their final project, they presented their business plan, and all of the judges came up to me after and asked if they were doing this company for real, or if it was just for class. If it was for real, they wanted to talk to them. They were doing this thing around music and the internet and we rounded up about $25,000 in seed capital, which we had never done for undergrad students before.

They struggled for a while, and they really tried to get this thing off the ground. In 2009,  Alex, the CEO, had graduated and David and Samir were still seniors in college, and they got accepted into this thing in Boulder called Techstars that I had never heard of before. When they told me about it, it sounded like they were going to get some capital and mentorship and spend the summer in Boulder, which sounded awesome. So they piled into David’s VW and drove down to Boulder to be part of the program.

David: You know, before they did that, Troy, I had to fly out to Chicago, and I met them in the airport. I remember it vividly.

Troy:  I’ve heard that a little bit about this story. Yeah. To persuade them.

David: I used to fly to the airport of whatever town companies were in and take a meeting in the airport and then fly back. I remember meeting those guys, all just sitting in those crappy airport seats.  

Troy: They came down to Techstars and—as it’s been told to me—they got there and on about day two of the program, they said this dog isn’t going to hunt, and they thought their business was doomed. David, you were there, so you can tell me a little more about what happened then.

David: They walked in—it was day two of the accelerator program—they said that they just didn’t believe in their business anymore. They were sort of saying, “We’re not sure we believed in it when you funded us.”

Our reaction was: okay, cool. Let’s figure out what we should do, because the investments is in you, not in this particular idea. We weren’t too sure about it either. So we just started brainstorming, and I remember a big whiteboard session that day.

Troy: Fast forward to the end of the program, 88 days later. I was down in Boulder for Demo Day and Alex did an amazing job with his pitch. I think he was asking for $350,000 in seed capital to launch this new thing around music on the internet that he called Next Big Sound. There was a line of investors waiting to invest. He actually ended up raising over $1 million in that round, turning people away. It was one of my first angel investments.

It was that day that I realized a couple of things. One was how awesome the program was for Alex, David, and Samir. It took them with this nascent idea that wasn’t going to work. It helped them figure out how to pivot, how to find a real business model, how to raise money—raise over a million dollars—and how to go into business. That was phenomenal.

The second thing was that there were a handful of us from Chicago who happened to be there. Techstars had just expanded to Boston. You had 10 companies in Boulder, nine in Boston. Of those 19 companies, five came from Chicago. That was awesome, except they all left and didn’t come back. Next Big Sound set up camp in Boulder because that’s where their lead investors were. They never made it back to Chicago.

I remember the date, August 6, 2009. There were a handful of us who were there, and we realized we wanted to do this in Chicago. So we reached out to you and to Brad and said, “Hey, will you do this in Chicago?”

I remember you came up to Chicago with Shaun, the managing director from the Boston program. We talked about setting up Techstars in Chicago, and then you pulled me aside and said, “We’re kind of busy. It’s under the radar, but we’re launching New York and Seattle. We don’t have the bandwidth to do this. We’re really focused on quality over quantity. We think you should do it. We’ll share docs and best practices with you, but it’s gotta be your thing.”

A handful of us—Sam Yagan, I2A Fund, and Sandbox Industries—decided we were going to do it. We launched an accelerator called Excelerate Labs just six months later. We ran in 2010.

You were super helpful. I remember we were on the phone with you asking questions all the time. And it was a great class. It did amazingly well. We did it again a second year, a third year, and then, at the end of 2012, Brad came up to Chicago and told us that he loved what was going on in Chicago.

Brad said, “You’ve got all this activity in the ecosystem, with 1871 and more, and we really want to have a presence here for Techstars, but we don’t want to compete with you. Would you consider joining forces and changing the name on the door?”

I thought it was an awesome opportunity to join the Techstars Network and have a reach that was much bigger than Chicago. We wanted to be part of that big network of mentors and investors and entrepreneurs.

It came full circle and we became Techstars Chicago.

It was a couple of years after that, 2014 or 2015, I think—Next Big Sound was acquired by Pandora, and that was awesome for those guys. It was a great event. It was great for the investors.

I got a nice return on my investment, and Alex sent me a really heartfelt handwritten note. He talked about how he wouldn’t have been where he is without that first class and without my support and mentorship. I was reading it, and while it made me feel warm and nice, something didn’t feel right. It just didn’t settle right. It took a minute for me to realize—wait a minute, I wouldn’t be where I am if it weren’t for Alex, David, and Samir having found Techstars and introduced me to that program.

When I look back at my personal trajectory over the last 10 years, the seminal event was Boulder Demo Day, August 6, 2009, when this ‘Aha’ moment happened of, “Oh my God, I want to be part of this network. I want to help entrepreneurs like this.” Without that, I wouldn’t have run an accelerator, I wouldn’t have run a venture fund, I wouldn’t have invested in all these companies. I wrote Alex back a note telling him: you’re mistaken, you’ve had a bigger influence on my life than I’ve had on yours.

David: Wow. What an incredible story.

I think a lot of people take this idea of Give First, and they know it’s not transactional, but if I help you, you know, someday it’ll come back to me. What I just heard is a story of Giving First coming back to everybody in different ways, right?

Because I feel the same way. Having the chance to work with you and building the Techstars brand in Chicago. And the Next Big Sound guys are coming back literally a week from when we’re recording this to help us with some new company ideation talks, and they’re investing now—they have Next Big Ventures. That’s their venture fund. That’s right.

It’s a network of effects that have happened because of the early Give First of you helping them in class and Techstars helping accelerate them a little bit early on—it just continues in this virtuous cycle. Give First is so much more than: I’ll do one thing and I’ll get something back. You just never know how it’s going to build upon itself to get really powerful for everybody involved.

Troy: I never would have imagined where this would have taken me when we first started. Excelerate Labs didn’t have any office space, didn’t know what a Demo Day was. We didn’t even have internet. We use wireless modems hanging out the window to provide internet to 30 founders. It was pretty ridiculous. Today, it’s pretty awesome to see all the companies that have gone through the program, and to be part of that worldwide network to help entrepreneurs.

The ripple effect

Troy: The first year we did Excelerate Labs it was really fun and new and it felt like we were building something cool. Then the second year we were doing it, and we didn’t have a budget, and I think that year I got paid less than a Barista at Starbucks. You know, my wife was a little pissed at that. But I was in a position where I could afford to do it. I wasn’t worried about how it was going to pay rent next month. It turned out that that decision to build Excelerate Labs, now Techstars Chicago, paid such huge dividends in the long run.

I never would have been in the position I’m in today without it. I wouldn’t have been offered the positions teaching at Booth or at Kellogg that I did. I wouldn’t have been able to start a venture fund. I mean, I’m sure it would have been fine, but I can trace so much of where I am today and the entrepreneurs I’ve gotten to engage with and to help to that early decision to volunteer time and start this thing called Excelerate Labs. It has had such an impact on my life and hopefully a ripple effect impact on dozens and dozens and dozens of others as well.

David: No doubt about that ripple effect. And hopefully any baristas listening are not offended.

Rapid Fire Round

David: I’m going to ask you four quick questions. You rapid fire answers. We just want to get people some new ideas.

We’ll start with this. Other than Chicago, what’s your favorite city?

Troy: I would probably say Wellington, New Zealand. I love New Zealand. I love all of the diversity of nature that it has to offer. Wellington has this cool little pocket of interesting people, cool coffee shops, a startup ecosystem. If I could move anywhere in the world with a snap of my fingers, it’d be Wellington.

David: I may see you there. It’s not a long drive from Queenstown, which I love.

What’s a great book you’ve read recently that you would recommend?

Troy: How the Internet Happened, which tells the story from the first browsers all the way through the launch of the iPhone. It was fascinating to me, having lived through all of that, to hear the inside story of what was really happening inside and how. All of those steps from MySpace to Facebook—they all impacted our lives in such incredible ways. I’ll never forget the first time I saw the first iPhone, I was like, wait, you have a phone that has no keys on it? That was just the craziest thing. Now we just accept that standard. It was a great book.

David: Okay. We’ll check it out. What charity would you urge people to get involved with?

Troy: Lurie Children’s Hospital of Chicago. My daughter had a pretty serious health issue 10+ years ago, and she had brain surgery. She is an amazing kid and has done amazingly well—she’s awesome and perfect and about to go off to college. We attribute that success to Lurie Children’s Hospital. Every year we try to support them the best that we can. I think that there’s nothing better we can do than to support future generations, whether in their health or their education. I’m always looking to support the next generation.

David: Awesome. Last question. Outside of your immediate family and, of course, present company, who’s the most interesting person you’ve ever met?

Troy: Probably one of the most interesting people I’ve ever met was Leon Lederman. Many people won’t recognize him. He was a Nobel laureate and a physicist. He invented the term ‘the God Particle,’ and he passed away recently. He was an amazing man, first of all, incredibly smart. I got to sit down at dinner with him and talk with him about any topic in physics. He had such passion and drive and creativity. And then he turned that into creating something amazing for the state of Illinois, which is the Illinois Math and Science Academy, a publicly funded high school. It’s a boarding school for the top math and science students in Illinois. Every year they take about 200 or 250 students, and it’s had a huge impact.  So I think Leon Lederman was one of the most interesting people I’ve ever met in person.

David: Super Cool. Troy, thank you so much for sharing. Congrats on everything you’ve done in Chicago. And of course everybody should check out MATH Venture Partners. Thanks for being here, Troy.

Troy: Thank you for all you’ve built with Techstars.

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