Strong mentorship was essential to Kesha Cash’s journey to becoming an impact investor. Her mentors Gave First to help her—and now she’s Giving First to diverse entrepreneurs through her Impact America Fund.
Kesha Cash founded Impact America Fund in 2013 with a goal of investing in software and tech enabled companies that have a positive benefit on underserved communities in America. In 2018, she was named one of Fast Company’s 100 Most Creative People in Business.
She went to Columbia Business School knowing that she wanted to start a fund that invested in diverse entrepreneurs, and it was there that she met Josh Mailman, founder of Serious Change, who became her mentor.
As an impact investor, Kesha Gives First every day. But she got to where she is today because of others, especially Josh, Giving First to her—empowering her, teaching her, mentoring her, and ultimately encouraging her to go out and start her own fund.
Companies and resources mentioned in this podcast:
Serious Change LP
The Wisdom of Finance: Discovering Humanity in the World of Risk and Return, by Mihir A. Desai
Edited highlights from the conversation:
The best mentor relationships become two way
Kesha: I had the opportunity to meet Josh Mailman [founder of Serious Change] at Columbia Business School. His family endowed the Mailman School of Public Health at Columbia and I started to work with him during my last semester at Columbia Business School.
This was, gosh, this was in 2010. I’d never met an angel investor that was interested in mission driven companies. I met Josh and Josh was a 60 year old at the time, you know, and a Jewish white man. We had this meeting and he expressed a sincere interest in moving more dollars into mission driven entrepreneurs of color based in the U.S., so we connected in many ways around that mission and I started to work with him. I volunteered during my last semester to identify companies that would fit the thesis of Serious Change. More specifically we were looking for entrepreneurs of color, and we made a number of investments together. What started out as a semester of volunteering ended up being a three year initiative within Serious Change to identify more of these companies.
Rod [Robinson, founder of ConnXus] was one of the investments that Josh and I made together. ConnXus was one of the investments that turned on the light bulb for me in regards to this thesis of there are tech solutions out there that can address inequities within systems. In the case of ConnXus, really looking at diversity and small businesses and the relationship with supply chains at large corporations is obviously very exciting. That early investment in Rod at ConnXus and a few other entrepreneurs that were using technology solutions became the thesis for Impact America Fund One. I was thankful for the continuous support by Josh Mailman and Serious Change. So that family office created space for me to learn, to grow my network, and to refine my thesis for Impact America Fund.
David: It sounds a bit like Josh was somewhat of a mentor, but like the best mentor relationships, they become two way, and I’m going to guess he’s learned a lot from you over the years as well.
The godfather of impact investing
David: Rod said it’s super clear to him that Josh, who he viewed as a pioneer of impact investing, has probably passed on a lot of knowledge and expertise to you. Talk about a little bit about that relationship that you have with Josh and maybe some things that you’ve learned from him or that he’s learned from you over the years.
Kesha: I call Josh the godfather of impact investing. He’s been at this for a very long time, before the term was sexy. We’re certainly happy that it’s a mainstream term now, but Josh and friends started this work over 30 years ago. He’s one of the cofounders of the Social Venture Network, of Investors’ Circles. It was really Josh and his colleagues, including folks like Ben and Jerry’s back in the day, saying, hey, there’s a better way to build businesses. There are ways for us to move our money that are good for society. I’m really blessed that I had the opportunity to meet Josh and work directly with someone. I learned from the godfather of impact investing about building this ecosystem and being catalytic.
Before I met Josh, I met people that knew Josh. They’re like, Josh is this radical, you know, in the best of ways. As an angel investor, he’ll sit down with someone, he’ll hear their idea and write them a check.
What I learned about Josh is that there’s a lot of thought process in writing that check. He’s really good at tapping into someone’s intentions. And we don’t always get it right, but I would say Josh has a gift for understanding the intentionality around a founder’s mission or business idea. What I’ve learned through him is that while that intentionality is extremely important in traditional business, I would say it’s even more so in impact investing. Understanding the founder’s intentionality and their reasoning for wanting to wake up every day to do this is truly important. That’s one of the many things that Josh taught me.
He’d ask me after meetings: do you think this person’s a good person? Which is a loaded statement for him because there are nuances as to what we mean by a quote unquote good person. He’s just good with people and understanding human nature.
He’s also extremely good at networking. He knows everyone across different industries. He taught me the importance of showing up at an event. Don’t talk to people you already know—you’re here to network and to do that in different spaces. When we worked in New York, we’d take trips to Harlem to visit an entrepreneur or go downtown, and it was just amazing to watch him be able to adapt to different environments and to really be present in those environments to understand what was happening from a cultural standpoint. I learned a lot from Josh about people and being present and truly understanding the atmosphere that we were in.
As for what he learned from me, you’d have to ask him about that. But he continues to be a great friend and mentor and I’m very honored to have him in my life as a mentor and as a guide through this process.
Go out and do it on your own
David: It sounded like Josh was a big proponent or fan of you launching off on your own with your next fund and activity that you’re doing now. Why would he support that? It sounded like he was a big fan of: Go out and do it on your own.
Kesha: That’s a great question. We met in 2010. After Wall Street and prior to Columbia Business School, I worked with very small lifestyle types of businesses in Los Angeles. The majority of those companies were led by entrepreneurs of color. That’s where I discovered this amazing talent that was disconnected from resources, and I applied to Columbia Business School with this idea of supporting and helping to build this ecosystem and getting more resources to diverse entrepreneurs. Right.
When I met Josh, I told him that I applied to business school with this idea. My business school essay said I wanted to raise $3 million to invest in these early stage companies. So when I met Josh, he’s like, Look, you know, you don’t have a track record. It’s gonna be really difficult for you to actually raise a fund. At this point, work with me. I have the capital, we can do deals. You go and find those deals, we’ll build it and they’ll come. The good thing about Josh Mailman is that he takes action. He’s catalytic, he takes action, he’s spent years trying to figure this out with me.
So we met and he understood my purpose and intentionality and we got to work. What started out as a, hey, come work with me for a year to identify some investments to do some deals, turned into a three year partnership at Serious Change. We got to the point where I said, Hey, I think I’m ready to create this independent fund, and he and Serious Change supported that. From our initial meeting, there was the intent that I would at some point spin off and raise an independent fund. And he held true to our handshake agreement. I’m thankful for that.
David: I mean, that’s a classic example of Give First. Knowing that he was going to train you up and then lose you—but that in another way he would get back from it because you would be carrying some of that business philosophy out into the world. Maybe even improving it a little bit.
The bottom line for impact investing
David: Any time I talk to someone who identifies as an impact investor, I like to throw out some data that we have here at Techstars, and you’ll probably identify with this.
We now have the Techstars Impact Accelerator down in Texas. We work with the Nature Conservancy. We have a farm to fork program. So we are doing more and more in quote unquote the space. As we did that, we really looked at the definitions of what we are looking for in those programs and found that 15% to 20% of what we’ve been doing all along falls pretty cleanly into this category of impact. And we pulled that cohort out. We’re investors in about 2,000 companies. So we’re talking a couple of hundred companies, maybe 200-300 companies that would meet this impact definition. And as a cohort they were performing better than the total cohort of all companies. So impact is not just about that second bottom line. It’s also about that first bottom line. And I’m sure you would agree.
Kesha: That’s true.
Rapid Fire Round
David: What’s your favorite city everybody should visit?
Kesha: New York City
David: Awesome. That’s a popular one. I think everybody wants to go there if they haven’t been there. I know why.
Kesha: I’m taking a red eye there tonight, so it’s top of mind.
David: You’ll be nice and rested tomorrow, I’m sure. How about a great book that you’ve read recently that you want people to know about?
Kesha: Oh, I’m almost finished with it. It’s called The Wisdom of Finance.
David: Any charities that you’d urge people to get involved with or take a look at?
Kesha: The Sponsors for Educational Opportunity. I participated in this organization while in college and was placed in my Wall Street position, and I think they are single handedly responsible for diversifying Wall Street. I encourage everyone to support them.
David: That’s awesome. As a thank you for being on the show, we’re going to do a donation to them, and also do one to the Techstars Foundation, which is focused on diversity and inclusion in tech, in your name, if that’s okay.
Kesha: Oh, excellent. Thank you. That’s wonderful.
David: We appreciate you coming on the show. Last one. If you have, if you could have dinner with anyone, they don’t have to be alive, who would it be?
David: It’s more fun if they’re alive. But let’s imagine that you could do it at any point in history is what I mean by that.
Kesha: Given the times that we’re in right now, I want to go back and be part of the conversations with some of our great civil rights leaders. Malcolm, Martin, some of the philosophers, I’m kind of going back a little further. W.E.B. Dubois. I think we’re in cycles. You can obviously read the books, but to be able to sit down and understand the philosophy and the lessons learned from different eras in time, I think would be extremely helpful right now.
David: That’s a whole party. I’ll give it to you. We’re looking for one person, but you can have a party. That’s cool.
Kesha, thanks so much for taking the time to join us on Give First. Best of luck with Impact America. Really appreciate you joining us today.
Kesha: Thank you, David, for all that you do as well.
From Google for Startups to Startup Weekend to Rise of the Rest and beyond, Mary Grove is passionate about community-driven change, and helping make it happen.
Mary Grove is passionate about community-driven change, and this theme has guided her entire career.
She joined Google when it had only 2000 employees, and by the time she left it was up to around 75,000. Over 14 years, she went from working on the IPO deal team to starting Google for Startups.
Google for Startups’ very first partner was Startup Weekend, which Mary helped to spread from a few dozen to 140 countries, vastly broadening its impact.
Today, she’s a partner at Rise of the Rest Seed Fund, the co-founder of Silicon North Stars, and on the Advisory Board for the Techstars Foundation.
Mary talks with Brad Feld about the joys of empowering entrepreneurs across the globe, and the transformations she has seen.
This is #GiveFirst at scale. We love it.
Companies, resources, and people mentioned in this podcast:
Becoming, by Michelle Obama
Be Fearless, by Jean Case
Google for Entrepreneurs – became Google for Startups
UP Global – acquired by Techstars
Edited highlights from the conversation:
Google for Startups, Startup Weekend, & Techstars
Brad: Let’s start off by hearing a story about how you ended up at Google working on Google for Entrepreneurs.
Mary: Sure. I had the great privilege of joining Google in 2004. I was coming out of Stanford on my way to law school, and I thought I would just pause for a year or so and take a job at what was then a small company called Google. I joined the legal team back in 2004, and I actually worked on the IPO deal team for my first year, which was a fascinating and wonderful experience, with the process of going public and really being part of a very fast growing organization.
When I joined Google, we were about 2000 people. When I left almost exactly a year ago, Google was about 75,000 people. So it was a great 14 year run where I learned a tremendous amount, and I’m super grateful for the experience.
Brad: Going from a startup of 2000 to 75,000 employees is quite a change.
Mary: It really was. And it was really remarkable, Brad, to watch our co-founders Larry Page and Sergey Brin on that journey and see how they were able to scale the culture.
As the organization scaled to be that large, I had the opportunity to travel to probably about 40 different countries to visit Google offices, and I was always so struck by the fact that each office had its local flavor and honored the local country, but really also had such a consistency of culture and spirit. I’m happy to talk more about some of those values, which are certainly core core lessons that I carry with me today.
Brad: You were at Google for a long time, but there was a shift in your role at some point from the operating business in the legal group to this new thing that got created called Google for Entrepreneurs. My guess is many of our listeners know what Google for Entrepreneurs is, but maybe talk about it for a few minutes, how it got started, and what your initial involvement was.
Mary: After my work on the IPO, we were a public company. I then spent the next six years as a part of a team called new business development, which was led by Megan Smith, one of Google’s most amazing leaders. I worked for her for six years and that team was really working on early stage product, business development, expansion into emerging markets. That’s where I truly fell in love with the company—certainly the culture, but also what was happening on the business and product side, particularly around access.
I spent a lot of time working on emerging markets and very emerging markets. We had a project called the bottom 20, which was looking at the twenty least connected countries in the world from an access and infrastructure perspective. We put together a cross functional Google team focused on how Google could help both from a Google Inc. perspective and also from a Google.org philanthropic perspective. I had the opportunity to spend time in places like Iraq, Afghanistan, Pakistan, Gaza, the West Bank. Really, through that journey, what was most exciting to me was the opportunity that entrepreneurship created in these markets.
Google could have a direct impact. If we could help fuel and foster startup communities, that would build a platform for true economic development locally and globally.
Fast forward to 2011. Our senior leadership team at Google recognized that so many teams across Google were dabbling in activities supporting startups, but there wasn’t a consolidated, proactive effort around this. I had the opportunity to give some thought to that, based on the work that I had been doing on Megan Smith’s team, and essentially pitch what became a new team.
That’s Google for Entrepreneurs, which today is called Google for Startups.
Essentially our mission was to bring the best of Google’s resources to accelerate the growth of startups and entrepreneurial ecosystems. That included our capital, our talent, our technology. That’s actually what led me to the journey to meeting Startup Weekend and ultimately Techstars. Google for Entrepreneurs was a really amazing part of my Google experience. Through that we partnered with about 60 organizations, who I really believe are best-in-class groups like Startup Grind, Startup Weekend, Techstars. You name the continent, we were able to be there supporting the greatest community leaders. And it was a great time.
Brad: Our first introduction was made by Mark Nager around Startup Weekend on some kind of video thing that we did together around 2011-ish talking about startup communities. I’m not 100% sure that’s right. But that’s what I kind of vaguely remember.
Mary: I think we did a Google hangout.
Brad: What are some of your recollections around those early experiences that you had with Startup Weekend and it’s evolution towards what ultimately became UP Global?
Mary: Startup Weekend has a truly dear place in my heart and my memory. We started Google for Entrepreneurs back in 2011, and immediately we believed that partnerships would be a fundamental part of the work. There would be some direct work that Google did in the field, but really the way to get scale and impact was by working with best-in-class partners.
The very first partnership we ever signed was with Startup Weekend in 2011. I had attended an early Startup Weekend a couple of years back when I lived in New York City. I was really, really impressed with the format, so I caught up with Mark Nager and told him that we just believed in the power of this 54 hour event format and the fact that it was all about community-driven change. Our partnership really was to enable Startup Weekend to take that model and expand it from a few dozen countries ultimately into 140 countries. That was important in Google for Entrepreneurs’ history, because we found a partner who so fully aligned with us from both a mission and an execution perspective. They assembled a fantastic board with really great talent, which is how I was connected to you—and the rest is history.
Brad: What was your first memory of Techstars and your first involvement with Techstars?
Mary: We got very involved with Startup Weekend, which ultimately became UP Global, as you mentioned. Then when UP Global and Techstars merged, our relationship only continued to grow from there. Through Google for Entrepreneurs, we expanded the partnership with Techstars to continue to support those programs, as well as additional work including the Techstars Foundation. I was very struck by the scale and the breadth of Techstars in terms of the geographic reach, the sector reach, and the consistent quality across the board, which I think is really, really hard to achieve at scale.
Another touch point I have now is in my new home city of Minneapolis, where this past year I served as a mentor in both programs here, both the Techstars Retail and the Techstars Farm to Fork accelerators. Those were really fantastic—to get to actually see a full program from start to finish, to meet every one of the companies and even follow up with them. I’m still in touch with some now in due diligence for investment opportunities, and that’s just from two of the programs. I continue to enjoy that relationship.
The third piece is that I am on the advisory board of the Techstars Foundation, which I just absolutely love. I think that’s the embodiment of the Gift First mantra, which Techstars has always had. Formalizing that in the form of a foundation that not only supports entrepreneurs directly, but supports the community leaders who enable them—there are so few groups out there that do that. I myself also run a nonprofit called Silicon North Stars, and I know firsthand that it can be hard to find organizations who actually fund the organizations doing the work. I really applaud Techstars for the foundation initiative.
Rapid Fire Round
Brad: What’s your favorite city in the world?
Mary: I would say New York City. I had the opportunity to live there for five years during my time at Google, and I just felt like it was an extraordinary melting pot of hopes and dreams, energy and electricity, and the exposure to so many different cultures. It’s not a city that I spend much time in these days, but it is very close to my heart and one that I deeply love.
Brad: Great. Second: an impactful book that you’ve read recently.
Mary: I’m just about to finish up Jean Case’s book Be Fearless, which is her newest release. We talk a lot about how to create a strong culture of entrepreneurship. I do believe that so much of it is the culture. By that I mean this lack of fear of failure, embracing this notion that it’s okay to put it out there, to iterate quickly, to get harsh feedback immediately, and to pick up and keep moving on. I really appreciate all of the stories that she weaves in. They’re very practical advice that is super helpful for any entrepreneur, but especially for those who are just starting out. It can be a daunting journey.
Brad: I read a prerelease of the book and I thought Jean did a fantastic job. I’d echo that recommendation: it’s inspirational as well as instructive. Jean did a great job of not just curating the stories but also weaving her own experience through those stories. It’s a fun one.
Next up: favorite charity and why?
Mary: This is a very biased answer, and I’m not sure if I’m allowed to self plug here, but the charity that is dearest to my heart is a nonprofit called Silicon North Stars, which my husband Steve and I started together in 2013. At the time we were both living in Silicon Valley and working at Google. We recently moved to Minnesota. Steve is from here originally. I was born in Iowa and we both have a ton of family here in the Midwest. We started to look at Silicon North Stars as a way to really build a bridge from the communities we were from to where we lived. Our mission is to inspire and educate young Minnesotans towards futures in tech. We specifically target economically underserved youth. Every year we choose a cohort of a couple of dozen rising ninth graders and we take them on a trip to Silicon Valley for a week, expose them to all the magic there, come back to Minnesota, and then provide them with year-round programming and support for the next four years of high school until they start college.
This was a personal passion project. We bootstrapped it because we were both very privileged to come from entrepreneurial families, who to me embody the American dream. We wanted to give others that opportunity as well. We’re very grateful that the organization has scaled. Now we’re back in Minnesota, so we’re actually expanding the program for 2019. I should mention, Brad, that Techstars has been hugely helpful locally.
Brad: Homestretch. Last question. Who is a person that you’ve never met—either alive or dead—who you’d love to have dinner with?
Mary: I would say Michelle Obama. I’ve also just finished reading Becoming, her memoir, and I have always been a huge fan of the causes that she advocates for. I would love to have the opportunity to dine with her and to really pick her brain on how to apply some of those themes to our daily work and our daily life.
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
Next Big Sound – acquired by Pandora
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.
How did Sphero CEO Paul Berberian make the number one toy in the world? Sphero got to make the BB8 toy robot because of a connection made during a Techstars accelerator. That’s the power of the network. Hear him tell that story, and more.
Have you ever been mobbed in Times Square, like a rock star? Paul Berberian, CEO of Sphero, the company that makes BB8, at one time the number one toy in the world, has.
Paul talks about how mentoring and Give First were essential to Sphero getting the BB8 gig.
He loves mentoring as well, and describes the experience of being a mentor and having a positive experience on someone’s life as “addictive.”
Listen for more on the transformative nature of mentorship—from both sides—plus more behind the scenes details on how one of the best loved Star Wars toys came to be.
Companies and resources mentioned in this podcast:
Raindance Communications – acquired by West Corporation
Edited highlights from the conversation:
The biggest lessons from being a mentor
David: We like to talk about experiences of mentorship on this show because we feel like a lot of people really get that Give First experience through mentorship, whether it’s something they’ve learned from someone or a way that they’ve been able to help someone else. Can you tell us the biggest lesson that you’ve learned about being a mentor or trying to help someone else?
Paul: I have two really big things that come to my mind when it comes to being a mentor.
The first is that it really doesn’t take a lot of energy, right? I don’t mean that it’s trivial, I just means that it’s actually pretty easy to be a mentor and to have a positive impact on someone’s life. It’s just being honest and listening and sharing your experiences so that hopefully someone can benefit from them.
The reason I share this is I’ve had people come up and tell me that I talked to them three years ago and said something really impactful. And I go, “I don’t know who you are. You sure it was me who talked to you?” They tell me, yeah, we met at this place.. and they have to go through this really long process to describe where we met. Finally my memory kicks in, and it’s amazing how something so simple and so small could have an impact on someone’s life.
The second thing I reflect on about mentorship happens oftentimes when I’m mentoring a young startup. I might be struggling in my own business, and they’re doing something that just doesn’t jibe with me—but they’re having success, and they don’t realize that while they’re talking about something they’re doing and they’re talking to me as a mentor, I’m secretly taking note.
I’m thinking, oh my gosh, look what they’re able to do with, you know, two matchsticks and a piece of bubblegum. We’re going to spend, you know, $100,000 trying to do something that won’t be nearly as effective. I’ve had numerous experiences like that, where the scrappy nature of a startup inspires me. You kind of lose touch with that scrappiness as you build a business. Sometimes it’s great to have that touchstone and see what young people are doing. I get a lot out of it.
Advice that changed your life
David: Is there something that someone shared with you that changed how you think about business early on?
Paul: I’ve been reflecting on this because I knew I was coming here today.
Jack Tankersley was one of the early Colorado legend venture capitalists and he was still an active venture capitalist when we first moved to Colorado back in 1994. We were approached to sell our company in 1995. We met Jack Tankersley and his partner Steve Halstedt at Centennial Ventures and we were faced with potentially selling our company or taking money from them. Jack could have been very selfish at that moment and said, “Let’s put some money into your business, let’s grow, build something big.” But he approached the situation from a different perspective; he didn’t approach it from a business perspective. Instead, he had a dialogue with me and my partners, and he asked about us personally. Are you married, do you have a mortgage? Do you have any debt?
He found out that we all had young kids, and we were all saddled with an incredible amount of debt, because we put our hearts and souls and our credit cards into the business.
Once he’d learned all this, he basically said, “You guys are smart. You’re going to do this many times in your life. Come see me after you sell your company and put some money in the bank. You’re going to be a much better entrepreneur after your first exit and success.”
That may not sound like an amazing piece of advice. But at that time it was very profound because I had never thought of myself doing this multiple times. And here’s someone who says, “I’ll be there the next time.”
It made me think about my career. I was around 28 or 29 at the time. His advice made me think about my career as the beginning of an arc. I’m gonna be doing a lot of different things in my life, and it’s okay to let go at this time of something that was my baby and to think about the next thing.
You become attached to something and it’s important to hear that it’s okay to move on.
David: There’s also that relationship piece, right? Where he was saying, “I’ll be there, too.”
Paul: Yeah, exactly. And that was really powerful. He was an investor in our next round and there were a couple of pivotal times over the course of our next business, which became Raindance, when he was there again, offering sage advice. He had a big impact on shaping me as an entrepreneur, he probably doesn’t know that.
Brad & David: We will make sure he hears this. We will spam him.
Brad: Jack is somebody who I consider a key mentor of mine. He was somebody I met very early in my own personal journey as an investor. I learned an enormous amount from him in the first three, four, five years of my own investing, both with investments that we got together and just talking to him and getting feedback from him and listening to him. He’s a great example of somebody who is very invested in relationships and less focused on optimizing for the transaction.
Paul: He really is. He really is all about the people.
The origin story of BB8 & getting swarmed in Times Square
Brad: Tell us about something that really sticks in your mind as a magical moment.
Paul: I’ll reflect on one that’s pretty recent. People may know of it. Sphero was involved with the Techstars accelerator program with the Walt Disney Company. It was back in 2014 and ‘15, and we were partnered up with mentors from the executive at the Walt Disney Company, and one of them was Bob Iger [Disney’s CEO], who met with all of the teams.
I remember the meeting with Bob Iger. Each company had 11 minutes with him, and in our 11 minutes he shows up and tells us about this new Star Wars movie coming out. There hadn’t been a new Star Wars movie in around 10 years. He says, “I know everything about you guys. We got a short amount of time, but let me show you something.” He pulls out his iPhone, and he shows us this new character.
It looks a lot like the product we were building at the time, which was a robot bobble. He says, “Can you guys make this into a toy?”
Of course we said, “Yeah, of course we can do that!” That’s the origin story behind BB8.
We went on to make BB8 and Star Wars: The Force Awakens was a big, successful movie, and we were the number one toy in the world.
I remember one very specific moment in time. There was an event in New York City at the Disney store when people were lining up outside the store at midnight to go buy BB8 when it first came on sale. The line went around the block. I was there as the company CEO to announce it.
I was literally swarmed in Times Square. I felt like a rockstar at that moment. I realized it was just a very brief moment in time, that it wasn’t gonna be here forever. But that was a pretty special moment. That was a fantastic moment.
David: Maybe they advertised it as Bob Iger was going to be there.
Paul: I think it was BB8. There were a lot of folks dressed up as storm troopers and Darth Vader.
David: Star Wars people are crazy. I mean, they show up.
Quick Fire Round
Brad: Let’s shift into a quick fire round.
David: We love Harry Stebbings. We love his show, Twenty minute VC. We’re totally ripping this off. We like to say that every time.
Paul: I did one of his shows way back when.
David: All right. A favorite book that you’ve read in the last year.
It was an audio book and I just finished it. It’s called Power Moves by Adam Grant. He interviews people at Davos talking about power and the section where he interviews women leaders is absolutely powerful. I’m going to go on for 13 seconds more because one of the most powerful things out of that book was the women leaders who said their success was because a man decided to mentor them so that they could elevate their careers. The fact is that if we want to see women in more powerful positions, we have to commit to mentorship, so that they can be successful. We can’t only go out to lunch with the guys.
David: Your favorite charity that you’ve supported and why.
Paul: My favorite charity is the Community Foundation.
David: A new startup people should check out.
Paul: I mentored Goally in the most recent Techstars cohort, and I think what they’re doing to help kids stay focused and get their lives in order is awesome.
David: A city that everybody listening has to visit.
Paul: Hong Kong.
David: Hong Kong. Awesome. Paul, thanks so much for being on the show with us today. We appreciate it.
Paul: Thank you.
Entrepreneur, investor, and Techstars board member Wendy Lea remembers the beginnings of Techstars, her first encounters with #GiveFirst—and how mentors have changed her life.
Wendy Lea is a longtime entrepreneur and investor, as well as a board member and mentor at Techstars. With David and Brad, she digs into some of her first mentoring experiences and reflects on a time when a mentor changed her life.
Wendy was early in her career and had just been offered a promotion that would cause a lot of change in her life, and she was hesitating. Her mentor told her: the risk of saying no is very high. “If you say no, you’re playing small. You have a lot of potential, and you need to go explore that potential.”
She did, and she traces her success back to that encouragement and good advice.
Listen for more about the risks of saying no… and saying yes.
Bonus: Listen to Wendy, David, and Brad reminisce about the first Techstars class.
Companies and resources mentioned in this podcast:
EventVue – closed
Get Satisfaction – acquired by Sprinklr
OnTarget – acquired by Siebel Systems
Siebel Systems – acquired by Oracle
An edited transcript of the conversation follows:
David: We’re really excited to have Wendy Lea here as a guest today on the podcast. Wendy is a board member at Techstars, and she recently moved back here to Boulder after spending four years in Cincinnati as the CEO of Cintrifuse. Welcome, Wendy.
Wendy: Thanks a bunch. That was a fun gig by the way, Cintrifuse. I’ll end on that.
David: Spend a few minutes giving us your origin story.
Wendy: A little bit about my background might help those of you listening grok my experiences and where they come from. My big success came with a company called OnTarget, and it came after lots of professional training in large companies. With OnTarget, three or four of us worked like dogs to make that work around the world. We owned it 100%, and we sold it for $150 million to Siebel Systems in 1999.
After that, I worked for Siebel, which was fantastic. I loved that because I learned a lot, and then I took that experience and started doing new things with it, for example, really working with venture-backed startups. That was very different: the risk, the reward, and the kind of mentoring that startups required. It was this that brought me to Boulder. In Boulder, I worked with companies like Lead Works—formerly Duo—and also Numerics.
Then I went to California. I made a bunch of angel investments and I did a big tour of duty at Get Satisfaction. Get Satisfaction was a big love, my biggest love in all of my work life. It didn’t turn out as planned, but it was quite remarkable. I’m back here in Boulder now, and proud to serve on the Techstars advisory board.
Brad: Wendy, would you talk a little bit about how you got introduced to Techstars and what your involvement with Techstars has been?
Wendy: At the very beginning it was an ask from you to plug into the community. From there you introduced me to David, and David told me about his big idea about bringing entrepreneurs and mentors together. That’s the first time I heard about Techstars, and that was the first cohort. I’ve hung around with a lot of mentors, and I became plugged in through the community that Techstars created here in Boulder.
David: Back then, that was really the first super visible example of Give First in Boulder. There were so many mentors who were trying to help that first class of 10 companies—which turned out to be a great class—and get this whole mentorship-driven accelerator thing going.
Tell us about your biggest lesson as a mentor.
Wendy: My biggest lesson as a mentor was with a company called EventVue. The founders, Rob Johnson and Josh Frasier, had an idea that was completely easy to understand. It wasn’t complex and crazy. I really got it and I liked what they were doing.
They were very, very early in their life cycle as entrepreneurs and they were impressionable. If a mentor told them something would work out, they really believed it. It was a struggle because I didn’t want to dispute other advice they were getting, but I suspected that the situation wasn’t going to work out. That was tricky, because you want to be upbeat. I believed in what they were building, and they were working like dogs. Of course, it didn’t work out.
Now when I see them, they always say, “Oh, I’m so embarrassed when I look back and think that I was so cocky.” And I say, “You know, it happens.”
David: So you were trying to manage that dynamic.
Wendy: I was trying to manage their expectations. This was before all the cool modules that we have now in mentoring, it was just us bushwacking through, doing what we could to give back. It was tricky. I did what I was taught as a young woman: ask a lot of questions, and see if they’ll tune into that reality or not.
Brad: Wendy, you’ve been involved in lots and lots of companies, both as a founder or entrepreneur, and you’ve been brought in by a bunch of startups to help by serving on their boards. You’ve also been a startup investor. When you reflect on all of those experiences, what’s the most fun you’ve had with a company?
Wendy: Building out the leadership teams.
Brad: Can you talk us through an example?
Wendy: On the venture backed side, it was awesome building out the team at Get Satisfaction. It was also hard.
Brad: What were some of the awesome things?
Wendy: We were really trying to figure out the match between the skills and knowledge that were being represented, and the needs we had on the team. We hired someone, and it turned out we brought in the completely wrong person.
He didn’t know how to get his hands really dirty: sit with the engineers and talk with them directly about what they saw in the code. The code needed to be refactored. It was going to be an expensive proposition. We all kind of knew that, but the guy was saying all the right things. He affiliated more with the product managers, and not with the engineers, and it caused problems.
That was a significant turning point for me, because I don’t have that background. I had to listen and learn and ask the founders. It was exciting and scary and costly when you did it wrong. I made a big mistake there and it really cost the company a lot of time and money.
David: Yet it was awesome.
Wendy: It was awesome.
David: Sounds like you learned a lot there.
I’m curious if you have an example from your career, Wendy, where somebody gave you some advice early in your career that really changed a lot for you?
Wendy: I’ve got one example from early in my career and one from later.
I had an opportunity as a young woman, in my mid-twenties. I got a promotion that required me to move from Jackson, Mississippi to New Orleans. It looked very risky to me. Personally, I’ve gone through a lot of change, so I can deal with personal risk, but I like my professional life to be stable. I was worried about moving and not knowing anyone in New Orleans. My husband couldn’t move with me.
My mentor, who was one of my bosses at the company, said to me, “The risk of saying yes is really very low. The risk of saying no is very high.”
I didn’t get it. My brain was going crazy. He told me, “If you say no, you’re playing small. You have a lot of potential, and you need to go explore that potential. So you don’t know anyone. You’ll meet people.” I’d never thought of that: the risk of yes versus the risk of no.
I told my husband I was moving to New Orleans. Of course he didn’t come. Yes, there was a divorce. Life continues. But that comment about playing small really made me think, and taking his advice changed my life.
The other advice, from later in my life, was from Rob Hayes, who’s a very dear friend at First Round Capital. He was an investor in Get Satisfaction when one of our first term sheets was pulled. The company had no money. We had zero. We were funding it ourselves, we weren’t doing well, and the term sheet got pulled. I didn’t know to be upset about that. I had not had enough experience to freak out when this happened.
Rob understood what it meant, and we met at a coffee shop. He asked me what we were going to do, and I told him that we would keep looking for money and I would invest and we would keep going.
I loved this company, and he was just like, “Wow.” Then he said: “I support you.” For Rob, if I thought there were conditions that we could build around, he was going to support me.
Brad: In 60 seconds or less. What does Give First mean to you?
Wendy: Give without expectation of return.
David: That’s far less than 60 seconds. I’m going to start using that.
The other thing I’d love to hear about is an example in your life where you’ve seen the power of Give First in action.
Wendy: There are lots of those! Here’s one. I was working with some universities in Cincinnati, and we were doing a coaching workshop, teaching people how to do good coaching or good modeling, showing behaviors by doing them. We were working one day in the engineering school, in a coding class. One of my students went over to a young woman and sat down with her. He said to her, “I can tell you’re struggling with this. What can I do to help?”
No one told him to do this, and I didn’t instruct them to run around the room and help each other out. That was good observation and good modeling. I’m really proud of that. It was very natural, so she didn’t feel awkward.
The more we model this behavior—giving without keeping score, and without needing immediate reciprocity—that will change the scope and slope of the work we do. If you model it suddenly and set expectations suddenly, then people lean in. They learn how.
Brad: That’s great. The last section here is something that we lifted from our friend Harry Stebbings, a quickfire round. We’re going to ask you a handful of short questions and we’d love very, very fast answers to each one of them.
David: Let’s do it. Wendy, what’s your favorite book you’ve read in the last year?
Wendy: Small Fry, by Steve Job’s daughter Lisa.
David: Do you have a favorite charity you support?
Wendy: I support the SPCA because I’m a big dog lover.
David: Tell us about a startup you met recently that you think people should check out.
Wendy: I’m very excited about Pipeline Equity, which happens to be a Techstars company, led by Katica Roy.
David: What’s a city that you think people have to visit before they die?
Wendy: I would say Oxford, Mississippi.
David: You did it. You’re through it. Thanks for joining us, Wendy. It’s been a blast having you.
Wendy: My pleasure. Thanks for having me.
Today, I’m excited to announce the launch of the very first podcast from Techstars: the Give First podcast. Brad Feld and I are co-hosting this weekly podcast that digs into what Give First means.
I can tell you that I’m having a great time making it, and I’ve already learned so much from the people we’ve had as guests.
What is Give First?
Give First is one of our core values here at Techstars. It means helping others with no specific expectation of return. It’s not transactional—it’s the idea that if you’re helpful, it will come back to you in completely unexpected ways.
Why Make a Podcast?
This is great, but I know it can sound a little abstract if you haven’t experienced it yourself. You may be wondering if it really works. Do busy people—and entrepreneurs are notoriously busy people—actually stop and Give First?
Yes, it really works.
I hope that you listen to the Give First podcast for insights into how exciting and successful a life and career guided by the principle of Give First can be. Here are just a few examples from the first few episodes:
- Hear Paul Berberian, CEO of Sphero, tell the story of being mobbed in Times Square like a rock star when Sphero’s toy BB8 was the number one toy in the world.
- Listen to Wendy Lea talk about the risks of saying “no” when opportunity comes knocking.
- Troy Henikoff tells a decade worth of Give First stories that all intertwine—and resulted in companies growing, careers thriving, and millions in funds being raised, all while the Chicago startup ecosystem is expanding.
- Mary Grove shows the power of Give First at scale, with her adventures in community-driven change, starting Google for Startups and traveling on the Rise of the Rest bus.
Like I said, Brad and I are having a blast making the Give First podcast. We get to have fascinating conversations with accomplished, generous people. But most of all, Brad and I are making this podcast as yet another way to Give First. We hope that by sharing these stories with you, you’ll be inspired to Give First as well.
Listen now to our introductory conversation, where Brad and I talk about where the idea for Give First came from and what it means to each of us. And subscribe to the Give First podcast!