Rebecca Lovell on career ‘nudges,’ karaoke, & how to be an ally

Do you know how to be a great ally in the workplace? Why all startup founders should do karaoke? What the secret sauce of the Seattle startup ecosystem is? Create 33 Director Rebecca Lovell knows the answers to all these—and more. 

Rebecca Lovell plays, as Brad Feld says, “a very important role in the center of gravity for the Seattle startup community.” Currently Director at Create 33, a resource center for tech entrepreneurs, Rebecca teaches entrepreneurship at the University of Washington and has held a number of roles in Seattle city government, from Startup Advocate to Acting Director of the Office of Economic Development. 

Listen for more of her interesting career trajectory, which has gone through unexpected turns because of “nudges” given by mentors and others, resulting in Rebecca’s strong belief in the power of mentorship and giving first. 

Then keep listening for actionable advice on how men can be allies to women in the workplace as well as Rebecca’s hilarious dive into why all startup founders should do karaoke.

Companies, people, and resources mentioned in this podcast:

Edited highlights from the conversation:

The secret sauce of the Seattle startup ecosystem

Rebecca: As I like to say, the secret sauce of the Seattle startup ecosystem is coffee. And it’s not just because we’re so highly caffeinated, but that can’t hurt. I think it’s that we have this undercurrent of collegiality and collaboration where you can get a cup of coffee with anyone that you want or need to meet. You combine that ethos with the lived experience of entrepreneurs and investors who just raised their hands and said Yes to supporting Techstars. That’s the moment that [Techstars Seattle, which started in 2010] stepped into. And now, you know, almost 10 years later there are 40 coworking spaces, there are 80 engineering centers located in greater Seattle. Facebook has the biggest footprint in Seattle, outside of its headquarters. We’re not just a one horse town dominated by Microsoft or even two horses, Microsoft and Amazon. It’s a really rich ecosystem. But you got here at pretty interesting inflection point in our story about ourselves as a community.

How can men be allies?

Brad: I’ve been very involved in an organization called National Center for Women & Information Technology for a number of years. 

Rebecca: Lucy Sanders, absolutely.

Brad: I was board chair for a while and  worked very closely with Lucy, and I learned a lot about this notion of male advocates or male allies. And I’d love to hear, in your words, how men can help around the issue of diversity and inclusion. From your frame of reference as a woman, how can men be allies?

Rebecca: Absolutely. I gave a couple of examples of when men can use their power and their privilege to promote women. The first case in my own personal history was that recruiter who happened to be a man who convinced me that I was management material and my classmate who was a man who convinced me that I just win things. They both had positions that they leveraged to open a door for me knowing that I would succeed. Those are just a couple of small examples. 

I also think it’s in just everyday behavior and creating a discipline around making room for women. I kind of don’t like the phrase ‘lifting up’ women. What you really need to do is quit pushing us down. But here’s one way you can make room for us. I can’t tell you how many meetings I’ve been in, whether it’s in the tech sector or in city hall, where I’ll be one of just a few women in the room, and men categorically have a tendency to talk over us.

For example, if my colleague Jessica would make a point and the man running the meeting would run over her, I would make a point of saying, “to Jessica’s point,” then repeat what she said—it’s very critical to use her name—and then maybe add my piece to it. This is a technique that men can use. You can amplify women’s voices, but I can’t tell you how important it is to use their name when you do it. If you just repeat what she said, you will instantly be given credit for it. So be mindful of sharing credit, you know, shining a light on the incredibly important voices of women. Those are just small daily practices that you can engage in.

And then I think writ large, if you look at the deplorable share—disproportionately low share—of venture capital investment that women get, part of it is about the institutional bias that might be brought into a partner meeting on a Monday afternoon, where your bias is going to be towards investing in men. But the real issue that was uncovered by Illuminate Ventures out of the Bay Area, Cindy Padnos’ group, is you literally have to take more meetings with women. If you think about the venture funnel, if you take 900 meetings over the course of the year and that gets you to nine deals, you want to start at the top of the funnel by taking as many meetings with women entrepreneurs as you can. 

So that’s a daily behavior change: just think about ways to find and say Yes to meetings with women entrepreneurs, and over time, both by changing the behavior of the men who dominate the VC industry and making room for more women to become investors and lead a VC firms—like Arlan Hamilton and Backstage Capital—that’s when we start changing the narrative and changing the results.

Karaoke as a metaphor for pitching your startup

Rebecca: The point of Karaoke is that it is 40% song selection, and in startup language that’s product market fit. You need to know your range, that’s your product, and you need to read the room, know your audience and try to pick a song that’s gonna resonate with them—that you can sing. That step one, that’s 40%. 50% of it is just selling it, getting on stage and acting like you own it. And that comes down to the grind and the execution that startups face. And if you do the math, that only leaves 10% for talent. 

I love Karaoke, as I said, almost as much as I love entrepreneurship. 

Rapid fire round

Brad: All right. First one. Favorite city in the world other than Seattle.

Rebecca: Well, would it be to visit, to live, to retire?

Brad: Oh, you get to define the way you answer the question.

Rebecca: All right. Just because I have such a hard time unplugging and truly chilling out and getting off the grid, I would say Sayulita in Jalisco, Mexico. I’m a scuba diver and there is no better way to get off the grid than sitting around with great food, amazing beach. This little town probably has as many chickens and dogs as it does people. And I’m almost hesitant to say it because it’s been this beautifully kept secret, but I love it there.

Brad: Second one, how about a book that you’ve read recently that you thought was fascinating?

Rebecca: Yeah, I have been this total podcast and audio book junkie of late and the one that I  just finished up is Melinda Gates’ Moment of Lift, and it’s not for the philanthropy—I think that commitment as well known and the impact is well known. 

I love reading books and learning stories when I can get some new insight. And what I loved about this book was hearing directly from the author—Melinda read the audio book—and she had this, what I think is a real startup-y, entrepreneurial approach to their theory of change. Like they went into the market of the developing world, knowing that there was a global crisis around children’s health and easily preventable diseases. 

Their plan was to focus on kids, but when they did their customer discovery phase, in startup parlance, they spoke with so many women, mothers and learned that the most life changing thing they could do would be to provide birth control for these mothers. So they went in with a set of assumptions, but they did such a great job of listening. They pivoted to where they felt like they could make the biggest impact. That was a wonderful discovery that I got through that book.

Brad: I’d strongly recommend that book as well. I read it a couple of weeks ago and I think it’s going to be on my list of top nonfiction or memoir-type books of the year. I don’t know Melinda Gates personally, but you really get to know her from the book, which was another thing. It’s very hard for an author to do when they are going after a specific topic, and not have it just be an autobiography, and this certainly isn’t. You really get a sense of her as you read it, which is awesome.  

A charity that you’d urge people to get involved in and why, especially for the listeners in Seattle?

Rebecca: Absolutely. I am a huge fan of a program called Apprenti that was launched by the Washington Technology Industry Association. This directly addresses the talent shortage that we have in the tech sector and seeks equitably shared prosperity. This is an accelerated training program for career changers who are seeking living wages and meaningful careers in IT. And they primarily focus on barriered and underrepresented populations like women, like people of color, like justice-involved individuals, like veterans. A remarkable story. They’ve now served hundreds of graduates with life-changing training.

Brad: Last question. Guns N’ Roses themed: If you could have dinner with anyone dead or alive.

Rebecca: Hmm. So I was a history major in college and have long been an admirer of Eleanor Roosevelt, just in terms of her commitment to race and social justice and gender equity. But if I were hosting, I would make it a dinner party and I would have Eleanor Roosevelt, Marie Curie, Janelle Monáe, and Chrissy Teigen. I think that would be a delightful party. 

Brad: That’s a great group.

Thanks for the time today. And more importantly, thanks for all the awesome stuff you do for entrepreneurs and for everybody, both in Seattle and everywhere else.

David & Brad reflect on the first six episodes of the Give First podcast

How has the Give First podcast been going? David and Brad reflect on their initial forays into podcast hosting, and come to the conclusion that, while they’re still learning, their guests are amazing. 

With six full episodes of the Give First podcast under their belts, David Cohen and Brad Feld are of the opinion that they’ll probably need to do about 20-30 to truly hit their stride as podcast hosts. But they have nothing but praise for guests so far: Wendy Lea, Paul Berberian, Troy Henikoff, Mary Grove, T.A. McCann, and Kesha Cash.   

In this episode, David and Brad discuss what they learned from each guest, their favorite anecdotes or lessons, and how each one of these extraordinary people lives Give First in their own way. Plus David tells some more of his beloved dad jokes. 

They also offer useful advice for how to get the most out of working with an idea-a-minute person—like, for example, one of these cohosts.  

How do you think these newbie podcast hosts are doing so far? What do you think of this pause for reflection? Who would you like to hear as a guest on an upcoming episode? 

David and Brad would love to hear about what you love and what you don’t. You can email them your feedback on the Give First podcast at

Companies, people, and resources mentioned in this podcast:

Edited highlights from the conversation:

Wendy Lea talks about the risks of saying no

David: The first episode was the wonderful Miss Wendy Lee. What I remember from that show is Wendy talking about the risk of saying No. Right? You have all these opportunities and you think about the risk of saying Yes, but it’s sort of stuck with me that actually not doing something is a pretty big risk sometimes too.

Brad: I’ve known Wendy now for 20 years since I first met her when she had moved to Boulder; I think she had left she left Siebel systems by then. One of the things that’s amazing when you listen to Wendy talk is the level of humility she has with her journey, which is something else that I find really refreshing. She’s always still learning. And even when she was describing the anecdote about saying No, it almost sounded like she was relearning it again, which made me smile. I really liked it.

David: Yeah. It’s been a really fantastic to have her around Techstars, on the board for many years. And  I know I learned a lot from her too. So if you haven’t caught that episode, definitely would recommend you go check it out. 

Wendy’s seen so many different things in her career, right? She’s been in the big companies and little companies and I think her perspective is super interesting.

Brad: I think the geographic perspective is useful too because her range of experiences and where she’s really spent her time. A long tour of duty in Cincinnati with Cintrifuse and then prior to that, a bunch of time in the Bay Area. And so the ability to really get a view of entrepreneurship from multiple different startup communities is powerful. 

The other thing I’d say about the episode, since it was our first, is I’ve been reflecting as I listen to each episode. When we talked to Wendy, it was literally the very first time you and I had done a podcast together. We’ve both been on lots of podcasts, but being in the hosting shoes is a totally different thing. And as I listened to it I cringed some with our own performance and sort of our stiffness around it, and my sense that we probably have to do 20 or 30 episodes before we really hit our stride. And that’s a powerful thing to remember when you’re trying something new, even if you have had a lot of success and done a lot of different things in different contexts. And so approaching this whole podcast thing with beginner’s mind—I was reminded of that when I listened to the one we did with Wendy.

David: Exactly. I say the same thing, like the sixth one was better than the first one, but probably still not good. So we’re figuring it out. 

We do have an email address: People have been sending us feedback: do more like that or less like that. Stop telling dad jokes, Cohen, they say things like that. But you know, that’s how you learn. So hopefully we’ll keep improving it. And I agree it’s going to be 30, maybe 50, before we really get our rhythm. And I’m trying to learn from the best. Right? We’re taking some notes from Harry Stebbings and doing more research about the guests ahead of time and really getting more questions to ask them. 

We’d love more feedback at

Paul Berberian on the “addictive” nature of mentoring

David: In episode two, we had Paul Berberian, who we’ve both known for a long time, about how mentoring can really feel addictive, and what mentors and mentees really get out of it without even realizing it. And what stuck with me was hearing his stories about his dad—how his dad was an entrepreneur and he just sort of was always around that. And that resonated with me because that was the same way in my family.

Brad: Paul and I worked on the very first investment I made from the prior firm I was part of, which became called Mobius Venture Capital. It was a company called Raindance.  So we both got to work together at the beginning of our journey. We were both working together today on Paul’s company, Sphero, which is Techstars company. One of the things that’s been interesting about Paul and my own experience with them working together is it’s the epitome for me of peer mentorship.

I feel like over the years I’ve learned as much from Paul as I imagined that he’s learned from me. And I can’t actually say what he’s learned from me. He’d have to be the one that says what he’d learned. But he sort of brings that across well in the podcast. He’s still an entrepreneur who is learning a lot from other mentors around him. But at the same time he provides extraordinary mentorship back. And as you get to that place where you’ve worked together for a very long time, the mentor relationship changes and it’s not mentor, mentee, but it’s just pure mentorship where you’re both interacting with each other and learning from each other on this journey through life.

David: That journey, you never know where it’s going to take you. You know, I’m fortunate enough to work with Paul also, and I talked to him for an hour yesterday. He’s an idea-a-minute guy, right? He has lots of new ideas all the time. I know you have that. I have some of that affliction as well. 

T.A. McCann on how sailing in the America’s Cup is like running a startup

David: As we got to T.A. in a later episode, T.A. McCann talked a lot about how he deals with an idea a minute and his ITINDY system. That episode was really cool, talking about sailing and what he learned from sailing, and how that influenced his thinking about being an entrepreneur. It was just really fascinating to me.

Brad: T.A. and I ran the Madison Marathon together, I don’t know, four or five years ago. It was through the University of Wisconsin, Madison campus, and it was maybe a third or a half marathon. That was where T.A. trained—he’s a swimmer and trained for a bunch of time. And I think we spent most of the four and a half hours of the marathon talking. Talking about sailing, swimming, training, discipline—the dynamics around these big goals that you have far in the future, but all the ups and downs that it takes to get you there, including the successes and failures instantiated along the way as an entrepreneur and as an investor. 

My own experience with T.A. is watching him in this very, very long view, steady, deliberate step after step after step frame without being resistant to all of the different things that come at you, which really comes out when he talks about the experience with sailing, because who the hell knows what’s going to happen? Right? It’s just crazy minute to minute. And the parallel to entrepreneurship in a lot of ways is very, very similar.

David: If you didn’t get a chance to check that one out there’s some great stories about some famous people, including severed thumbs. Yeah, I wouldn’t miss it if I were you.  

You know, the thing that T.A. blogged about that he mentioned in the show, the ITINDY—he said, Greg Gottesman, who he works with at Pioneer Square Labs, is the idea-a-minute guy. I said, yeah, I’ve got one of those guys in my world. It might be my cohost. And he has this system: ITINDY. I had never heard of it, but it’s on T.A.’s blog and it’s Important Things I’m Not Doing Yet. Meaning I want to do it someday. Have you seen that system elsewhere, and how do you recommend people deal with so many ideas?

Brad: Well, I do know T.A.’s ITINDY thing. He had to deal with me also as his investor in a company called Gist, and I have the same affliction, which is a large number of ideas all the time about different things. I have my own approach to them. It’s different than “strong opinions, loosely held,” which I think is a terrible phrase. I wrote a blog post about this recently. It’s a very different problem when you have lots of ideas, because what you’re doing when you have lots of ideas that you’re giving other people data. If you’re not being discriminating about the data that you’re giving them, it’s up to them to some degree how to prioritize them. 

People who are really good at dealing with people like Greg or me, sort of on the receiving end of those ideas, know two things. One is that it’s up to them to prioritize, which means that there’s an awful lot of things they can toss by the wayside. The other is that the vast majority of the ideas aren’t good ones. They’re ideas. They’re not assertions, they’re not truths, they’re not facts, they’re just ideas. They need to figure out how to listen to the ideas from your partner, who’s an idea-a-minute partner, or your colleague or your investor or whomever, and process it. Not toss it all away, because then you’re going to miss some absolute total gems, but at the same time not stifle or try to control it. Because the idea-a-minute person—if you say, look, I can only get one idea from you today, so I’ll pick the best idea. That doesn’t work either because then the idea-a-minute person just shuts down, and he goes and find some other place for his ideas. So I think T.A.’s approach is a really good one and it’s a good example of self management.

David: I find a lot of times that with you and our relationship, most of the ideas actually are really good. It’s just impossible to keep up with all of them. And a lot of times what happens by just capturing them and thinking about them is that you end up with a higher level concept: some idea that’s an amalgamation of all the other things.  And that those can be really powerful because you’re kind of getting at the intersection of lots of great ideas.

Brad: I think that’s well said. 

Something T.A. said to me at the very beginning of our relationship. I can’t remember if it was in the first couple of months after I made the investment, but he said something akin to: Hey Brad, I appreciate all this product feedback you’re giving me. He has a wonderful story about how we still hadn’t invested but it was just before Christmas and he had just turned me on to the latest build of Gist. And on Christmas Day I sent him like 15 emails with products, feedback. And I think it still amuses to this day. I explained to him that as an oppressed Jewish kid who never had Christmas, what I prefer to do is play with software on Christmas day when everybody else is opening presents, because that’s a really joyful thing for me to do.

And he asked me, he said: You’re giving me all this product feedback. What do you expect me to do with it? Do you want me to prioritize it? Is it important to you? How do you think about it? And I said, I’m just giving it to you. It’s stuff I see. It’s up to you to do whatever you want with it, and you’re the CEO. I trust you as a CEO to do whatever you want with it. If you don’t want me to send it to you, or you want me to send it to somebody else because it’s distracting you, just tell me where to send it. Do you want me to put in a database? I’ll put in a database. If you want me to not do it anymore, I’ll go play with somebody else’s software.

It’s that kind of approach. I think that reflects more on T.A. than on me. Early in the relationship, he came at me and said, Help me define how you want this to work so that I, T.A., understand what your, Brad’s, goals are, so that I, T.A., CEO, can then be more effective dealing with your goals. It didn’t put him in a one up or one down relationship with me, but it took control of the interaction so that he could get the best use and the best information from it.

David: Love it. Sounds familiar on some level. 

Mary Grove on the origins of Google for Startups & Startup Weekend

David: In episode four, Brad, you spent a bunch of time with Mary Grove. You’ve spent a bunch of time in your career with Mary as well. She’s now at the Rise of the Rest fund.  We talked about the power of entrepreneurship globally, growing that through Google for Entrepreneurs. I know you’ve had a really long experience with her. I’ve worked with her more recently on the Techstars Foundation and found her to be hugely additive. What were your biggest takeaways from talking to Mary?

Brad: Well, for those people out there that are fans of Startup Communities and follow the work that I’ve done with the book and subsequently the work that Techstars has done, both with startup communities and around ecosystem development, there are probably 30 or 40 people that have really influenced my thinking over the last decade on this. And Mary is near the top of the list. It’s not from huge amounts of time spent together going deep intellectually on things, but rather from observing what she has done and how she has done it, specifically in Google and around Google for Entrepreneurs. I’ve talked for a long time over the last six or seven years to people about how large corporations, tech and otherwise, can be helpful in the context of startup communities. And in 2012 when I wrote Startup Communities, I had some ideas about it that I’d say were early.

I think Techstars—through all the work that David, you’ve done, that David Brown’s done, that the leadership team of Techstars has done in all the various accelerators that we’ve done with different corporate partners—has really advanced that thinking for me. But I often go back to thinking about Mary and the context of what she did with Google for Entrepreneurs. And when I’m trying to explain to someone in a large corporation how to think about their company—overlapping with entrepreneurs and how they can be helpful and supportive and entrepreneurs-centric, but entrepreneurs-centric against the backdrop of their large organization’s goals—I often use examples that come out of things that I either observed, saw, or experienced that Mary had done and Mary and her team had done at Google for Entrepreneurs.

David: In listening to that show, one thing I remember being struck by is the gratefulness that she was trying to express. And I always think, Wow, I’m just so happy that we’ve been able to work with you and learn from you. That’s the power of this whole Give First thing, right? Maybe everybody feels like they’re doing that, but they’re getting so much more in that virtuous cycle. So I really felt that from that particular episode.

Brad: My partners at Foundry a have a specific line that we like to use when we’re talking about people, which is that we always want to work with good people. For us, “good people” is the price of admission. We like to think we’re good people, and when we don’t behave as good people, we are open to the feedback around it. But we’re really trying to work with other good people, and really we’re trying to work with awesome people.

One of the attributes of awesome people in our frame of reference is that they’re appreciative of the experiences that they get. Use me as an example. Right? I’m super appreciative of all the people I get to spend time with and work with on all the things I get to do. And yeah, sure, sometimes I have a bad day or I’m in a bad mood or I’m grumpy or I don’t behave well or I fail at something and I’m frustrated with myself or other people. But this idea of always trying to be an awesome person and surround yourself with awesome people. It comes back to the thing I said at the very beginning.  I think about Wendy: just this notion of humility, this appreciation of our time on this planet, and that we get to work with each other on these super interesting things.

David: Techstars calls it awesome people collection mode. I don’t know where we got it. If you run into an awesome person, you can collect them and get them on the team, get them in your portfolio, then you just have more awesome people that you’re around. And I agree that that feeling of thankfulness, gratefulness that you get back from them is one of the attributes that they seem to have.

When I look at the first six guests, we’ve done pretty well. We have three women that we’ve had on the show and we’ve had three men. I think that’s somewhat intentional but good balance. 

Kesha Cash on impact investing—and how mentorship got her there

David: One of those guests in episode six was Kesha Cash.  We talked with her about mentorship and the opportunity to learn from her mentors that allowed her to get into investing. She talked about the particular mentor that, much like Paul Berberian talked about Jack Tankersley, she said this person really opened the door for her to become an investor. And of course that’s had downstream impact on diversity and inclusion in the world because Kesha is now investing in so many people and creating so many opportunities herself. So that was a fun one that I enjoyed. And of course I know you’ve done a lot Brad, as well, to promote diversity and inclusion, and I think this is something that is worth a lot. 

Brad: I think in addition to the notion of promoting diversity and inclusion, I think it links directly into the idea of mentorship, and this notion that anybody who is experienced should try as part of their energy to be as inclusive as they can of other people who are trying to get into the industry that they’ve got experience in. That applies to venture capital, applies to entrepreneurship, applies to a bunch of different things. And I think that one of the central tenants of Startup Communities is this idea of being inclusive of anyone who wants to engage in any level. But more importantly, as a mentor, it’s been very powerful and very satisfying to me, both emotionally but also intellectually, in terms of my own learning feedback loop, to mentor some younger women who are trying to get into the venture community or are early as venture capitalists.

We’ve been very supportive of All Raise since they started, both functionally and financially. And one of the things that I’ve gotten to do as part of that is every, I think it’s every quarter, I get assigned by All Raise a female VC. All different experiences. They do a good job of matching them up with domains where I can be helpful from a domain perspective. And in that mentoring activity, it’s not that I’m talking to the person or trying to teach them anything or just being a network connector for them.  But it’s a committed, engaged relationship where we spend time talking about specific things that they’re struggling with, that that particular VC is struggling with, in a confidential environment. I just had one of these calls the other day, so it’s fresh in my mind. 

It reminds me of the importance of two things as a mentor. One is to listen well to the person to understand their context and their reality, because it may be very different than my own context and reality. And then the flip side is that as I engaged in this particular conversation, as I engaged in the feedback, I actually learned a bunch from the person who I was mentoring, based on some dynamics that she was encountering that didn’t ever occur to me as a middle aged white guy. So again, this idea of this feedback loop where as a mentor you can learn a lot from the mentee, especially when you open your aperture to be more inclusive of other types of people versus just people that you know, or that find you, or that you find randomly.

David: So what point, Brad, do you think we go from middle aged white guy to kind of old white guy? I mean is there a moment when that becomes very real for us?

Brad: I’m starting to feel like I’m in that shift.

David: It’s like all the injuries you get every day. Yeah.

Brad: Please don’t tell my parents, because I don’t think my mom wants to think of me as old yet.

David: Yeah. Well, but there is a moment. For me, I have this Achilles pull. Like every time I go to play tennis I’m limping around, you know, injuring myself somehow. So I’m getting there, I think.

Brad: I think that has less to do with the age spectrum and more to do with just being whiny.

David: Is that what it is? So I could work on that then. I can’t work on the age, but I can work on the whiny.

Brad: Stretch more. The age will advance a day at a time. Just stretch more.

David: Even the day is a completely artificial construct, as you know.  

Troy Henikoff on how #GiveFirst grew the Chicago startup ecosystem

David: You talk about learning from the interactions with female VCs or people dealing with different problems. I learned from Troy Henikoff, with whom we did episode three. Troy tells this amazing story—much better than I will here—in episode three about how he got so much back from an entrepreneur who viewed him as being helpful, but who he saw as being way, way more helpful to him in his career. And that articulation of it was really amazing for me, because it was about Alex White and Next Big Sound, which was a company we funded, and how Troy’s perception was that Alex had completely changed the trajectory of his life, and Alex sort of felt the same way. 

So bringing this whole thing full circle, this is the Give First podcast, right? And I think that key message that we’re really trying to get through and bring out in these stories is that by giving first there’s this cycle, it just escalates and comes back in totally unexpected ways. And I thought Troy did a great job of capturing that story with Next Big Sound.

Brad: I think Troy, he also has a couple of other good stories, one in the podcast about other people where he didn’t have an economic relationship but he’s still got back massive value that he didn’t expect. And I think this is something that comes up all the time. I think we struggle or people struggle sometimes with, well, how much energy should I put into something if I don’t know what the economically defined outcome is going to be on the front end? And there is often magic that happens when you’re willing to—across multiple people, across multiple different contexts, and over time—put your own energy into things, but without having to find that transactional construct upfront. Right? That’s the essence of Give First. 

Troy’s a great example of it, and very articulate about how that has played out in his own life.  And then he translates it into lots of 1:1 behavior, which I’ve seen and experienced and been involved in plenty of. But in some ways, even more interesting, 1:many behavior. Troy has worked very, very hard at doing content that’s unique in very bite sized chunks. If you’re an entrepreneur and you’re looking for various quick hit things—fundraising or pitching or positioning your company—Troy’s done a really amazing job, for the only reason that he experienced a ton of this and learned a ton of it from all of his experiences as Techstars MD in Chicago, and then just wanted to translate it more broadly to a bunch of people.

David: He’s still so plugged in to Techstars. He’s running MATH, but he’s still showing up, and being a top mentor, and you end up seeing him everywhere you go and he very connected to the system. So it’s a great relationship that just continues to develop over time, as the best ones do.

Brad: So, David, from the way we’ve been talking, it would seem like we actually like these people a lot.

David: You would think. I mean, we’re probably good actors.

Brad: I mean, are you just being effusive about your adulation for these people?

David: I mean, that’s why we have them on the show. We’re not going to have people on the show that we think suck, right? We’re going to have people on the show who we think you can learn from, who do amazing things but, but who represent a cross section of different points of view. 

So that is the show for today. Let us know if you like this format or not. We would love to hear: do you like this sort of banter about the past episodes or would you rather hear Brad and I tell dad jokes? Let us know your preferences.  Let us know if you have thoughts a guest who should be on the show. And you know, we’ll keep doing it until we find out nobody’s listening. That’s the plan.

T.A. McCann on how sailing in the America’s Cup is like running a startup

T.A. McCann, serial entrepreneur and Managing Director of Pioneer Square Labs, has sailed in two America’s Cups. How are sailing and startups alike? T.A. explains.

David Cohen was super excited when he realized that T.A. McCann—founder and CEO of Senosis (acquired by Google), Gist (acquired by Blackberry) and Rival IQ, a leader in marketing analytics, as well as Managing Director of Pioneer Square Labs—was the same guy he was reading about in The Proving Ground: The Inside Story of the 1998 Sydney to Hobart Race.

T.A. tells tales of his sailing adventures—including one harrowing anecdote involving Rupert Murdoch’s finger—and applies the knowledge he gained competing in two America’s Cups to running and growing startups.

Companies and resources mentioned in this podcast:


Pioneer Square Labs (PSL)

The Proving Ground, by G. Bruce Knecht

Rival IQ


Edited highlights from the conversation:

Sailing as a metaphor for startups:

David: If you haven’t read the book, go get Proven Ground. It’s really great. And it’s so cool that you’re in it and it’s all real. That’s really an amazing, true story, which I love better than fiction.

Any tiny little advantage is really important in sailing. Deciding what’s the risk of doing something or what’s the risk of not doing something is so important. We had Wendy Lea on recently and she was talking a lot about the risk of not doing something. When you’re coaching startups, how do you assess risk-reward in your coaching them, knowing that small things can make big differences over time?

T.A.: I’ll play with a sailing analogy a little bit. Because it does answer your question. So in the America’s Cup and the highest end of sailing, you have a very significant amount of money. Think of it like a Seed Round or a Series A. You have a hypothesis about different areas on which you can experiment that might create an advantage. And in the sailing category, that could be boat design, sail design, team design, tactics, electronics, weather, etc. Even in boat construction, you hire the best people you can. For each one of those subdisciplines you build a big gigantic Gantt chart of which experiments will take how much time. What do we expect to see? How might we test A versus B? And you start running those processes, those tests.

The difficulty at a management level is knowing how many different tests or how many swim lanes you can run, how many different experiments you need to do in order to make a decision. Is this category going to be an area of innovation? Or is it just going to be an also ran? Should I double the amount of investment in category X versus category Y?

I’ll give you an example. In 1992, we had a hypothesis that we could invent an entirely new type of sail cloth made of carbon fiber, which is a very brittle material, very light, very strong. And we went through many, many iterations where the first sail we would put up—$10,000-$15,000 worth of sail—would literally blow up in like five seconds. That didn’t work.

Keep trying, keep trying, keep trying. Ultimately create this product called Cuben Fiber that was about 20% stronger and significantly lighter than everybody else’s. One small innovation that led to a significant advantage. That was some part of us winning that 1992 America’s Cup, and in the startup mode.

I think the advice I pull out of that story is really thinking about the areas where your individual team has a hypothesis for an area of innovation. What are you going to do the same way that everybody else does? A different way? How might you design that experiment? How can you delegate the ownership of experiments to different people on the team? In a CEO or founder kind of role, your job is to think about whether you have enough capital applied to the two, three, four, eight areas of innovation that you might create an advantage around, and then managing that through some realistic timeline and decision making on which ones are going to work, which ones are not going to work, and which we’re going to invest more in—which actually has some validity around what we do at PSL as well.

David: For sure. Hey, last sailing analogy, I promise. You know, when you’re a little bit behind, your approach to risk is different. So let’s say you have a competitor that’s outflanking you. Maybe in sailing you’re going left or going right and you’re trying to figure out how to look for advantage. Have you found yourself encouraging people that you work with—CEOs, mentees—to react differently because the competition’s ahead or just stay the course and know that you can bear up?

T.A.: I built and you invested in a whole company called Rival IQ that is partially about this. If you can understand your competitors well—in the case of Rival IQ, it’s specifically around digital marketing—if you can understand your competitors well, you first choice is, can I compete or not? Right? Do I have the appropriate intellect or resources to compete? If the answer is no, you have to find a way to create a different area that they’re not spending time on.

So I think the answer for startups is to first understand your competition. If you use a sailing analogy like the 1995 America’s Cup, we were outspent three to one or so. The team that we were sailing against had boat speed on us, and so what we had to try and do, which ultimately we still failed and lost, but we had to be much, much more aggressive on tactics. We were almost always trying to create an area where they would create a foul on us, at which point we may have a chance of winning because we were just slow enough that if we could get one foul on than we might be able to make it even.

David: Fascinating. I love the way you’re thinking about that—understanding the competition versus overreacting to them, right? And being intellectually honest with whether or not you think you can bear up.

T.A.: The other part, as regards to both sailing and startups, is really thinking about fundraising. So fundraising is a strategic advantage. If I can raise more capital than you, even if I spend it slightly less well, I may still be able to create an advantage. If I get the best capital, the best investors for space A or space B, it’s much less likely for you to be able to get those kinds of people. I think about fundraising as a strategic weapon that you can utilize in your startups. And therefore, I highly encourage people to think when you’re going into fundraising mode about who is the best possible investor that you need. Do you understand the competitive landscape of the best investors? What have they already invested in, and how can you fit into that jigsaw puzzle?

That’s the same as we would have done from a sailing perspective: understand the competition. Understand how you fit into that competition.

Aligning creativity with process:

T.A.: I’m a mechanical engineer, so I like thinking about the way things work as much as what they do. And this is true about startups, too. Part of the reason I’m such a fan of Techstars and Startup Weekend and even all of us who are working on studios is there’s a whole bunch of process oriented stuff, whether it be fundraising or product development or recruiting, etc. that can be generalized or certainly got to a place that is sort of best practice level, and that can be applied to many different kinds of companies. Part of the reason I was excited about joining PSL was that they had had success, but in many ways weren’t quite sure why.

It’s like companies that have early product market fit, and you’re like, oh my gosh, it’s going great. But I don’t know exactly why. And if you don’t know exactly why, you can’t predict if it’s going to continue in the future. So part of the reason I joined PSL and was excited about it is they had great success, a limited amount of process, and I’d say a limited amount of understanding or repeatability or certainly predictability in that. So I kinda came in and I started trying to figure out for myself how this place works. What has worked well, what has not worked well? Why is this company being successful, and this other company less successful? I tried, both for myself and for PSL, to start to document that, write it down, draw a schematic, draw a flow chart, that type of thing.

In addition, we were not very consistent at talking to new founders or new entrepreneurs or new potential CEOs about how the process works. So sometimes process drives consistency, and as we add more MDs, more people, more companies, we also had to figure out how to communicate this consistently. And if we can communicate it consistently, can we start to predict how likely a company is to be successful? Meaning, can we get it out and can we get it funded and can it get good early market traction?

Greg [Gottesman, Co-founder of PSL] is so creative. He’s an idea-a-minute kind of a person. And yet that idea-a-minute can be very distracting for a company. You might have the shiny penny kind of CEO: sometimes they’re like, oh we could do this, we could do this, we could do this, we can do this, we could do this. But as you start to get scale in a company, even small scale, five, 10, 15, 20 people, that’s very jarring for a company, because they can’t keep up with all of that. You don’t know when or how each idea should be factored in with all the other things you want to do.

So it’s amazing to have creative people like Greg, and it’s amazing, especially in our world here at PSL, to have lots and lots of ideas. The trick is balancing that with: How do we take an idea and move it into validation? How do we know how to move it out of validation into creation? How do we know when to get a CEO for that? How do we know when to spin it out and how to fund it, which are kind of the main parts of our process? And so we have tension between creativity, lots and lots of new ideas, and productivity or structure by which to evaluate those ideas, know which ones to try, which ones to explore and and which ones to just put on the back burner. Or what I would call The Important Things I’m Not Doing Yet list—or ITINDY.

Rapid Fire Round

David: Favorite city that you think everybody in the world should visit.

T.A.: Outside Seattle, it would be Auckland.

David: Any favorite charity that you urge people to check out or get involved with in some way?

T.A.: I’m on the board of We provide clean water to the poorest communities in the world, and it’s a really cool company that is a nonprofit that functions very much like a for profit. Incredibly cool.

David: Awesome. We’ll check it out. Hopefully we’ll get some Give First action going there. If you could have dinner with anyone, dead or living, who would it be?

T.A.: Elvis Costello.

David: Oh, fun. Why’s that? Got to ask.

T.A.: I’m just a huge fan. He’s so creative. Smart in many, many different ways. He’s been a musician in lots of different ways and also an advocate. So a life hero and interesting person and obviously very creative.

David: We’ll end with this. How can somebody listening today give back to you and maybe to PSL for the great advice they’ve heard here today?

T.A.: I write a blog at and there’s a lot of startup stuff on there. So give me feedback on this stuff that I’ve written, and share the things that matter to you. And tell me things that you hope that I would write about in the future.

Mary Grove on the origins of Google for Startups & Startup Weekend

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

Larry Page

Mark Nager

Megan Smith

Sergey Brin

Silicon North Stars

Startup Grind

Techstars Farm to Fork Accelerator

Techstars Foundation

Techstars Startup Weekend

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 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.

Troy Henikoff on how #GiveFirst grew the Chicago startup ecosystem

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.

Paul Berberian on the “addictive” nature of mentoring

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:

The Twenty Minute VC, hosted by Harry Stebbings

Centennial Ventures

Community Foundation


Power Moves by Adam Grant

Raindance Communications – acquired by West Corporation


Star Wars: The Force Awakens

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.

#GiveFirst In Action

#GiveFirst is a Techstars mantra.

Simply put, it means giving—advice, resources, assistance, etc.—with no expectation of getting anything specific back. When a network of people, such as a global community of entrepreneurs, live in a #GiveFirst way, each is helpful whenever they can be. This builds a powerful network of caring people, all flourishing because they are all giving to each other. A #GiveFirst perspective asks, “What small thing can I do to help this person?” rather than, “What can this person do for me if I help them?”

This may all sound very abstract and idealistic, but #GiveFirst is unmistakable when you see it in action. And it works.

The Most Meaningful #GiveFirst Experiences

For Michael Maylahn, founder and president of Stasis Labs, “The most meaningful #GiveFirst experiences I’ve had have been when I’ve been the one giving.”

Michael and his co-founder Dinesh Seemakurty went through the Cedars-Sinai Accelerator, Powered by Techstars in 2016, and have since mentored “tons and tons” of founders through the Techstars network—despite being well under 30.

That’s one mentor myth laid to rest: mentors do not have to be older than you. What they do have, regardless of age, are experiences that pertain to your problems, and a willingness to share their time and expertise.

Michael recalled one such experience, when a member of an accelerator class was paired with him, an alumnus. Her startup was setting up a pilot with a major healthcare network, and everything looked lovely. Then a large incumbent announced a new module that filled the same function as her product. Literally overnight, her business opportunity disappeared.

“For her, having someone to talk about it with was great,” Michael said. “Selfishly, it was also great for me. I got to peek under the covers and see how it was going down: not as an investor, employee, or customer, but just as another founder who wanted to help.” He got to be involved in the process of a 180-degree pivot and is glad to report that the company is doing really well.

This unique perspective that Michael got was hugely helpful to him. He had the chance to see how another terrific founder handled this brutal situation, and learn from it himself, with much less pain.

Mentoring hasn’t just given Michael ringside seats to difficult entrepreneurial situations. It’s also taught him the value of teaching. “In order to mentor well, I’ve had to solidify my viewpoints on fundraising, product management, hiring, marketing, and more,” he explained. “When you have to break it down and explain it to someone else, you end up understanding it better yourself.”

“In many ways, the more I’ve mentored, the more I’ve realized how mutually beneficial it really is,” Michael said.

“I Wouldn’t Be Where I’m At”

While today Michael is enjoying the benefits of mentoring, he’s had a long history of being on the receiving end of #GiveFirst. “I wouldn’t be where I’m at if hundreds of people hadn’t lined up to give their time and teach me how to run a company,” Michael said, with great certainty.

Michael and Dinesh are engineers. They started Stasis Labs as college students, and even before Techstars they were receiving the benefits of #GiveFirst: “I would talk with anyone who would give me 30 minutes,” Michael said.

To illustrate his younger self’s cluelessness, Michael remembered an excruciating exchange, when a well known investor asked him what the ROI for his customer was, and Michael had to respond with, “What’s an ROI?” He literally didn’t know what the acronym meant, let alone how to answer the question.

It is the hundreds of people who helped him that Michael is honoring every time he answers a basic—or not so basic—question from an entrepreneur. But he’s quite clear that he doesn’t see it as a transaction. He’s not mentoring because he’s in their debt. He Gives First because he sees the power of a network built on this principle, and because it’s the kind of person he wants to be.

Michael is grateful to Techstars for so much—for the chance to understand the opportunity for the product in the U.S. market, for help from all the Techstars mentors, for the enormous access with medical executives, directors, and VPs, all of whom gave him invaluable feedback on Stasis—and also for #GiveFirst.

“Techstars has given me a medium to #GiveFirst to others and for others to #GiveFirst to us,” Michael said. He’s going to keep Giving First, because it’s right, and because he learns so much from doing so. And he knows that when he needs help, the Techstars worldwide network is there for him, and ready to #GiveFirst.

Wendy Lea talks about the risks of saying no

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.

Subscribe to the Give First podcast now.

Companies and resources mentioned in this podcast:

EventVue – closed

First Round Capital


Get Satisfaction – acquired by Sprinklr

OnTarget – acquired by Siebel Systems

Pipeline Equity

Siebel Systems – acquired by Oracle

Small Fry, by Lisa Brennan-Jobs


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.

Why Make A Give First Podcast?

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!

Techstars Give First Awards 2016

This fall, at our FounderCon conference in Cincinnati, we began a new tradition called the Give First awards. We decided we wanted to recognize founders and mentors from our global network who consistently live this core value of Techstars.


The idea behind #givefirst is that we try to be helpful without any specific expectation of return and in a non-transactional way. In short, if we can be helpful, then we want to be helpful.

Here are the founders and mentors who we recognized this year for how they live this value.

David Mandell is the co-founder and CEO of PivotDesk (Boulder ‘12) and a Techstars mentor. David shows up and helps at so many Techstars locations. He’s mentored at Patriot Boot Camp (a non-profit we funded early on and helped launch). He shows up at Techstars accelerator programs around the world and meets with companies because he loves being helpful. I suspect that he’s mentored in more locations than any other Techstars mentor. He’s consistently rated as a top mentor at these programs he visits.

John Guydon is the founder and CEO of the Lassy Project (Boulder ‘14). I love working with John because of his “straight talk.” He’s not afraid to tell us how we’re screwing up or how we could do something better on behalf of everyone in the network. At the same time, he’s incredibly generous with his time and a great representative of our alumni.

Rami Essaid is co-founder of Distil Networks (Cloud ‘12) which has grown into a very valuable company. However, just because Rami is the CEO of Distil, he hasn’t forgotten his roots and he is constantly giving back to Techstars by mentoring, hosting alumni gatherings, sponsoring FounderCon, and more.

Thanks to everyone in the network for all that you do. Learn more about Give First in this video.