Philip McKernan believes life is too short to have regrets. As a life coach, he is dedicated to helping others rediscover themselves, tap into their greatest gifts and create a positive impact on the world.
Philip McKernan talks with David Cohen about how to find your purpose in life and his work with entrepreneurs. Through his coaching, he encourages people to take the risk they would only take if they were dying tomorrow.
Listen as Philip and David discuss the importance of reinventing yourself, finding a business that fulfills you on a personal level, and how the idea of “holding space” can transform an entrepreneur’s home life.
You can find the resources mentioned by Philip here.
What would your one last talk be about? Tell David on Twitter @davidcohen.
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 email@example.com.
Companies, people, and resources mentioned in this podcast:
- All Raise
- Paul Berberian
- David Brown
- Kesha Cash
- Foundry Group
- Gist.com (sold to Blackberry)
- Google for Entrepreneurs – became Google for Startups
- Greg Gottesman
- Mary Grove
- Troy Henikoff
- Wendy Lea
- T.A. McCann
- MATH Venture Partners
- Mobius Venture Capital
- Next Big Sound
- Pioneer Square Labs
- Raindance Communications – acquired by West Corporation
- Rise of the Rest
- Startup Communities: Building an Entrepreneurial Ecosystem in Your City, by Brad Feld
- Harry Stebbings
- Bad Entrepreneurial Cliches: Strong Opinions Loosely Held
- Jack Tankersley
- Alex White
Edited highlights from the conversation:
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: firstname.lastname@example.org. 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 email@example.com.
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.
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.
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.
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.
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.
Strong mentorship was essential to Kesha Cash’s journey to becoming an impact investor. Her mentors Gave First to help her—and now she’s Giving First to diverse entrepreneurs through her Impact America Fund.
Kesha Cash founded Impact America Fund in 2013 with a goal of investing in software and tech enabled companies that have a positive benefit on underserved communities in America. In 2018, she was named one of Fast Company’s 100 Most Creative People in Business.
She went to Columbia Business School knowing that she wanted to start a fund that invested in diverse entrepreneurs, and it was there that she met Josh Mailman, founder of Serious Change, who became her mentor.
As an impact investor, Kesha Gives First every day. But she got to where she is today because of others, especially Josh, Giving First to her—empowering her, teaching her, mentoring her, and ultimately encouraging her to go out and start her own fund.
Companies and resources mentioned in this podcast:
Serious Change LP
The Wisdom of Finance: Discovering Humanity in the World of Risk and Return, by Mihir A. Desai
Edited highlights from the conversation:
The best mentor relationships become two way
Kesha: I had the opportunity to meet Josh Mailman [founder of Serious Change] at Columbia Business School. His family endowed the Mailman School of Public Health at Columbia and I started to work with him during my last semester at Columbia Business School.
This was, gosh, this was in 2010. I’d never met an angel investor that was interested in mission driven companies. I met Josh and Josh was a 60 year old at the time, you know, and a Jewish white man. We had this meeting and he expressed a sincere interest in moving more dollars into mission driven entrepreneurs of color based in the U.S., so we connected in many ways around that mission and I started to work with him. I volunteered during my last semester to identify companies that would fit the thesis of Serious Change. More specifically we were looking for entrepreneurs of color, and we made a number of investments together. What started out as a semester of volunteering ended up being a three year initiative within Serious Change to identify more of these companies.
Rod [Robinson, founder of ConnXus] was one of the investments that Josh and I made together. ConnXus was one of the investments that turned on the light bulb for me in regards to this thesis of there are tech solutions out there that can address inequities within systems. In the case of ConnXus, really looking at diversity and small businesses and the relationship with supply chains at large corporations is obviously very exciting. That early investment in Rod at ConnXus and a few other entrepreneurs that were using technology solutions became the thesis for Impact America Fund One. I was thankful for the continuous support by Josh Mailman and Serious Change. So that family office created space for me to learn, to grow my network, and to refine my thesis for Impact America Fund.
David: It sounds a bit like Josh was somewhat of a mentor, but like the best mentor relationships, they become two way, and I’m going to guess he’s learned a lot from you over the years as well.
The godfather of impact investing
David: Rod said it’s super clear to him that Josh, who he viewed as a pioneer of impact investing, has probably passed on a lot of knowledge and expertise to you. Talk about a little bit about that relationship that you have with Josh and maybe some things that you’ve learned from him or that he’s learned from you over the years.
Kesha: I call Josh the godfather of impact investing. He’s been at this for a very long time, before the term was sexy. We’re certainly happy that it’s a mainstream term now, but Josh and friends started this work over 30 years ago. He’s one of the cofounders of the Social Venture Network, of Investors’ Circles. It was really Josh and his colleagues, including folks like Ben and Jerry’s back in the day, saying, hey, there’s a better way to build businesses. There are ways for us to move our money that are good for society. I’m really blessed that I had the opportunity to meet Josh and work directly with someone. I learned from the godfather of impact investing about building this ecosystem and being catalytic.
Before I met Josh, I met people that knew Josh. They’re like, Josh is this radical, you know, in the best of ways. As an angel investor, he’ll sit down with someone, he’ll hear their idea and write them a check.
What I learned about Josh is that there’s a lot of thought process in writing that check. He’s really good at tapping into someone’s intentions. And we don’t always get it right, but I would say Josh has a gift for understanding the intentionality around a founder’s mission or business idea. What I’ve learned through him is that while that intentionality is extremely important in traditional business, I would say it’s even more so in impact investing. Understanding the founder’s intentionality and their reasoning for wanting to wake up every day to do this is truly important. That’s one of the many things that Josh taught me.
He’d ask me after meetings: do you think this person’s a good person? Which is a loaded statement for him because there are nuances as to what we mean by a quote unquote good person. He’s just good with people and understanding human nature.
He’s also extremely good at networking. He knows everyone across different industries. He taught me the importance of showing up at an event. Don’t talk to people you already know—you’re here to network and to do that in different spaces. When we worked in New York, we’d take trips to Harlem to visit an entrepreneur or go downtown, and it was just amazing to watch him be able to adapt to different environments and to really be present in those environments to understand what was happening from a cultural standpoint. I learned a lot from Josh about people and being present and truly understanding the atmosphere that we were in.
As for what he learned from me, you’d have to ask him about that. But he continues to be a great friend and mentor and I’m very honored to have him in my life as a mentor and as a guide through this process.
Go out and do it on your own
David: It sounded like Josh was a big proponent or fan of you launching off on your own with your next fund and activity that you’re doing now. Why would he support that? It sounded like he was a big fan of: Go out and do it on your own.
Kesha: That’s a great question. We met in 2010. After Wall Street and prior to Columbia Business School, I worked with very small lifestyle types of businesses in Los Angeles. The majority of those companies were led by entrepreneurs of color. That’s where I discovered this amazing talent that was disconnected from resources, and I applied to Columbia Business School with this idea of supporting and helping to build this ecosystem and getting more resources to diverse entrepreneurs. Right.
When I met Josh, I told him that I applied to business school with this idea. My business school essay said I wanted to raise $3 million to invest in these early stage companies. So when I met Josh, he’s like, Look, you know, you don’t have a track record. It’s gonna be really difficult for you to actually raise a fund. At this point, work with me. I have the capital, we can do deals. You go and find those deals, we’ll build it and they’ll come. The good thing about Josh Mailman is that he takes action. He’s catalytic, he takes action, he’s spent years trying to figure this out with me.
So we met and he understood my purpose and intentionality and we got to work. What started out as a, hey, come work with me for a year to identify some investments to do some deals, turned into a three year partnership at Serious Change. We got to the point where I said, Hey, I think I’m ready to create this independent fund, and he and Serious Change supported that. From our initial meeting, there was the intent that I would at some point spin off and raise an independent fund. And he held true to our handshake agreement. I’m thankful for that.
David: I mean, that’s a classic example of Give First. Knowing that he was going to train you up and then lose you—but that in another way he would get back from it because you would be carrying some of that business philosophy out into the world. Maybe even improving it a little bit.
The bottom line for impact investing
David: Any time I talk to someone who identifies as an impact investor, I like to throw out some data that we have here at Techstars, and you’ll probably identify with this.
We now have the Techstars Impact Accelerator down in Texas. We work with the Nature Conservancy. We have a farm to fork program. So we are doing more and more in quote unquote the space. As we did that, we really looked at the definitions of what we are looking for in those programs and found that 15% to 20% of what we’ve been doing all along falls pretty cleanly into this category of impact. And we pulled that cohort out. We’re investors in about 2,000 companies. So we’re talking a couple of hundred companies, maybe 200-300 companies that would meet this impact definition. And as a cohort they were performing better than the total cohort of all companies. So impact is not just about that second bottom line. It’s also about that first bottom line. And I’m sure you would agree.
Kesha: That’s true.
Rapid Fire Round
David: What’s your favorite city everybody should visit?
Kesha: New York City
David: Awesome. That’s a popular one. I think everybody wants to go there if they haven’t been there. I know why.
Kesha: I’m taking a red eye there tonight, so it’s top of mind.
David: You’ll be nice and rested tomorrow, I’m sure. How about a great book that you’ve read recently that you want people to know about?
Kesha: Oh, I’m almost finished with it. It’s called The Wisdom of Finance.
David: Any charities that you’d urge people to get involved with or take a look at?
Kesha: The Sponsors for Educational Opportunity. I participated in this organization while in college and was placed in my Wall Street position, and I think they are single handedly responsible for diversifying Wall Street. I encourage everyone to support them.
David: That’s awesome. As a thank you for being on the show, we’re going to do a donation to them, and also do one to the Techstars Foundation, which is focused on diversity and inclusion in tech, in your name, if that’s okay.
Kesha: Oh, excellent. Thank you. That’s wonderful.
David: We appreciate you coming on the show. Last one. If you have, if you could have dinner with anyone, they don’t have to be alive, who would it be?
David: It’s more fun if they’re alive. But let’s imagine that you could do it at any point in history is what I mean by that.
Kesha: Given the times that we’re in right now, I want to go back and be part of the conversations with some of our great civil rights leaders. Malcolm, Martin, some of the philosophers, I’m kind of going back a little further. W.E.B. Dubois. I think we’re in cycles. You can obviously read the books, but to be able to sit down and understand the philosophy and the lessons learned from different eras in time, I think would be extremely helpful right now.
David: That’s a whole party. I’ll give it to you. We’re looking for one person, but you can have a party. That’s cool.
Kesha, thanks so much for taking the time to join us on Give First. Best of luck with Impact America. Really appreciate you joining us today.
Kesha: Thank you, David, for all that you do as well.
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
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 splash.org. 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 tamccann.com 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.
Over the years, a #GiveFirst network will reward its members time and time again. Troy Henikoff looks back at 2009, when he first encountered Techstars and was so inspired he started his own accelerator—with some help from the Techstars Network. A decade later, that accelerator is now Techstars Chicago, and Troy is Managing Director of MATH Ventures. You never know where #GiveFirst will take you—but you do know you’ll never have to go it alone.
How does a startup ecosystem grow? #GiveFirst is one essential element.
Troy Henikoff, Managing Director of MATH Ventures and Co-founder of Excelerate Labs, which became Techstars Chicago, remembers the early days of Chicago’s startup ecosystem, and how #GiveFirst helped it grow.
One of the difficult things about describing the impact of #GiveFirst is that, over time, there are so many effects. Troy spends time in this episode telling stories about how giving and mentoring have changed his life and the lives of lots of founders, in Chicago, Boulder, and beyond.
It’s a tangled web of awesome, where a decade after Troy’s first interaction with Techstars, there are so many winners it’s hard to keep track. And the wins just keep piling up.
Companies, resources, and people mentioned in this podcast:
The God Particle: If the Universe is the Answer, What is the Question? By Leon Lederman with Dick Teresi
How the Internet Happened: From Netscape to the iPhone, by Brian McCullough
Next Big Sound – acquired by Pandora
Edited highlights from the conversation:
The origins of Techstars Chicago, and the power of a Give First network:
David: We’re really excited to have Troy on Give First today. Troy is one of the partners and founders of MATH Venture Partners, and we’ve known Troy for a long time. Troy is one of the reasons that Techstars is in Chicago, he was the managing director at Techstars Chicago and before that at Excelerate Labs, which was a fantastic accelerator. So we have a lot of history with Troy. Troy, welcome to the show. We’re really glad to have you today.
A lot of people might have heard the story of how we first met and how Excelerate Labs and Techstars came together. But a lot of people haven’t. I think it’s a really interesting story, so I wanted to give you some space to talk about that.
Troy: Yeah, it was fascinating. In 2008 I had been teaching entrepreneurship at Northwestern for awhile and I had some students in my class who were just different: Alex, David, and Samir. They were better than any other students I had had up to that point. When they did their final project, they presented their business plan, and all of the judges came up to me after and asked if they were doing this company for real, or if it was just for class. If it was for real, they wanted to talk to them. They were doing this thing around music and the internet and we rounded up about $25,000 in seed capital, which we had never done for undergrad students before.
They struggled for a while, and they really tried to get this thing off the ground. In 2009, Alex, the CEO, had graduated and David and Samir were still seniors in college, and they got accepted into this thing in Boulder called Techstars that I had never heard of before. When they told me about it, it sounded like they were going to get some capital and mentorship and spend the summer in Boulder, which sounded awesome. So they piled into David’s VW and drove down to Boulder to be part of the program.
David: You know, before they did that, Troy, I had to fly out to Chicago, and I met them in the airport. I remember it vividly.
Troy: I’ve heard that a little bit about this story. Yeah. To persuade them.
David: I used to fly to the airport of whatever town companies were in and take a meeting in the airport and then fly back. I remember meeting those guys, all just sitting in those crappy airport seats.
Troy: They came down to Techstars and—as it’s been told to me—they got there and on about day two of the program, they said this dog isn’t going to hunt, and they thought their business was doomed. David, you were there, so you can tell me a little more about what happened then.
David: They walked in—it was day two of the accelerator program—they said that they just didn’t believe in their business anymore. They were sort of saying, “We’re not sure we believed in it when you funded us.”
Our reaction was: okay, cool. Let’s figure out what we should do, because the investments is in you, not in this particular idea. We weren’t too sure about it either. So we just started brainstorming, and I remember a big whiteboard session that day.
Troy: Fast forward to the end of the program, 88 days later. I was down in Boulder for Demo Day and Alex did an amazing job with his pitch. I think he was asking for $350,000 in seed capital to launch this new thing around music on the internet that he called Next Big Sound. There was a line of investors waiting to invest. He actually ended up raising over $1 million in that round, turning people away. It was one of my first angel investments.
It was that day that I realized a couple of things. One was how awesome the program was for Alex, David, and Samir. It took them with this nascent idea that wasn’t going to work. It helped them figure out how to pivot, how to find a real business model, how to raise money—raise over a million dollars—and how to go into business. That was phenomenal.
The second thing was that there were a handful of us from Chicago who happened to be there. Techstars had just expanded to Boston. You had 10 companies in Boulder, nine in Boston. Of those 19 companies, five came from Chicago. That was awesome, except they all left and didn’t come back. Next Big Sound set up camp in Boulder because that’s where their lead investors were. They never made it back to Chicago.
I remember the date, August 6, 2009. There were a handful of us who were there, and we realized we wanted to do this in Chicago. So we reached out to you and to Brad and said, “Hey, will you do this in Chicago?”
I remember you came up to Chicago with Shaun, the managing director from the Boston program. We talked about setting up Techstars in Chicago, and then you pulled me aside and said, “We’re kind of busy. It’s under the radar, but we’re launching New York and Seattle. We don’t have the bandwidth to do this. We’re really focused on quality over quantity. We think you should do it. We’ll share docs and best practices with you, but it’s gotta be your thing.”
A handful of us—Sam Yagan, I2A Fund, and Sandbox Industries—decided we were going to do it. We launched an accelerator called Excelerate Labs just six months later. We ran in 2010.
You were super helpful. I remember we were on the phone with you asking questions all the time. And it was a great class. It did amazingly well. We did it again a second year, a third year, and then, at the end of 2012, Brad came up to Chicago and told us that he loved what was going on in Chicago.
Brad said, “You’ve got all this activity in the ecosystem, with 1871 and more, and we really want to have a presence here for Techstars, but we don’t want to compete with you. Would you consider joining forces and changing the name on the door?”
I thought it was an awesome opportunity to join the Techstars Network and have a reach that was much bigger than Chicago. We wanted to be part of that big network of mentors and investors and entrepreneurs.
It came full circle and we became Techstars Chicago.
It was a couple of years after that, 2014 or 2015, I think—Next Big Sound was acquired by Pandora, and that was awesome for those guys. It was a great event. It was great for the investors.
I got a nice return on my investment, and Alex sent me a really heartfelt handwritten note. He talked about how he wouldn’t have been where he is without that first class and without my support and mentorship. I was reading it, and while it made me feel warm and nice, something didn’t feel right. It just didn’t settle right. It took a minute for me to realize—wait a minute, I wouldn’t be where I am if it weren’t for Alex, David, and Samir having found Techstars and introduced me to that program.
When I look back at my personal trajectory over the last 10 years, the seminal event was Boulder Demo Day, August 6, 2009, when this ‘Aha’ moment happened of, “Oh my God, I want to be part of this network. I want to help entrepreneurs like this.” Without that, I wouldn’t have run an accelerator, I wouldn’t have run a venture fund, I wouldn’t have invested in all these companies. I wrote Alex back a note telling him: you’re mistaken, you’ve had a bigger influence on my life than I’ve had on yours.
David: Wow. What an incredible story.
I think a lot of people take this idea of Give First, and they know it’s not transactional, but if I help you, you know, someday it’ll come back to me. What I just heard is a story of Giving First coming back to everybody in different ways, right?
Because I feel the same way. Having the chance to work with you and building the Techstars brand in Chicago. And the Next Big Sound guys are coming back literally a week from when we’re recording this to help us with some new company ideation talks, and they’re investing now—they have Next Big Ventures. That’s their venture fund. That’s right.
It’s a network of effects that have happened because of the early Give First of you helping them in class and Techstars helping accelerate them a little bit early on—it just continues in this virtuous cycle. Give First is so much more than: I’ll do one thing and I’ll get something back. You just never know how it’s going to build upon itself to get really powerful for everybody involved.
Troy: I never would have imagined where this would have taken me when we first started. Excelerate Labs didn’t have any office space, didn’t know what a Demo Day was. We didn’t even have internet. We use wireless modems hanging out the window to provide internet to 30 founders. It was pretty ridiculous. Today, it’s pretty awesome to see all the companies that have gone through the program, and to be part of that worldwide network to help entrepreneurs.
The ripple effect
Troy: The first year we did Excelerate Labs it was really fun and new and it felt like we were building something cool. Then the second year we were doing it, and we didn’t have a budget, and I think that year I got paid less than a Barista at Starbucks. You know, my wife was a little pissed at that. But I was in a position where I could afford to do it. I wasn’t worried about how it was going to pay rent next month. It turned out that that decision to build Excelerate Labs, now Techstars Chicago, paid such huge dividends in the long run.
I never would have been in the position I’m in today without it. I wouldn’t have been offered the positions teaching at Booth or at Kellogg that I did. I wouldn’t have been able to start a venture fund. I mean, I’m sure it would have been fine, but I can trace so much of where I am today and the entrepreneurs I’ve gotten to engage with and to help to that early decision to volunteer time and start this thing called Excelerate Labs. It has had such an impact on my life and hopefully a ripple effect impact on dozens and dozens and dozens of others as well.
David: No doubt about that ripple effect. And hopefully any baristas listening are not offended.
Rapid Fire Round
David: I’m going to ask you four quick questions. You rapid fire answers. We just want to get people some new ideas.
We’ll start with this. Other than Chicago, what’s your favorite city?
Troy: I would probably say Wellington, New Zealand. I love New Zealand. I love all of the diversity of nature that it has to offer. Wellington has this cool little pocket of interesting people, cool coffee shops, a startup ecosystem. If I could move anywhere in the world with a snap of my fingers, it’d be Wellington.
David: I may see you there. It’s not a long drive from Queenstown, which I love.
What’s a great book you’ve read recently that you would recommend?
Troy: How the Internet Happened, which tells the story from the first browsers all the way through the launch of the iPhone. It was fascinating to me, having lived through all of that, to hear the inside story of what was really happening inside and how. All of those steps from MySpace to Facebook—they all impacted our lives in such incredible ways. I’ll never forget the first time I saw the first iPhone, I was like, wait, you have a phone that has no keys on it? That was just the craziest thing. Now we just accept that standard. It was a great book.
David: Okay. We’ll check it out. What charity would you urge people to get involved with?
Troy: Lurie Children’s Hospital of Chicago. My daughter had a pretty serious health issue 10+ years ago, and she had brain surgery. She is an amazing kid and has done amazingly well—she’s awesome and perfect and about to go off to college. We attribute that success to Lurie Children’s Hospital. Every year we try to support them the best that we can. I think that there’s nothing better we can do than to support future generations, whether in their health or their education. I’m always looking to support the next generation.
David: Awesome. Last question. Outside of your immediate family and, of course, present company, who’s the most interesting person you’ve ever met?
Troy: Probably one of the most interesting people I’ve ever met was Leon Lederman. Many people won’t recognize him. He was a Nobel laureate and a physicist. He invented the term ‘the God Particle,’ and he passed away recently. He was an amazing man, first of all, incredibly smart. I got to sit down at dinner with him and talk with him about any topic in physics. He had such passion and drive and creativity. And then he turned that into creating something amazing for the state of Illinois, which is the Illinois Math and Science Academy, a publicly funded high school. It’s a boarding school for the top math and science students in Illinois. Every year they take about 200 or 250 students, and it’s had a huge impact. So I think Leon Lederman was one of the most interesting people I’ve ever met in person.
David: Super Cool. Troy, thank you so much for sharing. Congrats on everything you’ve done in Chicago. And of course everybody should check out MATH Venture Partners. Thanks for being here, Troy.
Troy: Thank you for all you’ve built with Techstars.
How did Sphero CEO Paul Berberian make the number one toy in the world? Sphero got to make the BB8 toy robot because of a connection made during a Techstars accelerator. That’s the power of the network. Hear him tell that story, and more.
Have you ever been mobbed in Times Square, like a rock star? Paul Berberian, CEO of Sphero, the company that makes BB8, at one time the number one toy in the world, has.
Paul talks about how mentoring and Give First were essential to Sphero getting the BB8 gig.
He loves mentoring as well, and describes the experience of being a mentor and having a positive experience on someone’s life as “addictive.”
Listen for more on the transformative nature of mentorship—from both sides—plus more behind the scenes details on how one of the best loved Star Wars toys came to be.
Companies and resources mentioned in this podcast:
Raindance Communications – acquired by West Corporation
Edited highlights from the conversation:
The biggest lessons from being a mentor
David: We like to talk about experiences of mentorship on this show because we feel like a lot of people really get that Give First experience through mentorship, whether it’s something they’ve learned from someone or a way that they’ve been able to help someone else. Can you tell us the biggest lesson that you’ve learned about being a mentor or trying to help someone else?
Paul: I have two really big things that come to my mind when it comes to being a mentor.
The first is that it really doesn’t take a lot of energy, right? I don’t mean that it’s trivial, I just means that it’s actually pretty easy to be a mentor and to have a positive impact on someone’s life. It’s just being honest and listening and sharing your experiences so that hopefully someone can benefit from them.
The reason I share this is I’ve had people come up and tell me that I talked to them three years ago and said something really impactful. And I go, “I don’t know who you are. You sure it was me who talked to you?” They tell me, yeah, we met at this place.. and they have to go through this really long process to describe where we met. Finally my memory kicks in, and it’s amazing how something so simple and so small could have an impact on someone’s life.
The second thing I reflect on about mentorship happens oftentimes when I’m mentoring a young startup. I might be struggling in my own business, and they’re doing something that just doesn’t jibe with me—but they’re having success, and they don’t realize that while they’re talking about something they’re doing and they’re talking to me as a mentor, I’m secretly taking note.
I’m thinking, oh my gosh, look what they’re able to do with, you know, two matchsticks and a piece of bubblegum. We’re going to spend, you know, $100,000 trying to do something that won’t be nearly as effective. I’ve had numerous experiences like that, where the scrappy nature of a startup inspires me. You kind of lose touch with that scrappiness as you build a business. Sometimes it’s great to have that touchstone and see what young people are doing. I get a lot out of it.
Advice that changed your life
David: Is there something that someone shared with you that changed how you think about business early on?
Paul: I’ve been reflecting on this because I knew I was coming here today.
Jack Tankersley was one of the early Colorado legend venture capitalists and he was still an active venture capitalist when we first moved to Colorado back in 1994. We were approached to sell our company in 1995. We met Jack Tankersley and his partner Steve Halstedt at Centennial Ventures and we were faced with potentially selling our company or taking money from them. Jack could have been very selfish at that moment and said, “Let’s put some money into your business, let’s grow, build something big.” But he approached the situation from a different perspective; he didn’t approach it from a business perspective. Instead, he had a dialogue with me and my partners, and he asked about us personally. Are you married, do you have a mortgage? Do you have any debt?
He found out that we all had young kids, and we were all saddled with an incredible amount of debt, because we put our hearts and souls and our credit cards into the business.
Once he’d learned all this, he basically said, “You guys are smart. You’re going to do this many times in your life. Come see me after you sell your company and put some money in the bank. You’re going to be a much better entrepreneur after your first exit and success.”
That may not sound like an amazing piece of advice. But at that time it was very profound because I had never thought of myself doing this multiple times. And here’s someone who says, “I’ll be there the next time.”
It made me think about my career. I was around 28 or 29 at the time. His advice made me think about my career as the beginning of an arc. I’m gonna be doing a lot of different things in my life, and it’s okay to let go at this time of something that was my baby and to think about the next thing.
You become attached to something and it’s important to hear that it’s okay to move on.
David: There’s also that relationship piece, right? Where he was saying, “I’ll be there, too.”
Paul: Yeah, exactly. And that was really powerful. He was an investor in our next round and there were a couple of pivotal times over the course of our next business, which became Raindance, when he was there again, offering sage advice. He had a big impact on shaping me as an entrepreneur, he probably doesn’t know that.
Brad & David: We will make sure he hears this. We will spam him.
Brad: Jack is somebody who I consider a key mentor of mine. He was somebody I met very early in my own personal journey as an investor. I learned an enormous amount from him in the first three, four, five years of my own investing, both with investments that we got together and just talking to him and getting feedback from him and listening to him. He’s a great example of somebody who is very invested in relationships and less focused on optimizing for the transaction.
Paul: He really is. He really is all about the people.
The origin story of BB8 & getting swarmed in Times Square
Brad: Tell us about something that really sticks in your mind as a magical moment.
Paul: I’ll reflect on one that’s pretty recent. People may know of it. Sphero was involved with the Techstars accelerator program with the Walt Disney Company. It was back in 2014 and ‘15, and we were partnered up with mentors from the executive at the Walt Disney Company, and one of them was Bob Iger [Disney’s CEO], who met with all of the teams.
I remember the meeting with Bob Iger. Each company had 11 minutes with him, and in our 11 minutes he shows up and tells us about this new Star Wars movie coming out. There hadn’t been a new Star Wars movie in around 10 years. He says, “I know everything about you guys. We got a short amount of time, but let me show you something.” He pulls out his iPhone, and he shows us this new character.
It looks a lot like the product we were building at the time, which was a robot bobble. He says, “Can you guys make this into a toy?”
Of course we said, “Yeah, of course we can do that!” That’s the origin story behind BB8.
We went on to make BB8 and Star Wars: The Force Awakens was a big, successful movie, and we were the number one toy in the world.
I remember one very specific moment in time. There was an event in New York City at the Disney store when people were lining up outside the store at midnight to go buy BB8 when it first came on sale. The line went around the block. I was there as the company CEO to announce it.
I was literally swarmed in Times Square. I felt like a rockstar at that moment. I realized it was just a very brief moment in time, that it wasn’t gonna be here forever. But that was a pretty special moment. That was a fantastic moment.
David: Maybe they advertised it as Bob Iger was going to be there.
Paul: I think it was BB8. There were a lot of folks dressed up as storm troopers and Darth Vader.
David: Star Wars people are crazy. I mean, they show up.
Quick Fire Round
Brad: Let’s shift into a quick fire round.
David: We love Harry Stebbings. We love his show, Twenty minute VC. We’re totally ripping this off. We like to say that every time.
Paul: I did one of his shows way back when.
David: All right. A favorite book that you’ve read in the last year.
It was an audio book and I just finished it. It’s called Power Moves by Adam Grant. He interviews people at Davos talking about power and the section where he interviews women leaders is absolutely powerful. I’m going to go on for 13 seconds more because one of the most powerful things out of that book was the women leaders who said their success was because a man decided to mentor them so that they could elevate their careers. The fact is that if we want to see women in more powerful positions, we have to commit to mentorship, so that they can be successful. We can’t only go out to lunch with the guys.
David: Your favorite charity that you’ve supported and why.
Paul: My favorite charity is the Community Foundation.
David: A new startup people should check out.
Paul: I mentored Goally in the most recent Techstars cohort, and I think what they’re doing to help kids stay focused and get their lives in order is awesome.
David: A city that everybody listening has to visit.
Paul: Hong Kong.
David: Hong Kong. Awesome. Paul, thanks so much for being on the show with us today. We appreciate it.
Paul: Thank you.
So you’ve got a terrific idea for a startup? Great!
If you’re just starting out as an entrepreneur, you may feel overwhelmed by all the new vocabulary and concepts around building a business.
Techstars encourages all of us to #GiveFirst, so today my gift to you is a long list of great resources from across the web. Give these articles a read, and before you know it, you’ll be finding a great co-founder, building a MVP, acquiring customers, perfecting your pitch, and even raising a seed round!
BUSINESS: Defining and fine-tuning your core offering
- The business model canvas: https://strategyzer.com/canvas/business-model-canvas
- Building a MVP (Minimum Viable Product): https://rubygarage.org/blog/how-to-build-a-minimum-viable-product
- Achieving PMF (Product-Market Fit): https://www.forbes.com/sites/hayleyleibson/2018/01/18/how-to-achieve-product-market-fit/#44378185476b
- Running design sprints: https://www.thesprintbook.com/how/
- 10 steps to perfect your startup pitch: https://www.gsb.stanford.edu/insights/10-steps-perfect-your-startup-pitch
- Pricing your product: https://www.sequoiacap.com/article/pricing-your-product/
- Branding must haves: https://foundr.com/brand-identity-system-startups
PEOPLE: Finding and working with the right people
- Finding great co-founders: https://guykawasaki.com/how-to-find-a-co-founder/
- Creating the right culture for your startup: https://techstarsblog.wpengine.com/content/accelerators/creating-right-culture-startup/
- How great leaders inspire action: https://www.ted.com/talks/simon_sinek_how_great_leaders_inspire_action
- Three types of mentors you need: https://www.entrepreneur.com/article/327671
- Five rules for networking: https://www.forbes.com/sites/kellyhoey/2019/01/10/five-rules-for-networking-your-startup-in-a-new-city/#777ead803735
- How to write the best forwardable email: https://alexiskold.net/2015/06/24/how-to-write-a-forwardable-introduction-email/
TECHNOLOGY: Getting the tech correct
- What makes a good CTO? https://www.forbes.com/sites/theyec/2015/08/28/what-makes-a-good-cto-great-8-qualities-to-hire-for/#49e7a3e04b03
- Making engineering team communication clearer, faster and better: https://firstround.com/review/making-engineering-team-communication-clearer-faster-better/
- Common UI/UX website mistakes: https://techstarsblog.wpengine.com/content/startup-digest/common-uxui-mistakes-can-ruin-website-design/
- Understanding modern web development: https://levelup.gitconnected.com/web-development-introduction-39ed3544e95c
- What is blockchain? https://blockgeeks.com/guides/what-is-blockchain-technology/
- Everything you need to know about AI (Artificial Intelligence): https://www.zdnet.com/article/what-is-ai-everything-you-need-to-know-about-artificial-intelligence/
GROWTH: Getting customers
- Tools for understanding your customers: http://firstround.com/review/the-tools-early-stage-startups-actually-need-to-understand-their-customers/
- Marketing tactics: https://techstarsblog.wpengine.com/content/uncategorized/9-marketing-tactics-new-startups
- Marketing automation: https://techstarsblog.wpengine.com/content/startup-weekend/utilizing-marketing-automation-startup/
- The ultimate guide to customer acquisition: https://blog.hubspot.com/service/customer-acquisition
- Dictionary of marketing terms you should know: https://blog.hubspot.com/marketing/inbound-marketing-glossary-list
- Making sales a priority: https://tech.co/startups-you-need-to-make-sales-a-priority-2016-03
FUNDRAISING: Money to grow and scale
- Startup fundraising: https://techstarsblog.wpengine.com/content/accelerators/startup-fundraising-executive-summary/
- Raising money for your startup: https://www.inc.com/mark-suster/raising-money-for-your-startup-here-are-6-things-you-absolutely-must-do.html
- A fundraising template every entrepreneur can use: https://techcrunch.com/2015/05/30/how-much-does-your-startup-need-to-raise/
- What is an angel investor? https://www.startups.co/articles/what-is-an-angel-investor
- 16 startup metrics you need to know: https://a16z.com/2015/08/21/16-metrics/
- Nine seed funding gotchas: http://techstarsblog.wpengine.com/content/blog/9-seed-funding-gotchas/
- Why investors prefer founding CEOs: http://www.bhorowitz.com/why_we_prefer_founding_ceos
Read all these and still want more? The Techstars Entrepreneur’s Toolkit offers videos, exercises, and more to help you #domorefaster.
P.S. Last year I read 12 books. This year, I set myself a stretch goal, and I’m aiming for 48! However, I’m going to need your help. If you also like reading, tweet at me @iamsabakarim, and let me know what you’re reading so we can chat about it—and possibly feature your recommendation on my next Techstars Blog.
I only met Ron Conway once. He was an early investor in Datahug and when I met him it was at his home in San Francisco. This was not your normal investor meeting. It was all about introductions and understanding who I wanted to meet. It was sublimely simple yet hugely effective.
Just in case you haven’t heard of Ron Conway, he is probably the most famous and successful angel investor in Silicon Valley. He was an early investor in Google, Facebook, and Twitter and is an institution in Silicon Valley. Therefore, it was no surprise that we were A. delighted to have him as an investor and B. pretty nervous that we were about to meet this living legend.
We arrived at Ron’s apartment and were greeted by his associate. The meeting was probably about 45 minutes and I only really remember three things:
- Ron was very calm, laid back and friendly. He mentioned his Irish roots and that he had recently met the mayor of my hometown, Cork.
- I joked that since our vision involved unlocking relationships that someday “Datahug might build an automated version of Ron Conway.” I didn’t get the laugh I was expecting… Oops.
- Ron had several sheets of paper in front of him. Each of those sheets contained about 50 names. Every one of those names was a top tier VC, Angel or Corporate Dev Lead. This is when I discovered the power of having Ron Conway as your Angel investor.
Ron asked just one very powerful question, “Who do you want to meet?”
I rattled out four or five dream introductions without blinking. He asked his associate to go ahead and make those intros on his behalf. He said that he would make up to ten initial introductions and that if I needed more to get back to him for the next ten. He leafed through his printed Rolodex and suggested four or five more people he thought we should meet with. His final words were that if for any reason we didn’t see the introductions coming through we should just contact those people directly and “tell them Ronnie sent you.”
And that was it. 5 minutes later we were back outside his apartment armed with 10 hugely valuable introductions to key Silicon Valley insiders. We leveraged these introductions to build momentum, secure early customers and gain valuable insights into our markets. They made an impact on our business and I will be forever grateful and a fan of Ron Conway. I’ve not met with Ron since, but every now and then I’ll reach out to his team with an introduction or request for help. They are always responsive and great to engage with.
As an investor, and former founder, I want to add value like Ron Conway and his team did for us. I want to #GiveFirst and help other founders succeed where I can. I’ve been lucky enough to witness how one or two well-placed introductions have helped founders raise capital, win customers, and build their teams.
When mentoring teams here is why I always try to ask “Who do you want to meet?”
You discover how you can add value.
The answer to this question often triggers connections in my head that I would never have considered. You often don’t really know how you can help until somebody asks. The answer gives me a better sense of ‘directionality’ for how I might help.
For example, I recently spent time with a great founder in Bulgaria. We had a great chat and at the end, I asked my usual question. He immediately replied that his dream introduction was to the founders of Hired. I had randomly bumped into that founder twelve hours earlier and was able to take out my phone and connect them straight away. I would never have thought about connecting them until he implicitly asked for it as I had failed to see the connection (which became blindingly obvious when he explained why). They ended up hitting it off and spent several hours together which has led to more follow on introductions and meetings for that founder.
You learn more about the founders.
I have learned so much about founders by how they answer this question. It’s fascinating to hear about the types of people they want to meet. It’s also a really great way to gauge how focused and up to speed a founder is on their sector. Founders who can’t immediately answer this question with conviction immediately raise a red flag for me. You also learn a lot about the founder when they explain why they want to meet X or Y.
You remember the founder and their company.
You will remember really specific asks like ‘I want to meet owners of NFL or NBA Teams.’ It could be four months after you’ve met the founder when you might randomly bump into the person (or type of person) that the founder wanted an introduction to. These specific introduction requests always stand out in my mind and it’s a great way to reconnect with a founder by helping them with an introduction several months later. This proves to founders that you listen to them and genuinely want to help and support them.
You add more value to your network.
The best introductions are where both sides of the introduction benefit. By making highly targeted introductions you help create genuine win-wins. For example, other investors are often very grateful for targeted introductions to Founders who you are working with. The same is true for potential recruits, customers, and partners.
You get to #GiveFirst.
I’ve always been impressed by how Techstars has built their whole culture and reputation around this #GiveFirst mentality. Call it karma but being helpful today is probably the best long-term strategy to being successful as an investor in the future. Helping founders with introductions is not just good business but equally rewarding on a personal level when you can help entrepreneurs succeed.
Ron Conway and networks like Techstars are testaments to this simple, but often neglected, way of giving. It’s so simple to ask, can be hugely impactful, and costs very little in terms of time to execute. I’d encourage you to include it in your next mentoring conversation. 🙂
P.S. If you want to learn more about the #GiveFirst philosophy and it’s proven impact in business then read ‘Give and Take’ by Brian Lewis. I first heard about this from David Cohen and it’s a good read with good examples of how givers outperform takers.
Today we are excited to launch the Techstars Foundation.
Over the past year, many of our alumni, investors, and mentors have encouraged us to think hard about inclusive entrepreneurship. We decided that we wanted to do something very meaningful that would have a lasting impact on this issue — and so we created the Techstars Foundation. The goal of the foundation is to improve diversity in tech entrepreneurship by providing opportunities for underrepresented entrepreneurs through grants, scholarships, and sponsorships.
Creating the Techstars Foundation is also a way for us to take further action on top of the White House Diversity Commitment we made in August. That commitment involves increasing the numbers of female applicants and mentors in our accelerator programs, tracking and increasing minority participation, adding women to our selection committee, and publishing our diversity data annually. We want to do all of this as well as having a direct impact financially.
Founders and employees of Techstars, along with a number of alumni and mentors, have made an initial cash contribution to the Techstars Foundation, which launches today with more than $500,000. We are thrilled to offer a way for Techstars accelerator alumni, partners, mentors, Startup Weekend and Next alumni, and other supporters to Give First by providing access and opportunity to underrepresented minorities and – together – create stronger entrepreneur communities worldwide.
The Techstars Foundation is fortunate to have the guidance of an incredible board of advisors, including Brad Feld (Managing Director, Foundry Group), Mary Grove (Director, Google for Entrepreneurs), Jenny Lawton (Chief Strategy Officer, littleBits), Rod Robinson (Founder and CEO, Connxus), and Lucy Sanders (Founder and CEO, National Center for Women and Information Technology).
If you would like to get involved, please consider donating cash or stock to the Techstars Foundation. You can also name the foundation as a beneficiary. Your contribution is tax-deductible to the extent allowed by law.