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 protected].

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: [email protected] 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 protected]

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.


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