Do you know how to be a great ally in the workplace? Why all startup founders should do karaoke? What the secret sauce of the Seattle startup ecosystem is? Create 33 Director Rebecca Lovell knows the answers to all these—and more.
Rebecca Lovell plays, as Brad Feld says, “a very important role in the center of gravity for the Seattle startup community.” Currently Director at Create 33, a resource center for tech entrepreneurs, Rebecca teaches entrepreneurship at the University of Washington and has held a number of roles in Seattle city government, from Startup Advocate to Acting Director of the Office of Economic Development.
Listen for more of her interesting career trajectory, which has gone through unexpected turns because of “nudges” given by mentors and others, resulting in Rebecca’s strong belief in the power of mentorship and giving first.
Then keep listening for actionable advice on how men can be allies to women in the workplace as well as Rebecca’s hilarious dive into why all startup founders should do karaoke.
Companies, people, and resources mentioned in this podcast:
- Backstage Capital
- Create 33
- Marie Curie
- Arlan Hamilton
- Illuminate Ventures
- The Moment of Lift: How Empowering Women Changes the World by Melinda Gates
- Janelle Monáe
- National Center for Women & Information Technology
- Cindy Padnos
- Eleanor Roosevelt
- Lucy Sanders
- Sayulita, Mexico
- Chrissy Teigen
Edited highlights from the conversation:
The secret sauce of the Seattle startup ecosystem
Rebecca: As I like to say, the secret sauce of the Seattle startup ecosystem is coffee. And it’s not just because we’re so highly caffeinated, but that can’t hurt. I think it’s that we have this undercurrent of collegiality and collaboration where you can get a cup of coffee with anyone that you want or need to meet. You combine that ethos with the lived experience of entrepreneurs and investors who just raised their hands and said Yes to supporting Techstars. That’s the moment that [Techstars Seattle, which started in 2010] stepped into. And now, you know, almost 10 years later there are 40 coworking spaces, there are 80 engineering centers located in greater Seattle. Facebook has the biggest footprint in Seattle, outside of its headquarters. We’re not just a one horse town dominated by Microsoft or even two horses, Microsoft and Amazon. It’s a really rich ecosystem. But you got here at pretty interesting inflection point in our story about ourselves as a community.
How can men be allies?
Brad: I’ve been very involved in an organization called National Center for Women & Information Technology for a number of years.
Rebecca: Lucy Sanders, absolutely.
Brad: I was board chair for a while and worked very closely with Lucy, and I learned a lot about this notion of male advocates or male allies. And I’d love to hear, in your words, how men can help around the issue of diversity and inclusion. From your frame of reference as a woman, how can men be allies?
Rebecca: Absolutely. I gave a couple of examples of when men can use their power and their privilege to promote women. The first case in my own personal history was that recruiter who happened to be a man who convinced me that I was management material and my classmate who was a man who convinced me that I just win things. They both had positions that they leveraged to open a door for me knowing that I would succeed. Those are just a couple of small examples.
I also think it’s in just everyday behavior and creating a discipline around making room for women. I kind of don’t like the phrase ‘lifting up’ women. What you really need to do is quit pushing us down. But here’s one way you can make room for us. I can’t tell you how many meetings I’ve been in, whether it’s in the tech sector or in city hall, where I’ll be one of just a few women in the room, and men categorically have a tendency to talk over us.
For example, if my colleague Jessica would make a point and the man running the meeting would run over her, I would make a point of saying, “to Jessica’s point,” then repeat what she said—it’s very critical to use her name—and then maybe add my piece to it. This is a technique that men can use. You can amplify women’s voices, but I can’t tell you how important it is to use their name when you do it. If you just repeat what she said, you will instantly be given credit for it. So be mindful of sharing credit, you know, shining a light on the incredibly important voices of women. Those are just small daily practices that you can engage in.
And then I think writ large, if you look at the deplorable share—disproportionately low share—of venture capital investment that women get, part of it is about the institutional bias that might be brought into a partner meeting on a Monday afternoon, where your bias is going to be towards investing in men. But the real issue that was uncovered by Illuminate Ventures out of the Bay Area, Cindy Padnos’ group, is you literally have to take more meetings with women. If you think about the venture funnel, if you take 900 meetings over the course of the year and that gets you to nine deals, you want to start at the top of the funnel by taking as many meetings with women entrepreneurs as you can.
So that’s a daily behavior change: just think about ways to find and say Yes to meetings with women entrepreneurs, and over time, both by changing the behavior of the men who dominate the VC industry and making room for more women to become investors and lead a VC firms—like Arlan Hamilton and Backstage Capital—that’s when we start changing the narrative and changing the results.
Karaoke as a metaphor for pitching your startup
Rebecca: The point of Karaoke is that it is 40% song selection, and in startup language that’s product market fit. You need to know your range, that’s your product, and you need to read the room, know your audience and try to pick a song that’s gonna resonate with them—that you can sing. That step one, that’s 40%. 50% of it is just selling it, getting on stage and acting like you own it. And that comes down to the grind and the execution that startups face. And if you do the math, that only leaves 10% for talent.
I love Karaoke, as I said, almost as much as I love entrepreneurship.
Rapid fire round
Brad: All right. First one. Favorite city in the world other than Seattle.
Rebecca: Well, would it be to visit, to live, to retire?
Brad: Oh, you get to define the way you answer the question.
Rebecca: All right. Just because I have such a hard time unplugging and truly chilling out and getting off the grid, I would say Sayulita in Jalisco, Mexico. I’m a scuba diver and there is no better way to get off the grid than sitting around with great food, amazing beach. This little town probably has as many chickens and dogs as it does people. And I’m almost hesitant to say it because it’s been this beautifully kept secret, but I love it there.
Brad: Second one, how about a book that you’ve read recently that you thought was fascinating?
Rebecca: Yeah, I have been this total podcast and audio book junkie of late and the one that I just finished up is Melinda Gates’ Moment of Lift, and it’s not for the philanthropy—I think that commitment as well known and the impact is well known.
I love reading books and learning stories when I can get some new insight. And what I loved about this book was hearing directly from the author—Melinda read the audio book—and she had this, what I think is a real startup-y, entrepreneurial approach to their theory of change. Like they went into the market of the developing world, knowing that there was a global crisis around children’s health and easily preventable diseases.
Their plan was to focus on kids, but when they did their customer discovery phase, in startup parlance, they spoke with so many women, mothers and learned that the most life changing thing they could do would be to provide birth control for these mothers. So they went in with a set of assumptions, but they did such a great job of listening. They pivoted to where they felt like they could make the biggest impact. That was a wonderful discovery that I got through that book.
Brad: I’d strongly recommend that book as well. I read it a couple of weeks ago and I think it’s going to be on my list of top nonfiction or memoir-type books of the year. I don’t know Melinda Gates personally, but you really get to know her from the book, which was another thing. It’s very hard for an author to do when they are going after a specific topic, and not have it just be an autobiography, and this certainly isn’t. You really get a sense of her as you read it, which is awesome.
A charity that you’d urge people to get involved in and why, especially for the listeners in Seattle?
Rebecca: Absolutely. I am a huge fan of a program called Apprenti that was launched by the Washington Technology Industry Association. This directly addresses the talent shortage that we have in the tech sector and seeks equitably shared prosperity. This is an accelerated training program for career changers who are seeking living wages and meaningful careers in IT. And they primarily focus on barriered and underrepresented populations like women, like people of color, like justice-involved individuals, like veterans. A remarkable story. They’ve now served hundreds of graduates with life-changing training.
Brad: Last question. Guns N’ Roses themed: If you could have dinner with anyone dead or alive.
Rebecca: Hmm. So I was a history major in college and have long been an admirer of Eleanor Roosevelt, just in terms of her commitment to race and social justice and gender equity. But if I were hosting, I would make it a dinner party and I would have Eleanor Roosevelt, Marie Curie, Janelle Monáe, and Chrissy Teigen. I think that would be a delightful party.
Brad: That’s a great group.
Thanks for the time today. And more importantly, thanks for all the awesome stuff you do for entrepreneurs and for everybody, both in Seattle and everywhere else.
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.
Entrepreneur, investor, and Techstars board member Wendy Lea remembers the beginnings of Techstars, her first encounters with #GiveFirst—and how mentors have changed her life.
Wendy Lea is a longtime entrepreneur and investor, as well as a board member and mentor at Techstars. With David and Brad, she digs into some of her first mentoring experiences and reflects on a time when a mentor changed her life.
Wendy was early in her career and had just been offered a promotion that would cause a lot of change in her life, and she was hesitating. Her mentor told her: the risk of saying no is very high. “If you say no, you’re playing small. You have a lot of potential, and you need to go explore that potential.”
She did, and she traces her success back to that encouragement and good advice.
Listen for more about the risks of saying no… and saying yes.
Bonus: Listen to Wendy, David, and Brad reminisce about the first Techstars class.
Companies and resources mentioned in this podcast:
EventVue – closed
Get Satisfaction – acquired by Sprinklr
OnTarget – acquired by Siebel Systems
Siebel Systems – acquired by Oracle
An edited transcript of the conversation follows:
David: We’re really excited to have Wendy Lea here as a guest today on the podcast. Wendy is a board member at Techstars, and she recently moved back here to Boulder after spending four years in Cincinnati as the CEO of Cintrifuse. Welcome, Wendy.
Wendy: Thanks a bunch. That was a fun gig by the way, Cintrifuse. I’ll end on that.
David: Spend a few minutes giving us your origin story.
Wendy: A little bit about my background might help those of you listening grok my experiences and where they come from. My big success came with a company called OnTarget, and it came after lots of professional training in large companies. With OnTarget, three or four of us worked like dogs to make that work around the world. We owned it 100%, and we sold it for $150 million to Siebel Systems in 1999.
After that, I worked for Siebel, which was fantastic. I loved that because I learned a lot, and then I took that experience and started doing new things with it, for example, really working with venture-backed startups. That was very different: the risk, the reward, and the kind of mentoring that startups required. It was this that brought me to Boulder. In Boulder, I worked with companies like Lead Works—formerly Duo—and also Numerics.
Then I went to California. I made a bunch of angel investments and I did a big tour of duty at Get Satisfaction. Get Satisfaction was a big love, my biggest love in all of my work life. It didn’t turn out as planned, but it was quite remarkable. I’m back here in Boulder now, and proud to serve on the Techstars advisory board.
Brad: Wendy, would you talk a little bit about how you got introduced to Techstars and what your involvement with Techstars has been?
Wendy: At the very beginning it was an ask from you to plug into the community. From there you introduced me to David, and David told me about his big idea about bringing entrepreneurs and mentors together. That’s the first time I heard about Techstars, and that was the first cohort. I’ve hung around with a lot of mentors, and I became plugged in through the community that Techstars created here in Boulder.
David: Back then, that was really the first super visible example of Give First in Boulder. There were so many mentors who were trying to help that first class of 10 companies—which turned out to be a great class—and get this whole mentorship-driven accelerator thing going.
Tell us about your biggest lesson as a mentor.
Wendy: My biggest lesson as a mentor was with a company called EventVue. The founders, Rob Johnson and Josh Frasier, had an idea that was completely easy to understand. It wasn’t complex and crazy. I really got it and I liked what they were doing.
They were very, very early in their life cycle as entrepreneurs and they were impressionable. If a mentor told them something would work out, they really believed it. It was a struggle because I didn’t want to dispute other advice they were getting, but I suspected that the situation wasn’t going to work out. That was tricky, because you want to be upbeat. I believed in what they were building, and they were working like dogs. Of course, it didn’t work out.
Now when I see them, they always say, “Oh, I’m so embarrassed when I look back and think that I was so cocky.” And I say, “You know, it happens.”
David: So you were trying to manage that dynamic.
Wendy: I was trying to manage their expectations. This was before all the cool modules that we have now in mentoring, it was just us bushwacking through, doing what we could to give back. It was tricky. I did what I was taught as a young woman: ask a lot of questions, and see if they’ll tune into that reality or not.
Brad: Wendy, you’ve been involved in lots and lots of companies, both as a founder or entrepreneur, and you’ve been brought in by a bunch of startups to help by serving on their boards. You’ve also been a startup investor. When you reflect on all of those experiences, what’s the most fun you’ve had with a company?
Wendy: Building out the leadership teams.
Brad: Can you talk us through an example?
Wendy: On the venture backed side, it was awesome building out the team at Get Satisfaction. It was also hard.
Brad: What were some of the awesome things?
Wendy: We were really trying to figure out the match between the skills and knowledge that were being represented, and the needs we had on the team. We hired someone, and it turned out we brought in the completely wrong person.
He didn’t know how to get his hands really dirty: sit with the engineers and talk with them directly about what they saw in the code. The code needed to be refactored. It was going to be an expensive proposition. We all kind of knew that, but the guy was saying all the right things. He affiliated more with the product managers, and not with the engineers, and it caused problems.
That was a significant turning point for me, because I don’t have that background. I had to listen and learn and ask the founders. It was exciting and scary and costly when you did it wrong. I made a big mistake there and it really cost the company a lot of time and money.
David: Yet it was awesome.
Wendy: It was awesome.
David: Sounds like you learned a lot there.
I’m curious if you have an example from your career, Wendy, where somebody gave you some advice early in your career that really changed a lot for you?
Wendy: I’ve got one example from early in my career and one from later.
I had an opportunity as a young woman, in my mid-twenties. I got a promotion that required me to move from Jackson, Mississippi to New Orleans. It looked very risky to me. Personally, I’ve gone through a lot of change, so I can deal with personal risk, but I like my professional life to be stable. I was worried about moving and not knowing anyone in New Orleans. My husband couldn’t move with me.
My mentor, who was one of my bosses at the company, said to me, “The risk of saying yes is really very low. The risk of saying no is very high.”
I didn’t get it. My brain was going crazy. He told me, “If you say no, you’re playing small. You have a lot of potential, and you need to go explore that potential. So you don’t know anyone. You’ll meet people.” I’d never thought of that: the risk of yes versus the risk of no.
I told my husband I was moving to New Orleans. Of course he didn’t come. Yes, there was a divorce. Life continues. But that comment about playing small really made me think, and taking his advice changed my life.
The other advice, from later in my life, was from Rob Hayes, who’s a very dear friend at First Round Capital. He was an investor in Get Satisfaction when one of our first term sheets was pulled. The company had no money. We had zero. We were funding it ourselves, we weren’t doing well, and the term sheet got pulled. I didn’t know to be upset about that. I had not had enough experience to freak out when this happened.
Rob understood what it meant, and we met at a coffee shop. He asked me what we were going to do, and I told him that we would keep looking for money and I would invest and we would keep going.
I loved this company, and he was just like, “Wow.” Then he said: “I support you.” For Rob, if I thought there were conditions that we could build around, he was going to support me.
Brad: In 60 seconds or less. What does Give First mean to you?
Wendy: Give without expectation of return.
David: That’s far less than 60 seconds. I’m going to start using that.
The other thing I’d love to hear about is an example in your life where you’ve seen the power of Give First in action.
Wendy: There are lots of those! Here’s one. I was working with some universities in Cincinnati, and we were doing a coaching workshop, teaching people how to do good coaching or good modeling, showing behaviors by doing them. We were working one day in the engineering school, in a coding class. One of my students went over to a young woman and sat down with her. He said to her, “I can tell you’re struggling with this. What can I do to help?”
No one told him to do this, and I didn’t instruct them to run around the room and help each other out. That was good observation and good modeling. I’m really proud of that. It was very natural, so she didn’t feel awkward.
The more we model this behavior—giving without keeping score, and without needing immediate reciprocity—that will change the scope and slope of the work we do. If you model it suddenly and set expectations suddenly, then people lean in. They learn how.
Brad: That’s great. The last section here is something that we lifted from our friend Harry Stebbings, a quickfire round. We’re going to ask you a handful of short questions and we’d love very, very fast answers to each one of them.
David: Let’s do it. Wendy, what’s your favorite book you’ve read in the last year?
Wendy: Small Fry, by Steve Job’s daughter Lisa.
David: Do you have a favorite charity you support?
Wendy: I support the SPCA because I’m a big dog lover.
David: Tell us about a startup you met recently that you think people should check out.
Wendy: I’m very excited about Pipeline Equity, which happens to be a Techstars company, led by Katica Roy.
David: What’s a city that you think people have to visit before they die?
Wendy: I would say Oxford, Mississippi.
David: You did it. You’re through it. Thanks for joining us, Wendy. It’s been a blast having you.
Wendy: My pleasure. Thanks for having me.
Today, I’m excited to announce the launch of the very first podcast from Techstars: the Give First podcast. Brad Feld and I are co-hosting this weekly podcast that digs into what Give First means.
I can tell you that I’m having a great time making it, and I’ve already learned so much from the people we’ve had as guests.
What is Give First?
Give First is one of our core values here at Techstars. It means helping others with no specific expectation of return. It’s not transactional—it’s the idea that if you’re helpful, it will come back to you in completely unexpected ways.
Why Make a Podcast?
This is great, but I know it can sound a little abstract if you haven’t experienced it yourself. You may be wondering if it really works. Do busy people—and entrepreneurs are notoriously busy people—actually stop and Give First?
Yes, it really works.
I hope that you listen to the Give First podcast for insights into how exciting and successful a life and career guided by the principle of Give First can be. Here are just a few examples from the first few episodes:
- Hear Paul Berberian, CEO of Sphero, tell the story of being mobbed in Times Square like a rock star when Sphero’s toy BB8 was the number one toy in the world.
- Listen to Wendy Lea talk about the risks of saying “no” when opportunity comes knocking.
- Troy Henikoff tells a decade worth of Give First stories that all intertwine—and resulted in companies growing, careers thriving, and millions in funds being raised, all while the Chicago startup ecosystem is expanding.
- Mary Grove shows the power of Give First at scale, with her adventures in community-driven change, starting Google for Startups and traveling on the Rise of the Rest bus.
Like I said, Brad and I are having a blast making the Give First podcast. We get to have fascinating conversations with accomplished, generous people. But most of all, Brad and I are making this podcast as yet another way to Give First. We hope that by sharing these stories with you, you’ll be inspired to Give First as well.
Listen now to our introductory conversation, where Brad and I talk about where the idea for Give First came from and what it means to each of us. And subscribe to the Give First podcast!
1. How DigitalOcean came be the second largest cloud computing platform.
2. I’ll explain my quote, “’We did everything wrong for a decade.” What were the biggest mistakes I made and how did I look to rectify and learn from them?
3. My thoughts on if / how one can learn to be a great business leader. Is it inherent or if not, what are the steps required to increase your chances?
4. How does DigitalOcean fundamentally scale love? What are the inherent challenges of building this type of culture? How does the theme of love play out in the hiring and the onboarding process?
I love the 20 Minute VC podcast. It’s the perfect amount of time and Harry Stebbings does a great job attracting interesting guests and asking them the right questions. I was honored when asked to be on the show, here’s that episode.
Harry asks me questions like:
- How did I make the transition from Founder to VC with Techstars and Fund I?
- Fund I is one of the most successful funds in history; what was the structure with Fund I? Why did you choose a $5m fund size? How did you decide initial to follow on ratio?
- Why were you so valuation sensitive with Fund I? Why were you so rigid on a consistent check size on Fund I?
- Why did you decide to expand from being a solo GP fund? What are the challenges and complexities of fund scaling and how did you approach this?
- What do you think about uncapped notes?
- Why do you like big boring companies?
- How did you meet Ryan Graves @ Uber and how did the Uber investment come about? (even more about that here)
- Where does David still see inefficiencies in the current venture model?
I hope you enjoy it. I had fun doing the interview.
The Twenty Minute VC takes you inside the world of Venture Capital, Startup Funding and The Pitch. It helps you discover how you can attain funding for your business by listening to what the most prominent investors are directly looking for in startups, providing easily actionable tips and tricks that can be put in place to increase your chances of getting funded.
Startup Weekend might be over, but for those curious about how it all went down, we’re happy to share a behind the scenes look at the event with conference podcaster Clark Buckner. On-site at the Nashville Entrepreneur Center (EC) for the event, Clark spoke with participants, sponsors and mentors to see what they had to say about #SWNash and the Nashville startup community in this series of short interviews. Previously at TechnologyAdvice, Clark continues as a full time podcaster integrating custom content strategies with organizations around the country, Southeast accelerators and digital media marketing conferences. You can also find him at his weekly podcast “The Nashville Entrepreneurship Story” as told by the EC.