“The true path to happiness is to have meaningful work and meaningful relationships,” Heidi Rozen says. She brings these two elements together as a VC working with entrepreneurs who are changing the world for the better. Her humane take on being a “mentor capitalist” is deeply Give First.
Heidi Roizen has called herself a recovering entrepreneur. Wendy Lea has called Heidi “the epitome of Give First.” Both of these are true, and go a long way toward describing the deeply humane perspective on the role of venture capital that Heidi brings to her current role as a partner at Threshold Ventures.
Heidi was an entrepreneur herself for 14 years before exploring other career options (VP of Worldwide Developer Relations at Apple, for example) and eventually settling in as a venture capitalist—or “mentor capitalist,” as she sometimes says, in a nod to the profound importance of mentorship in the role.
Heidi likes to joke that “entrepreneurs should be really careful about picking their venture partners, because the average VC relationship lasts longer than the average American marriage, and it’s probably easier to get rid of your spouse than it is to get rid of your venture capitalists.” There’s truth hidden in that joke: the VC-entrepreneurship relationship is a human relationship, not just a financial one. Heidi takes the human side just as seriously as the financial. She wants success in all areas, and sees how thoroughly the two are entwined.
For Heidi, “the true path to happiness is to have meaningful work and meaningful relationships.” She’s achieving this by working with amazing startups that are making the world a better place, and helping to make them better companies.
That sounds like Give First to us.
Listen for Heidi’s fantastic insights about how life and work mesh—and listen all the way through for stories about Heidi’s epic underground casbah from the dot com boom and why one of Heidi’s kids calls Brad Feld “toenail boy.”
Listen for Heidi’s take on…
The true path to happiness:
“The true path to happiness is to have meaningful work and meaningful relationships. And I think one of the beauties of the entrepreneurial environment that we live in is very often you form your meaningful relationships through doing meaningful work together.”
“I go into life thinking I’m about building relationships. I’m not about transactions, I’m not about win or lose or this is what am I going to get out of this deal. I’m about, you are a fellow traveler in life that I have met and if I can build a relationship with you, out of that will come good things. Or if not, not. But I’m always trying to optimize for the relationship over the transaction.”
“I’m such a huge believer in serendipity or what I call controlled randomness, right? The idea that you don’t necessarily know when you go into something what you’re going to get out of it. But if you position yourself in a place where you’re going to find other people that are doing interesting things, it’s likely that something good will come out of that. If you just put yourself in the mix and say, ‘I’m here to be helpful, what can I do?’”
“Just remember, we’re all people first. We’re our jobs second.”
The relationship between entrepreneurs and VCs:
“I only succeed if the company succeeds, and I really enjoy that alignment. I also really enjoy the idea that I get to be a part of a team for a long period of time.”
“I often joke that entrepreneurs should be really careful about picking their venture partners because the average VC relationship lasts longer than the average American marriage, and it’s probably easier to get rid of your spouse than it is to get rid of your venture capitalists. So both parties should go into this with their eyes wide open.”
“I say this to my entrepreneurs a lot, there are things you are doing that no one’s ever done before and those should be hard. There are things you’re doing that other people have done before. And those should be easy. You know, it should not be hard to design compensation schemes. It should be not difficult to put your financial operations in order. Those are all places where we can use best practices and stand on the shoulders of others to create the best situation we can.”
Companies, people, and resources mentioned in this podcast:
- Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones, by James Clear
- Case Study: Heidi Roizen
- Memphis Meats
- Stan Meresman
- National Center for Women & Information Technology (NCWIT)
- Peninsula Humane Society & SPCA
- San Francisco SPCA
- Tina Seelig
- There There, by Tommy Orange
You don’t have to be in Silicon Valley to start a successful company. Marc Nager, Co-founder of Startup Weekend, and Dave Mayer, Founder of Aspen Entrepreneurs, are pros at building ‘non-urban’ startup communities. Listen for insights into how Give First helped them grow startup ecosystems in Telluride, in Aspen, and beyond.
Too many people believe that you have to be in Silicon Valley—or some similarly hyped tech-obsessed locale—to be an entrepreneur. Techstars knows this isn’t true: successful entrepreneurship can happen anywhere.
Marc Nager and Dave Mayer are living proof.
Marc is the Co-founder of Startup Weekend, the former CEO of UP Global before it was acquired by Techstars, and Techstars Chief Community Officer after the acquisition. He is on a mission to bring entrepreneurship to rural America.
Dave is the Founder and CEO at Technical Integrity and Massive Impact and the Founder of Aspen Entrepreneurs, and an active and passionate member of the Colorado startup community.
Both are hugely active in their local startup communities, Marc in Telluride, CO and Dave in Carbondale, CO outside of Aspen, and both see how entrepreneurship can thrive in these relatively small places—and what entrepreneurship can bring to them to make them economically sustainable for the long term.
Listen to hear Marc and Dave talk with Brad Feld—who literally wrote the book on Startup Communities—for a deeply thoughtful exploration of the how and why of entrepreneurship in a ‘non-urban’ environment.
Listen for Marc’s and Dave’s take on…
Marc and Dave on the economic benefits—and potential—of entrepreneurship in a small town:
Marc: “I fundamentally believe entrepreneurship is the most powerful force in advancing human welfare.”
Marc: “We can look at Telluride as a microcosm for what’s happening in the rest of the country through the lens of economic development, and see how can entrepreneurship can play a massive part in a vision for creating a more sustainable economy over the long term.”
Marc: “You find some incredibly accomplished people in these small towns. Likely they’re the people who grew up here who went off, had careers, and came back, and they’re looking to participate in different ways, as entrepreneurs or as investors. You end up with a vast resource of this intellectual and financial and network capital in these small towns.”
Dave: “For me it’s about quality of life, right? Broadband means that people can work from wherever they want now. All you need is a laptop and a great internet connection and a great idea—and obviously an ability to execute—and the ability to build a great team around you.”
Dave: “The word entrepreneur, the word startup—some people worry that we’re going to attract a Facebook to some 50,000 person valley and it’s going to change everything. That’s not really the goal, right? It’s getting five or 10, $10 to $20 million companies that can create real jobs for people and give them great health care. Those people can raise their kids here, live the life that they’ve dreamed of, and not be forced out by these rising prices around Aspen or Telluride.”
Marc and Dave on the new definition of success:
Marc: “The new American dream isn’t getting a fancy job and climbing the corporate ladder. It’s about living and working where you want—and having meaningful work.”
Dave: “Everybody has their own definition of success. And if that means working out of a coffee shop and hitting a powder day and then working with your friends and on something that you’ve been dreaming about forever, then that’s an easy one. That’s an easy success.”
Companies, people, and resources mentioned in this podcast:
- Techstars Startup Weekend
- Stephanie Copeland
- Greater Colorado Venture Fund
- Telluride Venture Fund
- Jesse Johnson
- Justin Lewis
- Mercury Payment Systems
- Roaring Fork Technologists
- Hunter S. Thompson
- Telluride Venture Accelerator
- Aspen Entrepreneurs
- Mental Health and Wellbeing in the Startup World (12016 Boulder Startup Week)
- Technical Integrity
Harry Stebbings, founder of the Twenty Minute VC podcast and Stride.VC, spends time every day connecting with each of his new followers on social media. He ends every email with “How can I help you?” Listen for more on how he built his podcast to over five million downloads per month, and how he Gives First every day.
Stride.VC founder Harry Stebbings is probably best known for his podcast, The Twenty Minute VC, the world’s largest media asset in venture, with over 5 million downloads per month. He’s talked with amazing Venture Capitalists and entrepreneurs and made over 2,800 shows, and he spends 45 minutes every day DMing each one of his new followers on Twitter in order to build a network with a truly human touch.
When he was 13, Harry watched “The Social Network,” the movie about Facebook’s growth, and it inspired him to become an entrepreneur and investor. At 18, he set up the Twenty Minute VC. With $50 in the bank, he literally stood at a crossroads and spent $10 on the domain and $20 on a microphone: “So I’d spent, you know, 60% of my net worth on this podcast in the space of 10 minutes. And it made me do it. It was the forcing function and that was the start.”
Harry learned about giving first from David and Brad as well. “I don’t understand how you guys do it. You guys were always responsive, kind, giving of advice,” he said, thanking David for his support as he was just starting out. “It’s just incredible and blows my mind that with everything that you have going, you’ve have the ability to carve out the mental discipline and the rigor to really engage and Give First.
David immediately returned the compliment: “When I follow the pattern of your show and talk to people that know you, almost everyone said that that’s who you are and they don’t understand how you do that. So however you do it, maybe it’s how we do it. And maybe it’s just a mindset, right?”
Give First truly is a mindset.
Listen for Harry’s take on…
The kinds of companies Harry likes best to work with:
“I love working with two to 10 people, forming teams, early product.”
“The best companies fundamentally own their lines of distribution.”
“I’ve sometimes found that the best VC is or less motivated by [money] and more motivated by just helping.”
“Money is fantastic in many ways. But it’s the outcome of the work that I do.”
How Harry maintains the human relationships in his network as it grows:
“Get off email. … A lot of what I’ve done actually is moved a lot of the relationships that were more professional relationships and transitioned them into friendships, through moving platforms: from going to Instagram, to going to WhatsApp, Snapchat, whatever that platform may be. But you just get so much more depth in the relationship through the less formal rigid platform.”
“In terms of the expanded network and how you deal with it, you’ve got to commit to it. If you’re going to pursue this strategy—it’s not a nice word to say, ‘strategy’—but if you’re going to see this as the way that you want to work, which is how I want to work, people-centric, human-centric, and personality based, then that is part of your workflow. You spend less time on email, you spend less time doing other things and you have to commit yourself to it. Is it easy? No, it’s insanely hard. I spend 45 minutes every night DMing every new single follow on Twitter, thanking them for following me. I’ll mention something about the city that they’re in, whether it’s I’ve been to it, I’d love to go to it, I’d love to run through it. I hear they’ve got great mojitos, monuments, whatever that may be. And build a relationship with them. The community is incredible.”
Companies, people, and resources mentioned in this podcast:
- The Twenty Minute VC
- “Anna Karenina” by Leo Tostoy
- “Bad Blood” by John Carreyrou
- Carmen Alfonso Rico
- Fred Destin on Twenty Minute VC
- Kent Goldman on Twenty Minute VC
- Bill Gurley on Twenty Minute VC
- John Henderson
- Josh Kopelman on Twenty Minute VC
- Mattias Ljungman
- “Madame Bovary” by Gustave Flaubert
- PillPack on Twenty Minute VC
- Skien, Norway
- “The Social Network”
- “Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts” by Annie Duke
- “Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist” by Brad Feld and Jason Mendelson
- Henry Ward on Twenty Minute VC
- Wired article on Harry Stebbings from Dec 2016
Subscribe to Give First with David Cohen and Brad Feld to get new episodes weekly.
René Pons, co-founder of PPAP Manager, has founded a company in Mexico, run Techstars Startup Weekends across Central America, and gotten into Techstars Detroit. Everywhere he goes, René Gives First and strengthens the startup ecosystem.
In early July, a week before Techstars Detroit kicked off, TechCrunch ran an exclusive article announcing the new class of 10 companies that are, right now, enmeshed in their three month accelerator program. The article noted that the program name and focus have changed, from Techstars Mobility to Techstars Detroit: “Mobility is baked into Detroit, but Detroit is more than mobility.” The Detroit startup ecosystem is strengthening and expanding, and becoming ever more appealing to startup founders from around the world.
Techstars has believed in Detroit through the hard times—we announced the first Techstars mentorship-driven accelerator program in Detroit the same day the city came out of bankruptcy. Ever since, Techstars has been a part of building better times for the Comeback City, helping to grow the startup ecosystem, making connections that benefit corporations and startups alike, and attracting new companies to the region.
If you’re a startup that does business with automotive or manufacturing, you need to get to Detroit.
We’re beyond excited about every one of the 10 companies in the 2019 Techstars Detroit class, but one in particular has not just a great business, but a founder who lives the Techstars value #GiveFirst, and who has been a force for startup ecosystem building for years in his native Chihuahua, Mexico: René Pons, co-founder of PPAP Manager.
First, the company: PPAP Manager is a platform to streamline the approval of packets of documents required in the automotive industry, known as PPAP (Production Part Approval Process), to validate production parts.
There are 30,000 parts in your car, and every one of them journeyed a long distance, often passing through several sets of hands, before your vehicle arrived, shiny and new, in a dealer’s showroom. The global journey of each one of those 30,000 parts is documented by a PPAP.
PPAPs are crucial to safe car production because they are the quality assurance for its parts. Yet today, most PPAPs are handled using spreadsheets or google docs, solutions cobbled together by individuals at different companies. They’re not fast, they’re not efficient, and worst of all, they’re not trustworthy enough for such important information.
PPAP Manager aims to solve this problem for the global automotive industry by providing a single tool that documents parts as they go through all the many suppliers in the value chain, making these records both accessible and accurate, so that you know that the brakes on your car won’t fail. They’ve been checked. They’ve got a good PPAP tracing them back through production, assembly, and testing.
René has started a few companies, and he got the idea for PPAP Manager from his co-founders, Vinnie Delgado and Jeefb Santos, who have worked in the auto industry for more than 24+ years altogether. They were looking for opportunities in manufacturing that would solve a defined and important problem, and had plenty of room to scale. PPAPs provided exactly the right kind of opportunity.
“The land of opportunity for the automotive industry”
“PPAP Manager fits our investment thesis to a T,” said Ted Serbinski, Managing Director of Techstars Detroit. He saw the same opportunity that René did, loved the founding team, plus he knew what Techstars Detroit could do for the company. “PPAP Manager should be doing business in Detroit, and Techstars is the best way to make that connection,” Ted said.
Ted’s on a mission to change entrepreneurs’ perception of doing business in Detroit, and one of his favorite techniques is to bring in entrepreneurs from all over the world—and then let the city, and the Techstars experience, speak for themselves. In five years, he’s brought 54 startups to Detroit from eight different countries—the 2019 class alone is 60% international, with founders hailing from five countries outside the U.S.
“Detroit is the land of opportunity for the automotive industry.” —René Pons, Founder of PPAP Manager
For Ted, the message is clear: If you’re a startup that does business with automotive or manufacturing, you need to get to Detroit.
René agrees. “Detroit is the land of opportunity for the automotive industry,” he said. “There’s no better place for us to be.” René sees that more and more companies globally are trying to get standards working, and that Detroit is a great place to work with many of these global auto companies, to spread these standards quickly. René is hoping that Techstars Detroit will get PPAP Manager to a proof of concept in partnership with one or more of the program’s corporate partners—who he sees as hungry for the kind of quality assurance that his company can provide.
Power of the Network
René knows how important connections are—one aspect he values in the Techstars accelerator is its diverse corporate partners, including Lear Innovation Ventures, Ford X, AAA, Avanta Ventures, USAA, Nationwide, Honda Innovations, and PlanetM.
He knows the importance of great connections—to other entrepreneurs, mentors, and investors, as well as corporations—for helping startups grow because he’s seen this power, over and over again, as a Community Leader helping to run Techstars Startup Weekends across Central America. Since 2012, René has organized over a dozen Techstars Startup Weekends, most of them in Mexico, but also as a facilitator in Honduras, the Dominican Republic, Colombia, and one in Seville, Spain, when he was briefly living in Madrid and wanted to get involved in the local startup community. Two years ago, he organized six Techstar Startup Weekends at once, all in different cities, three in one weekend and three the next. He describes himself as “the crazy organizer who tries to do different stuff.”
René loves Techstars Startup Weekends because they change how people think, and then give them the tools and connections to start putting that change into action. “The first thing we need in Latin America is to change the way we are thinking,” René said. “We don’t have enough people building or starting new companies. People need to realize that they can take control of their lives and start solving the problems that they see.”
He sees the first step as getting people to try new things—like attending a Techstars Startup Weekend—and from this experience, new entrepreneurs and new companies will grow. René is happiest when he sees the locals in a community step up and start working. As a Techstars Community Leader, he knows the formula for a Startup Weekend, and his goal is to get the event rolling in each new community, and then leave the team there to keep it going. This is how the events—and the entrepreneurial spirit they engender—spread.
“You learn a lot by getting involved and Giving First.”— René Pons, Founder of PPAP Manager
To René, Detroit is a model for where he hopes to see Latin American cities get to, with an evolving startup ecosystem and lots of opportunity for making connections and building businesses.
Give First Wherever You Go
And, of course, René plans to get involved in the Detroit startup ecosystem, above and beyond participating in the accelerator program. “Wherever we go, we need to get involved. I’m looking forward to knowing people and to start sharing with them and learning from them,” René said.
René lives the Techstars value Give First, and he practices it wherever he goes. “You learn a lot by getting involved and Giving First,” René said. “The connections you get from being there and sharing with the community—you cannot put a price on it.”
How Startup Ecosystems Grow
At first glance, Chihuahua and Detroit may not seem to have much in common. But now they share René Pons, and that’s a bond that will show results, we suspect. Maybe one day soon, they’ll both be known as startup hubs—growing companies, attracting talent, and transforming their regional economies. Entrepreneurship is powerful.
Detroit has become a place that startups want to move to. Five years ago, post-bankruptcy, Detroit was a hard sell for startups. Today the supportive startup ecosystem and the affordable cost of living make it a desirable—and smart—place to start a business.
René and PPAP Manager have moved from Chihuahua to Detroit for the three months of the accelerator program, and René plans to get involved in the local ecosystem. It may even make good business sense to keep PPAP Manager in Detroit long term.
But that doesn’t mean René has abandoned his home, or the Chihuahua startup ecosystem. Long term, his dream is to invest in small companies in small cities all over Mexico. “There’s lots of talent with great ideas in Mexico,” he said, “But they don’t have the money to build a prototype. At that early stage, these companies need more support.” René wants to give that support, and be an angel or seed investor who helps make this startup ecosystem go.
Ask Chris Heivly, Techstars VP of Innovation, about how startup ecosystems develop, and he’ll tell you that “ecosystem development is all based on success through a thousand nudges.” Connectors and believers like Ted and René provide these nudges constantly, doing their part to grow their ecosystems.
They believe that entrepreneurs create a better future, and they’re doing their part to make that better future—one PPAP, one Techstars Startup Weekend, one company, one accelerator, one city at a time.
Can you give too much? John China, President of SVB Capital, reflects on how mentorship helped him grow into an executive, and on whether, at some point, you need to see payback from all your giving. Spoiler alert: the answer is no. Never stop giving.
In over 23 years at Silicon Valley Bank, John China has made it his mission to make connections between entrepreneurs, investors, corporations, and more. Many, many entrepreneurs at Techstars and beyond have benefitted from his Give First perspective on working with startups: that you “give, give, give” and you have to “be willing to do that for a long time.”
David Cohen asked John, “At what point do you need to see some payback from that giving?” You should really listen to hear his whole, fascinating answer, but the short version is: You keep giving.
John recently moved into a new role as President of SVB Capital, with $4.5 billion under management, and he’ll be supporting entrepreneurs and startups at their earliest stages. John and David talk about what this new role means for him and for entrepreneurs. And they get into how John’s mentor at SVB helped him grow into an executive, and how John is paying it forward by mentoring women and other POC. He describes himself as “first generation Mexican American from immigrant parents”—and his life experience has contributed strongly to making him the Give First person that he is.
Companies and resources mentioned in this podcast:
- Give and Take, by Adam Grant
- Adam Grant
- David Hornik
- Abraham Lincoln
- The Lobby Conferences
- Meals on Wheels San Francisco
- Silicon Valley Bank
Edited highlights from the conversation:
Can you give too much?
David: One of the things I’ve heard you tell your team is: Guys, it’s give, give, give, expect it to be two or three years of give, give, give before you ever get anything back. It’s not quid pro quo. It’s be willing to do that for a long time.
How do you know that that’s paying off, or when you decide that maybe you’ve given too much? Adam Grant in his book talks about, there’s some people that’ll just take, take, take on the other side of that. So at what point do you need to see some payback from that giving?
John: You know, it’s a really interesting question. I’m very inspired by Adam Grant. I’ve had a chance to meet him and spend time with him thanks to David Hornik and his Lobby Conference. And I’ve actually asked him that question. I’ve actually pondered this idea of a world of takers, matchers, and givers. Can givers long term win? Certainly Adam Grant’s work proves that givers do win in the long haul.
I’ve thought a lot about this, and from where I sit, I don’t know how you eventually ask for something. I think if you are in a giving mindset and it’s an authentic voice within you to give, I’m not sure you ever really need to ask.
Certainly the way we measure, if you want to get technical, is we do look for what we call client advocacy. I know this is something you care about deeply, David. We think that the best loudspeaker for our brand are the clients we serve. And so the way we long term measure our effectiveness is around client advocacy. And so again, I’ve often asked the question, is there a point where you’ve given too much? And I actually think the answer’s no, I don’t think that you ever need to ask that question.
Advocating for Women and POC
John: You know, people always ask me, Why do you have such a commitment? As a first generation Mexican American from immigrant parents, for me, it’s simple.
Women form 50% of our society. And if they’re not getting advantages, or being disadvantaged, then certainly people of color have a lot worse chance. And so for me, it’s just a very rational way to look at the world. We’re not using the talents of half of our society.
Especially in our industry, David, where VCs generate less than 3% of the capital being raised by women. And then when you look at the entrepreneurs statistics, they’re just slightly better at under 10%. And so at my time of the bank and in my new role, I’m really excited to try to bring products that really support giving capital to women in both the GP side and on the entrepreneur side. I’ll be spending a great amount of my energy focused on: How do we go to the LP community and get them to commit funds to women GPs and women entrepreneurs? I think it’s a perfect time, and I really believe that from where Silicon Valley Bank sits, we sit at a unique place in the ecosystem where we get a chance to potentially debt the universe a bit. I’m really looking forward to that opportunity.
David: I see the same opportunity, we’ll talk more offline about that, but I see the coupling of that with these managing director roles that we have here at Techstars where you get 10 investments a year and you can build a portfolio of 50 companies in five years. It’s hard to do anywhere else, and it’s an apprenticeship model, you learn from doing. There might be something fun to collaborate on there as well.
Rapid fire round
David: First question. What give, give, give relationship, that you’ve had with a CEO, are you most proud of today?
John: There are several, of course, but for me it’s when a CEO is in a turnaround situation and you’ve been there in the worst of times, and you’re able to come out the other end, and you had to do some pretty difficult discussions with that CEO. But more importantly, you also had to restructure things and convince people on your side to do the same. When I think about the CEO relationships that are most meaningful, it’s the ones where we went through some really dark times together.
David: How about your favorite city in the world, someplace you think everybody should visit?
John: Well, I’ve had several. Paris, Paris always comes to mind, one, two, three. But I’m really falling in love with the North American cities. I think North America is underrated. And so I keep real track. So I’m gonna cheat and tell you that I look at Toronto, New York City, and Mexico City as three shining examples of cities that are really taking on more prominence in the world ahead of us.
David: John, is there a charity that you might be involved with that you would urge people to take a look at, and why?
John: Yeah. You know, I just joined the board of Meals on Wheels San Francisco. I’ve been part of Meals on Wheels for many, many years. But I love causes where we can solve the problem, where we can see the solution, the light at the end of the tunnel. And ending hunger for elderly people in San Francisco is something that we collectively can all solve. And so I’m very passionate, very committed to helping Meals on Wheels San Francisco achieve its goals.
David: Well as you know, you never know what you’re going to get back from Giving First. So we here at Techstars, we’ll make a donation to that one for you in your name, and also make one to the Techstars Foundation, which is focused on diversity and inclusion in entrepreneurship. Just a little thank you for being on the show.
John: Thank you. David.
David: Last question, rapid fire. The last question and I’ll let you go. Is there somebody, dead or alive, in history, it doesn’t matter who, that you would love to have dinner with and why?
John: The person who has inspired me over the years is Abraham Lincoln. Obviously I’ve read his books and the books about him. And I think about that point in the war, when it comes to civil rights and the choices he had to make to keep a tattered government together to fight, to do the right thing. He has always inspired me. When I’m put at my toughest challenges, will I rise to the occasion and do the right thing? And I am constantly inspired by his leadership and what he did to keep this country together at a time that it frankly wanted to break apart.
David: Great. John, on behalf of everybody at Techstars and everybody listening, thank you so much for all you do for startups and the startup community and all that SVB does. It’s noticed and appreciated, and thanks for being on the show with us today.
As a successful woman CTO, Sherri Hammons is well known for being both humble and strong. Her Oklahoma childhood taught her the importance of always giving (and how to get back on the bucking bronco). Give First is ingrained in Sherri’s leadership style and her approach to bringing together technology and sustainability, which is her focus as CTO of The Nature Conservancy.
Today, Sherri Hammons is CTO of The Nature Conservancy, but as she admits, “I took the nontraditional path to CTO land.” This path included eight years as a professional singer before she went back to college and got a degree in software engineering—and went on to work for companies big and small, as well as being CTO for the state of Colorado. She’s done for-profit, non-profit, and government—and brought technology, strategy, and humane leadership to each role.
Sue Heilbronner, CEO of MergeLane, described Sherri as a “humble badass”—a phrase that host Brad Feld loves. Sherri credits her humbleness to her parents, who taught her to “always give and always be nice to everyone no matter what.” That’s right, Sherri learned to Give First from her family—and she has been guided by that advice throughout her career.
As for the “badass” part, she’s a successful woman CTO. Toughness and strength of character might as well be part of the job description. Sherri sees her upbringing as contributing to this element of her personality as well: “I grew up in Oklahoma, I grew up on a horse, on a farm. And so I know about getting bucked off a bronco and getting back up.”
Listen for Sherri’s take on:
How to be a great leader
“You just always show up when it matters.”
“If you’re in a leadership position, people look up to you always, 24 by 7 by 365, and you just have to remember that.”
And how important it is for leaders to stay humble, stay human, and keep their emotions in check.
How technology and sustainability intersect
“Leveraging artificial intelligence and machine learning practices to be able to decide where we can make the most change and protect the planet, in the best way possible, as quickly as possible.”
The Techstars Sustainability Accelerator is “brilliant, actually. It’s a great way to leverage entrepreneurial minds to help solve these big climate problems. … Allowing us to partner with these startups is amazing and transformational, not only for the startups, but for TNC.”
Plus, why Winston Churchill is the historical figure Sherri would most like to have dinner with.
Companies, people, and resources mentioned in this podcast:
- Winston Churchill
- Factfulness: Ten Reasons We’re Wrong About the World—and Why Things Are Better Than You Think by Hans Rosling
- Sue Heilbronner
- The Humane Society
- The Nature Conservancy
- Techstars Sustainability Accelerator, in partnership with The Nature Conservancy
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.
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.
From Google for Startups to Startup Weekend to Rise of the Rest and beyond, Mary Grove is passionate about community-driven change, and helping make it happen.
Mary Grove is passionate about community-driven change, and this theme has guided her entire career.
She joined Google when it had only 2000 employees, and by the time she left it was up to around 75,000. Over 14 years, she went from working on the IPO deal team to starting Google for Startups.
Google for Startups’ very first partner was Startup Weekend, which Mary helped to spread from a few dozen to 140 countries, vastly broadening its impact.
Today, she’s a partner at Rise of the Rest Seed Fund, the co-founder of Silicon North Stars, and on the Advisory Board for the Techstars Foundation.
Mary talks with Brad Feld about the joys of empowering entrepreneurs across the globe, and the transformations she has seen.
This is #GiveFirst at scale. We love it.
Companies, resources, and people mentioned in this podcast:
Becoming, by Michelle Obama
Be Fearless, by Jean Case
Google for Entrepreneurs – became Google for Startups
UP Global – acquired by Techstars
Edited highlights from the conversation:
Google for Startups, Startup Weekend, & Techstars
Brad: Let’s start off by hearing a story about how you ended up at Google working on Google for Entrepreneurs.
Mary: Sure. I had the great privilege of joining Google in 2004. I was coming out of Stanford on my way to law school, and I thought I would just pause for a year or so and take a job at what was then a small company called Google. I joined the legal team back in 2004, and I actually worked on the IPO deal team for my first year, which was a fascinating and wonderful experience, with the process of going public and really being part of a very fast growing organization.
When I joined Google, we were about 2000 people. When I left almost exactly a year ago, Google was about 75,000 people. So it was a great 14 year run where I learned a tremendous amount, and I’m super grateful for the experience.
Brad: Going from a startup of 2000 to 75,000 employees is quite a change.
Mary: It really was. And it was really remarkable, Brad, to watch our co-founders Larry Page and Sergey Brin on that journey and see how they were able to scale the culture.
As the organization scaled to be that large, I had the opportunity to travel to probably about 40 different countries to visit Google offices, and I was always so struck by the fact that each office had its local flavor and honored the local country, but really also had such a consistency of culture and spirit. I’m happy to talk more about some of those values, which are certainly core core lessons that I carry with me today.
Brad: You were at Google for a long time, but there was a shift in your role at some point from the operating business in the legal group to this new thing that got created called Google for Entrepreneurs. My guess is many of our listeners know what Google for Entrepreneurs is, but maybe talk about it for a few minutes, how it got started, and what your initial involvement was.
Mary: After my work on the IPO, we were a public company. I then spent the next six years as a part of a team called new business development, which was led by Megan Smith, one of Google’s most amazing leaders. I worked for her for six years and that team was really working on early stage product, business development, expansion into emerging markets. That’s where I truly fell in love with the company—certainly the culture, but also what was happening on the business and product side, particularly around access.
I spent a lot of time working on emerging markets and very emerging markets. We had a project called the bottom 20, which was looking at the twenty least connected countries in the world from an access and infrastructure perspective. We put together a cross functional Google team focused on how Google could help both from a Google Inc. perspective and also from a Google.org philanthropic perspective. I had the opportunity to spend time in places like Iraq, Afghanistan, Pakistan, Gaza, the West Bank. Really, through that journey, what was most exciting to me was the opportunity that entrepreneurship created in these markets.
Google could have a direct impact. If we could help fuel and foster startup communities, that would build a platform for true economic development locally and globally.
Fast forward to 2011. Our senior leadership team at Google recognized that so many teams across Google were dabbling in activities supporting startups, but there wasn’t a consolidated, proactive effort around this. I had the opportunity to give some thought to that, based on the work that I had been doing on Megan Smith’s team, and essentially pitch what became a new team.
That’s Google for Entrepreneurs, which today is called Google for Startups.
Essentially our mission was to bring the best of Google’s resources to accelerate the growth of startups and entrepreneurial ecosystems. That included our capital, our talent, our technology. That’s actually what led me to the journey to meeting Startup Weekend and ultimately Techstars. Google for Entrepreneurs was a really amazing part of my Google experience. Through that we partnered with about 60 organizations, who I really believe are best-in-class groups like Startup Grind, Startup Weekend, Techstars. You name the continent, we were able to be there supporting the greatest community leaders. And it was a great time.
Brad: Our first introduction was made by Mark Nager around Startup Weekend on some kind of video thing that we did together around 2011-ish talking about startup communities. I’m not 100% sure that’s right. But that’s what I kind of vaguely remember.
Mary: I think we did a Google hangout.
Brad: What are some of your recollections around those early experiences that you had with Startup Weekend and it’s evolution towards what ultimately became UP Global?
Mary: Startup Weekend has a truly dear place in my heart and my memory. We started Google for Entrepreneurs back in 2011, and immediately we believed that partnerships would be a fundamental part of the work. There would be some direct work that Google did in the field, but really the way to get scale and impact was by working with best-in-class partners.
The very first partnership we ever signed was with Startup Weekend in 2011. I had attended an early Startup Weekend a couple of years back when I lived in New York City. I was really, really impressed with the format, so I caught up with Mark Nager and told him that we just believed in the power of this 54 hour event format and the fact that it was all about community-driven change. Our partnership really was to enable Startup Weekend to take that model and expand it from a few dozen countries ultimately into 140 countries. That was important in Google for Entrepreneurs’ history, because we found a partner who so fully aligned with us from both a mission and an execution perspective. They assembled a fantastic board with really great talent, which is how I was connected to you—and the rest is history.
Brad: What was your first memory of Techstars and your first involvement with Techstars?
Mary: We got very involved with Startup Weekend, which ultimately became UP Global, as you mentioned. Then when UP Global and Techstars merged, our relationship only continued to grow from there. Through Google for Entrepreneurs, we expanded the partnership with Techstars to continue to support those programs, as well as additional work including the Techstars Foundation. I was very struck by the scale and the breadth of Techstars in terms of the geographic reach, the sector reach, and the consistent quality across the board, which I think is really, really hard to achieve at scale.
Another touch point I have now is in my new home city of Minneapolis, where this past year I served as a mentor in both programs here, both the Techstars Retail and the Techstars Farm to Fork accelerators. Those were really fantastic—to get to actually see a full program from start to finish, to meet every one of the companies and even follow up with them. I’m still in touch with some now in due diligence for investment opportunities, and that’s just from two of the programs. I continue to enjoy that relationship.
The third piece is that I am on the advisory board of the Techstars Foundation, which I just absolutely love. I think that’s the embodiment of the Gift First mantra, which Techstars has always had. Formalizing that in the form of a foundation that not only supports entrepreneurs directly, but supports the community leaders who enable them—there are so few groups out there that do that. I myself also run a nonprofit called Silicon North Stars, and I know firsthand that it can be hard to find organizations who actually fund the organizations doing the work. I really applaud Techstars for the foundation initiative.
Rapid Fire Round
Brad: What’s your favorite city in the world?
Mary: I would say New York City. I had the opportunity to live there for five years during my time at Google, and I just felt like it was an extraordinary melting pot of hopes and dreams, energy and electricity, and the exposure to so many different cultures. It’s not a city that I spend much time in these days, but it is very close to my heart and one that I deeply love.
Brad: Great. Second: an impactful book that you’ve read recently.
Mary: I’m just about to finish up Jean Case’s book Be Fearless, which is her newest release. We talk a lot about how to create a strong culture of entrepreneurship. I do believe that so much of it is the culture. By that I mean this lack of fear of failure, embracing this notion that it’s okay to put it out there, to iterate quickly, to get harsh feedback immediately, and to pick up and keep moving on. I really appreciate all of the stories that she weaves in. They’re very practical advice that is super helpful for any entrepreneur, but especially for those who are just starting out. It can be a daunting journey.
Brad: I read a prerelease of the book and I thought Jean did a fantastic job. I’d echo that recommendation: it’s inspirational as well as instructive. Jean did a great job of not just curating the stories but also weaving her own experience through those stories. It’s a fun one.
Next up: favorite charity and why?
Mary: This is a very biased answer, and I’m not sure if I’m allowed to self plug here, but the charity that is dearest to my heart is a nonprofit called Silicon North Stars, which my husband Steve and I started together in 2013. At the time we were both living in Silicon Valley and working at Google. We recently moved to Minnesota. Steve is from here originally. I was born in Iowa and we both have a ton of family here in the Midwest. We started to look at Silicon North Stars as a way to really build a bridge from the communities we were from to where we lived. Our mission is to inspire and educate young Minnesotans towards futures in tech. We specifically target economically underserved youth. Every year we choose a cohort of a couple of dozen rising ninth graders and we take them on a trip to Silicon Valley for a week, expose them to all the magic there, come back to Minnesota, and then provide them with year-round programming and support for the next four years of high school until they start college.
This was a personal passion project. We bootstrapped it because we were both very privileged to come from entrepreneurial families, who to me embody the American dream. We wanted to give others that opportunity as well. We’re very grateful that the organization has scaled. Now we’re back in Minnesota, so we’re actually expanding the program for 2019. I should mention, Brad, that Techstars has been hugely helpful locally.
Brad: Homestretch. Last question. Who is a person that you’ve never met—either alive or dead—who you’d love to have dinner with?
Mary: I would say Michelle Obama. I’ve also just finished reading Becoming, her memoir, and I have always been a huge fan of the causes that she advocates for. I would love to have the opportunity to dine with her and to really pick her brain on how to apply some of those themes to our daily work and our daily life.