Strong mentorship was essential to Kesha Cash’s journey to becoming an impact investor. Her mentors Gave First to help her—and now she’s Giving First to diverse entrepreneurs through her Impact America Fund.
Kesha Cash founded Impact America Fund in 2013 with a goal of investing in software and tech enabled companies that have a positive benefit on underserved communities in America. In 2018, she was named one of Fast Company’s 100 Most Creative People in Business.
She went to Columbia Business School knowing that she wanted to start a fund that invested in diverse entrepreneurs, and it was there that she met Josh Mailman, founder of Serious Change, who became her mentor.
As an impact investor, Kesha Gives First every day. But she got to where she is today because of others, especially Josh, Giving First to her—empowering her, teaching her, mentoring her, and ultimately encouraging her to go out and start her own fund.
Companies and resources mentioned in this podcast:
Serious Change LP
The Wisdom of Finance: Discovering Humanity in the World of Risk and Return, by Mihir A. Desai
Edited highlights from the conversation:
The best mentor relationships become two way
Kesha: I had the opportunity to meet Josh Mailman [founder of Serious Change] at Columbia Business School. His family endowed the Mailman School of Public Health at Columbia and I started to work with him during my last semester at Columbia Business School.
This was, gosh, this was in 2010. I’d never met an angel investor that was interested in mission driven companies. I met Josh and Josh was a 60 year old at the time, you know, and a Jewish white man. We had this meeting and he expressed a sincere interest in moving more dollars into mission driven entrepreneurs of color based in the U.S., so we connected in many ways around that mission and I started to work with him. I volunteered during my last semester to identify companies that would fit the thesis of Serious Change. More specifically we were looking for entrepreneurs of color, and we made a number of investments together. What started out as a semester of volunteering ended up being a three year initiative within Serious Change to identify more of these companies.
Rod [Robinson, founder of ConnXus] was one of the investments that Josh and I made together. ConnXus was one of the investments that turned on the light bulb for me in regards to this thesis of there are tech solutions out there that can address inequities within systems. In the case of ConnXus, really looking at diversity and small businesses and the relationship with supply chains at large corporations is obviously very exciting. That early investment in Rod at ConnXus and a few other entrepreneurs that were using technology solutions became the thesis for Impact America Fund One. I was thankful for the continuous support by Josh Mailman and Serious Change. So that family office created space for me to learn, to grow my network, and to refine my thesis for Impact America Fund.
David: It sounds a bit like Josh was somewhat of a mentor, but like the best mentor relationships, they become two way, and I’m going to guess he’s learned a lot from you over the years as well.
The godfather of impact investing
David: Rod said it’s super clear to him that Josh, who he viewed as a pioneer of impact investing, has probably passed on a lot of knowledge and expertise to you. Talk about a little bit about that relationship that you have with Josh and maybe some things that you’ve learned from him or that he’s learned from you over the years.
Kesha: I call Josh the godfather of impact investing. He’s been at this for a very long time, before the term was sexy. We’re certainly happy that it’s a mainstream term now, but Josh and friends started this work over 30 years ago. He’s one of the cofounders of the Social Venture Network, of Investors’ Circles. It was really Josh and his colleagues, including folks like Ben and Jerry’s back in the day, saying, hey, there’s a better way to build businesses. There are ways for us to move our money that are good for society. I’m really blessed that I had the opportunity to meet Josh and work directly with someone. I learned from the godfather of impact investing about building this ecosystem and being catalytic.
Before I met Josh, I met people that knew Josh. They’re like, Josh is this radical, you know, in the best of ways. As an angel investor, he’ll sit down with someone, he’ll hear their idea and write them a check.
What I learned about Josh is that there’s a lot of thought process in writing that check. He’s really good at tapping into someone’s intentions. And we don’t always get it right, but I would say Josh has a gift for understanding the intentionality around a founder’s mission or business idea. What I’ve learned through him is that while that intentionality is extremely important in traditional business, I would say it’s even more so in impact investing. Understanding the founder’s intentionality and their reasoning for wanting to wake up every day to do this is truly important. That’s one of the many things that Josh taught me.
He’d ask me after meetings: do you think this person’s a good person? Which is a loaded statement for him because there are nuances as to what we mean by a quote unquote good person. He’s just good with people and understanding human nature.
He’s also extremely good at networking. He knows everyone across different industries. He taught me the importance of showing up at an event. Don’t talk to people you already know—you’re here to network and to do that in different spaces. When we worked in New York, we’d take trips to Harlem to visit an entrepreneur or go downtown, and it was just amazing to watch him be able to adapt to different environments and to really be present in those environments to understand what was happening from a cultural standpoint. I learned a lot from Josh about people and being present and truly understanding the atmosphere that we were in.
As for what he learned from me, you’d have to ask him about that. But he continues to be a great friend and mentor and I’m very honored to have him in my life as a mentor and as a guide through this process.
Go out and do it on your own
David: It sounded like Josh was a big proponent or fan of you launching off on your own with your next fund and activity that you’re doing now. Why would he support that? It sounded like he was a big fan of: Go out and do it on your own.
Kesha: That’s a great question. We met in 2010. After Wall Street and prior to Columbia Business School, I worked with very small lifestyle types of businesses in Los Angeles. The majority of those companies were led by entrepreneurs of color. That’s where I discovered this amazing talent that was disconnected from resources, and I applied to Columbia Business School with this idea of supporting and helping to build this ecosystem and getting more resources to diverse entrepreneurs. Right.
When I met Josh, I told him that I applied to business school with this idea. My business school essay said I wanted to raise $3 million to invest in these early stage companies. So when I met Josh, he’s like, Look, you know, you don’t have a track record. It’s gonna be really difficult for you to actually raise a fund. At this point, work with me. I have the capital, we can do deals. You go and find those deals, we’ll build it and they’ll come. The good thing about Josh Mailman is that he takes action. He’s catalytic, he takes action, he’s spent years trying to figure this out with me.
So we met and he understood my purpose and intentionality and we got to work. What started out as a, hey, come work with me for a year to identify some investments to do some deals, turned into a three year partnership at Serious Change. We got to the point where I said, Hey, I think I’m ready to create this independent fund, and he and Serious Change supported that. From our initial meeting, there was the intent that I would at some point spin off and raise an independent fund. And he held true to our handshake agreement. I’m thankful for that.
David: I mean, that’s a classic example of Give First. Knowing that he was going to train you up and then lose you—but that in another way he would get back from it because you would be carrying some of that business philosophy out into the world. Maybe even improving it a little bit.
The bottom line for impact investing
David: Any time I talk to someone who identifies as an impact investor, I like to throw out some data that we have here at Techstars, and you’ll probably identify with this.
We now have the Techstars Impact Accelerator down in Texas. We work with the Nature Conservancy. We have a farm to fork program. So we are doing more and more in quote unquote the space. As we did that, we really looked at the definitions of what we are looking for in those programs and found that 15% to 20% of what we’ve been doing all along falls pretty cleanly into this category of impact. And we pulled that cohort out. We’re investors in about 2,000 companies. So we’re talking a couple of hundred companies, maybe 200-300 companies that would meet this impact definition. And as a cohort they were performing better than the total cohort of all companies. So impact is not just about that second bottom line. It’s also about that first bottom line. And I’m sure you would agree.
Kesha: That’s true.
Rapid Fire Round
David: What’s your favorite city everybody should visit?
Kesha: New York City
David: Awesome. That’s a popular one. I think everybody wants to go there if they haven’t been there. I know why.
Kesha: I’m taking a red eye there tonight, so it’s top of mind.
David: You’ll be nice and rested tomorrow, I’m sure. How about a great book that you’ve read recently that you want people to know about?
Kesha: Oh, I’m almost finished with it. It’s called The Wisdom of Finance.
David: Any charities that you’d urge people to get involved with or take a look at?
Kesha: The Sponsors for Educational Opportunity. I participated in this organization while in college and was placed in my Wall Street position, and I think they are single handedly responsible for diversifying Wall Street. I encourage everyone to support them.
David: That’s awesome. As a thank you for being on the show, we’re going to do a donation to them, and also do one to the Techstars Foundation, which is focused on diversity and inclusion in tech, in your name, if that’s okay.
Kesha: Oh, excellent. Thank you. That’s wonderful.
David: We appreciate you coming on the show. Last one. If you have, if you could have dinner with anyone, they don’t have to be alive, who would it be?
David: It’s more fun if they’re alive. But let’s imagine that you could do it at any point in history is what I mean by that.
Kesha: Given the times that we’re in right now, I want to go back and be part of the conversations with some of our great civil rights leaders. Malcolm, Martin, some of the philosophers, I’m kind of going back a little further. W.E.B. Dubois. I think we’re in cycles. You can obviously read the books, but to be able to sit down and understand the philosophy and the lessons learned from different eras in time, I think would be extremely helpful right now.
David: That’s a whole party. I’ll give it to you. We’re looking for one person, but you can have a party. That’s cool.
Kesha, thanks so much for taking the time to join us on Give First. Best of luck with Impact America. Really appreciate you joining us today.
Kesha: Thank you, David, for all that you do as well.