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On today’s episode of Porch Talks, Melissa Bradley invites Philip Gaskin to her porch. Phillip Gaskin is the vice president of entrepreneurship at the Kauffman Foundation, a longtime ecosystem builder, cross-sector connector and leader.
Phillip shares how witnessing his father’s journey as an entrepreneur is the driving force behind the work that he does, the importance of listening to your community, and the fact that there IS enough room for all of us to win.

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0:00:13.3 S1: Welcome to Porch Talks. I’m Melissa Bradley, founder of 1863 Ventures and co-founder of New Majority Ventures. Here on Porch Talks, I sit down with veteran founders, CEOs, and entrepreneurs who are committed to creating wealth for the New Majority. These folks have years of firsthand in-the-trenches experience navigating a fast-growing entrepreneurial ecosystem. Here they break down the roadblocks and barriers that tested their resiliency and resolve and share the lessons they’ve learned through it all. Each and every talk will support the health, wealth, and well-being of the new majority entrepreneur. Undoubtedly, these people and their stories will inspire you on your journey from founder to CEO. 

Melissa Bradley: So I’m honored to be talking to Philip Gaskin, who is the vice president of entrepreneurship at the Kauffman Foundation, longtime ecosystem builder, spent time in LA, now in Kansas City through DC, and somebody that I’m honored to call a friend. That’s how I would describe you. How would you describe you?

0:01:19.9 Philip Gaskin: First, you forgot the Philadelphia piece. So I don’t want to tick off anybody from Philly. So the Philadelphia piece as well. I think a cross-sector connector and leader comes in there too, because in those cities that you mentioned, there’s been a number of different types of work in different fields and different sectors. And it’s the connecting of all of those to move things forward. That’s the spice I’d add into it there.

0:01:52.4 MB: And where are you moving things forward to? 

PG: To inclusive prosperity, financial stability, economic mobility, equity, all of those different things as it relates to, it’s not only lifting all boats, but lifting specific boats in order for the other boats to rise and so forth. It’s those things in mind and the right translation to use across those sectors of people and groups in order for there to be enough understanding so that things do move forward.

0:02:25.4 MB: Gotcha. Why is that important to you? 

PG: Well, as I look back, I sort of in a stage of life where I’m re-dreaming a lot right now and re-dreaming the dream that my father had way back when and watching him go through four years of frustration before he was able to get a first loan, start a business. And I tell the story that I didn’t know my dad was an entrepreneur until he died, and at the funeral, a man came up to me and said, ‘you know, your dad was a good man, he was a really good entrepreneur.’ And I looked at him like, what did you just call me? I had never even heard the word. The language wasn’t there. Right. But I look at the years of him being told he wasn’t good enough, the zip code we lived in, the credit score being a few points too low and the color of his skin and on and on and on. And I’m trying to make sure that no one goes through what I saw him go through for four years. And so that re-dreaming of his dream is to how do you remove all of those different types of barriers so that people get from dreaming to the thriving that they want to do.

0:03:31.8 MB: Yeah. You know, what do you think your father’s dream was for you?

0:03:36.2 PG: To do anything I wanted to do. And he always said, you can do anything you want to do, just put your mind to it. What he didn’t always tell me or did, and I couldn’t land it, which is why he’d always said, son, when you get older, you’ll figure it out, are the types of things that all came to me, filled in the blanks when I went to the Legacy Museum in Montgomery. Because my time in that museum, he was in my ear the entire time saying, see, this is what I was trying to tell you. See, this is what I try and tell you. He grew up during Jim Crow in rural North Carolina. It all came together for me and the things that he was trying to tell me would be in your way, but that you’ve got to overcome because you can do whatever you want to do. Again, back to the re-dreaming, he wasn’t able to do it all. Tried to pass on as much as he could to me. In our moment today, working in through those different sectors that we talked about is seeing how many people are still blocked. And so you wake up, I wake up every day, that’s the fire, that’s the fire, wanting to see in this lifetime as much as I can for others who are now some years behind me. And some years ahead of me as well.

0:04:46.9 MB: We’ve known each other for a long time. And you’ve always been in this area and focus around entrepreneurship. Why do you think entrepreneurship is important in building inclusive economies?

0:04:58.0 PG: So much of our economy and our existence is based on entrepreneurial thinking, which is survival. Because we’re talking about survival, thriving and surviving, right. And so it’s important for people to thrive and survive physically, emotionally, financially. And in the end, I mean, it’s a rather, if you want to use the word almost patriotic thing here, it is a sustaining the viability and the sustaining of the American economy. By realizing that the economies are local people being the new economies, you know, that’s not only out of my mouth, a lot of people say those words. What does that really, really mean? It’s by having entrepreneurial thought in order to do what you want to do. Right. And that could be whether you want to be an employee, or an employer, as we say in our in our work, I think the freedom that’s there, sense of freedom and entrepreneurship is very, very key for people. And we see what the country has grown to over its years through entrepreneurial thinking. Well, let’s get more people in able to do that. Right. And imagine what we could be.

0:06:04.6 MB: Yeah. Did you ever think about starting a business? Did you ever start a business?

0:06:07.0 PG: Number of times and I will tell you that it’s the transformational thinking I’ve had to do is not tying everything to my dad’s experience. Because you could look at that and say, Why on earth do I want to do that? Right. And, you know, because I’ll never forget the day because he got he got the first loan, a black owned bank, gave him finally trust, finally believe in him, never forget the day he said someone finally believed in me. But I don’t know if I ever want to go back after he did get a second loan, or third because I don’t know if I ever want to be told I’m not good enough again. He had had it. Wow. And so I’ve had to like transfer that out thinking into Yeah, go ahead and do and we got some ideas in my percolating in my head that could one day be there. But in the meantime, helping others do it.

0:06:55.6 MB: Yep. Which is very important. Right. 

0:07:01.6 PG: What was your dad’s business? Convenience stores, South Central LA. Because moving from they moved from North Carolina, my mom and dad moved from North Carolina to LA before it was born, which is why it wasn’t born in rural North Carolina. It was born in Los Angeles. Because back then it was seen as that new frontier for black people 

MB: Go west, 

PG: Go west. Yeah. And he and a  bunch of friends went west. Wow. And so into the area of LA, where it’s like, well, how you thinking, how do I service and give back to this community? Right? Well, convenience in the neighborhood. So his first store was just south of the LA Coliseum on Vermont. Oh, yeah. And second 54th in Arlington. And I when I go back to LA, I still drive by those corners. And it’s just comes to life for me as a redreaming of imagine if it was all still there. But so that’s what he did. He wanted to do some other things. You want to do some, some franchising entry into franchising too expensive. He wasn’t able to do it. Right. And other things. He was very creative mind. Very creative mind. But it was also at a time where, while there was that go west and that creative mind, there was also a lot of, you know, other forms of oppression that were going on there in the city at the time.

0:08:15.3 PG: Sure. That, which goes back to that thriving thing, getting out of other people, other circumstances, defining your place. Yep. And you define your own place. What he was transferring over to me was don’t let anyone define your place. And that is one thing I live every day.

0:08:35.2 MB: That’s awesome. What stands there now where the convenience stores were? 

PG:There’s one, there’s a Cleaners and the other a Bus Depot. 

MB: Oh, wow. Okay. 

PG: Transformation, transformation of things there. But yeah, and I think it’s been other things. I think that Cleaners was something else before. And when I was living, I’d go to a lot of football games. We’d be doing our tailgate and stuff. Everybody I’ll see in about an hour, I just walked down Vermont and just go to it. Oh, wow. See what it was, just to stand around and things like that. Try to bring it back in that moment and stuff. 

MB: Yeah, sure. What do you think the role of philanthropy is in this world of entrepreneurship? 

PG: Overall, it’s like, why was philanthropy created, right? Going back to the core things of what we do, e specially in our foundation is what are those root systemic issues that are in the way of people getting a good education, starting a business, economic independence, again, whether you want to be an employee or an employer. So we focus on, you know, prepared workforce and entrepreneur focused economic development, the two priorities. It is a an active seat at the table in solving problems.

0:09:51.3 PG: Right. And I believe that go back to my cross sector nature of that it’s philanthropic, nonprofit, government, corporate, all have roles in this moment in time, where, and the word transformation is used a lot. Yes. But there are some things that need to be transformed in order to get to a certain place in the future. And so the role and how you are as an organizational actor is incredibly important. Listening has never been more important to people in the communities that you are trying to serve. And the community organizer in me from that that time in life was, which never really goes away, thank goodness is you listen 70% of the time and you talk 30% if you’re out of that ratio the wrong way, you’re not listening to what people need, period. And that’s a good role of philanthropy and, and other actors in the in the in the ecosystems as you know, as it relates to entrepreneurship, but I rooted in community because it’s how well it all can start.

0:10:59.1 MB: You must be deeply dedicated to this because you left Los Angeles to go to Kansas City, Missouri. Talk about that transition to Kansas City.

0:11:08.1 S1: Well, it was by way of that was the by way of Philly. Okay. Okay. We had to stop. Okay. But I still did. So, re-dreaming because I’m a dreamer. So when I got the call from Ed Hunter, I’ll never forget. So the first the title of the role was, no since like director of Metro strategies or something like that. But it was the tagline, help create a new model of economic development in the United States fueled by entrepreneurship had me hook, line, sinker right that because it was I got to go do this. Because my career has been about growing and leading organizations and teams related to new frameworks are changing the order of things, right. And so when there’s a new framework or a new way of being, that’s the first thing that was there. But I’ll never forget the phone call. The headhunter said, well, I need to tell you this role is in Kansas City, Missouri. I said, great. Silence on the line. She Wow, he just said great. But it was like, because I doing that type of work with that type of message from the middle of the country where perhaps no one expects it’s becoming from.

0:12:18.3 PG: And looking at talking about how do we get to zero barriers? How do we get to the best prepared workforce? How do we get to entrepreneur focused economic development? And honestly, talking through the lens of demographics and geography and all that type of stuff? Yeah. What a moment. You know, and I felt that there’s and also it’s wanting to slow down after a lot of the coasts. I know. That’s really slow down. Yes. Right. So slow down, but speed up at the same time.

0:12:49.0 PG: Because I wake up with an urgency every day on the on the solving on the problem. So it was it was, I think had I not had the roots from rural North Carolina and all those summers that we would they mom and dad put us in the station wagon with the wood on the side. Wow. Classic, right? And spend in North Carolina or up in the East Northern, New Jersey where my mom is originally from. I may not I may not have had that pull against that was part there’s like, slow down and and go back and live a little bit of what your roots were, even though you weren’t born there. Also knowing the demographics would be very different from the coast. But again, there’s that cross sector nature and that translation and vibe or DNA that I have in me. I want to do that. Sure. So I get from people sometimes, you know, you would be a really good small town mayor because you just relate to everybody. 

MB:Is that next? 

PG:Don’t know about that. Okay, okay. Okay.

0:13:45.6 PG: Okay. Community, you know, communities do entrepreneurship and prepared workforce and things like that is like really important. That’s good.

0:13:54.3 S1: After the break, we back to talk more with Philip Gaskin. 

Welcome back. Here’s more of my conversation with our guest Philip Gaskin.

MB:Entrepreneurship some would argue, we’ve been doing this for a long time, right? It’s become a buzzword. Everybody thinks they can do it. Everybody wants to do it. What scares you about entrepreneurship and how it’s being used and developed right now?

0:14:20.5 PG: I’d say that it’s too binary. That you either win or lose, pass fail, become the next big thing or you’re not good. And that is not healthy, especially for a lot of young folks who may believe that unless I become that figure, I am therefore nothing and I have failed. That’s dangerous.

MB: What happened to your dad in terms of people saying him feeling like when I get a no, that means I’m not valuable.

0:14:48.5 PG: Exactly. Exactly. Exactly what happened to him. He stuck with it though. And then got to a point of satisfaction and then realized that some of the work and other things he needed to do and the money savings tried to put my sister and I through school and stuff like that came in as well. But I saw that how it stunted. And so it’s almost like a reliving of the word or redefinition, I guess, of the word of entrepreneurship, at least in the minds of folks that really understand that it could be. And it’s totally fine if we do start a business and it’s sole proprietorship. Or if you want to and if you employ two to three people, that’s success and that’s fine because they didn’t have jobs before.

0:15:34.9 MB: That’s right. Jobs, survival. There we go. Right. So I think that’s one of the things that I try to, we try to, in all this work, is to get people to understand that it’s not as binary, it’s not as pass fail. You know, it’s about financial stability, it’s about economic mobility, it’s about prosperity. So those different things, just framing it differently. Because those are also words that invite community, that invite collaboration, that invite more minds, rather than just linear A, B, boom, that’s what it is.

0:16:08.6 MB: That’s right. When you think about entrepreneurship in community, what are some ways that you’ve seen it has not done well by the community?

0:16:19.9 S1: Gravitating towards the shiny object. Gravitating towards, let’s make sure that our incubators or accelerators or whatever are all about one sector. Just tech, just this, whatever. And that is that, again, you’re sort of like classifying or almost commoditizing it when it’s not necessarily listening to all ideas that are there for what a business can be. 

MB: And allowing people to be fluid in that process. 

PG:To be fluid all the way through it. Yeah. And so that’s how I’ve seen it not necessarily be helpful. Gotcha. In communities. Goes back to the listening of, do the community leaders truly understand the assets in their community? And don’t try to make your community something else that you cannot be. Go off the gifts of what you have and maximize those. A lot of times the gifts are down every city block and just go door to door and find out. Imagine if you had in a community, students, community organizers, whatever, they go door to door and they ask three questions. What do you want for yourself? What do you want for your kids? What do you want for this neighborhood? Say those three things and watch what comes out.

0:17:36.0 PGTrack the data and to take it back. Because it’s the listening and that’s how you build community, is door to door. Is block by block. And understanding and uncovering the assets that you have right there.

0:17:49.9 MB:Do you think tech can enable that? 

0:17:52.3 S2: Of course Yeah. It goes from the clipboard and the sheet and the number two pencil. What did you just say? Tell me again please. My pencil just broke. To an app. An app. And you’ve seen some of those apps out there. But I think that intentional technology that is about just what we just talked about and is patient with that. That it doesn’t have to become the next best thing to turn into an IPO or something. But it’s purposeful. I think it can do that. And I think that going back to what we were talking about how entrepreneurship hasn’t really worked in communities is just not instantly compartmentalizing what seems like a non high-growth idea as a non high-growth idea instantly and just categorizing that and push it aside. 

MB:Push it aside. Yeah. 

PG:You just don’t know.

0:18:45.7 MB: Yeah. Right. Tell me about your sister.

0:18:48.4 PG: My sister is one of the most amazing human beings on earth and she won’t take credit for it. Follows in the footsteps of my mother I talked a lot about. So my mom was a special ed teacher. All the females in my mom’s side of the family, all teachers. Almost all of them teachers. Special ed, non special ed. So my mom was a special ed teacher and also area coordinator for California Special Olympics for 30 years. And my sister special ed speech pathology and audiology for special ed. And it took the mantle over from my mom when she passed in 2013 and is area coordinator for Special Olympics down in Southern California. And dedicated in service daily. We have a service gene throughout our throughout our family. And for everyone always a special eye to the underdog, to the underrepresented. But propping up the ones that are represented as well. But two amazing human beings, my mom and my sister. One of the hardest decisions I ever made was in 2011 when I got the call that said we want you to come to Philadelphia to work the the reelection. It was the time my mom’s health was starting to noticeably decline.

0:20:16.3 PG: And I remember when I got the call I was like really excited and within like three seconds I sunk and said how can I possibly do this? And had to go to my sister and just say what do you think and can you help me here type of thing. And she did. My mom didn’t understand it. I’ll never forget my mom saying why leave me now? That’s a hard one. That’s a hard one. And I also knew that it’s something I had to do in that moment. And it was tough. I left and the week after I leave my mom, congestive heart failure, couldn’t even talk to her for the whole summer, almost gave up and flew home. And my sister said just stick with it and see how it goes. And God better she never actually came out of hospital and homes after that. But it was my sister that really helped through that. And of course what also helped when I started sending mom pictures of me with Michelle. Oh don’t worry, just stay where you are.

0:21:22.1 MB: Right, right. Look at my son. Look at my son. That’s why Obama got elected. I’m glad she came around. Yeah, yeah.

0:21:32.6 PG: But sister, fabulous.

0:21:34.2 MB: What is your proudest personal moment? You’ve got a lot of accolades. You’re always speaking all across the country. But what’s your proudest personal moment?

0:21:42.5 PG: Last week it came to me and I said you keep forgetting it. And of course I forgot it right now. Because whenever anyone asks me that question I never remember it.

0:21:52.4 S1: Keep going. But it was literally just last week because it’s one of those questions. 

MB:We’ve got a lot. 

0:22:03.6 PG: I have a lot. But something really came to the front. And it was 2012 was one of them. Okay. Because getting the largest voter turnout, working with others to get the largest voter turnout in Philly history at the time. In 12 over 08.

0:22:15.3 PG: That was a feat. I will say because it was in that, in that work and in other work, it’s building things from scratch into organizations so that people do extraordinary things and thrive is the theme. And that’s been in my corporate, national and global work, local community organizing work and what we’re doing now with entrepreneurial communities and capital access and prepared workforce and entrepreneur focused economic development. I mean it’s there. But that’s certainly a theme. Yep. Because it’s selfless service. And a lot of leadership is leading from behind because you’re always in the front. You can’t tell if people are going in the right direction. You’ve got to be behind and see and help them along.

0:23:00.8 MB: Yeah. You’ ve done a lot. You’ve seen a lot. What do you think is right now the greatest obstacle for new majority entrepreneurs?

0:23:11.1 PG: Hope. Because in hope is, and whether hope’s there or not there, it’s not there is am I seen? Am I seen as viable? Am I connected? Am I understood? Am I listened to? Because I think we have some communication and understanding profound divides right now generationally and other ways in the country or perhaps on our earth. And that comes to mind first. I think that and focus and not being distracted by going back to what we were talking earlier about being distracted about something that might not either be in your reach in that moment but can be. But by that shiny object and being seen as not good enough if that’s something you don’t attain. And then not giving up and not losing hope if that doesn’t happen. You and I have talked about capital access and other things for so long. And it’s there because what was happening to my dad decades ago is still happening today. Different forms of red lining are still happening today. Different biases are still happening today. And where translation comes in is translating that is just so that people don’t see that as just naysaying not picking up all the other isms don’t pick up your picking up yourself by the bootstraps and all that.

0:24:41.3 PG: It’s still there, you know, and it’s gonna take a lot back to that cross sector work and all actors being at the table and understanding that it’s not as we’re not talking zero sum here. It’s not taking from others to give to others. There is enough. But access overall and those pillars that we have access to opportunity, funding, knowledge and support those four things. Right? And it’s, they’re more, sometimes they’re more invisible than visible. Right? Because they’re subliminal and they weigh on the mind. There’s that allostatic load mind of what is on young entrepreneurs of color. Others of whoa, this too.

0:25:22.5 MB: Yes, right. It’s a lot. Right?

0:25:24.2 PG: Yeah. And you’re going about your day and you don’t really understand that there’s that other existence on the other side of how good good can be because you’re in this all time. You know, this is just the way that it is, I guess. Trying to get to that other existence. Yep. Be excellent.

0:25:38.8 MB: Yeah. I want to thank you for joining me on the porch. Oh, thank you. You’ve been a huge partner, supporter of me and so many other folks in the ecosystem.

0:25:47.2 PG: Likewise. Thank you for what you do. And we are grateful. Thank you.

0:25:52.4 PG: Thank you for listening to my conversation with Philip Gaskin. The first call I made because that brother shows up no matter what. Oh yeah. And by the way, my man Phil, he did call to tell us his proudest personal moment.

0:26:05.8 PG: I will never forget what is my most proud and memorable moment of flying an airplane and doing it without that much training. So I took flying lessons and normally it takes anywhere. I think the earliest is 10 hours of training and lessons before doing a solo flight until up to 20 hours maybe or more. But I remember after my eighth hour of training, my instructor landed the plane, a Cessna 152 and said, you’re ready. So what are you talking about? I said, you’re ready to solo. You know how to do it. Jumped out of the plane and said, go solo. And so I soloed in a Cessna 152 out of Long Beach, California airport. I’ll never forget that as much as I love flying and being in the air. Every time I get on an airplane today, even if it’s hectic business travel or person, whatever it is, it’s still like that first day doing my solo flight.

0:27:10.4 S1: Porch Talks is a production of Kinetic Energy Entertainment and New Majority Ventures. 

Recording and video production services were provided by Modulus Studios. 

This podcast was recorded at the Blackjoy House in Oak Bluffs, Martha’s Vineyard. Our producer is Anne Kane. 

Our social media producer is Misako Envela

The show is mixed by Sonya Harris. 

The Porch Talks theme is a new view by Tony Cruise.

Thanks again for listening. See you back on the porch.

Melissa Bradley

Melissa Bradley

Melissa L. Bradley is the Founder and Managing Partner of 1863 Ventures, a business development program that accelerates New Majority entrepreneurs from high potential to high growth and Co-founder of New Majority Ventures, a purpose-driven media brand featuring content that is entertaining, inspirational and actionable so that these entrepreneurs and their businesses survive and thrive.