Founded On Purpose

Kt McBratney: [00:00:00] Welcome to Founded on Purpose, the show where we get to know the people working to align business and impact, profit, and purpose. I'm your host, Kt McBratney. Each episode, we welcome a founder, investor, or ecosystem builder to answer the same set of questions. While the questions are the same, the conversations and the insights they open up are incredibly different and wonderful, and today's guest is no stranger to asking hard questions and finding opportunities that others miss.

Gayle Jennings O'Byrne is the CEO of Wokstar, an early stage investment fund focused on tech innovation brought to market by diverse, inclusive teams and women of color. She's a passionate advocate for investing in the green economy as a business opportunity, and she has incredible hat game. Gayla, welcome to the show!

Gayle Jennings-O'Byrne: Hey Kt, thank you so much for having me on. I just am a big fan of yours and so excited to be here on the other side of the microphone. Thank you for having me.

Kt McBratney: This is gonna be fun. I already knew it the second we [00:01:00] booked you, um, and I'm glad that we can share this with other people because while I would love to just, like, have conversation with you all day long, it's It's so much richer when we can share it with so many smart and thoughtful people out there.

Gayle Jennings-O'Byrne: I love that.

Kt McBratney: We're going to start with question one, the same place we start with everyone. In one word, what's your purpose? Demonstrate. It's a verb. I love that. Tell us more. How'd you come to that word? What does demonstrate mean to you?

Gayle Jennings-O'Byrne: Um, I got there because I think of what we do in terms of how we champion for women, how we invest in women, how we mobilize allies, men and women, um, how we're seeking like really cool technologies.

And so, I feel like we're just still in a place in this country, this world, this society where we still have to demonstrate the cool [00:02:00] awesomeness. Of, um, women, of inclusive teams, of new technologies. And so, yeah, demonstrate just sort of came to mind for me.

Kt McBratney: I really appreciate how that's such an active word, too.

You have, you can't passively demonstrate something. It makes me think of the, the writing, uh, adage, show don't tell.

Gayle Jennings-O'Byrne: You can't

Kt McBratney: just say that you're doing something. You have to do the work.

Gayle Jennings-O'Byrne: Yeah, you know, it really came to bear when we were raising the funds. I had, you know, beautiful deck, beautiful story, worked at J.

P. Morgan 20 some years, investment banker, doing auditions, Ivy League, right? So, thinking, yeah, like I can go raise the funds. It's gonna be amazing. We're gonna like do some really cool stuff and return some amazing capital to our investors. And then you keep hitting walls, and you keep hitting walls that say no on [00:03:00] them.

And I had to change how I talked about what we were doing. One, I had to just start investing. So, uh, it was like the day after New Year's Eve, or the day after New Year's Day, the banks are open. I call my bank and I was like, Hey, sell some of my JP Morgan stock, take some of my money on my savings, put it in the Walkstar fund, and then wire it to these companies.

I was like, it was literally that, that, um, not easy, but, uh, it was that direct of like, I just need to start investing and showing people what we're going to do. But the demonstrate part came when I said, you know what, I got to stop telling people what we're going to invest in and I got to show them, I got to demonstrate.

So I would go into meetings and the first thing I would say is, hey, pull out your phone. When people would pull out their phone. And I'd be like, can you tell who called you? Who was your, who was your last phone call? And they'd be like, yeah. And I was like, um, hey, do you ever watch like Law Order? And you know how they're always going to like the CCTV or the security camera?

And they're [00:04:00] like, yeah. I was like, I know, right? And then they'd be like, Hey, did you press the button to get like the flight attendant's attention any time this last year on a plane? And they're like, yeah. And they're kind of now going like, where are you going with all this? And I was like, those are all inventions by a black woman.

And they'd be like, what? And I'd say, so imagine if we didn't have those, if those things didn't get developed and built and scaled and market penetration. I was like, I'm looking for the next cool products like that. And I think it fits in my sisterhood. And I was like, so now let me tell you about what I'm doing.

And it totally changed the conversation, but it was the demonstration that was needed to get to that aha moment before people would sort of really take me.

Kt McBratney: That's so powerful. And being able to recognize that opportunity to give people tangible examples that they've used countless times and then make it, it feels like it, by demonstrating, it makes things real.[00:05:00]

For folks and relatable.

Gayle Jennings-O'Byrne: Yeah. Yeah. And I bet people probably thought it was gonna that my word was gonna be impact It's so not I mean i'm a capitalist I spent 20 some years on Wall Street. I like money. I like success. I like returns. Like, I mean, I can't not be impactful. I'm a black woman in America.

Like, I wake up and hopefully everything I do has some impact to it. But, um, no, I'm about the Benjamins and success. And You know, all boats rising, so, yeah, I'm sure someone thought my word was going to be impact, but it's not.

Kt McBratney: Good, I love a surprise. That's why, that's why it's the first question, right?

Because it kind of gives us this anchoring point. Sometimes folks surprise themselves with the answers, or they'll say, My team probably doesn't know this, but And it, it level sets, um, which I, which I appreciate. And also naming that, there is money to be made investing [00:06:00] in black women, and Women in so many different, uh, founders who don't necessarily pattern match a certain pattern that gets the vast majority of venture capital.

It's in the name, it's in the title venture capitalist, right? The, the, we, our responsibility in our job is to generate returns. And how we do it, right? That philosophy, the ethos, the thesis can also do other things can have impact. Why not both? That's kind of my, my thought is like. I'm a yes and person. Um, and I know you have some, some theater experience as well.

Gayle Jennings-O'Byrne: Um, but I invest.

You, you actually work with, with theaters. I just invest in them. It's,

Kt McBratney: I, I bet every actor, writer, director is like, oh, investment definitely counts.

Gayle Jennings-O'Byrne: I love it. But you know, there's [00:07:00] something that you said, and I just want to make sure that we don't miss the mark on, which is The investing that we do comes from a place of just being inclusive and being female forward and realizing that it is a competitive advantage.

So we're not exclusive. Uh, you know, we're not not for men. We're not not for the bros. But it's more like, are we getting the best representation and inclusive excellence that will then help drive success for these companies?

Kt McBratney: I love that. Inclusion as a competitive advantage. You should put that on a mug.

Gayle Jennings-O'Byrne: Oh my god, that's so funny you say that because I've been so into mugs lately. I think maybe because it's cold outside, I just want like some nice hot drinks. I was going to say a hot toddy. I just want some hot drinks.

Kt McBratney: No judgment here.

Gayle Jennings-O'Byrne: So I'm all about the mug these days.

Kt McBratney: There you go. There you go. New merch idea.

It's hot in more ways than one. The beverage and the statement. [00:08:00]

Gayle Jennings-O'Byrne: We do have a walk star mug on our account. I don't think anyone's ever bought one. Maybe my mom did. Yeah, we do have some

Kt McBratney: merch. You know, folks, this is your moment. This is your moment. Put your mug where your mouth is.

Gayle Jennings-O'Byrne: My mug moment. I love it.

Kt McBratney: I'm curious. You had such a track record in your career of successes and moving into the venture space. Um, I'm curious what your most recent win has been.

Gayle Jennings-O'Byrne: Oh my God, so that is so easy to tell you, which is one of the portfolio companies in our fund was, uh, acquired by Experian. So this company Audigent was bought by Experian, yes, and because of that exit, um, we were able to return.

All of the capital that our LPs, i. e. our investors, have invested and entrusted with us, and then return a little [00:09:00] bit more to them. So, 60 percent of our fund has been returned because of this one exit.

Kt McBratney: That's incredible. Congratulations to you, to that team. That's a huge, I mean, that's the founder dream.

Gayle Jennings-O'Byrne: That's the investor

Kt McBratney: dream.

Gayle Jennings-O'Byrne: Yeah, listen, and we're still investing. So this happened to our, during our investment period. Because you know, typically, You raise a fund, you have a couple years, four years to invest, and then you've got four or five years where you're harvesting and hoping to get exits and return capital.

We're still investing and yet we're returning capital. So my last 10 days have literally been on the phone with JPMorgan Chase and my banker and Carta, uh, getting these wires out to our. Investors. That's incredible. It's been beautiful. And like, one of them wanted to understand about the distribution of the tax, and she had her husband and her two [00:10:00] daughters, and I just walked them through it, and it was this beautiful, like, ability to show second generation about wealth creation through investing in.

Kt McBratney: Congratulations. That's huge. And there's a, there's a couple of threads in there, right? Like the fact that you're still in your investment period and have returned 60 percent of the fund that challenges this, this idea of the power law where. You know, 98 percent of your outcome needs to come from 2%, right?

And, I mean, I'm just like what you're

Gayle Jennings-O'Byrne: saying and I'm, I'm not validating it. Yeah,

Kt McBratney: right. And then also this idea of inviting more people to participate in the, in the wealth generation in this asset class, right? And making sure we're doing our best to make sure that the LP base, the investor base in venture.

is inclusive as well as the [00:11:00] founders that will be back.

Gayle Jennings-O'Byrne: That's right, that's right. Yeah, we were very intentional, um, you know, I had to sort of, not fight, but I sort of had to push back on my, um, legal team when we were forming the fund. And even my board about, like, where we were going to go, um, start our funding.

You know, because everyone wants the Pension funds and the endowments and the institutional investors. So, you know, we were even sort of wrestling with the minimum that people could invest. And I said, hey listen, if we get a woman who's never been in this asset class before, who's interested in being in it, if she comes in with a dollar, I'm going to help make that work I want her to have exposure to this.

It's all about access. And so, yeah, I mean, we don't have anyone for a dollar, um, but we have some smaller investors, and I gotta tell you, I love our investors. We have someone who is a dairy [00:12:00] farmer, we have a couple who are both doctors, I mean, we, we have retirees, um, we have people that are in my neighborhood, so, you know, listen, I don't think I ever want to show up and do something embarrassing, but there's this, I was feeling like I could be in a grocery store and my investors in the line behind me at Whole Foods or, you know, at the drugstore.

Um, so there's this sense of responsibility that looks different than just fiduciary responsibility. Um, because there's faces and there's names and there's stories. And again, there's that neighbor two blocks, you know, down from my apartment. Um, that. Really makes this, um, intentional about who gets to be at the table.

And I don't forget that because of those people that are sitting around the dining table with me.

Kt McBratney: We've talked about [00:13:00] some of these missed opportunities, right? Including what you just shared about the opportunity to have an inclusive investor base. Um, investing in black women. All of these things. What would you say is the biggest missed opportunity in the field?

Gayle Jennings-O'Byrne: I think it's just that. I think it's Recognizing that allies and investors can come from all walks of life. And so, even as I think about helping our founders raise capital for their next rounds, and as we think about maybe having fun too, um, I'm thinking about the investor base being more inclusive. And so, do I spend my time trying to get to sovereign wealth funds and getting more institutional, or do I really Do what I say about inclusiveness and be able to find those folks in the Midwest [00:14:00] who would love to be a part of it.

Find those folks in small town America, those flyover places. Um, that to me gets exciting. That's the best opportunity is that we're not allowing more people to experience what I believe is truly a way towards generational wealth.

Kt McBratney: I've been thinking recently of this this idea of creating more surface area for opportunities to happen and my belief and and a hill I will die on is that I community is at the heart of it.

It's human connection. It's really it's not transactions. And that's such a beautiful example of that of saying, like, how are we creating access? How are we inviting participation? How are we being intentional instead of treating investors strategy fundraising kind of like boxes to tick? Or, like, line items on a spreadsheet, which I think is an easy, an easy, uh, [00:15:00] pattern to get into because we're all so busy, the world is demanding, it's not going to slow down or get any less noisy anytime soon, and, and just having those moments to say, wait, what am I trying to achieve here, and how is it aligned with, with my purpose?

Can I, can I do better? And sometimes the answer is no, and sometimes the answer is, what if you tried this?

Gayle Jennings-O'Byrne: Yeah, the other thing we, you're absolutely right, the other thing we talk about with, um, our sisterhood, our ecosystem, is, um, being intentional with your purchasing power. Um, you know, when I started this company, It was my savings, right?

I was leaving my job at J. P. Morgan, and I said to my husband, Hey, here's our balance sheet, I'm going to take this percentage of it and get this company started. Um, I promise you we will not go into foreclosure, we will not lose the co op roof over our head. And [00:16:00] I had to think about, as I was building the company, how I was using my purchasing power.

And so, I was like, I'm going to, um, hire those folks that share my mission and my value. Who's inclusive? So, our law firm, before we signed them, I was like, hey, I want to have a diverse team representing us. Now, I want the biggest and baddest law firm in Tech VC, but in that, I also want you to have a diverse team on my account.

Um, that trickles through every vendor. that I have hired. Our web designers, our bookkeeper, our insurance broker are two women, right? I mean, everywhere you look, um, up and down the company, um, we are being intentional about how we use our purchasing power. And so I say that to others, and I say, listen, maybe you're not in a position where you can invest.

But I know you bought some earrings last week, I know you're gonna buy some holiday [00:17:00] gifts, I know you're gonna be buying birthday gifts this year. Be intentional about where you buy and who you buy from. Um, that's another way you can start.

Kt McBratney: Yes, I, I'm extremely late to the game with this phrase. I learned it this morning, I will admit that, uh, but the phrase, and I will try, I think this is the direct quote, is, a budget is a moral document.

Gayle Jennings-O'Byrne: Oh, I'm late too, I never heard that.

Kt McBratney: Okay, well welcome because I'm the apparently the brand new member and it just it stuck with me I've been thinking about it all day. So I love how serendipitous this is that you brought that up because it's very true And also I think it's a good reminder, especially to the founders out there Investors are founders too.

They're running a business and they're they're they're you know, it's not like we're like Sitting with, sitting back on some leather chair being like, Oh, who shall I give millions of dollars to today? Like we're trying to make payroll. We're having to [00:18:00] make decisions on vendors, hiring teams, looking at the economics of our companies, all of, all of these things.

And I think I can say that, uh, moving from the founder and operator life to the VC world. has given me more empathy for, for, uh, investors. Because

Gayle Jennings-O'Byrne: Yeah, I'm glad to hear that. You know, it's funny, when you were, uh, doing your introduction, I was like, now, which one am I? Am I a founder? Am I an ecosystem builder?

Am I an investor? And I kind of thought, I'm all of those. Um, because I really did start with the idea of building a company of which venture investable dollars is a tool. Um, but it's only one tool in our toolbox. Um, so sometimes I push back on thinking of myself as a venture capitalist and think of myself more as an entrepreneur who's building this venture platform.

Kt McBratney: So cool. Yeah. Why not all three? Why [00:19:00] not tick all boxes? We contain, we can be multiple things at once. We are, I know, right? Yeah. I mean, I love

Gayle Jennings-O'Byrne: it. Yeah. I mean, our three pillars are to champion, which we do through, uh, it's called Walkstar Academy, so it's like championing training. And then we invest, and then we storytell.

We try to make really good stories out there about, uh, women and just people in general. So yeah, we can wear a couple of different fedoras.

Kt McBratney: What I'm thinking of as you're, as you're dropping these gems and you're sharing your experience and your journey, you could do an entire podcast about the things that you have done right and the lessons you have learned.

I'm wondering, what's something that you've Oh,

Gayle Jennings-O'Byrne: I love that you asked that. Uh, so we have this, um, well I have and my team just, uh, is kind of all out. Um, which is fess up to your fuck ups. I am always about guys, [00:20:00] fess up to your fuck ups. They're not fatal, just catch up to them and let's, you know, probably solve through them.

Kt McBratney: Um, yeah. Also love the alliteration. I'm a huge fan of alliteration, so.

Gayle Jennings-O'Byrne: Yeah, I mean, and they've made me stop and I think they might have used it on social once and they changed it to fess up to your FFs or something. But yeah, you know what the full wording is. Um, oh gosh, I make so many mistakes. Um, but A, I'm learning to laugh at them.

I'm learning to own them. And I'm learning to say them to my team, and, and practice what I, I preach. Um, let's see. One that happened recently was, we were working with someone, some group, and I was gonna help, and I thought, yeah, this is gonna be it, this is the one, this is the team, this [00:21:00] is our peeps. And there were some, probably some little things that, if I were, Um, but what happened was is I got so invested in, I don't know, like maybe some cost and ego and just, I just got too far down the path that I couldn't just say, Hey, you know what?

Maybe this isn't working. And I just kept trying, kept trying to make it work until finally part of the team I was like, yeah.

So lesson is a, for me was having more confidence. And that little voice, I was kind of pushing it to the side. Um, which is interesting because I have good judgment and I, I have confidence and I, you know, I sleep well at night. You know, I can make decisions and, you know, sleep well after having made them.[00:22:00]

Um, but what I realized is that it's, it's a muscle, like sometimes you can flex it, sometimes you gotta, you know, work and, you know, get in the gym with it. And, um, yeah, I, that muscle wasn't working in the way that it should, and I tried to be okay, and I was like, you know what, I, I missed that one.

Kt McBratney: And you're still here to tell the tale, right?

To your point, it wasn't fatal, like you learned. Life business moves on.

Gayle Jennings-O'Byrne: Yeah, and you know what? I I'm I am proud of is that We just had to have a conversation and I just had to be okay having a difficult conversation

But in doing so it turned out to be an okay conversation because they were like this isn't working either

Why did one of us raise our hands here? Um, and that is my pet peeve. Sorry, it's a big pet [00:23:00] peeve. I'm gonna say this to everybody who's listening. Like, just man up, woman up, and just have a conversation. Like, it's okay. Like, it could start out being a difficult conversation, but it doesn't have to end as a difficult one.

It's just like a combo. Like, I don't know, is ghosting still a word? I'm 55, so I'm probably

Kt McBratney: I think so. I used it. I used it this morning. I didn't see it, like, with

Gayle Jennings-O'Byrne: investors. Sorry, now I'm, like, disinventing, but, like, when we were fundraising Like people just wouldn't get back to you and they'd be like, dude, if I said no, just say no, like I'm a big girl Like and you know what and then I can move on you can move on You're not gonna get like a bunch of emails and like voicemails from me.

Like it's cool Like

Kt McBratney: I that there's there's nothing like that feeling of anticipating a hard conversation, and I think a lot of people prolong, and myself included, like I am not perfect, but you prolong that feeling when you avoid having the difficult conversation, and that feeling after [00:24:00] you've had it, even if it was uncomfortable, not what you wanted to happen, even if the outcome is less than perfect, You still feel better instead of having it hanging over your head or this, this limbo, right?

Like it's okay to be thoughtful and take your time making decisions, but like please don't ghost. Please don't ghost people. Just like close the loop. Say I need more time. Say I need more info. Say no. It's okay. Say something.

Gayle Jennings-O'Byrne: I would say that to the team when we're due diligencing and looking at companies and listen, if it's a no, let them know as soon as you know it's a no.

And if it's a yes, try to get to a yes quickly, and if you need time, let them know you need time. And I was like, people, entrepreneurs, founders will appreciate that. But like, everyone is so busy, so don't waste people's time. Don't have them hanging out wondering.

Kt McBratney: Yeah, or trying different angles when they might be doing everything right.

And I think something I, I, [00:25:00] uh, try, try to bring up and, you know, when we aren't deploying capital is like, I let founders know up front. Like, a founder's time is one of the most precious resources and it cannot be replenished in the same way other things can. You can get more AWS credits. You can, you know, you can raise money.

I'm not saying that that's easy or, you know, equally, um, accessible, but a founder's time is precious and all of our time is precious. So being able to just. Just let people know where you're at. We are on the anti we are the anti ghosting squad here, uh, representing today.

Gayle Jennings-O'Byrne: Here we

Kt McBratney: go. We talked about the difficult conversations and a lot of this job can be hard.

It can be very serious, right? Looking at term sheets, negotiations, having to tell people no, but also It can be really, really fun. There's also so much data that shows that creativity and play are good for our decision making, good for our health, all of that. I'm curious for [00:26:00] you, how do you play in this busy world that we live in?

And this, this position that you sit at as all three of a founder, investor, and ecosystem builder, what does play like look like for you? Uh, so cooking is my love language.

Gayle Jennings-O'Byrne: And my husband is the biggest beneficiary of that, uh, even more so when COVID happened. I should be laughing and saying COVID at the same time, in the same breath.

Um, but, you know, when we started sheltering in place, he was getting like, Three gourmet meals a day. Like, I would be getting ready to start a Zoom call and I would be like, Oh, I'll be right on, I just gotta take this frittata out of the oven. They'd be like, What? Like, Who's making a frittata? And then like, later in the day I was like, Yeah, I just made a cheddar broccoli soup.

And they're like, Okay, so frittata in the morning, cheddar broccoli soup. And now you're doing, like, these, like, homemade egg rolls for, like, this whole Asian meal, and I'm like, [00:27:00] yeah, right?

Kt McBratney: Um, it sounds like I'd love to come for dinner. No, I, I remember during the pandemic also doing a, uh, my company was a very community led product, and doing a community call while also, uh, like a virtual event while also making a potato leek soup, and everyone's, what are you doing?

And I'm like, this is a leek!

Gayle Jennings-O'Byrne: I love it. Uh, so yeah, so cooking is my love language. That is one way that I have fun. Um, I am active in terms of, like, golfing. I love biking. My husband and I, um, are city bike people. So, it's either BRRRR or city bikes. How we get around. Alright, subway people. Um, And probably something people wouldn't know unless I said it was puzzles.

Like

Kt McBratney: jigsaw puzzles or word puzzles?

Gayle Jennings-O'Byrne: No, jigsaw puzzles. Like, I go to Goodwill and we'll get like three or four puzzles. And then we'll finish them in like, I don't know, a couple weeks and we'll be back to drop those off and we'll get new ones. And I even said to [00:28:00] our local Goodwill, I was like, So what's the deal?

Because you guys just never have them. She goes, well, cause you and your husband are always here getting puzzles, and we just started, like, getting more of them. And I was like, oh, I didn't know that. Yeah. I do love a puzzle.

Kt McBratney: I have a kindergartner and a kitten, so our jigsaw puzzles have been in the closet for a bit because the, doing them is great.

It's just, we can't leave them out. Cause you talk about two steps forward, ten steps behind, and then you lose the puzzle pieces and I can't handle that. I'm like, that missing piece just drives me bonkers.

Gayle Jennings-O'Byrne: Yeah, so that's fun. That's fun for me.

Kt McBratney: Okay, I'm curious, as we're getting close, we only have two questions left.

This time is flying. I

Gayle Jennings-O'Byrne: know.

Kt McBratney: Hello! I know. Alright. What? Ugh. I'm like, how do I even frame this for you? How do you navigate taking advice? Right? You're doing something that has been done before in some ways, but you're [00:29:00] doing it differently. You're doing it with your own interpretation, your own values, your own spin and experience on it.

How do you navigate, what advice to let in, and what advice to just say thank you and let, let, like, let the universe have it back? I

Gayle Jennings-O'Byrne: like to pilot everything, right? I'm a beta girl, I'm a pilot girl, taste test. Um, so I will I don't take in all the advice. Um, some of it I'll act on. Others I will just taste test and pilot in my brain for a bit and middle around a bit.

Um, but I do try to take it all in. Um, the one thing though is I'm always trying to think about what's their agenda. And not in like a creepy like, the world's out to get me, but just sort of like where is this coming from? How do I Make sure this is a blessing [00:30:00] for what I'm involved with, um, and just, like, receive it for the goodness that I believe it's coming from.

Um, and if it doesn't feel good that way, then I'm also kind of like, Alright, let me kick this around, but, well, if that, if that kind of feeling comes up, then I'll, you know, I'm easier to let it go. But, the question you didn't ask before that is, Am I good at this? Asking for advice. And I'm practicing that.

Um, Cause sometimes I find I um am doing a lot of mentoring and not making space to be mentored. And so I'm trying to be, or this last year I'm trying to be more, um Deliberate, and calling on people, and asking them questions, and setting up time, and [00:31:00] be like, Hey, do you have, um, it's like a text, be like, Hey, do you have 15 minutes on Friday?

I just want to run something by you and get your thoughts. And, and, and doing those little

Kt McBratney: pop ups like that more often. I love that you frame that as a practice. It's another, it's another muscle we can all easily take small steps, right? To regularly get better at. Because you can never be perfect. That doesn't exist, but, ah.

Okay. We're rounding it out with the last question. What is the most challenging thing about your job and what is your favorite thing about what you do?

Gayle Jennings-O'Byrne: The most challenging is trying to do this at scale such that we can truly, truly impact, uh, use the word, um, um, but so that we can truly change systems and realities for founders and that I struggle with and think a lot about.[00:32:00]

So for instance, even that big exit that we had and, you know, returning capital to our investors, how do we scale that in a way that unlocks more people to get excited about? Um, fund managers that look like me, have backgrounds like me, experiences like me, um, to get excited about fund managers like me, and then founders, uh, that, you know, we're, um, that are part of our investment thesis.

So that's the challenge, and I haven't cracked that code, but that's the thing I think a lot about. And I think that's probably why we do things, um, in addition to just the investment way. Like, if I could get up every day and just, Be a venture capitalist, like I probably get a lot more sleep and I have so much dark circle than my eyes.

Um, but you know, we do the training, we have the Walk Star Academy where we're teaching entrepreneurs how to raise capital and how to tell their story because we want them to be successful, um, even if we're not able to [00:33:00] invest in them directly. Um, and then with Star Media, um, I want us to have a way that we can.

Get more stories out there, because I believe storytelling is the way that we connect as human beings and yeah, there's a lot of isms and You know, there's just a lot in the world right now But I think if we can really see each other as humans and as neighbors Um, and storytelling is the way to sort of see through that Um, I think a lot of the isms and problems and divisiveness that we have as a Society can start to be eliminated.

And so, um,

Kt McBratney: As humans, we created these problems. We can also solve them. That's right, that's right. So

Gayle Jennings-O'Byrne: yeah, so that's the challenge. It's how do we do this in a system, in a way that's addressing the systemic and the systems. Um, the fun part of this, or the joy, [00:34:00] comes from the people. Um, it comes from my team, so they can go work at Goldman, or, you know, BlackRock or Greencroft or, you know, you name it.

Um, and make triple what they're making here. Um, but they are like me, we're public servants to entrepreneurs. That's how I, you know, we interview people. Um, it's like, are you ready for public service? Like you've had corporate, you've had a finance, you know. Um, career and how you ready for public service at a VC place.

Um, so my joy comes from the people on my team and seeing their development. And then the joy of the founders and the investors. I know that sounds cheesy, but seeing someone manifest a dream or a vision that they had is so I mean, it's I mean, this is now I'm really going to do. Like, it's not like you're in the, in the The room when they're giving birth, but it is this like special moment [00:35:00] that they're letting you in on, right?

Like it's so it's really beautiful to be a part of that and for people let you in And then for me the investors because we have such different types of investors seeing them on this journey of like I invested because of Gala, and then you're like, No, now I'm going to invest it because I just friggin love, like, this technology and all of that cool stuff you're investing in.

Like, that's a beautiful arc to see, or just, you know, seeing, um, Others learning about this asset class has been really cool. And even like, you know, our institutionals, like, they weren't familiar with these entrepreneurs and the things that we're investing in. So seeing them get excited, like, wow, like, you're really doing this.

Like, you're succeeding at this. Like, this guy's cool.

Kt McBratney: It's almost magical and I, I know that I'm, I'm grateful to, to be a person who knows you and be in community with you because I truly think that that is, that is a huge I don't know, [00:36:00] superpower, turbocharge, whatever it is. I think that's the engine that is going to drive the systems change.

Um, and it requires us all to be doing it, all of us to be coming together. And, and that's the joy, is where people doing really, really hard things and also really, really freaking cool things. And,

Gayle Jennings-O'Byrne: the journey is amazing. Yeah, and you know, I, um, was amazed when I got into adventure how actually, inefficient the financial markets are in this category.

When you look at other parts of finance, from trading, to syndicated loans, to equity, um, the equity capital markets, not equity as an investment tool, um, and there's so much efficiency, right? You look at the stock exchange, there's so much efficiency in, in how those markets operate. And then you get to VC, and between the fundraising [00:37:00] and then the allocating, I mean, Girl Scouts make us look like, pretty freaking janky if you ask me, like, Talk about a well

Kt McBratney: oiled machine there.

Yeah!

Gayle Jennings-O'Byrne: Oh my god, I did just, I got, I ended up buying like four boxes just yesterday. You, uh, yeah, it's this, um, Yeah, yeah, I bought four boxes yesterday. They're good, man. Like, they got me. But venture capital, I mean, we, we have so much inefficiency. Like, none of us should be holding our heads up high. We gotta figure this out.

So that's one of the things I think a lot about. Um, and we'll get there. I'm gonna be a part of it. We'll get it done. But yeah, we gotta, we gotta make this market more efficient. How we pool capital and then how we allocate it.

Kt McBratney: One day, one deal. One founder at a time. This has been so, so lovely. I could stay and talk to you for like 17 hours for those who want to stay on your journey, want to connect, want to follow along with all the great work [00:38:00] you're doing, where can they find you on the internet?

How can they get involved with all that Walkstars is doing?

Gayle Jennings-O'Byrne: Yeah, I'll make it simple. Start at walkstar. com, our website. There you'll find our social handles. You'll find my social handles. Um, I do return all my emails. Um, you'll find me on LinkedIn. I'm, I'm kind of horrible at the DMs on LinkedIn, the messages, but I'm getting better at them.

Um, but start with our website, walkstar. com. And I would be remiss if I didn't tell to any founders out there that we have a course, uh, through Walkstar Academy. Uh, it is currently free to founders. Um, and we're teaching you how to raise capital and how to tell your story. And one of the most popular classes is what investors ask and what they're listening for.

And they're very different, and we're going to tell you all about it in class.

Kt McBratney: We will link to all of those in the show notes. Gayla, thank you so much. This is so fun, and I can't wait to see what What wins are still in store for you in 2025? [00:39:00]

Gayle Jennings-O'Byrne: Well, hopefully we'll be winning together.

Kt McBratney: Agree. I'm down.

Gayle Jennings-O'Byrne: All right, let's do it.

Thanks for having me.