Syama Bunten: What if the future of investing looked less like a velvet rope and more like a group chat? Today I’m talking with Cheryl Kellond, the founder and CEO of Play Money, about opening the gates to angel investing, moving capital with conviction, and why the next wave of wealth creation might belong to the people bold enough to talk about money differently.

Women don’t talk about money the way we should. Not honestly, not openly, and not with each other. But that’s changing. I’m Syama Bunten, founder of Wealth Catalyst. And Getting Rich Together is where the conversation lives. Every week, a different woman, a different path, and a conversation that will change how you think about your own financial power. This community is growing and you belong in it.

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I am here with the badass Cheryl Kellond. She’s the CEO of Play Money, a serial founder, angel investor, and she is on a mission to revolutionize the angel economy by making startup investing inclusive, fun, and accessible. Cheryl, you have raised over $20 million in venture capital, no easy feat. Being such an incredible entrepreneur, you’ve also led nearly a billion dollars in product revenue. And along the way of building an illustrious career, you’ve also managed to find the time to coach hundreds of early stage founders. You are a crazy woman. I love you. Welcome to Getting Rich Together. Thank you for being here.

Cheryl Kellond: Woohoo. I am so excited to be here.

Syama Bunten: Well, let’s start from a young Cheryl. Maybe a Cheryl who didn’t always know she was going to change the world and be on a mission, or maybe she did know. Take me back to a young girl somewhere between the ages of seven and twelve years old. My love, where were you on this big, beautiful planet? And what was life like around you?

Cheryl Kellond: Oh my gosh. I don’t know if I’ve agreed I’ve changed the world yet. But if we’re going to seven to twelve year old me, all right, super top secret, I used to be really shy and insecure. I’m an introvert. No one who listens to this or has seen me anywhere would ever believe that, but I’m a big introvert. I used to be shy and insecure, so you would not have recognized younger me.

That said, we were always doing something sort of crafty and creative. I was the kid that was like, let’s play business, right? There was a party business, a little publishing business, we ran a racket in the neighborhood on our little Schwinns, and we did little neighborhood productions back in the day. So I was sort of that girl. But definitely not the ballsy, larger than life leader.

Syama Bunten: What kind of student were you? Were you quiet and into your books, or was it more like the quiet girl in the big group of friends? What was it like for you at school?

Cheryl Kellond: I always had a close posse of a few friends, but not a super big group. I wasn’t nerdy nerdy. I did a little bit of everything, but I was a super good student. I knew it, but I wasn’t the smarty girl. I was just sort of low key.

Syama Bunten: I love that. What neighborhood did you grow up in? What were the kids like around you? What were the homes like around you?

Cheryl Kellond: My goodness. I grew up in Fairfield County, Connecticut. So life did not suck. My parents came from a blue collar background, they were the first of their generation to go to college, so Fairfield County was a little bit of a stretch for them. They were the dorky Midwesterners who never quite fit in. I don’t think there was anything truly remarkable about it. It was upper middle class.

They moved when I was a senior in high school, which was pretty traumatic, and they felt pretty shitty about it. So I made them a bargain that if I had to leave my senior year, I was going to go somewhere sort of glam and fancy. So I went to Andover for my senior year before college. Again, my life did not suck. But by the time I got to high school, I was sort of the fun, rebellious type. We used to go to Greenwich Village on the train on the weekends and pretend we could dress sort of punk, even though we were too afraid to permanently dye our hair or shave everything too much.

Syama Bunten: What changed between being shy and then becoming punk rock rebellious? Was it just a maturation of time, or was it something specific, a magazine, a moment? What saw you through that transition?

Cheryl Kellond: That is a great question, because I’m not really sure. I don’t think it was one big magic moment. Maybe it’s like how some kids mature faster or slower, they get facial hair, they get moves. Maybe I just went faster on the trajectory of running out of fucks to give. And if you run out of fucks to give at a certain point, you just live a little bolder, live a little louder.

Maybe that’s it. I had a kid really early. I was on a podcast this morning and the host said, tell me about when you were in your twenties. I said, well, sweetheart, I was that girl in college who was pregnant out to here and had to graduate early, and then was carrying around a baby at the bars at twenty-one. That kind of stuff changes you. You learn to live a little different because you’re living in your own reality.

This coming weekend is my thirty year anniversary from grad school at MIT. I was the girl who rolled in with a four year old on her hip. I was like, great, we’re getting an MBA, and this is my friend Corey, and he’s going to ride a bike and play with cars in all of our meetings, let’s go. So maybe it was that.

Syama Bunten: Yeah, there’s definitely a sense of young self-directedness. I feel like growing up with proximity to a big city is a blessing and a curse. You get to see all the things. Having grown up in San Francisco, I remember being so immune to homeless people because it was just the way it was, you sort of develop a different appetite for life. So talk to me about university. What did you end up studying? How did you decide where to go? What did you know of yourself at that time?

Cheryl Kellond: Great question. Coming out of Andover, I went to University of Chicago, which again plays to the fact that I was the quiet shy girl growing up, not necessarily the best fit for me in college. It was academically intense, really hard, with its own quirks that everyone knows about. I paid a big chunk of my college expenses by being the late night waitress at the House of Tiki in the neighborhood. I worked the four PM to four AM shift. I lived with some friends from the neighborhood, I had moved out of the dorms, so I was well into carving my own path.

I finished school in about three and a half years. I got pregnant and had to graduate quickly. The defining moment there was actually being the late night waitress at the House of Tiki, which turned out to be very pivotal later in life. I graduated and got some job doing something, probably making about $24,000 a year, as a single mom. The economics on that weren’t really working out well. My life was blessed, I have a family that was financially supportive in the worst of times, but mostly they were just around to help me with my son.

There was a moment I was working in a building in Boston, my parents had moved there, and I moved back after having the baby for smart reasons. I used to be able to look out the window and see MIT. I thought, if I go back and get my MBA, I can pay for it with student loans for two years, and when I come out I won’t be making $24,000 anymore, I’ll be making more. This feels like a good idea financially, a way out of the strange situation I was in.

So I applied to MIT and got really good grades on the GMAT, because I was a good student, and I studied next to my son who was watching Barney the whole time. You can memorize and absorb facts easier if you’ve got a repetitive sound playing in the background, some kind of mnemonic. The Barney song was my mnemonic. I aced it, I missed one question on the whole test, sitting in that room for three hours hearing “I love you, you love me, we’re a happy family” in the background the whole time.

So I go into MIT for my interview, and I walk into the room, and the admissions officer sitting there just stops. He goes, “my god, I know you, you’re the waitress from the House of Tiki, I used to drink drinks out of your shoe.” I said, of course you are. Turns out he was the director of admissions at Booth Business School in Hyde Park, where the House of Tiki was, while I was there. There was no way I wasn’t getting in after that. This guy was ready to pour drinks out of his shoe for me right then. So from a mousy ten year old to the House of Tiki waitress getting into MIT Sloan, but there you have it.

Syama Bunten: I love that. When you made the decision to do your MBA, other than knowing it would significantly change your financial position, were there any other outcomes you had thought of at that time? Any ambition around wanting to create a thing or do a thing? How much of your future self had you tapped into then?

Cheryl Kellond: Oh no, no, no, no. My future self needed my current self to unwind the mess my current self had put myself in. I was not thinking that much about the future. I had this husband, this baby daddy husband who needed to be my ex-husband, and I needed a little more financial muscle to get out of it. So I wasn’t thinking five steps ahead, I was thinking two steps behind, but it was the same underlying person in the middle.

This is going to date me, but when I was at business school, the internet was new, it was the year the Netscape browser went public. When I was there, all that entrepreneurial stuff from when I was a little girl came into play. I went on the school trips out to California to meet with tech companies. I had a friend out there who worked at General Magic, and we said, let’s start this new internet thing where we tell stories. They call it a blog now, back then they called it an “e-zine.” We learned HTML and built it on our little browsers, did stickering campaigns, and once you have that entrepreneurial bug in you, you’re always looking to mess around and just do something. It doesn’t need a bigger goal than let’s have fun and experiment with this thing on the cutting edge and see what happens.

While I was at business school, we started this blog, we called it Casa, the Casa de Cheryl and Angelique. It was these stories of our strange early-twenties dating lives. The thing went viral for back in the day, we had fans all over the place. My co-writer shared a cube at General Magic with Pierre, the now well known founder of eBay, who was running his servers out of his kitchen at that time. We needed a server to host our new HTML website, so our URL was ebay.com/thecasa. He said, hey, I need to launch my auction site, you guys have sort of a following, you were covered on NPR, you were covered on Suck.com, can I auction off a night with you guys on eBay to get some publicity for it?

I’m not even going to get into how crazy the story got after that, but I’m on page 126 of the history of eBay book with the whole story.

Syama Bunten: I want to know how much it went for, Cheryl.

Cheryl Kellond: Oh my god, no, it wasn’t that much. People weren’t spending money on the internet back then, and I won’t get into the whole story, that’s a whole separate podcast episode, about the guy who won the auction and who he ended up having to be, and the prison he ended up in. There’s a whole juicy story there. I made enough money to pay my heating bill in an old house in Boston. But it got us on the radar of AOL. There was a summer intern from Harvard Business School working at AOL that summer, John Callahan, who became the founder of True Ventures and is now on the Midas List. His summer intern project at AOL was to buy the Casa, because they were buying up artsy internet properties. AOL bought us. I made enough money to pay off my student loans in the process and move myself, and I used that and my new degree to get permission after I divorced my husband to move to California with my son. The rest is history.

Syama Bunten: How fabulous. Okay, so when it came time to sell the business, was it, holy shit, I can’t believe someone wants to buy us, how do we structure and negotiate this? Or was it more like, my god, we’re ready? How did you and your co-writer think about the price and the deal?

Cheryl Kellond: You are so funny, you are attributing all these complex adult motives to a twenty-four-year-old single mom who just wanted to get away from her town cop ex-husband and move to California. I just told you I got really excited to do an auction on eBay that paid me like $315 to pay my heat bill. It was pretty much AOL called, we were sitting on about $100,000 of student loans, and I thought, how much would that check be, and what do we have to do for you, and do we get paid before or after we do that other stuff? Whatever that number was, it sounded great because it covered my bills. I said, that sounds great, and you want me to program in Rainmaker and move my blog to your dial-up site? Sure. Is any of my payment contingent on that? No. Okay, got it. And John, your summer internship is over, so let’s sign this and we’re done with it.

It was not nearly as sophisticated as you think, and it was not a multimillion dollar exit, but it was what I needed to take the next step. I think that’s important for founders to think about. You don’t need to be the biggest thing in the world. What’s meaningful to you? The journey needs to be meaningful, and the ending point needs to be meaningful, and this had all of that. How many people can say they’re on page 126 of the eBay book? Friends have read that part over the years and said, hey Cheryl, I just started at eBay and I was reading the book and it sounds an awful lot like you. How many other single moms from MIT Sloan started a website like that? None. We’re all living storied lives.

Syama Bunten: Okay, so you divorce the ex, you take the cash, you pay off the loans, you take yourself to California. Now what?

Cheryl Kellond: Well, first, let’s be very clear, I met the man who’s been my husband for almost thirty years. Before you ask, I met him the night of the Tyson-Holyfield fight. My son had just gone back east to see his dad for the summer. We bought a keg, paid fifty dollars for pay-per-view, and told all our friends to bring their single guy friends over. He walked into my house like a fresh drink of water. Mike Tyson bit off Evander Holyfield’s ear, he smooched me, and the rest is history. So that was the most important thing that happened in California.

Syama Bunten: How long did you stay out there for?

Cheryl Kellond: That’s a math question now. About twenty years. We were near San Francisco, in Silicon Valley, for a long time. Then we got sick of the overhead of Silicon Valley and moved down to Manhattan Beach for four years. Then the kids hit high school, and Manhattan Beach isn’t really the place to be in high school if you don’t want your kids driving Ferraris and doing cocaine, which we were not totally cool with. So we moved to Colorado, and I’ve been there twelve years now. Ferraris, cocaine, no, bye.

Syama Bunten: While you were in California, you’re just a serial creator and doer, it seems like if you can think it and dream it, it shall be yours. What were some of the things you got yourself into? What was some of the trouble you started, Cheryl?

Cheryl Kellond: Good question. I maybe tempered down my troublemaking days because during that time I also had three kids. I moved between jobs pretty regularly. I crafted a career as a concept-to-launch expert, going from scratch to version one and a half, then getting bored and moving to a different company. At the time that was very easy to do. I would alternate between big brand name companies and smaller startups. I loved the startups, but imagine that kind of evolution while also having kids, you have to balance where the right place is based on your own gestational flow.

Syama Bunten: Were there any specific moments or experiences where you started to see the way the financial system was set up, the ways founders were fundraising? What were some of those California moments that laid the foundation for what you’d later evolve into?

Cheryl Kellond: That’s a super great question. Let me backtrack for a second. I did my first startup that was mine as a founder about fifteen years ago, so I’ve been a founder for fifteen years now. I stopped working for somebody else. If you look back at my story, it was clear that was going to happen at some point. A few things had to collide. I had to have the making-kids years mostly behind me. My youngest was probably five or six when I started my first startup, she could do things by herself. I had to get that behind me, but I also had to find something interesting enough to throw myself into as if it were a fifth child.

The thing that really triggered me was I had a job at Yahoo, and I loved that job. I was there at the tail end of the great years, the “peanut butter manifesto” years. It was the perfect place for me because the whole place was chaos, and I love chaos. I could deliver results out of chaos all day because there were no rules, you could pick and choose what you wanted to do and just deliver. I had an amazing time there over about two and a half years.

Towards the tail end of it, there was a bunch of turnover and change. I had great leadership there the whole time, and Yahoo had a female CEO and a bunch of female EVPs, but at the VP layer, particularly on the ad revenue side of the business, it was all guys, which I never thought anything of, I was just rolling around doing my thing. Then they did an acquisition and I got a new boss, and he was trying to figure out how to staff his team. In my time there, I had grown from a team of zero, just me, to a team of seventy. They were rolling my peers’ teams into mine. I had special projects at the exec level I had picked off and announced on stage with the CEO in front of the all-hands meeting. I had a high profile portfolio, a burgeoning team, an extraordinary concentration of talent, because if you’re a rising star female at Yahoo, you want to work on the team where the best people want to work. I was a magnet for talent. I did a ton of work to equalize salary across my team, because I was harvesting people from the rest of the company and seeing peers come in, male and female, where the woman was getting paid thirty percent less. I had this whole corporate mission of making sure people were at pay parity, and I was correcting mistakes across the org. That was my tenure there.

Then I got a new boss, and he sat down and said, I have to decide how I want to structure this team, and I need to put my direct staff as people I can give clear water to, and really connect with one on one, have a beer with. So I’m going to take this guy who’s only been a chief of staff, hasn’t run a team, hasn’t delivered big results, and make him my direct report, and you’re going to go under him, because I just don’t know how I can sit down and have a beer with you. This was a guy who used to sit down and have beers with people and talk about his ex-wife in a trashy way, talk about things that maybe you shouldn’t be talking about at work. It was very clear that one of the reasons he wasn’t comfortable with me is because I busted the gender vibe. I’d just dropped fifteen F-bombs on this call, and I could run his ass ragged talking about sports. It was a pure gender thing. I had never seen that side of the world before, because I had just rolled through, I have a big personality, I’m smart, I just did what I wanted. I was the super competent one, the one who could do the work. All of a sudden I saw that side of the world, and it was a seminal moment. I thought, I have to figure out my own thing to do, because that is never happening to me again.

I haven’t told that story in a long time. But that was a big seminal moment for me. I took a bunch of lazy startup jobs after that, mid-tier companies that weren’t growing fast, because I had a kid I needed to graduate, and a daughter I was adopting. We moved to Southern California to get out of the Silicon Valley thing, I needed a professional pause in my life, but I couldn’t do it without a salary. So I took some crafty jobs. Then when we moved down to LA, I figured out my first startup and took a big swing at something. It was in the cards from day one, but I needed that combination of that boy moment and a little freedom around me to figure it out.

Syama Bunten: Absolutely. Southern California is a different vibe, even now, a totally different vibe. Talk to me about taking a big swing at something, especially now when you have a larger family, not just a family of two, there’s a lot more to think about.

Cheryl Kellond: Or free-ranging kids.

Syama Bunten: Yeah, there’s a lot to think about. It doesn’t strike me that you sat down and asked, what does security look like? But obviously with a family there’s conversation and consideration. What did it look like to have this conversation within the family, to say, this is going to happen, you all know me, I’m going to go balls to the walls on this, get ready? How much conversation happened before it got unleashed?

Cheryl Kellond: You are indeed so cute, haven’t you met me through this call? Oh my gosh, no. I was up drinking with a girlfriend one night. We had moved to Southern California, four kids, but they were free-ranging and could make their own lunches. I got into triathlon, just getting into the sport, and I was out drinking with my girlfriend one night, and we said, these Garmin watches suck, we could build something better than this. I totally drunk-dialed a bunch of friends, found a girlfriend who had started a connected jewelry company and knew the entire sports watch team at Nike, who had just shipped their product and let the design team go.

There was no big contemplative moment around this. I was drunk-dialing entrepreneur girlfriends and got a hookup with the Nike team, and all of a sudden I was a founder. I didn’t like the job I was at, so all of a sudden I was a founder. My husband is the world’s best husband, he was like, okay honey, you’re going to do a thing. We didn’t have a discussion about what it would mean financially. I am absolutely sure we didn’t think about that in the least bit. And you know, if I fast forward a few years, we should have thought about it.

One of the biggest reasons we moved to Colorado is we couldn’t afford to live in Manhattan Beach or anywhere in California on one real salary and a startup founder salary. The startup was doing consumer electronics from scratch, so there was no salary, there was money going into the business that we didn’t have, credit card money going into the business. So no, we didn’t think about any of that. One day I will. That would be cute, and I’ll call you when I do, but it hasn’t happened yet. We said, let’s launch it on Kickstarter, and we did. There was so little thought put into it. More curves and sense, baby. More curves and sense, it’s the only thing you need to remember about me.

Syama Bunten: I was eleven years old the first time I learned that nice things weren’t for me. That belief ran quietly underneath my entire financial life for the next twenty years. That’s the reason I built the Money Story Reset, five reflections on the beliefs shaping your relationship with money. My own stories are in every single one, including the parts I don’t usually say out loud. I didn’t write this from the outside, I did every page myself first. It’s free. The link is in the show notes, or go straight to wealthcatalyst.com/reset. That’s wealthcatalyst.com/reset.

What did the kids know of mom? Was it, mom is into stuff? Did they understand what it meant for you to be a founder and start a company? How much did you talk to them about what mom did?

Cheryl Kellond: I didn’t have to talk about it, because they saw it, it was happening in the house. They loved it initially, they used to call me a racer, they’d go to triathlons on the weekends, it was really fun, they were little elementary school kids who wrote my race numbers on things because they thought it was really cool. That eventually got old as the races got longer, and they’d say, why are we out here all day in the cold, who cares mom? But they very much knew what I was doing all the time, because we were developing hardware, and a lot of it happened at my kitchen table. We had sports watches, we put them on the kids’ wrists and told them to go run around the block because we were testing things. We were shipping physical products, we had shirts for our Kickstarter backers, and I’d tell the kids, you’re going to use the label printer and mail them out, and I’ll pay you ten dollars for the afternoon because you’re eight. College fund, right, exactly, college fund would have been if mom was at a real job.

The moment I remember the most, though, my main hardware and antenna engineer was moonlighting from Google, his day job was at Google, he invented the GPS system behind Street View and Google Maps. He used to come to my house on weekends and build circuit boards, and my daughter used to watch him work. One afternoon he told her how to read the circuit board picture on the screen to find problems, any errors, how to point those out. Then she used to sit at the kitchen table, open up her fake computer, and hold her little stuffed animal baby, pretending to spot things on circuit boards. That’s how she used to play house, mom is working, she’s holding the baby and giving the baby love, but she’s doing something on her computer. Then every now and then she’d stand up and pretend she was on her Bluetooth headset and start talking in a spicy voice. It’s just part of who they are, these are the jobs they had, this is what they helped with. Her way to imitate me and play house was work and family all blended together, and it was fairly lovely.

Syama Bunten: What’s the spicy voice?

Cheryl Kellond: You can imagine it.

Syama Bunten: Oh my god, I love that so much. Okay.

Cheryl Kellond: Kids around enough spicy language, they know not to use the spicy words. You use it every once in a while and they’re like, ooh, I’m going to try that out. If you use them all the time, they just know that’s not for us.

Syama Bunten: Okay, so now you’ve had this first official bug of building and growing something under your belt. I feel like there’s something powerful about doing something once in that way. I’ve never birthed any children, but I’ve had three businesses now, and I feel like you always kind of forget what the labor is like to get it off the ground. Is that anywhere like having children, where you say never again and then decide to do it again?

Cheryl Kellond: Yep. Usually now, when I do something and tell myself I should never do that again, I make up a little song about it. I did that after a certain triathlon. It’s interesting, it came up two weeks ago, my girlfriend said, hey, we should go back and do that triathlon, and I said, no, I said I was never going to do that again, I have a song. I said that after my third son too, I made up a little song, I don’t ever want to birth a child again, which is why we adopted our fourth kid, I made up a song for that. I’ve never made up a song about starting a startup, and I probably should have. I’ve done it multiple times.

Syama Bunten: What was it like for you to decide to do another company afterward? How did you decide it was time? Was it overlapping at all, like I’m ready for something else, wind this down and start something else?

Cheryl Kellond: No, no, no. I don’t know those founders who can go from one thing straight to the next, more power to them, that’s amazing. No, the first one, we shipped an amazing product, we had a rapidly loyal fan base, they used to draw our product on the race course in chalk to cheer each other on. We were the number one rated product in the category on Amazon. Fifteen years later, I still run into people who backed us on Kickstarter who can tell me a story about how we made them feel and what we helped them do. But the company was a failure. I was trying to do consumer electronics on a shoestring budget, it was never going to work, let’s be really clear. I didn’t realize that at the time, but now it’s the easiest thing in the world to see. It took me a long time to recover from it, both because I was exhausted, but also because as a first-time founder, I felt like people invested in me and lost their money. It took me a long time to get over the fact that that’s part of being an investor, no one can blame me, I gave it an amazing shot, and people were telling me that. But it took me a while to work through both the exhaustion and the sense of failure.

I probably took two years off. It was right after we moved to Colorado. I did Iron Man Canada twice in that time. I spent a bunch of time with the kids, we had ice cream for dinner every night. I learned to be silent with myself. I did some side projects here or there. I knew how to do Kickstarters, so I helped a few companies with theirs. I knew not to do hardware, and since I was new to Boulder, Brad Feld turned me loose on every entrepreneur in Colorado who thought they could build hardware, and my job was to convince them not to. I was very good at it, they should all thank me. So I had two years of this weird non-obligation kind of side hustling, but it was recovery, it was emotional damage and recovery. Anyone who can go back to back to back as a founder, good on them, but there should be an employment insurance fund for founders, because we need to spend some time on the bench recharging, it’s hard, it’s not pretty. But ice cream for dinner every night was pretty good.

Syama Bunten: How was it to experience that? I’m sure the kids were stoked you were home. How was it with your husband, moving through those two years? Tell me about the shift in identity, did you two have a conversation about what this meant, how did you integrate that experience together?

Cheryl Kellond: Again, you’re projecting adult behaviors on me that maybe I don’t exhibit. Our big shift, I knew we had to shut it down when it wasn’t working, when we left Southern California and moved to Colorado. That was another one of those crazy impulsive moments, we hadn’t been talking about moving. I went out here for the first time to visit a girlfriend who was having a baby, and I was on the ground for twenty-four hours and thought, we need to move here. All the things we love are here, it’s beautiful, it’s affordable. And we had that Manhattan Beach kid in high school situation that maybe wasn’t sitting right with us.

I went home and posted on Facebook, back when Facebook was still popular, hashtag “Boco Relo,” and the kids saw it and had a sibling huddle like, what’s mom talking about? I came home and said, honey, I think we need to move, it’s amazing there. Because of where it was in summer and where the kids were in school, we had to make a decision fast. From me first visiting to when we rolled up in the moving van to our new rent house four days before school started, the day before the kids flew back from summer camp to a new house, was sixty days. There was an Iron Man in Canada in the middle of it too.

That was the conversation of what do we want our life to be, because clearly I was going to be a founder. My husband is amazing, he runs his own business, he’s an architect, he builds real things, not a computer guy, it’s super sexy, like Brad Pitt meets Mike Brady, a good guy to marry into. Those were the roles in our relationship, and he knew that’s what made me happiest, and that’s what made our family healthy, and it’s a great relationship. But it wasn’t the “let’s sit down and talk about what we do next” kind of decision. It was, I know you’re going to work through it, honey, I love you. That’s the way it goes.

Syama Bunten: It’s so delicious and sweet. So then, the next business idea comes up, no conversation, off to the races?

Cheryl Kellond: One hundred percent, yes. It’s like, are we doing a thing or not doing a thing? I think there is a thing, it is a thing. It was funny, even this last time, I did a business in the middle, and after I sold it, I had about two and a half years where I wasn’t working working, I was volunteering as an entrepreneur in residence, had some side hustles, was getting a little paid for a bunch of projects. It never felt like I stopped working. The moment of, I figured out the thing and now the thing is official, didn’t change the flow of things day to day in our life. I get a paycheck, that’s really good, we pay off some of the hole I dug when I didn’t have a paycheck, but every relationship has, you know, we play roles for each other. You find the right person and it’s fantastic.

Syama Bunten: That’s really beautiful. So tell me a little bit about the transition. You’ve had corporate experiences, multiple founder experiences, when did you start to think about your own money and portfolio? When did the investor hat start for you? What was the moment you went from being on one side of the exchange to using your capital to create the change you wanted through other people?

Cheryl Kellond: As embarrassing as it’s going to sound from someone with an actual business degree from actual MIT, I didn’t think about it as much as I should have as we were going. I had four kids and had them early, we were make-it-and-do-as-we-go. There was never a giant wealth creation moment. I told you the story about getting bought by AOL, there’s a reason I told you that story and none of the others, that might have been my big wealth creation moment. It was probably in my mid-forties that I started thinking about that, and had this “duh, I’m such a damn idiot” moment about compounding interest. We were trying to keep up with the kids and do a thing, and hadn’t thought about our money and invested like we should have, even fully funding 401(k)s and letting it compound, we were not in that group. We were trying to put a house over their heads, pay for school, move them through life.

I made decisions not to drop out during my biggest earning years, maybe if I had been more thoughtful I wouldn’t have. But my husband and I both know it wouldn’t have been sustainable in our relationship, because that wasn’t a place I was supposed to play, so no woulda-coulda-shouldas. My whole team at Yahoo, most of them ended up taking jobs at Facebook, and left there as COO or EVP of a business unit, mind-changing wealth, that was not the place for me. So I came to it late in life. For this particular piece of investing, I came to it through my love of startups, and through that lens of power, first check calls the game. If you write that first check, you get to decide what problems get solved and who gets to solve them. So I came at it through love of startups and through that lens of power. Tiny checks can add up to big change, and we can actually change what’s there for us down the road by doing these little things now.

It didn’t come from a holistic wealth management perspective, even though I am Series 65, thank you very much. I came at it from, there’s this capital here and these problems need to be solved, what is the most efficient and effective way for me to have a giant impact there.

Syama Bunten: What was the first check you wrote? What was it for? How did it feel? You never forget your first, there’s that moment of, am I really going to do this, okay, yeah, I’m really going to do this.

Cheryl Kellond: No, this was a funny one. I’d sat on the sidelines for a while looking. My angel story is, I started to learn about angel investing because I thought it would make me a better founder, and a better mentor and coach to the hundreds of founders I was working with. It dovetailed with when I sold my second startup. The thing to do back then, if you’re an exited founder who loves startups, was to become a fund manager, which I was like, hell no, I’m not doing that, I hated fundraising, why would I do that for my job, that would be stupid. But I wanted to sit in the middle of that moment. So in parallel, I was learning about angel investing myself. I started with Hustle Fund Angel Squad, they taught me a bunch of things, everyone starts with Hustle Fund. Squad five here. I’m probably the only Angel Squad lifer who earned lifer status by referring enough people in, just so you know. Haley Bryant was the first angel investor in my company Play Money, so lots of squad vibes and love. I jointly owned some NFTs with Elizabeth Yin too, my squad vibes go wide and deep, love that crowd.

But my first investment, I made it through an angel network, into a company called Moxie Baby. It was an at-home IUI kit. The founder was really smart, I loved the market, Jenny Fielding from Everywhere Ventures was one of her initial investors. I wouldn’t have remembered the details, except I recently went to download my tax documents and saw the investment was a complete write-off, I took a full loss on it. I had never heard a word from the founder, what’s going on, their website’s still up. She posted the other day that they were acquired, but truly it was an asset purchase agreement, for reasons I don’t know, because the founder never communicated. But that was my first investment.

I was going to do it with girls, I liked the business, I trusted the investors in it, it felt great. It would have felt better if the founder had been a better communicator throughout, because that’s part of what I learned on my journey. I had all these angels and backers who still think the world of me and my company and what we did for them, and part of that was because we communicated every step along the way and they got to be part of the journey. If angel investing is actually just an expensive paid newsletter subscription, at least deliver the newsletter.

Syama Bunten: So that was your first, and then the appetite grew, along with a business model and a thesis and vision for the world. How did it start to snowball? When did the moment go from maybe to okay, this is it?

Cheryl Kellond: Gosh, there’s never one defining moment where you cross over that leap point. I had been doing customer discovery about a bunch of different businesses, playing around with this one. I saw something after talking to hundreds of would-be, should-be, could-have-been, sort-of-were, actually-were kind of angels, and it felt like we had obsessed over this. If we rebuilt the process of early stage capital from the point of view of the person actually writing the check, the individual and the founder who needed it, what would we put there?

What I was seeing everywhere was there was a ton of people who wanted to be in that space and should be in that space, because it affects the future and should be part of a sophisticated financial portfolio. But I also saw it from the founder perspective, and there was this fragmentation tax happening. It was super exciting in the zero-interest-rate years, because new kinds of fund managers were emerging, they looked different, had different lived experience, were backing different kinds of founders, unlike the fundraising environment I grew up in when it was twelve firms on Sand Hill Road, and it was a bit of a hazing ritual, especially if you came in as a woman doing an athletic product, like, “do girls even do sports,” it sounds ridiculous but it was a little bit like that.

Seeing what was happening with all these new fund managers and capital flowing to new places and new kinds of founders was super exciting, but there was also a tremendous fragmentation tax on it. The best founders were pitching a hundred angel groups, four hundred individual investors, it was so inefficient, the process hadn’t evolved at all: get a warm intro to everyone you know, stop running your business, go ask them for individual checks. I saw a product opportunity there, is there some way to get the fragmentation out from where it shouldn’t be, but leave that individualism around taste and problems to solve, and that gut feeling about where the future is going, leave that really pure, but make it easier for both sides.

We’re still figuring that out, but we know a lot more about it. We are moments, days away, I told you when we started, from having our first million dollar month on the platform, we’re moments or days away from eight million dollars total moved through the platform. What we’ve learned along the way is the trajectory people go through, from “I heard I could do this thing” to “I am a capital-I Investor,” it’s an identity journey, a permission journey, a time journey. Our core premise was there’s a lot of people sitting on the sidelines who want to be here and should be here, but we’ve made it take so much time. So we solved for the time problem, and then unpacked the next layers of identity formation and behavioral change. Now we can go to market and say, hello, my name is Cheryl, I’m founder of Play Money, and we know how to mint net new private market investors, and when you unleash their capital, look at the kind of stuff that gets funded.

It’s lovely to be doing this in a moment when private market capital is all concentrating and playing a “me too” consensus game on a few small companies, because that leaves this giant blue ocean of real technologies and real problems being solved, around climate, around women’s health, or in things you just love, home goods and CPG, and this whole set of new spaces with great entry valuations, a known pool of buyers, and no big institutional capital paying attention. So guess what, we can fill it with private capital and just make bank.

Syama Bunten: Love that.

Cheryl Kellond: Hope things happen, right? We can build what we want to buy down the road. This is the world’s biggest, run the table, count the cards, we can do it all, we’re the consumers on the other end, we’ve been the investors all along, let’s own a piece of the cap table and own that equity so we get all the upside.

Syama Bunten: I love that so much.

Cheryl Kellond: That’s what we’re doing now with Play Money.

Syama Bunten: It’s a powerful entry point, to let consumers and people know that they too have control over the headlines in the news, based on how they choose to invest their time and money. I always like to tell people, if you don’t like what’s in the news, put your money and time somewhere else, so you can invest in new headlines.

Cheryl Kellond: Exactly. And that investing happens now. It’s okay if it feels like shopping some days, it’s okay if it feels like impact with upside some days. We’ve created an environment where it’s always free to lurk and learn until you’re ready to jump in. We do that education in bite-sized pieces, so you don’t feel like you don’t have enough time or you don’t know enough. The funniest thing we hear at Play Money is, well, I haven’t signed up yet because I’m waiting until I can block off a bunch of time next week to really figure it out. I’m like, you’re going to be disappointed, sweetheart, it takes five minutes, and then you’re scrolling startups and learning in bite-sized pieces instead of interrupting your life. That’s how I think more experiences are going to be built going forward, because it needs to fit into this multidisciplinary adventure we’re all on, where we can have multiple interests and our time can be spent on multiple things, and we can always be multitasking, and that’s okay. We need to fit into those nooks and crannies for things to be truly inclusive and get the things we want out the other end.

Syama Bunten: I love that. It’s no doubt that, especially considering how athletic and strong you are, this statistic will certainly be surpassed, but with longevity science, we’re all going to be living far longer. Certainly with your health and wellness, you’ve got another sixty years, so in many ways you’re just getting started. Thinking about this body of work you’re creating, whether or not you give yourself credit around intentionality, your spirit has really guided your moves and energy and the impulses to direct things. How would you want to reflect on this body of work at the end of the next sixty years?

Cheryl Kellond: First of all, thank you for seeing through my lack of intentionality to a tremendous amount of purpose and vision behind it, I appreciate being seen that way. Here’s what it is. I want to take this whole new generation of people who have even a little bit of extra capital, and use what we’re building to move billions behind all the problems that aren’t getting solved, into market-based solutions, so they can be sustainable and wonderful and wealth-generating, and build it up from there. I want to help catch up on where we haven’t been deploying capital before, to solve the problems we need solved. I want to move billions. Billions, because that’s what it takes.

One of the big “aha” moments on this journey for me was, if just twenty percent of us who are accredited investors invested just $10,000 a year, which looks like a couple of long weekends, or maybe what we’ve bullshit-spent at Target, we would move $30 billion of capital a year. That would replicate the entire early stage startup ecosystem from angel through Series A. Think about the power. We could just invent a whole parallel universe, with that kind of economic power, at $10,000 a year. We all have that. If you’re accredited, you have that. You’ve probably spent it somewhere dumb. My $1,500 checks feel like they can move the needle when I think about it like that, and that’s super powerful for me at least.

Syama Bunten: I love that. That’s beautiful, Cheryl. We’ve spoken about money across so many different ways, exits that can move you to the next step in your journey, investing, 401(k)s, retirement, writing angel checks. We’ve talked about money in so many different capacities. I’d love to turn our attention to the fun side of money. What has been one of the most fabulous ways you’ve spent your money most recently, other than investing in a fabulous startup?

Cheryl Kellond: Well, I just had a sleeping environment overhaul moment about a week and a half ago. I bought a $240 feather bed from Quince, and now my bed feels like the best bed at the best hotel. Love it, it was a fun summer thing. I used my money for that, which was amazing, and it’s been heavenly since it arrived five days ago.

On the experience side, we did a big splurge trip over the holidays and brought all the kids to Costa Rica, a ten-day family trip with the kids and their extras. It’s great when you have adult kids, they bring extra people with them because they get their person. We went from a mostly boy family to an evenly balanced boy-girl family because we brought the extras along. We just had the best time in the world with them, kicking back and having an adventure and getting to be with them all together. Isn’t that what money’s supposed to do? Bring you joy, be able to take care of your people and spend that special time with them. I couldn’t be more blessed.

Syama Bunten: I love that, that’s so beautiful. And then my last question, Cheryl. Everyone who’s listening to the show, we always like to rally around the guests. So why don’t you tell us, what are you calling in right now? Where do you need extra love? How can we support you on this mission you’re on?

Cheryl Kellond: Yep, so here’s the rub. Every single person I’ve talked to on Play Money, I talk to customers every week, and most of them can tell me exactly who brought them into angel investing and how awesome it was. Very few are comfortable sharing it outward, it’s something we don’t talk about. So my big ask is, talk about money, bring someone with you, sign up for Play Money and tell a friend and bring them with you. It’s free, and you’re going to learn something along the way. Maybe you decide to angel invest, maybe you don’t. Maybe you see something you love on there and think, my gosh, I can be a part of this. You’re going to learn something regardless.

But I think the bigger message is, yes, I’m always going to say sign up, but tell a friend. Tell a friend about this crazy conversation and start talking about it more. Guys talk about this stuff all the time, I got this scoop, I saw this company, I did this thing. But talk about it in our terms, this is how it made me feel, or this is how they crushed it, or see this coffee I’m drinking, this supply drink I’m drinking, I’m an investor in it. See this Fishwife fish I’m eating, or Daily Crunch, where’s my bag of Daily Crunch, I kept a bag of Daily Crunch on my desk for a while, kept saying “in a pickle” because it was pickle flavored. Tell your friends about that thing you invested in, or that founder story that captured your imagination, because you’re going to open up a world you discovered for yourself, and she’s going to be so grateful.

Syama Bunten: I love that, Cheryl. What a gift to have you on the show today. Thank you for your spirit, your heart, your generosity. Thanks for answering all of my questions. I so enjoyed getting to spend more time with you. Thank you for being here.

Cheryl Kellond: Lovely. Thank you for having me.

Syama Bunten: Thank you for listening. This is the conversation we come back to every single week. Real women, real wealth, and what becomes possible when we stop being silent about money. If today’s episode moved you, don’t let it stop here. Wealth Catalyst is where women go to take it further. Our Freedom Tour salons are gathering women in 32 cities this year, intimate evenings in homes and private spaces where women talk honestly about money, risk, and what they’re building.

And if you’re ready to go even bigger, join us at the Wealth Catalyst Summit, a full-day event in New York City this May, and San Francisco this October. Find your city and claim your seat at wealthcatalyst.com. We’ll see you there.