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‘Taylor Swifting’ the World of Angel Investing: How to Invest in Startups Through Your Retirement Account with the Founder of Play Money
80 Plays1 year ago
Update: I recently launched my newsletter, The Sheconomist, and would love for you to subscribe: sheconomist.com - I share so many tools and resources that help young, high-achieving women with radical money and career self-advocacy.
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This week, we're joined by Cheryl Kellond, a trailblazing serial entrepreneur and investor with a track record of success in Silicon Valley. Cheryl has shipped over $750M in Version 1 products at startups and brands before founding her first startup. Her 2nd startup was a healthcare fintech where she raised $17M in Venture Capital funding and grew to $10M in annual revenue before exiting in 2021.
Her latest endeavor, Play Money, combines the addictive engagement of TikTok with the savvy investment opportunities of AngelList. It's a game-changer in the world of startup investing, democratizing access by empowering everyday people to invest in early-stage companies through the retirement investment accounts (IRA). Angel investing, Cheryl explains, isn't just for millionaires.
Cheryl sees angel investing as a catalyst for learning, networking, and shaping the future. By bringing people together around shared investment opportunities, Play Money isn't just a platform—it's a community, empowering the next generation of investors to make their mark on the startup world.
Cheryl's mission extends beyond financial gains. She's challenging outdated norms in entrepreneurship, urging us to rethink how we talk about gender and inclusion in the startup world. For Cheryl, women are not the exception—they're the norm, and it's time we start treating them as such.
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Transcript
Are women inherently better suited for angel investing?
00:00:00
Speaker
Particularly as women, we are already better angels than we know we are. Angel investing is about picking the outliers. We see different problems. We resonate with different founder strengths. This is one place that we are not the normative. We are not the bulk of check writers. So what we see and what resonates with us is more likely to be that outlier. And we should step into that. That should be the normal. The outliers in this space are normal.
00:00:26
Speaker
as women. Boom, mind-blowing, better ages than we already know.
How can women reclaim economic power?
00:00:33
Speaker
I'm Tamina and I'm extending a heartfelt invitation to you as we join forces in reclaiming economic power for women in a world that is often structured against us.
00:00:45
Speaker
We'll dive into the minds of accomplished female leaders, investors, and entrepreneurs to equip you with the confidence and knowledge to build wealth for yourself and other women. So buckle up, get ready to learn, and be inspired to take action. Welcome back, everyone. Let me tell you this. You all are in for an absolute treat
Meet Cheryl Kellan: Entrepreneur and Angel Investor
00:01:06
Speaker
this week. I am so incredibly thrilled to be welcoming the one and only Cheryl Kellan to the show.
00:01:13
Speaker
Cheryl started her career as a concept to launch expert in Silicon Valley. She shipped over $750 million in version one products at startups and marquee brands before founding her first startup.
00:01:30
Speaker
She kick-started, and I quote, the sports watch Steve Jobs would have built into the number one rated fitness variable on Amazon. Her second startup was a healthcare fintech where she raised $17 million in venture capital and grew to $10 million in annual revenue before exiting in 2021.
00:01:51
Speaker
Since the acquisition, Cheryl's been an active angel investor and the entrepreneur in residence for Techstar's new pre-accelerator program, where she has worked with over 100 founders.
What is Flame Money's mission?
00:02:02
Speaker
Her new company, and I'm excited to be talking about it today, Flame Money, is reinventing early stage capital and activating the next 1 million angel investors through an experience that feels a bit like if TikTok and Angelist had a baby.
00:02:21
Speaker
Cheryl, I am so, so thrilled to have you on. Welcome. We are going to have so much fun. I'm so excited about this conversation.
00:02:29
Speaker
Me too. I know we just like hit it off from the very moment we met first virtually and then in person a couple of weeks back in New York. And I'm just so excited to kick out about all things Angel Investing over the next few minutes or so. Before we start talking about Angel Investing and play money, I would love to start out with the question that I like to ask all of my guests at the beginning of the new episode.
00:02:54
Speaker
You know, Cheryl, as we grow older and evolve in our personal growth, there are certain things such as beliefs or perceptions that we often unlearn. And I'm curious to hear from you, is there maybe something that you have unlearned in your journey towards advocating for gender equity?
00:03:10
Speaker
Oh, that's a good question. I am a loud and proud GenXer, so I have definitely had plenty of time to learn and unlearn things. The latest kick I'm on is that I'm really done saying stuff like, female founders and four women
00:03:29
Speaker
It hit me a few months ago. It's not a secret sign of solidarity or inclusion. If you're saying it about you because you're running a startup, it's actually one of the most obvious and least interesting things about you. What we're doing by saying these words all the time, it feels like we're systematically othering ourselves.
00:03:49
Speaker
Right? We're half the population. We have more than half the college degrees. We control nearly all the consumer decision making and spending. As women, we're not the exception. We're not the other. We're the normative. And this has been sort of an aha for me that I've grown into, but
00:04:06
Speaker
Since I started rolling through life, the problems I think are important to solve or that my point of view that I'm seeing is actually universal and not cadaided as for women, the response to what I'm doing has changed. All of a sudden you see men nodding their head and leaning in.
00:04:24
Speaker
Whereas if I had used the W word, they would have had permission to check out. And it's been super impactful on play money. If you look at our website, right? There's a little bit of a, it's a different vibe. Women are responding to it, but there's no W word on the whole thing. And it's made a difference in who's participating, who's engaging. So yeah, that's my latest tip.
00:04:45
Speaker
We shouldn't other ourselves. We are the normative. Let's assume we are the normative and we will roll through with a different kind of confidence and I think a different kind of support. We trick some people in. Trick some people into intrusion horses. That's so important. And I love that
Debunking myths: Is angel investing only for the wealthy?
00:04:59
Speaker
phrase of like, we're using to other ourselves as women. And I totally admitted I used a female founder and the W, you know, women or girls or whatever context it might be.
00:05:11
Speaker
all the time because I still do believe it is important to call out systemic discrimination that is a thing that a lot of women and other minorities, especially minorities who intersecting identities,
00:05:27
Speaker
add up. I think it's important to point that out, but I also agree that it's important to just say sometimes, hey, I'm not a female founder, I'm just a founder, or I'm not a female CEO, I am a CEO. And to start normalizing that more and reading that into our daily use of language, because at the end of the day,
00:05:50
Speaker
The use of language is so, so powerful. It can be very inclusive, but it can also be very exclusive. And I think we should all be a lot more mindful.
00:06:02
Speaker
So I agree with you. There are times to point out those words because you're talking about systemic discrimination. But if I'm describing myself, if I have five seconds to get your attention, telling you I'm a female founder is not as impactful as telling you I am an exited founder that grew a business to 10 million in ARR and here are my superpowers.
00:06:23
Speaker
Yes. Love that. Step into your power. Amazing. Great part. So Cheryl, let's just dive right in because there's so much to cover. I want our listeners to learn everything about PlayMoney because I just think it's so, so cool what you're billing. I've told you this a hundred times already, but I do think it's important to take
00:06:42
Speaker
step back and first provide some important context on the problem that play money is trying to solve. Because as you probably know, this podcast primarily caters to an audience of younger women. So women in their twenties, in their early thirties. So a lot of them have heard about angel investing and venture capital and all of that good stuff. But I would argue that the majority of the people
00:07:07
Speaker
have not invested in a startup just yet. A lot of them are starting to figure out how to invest in the stock market, start contributing to their 401ks, to their IRAs and whatnot. So I do think it's important to provide some context for those listeners.
How is Flame Money changing angel investing?
00:07:24
Speaker
So you already mentioned your website, which again, I love, and we're going to talk more about that later on. But on your website, it says, play money changes the rules of angel investing so more of us can get in the game. Why is the traditional angel investing model so broken, Cheryl? Great question.
00:07:45
Speaker
I wouldn't even say that Angel model is broken. It's just only half fixed. Angel's becoming sort of all the rage, right? And it actually should be. Yes, it's a high-risk asset class. We're going to talk about that in a little bit and how to reduce some of that risk. But I mean, whoever writes the checks decides the future. You decide what problems get solved, and you decide who gets to solve them. That's an amazing, powerful thing. And the more different kind of people that are doing that,
00:08:15
Speaker
the more we're going to get better problems being solved and better people solving them. Also, especially early in your career, actually late in your career too, angel investing is a flex. Come on. You see the future as it's happening and we all know, we say, oh yeah, I'm an angel investor. That's a total flex. Guys do it all the time. There's no reason everyone shouldn't be doing it in that sense.
00:08:38
Speaker
And over the last decade, the financial barriers to angel investing actually have gone down. You can make $1,000 investments in companies on AngelList now. That's huge. The thing is though, I think Angel feels inaccessible still for two reasons. First of all, there is a little bit of stuff you have to learn about it.
00:08:59
Speaker
And most of the groups educating people on angel investings are VCs. And they're sort of educating angels I've seen from the perspective of a VC. VCs benefit. Their business model really revolves about them making a few very large bets each year. They need to do a ton of diligence on those bets. They need to see thousands of companies to make those bets. They have to be able to really dig in and help those companies.
00:09:25
Speaker
What this says to me as an angel is, oh my gosh, it's a huge barrier in time and experience. There's all these hurdles. I don't know enough to be an angel investor. And I certainly don't have enough money to make a few large bets each year and then be helpful to those companies.
00:09:42
Speaker
It sounds really intimidating. The thing is, angels are not small VCs. In fact, the way we should approach angel investing as an asset class as angels is by making a whole bunch of smaller bets. And there's a ton of math and research to back this up. And once you see it, you can't unsee it. But while a VC is gonna benefit from making a handful of bets a year and hopefully getting that one massive unicorn and
00:10:08
Speaker
fund that performs in the top 10% angels, most of us want a more
Mitigating risk through diverse investments
00:10:14
Speaker
predictable high performing asset class. We don't need to be in the top 10% unless we also want to be VCs and invest other people's money. For ourselves, we maybe just need to outperform public markets, make the asset class worth its risk, but we don't have to be the very best. The way to get there is to make a bunch of smaller bets. There's actually this magic numbers.
00:10:36
Speaker
Once you have about 30 investments, this magic thing happens and instead of your investments performing like a bunch of individual lottery tickets where most will fail and maybe you'll get a winner, once you get around 30 investments, your investments start to sort of perform together and it looks like a more predictable high performing asset class.
00:10:58
Speaker
you're not going to lose all your money. Lots of your companies are going to fail, but the winners will make up for it. And it looks like an asset class that pretty consistently hits or outperforms the public markets. The problem is, the first problem was that they're not educating us right. The second problem is, if you actually go to make those 30 investments, maybe you want to make 12 to 15 a year, that is way too hard. I've tried to do it for the last two years,
00:11:25
Speaker
And to get that kind of deal flow and to pick the ones you like, it takes too long. It becomes a burden and not a joy. So that's really where Play Money comes in, right? We're building this fun, engaging deal flow platform that shows you the kind of deals you want to see so you can pick the ones and invest in the ones you love. And it gives them to you in an engaging format that's great to
00:11:52
Speaker
interact with online and to talk about with friends, to make it a social and a learning activity in addition to an investing activity. So that's what we say we do. Our promise is you can build your dream startup portfolio, and we're thinking 12 to 15 investments a year, with as little as an hour a week
00:12:13
Speaker
and $6,500 a year, which is the amount that goes into your IRA. So people are resonating with the, oh, wait a minute, I can see this kind of deal flow and build this portfolio and have fun with the engaging format. They're also resonating, maybe not so much with that dollar amount, but with the piece of it. So we're making it both accessible and CL accessible.
00:12:35
Speaker
I want to talk more about the IRA or retirement account side of things in a minute, but just wanted to reiterate what you said, a big problem that we have as it pertains to getting more people into the space. And I'm not just talking about angel investing, although obviously that's the focus of our conversation, very much a big focus of this podcast. But when I think about getting younger and especially women and minorities into even
00:13:00
Speaker
investing in the stock market, it's that lack of financial education that we have, right? We must never receive a proper financial education growing up. So that's a big challenge. Then as a result of that, there are so many misconceptions and false rumors going on. For Angel Investing, it's
00:13:22
Speaker
still known to be very inaccessible opportunity that is only an option for people who are already wealthy, but not for people who want to actually start building generational wealth from scratch. And obviously there are, at least in the United States, still some regulatory challenges, although you pointed out that the barriage entry has been lowered in recent years and there's
00:13:48
Speaker
currently a couple of changes to the laws that are being proposed and that they're sitting with Congress right now to make it even more accessible to more people moving forward, where you don't necessarily have to have a certain net worth number sitting in your bank account, or you need to be earning a certain amount of money per year.
00:14:10
Speaker
to become part of this entire ecosystem.
Democratizing angel investing for smaller investors
00:14:14
Speaker
So I love the fact that you're really focusing on addressing those misconceptions, providing education and making it more accessible because in the past, most people had to write
00:14:27
Speaker
six figures, sometimes seven figure checks in order to participate. Right. And now you can join it with as little as one grand and some of the smaller equity crowd funding platforms even allow you to invest as little as like $50. Right. So a lot has changed, but I feel we just need to educate, educate, educate. And that's why I love what you're building so, so much because it definitely appeals to, I think a broader set of people.
00:14:54
Speaker
Oh, I appreciate that. You know, two thoughts to go along with that because you did mention equity crowdfunding. I want to be really clear on PlayMoney, we are talking venture quality and venture vetted deals. The deals you'll see on the platform are coming from some of our favorite pre-seed and seed stage emerging fund managers. This whole new crop of more diverse
00:15:18
Speaker
fund managers looking for the best startups and the best kind of founders in different spaces, but these people pick and invest in companies professionally. So it was really important to us to make sure the companies coming on the platform had gone through that filtering and vetting process, right? Like a VC is going to look at hundreds, if not thousands of companies for every investment they make.
00:15:42
Speaker
we want that kind of vetting in there and insight to come with the companies on our platform. So we can always be teaching our investors something at the same time and something that they couldn't know as individual investors because they don't see the deals, they don't see different kinds of founders, they don't see different ways to approach a problem. So we're making sure that everything comes in the platform is curated from that high quality deal flow. And so I just wanted to make that differentiation. Then the second thing that you triggered in my thought,
00:16:11
Speaker
It's so interesting because Angel is a high risk asset class. I would be irresponsible not to say that. As we all learn to build wealth, and saving is one thing, building wealth is investing what you've saved so it can grow without you doing anything. The bulk of our portfolios should still be in publicly traded stocks and bonds. That is actually the truth.
00:16:33
Speaker
It's also becoming more common knowledge and more accepted knowledge that we should all have a portfolio of alternative asset. A portion of our assets should be in alternative investment. Then startups are one of those. And so it is in the realm of responsible investing if you do it wisely. I love startups because it's not just you can invest and build up a portfolio for financial returns.
00:16:56
Speaker
the learning, the networking, the socialization, the ability to see the future and know what's coming, that comes along with startup investing that I think is so valuable to so many people in both their personal lives and in their professional lives. So it's like a little gift that gives in a whole bunch of different ways.
00:17:15
Speaker
Absolutely. And I just love that you brought that up because at the end of the day, certain investments, let's say in the stock market, for example, that can sometimes be a little boring, especially once you've set up your tools, your processes, you have your automatic deductions.
Beyond returns: Learning and networking in angel investing
00:17:30
Speaker
At some point you will reach a ceiling as pertains to your opportunity to learn and grow.
00:17:37
Speaker
pointed out networking. I think that is one of the most beneficial side effects of this whole startup and venture and angel ecosystem. You just continue to meet so many interesting people who are very excited about building things and specifically within the community that we operate in. It's not just about building cool products and services. It's about addressing specific needs that have historically not been addressed because
00:18:04
Speaker
There has been that lack of diversity in this ecosystem for a very long time. And we're now just starting to see how the narrative is. And I think that is so exciting. And it also gives us an opportunity to truly like vote with our dollars when we get the opportunity.
00:18:22
Speaker
Not only what type of company or what type of product, but as you pointed out initially, what type of people, type of leaders will get to shape the future of our society and what problems will get solved. So I really wanted to reiterate that because that's the whole reason why I'm doing this and we really want our listeners to understand
00:18:43
Speaker
that this is how you connect the dots and why it's so important that we raise awareness around the Angel NPC and startup ecosystem to begin with. It's so true. It's so interesting. I'm going to say one more thing. I know you want to talk about some males, but it's so important. I am in two different, I spend a bunch of time in two different Angel groups. One is a mixed gender group, maybe bias is more male, like 70 percent male. The other one is all women operators. The deal that gained traction,
00:19:11
Speaker
in those groups are so different. The qualities those groups look for that distinguishes a founder that's going to be successful between those two groups is so different. I cannot state enough how important it is for more women, more of us.
00:19:30
Speaker
to get in the game because I swear we see different problems. We see different characteristics. And I think that's going to turn out very well for us as investors if we're seeking Alpha, but it is so different. I've seen it night and day, so I could not agree with you more. Yeah. Super interesting. Yeah. It's all about diversification at the end of the day. And diversification of thought is a big part of that conversation. Absolutely. Okay. Let's go into the nitty gritty detail, Cheryl.
00:19:54
Speaker
We already played around with IRA for a 1K. And while most of our listeners are indeed based in the United States, we also do have a good amount of people who are listening in from other countries. So I wanted to briefly explain what an IRA is. So to everyone listening who might not be familiar, an IRA is an abbreviation that stands for individual retirement account.
00:20:19
Speaker
and individual retirement accounts allows people in the US to save or rather invest for retirement in a tax-beneficial way, usually by investing in the stock market through mutual funds, for example.
00:20:35
Speaker
And in 2023, the annual contribution limit was $6,500. And in 2024, it's up to $7,000. Now, even if some of our listeners are familiar with how our IRAs work, because they have one or have read up on it before, I actually bet that most of our listeners did in fact not know that you could actually invest
00:20:59
Speaker
in early stage private companies, aka Angel Invest, through your IRA. Cheryl, please, please tell us. This is my favorite geeky thing to talk about. When I started getting into Angel, I was actually doing it to learn how investors think.
00:21:15
Speaker
so I could be a better founder and be a better mentor to the founders I worked with. I didn't think I could write checks. I have four kids. I had two in college. I wasn't working. I was like, I don't have any disposable income to write
Can IRAs make angel investing tax-efficient?
00:21:28
Speaker
checks. If I have money coming in that's not going to my retirement accounts or my expenses, it's going to compete with an Angel check between remodeling my bathroom and going on vacation. And that's not a sustainable way to do Angel.
00:21:40
Speaker
And then I found out I could invest from my retirement accounts. And the reason that is possible, it's always been possible, but it hasn't been easy. And over the last nine months to a year, a number of different services, a number of different companies have started up. One's called Alto.
00:21:57
Speaker
One's called carry, and they let you roll over your existing IRA dollars or make new IRA contributions, but then lets you invest them in alternative assets. And by alternative assets, I mean anything that's not publicly traded on the stock market, not your normal stocks and bonds.
00:22:13
Speaker
I will point out, and this is important because a lot of your listeners are younger, angel investing is already a super tax advantage asset class. There's a thing called QSBS. I'm going to get super geeky on you, but if you invest in a startup and you hold that equity for five years, you won't pay federal capital gains tasks on it. And in many states, you won't pay state tax. So it's a super tax advantage asset class to begin with.
00:22:39
Speaker
However, it often makes sense to angel invest from your IRA if you're older and you've been saving in that IRA. And that's where your investing dollars are. Everyone in their portfolio, no matter how much or how little you have, wants to create a diversified portfolio.
00:22:56
Speaker
Alternative investments should be anywhere between 10% and 25% of that portfolio, no matter where your money is. For me, IRA investing for Angel was so attractive because I had been a good little adulter my whole life and I had my assets in there. And the money that was in there had the characteristics that I needed for Angel investing.
00:23:17
Speaker
It was untouchable for a long time because you're not going to see liquidity from your angel investments for 10 or 15 years. It was evergreen. For me, I had saved up a lot over a long period of time. For most people, they deposit in there every year so I could make a consistent set of investments.
00:23:34
Speaker
year after year to build that diverse portfolio and really stick with Angel because that's how to build it into an asset class. And honestly, that money sitting on my retirement account wasn't bringing me any joy. It was just sitting there. It was like ETFs and bonds or whatever.
00:23:49
Speaker
This was a way I took all that good adulting and I turned it into something that was joyful and helping my professional development and helping me meet new people and helping me support the future I wanted to see. So it's great when you get older too, you've had a bunch of jobs. So I'll have my main retirement account, but I also had all these rogue little IRAs for my two-year stint at Adobe and my two-year stint at Yahoo and the year I spent at E-Trade.
00:24:16
Speaker
I took those rollover IRAs and I first put them with this company, Alto, who allowed me to invest in startups on AngelList, then moved it over to this company, Carrie, who's letting me invest in any alternative asset I want. So it doesn't make sense for everyone. It makes sense for certain people. And it's been a big aha for folks that don't think they have the day-to-day money.
00:24:38
Speaker
to Angel Invest consistently, but they realize they're sitting on this pile of money that just needs to be invested and sit there for a while. So I think it's been more of an empowering, holy moly, I do have the budget for this moment for folks, but I wanted to carefully talk about the tax.
00:24:54
Speaker
advantages and disadvantages, especially for a younger crowd that doesn't have IRAs from the last two decades floating around in small dollar amounts. But for those of us that do, it's a great way to get started. Take that, you know, two years of your 401k rollover from a job you had 20 years ago, put it into Alto and start angel investing. See how it feels. It's a great and easy way to get started. Let's sort of answer your question about what you wanted to know about IRA investing and how to do it. Absolutely. And I think
00:25:23
Speaker
the fact that there is more and more companies who are entering the space. I think it's just like so interesting to watch because again, we're witnessing this new trends emerge and it's always fun and exciting to be an early adopter and not, not everything might work a
Financial advice for young investors
00:25:40
Speaker
hundred percent. We all know early products, there's bugs or whatever, but just getting your hands dirty and play around with it again, goes back to learning by doing, I think it's, it's just.
00:25:50
Speaker
So, so exciting Cheryl. So you're mentioning obviously for, for those folks who have a bunch of different retirement savings accounts sitting around and that's a good amount of money that has accumulated over time. If you were, let's say in your mid or late twenties now, and you just started contributing towards your 401k or your IRA, just like a few years ago, how would you think about getting started in this space?
00:26:16
Speaker
I would honestly, and I'm going to talk like your mother now, contribute the max you can to your 401k because it grows tax-free and there's a thing that no one teaches you about early is compounding interest. That money, even invested in the stock market, it's safe, it's easy, put it in an index fund, that money is going to double every eight to 10 years without you doing a thing. That's mind-blowing. Starting early really matters.
00:26:43
Speaker
Just carve a little bit off, pay yourself first. I had a whole bunch of kids early and I didn't do that. And oh my God, once you see how the math on compounding investments work, you're like, well, shoot, I should have put away a few thousand dollars. Then it would be worth a fortune now. It'd be so much easier.
00:27:00
Speaker
Start with the basics. Don't try to jump to angel right away. Start doing it and get the habit down of throwing that money in there. Make sure you have your FU fund of safety cash. And if you're younger, then figure out angel investing. But when you think about angel investing,
00:27:15
Speaker
Some of it is your investable capital that you're building well thought of, but you can also think of it as part of other budgets. For me, it's part of my shopping budget. Let me be honest, right? I don't need a new pair of shoes. I need to invest in a new startup. That's just as fun. It's part of my professional development budget. What was I going to spend to benefit myself this year?
00:27:36
Speaker
Oh, I'm going to put a little bit of that towards Angel because I'm meeting people and I'm networking and I'm learning stuff. So if you're earlier in your career, I would say don't be confined to think about it, that it's just your investing dollars. It can be other budgets as well. Angel is shopping. I love that because
00:27:52
Speaker
When it comes to developing an abundance mindset, when it comes to managing your personal finances and investing, mindset shifts and rephrasing things for yourself is such important.
00:28:09
Speaker
And I love that you brought up compound interest and I don't even remember how many times I've said this before in this podcast, but I actually used to have a pretty bad relationship with money. When I was younger, a teenager, I was caring a lot about designer clothing and always wanted to go shopping and.
00:28:29
Speaker
It was for my first full-time job out of college was living paycheck to paycheck, was not contributing to my retirement account whatsoever. Didn't even know how all of that worked. And I figured like, Hey, I'm in my early twenties. Like it's way too early for me to start thinking about retirement. And then it was like age 23 or 24. That's when I started to learn more about the power of compound interest.
00:28:54
Speaker
And it's funny because yes, you've heard of compound interest before, likely in school and math class at some point, right? But like it's always so theoretical and it's not until you actually get to apply it to real life scenarios and play around with a compound interest calculator on the internet, for example.
00:29:13
Speaker
You see the exponential growth and you see how in the first five to 10 years, it's still pretty slow. But once you had year 20 and year 30, 40, all of a sudden, your share of compound interest grows significantly. And that's when I finally started to realize, oh my goodness, like if I just saved an additional, let it be $100 a month or $500 a month or $1,000 per month, instead of investing that money into
00:29:41
Speaker
material things, things that don't necessarily add value to my life. That is so, so powerful when you invest that money and let it work for you instead. So very, very good advice for everyone. That money, that little bit upfront turns into freedom later and optionality and choices when you get to be around my age.
00:30:02
Speaker
Exactly. It's not about the money itself. It's about money being a tool that allows you to buy freedom and time. Cheryl, I mentioned this to you before.
Making investing accessible and fun for women
00:30:11
Speaker
We went in person for the first time and earlier as well. I love your website. It's so cool for all of our listeners out there. We check it out.
00:30:21
Speaker
on letsplaymoney.io. We'll also make sure to link to it in the show notes so you all can check it out. I love the neon green, I love the bold, I love the unapologetic statements, overall tone, I just love everything. And I also love that you often refer to your work as the process of
00:30:41
Speaker
Taylor-swifting early-stage capital. Curious to hear from you, Cheryl, why do you think this approach and this language is resonating with so many people, especially women, as you pointed out earlier? Yeah, great question. I mean, I think we're saying what folks are already thinking and feeling deep inside, but not sure they have the permission to say it or act on it. The gatekeepers have made
00:31:06
Speaker
financial things and investing seems so serious and hard. And you know what? It's not really like whether it's angel investing or an ETF, it's not that scary. It's not that hard. But more than that, I mean, I think money should bring joy.
00:31:24
Speaker
We work for it. Yes, if we can create wealth from it, that is great. But that wealth should have joy in the process. And we're all so busy, the more we can make our money multitask for us. Yes, earn me a return and.
00:31:39
Speaker
and educate me and help me meet new friends and build me a network that I can find my next job from. If we can make money multitask on that in our busy lives, that's a total win. The returns that we should look at from our money are not just financial.
00:31:54
Speaker
that ROI can be a larger ripple of impact in the world and in our personal lives. And I just deeply believe that. Maybe it's because I've had all these kids and big jobs and like nothing in my life can single track it all needs to multitask. So I think that's a piece of it. And I think the other piece of it, we wanted something that made it and spoke to what I think we all feel inside because particularly as women,
00:32:21
Speaker
We are already better angels than we know we are. Angel investing is about picking the outliers. We see different problems. We resonate with different founders, strengths. This is one place that we are not the normative. We are not the bulk of check writers. So what we see and what resonates with us is more likely to be that outlier. And we should step into that. That should be the normal. The outliers in this space are normal.
00:32:46
Speaker
as women. Boom, mind-blowing, better angels than we already know. And I do believe like the Taylor's lifting piece, I mean, come on, if we show up as our authentic, confident selves, even with small checks, that money pulls together. And with that, we can move whole industries. I mean, seriously, look at the NFL, right? Taylor Swift shows up, the NFL, it's a thing. We can do that as investors.
00:33:10
Speaker
just coming in and mass with our particular confident point of view and a little bit of money. So I'm glad you love the site. We had so much fun with it and it makes it such an easy business to build and run because it's our authentic voices. If I had to put a fake financial voice on, it wouldn't work.
00:33:27
Speaker
Yeah, I gotta tell you, it really shows that you had a lot of fun putting this website together. It screams, yes, there is someone who is just so deeply convicted in what she's doing. She truly believes in that, but she's also having fun while doing so, and she's very unapologetic and bold about it and is very confident.
00:33:45
Speaker
Especially, I saw the website first before I ever met you and then I met you in person during the first time a couple of weeks back. I was like, okay, all right. Like this match is up. I can see who built this and why she built it and why this website turned out the way it did. And it's just beautiful. And you also just brought up the topic of authenticity. I think it's so, so important when we dedicate our lives to building something, no matter if that's a play money or.
00:34:13
Speaker
In my case, this podcast, or if you have a side hustle, or you're also starting a company from scratch, there might be some future first-time founders listening to this episode, right? No matter what, as long as you show up as your most authentic self, I think there's not a whole lot that can go wrong. Yes, might not become a billionaire or have
00:34:34
Speaker
an immediate exit right away, but at least you can say you stay true to yourself. And usually when people see that you show up as your most authentic self and you actually care and you're committed, that usually attracts possibilities and it usually opens doors. And I think that's very much the case for you.
00:34:52
Speaker
Oh, I love that. It does. And hopefully we can inspire that in people. They can feed themselves and their own confidence reflected there because that's the money moving angel. That's the outside. That's why we're going to win. And I think this is something we talked about as well throughout this conversation. But we haven't necessarily used that word yet. And that word that I'm referring to is community. On the show, we talk about community and community building a lot and the importance of women supporting women.
00:35:21
Speaker
And I believe that a lot of women are craving community, especially when we're starting out with investing, no matter if it's investing in a stock market or startups. And you mentioned earlier, you've met so many incredible people throughout your experience as an angel investor. And like the same for me, having moved to New York.
00:35:40
Speaker
About two years ago and complete, I had to rebuild my network almost from scratch. Didn't really know anyone in the BC, Angel, our muralist base. And all of a sudden there's all of these amazing women, founders, business owners, you name it. And it's so vibrant and you see the same people oftentimes at the same events, both in person and virtually. And it's so great. Curious to hear from you, Sharon. What is DWAR strategy for community building and scaling play money's impact over time?
Supporting smaller communities through diverse investments
00:36:10
Speaker
Great question. We thought a lot about this. I have a passion about putting money in motion from founders and to create wealth. But I didn't want to be a VC. I'm just not a company picker. I don't want that as a job. That doesn't get me excited. I'm a product builder at my core. And we thought about that with PlayMoney. Did we want to be community builders? We're product builders.
00:36:31
Speaker
not necessarily community builders. I've built communities before, but I had that Kickstarter starter following that still follows me today. People I met 12 years ago because they backed my Kickstarter. There was something so powerful about that. But when we thought about how to really scale this, the place that we were unique is in the ability to build a product. We believe that on the community side, we need to be
00:36:55
Speaker
shelling point for those communities. But smaller communities were going to be more powerful, particularly when it comes to money. Your best place to talk about money and investing might be with your chief cohort, or it might be a professional organization you're in if you're a doctor and everyone in the organization is doctors. We had one woman we met when we were in New York and she was like,
00:37:18
Speaker
I have a group of girlfriends and all our kids are graduating from high school and I'm so sick of talking about their SAT scores. Can I bring them all and play money so we can hang out every Tuesday and talk about angel investing? Give us a shelling point, give us deals, give us an event and something to talk about so we can create
00:37:36
Speaker
those moments of community that we so crave and inject them with something new and interesting. For her, it was like, I'm so sick of talking about the kids and their damn SATs. We're super smart and intelligent. Let's go do this thing. So when we think about scaling it, we want it to be a deal flow platform, maybe a little bit of an event night, but we want everyone to form their own communities.
00:37:59
Speaker
We can inject some education there, but people are going to hang out with the kind of folks they want to learn with, the kind of folks that think like them, the kind of folks that are local to them, people they've known forever. We want to encourage more of that instead of trying to centralize it all to us. I think in the process, clearly we have a strong vibe in our brand, and so I think that will inspect
00:38:21
Speaker
all of those little groups and sort of a Uber kind of community way. But that community organizing and pulling groups of people together, I would love it if we could make that happen on a more local and just whatever feels right to you versus creating one big mega group.
00:38:37
Speaker
It speaks to the introvert in me. It's, it's crazy because earlier growing up as a kid, a teenager, even all the way into my early 20s, they're definitely identified as an extrovert. And now as I grow older, I feel I become more of an introvert and I very much prefer.
00:38:55
Speaker
small group gatherings as opposed to joining a huge group of people and doing a bunch of small talk. Hence why I love doing this podcasting because I get to have these really meaningful and usually very deep conversations one-on-one with another person and it cares more to my personality. So that's why what you just mentioned really resonated with me and.
00:39:17
Speaker
There's different smaller communities that have different needs or different stages of their angel investing or general, like overall investing experience, right? And you cannot just make the overall assumption that everyone is starting out at the same place. Like someone might start down here, the other person has already, I don't know, 10 years of investing experience under her belt.
00:39:39
Speaker
So as a love opportunity for you all to provide that level of flexibility and really give people the opportunity to make it their own while also being able to tap into educational resources, attend events, and still feel like you're part of a bigger community, but you can truly make it your own by looking at it and just like hopping on a call with a bunch of your girlfriends.
00:40:03
Speaker
That's how it works. I mean, it's a giant experiment. We're feeling it out right now in beta, but it feels like what's most authentic to us. It feels most authentic to the kind of business we want to build. And if we can affect all of those little groups, a little bit of our vibe and a little bit of our confidence, that would be fantastic. It feels like a good place for me. So hopefully it works.
00:40:25
Speaker
We're learning as we go. Oh, absolutely. And we're going to have another conversation on a couple of months from now and you will be able to share so many learnings, what worked, what didn't work. A big part of, as you know yourself as a two-time founder, it's an emotional roller coaster. You have to pivot sometimes along the way and that maybe.
00:40:43
Speaker
You'll play money and five years from now will look completely different from what it is today and what you had initially envisioned, but that's also okay. Entrepreneurship and the startup equity system would be super boring if everything was super predictable and we could look into the future and knew exactly what was going to happen five, 10, 20 years down the road. So.
00:41:03
Speaker
that's important. I think we did the right things by picking a problem we were super passionate about. This could be the last act of my career because this is the space I want to play in and we started from a point of our strength on building product and if the business needs something that's not that, we know how to find great people.
00:41:20
Speaker
So it'll be a fun journey. I'm excited. Cheryl would love to ask you one final question. Imagine you had the power to enact a single universally binding law that every organization must obey and it needs to be specifically designed to significantly uplift women's economic status.
Advocating for parental leave to uplift women
00:41:42
Speaker
What law would that be, Cheryl?
00:41:44
Speaker
This was great because you gave me the questions before, so I had time to think about this. But it engendered a great conversation at my house last night thinking about it. I'm going to go with that bougie European kind of parental leave, proper childcare and parental leave. And see maternal leave said parental leaves, but proper childcare and parental leave, it
00:42:05
Speaker
helps so many people across the board and will yield bigger results and returns in the scheme of things for women. That would change a whole bunch of stuff. And a lot of places have a lot of nice things like that. So there's a model to use. It's not a crazy thought there. Just one nice thing for us here.
00:42:25
Speaker
be up as a European myself, I can very much agree with that. I think when I moved and I'm pretty sure I've mentioned this in a podcast before, but when I first moved to United States for college and at my alma mater took university, I had a part-time job and there were amazing women that I collaborated with and one of them got pregnant and I think she only ended up having like
00:42:48
Speaker
six or eight weeks of attorney leave. And I was just, that was someone coming from Germany. That was just mind blowing to me. So I love that you, that you brought this up. There's still a lot that needs to be done in this space to, to ensure there's going to be true equality and especially women who let's be real are usually on average still the primary caretakers.
Conclusion: Empowering women financially
00:43:13
Speaker
have the opportunity to focus on their careers unapologetically, invest in self-care, demand what they deserve, and not have to feel guilty about it. Anyway, that's a conversation for another day, but I just want to say big thank you to you, Cheryl, for having joined me on the show today. This was such an enlightening conversation. I knew this was going to be amazing, but it
00:43:38
Speaker
definitely exceeded my expectations and I cannot wait for our listeners to listen and learn from you and check out Play Money. I love it. Thank you for giving me a stage and having such smart questions and letting me talk about things that clearly I'm so passionate about. Amazing. Amazing. Thank you. Thank you. I'm Tamina and I'm extending a heartfelt invitation to you as we join forces in reclaiming economic power for women in a world that is often structured against us.
00:44:09
Speaker
We'll dive into the minds of accomplished female leaders, investors and entrepreneurs to equip you with the confidence and knowledge to build wealth for yourself and other women. So buckle up, get ready to learn and be inspired to take action.