This week, Investor Aseem Datar is talking with Will Rush, co-founder and CEO of Stack, a teen crypto platform to educate a young crypto-curious generation — and their parents — about responsible investing. After working at a company, building a banking app for teens, Will took his decade-long experience in securities and finance and applied it to crypto and Web3. He saw the excitement and curiosity that teens had for crypto and knew he could apply his experience to create a world of responsible teen crypto investing.
Stack has managed to balance education and access for both parents and their teens in a way that the younger generation is actually appreciating and connecting with. And Will is maniacally focused on the education portion. Not only because he is a soon-to-be parent himself, but because in what he calls the Wild West of Web3 and crypto, he says somebody needs to be the good guy. To help continue that project, Stack just landed $2.7 million in funding to continue developing its platform. And Will’s advice for every founder — “You need to have slime on your face” — a reference most of us millennials will understand, but you’ll have to listen to see how Double Dare relates to launching a startup.
This transcript was automatically generated and edited for clarity.
Aseem: Hi, everybody. My name is Aseem Datar, I’m a partner at Madrona Ventures, and I’m excited to have Will Rush, the CEO of TryStack.io. Will, welcome to the show, and I know that congratulations are in order.
Will: Thanks so much for having me, Aseem. I’m really excited to be here. It’s been amazing working with you guys and the Madrona Venture Labs team as well. We’re very fortunate to have you in our corner.
Aseem: I’m excited to talk a little bit more about Stack and make people aware of what you’re building. I’m very excited, and it’s amazing to partner with founders like yourselves who have a big, bold vision. But before we get into Stack, I wanted to understand a little bit about your background and where you are coming from. Tell us a little bit about your story.
Will: you know, I’ve been in securities and finance at some level for over a decade. In the early part of my career, I worked with companies like Charles Schwab, E-Trade, TD Ameritrade, and a lot of the old brokerages and traditional finance guard. And then I reached that point in my career that I think a lot of people do where I’d been doing one thing for a long time, and I wanted to lean a little bit more into the early side of things and startups. So, I went back to school. I got a master’s degree up here at UW. And while I was getting my master’s degree, I worked part-time at another venture firm now called Fuse Venture Partners — at the time, it was still Ignition Partners. And that was a really fun company and environment to work with — and all of their portfolio companies and founders were a great way to get my feet wet with this startup world. And then, at some point, I met who would become one of my favorite mentors ever in my professional life, which was Eddie Behringer. He was coming off of a recent win with Snap! Raise, which had just done its private equity exit. And he just started Copper Banking — I think they had three or four team members at that point. It was himself and his co-founder from Snap! Raise and one or two others. But he was also thinking, at that time, what it would be like to build a brokerage and stock product for teenagers. The thesis of Copper was to build the finance and banking app for teenagers that was built for them instead of their parents or somebody else. And so, it was really fun. It was a great product to be a part of, and I learned so much working directly under him. And then eventually discovered this thesis for Stack.
Aseem: You know, this leads us to the obvious next question, which is the inception of the idea around Stack and really trying to understand what patterns you saw while at Copper while being at the VC firm. I want to dig deep into understanding how that idea came to you. What are the macros in the world that you saw? I want to dig into “your why,” as they call it. Why did you build Stack?
Will: Oh, man. I mean, I think it really started from understanding the last 10 years in finance and FinTech. We saw companies like Robinhood outside of the 2008 financial crisis do an amazing job of democratizing access. And they did that by allowing you to trade $1 of any stock you wanted with fractional shares and do it commission free. And so, of course, that introduced a lot of new people to the stock market. But with democratized access, I think there was a huge lag in education. And so, being at Copper, being able to impact young people who were at the very start of their financial journey, the impact that you can make and the habits that people form at that age, you know, they absorb things like a sponge, and it was cool to see and be a part of those stories. While I was at Copper and I was researching our stock product, it became abundantly clear to me just through some of the AB tests that we would do where we would literally change one word “stock” to “crypto,” and all of a sudden, our engagement on things like Instagram would just fly off the radar. And so, I think there was a story there. There was a story about this zeitgeist behind crypto, this excitement, this curiosity with the youngest generation. And could you be the good guy in that world?
That was really like, where the thesis for Stack started and how we got to do what we’re doing now. I think there’s so much to unpack, which is how you educate successfully. I think a lot of parents hear teen crypto, and their first thought is, “Whoa! My teen doesn’t even have a stock account.” Or, ” I don’t know if I want to get my teenager involved in Web3 or crypto.” But the reality is that a lot of the teenagers we’ve found are hacking their way into crypto. They’re using their parent’s driver’s licenses to get a Coinbase account. They’re going over the law in a lot of ways to do this. And if we could create a bumper lane, if you will, that to us was a really compelling solution.
Aseem: Three things that you said stood out for me. One is this whole notion of democratizing access, right? If you go back a few decades, not everybody was trading in securities. Not everybody understood what it meant to be, for lack of a better term, owner in a company and bet on the growth of that company or that enterprise. And that’s changed over, I would say, even the past couple of decades. I think the second thing that you really mentioned, which was powerful, was this wave of learning and educated investing and guidance. And in the world of crypto, I think it’s more true than ever that people are just trying to figure this out. And especially teens, who want to latch onto this wave, but at the same time, kind of don’t know where to go. They’re discovering it as most people are. It’s fascinating that you are the on-ramp or the guardrail like you mentioned, to educated investing. Because this is going to happen with or without, I would say guides or mentors. And the third thing that you mentioned, which is fascinating to me, is even parents are learning. This is where I love the theory and the thesis behind what you guys are building, which is educated access, educated investing, and providing a friction-free on ramp to growth. So, tell us a little about what’s on offer today with Stack and where people can go to try it out.
Will: Well said, on so many fronts, there is this huge opportunity with what we’re building to, I think, tie two wants of our two users. There’s the parent user, and the want is education. The other user is a teenager, and the want is access. And one is hacking their way, and the parent who wants both themselves and their teenager to be educated really doesn’t have a lot of places to go right now. Because there really just isn’t that much education in crypto in general. We’re really living on the edge of the most cutting-edge area of the financial sector. The offering that we have now — our app is live on Google Play — it is set up so that a teenager opens a UTMA account, which is the Uniform Transfer to Minors Act. That requires a parent to be a cosigner on the account. And it allows teenagers to have legal access because if they access Coinbase or Robinhood or any of those other platforms that are out there right now, they’re actually living above the wall, meaning they only allow 18 or older users. But we allow legal access for teens. And then there are a lot of other really cool things about the app. So, for one, a parent can set approval limits. That means they can say, “I want to review everything,” “I want to review trades that are above $50 or a hundred dollars,” or “I want to give my teen the keys, and I trust them to go make good decisions.”
The second thing that we do a lot of is, like we’ve talked about a lot — education. How do you balance the education element and teen who is on TikTok and a lot of trends that they see are evolving in a matter of minutes or hours. How do you get their attention? How do you actually win in this education world that obviously very few people in finance have been successful with? And I think the way that we have chosen to win and really what we’ve learned about teenagers over the last 18 months is — it has to be bite size. It has to be tied to just-in-time learning. So that means, if you’re about to buy Bitcoin for the first time, you want to know about Bitcoin right then, and how can we win that moment? And then there’s the third piece of it that has proven successful in a few other startups, which is the learn-to-earn model. And that means you actually get benefits, and for us, you get fractional amounts of crypto if you teach yourself about it.
To a parent user, I think that third element is really important because we are doubling down on education from day one — by saying, we will give you free benefits, rewards, whatever you want to call it, via crypto, just for educating yourselves. There is a new offering that we’re going to release later this fall that I think will be by far the most exciting offering that we have to date. And it really plays on both a parent wanting education and a teen wanting access, and really how to balance the two of those as thoughtfully as possible. And also from a lot of the early engagement statistics that we’ve seen from our user base on our app.
Aseem: I think one of the things that stands out for me is the UTMA license you guys were able to get, and that’s really the foundation of how you’re approaching responsible investing. That’s awesome because it’s all about providing that guided education path for somebody to take control of their own destiny in a responsible way. I was curious what are you hearing from the teens — or, as I call it, the entrepreneurial generation — what are you hearing as they’re using your platform?
Will: We’ve learned an immense amount from teens working with them. I mean, we literally work side by side with them and in a lot of capacities — we’ve physically shown up to high schools. We’ve physically sponsored events. We’ve digitally sponsored events. What they’ve taught us over that period is you’re only going to command a very short period of time, and that includes education. That includes even if you reward them through something. And so, how can you win small moments that have a big impact? So, we’ve built that into our education content. We expect our team users to be spending an hour between 30 seconds and 90 seconds on the educational module of our app. But if we can do that consistently a few days a week or even every day of the week, I think that’s where you win.
The second thing that we’ve learned from teens is, in this world of technology, they’re highly capable. And I think many products built for kids and teens infantilize them a little bit, and this generation is different. As you said, they’re the entrepreneurial generation. They identify as entrepreneurs. A lot of them have side hustles. High school is different, and we need to recognize that, and we need to lean into that because they’re highly capable. And if you give them the right tools and the right guardrails, I think they’ll shock the heck out of you with what they’re capable of doing.
Aseem: Which is amazing. I think there’s so much to learn with this new way of consuming content, consuming education. You’re kind of on the bleeding edge of constant evolution from the product side of things. Shifting gears a little bit Will, tell us a little bit about the recent economic changes and the impacts that the markets are having. Have you seen any changes in terms of how people are interacting with Stack, and how they’re thinking about it? I mean, you guys just launched, but I was curious about how that’s playing into the minds of your customer?
Will: Well, I’ll say this, A) we’re incredibly fortunate to have launched. And we did because we launched after the down cycle. If you believe in the thesis that crypto is going to go back up, which I think, you know, anybody that’s getting involved in it likely does. There’s a good chance that our user base is getting in closer to the bottom of the market. I mean, I look at somebody like Robinhood, that was born in the shadow of 2008. And what Robinhood did well was they built with a diehard user base. And then, when the market started to catch fire again, that’s when you saw their user base take off. Not saying that we’re waiting around for the market to catch fire again. I think there will be another one of those natural upswing moments when there’s a lot of curiosity, crypto’s back in the news all the time, and people are talking about new coins, and they’re talking about Bitcoin or Ethereum and everything else. But in between now and then, we are really living and breathing the customers that want to be doing crypto right now. And they want to do crypto for, I think, a few reasons. Number one, they know that not only is there obviously crypto the investing product, but there’s the blockchain, and there’s the technology behind crypto. And there are so many other use cases, so many other industries and companies that are building on the blockchain as a technology that can be learned on our platform and can be learned through crypto. Because crypto is the currency of this technology. So, I think we’re really leaning into that. That user base tends to be gamers or highly tech-oriented. They certainly have a certain customer profile that we found over the past few months, but that’s really kind of where we’re living and breathing right now.
Aseem: Right. That’s so awesome on so many levels. Wanted to ask you a little bit more about the product itself. So, what can teens do with Stack today that no other platform offers them?
Will: So, number one is just legal and safe access for teens and their parents. I mean, we are one of the very few investing platforms — even if you open this up to stock products as well, it’s a small niche game, the under-18 finance and mobile app game. And we were the first ones to open in this under-18 arena specific to crypto and Web3. Number two, something that you get out of it just indirectly through a UTMA account is you get tax advantages. You can earn up to $2,300 tax-free on our platform because you have a UTMA account. Whereas you go earn on Coinbase under your parent’s account, and you’re going to get charged 30% or whatever their tax rate is. And then lastly, it goes down to a product built specifically for teen crypto rather than a Coinbase or a Robinhood. What we think about there is we limit the coins on our platform. We do a lot of vetting of what currencies are on there. We vet based on market capitalization, we vet based on trading volume, we vet based on a lot of characteristics and nefarious activity. And so, we’re tracking so that the top-of-the-funnel decisions we make about our product and app is making it safer to trade in. And then lastly, we also don’t do crypto on and off ramps, and I think that is an essential decision for us. Crypto on and off ramps is where all the fraud and scams happen. It is somebody tricking you into or hacking your wallet password and transferring assets on an immutable ledger that you’ll never get back. So just by disabling that, I mean, there’s no reason for our users to be sending crypto assets off platform right now in our use cases. And so, we can just guarantee safety there. I think that’s obviously important.
Aseem: I mean, I remember the days when, when you first got a bank account, when you first got a credit card, and like the world opened up. Right. And with that comes a lot of nefarious activity and risks. What’s amazing, as I’ve learned working with you, is you guys are trying to minimize all risk that there is out there from a fraudulent activity perspective. Now, yes, there’s always risk in trading, but at the same time, you’re giving them the tools and the platform to do it in a responsible manner.
Will: Totally. It is the Wild West, but it’s in need of a good guy. And we hope to be one of those good guys that can create a safe place for you to trade. And for you to learn.
Aseem: So, shifting gears a little bit, tell us a little bit about how you’re reaching teens. I mean, so much of what teens do is driven by social proof, right? I mean, yeah, if my friends do it, then I’m going to latch onto it. I’m going to learn how to do it. How are you approaching the community angle of your focus — is there a community angle?
Will: Oh my gosh. It is essential it’s everything that we do. We have an ambassador program, which you’ll see right on our website. And that ambassador program now has a little over 200, 250 teens representing 200, 250 high schools. Most often, they are the president of their finance or investing club at their school. And what they do is they work directly with our team, and there are two aspects to it. One is we come in and do a financial literacy workshop with them, which is incredibly powerful for us, whose mission is to educate this next generation of kids. Meanwhile, the curriculum in their own high school certainly cannot keep up with crypto and digital assets in this world.
And so, we can do a lot of cool education there through this extracurricular environment. And then the second thing that we do with them is give them opportunities to earn money on the app. And they can do it in a lot of ways. So, they create some of our TikTok content. We did a challenge where we sponsored a group of teens’ side hustles for the summer. And so, we had teenagers that created designs for iPhone cases and sold them on eBay. And we had teenagers that very entrepreneurial collected golf balls, you know, they lived on a golf course, and packaged them and sold them. And so, there were just a lot of cool stories that came out of that. And they video blogged the entire thing. Just creating those powerful stories of this teen community so that teens can see their peers, see the amazing things they’re doing, and understand that Stack, as a brand and a platform, is a place that is celebrating that. And I think that’s fundamental to who we are.
Aseem: Yeah, that’s so cool on so many levels this ambassador program can just be the beachhead of what you’re trying to achieve. And I think with that comes social proof and with that comes interest and awareness. It’s so cool on so many levels. You know, as a parent of a 9 year old, soon to be entering teenage years. And it’s almost scary to think of. So tell us what’s on the mind of every parent, tell us more about what your journey has been, how you’re discovering that. And frankly, is that going into how you’re thinking about product?
Will: I’ll admit right now that we have a lot of work to do with parents. We are starting to be good listeners of parents. I’m actually entering the parenting arena in a few weeks myself.
Aseem: Yeah, congratulations!
Will: Thank you. Thank you. I’m constantly thinking about what type of world I want to create for my own children. And I know that’s on every parent’s mind. So being the good guys and sharing the message that we are the good guys that, we’ve taken a lot of steps to create the best place for a teen and a parent to go be a part of this kind of crazy world of crypto and Web3, I think is a huge message to carry. We have started doing some more bespoke programs similar to our ambassador program but for parents. And then the second place that I think we’re spending a lot of time, which I think is just as important as parents and carrying the baton as teachers. Educators can be, I think, a really interesting part of our strategy.
I’ll say this, we didn’t really hit this light bulb until recently, but we had probably, I’m going to say 10 to 12 educators specifically send our website’s email to reach out about us educating on crypto and whether they could get their class involved in our platform and wanting to know how it worked. And from that, we’ve realized that there really is this cool opportunity to share stories through the educational mode of the world to parents because who do parents trust the most? They trust teachers. And so, if we can find a way to create some really cool storytelling of teachers being a part of our platform. And using it to educate kids in a place that curriculum just can’t, I think that could be a powerful way to celebrate parents and their needs and wants, which obviously fall into education.
Aseem: Yeah, I really like it. I mean, I really like the use of the word curriculum. Because at the end of the day, your kind of giving them a very curated set of learnings that you can then apply to real-world scenarios and start trading. And, you know, you’re bang on when you talk about teachers and in some ways, you know, parents are teachers, but in, in this scenario and in, in this new world, parents are also on the educational journey, and they’re learning alongside. Talking about learning, your first-time founder, you’ve had amazing experiences at a different company, you’ve been at a VC firm — what’s been different so far as an entrepreneur? What have you learned? And I love asking this question — what has been the “aha moment” — if there is one?
Will: Oh my gosh. I mean the founder journey, I tell, friends and, and even like early founders as they’re starting their own journeys — I say, I think being a founder either spits you right back out. Or just lets you fall into this ocean of loving every single day of what you do. And it, and it really takes, a certain set of wants and needs out of the founder journey to really embrace it and love the job. It has made my career come alive in so many ways. The six months that I both created every strategy and then executed that strategy, I think, is one of those unique moments in your career because we all don’t get enough time to just spend on ourselves, especially when you work at bigger companies and you’re part of the machine in a lot of ways. And so, that six months, for me, to really go back and be honest with myself and not tell myself any stories, say, “what are you great at?” And “what do you need other team members to come and do a really great job of?” It tells you lessons about yourselves, you know, just in that honesty that I think is beneficial, not only to your career, obviously, but just to me as a person. I find myself grateful for a lot of those lessons early on and celebrating a lot of those things, the bigger we get and the more people we add to the team and all of those good things.
And, and shout out to, you know, my two co-founders who round out my skill sets incredibly well. We had a discussion earlier today, in fact, about some areas that each of us feels particularly strong in and how we can continue to celebrate those in all of the strategies that we’re running.
Aseem: We’ve had the fortune of working with, you know, both Natalie and Angela as well, and I think we can see the team coming together and the sum of parts making the whole so much better. Right? Because at the end of the day, I think you’re complementing each other well. You know, you’ve got your strengths, and the team has theirs, and I think it’s so amazing to see the humbleness, the drive, and frankly, the passion for the space all get married with your skills that then take you along the journey of achieving something really, really great. The common knowledge around talking to founders is that there’s always one thing on their mind that they’re maniacally focused on — what is it for you when it comes to Stack?
Will: The number one thing, which I’ll just reiterate like a thousand times probably, is how can we more meaningfully educate? And so, we’re constantly obsessed. I mean, where my skillset falls, a lot of the time is actually in our product and designing it thoughtfully and listening to the data and listening to users and, and really celebrating those users.
We had a fun conversation about our marketing approach right now. And we talked about how we need to create the Stack feed to mirror the exact profile of our user. And how do we make the Stack feed look like a 16 year old that’s curious about finance and has certain behaviors and patterns so we can really live and breathe the content that they’re seeing and create meaningful educational content, create meaningful marketing content, create meaningful product content, all of that stuff. I think just celebrating a lot of that in high-quality content where I think a lot of finance apps send you to a blog or send you, you know, off app to something else. We can do a lot of good stuff there. So that’s the one laser focus that I have is winning that specific space of our app.
Aseem: And so much of what you’re seeing is actually reflected in the approach that you’re taking. The way different people consume content has changed so much over the years. Like we’ve gone from news feeds to RSS feeds to blogs to articles to Twitter to TikTok now, and I think it’s amazing, you know, how meeting people where they are is the approach that you’ve taken. It’s the natural way of how teens will learn. It’s exciting to have seen the work the team has done and in working closely with you seeing how much we’ve learned as a firm in terms of the approach you’ve got to take and you’ve got to change. It’s both enlightening and fascinating at the same.
So, kudos to you and your team for always being hungry and always being on the lookout for what’s around the corner and how you can make it better and how you can strive to achieve that curated approach in a way that is very natural.
Will: I appreciate that. It means so much.
Aseem: Yeah. Advice for young founders, Will. Like a lot of people who are in big companies, have ideas, you know, going after a bold vision, thinking about solving it in a meaningful way — what advice do you have for them, having just walked that journey and, and still walking that journey.
Will: Well, number one, I would say is the metaphor I’ve used from time to time. It’s an old show I watched in the ‘90s is called “Double Dare 3000,” and there’s a part of that show where you are going through this obstacle course. You’re given no instructions. And in each obstacle, you have to find a flag, and it’s like stuck in slime sometimes, or it’s in the middle of a slide, or it can be anywhere.
Aseem: It sounds very teenager focused.
Will: I mean, it was a great show. I loved watching it when I was a kid. And why I think it’s the perfect metaphor for early founders of a company is because you’re given very little instruction as a founder because you’re your own boss, all of a sudden. And you don’t have a lot of structure. And all you’re trying to do is find the flag at every obstacle. And that changes every day. Your job changes every day. One day, you’re trying to find money. The next day, you’re trying to find product-market fit. The next day, you’re trying to interview customers. The next day, you’re trying to keep your vendor expenses down. It is a new and different challenge every day that you enter the game. For founders who love it, that’s what they love about the job. But you need to be finding a way to just find the flag. The quote that I throw out there is, “You need to have slime on your face.” You just need to go for it. You’ll be told a thousand times that you’re not going to make it. You’ll get told “No” a thousand times. And to be resilient enough to get through that and to find it in yourself, to get to the next obstacle. I think that’s the biggest thing.
Aseem: I will tell you this, Will — in the context of “slime and your face,” we were enamored by your vision. We are enamored by your tenacity, your passion, and I don’t think that there was ever a question of “No” from our side. You know, without further ado, any fun fact or any fun story that you want to share with our listeners as we bring this to a commencement,
Will: Oh, man. I mean, there’s so many things I, I think there was a moment in the second month of being a founder — and this is when I had taken the plunge, this is my full-time job, you know, I was fully locked in — and I had one of those days where I got a lot of “no,” you know, I was getting a lot of doors closed in my face. And I had sat in my chair for a long enough time that my screen had went black, which meant it had been 15 or 20 minutes or something. And I was staring at my own reflection in my computer, and I just looked at myself, and I said, “oh my God, what are you doing?”
Will: And I think to pick yourself up from those moments, which every founder has them. And, you know, one of my favorite books is “The Hard Thing About Hard Things” because it talks a lot about those moments that he talks about the struggle in that book and how every founder has been through the struggle. I think there’s so much knowledge, and just knowing that others have gone through it, and talk to a good founder, have a coffee with a founder that’s a step ahead of you. The amount of knowledge that you’ll learn and the empowerment that you’ll get. I mean, every time I have one of those conversations, I rip off the warmups, and I get back in the game. And so, I think that’s incredibly powerful, and I’m happy to be that for, for any entrepreneurs out there listening.
Aseem: That’s awesome. Hey, will I really want to, you know, congratulate you on the announcement and on the raises and, it’s fascinating to be able to back someone like yourselves and partner with you and the team in, in really going after a big, bold vision. Because I think this is truly transformative. If you think of it like 20 years down the line, but looking back and saying, “Gosh, we wrote the first line of code and had the first product on the market that actually helped teens invest in a responsible way. And that really created not just good habits, but it created futures.” I think it’s just fascinating that there is so much out there that we could be enabling in a responsible way. And we are fortunate at Madrona to be in this journey alongside you and to continue building or laying the foundational elements of this. So, thank you for your partnership, and I’m even more excited about doubling down and getting to work because the real work starts now in, in trying to scale the product and, you know, deliver a stellar experience.
So, thanks for being on the show and good luck in the future, and I’m sure we’ll be looking back and saying, wow, that that first line occurred, that first staring at the screen that moment was surreal.
Will: I love it. I thank you so much for having me, Aseem. I’m humbled and honored to be a part of the amazing Madrona portfolio. And I know my team is incredibly fired up to go solve this problem. And, as you said, the hard work starts now. And I think we’re really excited to be a part of it.
Aseem: Awesome. Thanks. We’ll talk to you soon.
Will: Thanks, Aseem.
Coral: Thank you for listening to this week’s episode of Founded and funded. If you’re interested in learning more about Stack, please visit TryStack.io. Please tune in in a couple of weeks for our next episode of Founded and Funded.