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Ep 55: Why Upwardli CEO Aaron Gregory Took the Leap from GC to Founder
77 Plays3 months ago
How do you make the leap from lawyer to founder? How do you craft the perfect pitch? What does it take to fundraise effectively? And how far will your legal know-how take you when you’re accountable for every function in the business?
Join Aaron Gregory, Co-founder and CEO of Upwardli, as he shares his journey from general counsel to start-up leader. Starting his career in the highly regulated telecom and fintech industries, Aaron relied on lessons he learned while earning his JD-MBA to start a company that solves the challenges of credit invisibility for more than 50 million people in the United States.
Listen as Aaron discusses how he took on the challenges that all first-time founders face–like pitching to VCs, fundraising, and growing into the CEO role—and shifted his mindset from that of a risk-conscious legal leader to a business-focused operator.
Read detailed summary: https://www.spotdraft.com/podcast/episode-55
Topics:
Introduction: 0:00
Forging a career in highly regulated legal areas: 1:25
Advice to law students considering a JD-MBA: 7:20
Teaching yourself to become comfortable with uncertainty: 9:57
Leaving Remitly right before it went public to found a start-up: 15:10
Unpacking Upwardli: 18:42
Bringing your business to a start-up accelerator: 22:26
Fundraising for your start-up: 27:05
Making an effective pitch: 33:15
Growing into the CEO role: 36:16
Building Upwardli in Milwaukee, Wisconsin: 44:43
Bonus questions: 48:48
Book recommendations: 51:29
What you wish you’d known as a young lawyer: 53:02
Connect with us:
Aaron Gregory - https://www.linkedin.com/in/amgregory/
Tyler Finn - https://www.linkedin.com/in/tylerhfinn
SpotDraft - https://www.linkedin.com/company/spotdraft
SpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues.
Visit https://www.spotdraft.com to learn more.
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Transcript
Understanding Uncertainty in Business
00:00:00
Speaker
I've always been kind of like to play multiple positions. And I really like the intersection of making business decisions in in even areas of uncertainty. I've found like a lot of people would like a lot more certainty than maybe I believe truly exists in the world. um What I think a legal degree helps you to understand is how to weigh uncertainty and kind of like weigh it out.
Meet Aaron Gregory, CEO of Upwardly
00:00:33
Speaker
Want to make the leap from lawyer to founder? What do you need to know? Is it harder than expected? Worth the journey? Today, we are joined on the abstract by Aaron Gregory, co-founder and CEO of Upwardly.
00:00:49
Speaker
Upwardly, which I will have Aaron also explain to us, is like Stripe for credit, making it easy for companies to launch credit products that just work. Before launching Upwardly, Aaron was the general counsel of Remitly, where he led the legal compliance and risk functions up until their $7 billion dollars IPO. He also has passed in-house legal experience and he started his legal career at Denton's and Kelly Dry and Warren focused on federal regulatory matters. Aaron, thanks so much for joining me for this episode of The Abstract. Tyler, it's great to be here. Thanks for
Aaron's Career Journey in Regulated Industries
00:01:25
Speaker
having me.
00:01:25
Speaker
I mentioned that you started working on federal regulatory matters. Maybe we can start there. I think a through line in your career has always been working on highly regulated areas. Has that always been an interest of you or is that something that you just fell into?
00:01:40
Speaker
ah I think it's something I actually fell into. So I graduated law school in 2009. And I did a JD MBA. And my goal was like, I want to be a corporate lawyer. Like, I want to be a lawyer, so I want to do that. But as you know, there was a big recession in 2009. So I graduated GW Law in 2009 and had an offer at Kelly Dryden Ward. And I got to, like many, we got deferred a little bit. And then I get there. I'm like, OK, I'm ready to do deals. And they're like, there are no deals.
00:02:10
Speaker
find somebody So like I found myself, they're like, OK, you can pick. We have all these other practice areas. Just corporate's not going to be one of them. And we had this great telecom firm, a telecom practice. And I was like, that's interesting. like that's There's technology there, which I'm into, and there's deals going on.
Transition to Fintech and Payments
00:02:30
Speaker
So I'll go over there. I didn't love telecom like as a practice, but what I saw as soon as I got there was like the industry consolidation.
00:02:37
Speaker
that was sort of the outcome of the huge explosion of telecom innovation and like the move from analog networks and to to competitive and mobile telecom. It all just happened. And like, it looked like the economy had come through and just leveled the industry. And I'm like, oh, that's interesting. Something big just happened here. So I said to myself like, okay, that's interesting. Like lawyers are well situated to help in those heavily regulated industries. So like,
00:03:07
Speaker
find other industries that are gonna want to do in networks what just happened in telecom and just park yourself there and like I don't know what's gonna happen but like innovation will happen and you can like yeah into that so I did that and ended up going in looked looked around so okay well payment networks and electric networks are going to want to be go from analog, like highly controlled to like digital open. And so I'm like, okay, I started a payments practice at my firm in like 2010. The firm thought it was crazy. Like, there's no clients. What are you talking about? I'm like, they'll be clients. Just wait. These clients are very good. And I'm like, there' go they're they're just not there yet. But I ended up like becoming a to ah ah fintech specialist before that was a thing.
00:03:57
Speaker
and That's basically how I got started in this financial services role and fast forward 15 years.
The Value of a JD MBA in Business
00:04:04
Speaker
I've been doing it ever since and it's been it's been a good ride. That is super interesting that you would be able to sort of like fresh out of law school or a couple years out of law school maybe. ah You're almost thinking like ah like a VC, right? Where's the market going to be in a few years? It's not surprising that you ended up as as a founder with that sort of mindset that's early on.
00:04:26
Speaker
One of the things that's different about you that you mentioned is that you did a JD MBA. Actually, I do want to ask you about the MBA. Do you feel like that sort of idea about where a market's headed, did that come from the MBA? What inspired you to you know add on another year and do the MBA as well?
00:04:41
Speaker
Yeah, so I didn't apply into law school as a JD MBA. I actually started doing that after I started. So what happened was actually during my first year of law school, I came into law school like I went straight out and from from undergrad.
00:04:56
Speaker
hu more or less because I'm like, I think I want to be a lawyer. I don't have any other better ideas. And if I go like in the workforce right now, like I'll never go back. Like I know myself well enough that I'll just like track, right? And I thought that becoming a lawyer was a faster way to like,
00:05:13
Speaker
get into the like executive suite and advance my career rather than maybe go to marketing or something where like you've got like just a lot of people competing. like This is a little more rarefied and lawyers have an advantage. So be a lawyer you know and respectable and there's a low downside on that. So I got there and I'm like, okay, great. And then so like pretty early on, you know, we were in between classes or something like leave a class and there's a bunch of students like parked outside and like the lobby or, and, and they're, they have papers that and they're literally debating a recent like Supreme Court decision.
00:05:50
Speaker
Sure. They're like. That's very DC. They're like muting it out. They're like, oh my god. like That didn't even occur to me. like I have no business. like These people are going to be so much better than me at law because the thought of like using my free time to like read and debate Supreme Court is not something that will ever, I'll never do that. So these guys are going to be great lawyers. I'm going to be a terrible lawyer.
Integrating Legal Training in Business Decisions
00:06:15
Speaker
I need to find something else to do.
00:06:17
Speaker
um And then i did I did a summer associate gig that summer at a big DC law firm. It kind of drove home the fact that I didn't want to be like a big firm lawyer forever.
00:06:31
Speaker
So I was like, okay, well, I don't think that this is my right path. I understand that now, like but I do enjoy business. I do like the skill of being a lawyer. I like the tools it gives you. like I believe the law is a great way to analyze problems generally and risks generally.
00:06:55
Speaker
And so I'm like, okay, well, if I can marry that with some sort of business grounding, then I'll have options about what I can do. So I can go the legal route, but I can also do the business route. And so like, just do the boat, just take bite the bullet, do the year now. Yeah. like Enough to get a scholarship, which helped. And sure. Yeah, ah there was only three of us in the whole school. But I think it was super valuable. And I'm glad I did it.
00:07:19
Speaker
as you yeah As you mentioned, three three folks, it's a little rare. I don't actually don't think I've had necessarily, I'm trying to think if I've had a JD MBA on the podcast. I certainly don't think I've had someone who has done them concurrently, right? Folks who've gone back and gotten MBAs later. Just practically speaking, who do you think a JD MBA is right for? If you were trying to advise maybe like a law school student or someone who's thinking about their career, thinking about going back to school,
00:07:48
Speaker
Who's that sort of program right for? And also, you know, who's it wrong for too? yeah I don't know who it's right for. I know it was right for me, yeah and I think it's right for people who really have maybe that. I came from a liberal liberal arts education and like as my undergrad, and there are people who fit neatly into one box or another, and the people who will debate Supreme Court opinions, and there's people who like love to like analyze a business you know via spreadsheet, right? yeahp there's people There's people who love those two things. And I've always been kind of i've always been kind of like to play multiple positions. here And I really like the intersection of like making business decisions in in even areas of uncertainty.
00:08:39
Speaker
yes like I don't need certainty. A lot of people in the, I've found like a lot of people would like a lot more certainty than maybe I believe truly exists in the world. What I think a legal degree helps you to understand is how to weigh uncertainty and kind of like weigh it out. Law is like, hey, I can spot risk and I can evaluate risk.
00:09:01
Speaker
Right. And the business side is I can actually like price that risk or I can understand what that risk is worth and like, what are the weights on it? What are the probabilities of it like coming to pass? So the that combination is what I found is one of the things that I can.
00:09:17
Speaker
pretty good at which is and I think it comes from the training and the exposure over years you know that was in this in the startup world to actually having to make decision making under decision making under uncertainty at like high velocity and so you get enough reps at that and I think a JD MBA was a great training for that kind of combination of like hey look we live in an uncertain world but we got to make decisions on a daily basis how do we take bets that make sense We're not like risk averse. It's actually about what are the risks we're going to accept and we're going to pursue and do that without with maybe less fear. Okay. I understand it. not Eyes wide open. You know, here we go.
00:09:57
Speaker
I'm going to ask you and in just a second about your GC role at Remitley, but um what you're saying really resonates with me ah personally in that I think I like to often play sort of in the middle, right? like I'm not a banker, but I'm also not a lawyer. and The idea of becoming comfortable with uncertainty really resonates with me as well because you're talking about becoming comfortable with uncertainty in decision making on behalf of your business is really important, right? Being able to weigh different sides of the coin or different risks. Do you think that you can also over the course of your career, teach yourself to be more comfortable with or to become comfortable with some uncertainty in your career? And I'm thinking specifically about your sort of path to becoming a founder, which is
00:10:45
Speaker
perhaps the most uncertain or time horizon you can give yourself. Yeah, 100% because you realize that risks can be mitigated and you learn to actually, like lawyers not to cast ah aspersions, but like they tend to to focus like really on the downside and like the like parade of horribles, worst case outcome type stuff. That's, I mean, that's great. Like you need to, you need to understand that. But the fact of the matter is like,
00:11:16
Speaker
Usually that's not actually how it plays out, right? So like the way I looked at it and founding the company, I was like, look, I've had a great, I've been incredibly blessed. I've had a great run. If this thing fails, which, it which when you start out, like have to accept as a distinct possibility, like what's the worst that could really happen? You know, like my life won't be ruined. yeah Like I'll still be here. I'll have learned like it.
00:11:46
Speaker
I think what it teaches you is that one it's never gonna be as bad as the worst case scenario and there's actually a lot of opportunity and interesting things that come up in just the act of trying and the act of being there and the act is showing up yeah and those are highly undervalued benefits that you can't actually ever realize if you're never willing to take the risk in the first place, right? So the downside is not as bad as it's going to be, and there's a lot more upside in it if you're willing to like, embrace that, oh, maybe it looks a little bit different than I anticipated, but like,
00:12:22
Speaker
it's there and I could give you like a million examples of like the fun of the journey that I never expected in in doing this and people that I've met and experiences that I've had that I never would have had and like even if the startup you know it's going well but even if it went away tomorrow like nobody can take that away from me nobody can take away like the founding experience nobody can take away like the joy of launching a product no one can take away like tech stars program people I've met investors who are great investors like pitches that went horribly like really hard days but it's all part of the experience like I think founding a big reason that I founded or wanted to go out on my own was like the life is short
00:13:10
Speaker
You get one shot and I wanted to see like, what is that? Like, I feel like founding a company is like, for me anyways, like an act of like living living the full experience, right? Yes. and and And putting yourself out there and seeing what comes of it. And so again, to the to the point you've made, it's like you you can't get those experiences without exposing yourself. A risk and downside, but that's okay.
00:13:41
Speaker
Yeah. I think, you know, put into a little bit of like a framework or put slightly in a similar way, investors like to think about asymmetric upside relative to the risk. yeahp And it's easy to think of the sort of founder journey or the startup journey is, well, there could be asymmetric upside relative to the sort of like capital investment required. But what you're saying is there's also a sort of underappreciated or undervalued asymmetric upside to the actual experience of doing this psychic and qualitative side of it. um Yeah. And that's what people talk about when they say like in startups, like the highs are high and the lows are low. It's it's not that you're stop your, you know, like share. face flu you mean like that It's not like you get these like moments of like sheer joy from like, Oh my God, we just solve something really big and meaningful. And that's going to drive this forward and in ways that we understand now and then ways that we don't even understand yet. And then the lows are like, you know, I don't like the lows, but there's something like,
00:14:53
Speaker
very um real about being that close to the like, you know, to understanding the terror and the fear is like part of the experience too. That's why people like Roland. I'm guessing he's an addict.
00:15:09
Speaker
and You had really great success in-house for those folks who, you know, haven't connected with ufology on LinkedIn before. You rose to the GC of Vermitley. You were on the exec team. You managed a pretty large org within the business. It was important not just from a legal perspective, but also really from an operational perspective, given the products that Vermitley was offering. And you stepped aside right before the business went public. I think a lot of GCs out there or just a lot of people generally might say like, that's crazy. Going public is the capstone to a courier. You know, that's the that's what we're all working for. Tell us like what was going through your mind at that point and and why you were saying, you know, this is the right time to found a business. This is the right time to go out on my own. And um I'm not going to follow convention.
00:16:00
Speaker
yeah Well, I mean, I think like the JD MBA analogy is not like too far off here. It was like, look, like I loved, I loved her mittly. I still love her mittly. I'm yeah proud of it. I'm proud of what we did. And it's an amazing company and it will be indefinitely. Like Matt's a great founder. Josh is a great founder. Like the team's amazing and I like love what they did. So yeah, I think people,
00:16:27
Speaker
thought that it was a little crazy to step away. But as much as I like, I loved being GC, right? It was like happy to get that seat. And I loved being a GC of that company in particular. But like, again, I didn't see myself ever as I don't think I'm general counsel, like that's not who I am. Right. And it felt good to have that title, to be honest, like I enjoyed like there was something rewarding about that. But like when it came to the actual brass tacks of running that function over time, um I just I found it like it was it was getting narrower by necessity, right? All of general counsel, and the role of risk and in this sort of like large public organization, like doesn't allow you to
00:17:16
Speaker
be this sort of like lateral player that I've been able to be for many years and then my and might small but mighty team ah was able to be. and Just be like and help be helpful to enabling the business across all these different things. like The business itself had matured. you know There was good season leaders across the organization were brought in that were just like,
00:17:37
Speaker
you know And it's like, hey, you know, legal team, is that a legal question or is that a business question? And you're like, you're right, that's a business call. um That's my opinion. You're allowed, youre you know, you can take the belief in it. And I kind of missed um being able to be a true sort of like business partner. But fundamentally, it was like I saw this problem that existed in the market.
00:17:58
Speaker
for credit products built for those who were generally underserved by the credit systems. It just in the United States. and I'm like, I can't sleep at night because this problem is so big and it's so in front of us and I need to go solve it. and yeah like So it wasn't that I was unhappy there I loved it there it's that I'm like I see this problem it needs to be solved why isn't somebody solving this problem. um That's it I'm going we're gonna we're gonna go to solve this thing so.
00:18:32
Speaker
Can't sleep at night. The VCs love to hear that. I drink a lot of coffee. ah Tell us, yeah, I tried to explain a little bit about what Upwardly does. But to talk to us just for a second about, OK, who are your clients? Who does Upwardly serve? How do you facilitate credit being offered? like what what What happens here operationally? So our mission is to solve the challenge of credit invisibility in the United States and globally. And depending on how you count it, there's at least 50 million people in the United States who don't have credit, don't even have credit score or don't show up in the system, right? Yep. There are lots of companies who would like to serve that kind of demographic.
00:19:19
Speaker
no But they can't because there isn't really like a bridge for a company who wants to serve that demographic to offer credit products. So what upper league does is we make it easy to launch and scale transformative transformational credit products. And what that means is for the business that we're partnered with or B2B, B2B FinTech, what that means is the companies that we partner with, we give them a credit product they can offer into this demographic that will work and it will make and will change the the nature of their business.
00:19:52
Speaker
um So basically like, hey, you can plug this in and it's just going to help you grow, right? Yeah. And for the, on the consumer side, it's like, oh my God, it's a product that works. So it comes from the remittly experience, like international money transfer for mostly an immigrant customer base made beautiful and easy. Like we want to provide that level of beauty and simplicity and do it in a B2B bottle for credit products generally.
00:20:20
Speaker
And that came directly out of the you know seeing the remitly experience of you know so many people who were were coming on our platform. They just wanted to have a great financial experience, right? Yeah. and have a great They wanted to have a great experience sending money home. And we delivered that. And then to look around and be like, well, why doesn't that exist sort of like in the other financial products that are out there? Editory high interest rates just in janky product experiences like yeah, we can solve that like done that before so like but let's let's abstract it a little bit and make it like You know, here's the big play We want about any company to do that
00:21:06
Speaker
And that's what we've been building for two and a half years. So we've got some big clients, we've got a credit builder product, we've got ah credit card products, sortfa sort of white label, secure card product that's launching very soon with some great customers. And I think we're well on our way. Like the way that we see it is by solving the problem at like a B2B level.
00:21:32
Speaker
we can have the scale necessary to really like fill in the gap of those 50 million people. Like, okay, like 18 to 25 year olds who got people are new to the country. We got people who are in gig work. We got people who are um international students. You take all that together and suddenly, Oh my gosh, we feel like actually got like the map covered. Yeah. And, and from that, this rich database of information about like, oh, we can actually now underwrite these people better in a that enables the whole ecosystem to start to lend better and better into this 50 million person niche. And so that's the the big play. And that's how over the long run, I think we'll be able, I really do think we could put a big dent in the predator the problem of credit invisibility, both here with us and then globally.
00:22:27
Speaker
You took the business through Techstars. I'm curious to hear about your experience there. This is maybe more for for other folks out there who are thinking about founding a business or GCs who might be thinking about, okay, my CEO has gone and signed this up for an accelerator a to to raise money and to to get some mentorship. and what What was your experience like there? How do you think about accelerators? Yeah.
00:22:55
Speaker
I'm a big proponent we went through the textures bolder program in 2022 and i think for like a first-time founder in particular like they are well worth it because there's so much that you don't know or so much that you think you know that you actually don't know that you can learn by hard experience over a very long period of time. Or you can have sort of beaten into you over three months and then come up with this. You won't know at all, but like you'll have an idea, you'll get 80-20. And that's enough to make you dangerous. It's enough to make you aware. And you get a whole, I mean, some of our people I consider very close friends now, I met through the program and it helps to just know that you're not alone. and You're going through this stuff.
00:23:44
Speaker
going through the start-up journey, kind of in parallel with these other great people who are on a day-to-day basis, experiencing some of the same challenges that you are. I mean, we met each other through TechGC, and I found that to me to be very similar in that way. It's like somebody's, maybe a couple months, we're all having the same problems, just they're showing up at different times, because we're all on the same stage. So like, I would talk to this person who's having this,
00:24:12
Speaker
issue or sorry, I'd be having this issue and I talked to someone who just solved it three months prior and then someone else would have an issue and I'd be like, oh, I just solved that. Here's how we did it. Right. And so I have that kind of community that really helps to just solve the problems that nobody's written like books about or articles about and then just have a conversation like, how did you solve that? Like that was a weird negotiation. I just went through like, have you had anything similar to that or like, how do you deal with this?
00:24:41
Speaker
maybe, you know, fundraising issue or, um, go to market issue or branding issue or, you know, who did you use for your website design? Hey, that's really cool. Like you use for that don't have they have any free time. Like you can't, you can't put a value on that.
00:24:57
Speaker
It's a community. yeah and yeah You're able to get referrals and that and share ideas. and To your point, it might not be something that a VC fund is deemed worthy of a whole blog post or medium post. or but That's great. and and one one i mean The last point on it is like You know, startups are inherently like you're facing an uphill battle, right? And most fail and most it's very hard to differ. Everyone's starting to fathom. Everyone's got a startup, right? You need things. And I think tech stars
00:25:32
Speaker
and YC have done a good job at this. It's a really kind of a badge of approval. It's like a party mark that says like, hey, we've checked these guys out and they're good. Which goes a long way when you're trying to differentiate early stage and fundraising or customer conversation to be like, I'm backed by tech stars. I'm backed by YC. That gives credibility that you know, you can't you can't like puff yourself up enough for somebody to have get that sort of sit, you know, I mean, evaluation actually, for better or worse is a real thing and just acknowledge that that's out there. And accelerators are an easy way to acquire that.
00:26:17
Speaker
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From creating and managing templates and workflows, to tracking approvals, e-signing, and reporting via an AI-powered repository, Spotdraft helps you in every stage of your contracting. And because it should work where you work, it integrates with all the tools your business already uses. Spotdraft is the key that unlocks the potential of your legal team. Make your contracting easier today at spotdraft.com. You're giving something up, equity, but you're getting something valuable in return if you haven't, say, raised twice before from Sequoia or Andreessen or Madrona or whoever it is. I do want to ask you about fundraising. How has fundraising been? You did a good pitch of upwardly earlier. Yeah, but to talk to us about like successes that you've had with fundraising, mistakes you've made that you think others can learn from.
00:27:35
Speaker
I have many thoughts on fundraising. I hadn't done it prior and it's also one of the things that an accelerator helps teach you is like, how do you effectively pitch? And I didn't have that skill um when i when I started out. So I do think like, again, if you haven't gone through that journey and and done the pitching yourself. like that you know An accelerator is a great way to like get those reps because they'll they'll make you do it. ah I'd say one of the big things that I learned is you have to view it as a process um and you can't do it side of desk. like many founders that and I talked to a bunch. Founders who do fundraising effectively are very disciplined about it.
00:28:25
Speaker
he and That means you can't go like, hey, I'm going to do product and maybe sales like 50% of the time and I'm going to fundraise 50% of the time. like You can't, Ron Swanson from um Parks and Rec at one point, yeah quote, you should never half-ass two things, you should whole-ass one thing. If you're fundraising, you're fundraising. That's what you do.
00:28:51
Speaker
And people say like you gotta walk and chew gum at the same time, ah you gotta be able to do multiple things. and I'm like, I actually don't believe that. What you need to do is fundraise, because that and improves your probabilities of success. Because if I'm talking to 10 VCs,
00:29:08
Speaker
Like your chances of hearing no for any number of reasons, just not the right time. Maybe they don't have the capital. Maybe they're doing other deals. Like it's like exceedingly low. You've talked to a hundred. Your odds go up, right? But the only way to talk to a hundred VCs in a week or in two weeks is to knuckle up, have your list and treat it like enterprise sales.
00:29:30
Speaker
i didn't I didn't appreciate, I didn't know what that was a couple years ago. What you need to do is like, okay, I'm going to dedicate myself for a significant period of time to just having as many conversations as possible, advancing people through the pipeline, actually trying to get them to say no, because they'll drag them, get them to go faster, push them to no. And if they keep saying yes,
00:29:52
Speaker
Great. Advance them. But like I don't want to spend a lot of time talking with folks who are like, hey, this is great. let's ah you know Put me on your distro. We'll talk in a few months. When you're raising, that's like poison. Because I need to use those but those half hour blocks. to talk to people who actually, you know, might want to write a check and not like aren't just like, kind of like, you know, hanging around the hoop and waiting for waiting to pounce when the like, you know, an easy rebound comes up, right? And we've proven out that instead of put all the risks at all for them, you know, there are people who are willing to to take risks.
00:30:28
Speaker
I love those people and what I love about the fundraising process is a process and it is a slog but it is worth it to find the handful of people who like truly believe in your company and like at their core and believe it needs to exist and are willing to evangelize for it.
00:30:48
Speaker
Most folks who are like, oh, this is an interesting space and I've got like, I have a passing curiosity or if I've got a thesis around it and and aren't really like bought into you as a founder, what specifically you're trying to do. So like, it just makes me, I love the people who invested in us.
00:31:05
Speaker
ah Yeah, and it is almost like a weird, you know, not to be romantic about it. But it's kind of like a love at first sight thing. It's like, you know, you're you're having this in a fundraising process, you're having like 100 meetings, right? Mm hmm. 200 meetings.
00:31:20
Speaker
And most of them, some of them go like really, it's like dating, it's like spending. It's something really poorly. And you're just like, Oh, God, I hate this. This is so i do I really have to keep doing this. Like, do I want to get on this the next call and like, get myself okay, mentally ready. And then you get on the call. And then it's one of these people that get it.
00:31:42
Speaker
and get you, and it's just like, like it's five minutes. like The decision's already, you can tell that this is gonna work, and that is so makes it worth it. And those people, we have this great investor called Dundee, Dundee Perpetual Capital, shout out to Catherine Williams, she's on her board. like I knew the minute that we met, like this this is probably gonna work.
00:32:08
Speaker
And there are others on our cap table, J4 cascade seed fund, like that I call a Vesta fund. There's so many Senator, uh, who you just, I can call up and I can tell them, I can have a business shot. I have a transparent conversation with them about what's going well, what's going poorly. And they're not like holding, they feel more invested than just the dollars.
00:32:35
Speaker
yeah um and so i don't know i it's worth like Do a process right, do it hard. It's worth it. you will Again, you'll find people you didn't expect. The the way you can and end up in trouble is like if you're not having enough meeting, you're not going to meet those people. You're just not. and You may end up with some investors perhaps that you're less enthused about because you didn't take the time to see what's out there.
00:33:02
Speaker
So I'd just say you got to be all in and people, the world will pressure you to not be all in, but I think you have to have the discipline to be like, this is what I'm all about for either this quarter or two quarters. So that's what it's going to take.
00:33:15
Speaker
I was going to ask you what you learned about pitching and and pitching effectively, but maybe a secondary question in there is, is is pitching important? Because you're talking about sort of having a simpatico with the investors who really get it. Just don't need to sell them on the vision. Talk to us about what what pitching has been like for you.
00:33:39
Speaker
ah It's been a journey. Again, I didn't know how to do it when I started out. Like my first fundraising pitch was a, in retrospect, huge, embarrassing failure that I didn't recognize at the time. Like VCs expect to be pitches, be pitched.
00:33:57
Speaker
VC and they expect to be pitched in a certain format because what they're trying to do is extract the core nuggets of information about your business to understand whether it's something that they're interested in and whether you can effectively communicate it in a way that says, hey, I can lead this organization to realize this vision, right? And you have to do it verbally on cue. You got to like be able to do that. so And my first fundraising pitch, I did what I would do ever mentally, which is like, hey, for a big investment decision, to be like, hey,
00:34:26
Speaker
Here's this great opportunity or this thing, this problem we need to solve. Here's how I can solve it. Here's a written memo, six pages with the supporting graphs and charts and yeah explanation, whatever, and be, here's how we can do it. And like, it'll cost, you know, X.
00:34:44
Speaker
and so Amazon style. Amazon style. It was very much Amazon style. What I did is when I just started out, I'm like, here's the company. Here's the idea behind the company. Here's a six-page memo and distributed to like the VCs. and I hit the first meeting and I show up to the first meeting.
00:35:00
Speaker
and like say so Everyone's read the memo. I'm like, prepared to make questions.
00:35:08
Speaker
And and it was on it it was on a Zoom because it was like mid-pandemic. And like it was just like, go radio silence for like 15 seconds. I'm like, is this camera on?
00:35:24
Speaker
um that's not how That's not how you do it. It's like, you have to, VC is a sales pitch. But you're not selling your product, you're selling your company, you're selling the vision and that you know the rules of the game and I can play this at a very high level. And so what they're looking for is you need to be able to communicate the story to explain the vision and to do that like succinctly, which I'm failing to do here. ah yeah um
00:35:55
Speaker
And in and ah it' like entertaining and like show your personality a little bit. And if you can do that, like, okay, great. Like you pass that test. Um, but that's like one of many skills. Like you end up learning by trial by fire in just doing this, doing this. So like, and the only way to get good at it is just to do it a whole lot.
00:36:16
Speaker
e We've talked about getting over the sort of hump and founding the business, fundraising, going through an accelerator. you know Another aspect here is you've managed big teams before, but now you're the CEO and ultimately all the employees are going to be looking to you.
00:36:36
Speaker
Learning to lead as a CEO, I'm sure, isn't easy. What are the aspects of the role that you feel like have required the most sort of personal growth for you? How do you feel like you've grown over the past two and a half years?
00:36:52
Speaker
I mean, I've definitely evolved in that you might while I had like a multifunctional organization before, it was always kind of like with through a risk lens. And then there's a very legalistic lens and now it's like over everything.
00:37:09
Speaker
so like How do you think about like how an engineering organization should perform? like How do you think about ah how a sales organization perform? and like Especially when you're not a subject matter matter expert. like When I ran legal, like I'm lawyer. like I can understand how to this should look, feel.
00:37:26
Speaker
yeah and compliance is also a risk function. so like I can understand we're trying to control for risks. We have a different outlook on it, but now it's it's much broader. so that has That has been a learning. I think external communications has been a growth area. I think we just went over that. um and Then you know managing, like being able to set the vision for like the entire organization and then really be the one who helps to drive priorities. Whereas before I could make advice and I'd be like, ah, we should have done, okay, that's the decision that that's made. But like, yeah, I would have done it slightly different. Like, it's hard being in the seat.
00:38:09
Speaker
and setting those priorities when there's so much you can do and there's so much you want to do, but you got to be like ruthless in terms of your prioritization. and I think you know lawyers as advisors generally, executing it is ah is a different thing. so I've had a new appreciation for like how do you make these hard trade-offs that you would have recommended, maybe you would have recommended it, but then you actually got to go and execute it.
00:38:32
Speaker
and not get into this like paralysis by analysis mode, which um I think you can know ah perhaps the downside of being a lawyer is maybe you can overthink things sometimes.
00:38:43
Speaker
Sure. Let's talk a little more about that. I would imagine there's been a pretty big mindset shift from being a lawyer to being a CEO in terms of your priorities, how you you view yourself from an accountability perspective to the business like you're alluding to, right? You're not just sort of advising the decision. Ultimately, every decision that made was made by the business It might not be exactly what you would do, I suppose, is the org gets bigger and bigger, but it is a culture that you've created and a business that you've created and a vision that you've set to talk to us about that that mindset shift from being, I'm a lawyer to I now run in the business. Yeah, it's funny. like
00:39:23
Speaker
it is um but ah Because before, as a lawyer, as an advisor, ah you're an input to a decision, and you're an input to a business decision, and that's how it should work, except in like very specific contexts.
00:39:38
Speaker
right you're really you're You're an advisor to a principal, and the principal is the one who makes the decision. And one of the things I didn't appreciate is when I took on, when I did the founder role, making these decisions, like I kind of took some of that, um like I'm an advisor and here's how I would before process and present information. And when I started doing this, I would actually just, I'd make the same decision as if I were in that old role. So I basically like would take all that,
00:40:10
Speaker
analysis and risk adjustment that would be communicated like as the decision. where Whereas what I realized is actually you need to take that in input it and filter it through all like the business needs of the organization and then weigh that out and perhaps even be willing to ignore some of that advice to make right a recent decision. A good example of this is like in our first fundraising round or pre-seed deal led by Dundee,
00:40:36
Speaker
you know They give us a term sheet. We're like, great. This is great. And I turn it over to our lawyers. And they come back. And you know they market up like crazy, because that's what lawyers do. And my old road role as GC, I would take that and I would be like, well, what actually matters here? And like what are the business ones that I think we should negotiate on? And then I'd make that recommendation to Matt. yeah runs And he would say, no, we're really only going to like negotiate on this one thing. right Or we're not like that's not important. like How important is that really? right Okay, now fast forward and I'm in the seat and I got this big markup and me just being the lawyer be like, okay, well we can trim this down a little bit. And we'll end up like turning back to our our VC partner, like, oh, totally marked up red line. And then she immediately calls me up. She goes, let's go, Aaron, there are 140 track changes.
00:41:31
Speaker
and She said that I'm like, oh shit, I didn't filter it sorry. Yeah, I didn't put a business filter on my stupid legal brain. either be Matt and Aaron. Can't this be Aaron? Now I have to be i have to be i have to do this role. um So I learned a lot that way. And i've ever since then, I've processed you know but that sort of like legal instinctuous muscle that I built up over years ah needs to be countered. And and so that that that' that's been some of the journey.
00:42:07
Speaker
We've talked about the highs and the lows of this sort of founder journey. you were we're We're talking about Wisconsin in just a second. You were living in Seattle. You're in Seattle right now. You can telephone or teleport or into Seattle a lot. and and I was listening to an interview with Jeff Bezos the other day where he talks about um how he doesn't think CEOs should be stressed because they can delegate their stress away. And I sort of get that, but I also think you're the founder, you own the business. You know like you you you have ownership over the business is really what I'm saying. And it's also early like for for you. um maybe that is Maybe that's true if you have 10,000 people working for you. But um with a smaller team, right like problems are going to bubble up. And so my my question to you is, like how do you personally manage
00:42:57
Speaker
that stress, being a founder and being in the seat and feeling like you're responsible, feeling like you're accountable. Some days better than others. Yeah. Um, I think I, the main thing is in our co-founders and the team share this as well as like, we care really deeply about solving the problem and that keeps you going even when you're stressed or things are hard. Like if we didn't really care about solving the problem, I think it'd be the stress probably could be overwhelming. Sure. But it's like, Hey, we're making progress and we know what we need to do. And so like the stress actually helps you focus on the things that matter.
00:43:36
Speaker
Rather than chase, you know, cause the stress is being created because it's like we need to deliver a very specific thing. And that is known. And it's just like, it's hard to do all of that in a short amount of time with limited resources. I think the stress actually helps you focus as long as you don't let it like have negative externalities or, and stress is contagious too. So you have to kind of like manage that person. That's been part of the journey too, is learning to manage. Yeah. patients do the whole thing. And then you know find things that like are stress relief in a healthy way. Routine, for me, it's routine. like Just being able to, like i I have routines and exercise and things to look forward to that are outside of work. Because if if left to my own devices, like my mind would just be crunching on the same problems over and over and over. And you need to like tune it out. And so like keeping some semblance of balance
00:44:30
Speaker
So my kids, family, exercise, wife, like these are important parts of my life. i don't like i have be I have to be more than just the founder of this company. Right. Yeah.
00:44:43
Speaker
A final sort of question for you on the the upwardly journey before I've got a few fun questions to close us out. An interesting aspect of this is you're building upwardly in Wisconsin. You move there, you're deeply connected still to the Seattle tech ecosystem. But you know how do you think about building a company in a slightly different market than San Francisco, Seattle, New York City,
00:45:09
Speaker
finding talent in maybe unexpected or slightly underappreciated places. Talk to us about that. I mean i firmly believe that great companies can come from anywhere. and That's mostly because great people can come from anywhere. and you have These are these great things now called planes and Zoom.
00:45:32
Speaker
that mean that i so The joke that then you just made was like like, I work out of Milwaukee. but my team is heavily in Seattle. so like Sometimes I say I live in Milwaukee, but I work in Seattle. We can be everywhere. and Because talent is everywhere, it allows us to access, especially as a startup, the right people for the role at the right time. That would probably be harder to do if we were just in the Bay Area or just in
00:46:03
Speaker
Seattle. I do think it has like, you're swimming up like, let's, I'll be completely honest, you're swimming upstream. Like these ecosystems don't exist in the same way in my neck of the woods. But you know, when you're a startup, you need every advantage that you can to help you both from like capital and invest ah capital and partners and just the ecosystem around and I get why there is a systemic advantage to being San Francisco, Seattle, New York, but great founders and great companies can come from anywhere. and If you're truly committed to building a great company and you're willing to say, like I understand that trade-off, but I'm going to make it work anyways, it's very founder-like. There's some great founders that I've met around Wisconsin, which is probably going to shock some people, like up in Green Bay and around Milwaukee and Chicago. like
00:46:56
Speaker
great, like truly great founders who are just like, I'm going to make it happen. And I don't care that I've got this, I've got all these other systemic disadvantages. i don't care do it here and watch me, right? And then, you know, check in in 10 years and let's see how we're doing. I don't know. I think it's awesome. And there's a bunch of VCs now, I think, who recognize for a variety of reasons. They've got LPs who want them to invest in companies that are not just coming out of a few hubs or not just on the coast. They're, they're you know,
00:47:26
Speaker
trying to help and also sort of chasing returns in in places like Milwaukee. yeahp and I think people want the opportunity. The University of Wisconsin, there are many great academic institutions that are churning out incredibly talented people, both who like graduated. like Again, smart people can come from anywhere, great talented people can come from anywhere. and But people do want to live in Wisconsin. Like, yeah, maybe I didn't grow up there. My wife did, she brought me there. But they want to go back and they want to live a life that has some balance and reflects maybe their values differently than than other folks. And they're just looking for opportunities. So like, you know, can my company can others be a reason that people come back? Yeah.
00:48:17
Speaker
I think so because there's no monopoly on why. like There are, again, network effects as to why see why San Francisco tracks. and yeah But I think there are people who are like yeah who are outliers like me or whatever who just, that's not how they want to do things and that's okay. and You know what? Come to Wisconsin, come come work with upwardly. like yeah gonna We're going to do something great in Milwaukee and surprise some folks.
00:48:46
Speaker
It's awesome. A few fun questions for you now. So we start to wrap up. Your favorite part of your routine or your day to day? Talking with our customers. Yeah. Yeah. Like 100%. So like the businesses that we support, like the models and their unique angle on on a particular industry or industry segment.
00:49:13
Speaker
Those are you learn so i just again i like i like to learn so i need to learn so much about an industry and companies and like how these these different sectors of the economy work that you have no exposure to otherwise and i get to like see how this really cool stuff so.
00:49:30
Speaker
like We've got a company in the ah that we're partnered with called the Tip House. They're Seattle-based. I just met them yesterday. and What they do is tip distribution like tip calculation and distribution for ah hospitality industry. Now that everything's got digital, rather than give people cash like across the counter at the end of the night to pay them for their tips, what we do is we they do the calculation and they push it on a card that we host. But I've got to learn about, like I was a waiter at one point and I got paid in cash and now I get to see, oh here's how the digital economy has changed how restaurants work. That is so cool. like and i and We've got 17 companies like this, so every day I'm learning something new and I'm excited about the models that we're helping to enable that weren't possible before. so That's fine. Do you have a professional pet peeve?
00:50:22
Speaker
um I don't like it, and I'm guilty of this too. I don't like it when people are late. I was a college football player and my coach used to say, on time you're late. So I don't like lateness generally. And then like don't ghost me, like don't ever go radio silent on me. like As a lawyer, back in the firm days, like you you just learn to be like highly responsive to clients, right? Even if it's just saying, like hey, got your message. like i can't I'll get back to you in half an hour or an hour by end of day. like right When I get radio silence, it drives me up the wall. Sure.
00:50:58
Speaker
I will say you're an understanding guy. I lost power right as we were about to start to record this podcast. And Aaron was nice enough to say, we'll figure it out or we'll reschedule if we have to. You told me so, but you called me and you said this is the issue and that's totally acceptable. But if we had gone like 15 minutes, I'd be like, geez, where the hell is Tyler?
00:51:26
Speaker
and mickey interviewee Yeah, I'm a big reader and I like to ask our guests if they have a book recommendation for our audience. um Could be professional, could just be something interesting you've read recently. There is a lot. The best book on general management I've ever read is high ah output management.
00:51:46
Speaker
yeah by the former CEO of Intel. And i I still pull that off the shelf and read it. And I just think it's good, like business firsthand experience. I recommend it to anyone. And then for those who are interested in startups, the right it, which is about like, how do you figure out, you come into the world with like a problem statement about like, I think the world, like this is a problem. And you said, I saw it from like the founding story, like here's the problem statement, but the solution is actually probably something that is not in your head because you don't have a idea what the solution should be and then you go and take it into the world and they're like, actually, that doesn't resonate with me at all. And you don't want to build products like that, right? Right. It is about how you get to a solution that people actually want, a solution to a problem that people actually want and will pay for quickly with limited resources. And so I recommend that to anyone who's in the startup world because I think that's the mentality you have to have to get
00:52:44
Speaker
to To figure out that zero to one journey um is all about pre to pre to typing and prototyping your way into product market fit before you go and build the month the big monster optimized machine you know.
00:52:58
Speaker
I love it. a Two new books for the audience. As we as we wrap up, ah last question for you, sort of my traditional closing question. And that's if you could look back on your days as a young lawyer, maybe just graduating with the JD MBA from GW, something that you know now that you wish that you'd known back then. It's going to be OK.
00:53:27
Speaker
Like, you can jump. You don't have to have certainty. No one knows the future. Take smart risks and work your ass off, and it's going to work out. I think that version of me would have been scared by some of the risks.
00:53:54
Speaker
I took sure not knowing the outcome. It was scared looking at some of those things, but I do think that um it You don't realize that you can land like you can land on your feet, right? These decisions, you can make them and you can pivot and you can change. And we're all making decisions every day. um Amazon has this like one way door, two way door construct, right? Most decisions are two way doors and it can be pretty quickly changed. We're human, we're fluid, we can change the risks that you take as long as you know the true downside.
00:54:33
Speaker
Like you can, you can take them and you'll be all right. Thank you. This has been a really great conversation, Aaron. Uh, super candid, good for lawyers, legal professionals, GCs, founders. Uh, pretty much everyone should listen to this in business. Uh,
00:54:57
Speaker
I really appreciate it. Um, thanks so much for joining us. Thanks, Tyler. It was great seeing you. And to all of our listeners, thanks for tuning in to this episode of The Abstract. And we hope to see you next time.