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Entrepreneurship Lessons from Losing a Lead Investor Overnight with Andy Ellwood

51m 22s

Entrepreneurship Lessons from Losing a Lead Investor Overnight with Andy Ellwood

In this podcast episode, Andy Elwood recounts the devastating loss of his largest investor in a plane crash, which led to the collapse of his startup’s funding and eventual failure. The investor, a Silicon Valley legend, had promised a $5 million bridge loan, but after his death, other investors withdrew, leaving the company unable to make payroll. Andy shares three key lessons: always expand your network beyond current supporters, have contingency plans for every critical role, and stay in love with the problem you’re solving, not the company itself. He also recommends a team exercise where employees write the company’s obituary to anticipate failure, noting that “failure comes from the failure to imagine failure.” Despite the tragic setback, Andy’s resolve was driven by a deep commitment to helping families afford groceries, a problem that persisted even after the company shut down. He reflects on his early entrepreneurial journey, starting with a lawn-mowing business at age 12, and how that shaped his resilience. The story underscores the importance of preparation, adaptability, and passion for purpose over profit.

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I know you guys need a bridge. I'm going to wire you guys $5 million on Thursday. From something birthday party in San Francisco, and then was flying himself and his best friend up to his vineyard in Northern California for dinner with the family and crashed the plane and died. In that one moment, almost everything changed. And a lot of the existing messages that we had, it would be because of this lead investor. He had brought a lot of those relationships. And so when he was out, they were all kind of like without a leader. They've just been kind of going along with him. And so it was hard for all of us and on a personal level. I can't even imagine. Everybody's so optimistic. They never ask what's the worst thing that can happen. And so if you were to give advice from what I'm hearing, it's have a backup, whether it's investor, even for your employees, your key A players, and then a backup, and then another backup upon a backup. Would you agree with that? Failure comes from the failure to imagine failure. Just last week, I sat my team down and I put up a tombstone on the TV. I put the name of our company. I put, you know, 2025 dashed and then I left the second year like, and I made our team write the obituary for our company. And everybody had to go around and read how long into the company lasts. And then the explanation of why we died. Those are legacy. Who misses us? And how could we have survived longer? I love the tombstone analogy or exercise because a lot of people are just like, well, let's do a swat analysis, right? It's so corporate. Let's get down into the weeds. Let's cycle back on that, like all those different names. But yeah, the other thing is when you're talking even about yourself, right, they say for, you know, trying to find your why. I recommend for those listeners who've never done this seriously, right, your obituary. It is one of the most profound things and emotional things you can never do. But to translate that to a company, I think is very profound too, especially when you've kind of built for an exit. You know, I love teaching and I feel like we're doing a master class here. We've got a guy here, Andy, who has been on three rocket ships. He's got a ton of experience. And the best experience, of course, is founding and then having to shut down a company. When that changes, you're going to pivot. Have there been any pivot so far in the journey? Yeah, the speed with which the technology world has changed. We're a 10 month old company from founding the company in April of last year to now march this year, right? Just stepping into-- I'm Garrett Wong and this is the Investing to Win podcast. How do you define success and what does winning look like for you? Andy, you lost your biggest investor in a plane crash. What happened and how did you keep going? It was one of the craziest days of my career. And it was Monday and our chairman of our board and our largest investor had thrown himself a birthday party in San Francisco. It was a 68 years old, burguerrious investor legend in Silicon Valley, been the investor since the '70s. And it was on his last fund and was all in on my company. And it said, you know, I know you guys need a bridge. But have my birthday party Monday recover. And then we'll get to work. And this was the first Monday of 2019. And through the Silicon birthday party in San Francisco, and then was flying himself and his best friend up to his vineyard in Northern California for dinner with the family and crashed the plane and died. And we not only lost kind of our third co-founder, right? Because he was there. He was the first money in. He was really supportive. But we also-- we needed that bridge that he was going to send to us. And we had been hiring. We'd been building our monthly burn with that expectation. And we had not been talking to other investors. And that was in hindsight, we really did have all our eggs in one basket with our existing investor base. They were super supportive. And they said, we're going to back you. But then in that one moment, all of a sudden, everything changed. And a lot of the existing investors that we had were because of this lead investor. And so when he was out, they were all kind of without a leader. They'd just been kind of going along with him. And so it was hard for all of us on a personal level. But then especially from a business level, we had to make payroll. And we ended up not making payroll. And a few months after that, because we were missing that investment. And so 2019 was a very pivotal year for us. I put way too much of my own money in. I co-founded way too much of his own money in just trying keep it all together. We did survive. But we took pretty harsh terms from some other investors who swooped in, but swooped in with a premium on what they expected from us. And we said, well, at least we survived 2019. 2020 is going to be our year. And this whole pandemic thing happened, unfortunately, that just compounded the challenges. Boy, what a story. Know what I was doing my research on you. And I saw that. I mean, I've had my own pivots. I think everybody has those defining moments a lot. A lot of that is what I like to explore on investing to win. And so obviously, it's awful for just losing probably a friend and a mentor. Obviously, an investor like that doesn't come in just from that. And then you have to have the uncomfortable conversations very shortly after what the heck are we going to do? So what were the-- if you were to say the top three lessons from that experience in terms of hindsight, right? What would you say those would be? Always be talking to people outside of your network. Never stop growing your network. No matter how confident you feel around your network, no matter how confident you feel about the people that are in your camp, there are certain roles that you do need to know what you would do if that person was no longer a part of the team. For whatever reason, you lost your CTO, right? If you lost to your real investor, right? And we just frankly just caught flat-footed because we've been just relying on our board, right? Our board said we got you. But then 40% of our cap table died in the play crash. She was a single GP at that point. He bought out his partners, all the money reverted to the LPs as soon as he passed away. There was no contingency plan to continue what his intentions were within the fund. So I think that was one number one. Number two, when everybody doubts you, you still have to believe in yourself. We had to have very hard conversations very quickly with a lot of our really, really talented team members. But we were raised our series day. We were on our way to our series B. We were going after pretty, pretty meme talent. And we've been able to steal a lot of really incredible team members. But we also found out that some of those team members were there for the paycheck. And when things got tough, they said, hey, no problem. Good luck on out, right? Some people didn't even say good luck. Some people just said, I'm out. If you miss this payroll, I'm not from the back of work. And as a young company, we were playing a bigger game. And so I look at it fully, I appreciate it. And that everybody is built to take the risks that founders do. And that everybody's built to take risks of early, early stage companies. But the speed with which some employees left was a little bit jarring. But they did what they needed to do for them. But it's going to happen. And there's not that much margin for error once you get to a company in the size that we were. And then I think the resolve to keep fighting comes from being in love with the problem that you're trying to solve, not the solution that you've created or the company that you've built. And I think that that was the thing that probably kept me in. And some might argue longer than I should have stayed, even through 2020 and the pandemic. Like, we were still fighting. We were still trying. We probably over committed in some ways, maybe more than we should have. But the problem wasn't done. And there were families that we were serving. There were users that we had. There were clients that were still loving our product. Even if we didn't have the same investor group to support us, and we had to go find new investors. And those new investors weren't quite as big and big of believers as the original. We still thought that there was a problem to be solved. And so I think that that was the underlying piece of the puzzle that for me, if it had been trying to make it easier to post on social media, I probably would have quit. I probably would have quit sooner. But because we were actually dealing with helping families be able to afford groceries, real problems with real families that were able to know our users. And they were families just like the one that I grew up in. So I knew how important it was for those reasons. I think that that's probably what kept me in, as long as I stayed, even though eventually the company went out of business, probably the resolve to keep working as hard as I did, even when a tragic thing had happened, was really around that idea. Wow. I'm going to have you repeat that last one, because I've never had a guest who-- I've never actually heard that phrase. So you want to be in love with the problem, not the company itself, or can you say it again? Yeah. You want to be in love with solving the problem, not with the solution that you've created. And the way that I think about this is there was a talk that was given by the CTO of malaria and no more, a nonprofit that helped to get mosquito nets to people in Africa. And he said, and I always remember it, it's really stuck with me, that if you're the leader of a nonprofit and you don't know how to put yourself out of business, then you're in love with your organization, not with the solution that you're trying to create. Nobody wants there to be cancer nonprofits because nobody wants cancer to exist. Nobody wants there to be hunger nonprofits. Like, if food banks went away, that would be amazing because it would mean that there wasn't food insecurity. Those are things that should be built to disappear at some point. And I think the same thing with, you know, a startup, like your role is to build something that creates a way for a problem to go away. And you bother to leave as much as you need to to roll with the new things that happen, roll with the new technologies that exist, roll with the new opportunities to eradicate the problem that you're trying to solve and to be the solution. And you will quit if you're just in love with a piece of technology that you created that does a thing. But if that problem, if you still know somebody who has the problem that you're trying to create a solution for, if that problem still exists for somebody, you're not done. And I think that's a perspective that's been helpful for me. Yeah, it's interesting. I look at different industries in healthcare and wellness. Let's just take a physiotherapist, not as an example. It's fascinating because, you know, you could have either a large clinic with a bunch of operators or just whether you're a single operator, it doesn't matter. The point is, when you fix your client, they don't need you anymore. And so you constantly have to farm. And like it's not like you can have, well, I guess you could maybe invent some kind of reoccurring, you know, physiotherapy program, but just take anything where you're healing somebody and truly helping them. And they never need your service again. That's right. But what you're talking about, I think there is passion. Just back up for just a slight second there because, you know, what we're talking about, succession planning. And I think a lot of people in business, really, whether it's partnerships or groups like yourself, like there are in love with the, you know, solving the problem, that's for sure. But everybody's so optimistic. They never ask, what's the worst thing that can happen? And so if you were to give advice from what I'm hearing, it's have a backup, whether for its investor, even for your employees, your key A players and then a backup and then another backup upon a backup. Yeah. One of my favorite investors, Josh Wolf from Lux Capital has the same, has the saying that I think about a lot, which is failure comes from the failure to imagine failure. Okay. Wow. This is going to be tons of zinger as you're giving me her Andy. That's, I love it. Failure to imagine failure. And just last week, I sat my team down and I put up a tombstone on the TV and I put the name of our company and I put, you know, 2025 dash and then I left the second, the second year blank. And I made our team write the obituary for our company and everybody had to go around and read, "Here lies stretch," which was around from 2025 to, and then they filled them with blank, how long did the company last? And then the explanation of why we died, what was our legacy, who misses us and how could we have survived longer? And I got to tell you, like what scene, you know, seeing my company name on a tombstone was pretty jarring for me even though I was the one who did it. But when I was an executive coach, I used to do that in the office that I would lead for other companies. And it's incredible to see all the different ways that your team can imagine failure. And sometimes it's, you know, just wide open, you know, things you maybe have never thought of, but from their point of view, right? There you go to market team member, junior team member, and there's seen something that you're not. And they're like, that's a point of failure that could kill this company, right? And all of a sudden it comes, it surfaces. And so I think that that's something that, you know, I get paid to have that point of view, you know, by being the founder and CEO. But like, you know, I want those pieces of input because people see things differently than what I see from their vantage point with them in the company. Yeah, I love the tombstone analogy or exercise because a lot of people are just like, well, let's do a SWOT analysis, right? It's so corporate. And then we get down into the weeds. Let's, you know, cycle back on that, like all those different memes. But yeah, I mean, the other thing is when you're talking even about yourself, right? They say for, you know, trying to find your why. And I recommend for those listeners who've never done this seriously, right, your obituary. It is one of the most profound things and emotional things you can ever do. Go take a pen and a paper and notebook, go into a dark room, play some light music and just write your obituary of what you wanted, everybody to say it, your funeral, what you wanted to mean to everybody. But to translate that to a company, I think, is very, you know, profound too, especially when you're trying to build for an exit. All right. So you mentioned there was a company failure here. Let's go all the way back. Can you give us a bit about your background and how you started even go back early if you want to? Yeah. Yeah. So I have been told that I have big brother energy. But like, I try to make sure that it's like the big brother that you would want to have energy. Not the bully big brother. Yeah. Not the bully. You know, like, I'll help you get things off the top shelf. I'll give you a boost over the fence. And I think that that really shaped a lot of, you know, how I moved through the world. It was doing, you know, I love my siblings. You know, I'm really grateful that I was the oldest of the four of us. But my parents were, you know, incredibly social people. Our house was the Super Bowl house. Our house was the hangout house. Like, we were always had, you know, if it was like, hey, we should all get together. Yeah, we're going to go to the Olden's house, right? My mom, you know, was best cook ever and, you know, always had, you know, she's famous for her chocolate chip cookies. And, you know, and very social. And my parents, you know, led small groups that are church and so like we were always, you know, in the mix planning things, organizing things, convening groups of people together. And that really shaped a lot of, you know, how I think I moved through the world today. But we're also like, I didn't know how much month we were burning up like my parents never, you know, never, I never worried that we weren't going to be able to, you know, pay rent or, you know, have food next month. But in hindsight, like, you know, there are times where like I know that my parents were struggling more than they let on. And so, yeah, I think that some of that is really what triggered maybe the entrepreneurial bug in me. Yeah. Neither of my parents, you know, are entrepreneurial, you know, and they sometimes have looked at me and been like, where'd you come from? But, you know, my $1 a month allowance when I was, you know, 12 was just not cut that for me. And so I was like, I can't have to make money. So at 12, I started my first company, a law annoying business. And in Texas, right, the grass starts growing, you know, in February and keeps growing until like November. So you know, you got 10 months, you know, of, you know, making, making hay, you know, all the sun shines. And I was homeschooled. And so my mom let me create my own schedule as early as age 14. And so I would mow lawns in the morning, come home, shower, have lunch, and then I would start school. And so I had an advantage over all the other kids that were in the more traditional school system. So three of the week, you know, I was out, you know, running my lawnmowering business. And I almost didn't go to college because I was making what most people make their first year out of college while I was still in high school with my lawnmowering business. In the late 90s, I was making like $30,000 a year in high school. And I figured out how much fun it is to, you know, to build teams and to, you know, give them to sales. And, you know, I just went door to door and would, you know, would knock on doors and be like, hi, my name's Andy Elwood. I'm with reliable lawn care. I'm going to be mowing your yard this summer. If you leave $20 bill underneath your door mat every Wednesday, I'll be, you know, your yard will be mowed before you get home. And people are like, you're going to mow my lawn. I was like, well, it's hot. You don't want to do it. They're like, you're right. And so I just, you know, check underneath the mat for the $20 bill there. We'd mow the lawn and-- For some of sales, I love it. Just have a canvas of neighborhood like I had an old MAPS go, you know, and I just put x-ray across like it was a funnel management like I didn't know that that's what it was. But like I learned a lot of that early on. But it also, you know, it was great for me, you know, talking to adults, you know, as a kid and just, you know, kind of like, you know, a bother truck, you know, when I turned 16 with all the cash that I'd saved up. And that allowed me to expand beyond the neighborhood and started to hire my younger brother and his friends to work for me. So went to college, studied, you know, studied finance, but continued to be pretty good sales and sold life insurance as my first job out of college, which, you know, if you haven't, if you haven't, you know, spoken to a life insurance person, you know, recently like it's, that's, you know, if you could sell life insurance, you can sell pretty much anything else. Oh, Dornard or Vacuum Sales, right? is probably the second hardest thing that I'm thinking in my mind. On the first side, but I was fortunate to get recruited from, you know, being in financial sales to think of sell private jets for Warren Buffett. That was my second job. I was, yeah, I read about that. Yeah. How do you, how does one goalboat and start selling private jets for Warren Buffett? Tell us. Yeah. Yeah. So, so Warren Buffett was the client of net jets in 95. Oh, I'm sorry. The company started in 87. Warren Buffett became a client in 95, bought the whole company in 96. So it became a bookshare half the way company in 96. And one of the divisions of the company was called Marquis Jet, and it was jet card, which you bought 25 hours of flight time out of time. It was kind of like a debit card. And so, you know, from wheels up to wheels down, we would debit, you know, two hours, two and a half hours off of your card. And then whatever was down to re up, we just wouldn't, you know, we'd sell you another 25 hours. And an amazing way to spend my mid 20s. You know, clothes on celebrity athletes and billionaires. And they actually took my phone call. You know, they, they were like, oh my gosh, this is the guy who has access to Warren Buffett's private jet fleet. I would like to fly on those planes. And so I learned a ton, you know, it was fun. You know, like I was in Dallas at this point, you know, the Dallas Cowboys and the Texas Rangers, you know, they were all my clients. And, but and there were some, some celebrities who, you know, live and lived in the Dallas area for tax purposes, you know. But it was actually the clients that no one had ever heard of that were the ones that I think I've learned the most from. You know, there were titans of their industry, but they, you know, they were in a very small specific industry. Right. They were not famous, you know, they were not in the forms magazine. But if you knew, if you were in their industry, you'd heard of them because they were the best of what they did. And they were the ones who actually convinced me to quit being the sales guy. And they said, look, Andy, like, you know, I'm excited that you have, you know, these amazing stories of celebrities and athletes, but like my limo driver has better stories, like quit limo driving your way through life. If you want to get in the back of the plane, go take some risks, right? You'll never get there by being my sales guy. And, and I remember that conversation very clearly, um, with one of my bigger clients. And so I quit and joined a startup a year later, moved to New York City and joined my first technology company. And, and that was a pretty pivotal moment in my life. Everything changed. Okay. Wow. Um, I, I love the grass cutting story, right? And how entrepreneurial you were. But then, yeah, you know what? I think Instagram is full of billionaires, right? With the rented lambos and, and all these things. And, uh, and you were sort of living that lifestyle. But you started the, the pod talking about relationships, right? And there's one thing to be flashing a relationship shallowly on Instagram and posing versus actually contributing and bringing value to those relationships. Can you expand a little bit on what that moment was like and how you now think about relationships? Yeah. You know, people always say it's, it's not what you know, but who you know. And, and I completely disagree. I think it's not who you know. It's who knows you. Hmm. Mm-hmm. No. I knew Tony Romo, the quarterback of the Dallas Cowboys. He was my client. He flew on my plane. But if out of context, you said to Tony Romo, Hey, you know Andy Eldord, right? He would not know who Andy Eldord was. Right. Right. If you said Andy Eldord with Marquis jet, maybe, right? But like, I'm, I was his jet guy. I was not Andy, his friend, right? Right. And I think that that was kind of a turning point for me was, I want to be known. I don't want to know. And I think that that, you know, making sure that I'm doing enough in relationships, make sure that I'm, you know, adding value enough to where people are, you know, I definitely know Andy, right? With is something that I, I, you know, in the back of my head, I'm always kind of thinking about, right? Because I, for me, the greatest compliment that I could ever receive is a referral. Right. Is someone saying, I really think you should meet Andy. And here's why. Right. And so I think that, you know, being able to be easily referred, right? Easily introduced. Um, and, you know, other people choosing to have their network generosity flow towards you. Is a really good witness test of how you're, of how you're moving through the world of people saying, Oh, my gosh, I really want to introduce you to this guy named Andy. He lives in New York. And I'm grateful that that happens, right? That, you know, people like, I don't know my buddies traveling. And, you know, he runs XYZ company or XYZ fund. He's going to be a New York city. Can I connect to the two of you? And it's like, yeah, absolutely. I love that. You know, and I think the success, the success that I've had in my life, you know, is going from one good person to another. And having it feel organic, right? How can it feel like, uh, you know, something that you, you would want to do? It's like, I love it. I'm interested to Andy. That for me is, is kind of the pinnacle of success that I want to achieve. Yeah. My business coach also says the exact same thing when you walk into a room. How many people are going to know who you are? Right? And, and I mean, obviously you want to be in bigger and bigger rooms. Like, don't just go to your local business club. Of course, they're going to know you, right? A room full of strangers. And, you know, to your point, you're saying, you know, referrals, but I think you'd said the buzz word. Introductions. Right. I think introductions is a better way of saying it than give me a referral. Who can I introduce you to? Who can you introduce me to? Because that's the basis of relationships. Um, so let's move, move on to that next point. So you've got this company and what happened? Uh, I mean, it sounded like everything was going great. Uh, you had, you know, at the very end there. What, what was the pitlid point? What, uh, yeah, what happened? Yeah. Well, so, you know, moving to New York City and had a couple of early successes that, um, you know, was a part of a company that sold a Facebook pre IPO, which was good for us and better for investors, but it was good for us. Um, and then, you know, ended up not taking a job offer at Facebook and going to help a small Israeli startup called Waze, uh, expand from Israel and, you know, the, you know, traffic and navigation app, you know, we had three million users. Um, when I joined and, uh, you know, ended up selling to Google for a little over a billion dollars, uh, because we grew to about 60 million users, you know, in the short time that I was there. And, and, you know, so like learned a lot as a team member of two companies that were acquired, uh, but then, you know, wanted to go build something in myself. And so founded a company, you know, it, it also got acquired. And so I was like, three for three. This is amazing. Like, you have startups. You're easy. Uh, you know, but that was, you know, it was all pretty quick. You know, like when I jumped on rocket shows, right? Um, the company that, that ended up, you know, our investor passed away, you know, that we were in our seventh year of building that company when, when everything went down. And, you know, we'd started, you know, with a, trying to build a, you know, a smart grocery shopping list. And we said, you know, there's a source of truth for everything else we buy, but not for groceries. You know, if I want to buy a house, I go to Zillow to see what my options are. If I want to buy a car, I can go to an auto trader or if I want to buy a flight, I can go to Expedia and, you know, I'm going to put my intent to purchase out there and have people to show me what my, my offers, you know, what the offers are. But for groceries, the thing that we buy most frequently, we'd just walk into a store and hope they carry what they're looking for and hope they charge us a fair price. So there's no way to compare one store to the next for our buyer shopping list. And so that was kind of the motivation for what would become basket.com. And, you know, and, and they're working out pretty well. And, you know, we're on, you know, we're moving quickly. We were growing hundreds of thousands of families that we were helping. We were saving people hundreds of dollars. If not thousands of dollars a year, just by using our free app. And so everything was, you know, point of the right direction. But we, you know, where we got caught, thought food, when our investor passed away, was we had truly analyzed the, the category of what we're building. You know, if you were, if you were a shopper who was trying to save the time and money, you knew about us, but investors did it, right? And, and while we had turned on some revenue opportunities, you know, we had really publicized how great a business we were building. And so that's when we got caught, flat-footed, you know, in needing to, you know, to bring on capital and, you know, on budget terms. You know, and ultimately that's, you know, why the business ended up failing and we had to shut it down after the pandemic. But, you know, it was, we learned a lot. But unfortunately, you know, that business probably was just a little bit too early. And, you know, it's another, it's all about timing. >> Well, timing, I mean, we talk about today. One of the things you had said was just, you know, trusting your board and the, I don't want to, you know, be political or anything, but the first person that came to my mind when you said trusting your board was Elon Musk, right? And, you know, the whole thing that's coming out now with OpenAI and everything else. And, and so those relationships and then moving on. So now this newest venture that you have, the one where you did the tombstone, tell us about that and what the big mission is. Yeah, so the new company I built is called Stretch, StretchForrestries.com where you can, we're, we're, we're quietly live in the App Store, if you search for Stretch. groceries. And what we are building is a continuation of what I tried to build with basket previously. We're building a grocery intelligence platform that allows shoppers to know for this week's shopping list, what stores carry all of your products, and what is the total price for your entire shopping list at every local store on the platform. And so very simply, you know, you show me this week's grocery list, we will digitize it, use a little bit of AI and some technology on the back end to go fetch all the prices for those items or similar items to a lot for store brands or regional brands. And say, you know, if you go to Walmart at cost this much, you go to Target at cost this much, you go to Corgaret cost this much. And then you can make that decision, is it price that's more important to you? So turning left to turning right, if you'd say, be $20, $50 every week. Or is it more of this trip? It's about convenience. I want to go to the store that's closest to me to describe these seven items. I'm not going to drive out of my way to save $3. We internally, we call that proximity pricing preference. How far we drive to save how much money? And even for people that are very, very budget conscious, different times of day, different days of the week, or different scenarios, in fact, whether you're trying to save time or whether you're trying to save money, but stretch exists to give agency to the shopper so that they can make the best decisions for themselves. There's lots and lots of technology that help retailers that help the supply side optimize for pricing, optimize for packaging, optimize for inventory. But the demand side, the shopper side, has never had a technology stack. And we're trying to build the first piece of that through our simple free app that's now available for download. And so the inherent differences between basket.com, which I believe was making grocery prices transparent versus knowing your entire grocery list and where you can get it, you know, you have this, I'll call it, I guess, a failure because when you shut down a company, it's a failure. I don't want to be insensitive because I've lost companies too. What was the pivot point in, okay, now I'm just going to do this and I think this one's going to work? Yeah, I, it took me a long time to get over, you know, shutting basket down to, just to be honest, you know, I can't imagine it. It was, it was, you know, it was pretty brutal. And, but, you know, in that process, I worked with my, my executive coach and we came up with four non-negotiables for what it would take for me to ever jump back into being a founder because like most people should never be a founder, right? Like you have to be crazy to founder. Like it's not, it's, you should, you should delay it as long as possible until you're, you're driven mad, driven mad by the problem that you see existing in the world. And it's literally driving you so crazy that you have to go try and treat the solution. It's an itch that you just can't scratch. Like it's just driving you nuts. Yeah, keeping up at night. Yeah. And that's, and that's again, why I say it has to fall over the problem, the solution, right? Like the fact that that problem still exists in this world. Right? So for me, the fact that there is food insecurity in America because of inefficiencies that are embedded in the legacy industry, industry, industry. Mm-hmm. Who doesn't have to cost this much? Yeah, it does not. The richest country in the history of the world. Yeah. 17% of the shoppers that I interviewed last year had skipped a meal in the past month so that somebody else in their house will didn't have to. 17%. Wow. Like people are, and the craziest thing we did a huge study last year, you know, to inform the product in the way that we're moving forward with what we're building, we asked people, how is your grocery shopping habits changed over the past six months? So this was last summer. So like in the first half of the year, you know, did your grocery shoppers, did your grocery shopping habits change? And if so, in what way? The biggest change in grocery shopping habits came from upper middle class and upper class families. And there's very surprising just like we were thinking blue collar and like lower middle class families would have been where like a lot of the changes had happened. But the more we dug into the data, what we realized was blue collar families and lower middle class families had already changed as much as they could. They'd already been making those edits and changes because grocery prices were 25% higher than they were before the pandemic. Yeah. And now those prices are starting to affect upper middle class and upper class families that had previously been, you know, price insensitive for groceries. And 84% of Americans, according to consumer reports, 84% of Americans are afraid they won't be able to buy groceries next month that they bought the same way that they bought them this month. 84% of people are knowing that they're going to have to trade down, they're going to buy less, they're going to have to, you know, cope with different strategies. Their budget for food is the same, but they're getting less, you know, strength, inflation and, you know, all of the different ways in which food is too expensive. And, you know, if you think about it, you know, there really isn't a source of accountability, right? You know, retailers are not, you know, trying to figure out how the lower prices like the prices are up, we're going to stay up. And so part of what I hope that stretch stands for is shoppers just knowing what their options are and being able to have the power that technology is now giving so that they can make the best choices for themselves. So they can vote with their checkbooks, like they can vote with their feet. And I think that's going to be, you know, especially as we move into the, you know, the future of agent at commerce and we move into the future where, you know, the wall of the garden means that used to be, you know, the dot coms for the retailers or the, you know, the retailer apps become less and less of the destination and more and more decisions are made, you know, on recipe websites or with a smart shop, smart grocery shopping list like stretch or inside of, you know, your favorite AI interface. You know, they're going to be changing that are necessary and I believe that stretch is going to be right in the middle of a lot of time. You know, I love teaching and I feel like we're doing a master class here, Andy, because so audience, I want you to grab a pen and sort of, I hope you guys are taking notes and those of you who are watching on YouTube here, just to catch this because I mean, we've got a guy here, Andy, who has been on three rocket ships. He's got a ton of experience and the best experience, of course, is founding and then having to shut down a company, right? You know everything and audience, I want you to hear like he's talking 17%, 84%, like Andy knows his numbers. He knows his market. He's clearly done the research. He's trying to figure out exactly what his clients want and his core avatar and I would, I'm assuming, Andy, but you would know this when that changes, you're going to pivot, right? Yeah, the speed with which the technology world is changing, you know, we're a ten-month-old company, but from founding the company in April of last year to now March this year, just stepping into the entire world of change. Agente commerce was not in the way that people were using 11 months ago. And AI is better today now than it was even a month ago. Order orders of magnitude better. There is a lot of height and there's a lot of noise in technology and all of the foundational models and the, you know, the, the, and tropics versus open AI's versus GROC versus Gemini. Let all of them fight that out, right? You know, they're all swappable in, you know, in your solution. You need an LLLL of some kind, but like, it's also done like you're going to figure out which one fits there and plug in the proper one and when that doesn't work, plug in another one. It's going to be there. Yeah. Get your architecture product. Yeah. Don't worry. Don't worry exactly about, you know, that piece. And I think that that's what, you know, what we've spent a lot of time is thinking, thinking about, you know, all right, where is AI best used? And where is it? It's a nice to have, but, you know, for, you know, there's other, you know, more traditional ways that you can do it. And maybe one day those traditional ways will be so much better than it makes sense to fully plug in AI, you know, in those places. But I think that, you know, if you asked me a year ago, you know, wow, are you building the next unicorn? I would, I would say absolutely. You know, where I'm sitting today one year later with everything that's coming and, you know, where technology's going, I, you know, like I got to say, I think we're building a definite core. Like I think that, you know, we just have set the opportunity is even bigger than it was a year later. And that's a really great feeling, right? To feel like you're skating not just to where the puck's going, but where all the puck's are going, right? Like, and there's two things that I know for sure. AI's going to change everything and people are still going to feed their families. And if we can use the first to make the second that much better than that's a really fun product to be working on. It is it is and I love the again bigger picture purpose You you mentioned a players you mentioned how fast people Exited and left you right the betrayal right I could almost feel it in your words The last segment here before we we stop I just want to talk about the concept of a players how you attract them. How do you keep them with you? One of my mentors has you know, it's not an old concept, but just giving Some of your core management or even the entire company, you know Because everything we're all building these companies for an exit, right? You've had so many exits already Like maybe the concept of B-class shares or some kind of pool there. What's your opinion on that? Yeah, I think One of the things that I know this world is that people do what they're incentivized to do and And if you don't understand how someone's behaving it means you don't understand what they think their incentives are Mm-hmm And and I think that that has helped me you know in a lot of different circumstances to be to really just like press pop like I don't understand Why this person's behaving in this way like what what am I missing about the way that they're seeing the world and You know right now is incredibly challenging to recruit a players It's really really hard. I would concur and and I think that that you know I was speaking with a CTO of a public inter-e company and it could that you know there you know They are seen gently in the world that I want to be in and I said you know If you were if you were me and you were trying to recruit technical talent, what would you know? What would your strategy be? I said Andy like you're gonna tell spot because It's never been easier to to get a prototype built. It's never been easier to vibe code something over the weekend to show somebody your vision And so you have two types of Executives right now you've got people that are going to be a founder of their own thing And they're just biting their time until it's time to go do that thing Or you know people that are letting themselves be money whipped into you know huge positions at the you know The big companies that everybody sort of yeah, and they're like I don't know if they want to pay me seven figures to Sit around and vibe code things. I'll do that too and so you know those are two kind of your two options and so finding people who You want to join your team is a big part of you know those that we've recruited is they believe in the mission that we have right they Could go do anything right like we just had two new executives joined the speaks they could go do anything like like literally like they were joking about the job offers that they got like while we were at lunch yesterday Like literally the job offer came in via text like yeah, I you know, I was okay that I got I had your number I'm recruiting me for this and they're like oh gosh those people are yet right yeah, I know that people are gonna try to recruit my team But we are all so aligned around this Problem that we're trying to solve and those mission met where we're trying to build thing of build towards And the fact that it's also a really really great company and you know is has a lot of different ways that we can build for a future exit That is you know is an advantage that I'm really grateful to have right now because I don't know that I'd be able to recruit the talented the talent that I've been able to recruit if it didn't have that mission Driven component to like truly solving a problem that helps real people in this world Well, and as you're saying that I'm just thinking about my Companies that I have obviously I'm in property management. So you know, there's a core thing to try to solve homelessness But what happens if you're listening to this podcast and the widget that you've invented doesn't really inspire anybody Now what do you do right because what is or are you saying find a mission if you truly want to attract an A player Yeah, I think I think it's becoming more and more mandatory You know the the The ability to go from 0% proficiency to 80% proficiency in something Is the same order of magnitude of skill that it takes to go from 80% to 90% And to go to 90 from 95% and from 95 to 98 right and 98 to 99 is yeah, it's it's as hard to do each of those next jumps and A players want challenges That give them the chance to to level up again And and I think that the best players the best Talent that's out there right now is looking for really really hard problems to solve Because a lot of the easy stuff has been solved right like yeah, I love people who made email more efficient for me But man, I could not get out of bed in the morning to make email efficient right that like that for me is is is not is not a mission that I could you know Send my life for it on you know you're not you're not lying awake at night going how can I make you know more efficient for people yeah Yeah, but I think you know, but I think there's an opportunity right for people who you know to take a look at what they're currently doing When saying hey, is this the highest invest use in 2026 of my talent talent and treasures Hey And I I could do anything is this the thing that I want to spend even one more day doing Because life is not yeah, if it's not don't quit immediately, but you do have to start doing the work To think about if I wasn't doing this and I could change to to eradicate any problem from this world role that I spend my time doing Great now how does the thing that I'm doing today the skills that I have today and network I have today Attached to that problem to that challenge that I realize is the thing that I might be on this earth to do And start that work while you still have the paycheck Start that work while you're you know still in a position where you know you can you can make some moves and if you can solve that problem while you still have your day job like Congratulations, that's amazing right there's a lot of things that you can do nights and weekends, you know with with AI and you know having agents run while you're at work, right yeah But you know, but I think I think you know we are There are too many things that are still long in this world and they feel like more and more of them show up every single day That we all need to be working towards solutions for and and I really hope that you know A players and talented people and people with great networks start to Step more into taking that responsibility because it's it's taking all of us in order for me to just to change You know, I have a very key manager that's been with me for about five six years and I'm sure you have one on your team as well But he started with me Just as an assistant like we're talking a resume that's like I'm just like why are you even Why are you applying to this right any game? The stock well I want to work through the company and know everything and I want to be able to run the place one day Well, he eventually started running the place one day But What he said to me was is something that I I think what you're talking about Andy is He said Garrett you're not giving me financial compensation which you are I'm getting emotional compensation here and he said a lot of a players Go for the emotional compensation versus the financial compensation So I think that's what you're talking about I think that's really well said Really well said All right final question before you wrap up. I always ask every guest this question um So Andy this is the investing to win podcast. The definition of wealth that I have Come back to over and over again is optionality Whoever has the most options is the wealthiest person in the room And I don't mean opt-ins you know like stock opt-ins I mean like choices for choices for what you can choose to do next and and this was derived some from you know to my private jet clients They didn't you know to your point about you know Millionaires on Instagram. They weren't flying private to make things selfie and show people they're rich right They're flying private because it managed to do a tea time opened up at Pebble Beach And they got a text message while they're at dinner tonight They could have the jet waiting for them and make it for the 6am tea time tomorrow They don't have to make sure they don't have to try and get get on an American flight and you know Make it to their port and then drive like they could literally fly or be at home for their family because they took the key meeting in another state Right 100% right it gave them options that was what you know the private jet Offered to them But I started to think about that like at every stage of life right if you are a high school student and you make in You're making really good grades and you're involved in you know the right right programs You're gonna get into more colleges and so you're gonna have more options and you can choose you can choose What your next path is you don't have to just go to to the one place that you got to do right and if in college you Are doing well with your grades and you're you know doing well with your internships You're gonna have more first job offers right and after your first job you're if you do a good job You know you will be wealthy when more people recruit you when it's time for you to move on to what's next and you know for me in the startup game You know I you know raised a couple rounds of funding for for stretch and I did did it with zero hold calls right no Cold emails right I just reached out to people in my network that I've been cultivating but with the past 15 years I had options and You know in some of those people that I reach out to they then introduced me to other investors who said, "Oh my gosh, you've got to see what Andy's building, check this out," right? And the compliment was paid, right? So for me, everything that I try and do is, if I'm debating whether I'm going to make this decision or not, the question that kind of runs through my head is, "Does it give me more options than I have right now or less?" And it figures me more options than it's probably the direction that I'm going to go. Love it. No, I've always told my wife that the more options you have, the less stress you have. Right? "Oh, I have, you hear this. Oh, I have no choice." Well, if you have more choices to quit your job, keep your job, jump off into Armstrong Merrill Journey, whatever it is, then you, yeah, very, very well said. Very, very well said. Thank you. All right. Well, it's been a great hour. I really appreciate you coming on the podcast today. Very enjoyable. I love your story and I hope that people, while obviously, put your information about stretch and, yeah, best of luck with the startup. I think you guys are going to do great. I appreciate that, Gary. No, thanks so much for having me on and really enjoy this conversation. All right. Thank you.

Podcast Summary

Key Points:

  1. A startup founder lost his largest investor and board chairman in a plane crash, which also caused the loss of other investors who followed that lead.
  2. The company missed payroll and struggled to survive, eventually failing after taking harsh terms from new investors and facing the COVID-19 pandemic.
  3. Key lessons include
  4. The founder emphasizes falling in love with solving the problem, not the company or solution, and that failure comes from failing to imagine failure.
  5. A practical exercise is having the team write the company’s obituary to uncover hidden risks and foster resilience.

Summary:

In this podcast episode, Andy Elwood recounts the devastating loss of his largest investor in a plane crash, which led to the collapse of his startup’s funding and eventual failure. The investor, a Silicon Valley legend, had promised a $5 million bridge loan, but after his death, other investors withdrew, leaving the company unable to make payroll. Andy shares three key lessons: always expand your network beyond current supporters, have contingency plans for every critical role, and stay in love with the problem you’re solving, not the company itself.

” Despite the tragic setback, Andy’s resolve was driven by a deep commitment to helping families afford groceries, a problem that persisted even after the company shut down. He reflects on his early entrepreneurial journey, starting with a lawn-mowing business at age 12, and how that shaped his resilience. The story underscores the importance of preparation, adaptability, and passion for purpose over profit.

FAQs

His largest investor, a Silicon Valley legend, died in a plane crash after promising a $5 million bridge loan. This led to a loss of investor confidence, missed payroll, and forced the company to take harsh terms from new investors.

Always have backups for investors, key employees, and other critical roles to avoid being caught flat-footed if something unexpected happens, as failure often comes from failing to imagine failure.

The tombstone exercise involves writing an obituary for your company, including its lifespan, cause of death, legacy, and how it could have survived longer. It helps teams surface potential failure points from different perspectives.

Being in love with solving the problem keeps you motivated even when your company or solution fails, as you focus on eradicating the issue rather than clinging to a specific technology or organization.

At age 12, he started a lawn mowing business, earning $30,000 a year in high school by going door-to-door. He later hired his brother and friends, learning sales and team building early on.

While optimism is common, it's crucial to imagine and plan for worst-case scenarios. This includes having backups for investors and employees to avoid being blindsided by unforeseen events.

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