From Warren Buffett to World-Changing Startups: Andy Ellwood on Purpose & Legacy #legacybuilding

Welcome to the Legacy All Stars podcast. We feature inspirational stories from people who dedicate themselves to helping others. Here is your host, Alan Pavloski. Hello, hello, Hello. Welcome to the Legacy All Stars podcast where we shine a light on inspirational people who use their success to make a positive impact. Today's guest, Andy Elwood, has built a career around uncovering overlooked opportunities and transforming them into meaningful solutions. From selling insurance and private jets for Warren Buffett, to launching startups later acquired by Facebook and Google, to developing a thriving executive coaching practice in New York City, Andy's work has always centered around helping people unlock their potential. Today, Andy is co founder of Stretch, a company creating the world's first pre purchase intent platform for agentic commerce. Starting with grocery shopping, Stretch gives everyday families the kind of insight and influence traditionally reserved for large corporations, establishing a new standard for trust, fairness and connection in consumer tech. In this conversation, we will explore Andy's philosophy that the future is already here, just not evenly distributed. And we dig into how his unique career path shaped his mission to ensure technology serves everyone. Andy, welcome to the show. Good to have you.

Thank you so much for having me. It means a lot to be here.

All right, fantastic. I know we're going to hear about Stretch. I want to ask you a few preliminary questions first to give context to our audience. You've had a remarkably diverse career, from selling jets to building startups, to coaching executives. What through line connects all of those chapters for you?

I would say that curiosity is a superpower that when you have the opportunity to learn something from anyone that you meet, whether in just every life, you know, your barista, your Uber driver, or the executive who's sitting next to you on an airplane, there's something that they know that they're really good at that you have the opportunity to learn from. And so I approach just about every conversation I have as, what's this person's thing that in however long we have together, they might be able to share with me and impart a little bit of wisdom and just that curiosity has unlocked a lot of doors because I asked maybe one more question than others would have and that served me very well in my career.

Yeah, we have two ears and one mouth for a reason, right?

Exactly.

Yeah. When you think back to the early part of your career, what moments shape your belief in seeing possibilities where others see limitation?

I was always ambitious in a way that kind of surprised my parents. Always thinking about maybe one or two steps ahead, and not because of the way that I was raised. It's just kind Of a little bit of. That's just who I was. I started my first company when I was 12, you know, a lawn mowing company in Texas. And it was making almost as much money in my senior year of high school as most people made when they got out of school. So I almost didn't go to college. I was like, wait a second, like, why would I wait four years to make this amount of money? And I was always looking for ways to have feedback loops. So I got into sales because you either sold something or you didn't. You either increase the size of your pipeline or you didn't. And that feedback loop really has kind of fueled a lot of the ways that I think about, just the way I structure my life, the way that I think about approaching problems, the way I think about building my network, the way that I think about the friends that I choose to spend time with or the ways in which I get involved with projects. I really love the idea of being able to just think about what are the incentives? Right? Like if you know what the incentives are, you'll know what the outcomes could be. And I think that that has been for me, something that very early on in my career I really loved thinking about, okay, what do I control in this situation? There are so many things that I have no control over. But if I can find the one thing in a situation that I can control and I can optimize for that, I'm going to feel better about being in new territories, I'm going to feel better about being around things that are different than anything else that I've experienced. If I could look for what are the incentives in the situation and what are the things that I can control in those outcomes. And I think that started from selling life insurance. Because if you can sell life insurance, you can sell just about anything else. Right? Everything else is an easier conversation than have you thought about your death recently? Everything else is easier, but I got pretty good at that conversation. I was rookie of the year my first year out of college, selling more life insurance than the other 23 year old in America. And just kind of a little bit of competition. But a lot had to do with understanding incentives and understanding how to keep score in situations that were maybe a little bit more ambiguous.

Yeah, I mean, look, life insurance is a tough sell, but on the other hand, it's an important cog in one's financial future. And so I've always been a believer have it myself and of course very highly recommend it to anybody who wants to protect their family from unexpected Consequence.

So yeah, yeah, I still have the policy that I sold myself at the tender age of 24. Nice, nice.

You know, I've been dying to hear about Stretch in a little bit more granular detail. Tell us about Stretch, especially about pre purchase intent. And what problem did you see in the marketplace that sparked the idea?

When you think about the innovations that happen, there are a lot of really good features that get built disguised as companies on the seller side of things. There's a lot of things that help companies sell more things to shoppers. And building any company is hard. But building a company where you know exactly who is going to buy this and here's the thing on their P and L that you're going to change by 5 to 15% a year. There are amazing people building amazing companies that do that, but they're features inside of an existing system category. Defining companies that I really look up to, that I have been studying and thinking a lot about in my career are companies that build an entirely new way of thinking about things. I'm inspired by companies like Zillow who thought about the person buying the house as opposed to the person, you know, the retailer selling the house. They said, hey, home purchaser doesn't have good information. They don't have everything that they need to know about this except for what's being controlled by the person who's doing the sale. And obviously that's tainted information. Let's give them access to information. Let's have them be able to make those choices themselves. Expedia. Same thing with travel. The purchasers were not necessarily saying colluding, but they were keeping a lot of information away from the traveler. And same thing with like autotrader and cars.com right? When people have information, it disrupts an industry, but it allows the industry to operate much more efficiently. It allows aligned interests in disclosure of information. Along those lines, the top four uses of household gdp. It's your home, it's your travel, it's your automotive, and it's groceries. Groceries hasn't really changed that much since the Roman Empire. If you really think about it, we all still go to a predetermined place of marketplace that has a bunch of stuff and we hope that the guy at this stall is selling it to us at a fair price and that it's good quality. But we're not going to all the other stalls first. Comparing and contrasting similarly, most Americans are within 5 miles of 10 to 12 different grocery stores and they're not checking all the stores before they make their purchase. They're kind of just going to the one that is close by or the one that they know the manager, the one that has good lighting in the parking lot. And so my question was, what would it look like to give shoppers the information so that before they left their house they could know that turning left or turning right out of their driveway could save them 20 or 30%? So that where I thought about that was on the grocery list. Right? Getting things started on a grocery list. There's 26 billion trips to the grocery store in America every year and 90% of those have a grocery list of some kind. When you think about the amount of information that is being lost on the back of an envelope or a post it note or in an Apple Notes on your phone or a text from your spouse, all that information could be the power that the shoppers need in order to get better prices, have better selection, and actually even have some collective bargaining power if it was organized in a better way. And that's really what we're thinking about a lot with Stretch to create a simple, beautiful, elegant, smart shopping list that if you tell me what's on your list this week, I'll tell you every store close by that carries it. And then eventually we'll build in online purchases as well. And it's not always about price. It's about having the perfect information to understand that, hey, today I've got a little bit of extra time, so I'll drive a little further to save 50 bucks. Or I just need to know the store that's in this neighborhood that carries the things that I need to go to this birthday party or to go to the potluck or on my way home and I just need to pick things up. Not every store carries all products. And so being able to have all of your choices in one place, very visible, searchable, just like you would on Kayak.com when you're buying a flight. What would that look like for groceries? And so that's kind of what the inspiration was.

Cool. I know. It empowers family. It's going to help save them money. Is there some kind of aggregating feature that allows you to say, here's my list for today. Which store best optimize my budget based on the list that I'm shopping for today?

Yeah, exactly. So we're doing comparison across your entire shopping list, not just individual items. You know, that wouldn't make a whole lot of sense. You're not going to change stores because you could save 25 cents on penne pasta, but across a $250 shopping list, you can save 20% by turning left instead of turning right at the intersection. That's possible.

Makes total sense.

Down the line, we can imagine a world where Walmart just announced their partnership last month with OpenAI, basically signaling that where purchases are being made, it's not just going to be Walmart.com and not just going to be the Walmart app, but there are going to be other places where that information should exist. And we're really excited about that because once the retailers start to signal that they're open to this. Transparency, yes, transparency. I don't think that ChatGPT is going to allow me to compare Walmart's prices to Target's prices. So I think that there will be some controls there that the retailers will still have, but that's where we're hoping to be able to step in. As more and more retailers say this is the future, we're going to say we're the agent or we're the advocate for the shopper. So if you were to give me your shopping list this week, our agent one day will go out on your behalf and say, here's a family that typically spends $400 a week. These are the types of things that they buy. What's the best that you can do for them? We've spoken with the former co founder of Priceline and he said that once you get a few stores that are willing to participate like that, everybody else has to fall in line and that's what we believe is going to happen and it's going to happen pretty quick.

Yeah, makes sense. You often talk about technology serving everyone, not just the privileged few. Where did that conviction come from for you?

It goes back to being the kid who had a little bit extra money when I was growing up. Like I bought the first computer that my family had. I paid for it with money I made from mowing lawns. But I realized that that was a privilege, right? A privilege that I was able to go earn some cash, that I had the free time, the flexibility and the parents that supported me at an early age.

I saved up and bought a truck on my 16th birthday. I was the only kid who bought their own car on the 16th birthday. Amongst my group of friends. Again, I had the privilege of being trusted with that power, I guess the ability to move where I needed to move and that allowed me to earn more money mowing more lawns and being able to drive my younger brother and his friends around to have them help me with mowing lawns. I always Kept finding that there was certain tools, whether it was a new computer or it was a truck, or eventually buying the first blackberries or buying of the first iPhones. You know, buying better and better technology was always a privilege to me and I worked pretty hard for it. I didn't grow up in a family that was giving me anything. My parents were very supportive. They're like, hey, if you can go figure that out, go for it. But I think that what I've realized is that people don't rise to the level of their potential. They rise to the level of their expectations. And so I'm always looking for things that cause me to increase what my expectations are of the world and encourage others to do the same. Based on the family you were born in, based on the neighborhood you were born in, based on the country you were born in, or the religion or the gender, whatever it is. There's a lot of old stories that have been told about what that means. And I think that we're seeing more and more as we evolve as a society, as we evolve in understanding the information of what societies look like all around the world, that there's a lot of different ways that things can happen. And as individuals, we need to find the ways that work best for us and the things that we can be most proud of.

Yeah, I love that. That's great. What has surprised you most about consumer behavior as you've built Stretch?

We spent August talking to over a thousand shoppers in 47 different states. And we published a white paper about shoppers point of view. And I think one of the things that was surprising when we got dug into the results and got to talk with shoppers, but then also talk with grocery executives from across the country and in all different parts of the supply chain, was that grocery is everyone's problem now. When we asked shoppers, how much has your behavior changed over the past six months? So since January of 2025 to August of 2025, the people whose behavior had changed the most, upper middle class and upper class families. I was struck by that. I was like, why on earth is that happening at the upper ends of the marketplace? I would think the rising cost of groceries, like we're talking about lower income families, blue collar families, lower middle income families, but it was the upper middle class and upper class families. And when we dug into the numbers, it's because lower class families have traded down as much as they possibly can already. They're already.

Coupons only and discounts only and store brands only. But the upper middle class families are for the first time feeling the pinch in a way that they really had it previously. And food has become something that stresses out. It's 84% of Americans right now are stressed out by the cost of food. And that's just from the entrenched inefficiencies in a legacy industry like the grocery industry. There's not a lot of accountability. There isn't pricing transparency. And so there isn't anybody forcing those innovations to actually lead to lower prices. In 2005-2025, it's almost a 3x. The profit margins for grocery stores, they're always razor thin. But you know, to 3x over that period of time, when it should be innovations happening that are making it cheaper, that are making it more efficient, that are making it quicker and faster to store and refrigerate food. It's surprising that in the richest country in the world that we have people who have fears about their next meal. And that's the thing that just keeps causing me to jump back in and try and build what comes next.

Yeah, well, you've built companies that were acquired by giants like Facebook and Google. What have those experiences taught you about innovation and timing?

The big thing, especially with those big acquisitions, is when you're starting a company, you have to understand what your time horizon is and how long you're willing to. To fight that fight. I was pretty frustrated when we found out that Waze was being acquired by Google because I felt like we were just getting started. But because of the way that the company had been founded, because of the terms that they'd raised their investments on, there really wasn't a choice. The company had to get acquired an early team member, but I wasn't a founder. It was fine for people at my level. It was fun to say that we got acquired by Google, but I really wish we would have got to keep building because mapping technology was just getting started when that acquisition happened in 2012. And you think about all the things that now use a map and it's ubiquitous. To be able to be an independent map company would have been such a fun ride through everything that's happened since then. Probably would have partnered with Uber. We probably would have been able to be the map instead of Lyft and all the delivery apps. But somehow the FEC allowed the merger to go through. Number one, Map Company. Number two, Map Company. But it was kind of a forced hand, you know, And I didn't have any involvement in those discussions. But, man, I was kind of frustrated because I was like, we were Just getting started on all the things that we planned for partnerships and the way that we were starting to work with both TV stations, we were working with bus routes for cities and governments. But you gotta be able to structure your company well in the early days so that you have choices when those acquisition offers do appear in the later days.

Yeah, definitely.

Coaching high level executives also has given you a unique window into human potential. What common patterns have you seen that hold people back?

I think that if you look at the top performers and the people who are leading whatever role they're in, leaders come in all shapes and sizes at all different spots on the corporate ladder. But I think that a couple things that they have in common is one, they expect more from themselves and from, from everyone else than most others do. Going back again to, we don't rise to the level or potentially rise to the level of our expectations. They expect their teams to always be at their best, and they're constantly looking for ways that they can unlock the potential of their teams to meet those expectations, to have everybody on their team have those expectations of themselves. And so I think that that's one thing, but the other thing that I know about most leaders is that they have an incredible inferiority complex in a posture syndrome just about all the time. It doesn't matter what they've achieved. It's always kind of waiting around the corner to pop in and be like, is that enough? Is that enough? And so I think one of my favorite investors, Josh Wolf, Lux Capital, he frequently says, chips on shoulders, put chips in pockets. And I think that if you spend much time with some of these leaders, there's always something that's underlying that's driving them, whether it was their relationship with their family growing up, it was. They got passed over for a job early on in their career. They gave it a shot one time and it didn't work out, but they're trying again. You know, there's always something that's underlying, and sometimes you'll find out what that is, and other times you won't. But as a coach, I have to say I had some of the best due diligence you could possibly have on these companies, because I knew what the founders and the CEOs were afraid of. And so it was fun to be able to be that confidant where they could actually say the quiet thing out loud with no repercussions. Being able to hold that space. They're not sure if they believe it, but it has to get outside their head before it can really be evaluated. And Some people are like, I'm going to quit my own company tomorrow. It's like, okay, how does that feel? How does it feel to have it out in the world? And sometimes it was just like, okay, I needed to say it out loud. And that's all there was. And other times it was, all right, let's start working on a plan. Let's start putting but putting things in place so that that's a possibility. If and when that time comes, you can do it in the least disruptive way possible.

Yeah, got it. You know, this show is all about purpose and legacy. What role does purpose play in your work today? And how has your definition of purpose evolved over time?

I think it's an ever evolving definition and one that is constantly informed by each experience that we have. Know that when we bump into somebody cosmically, for a 30 minute podcast or for a 30 year relationship, you know, there's the opportunity to glean a little bit, you know, And King Solomon says, as iron sharpens iron, so one person should sharpen another. And I think about that a lot that, you know, each person that I spend time with, I want to get as deep as I can, as fast as I can. And I feel like my purpose is to make room for many. There's a quote by Eberson that says there's always room for a man of force, for he makes room for many. And I love that thought that, like, being a force means that you can do it on behalf of others. You know, I've been told that I have big brother energy, and I love that. I'm very okay with that being how people kind of see me and reference me because I'm the oldest of four kids. But I also give really good hugs. And I'm six foot three. And so sometimes, you know, I just get to, you know, get in there and give a hug to somebody who needs it. But I try and kind of live life with that type of generosity that, hey, I've got some extra energy. I've built some capacity in my life. If I can offer it to somebody in a moment where they need it, that's a huge, huge thing for me. My favorite movie is the Princess Bride, and Fezzik the Giant is such an amazing character played by Andre the Giant. And there's a scene where the protagonist is trying to get through a crowd and he's stuck and he's small and he can't see over the crowd. And Andre the Giant just goes, everybody move. And the crowd parts and the protagonist is able to go, do what he was meant to do. And that's kind of like what I try and think about for the people that I surround myself with. Like, can I part a path or be a part of opening up a path for people to find their higher calling? And that's what I feel like I've been given the capacity in my life to be able to do. That's really the closest thing to the consistent purpose that I think I've had through everything that I've worked on.

Wow. He had me at princess bride, man. One of my favorites. It's always been in my top five.

Yeah. Yeah.

Always will be.

I really hope that they never try and remake it.

They should not. I actually was just talking to my wife about this. There's a live event, it's somewhere in napa valley here that I'm going to attend Because I'm just a princess bride freak. But basically, there's a show at the uptown theater in napa Where Cary Elvis is doing live. They're going to show the movie, and then there's going to do live Q and a afterward.

And I just love that.

It's going to be wonderful. Wow. Let me just ask you this one last question before we move on. If you could distribute one insight into the world more evenly, Something you think everyone should understand, what would it be?

You have what it takes.

That the highest highs and the lowest lows, you already have what it takes that you have a 1000% success rating on making it through the hardest days you ever had. And it is probably the thing that I question the most every time I step in to do the next thing is, do I have what it takes? And I've done some things, but it's still a question that I ask all the time. And I think that if we're all honest with ourselves, we actually know that. But sometimes it's easier to just be like, ah, no, I'm not going to muster the courage that's necessary. And so I think that I see far too many people stop just before it gets good. And I want to just encourage everybody to just take one more step, Take one more intentional step towards the thing that you literally, you alone were put on this planet to do. That is what I would love to impart to everybody that they have what it takes for the next thing, and the next thing, they can just start to build that muscle.

I mean, persistence is everything. It's one of those things where.

And the people that I've encountered, and of course, those that have grown and those have had foresight and hindsight in order to make decisions. We all get to a place where we have self doubt, but it's those that can evaluate whether what they're doing is the right thing first, of course. But then once you determine it's the right path, you gotta, you know, chop wood and carry water, as they say.

100%.

Yeah, for sure. Andy. Man, this has been really fun. We come to the end of the episode. I really want to thank my special guest, Andy Elwood. He's been an inspiration, as always. Until next time, I hope our audience continues to pursue excellence in making a difference. Just like our guest, Andy Elwood. Check out Stretch. Definitely take a look at that platform. I'm looking forward to looking at it myself. I'm Alan Pavloski signing off for Legacy All Stars.