Season 2, Ep. 14 | Stretch(ing) Grocery Spend in an AI Era Transcript

More Elephant Intro

​[00:00:38] Jason Rudman: On this conversation of the More Elephant podcast, I'm excited to talk with Andy Elwood.

Andy is building the first true shopping intelligence platform, as he describes it, a way for everyday families to shop smarter and save real money in an industry that's remained unchanged for far too long. This conversation is going to be a journey from Texas through a number of startups, some tragedy that I think Andy will share redefined, reenergized, and puts him on a path to what he's trying to do now with his company called Stretch.

So Andy, welcome to the More Elephant podcast.

​[00:01:18] Andy Ellwood: Thanks so much for having me. I'm excited to be here.

​[00:01:20] Jason Rudman: We're excited as well. Can't wait for our audience to listen to your story and your journey.

So as we always do, before we even talk about Stretch, I want to start with you.

When you look back and I mentioned, all the way back to Texas —and knowing a little bit where your family squeezed every drop out of the grocery budget as you told me—what's the throughline in your career or life that makes this moment and what you're building with Stretch the inevitable company that you were going to build?

​[00:01:50] Andy Ellwood: I think my parents instilled in me a true spirit of curiosity and it always being okay to ask, but what else is possible? 

Neither of my parents have business backgrounds. My mom, stay-at-home mom for the whole time that she was alive. She stopped working two days before I was born. And my dad was a landscape architect, worked for a big architecture firm.

When I started being like, it's really fun to make money with a lemonade stand. They're like, okay, well, we'll help you set that up. And then, when I said that my one dollar ($1) a month allowance wasn't enough for me and I wanted to go make some money mowing loans, they said, okay, great, we'll help you set that up.

And, you know, we made some mistakes along the way. I've started paying taxes when I was twelve because my dad would make sure we did everything with integrity. But he had me pay taxes on the same tax scale that he was paying taxes as a thirty-something professional. Eventually we figured out that I'd been overpaying taxes for six years when I graduated from high school. 

So, lots of learnings —what do you do with a kid who's overly ambitious but I learned from it at an early age.

Like you know, the grass stops growing in October. What else is possible? So, I started setting out people's Christmas lights. I started cleaning out gutters. I was like, oh, well if they don't want to do it, they'll give me money for it. That's a great business.

And so, I've always been looking for the next thing that I could do. The curiosity around what drove value that would cost somebody to be willing to separate with dollars is a little bit of the game that I was playing as a kid that turned out to be pretty good when it came to building businesses and selling people things in my adult life.

​[00:03:14] Jason Rudman: What was growing up like? I'll share with you that, growing up was all about trying to make ends meet. And I think that, like you, has shaped what I'm involved in, which is helping people lead a better financial life and democratizing financial services.

So give us a sense of what growing up was like and how that has also shaped this very specific domain that you're in.

​[00:03:40] Andy Ellwood: Yeah. So, we were homeschooled. I tricked my parents into homeschooling us. After fifth grade, my friends at church in fourth and fifth grade, they were homeschooled. And I was like, what's that like? I don't understand what you mean. What does it mean to be homeschooled?

And they said, well, you know, we start school around like nine, ten o'clock and we're usually finished by two or three. And I was like, wait a second—I get dropped off at school at seven a.m. and then I'm there till three and then I go home and do homework until five. What do you mean you're done with school at two p.m.? That sounds better.

And the idea fascinated me. And so I kept telling my parents, let's just try it for a year. Let's just try it for a year. I'm the oldest of four kids and I'm very grateful that my parents did that because it opened up the opportunities for me and my siblings to each take ownership of our own education and pick paths that allowed for that.

We used homeschooling as a way to learn everything; every single thing that happened throughout the course of any given day was a chance to learn. All the way to the monthly grocery trip.

My mom had a cookbook called Once a Month Cooking, and it showed you how to layer recipes together so that you could buy groceries one time at the first of the month and have all of your dinners for the entire month. The math the science and the social studies of it; the different ways that my mom used a trip to the grocery store to be a part of me and my three siblings’ education is something that I always smile about.

I have very fond memories of trying to guess what's the total price going to be, and are we under budget or over budget? Then do we have to put something back? You know, do we have to go get one more thing?

Also, in hindsight, we always had exactly enough. Never more, and I know for a fact now, having spoken with my parents about this many years later, lots of times where we didn't actually have enough. But I never knew.

My parents did everything that they could to make sure that we felt we had everything that we needed but there was not extras. You know, my parents made it cool that my friend Josh's hand me down, Josh got this stuff last year, you get it next year. And I'm very grateful to Josh and his mom, Debbie for always being generous with our family that way.

I think that finding opportunities to learn inside of every moment is something that I'm very grateful to my parents for. And thinking outside the box!

We had a lot of games that we played in our backyard and around the neighborhood that cost nothing. Because there wasn't any money to spend on other things, you know? And I'm grateful for that.

I never find myself very bored. There's always something that you could do for free anywhere that you go in the world.

[00:05:59] Jason Rudman: Yeah. So, Stretch is a new endeavor. We should acknowledge that you proudly announced September of last year that you're going to help millions of Americans stretch their budget and enable them to be like your Mom, right? Do more with a finite amount of money.

Take us back to pre-Stretch for a second. There's a whole journey here, In the immediacy of pre-Stretch, you were an executive coach. There's a story before that and you talked to me about, this is a problem that never left you.

So, what was going on in your day-to-day that made the problem continue to bug you enough to say, this is something I need to do something about.

And then if you could connect that back to this is not your first rodeo. So if you would connect those two, that would be great. 

[00:06:46] Andy Ellwood: Yeah. obsession with the idea that is now Stretch is, at this point, over twelve years old.

The question that I kept asking, even thinking back to when I was a kid was, how much does this grocery list actually cost?

I'm willing to say, here's what I want to buy and, for most other parts of commerce, for most other industries, if you say, here's what I'm intending to purchase, there is some place where you can go for a source of truth around what people are willing to sell, what the price will be and what the trade-offs are if you go with one choice over another.

Think about Expedia for travel, Zillow for homes, GoodRx for prescriptions or Gas Buddy for fuel prices. Most of the major things that we buy, most of the major things that are part of our household budget, we have some source of truth of how much is that going to cost and then we make the best decision with the information that we're given.

For groceries, the act of buying groceries is the same as it's been for hundreds of years, which is you walk into a store that is relatively close by to you, you hope that they carry what you're looking to purchase, and you hope that they charge you a fair price. But, the only way you would know to actually go to the store and the only way you would know if they were charging to a fair price is if you walked into another store, rebuilt that same basket, walked up to the checkout and said, how much does all this cost?

And then you're like, oh, yep. The other store, I'm gonna drive back to the other store. No one's gonna do that. But that's your choice.

[00:08:15] Jason Rudman: Well, we do it. As shoppers, we do it mentally in our head.

So I was reflecting on that, right? The inflationary pressure on groceries right now, the moment that we're in, I'm trying to remember it in my head that I know that it's a dollar cheaper to buy a gallon of milk at Ralph’s than it is a Whole Foods for what it's worth.

And, I just want to acknowledge I brought Whole Foods into this; that is, I'm a privileged shopper. I do have Whole Foods as an option but Whole Foods is pricing itself out of our weekly shopping basket. The same basket of goods in the last year has gone up about a hundred dollars and it's every week. We're a family of five. That is a lot of money every week.

[00:08:54] Andy Ellwood: It really is.

Last summer, when I was thinking about jumping back into build Stretch, I interviewed over a thousand shoppers and we put them through, you know, kind of a formal survey process because we we want to make sure we're really solving something. 

One of the big questions that was a huge aha for me was we said, this was in August of last year, if you think back over the past six months, the first half of this year, how has your grocery shopping changed from what you were doing at the beginning of 2025 to what you're doing now in the middle of 2025?

We looked at it across a bunch of different metrics— across blue collar families, low income families, middle income and upper income families—and the biggest change, the people who changed the most in their behaviors were middle and upper class families.

[00:09:39] Jason Rudman: Yeah.

[00:09:41] Andy Ellwood: And at first, we're like, wait a second, like, why is that true?

And, when we got just a little bit further into data, it's because blue collar and low income families have already changed as much as they possibly can to be able to afford groceries.

They've already done everything. They've traded down on brands, they've traded down on the stores that they shop at, they've traded down on how frequently they purchase. 

And, seventeen percent of the Americans that we spoke to last year have skipped a meal in the past month so that somebody else in their family didn't have to.

[00:10:12] Jason Rudman: That is a stunning stat and we don't talk enough about the high levels of food insecurity in this nation. You can see it in places like Spokane, for example. Spokane is the bread basket of Washington and the majority of what they grow gets shipped out to feed the rest of the country, the rest of the state, high levels of food insecurity in the very place where the food has grown.

It is a reality and I so appreciate the insight that you have there to acknowledge that those with fewer means have traded out and often live, Andy, in relative food deserts where they have fewer grocery store options, where that trade off actually gets compounded.

The ability to not trade off gets compounded because—I've got seven different grocery chains within a one mile radiance of where we live here in Los Angeles. Seven.

[00:11:05] Andy Ellwood: Wow. Seven. Wow.

[00:11:07] Jason Rudman: Yeah.

[00:11:08] Andy Ellwood: Yeah. And you know, like you said, in the richest country in the history of the world, seventeen percent of the people we talked to have skipped a meal.

Over twenty four percent of Americans have used buy now, pay later for groceries in the past year. Buy now, pay later is not meant for weekly groceries. It's meant for that unexpected car maintenance that needed to happen or the last minute trip that you needed to take to be with an ailing relative. It's not meant for this week's groceries.

The fact that feeding your family has become such a master's in mathematics equation…absolutely crazy.

So my obsession with there should be a source of truth around how much do groceries cost and you should know before you leave your house which of the seven stores in your area has all the products and what the total price for your entire basket of goods is. And, if it used to be at Whole Foods and now you've moved to Ralph's, there's five other stores. How much does it cost there? To me why is that not possible? Why would that not be a thing?

And that obsession, asking that question, started in twenty thirteen, after I'd sold my third startup. I was very blessed that the first three startups that I worked on building were acquired. First one got acquired by Facebook, second one got acquired by Google, and the third one got acquired by private equity.

I was very blessed. It was awesome. I was part of those teams. I learned a ton, it was early in my career and it wasn't like don't work, again, it was learn some things and maybe buy your mom nicer bouquet of flowers, right?

But, you know, learned a lot about the process and learned what it was like to build companies and raise money and be a part of acquisitions. 

And so I said, what's a big problem that's worth solving? A friend of mine recently become a Dad. He had a receipt; I remember it was a $326 receipt.

And he's like, is that how much this costs? And I was like, I don't know. I'm young and single, dude; I don't know how much that costs.

And he's like, well, let's figure it out. So we actually did the thing where we went to all the stores in the area…recreated the receipt, wrote down the prices on all those things on that receipt, found that there's a forty percent difference in price within a three mile radius of his home.

All the stores that we saw were ten stores within three miles and there was a forty percent difference in price. And we're like, no way.

We showed it to friends and they're like, no, that's crazy. So, we grabbed their receipt and we grabbed other people's receipts and we kept recreating these lists and we're like, oh my gosh!

It's always at least twenty to twenty five percent without sales or coupons or discounts or loyalty points. It was just like easy. Then you add coupons and discounts and loyalty on top—forty percent.

Why does this not exist? So, we said we're gonna build it and that became a company called basket.com. At our peak, we were serving six hundred-and-fifty families. We were crowdsourcing all the prices and we had a community of shoppers helping each other; if you were in a store and you saw a great price, you could scan the barcode and type in the price and we would add to the platform and then that would help another shopper with their shopping list. 

[00:14:06] Jason Rudman: We should acknowledge—because we're going to talk about how technology and AI has advanced your ability to do this—we should acknowledge, in twenty thirteen, a relatively analog digital way of doing that, where you had a community of soldiers scanning barcodes and updating the platform.

[00:14:24] Andy Ellwood: Yeah, absolutely. I mean, looking back on it, it is insane to think about what we did. We crowdsourced one hundred and eighteen thousand grocery stores across the country

[00:14:32] Jason Rudman: My goodness.

[00:14:33] Andy Ellwood: …and we kept those prices current. We reverse engineered the pricing algorithms and amazing that we were able to pull it off. The reason that we did it was we were trying to help real families, like the ones that I grew up in save money on the groceries and we were averaging saving families over a thousand dollars a year. And that's real money especially because it's after tax dollars. And like a lot of things, you're moving fast, you're growing and if you're a venture backed company, you gotta keep raising money.

Our investors were super behind us. So we hired better and better people. We grew the team. We were on the Today Show, Steve Harvey had us on his show, a lot of fun to meet Steve Harvey. It was fun to be able to see how many people were like, oh yeah, this is awesome, I love what these guys are building.

Board meeting December of twenty eighteen, our two investors are like, we're gonna do a big investment next year but we'll give you a small investment in January, five million dollars in January, and then we're gonna do a monster investment in the summer. Keep building, keep this momentum going. 

We confirm that they're going to wire us the five million on the first Thursday of the month—first Thursday of twenty nineteen. 

Monday of that week was our lead investors' sixty-eighth birthday and he's a gregarious fellow and threw himself a birthday party in San Francisco. He owned a vineyard in Northern California and he flew himself and his best friend up to the vineyard for a birthday dinner with the family and they crashed the plane and died on the way there, three days before they were going to give us the money that we needed to make payroll and to pay out bonuses for the team that we'd hired and to keep the growth engine moving.

And, it wasn't just that we lost an investor and we had to scramble, but he was kind of our third co-founder; he was the first person who invested. He was with us the whole way. It was the end of his investing career. We were going to be his last big company; he'd been investing for 40 years.

All of a sudden we're scrambling. We haven't been talking to other people and we had half of our team quit on us over the next few months because we were slow on payroll. But all the while, we were keeping our shoppers, saving money—Robin Roberts gave us a shout out on Good Morning America. All sorts of good things were happening over here and then the fundamentals of the business just were deteriorating in the background.

My old co-founder, this was twenty nineteen so we'd been working on it for six and a half years, we put in our own money and we got other people to help us out a little bit. We survived twenty nineteen, and we're like, all right, twenty twenty is going to be our year. And then this global pandemic happened.

When your entire business model is predicated on data acquisitions by sending people into stores.

And everybody using the platform was using it to go into stores to buy their groceries, and everybody was trying to save money before the pandemic, then because of COVID, the government was giving out free money and people were less price sensitive. They didn't care how much it cost. They just wanted it to feel safe.

[00:17:16] Jason Rudman: Yeah.

[00:17:17] Andy Ellwood: We didn't survive. And so it was an unfortunate end of a really, really good thing. So basket.com, we shut it down.

At that point, I've been building companies for twelve years and I hadn't really done much else. For those twelve years, I averaged one hundred and eight seven days a year on the road because I was the young single founder. You know everyone who I'd worked with, they were married with kids.

[00:17:38] Jason Rudman: And you're like what else am I gonna do? I'm the single guy.

[00:17:40] Andy Ellwood: Sure. Yeah, sure. Like, sure, you want me to go give a speech at the Sydney Opera House?

I'll do that this weekend and I would just like fly over, do a thing and then fly back.

[00:17:48] Jason Rudman: Right?

[00:17:48] Andy Ellwood: I was just on planes all of the time and it was fun. But, once I got off the merry around, I was like, oh, I should get married and become a dad and see my friends in person, and it was just all of a sudden I'm just like, whoa. It's a whole different world.

So, I'm very grateful that I had the opportunity to recalibrate and reset and became an executive coach, which was an incredibly rewarding place to take all of my hard-earned lessons—some good, some bad—and be able to try and be, you know, I always joke that I have big brother energy, like to be the big brother who's done it before.

Be like: Hey, come along [and] let me at least share with you what happened to me and then we'll figure out how you should do it. You can't do it the same way I did it, but we can figure out the way for you to do it.

That was really rewarding. And about the love of my life, we got married and our daughter is now six months old, which is absolutely incredible and I'm very, very grateful to be a new Dad. 

But, the whole time that I was catching my breath, if you will, people kept reaching out to me on my website, on LinkedIn, saying “price and transparency for groceries…somebody should do that. I'm gonna do it. I saw that you tried to do it. Can I pick your brain?”

And, I literally wrote back to everybody else: “You're right, someone should do that. It's a huge opportunity. It's still there. This is how I did it. It should be easier now. Technology is so much better than it was in twenty thirteen…”

[00:19:05] Jason Rudman: Okay.

[00:19:06] Andy Ellwood: “…like somebody should go build this company. When you figure out your game plan to do it, call me back and I'll be your first investor.”

And nineteen out of twenty people did not call me back because it's really hard, right? You're taking all of the data from all these different stores and having to make a retailer-agnostic master catalog on the backend, starts with what the shopper's intention is, and then goes out and finds all the stores that carry those products and then assimilates what the total price is for the entire basket of goods at each store.

Groceries is a pretty gnarly old school set of data. It's not super advanced. It was the last to come onto e-commerce, right? Delivery for groceries is still pretty new compared to every other industry that has had e-commerce as a part of it so figuring out that data piece is hard.

But, I'm very grateful that the person who's now my co-founder for Stretch worked in the grocery industry and had his own idea about how AI was going to change the data side of things. He came with a really thoughtful approach on the data side of things and the way that AI could supercharge what I had tried to do with Basket; kinda had the business side and he had the technology side and we decided to join forces.

And so, summer of twenty twenty five, we launched the theory. We incorporated the company, started writing code. [An] amazing team that helped us move very, very quickly to build up the database of products and prices and then another team that was incredibly talented at building a consumer app. We soft launched it over the holidays and we had over eight thousand people on our wait list. So we're now slowly rolling out nationwide and it's incredible to see people writing in and just say, “Hey, thank you so much for building this. My family needed this, with groceries still being twenty five percent higher than they were pre-pandemic.”

With inflation doing what it's doing, with the uncertainty and the world being what it's been, with AI doing all the crazy things that it's doing in so many different industries—the two things that I know [is] AI is going to change a lot of things and people are going to keep feeding their families and if I could use AI to help people feed their families, then game on.

[00:21:11] Jason Rudman: Right. So your point about the pandemic and behaviors change. I think about Instacart for example. I can go onto Instacart, I'm not price comparing for sure. What I'm doing is that I don't have to go to the store.

By the way, sacrilegious as it may be, I've actually never used Instacart because I like to go to the grocery store and smell the apples and feel the grapes; I'm old school, right? So I'm primed and I have downloaded Stretch and I am going to be one of your users because I'm doing this right now in the gray matter and comparing. I do the shopping in the household so I actually do know what a gallon of milk costs. It's a little crazy. It's one of those twitches that I've got. And, when I see it, to your point, it changes, which is incredibly dynamic.

AI has changed even what you were doing at Basket and I think this More Elephant audience, many of us trying to figure out that there's this revolution happening. How has that fundamentally, at least a high level, rewired how you've gone about Stretch versus your approach to Basket.

[00:22:12] Andy Ellwood: Yeah. So yeah, at its core, the way to think about what AI is trying to do is AI is predicting the next word, right? That's the large language model, LLM. It's predicting the next word. It hasn't thought about the five words from now, it's thought about the next word, but it's trained on the entire internet that the likelihood of the correct next word in this sentence is this. And when you extrapolate that to thinking about it as your phone, a friend, thinking about it as your expert in your pocket, thinking about it as thought partner, that's what AI can do.

So on the business side, going back to how we started this conversation, I'm always thinking about what else is possible and so sometimes, I'll take something that I wrote. I'll take a blog post that I'm putting out. I'll take a social media post that we're gonna put up for the company, and I'll copy it and I'll drop it into my, I use Claude as my primary AI.

And I'll be like, what else would be possible to make this more powerful? I'll read it and then it's attached to other things that I've written in the past. And, it's like this doesn't feel as authentic to Andy as maybe it could. What if we changed this sentence and talked a little bit more about what it was like for you growing up as a kid?

I'm like, oh, I didn't even think about that part because you know, I'm moving pretty fast. And so it's kinda a one-o-one thing.

When we get into the data processing, we have already, in less than ten months, a million products into our database.  Everything from Honey Nut Cheerios to sku’s for bib lettuce to dozen eggs to every version of almond milk that exists in the world. All of that is in a database that when you, on your Stretch shopping list, like milk, it queries thousands of products that think about what is probably the correct answer for you. 

So, that's on the query side, but then the more that you use Stretch, the more personalization, AI, kicks in and it gets to know this is likely what's going to be best for your family. For me, for example, I have a gluten-free member of my family. If I know that they're coming over, take this week's shopping list, make it gluten free and it can convert all that very quickly because it knows what the alternatives are. Those types of personalization’s that you can toggle back and forth is just the beginning of what's possible.

Where it's starting to get really interesting is with agentic commerce, and that's where you can actually give AI assignments and they can take multi-step process so they'll complete a task, they'll deliver that task to another AI, another AI will do the next part of the task, then it comes back to you. All of that happened while you were sleeping, while you were running to get a cup of coffee.

I ran a process earlier this week for a new webpage that I'm putting up on the site, and I said, this is the type of page that I'm building. Here's all the requirements for the way that we build webpages. It needs to be able to have this functionality. It needs to be connected to these databases and I want you to show me a plan and then I'm going to give you the green light to do it. Three minutes later it wrote me a plan. I said, go for it.

I went out to a coffee meeting, I came back and it was done and the extrapolation of what's possible when you start to use your imagination, say, well, what if an AI could do this? It gets really interesting really quickly, and it is like being a group of early stage interns, that gets smarter the more that you interact with them. If you think about AI as intern that does things for you that you don't feel like you want to spend your time doing, it's a really great place to start.

In the grand scheme of things, AI is a tool, right? Like we don't say, oh my gosh, that company uses an Excel. It's like no, Excel's just a tool that makes math a lot easier for most people and when you understand how to do the macros, the formatting and the calculations and plug it in an Excel file, it looks like magic the first time that you ever saw that done. Similarly, if you start to learn the tools and the different things that are out there with AI, that is what is accelerating the speed with which we're trying to serve our shoppers. And every day it's like, could we go a little bit faster so we could serve that many more people?

[00:26:16] Jason Rudman: I think there's so many potential off-ramps to what you just described. One is solving for particular dietary needs. When you're doing that in an analog fashion, you're scanning down the aisle and think about the core of what you're trying to do, which is to essentially save money. The multivariate brain power in an analog world that would be needed to find specific dietary needs is that there's that complexity.

I think about also agentic commerce and the connection to what in a post pandemic world is grocery delivery, right? So, I'm a better informed shopper. I'm building my shopping list based on algorithmic conclusions about what I've done over the past n number of weeks and what's available, and I'm pricing competitively. Then, I just press the button and it shows up on my doorstep.  That feels like an experience to explore.

[00:27:12] Andy Ellwood: Yeah, I mean, Jason, have you been reading our business plans?

[00:27:15] Jason Rudman: I have not, but again, just in conversation with you, that would seem to be where agentic commerce is real.

[00:27:20] Andy Ellwood: Yup. Imagine if an agent, the Rudman family, family of five, spends about this much per week on groceries, in this part of Los Angeles and, as a result of you all living close to those seven stores around you, the Rudman family agent went out marketplace and said “I'm representing their family, people they spend about this much per a week on groceries. They have these dietary restrictions, these preferences, these brand affinities. They're open to brands in these categories. They're not overly loyal to a certain type of pasta. They're not overly loyal to a certain type of seltzer. What can you do for us this week?”

[00:28:03] Jason Rudman: My mind is already blown. Andy, we should talk. But you can use the Rudman-McCray family as your test case. I'm already sold. I'm already sold.

So, do you remember the first customer who said yes to Stretch or the first group of customers that said yes to Stretch? What did that moment feel like especially given what you were solving for at Basket?

And did anything surprise you about how they were actually using Stretch once it was in their hands?

[00:28:30] Andy Ellwood: Yeah. The first time somebody sends you a screenshot of them using something that you spent months building, it's pretty special, it's really special. And you know, there are thousands of apps that get built and don't ever get used and it's just really, really tough.

So, last summer while we were building the app, I was posting very, very frequently on TikTok and just telling people what I was building and the first time that I put a screenshot, I just held up a screenshot of the app and I said this is what I think it's gonna look like.

You know, I'm a new dad in his forties. I'm not supposed to go viral on TikTok. I don't have any followers. I had five hundred followers but that TikTok got a thousand comments, got one hundred and fifty thousand views, which is wild. And people kept tagging their friends: one person wrote not all heroes wear capes and somebody else wrote you're doing the Lord's work.

And, they said, I would pay for this app. Make sure you filed your patents. Strangers from across internet were just like, do it man. Do it. Like go for it. We need this.

[00:29:34] Jason Rudman: Had you filed your patents, we just need to clarify, had you filed your patents?

You had filed your patents. Okay, great.

[00:29:39] Andy Ellwood: Yeah, yeah, yeah. And so, the most important thing that any business can do is just keep talking to your end user. That's it. keep talking to 'em and if we changed it this way, would you love that?

And so in the app right now, we have feedback buttons throughout the app. We're really grateful that even now, with the thousands of shoppers that we already have on the app, the feedback is different than other feedback that I've received on the internet. The internet is not always the kindest place, right? It's not always the nicest place.

A lot of times feedback is not really that helpful but the part that just continues to be encouraging to me is that the feedback that we receive from anybody who's downloaded Stretch is, thank you so much for building this app. I need this, and here's how I think you could be better.

Reid Hoffman, the founder of LinkedIn, once said that if you're not slightly embarrassed by the first thing that you put out in the world, you waited too long to put something out in the world. And I think that's true especially with a consumer-facing company, you want to put it in the hands of your users as soon as possible to understand what buttons they push? How frequently they come back? What's their favorite feature? What's obvious? What are parts of the app that nobody ever finds?

And so, as soon as we put it in the App store, we started rebuilding it almost instantaneously. We keep iterating, keep putting new things out and a pretty big update in February that I'm really excited about. I think that's what our job is—to just keep listening to our shoppers, being very, very committed to the vision, but flexible on how we get there.

[00:31:07] Jason Rudman: So there's the prioritization of the features as the company has started to grow,

and I'm reflecting on the different environment that you're in previous startups to where you are now.

How is your role or how is your thinking changing in ways you didn't expect? And is there any part of this experience where it's been hard to let go of what you used to do or how you used to think in order to incorporate what you're hearing and basically create MVP two, MVP three, MVP four?

[00:31:43] Andy Ellwood: Yeah. I think that being an executive coach in between the last company and this company gave me the chance to sit with other founders, gave me the chance to sit with other investors, gave me the chance to sit with other executives from different companies, and to learn. I was there in the coaching capacity, but I was learning from them every single session, right?

Learning how they ran their company in a completely different industry, in completely different world with completely different metrics and [a] completely different team. I got to see the best of the best. I believe that the good get coached; that the best of the best people are always looking for their chance to get coached by somebody who's a little bit better than them, coached by somebody who knows something that they don't know.

There's a book by Tim Grover called Winning. Tim Grover was the personal trainer for Michael Jordan, and then Kobe Bryant, and in the book, he breaks down the difference between the way those two worked. Their ethic. And so, being a coach, I got to watch people hungry for ways to be better. I take a lot of notes and I got to incorporate those notes into thinking about what type of executive do I want to be this time around?

You know, that's probably the biggest changes. I've changed from being the “scrappy, single, I'll hop on a plane anytime to go anywhere” version of the founder that I was for basket.com, to I really like being in the office with the team and point up to the whiteboard, looking at the nitty gritty numbers and understanding, that's where this is an opportunity, that’s where the breakage is, that's where we can get an exponential return in this way. 

When we think about it as a team, we have a rule of three here at the company that if you do something three times a week, every week, you have to build an AI [agent] to do it for you. We're challenging each other to be even more efficient? How can we outsource things that we shouldn't be doing anymore because we now have a bunch of digital assistants, digital interns, who can do it for us. All we have to do is write the correct prompt and let them take it from there.

[00:33:46] Jason Rudman: I love that. So if you are doing it manually three times a week, you have to figure out how AI can do that for you. That is quite remarkable.

I'm going to assume fatherhood has changed you as well, On some level as a leader, how do you reflect on fatherhood in terms of how you show up as a chief executive?

[00:34:05] Andy Ellwood: I've never been more efficient with my time.

[00:34:08] Jason Rudman: Ah.

[00:34:09] Andy Ellwood: Every minute that I spend doing anything that's not holding my daughter is a minute I'm trying to figure out how to streamline. And, you know, she's just the best little baby of all time and I want to hold her as often as I can. 

I love the work that I get to do. I love the team that I'm building, but I want to know that I'm done for the day so that I can just go be fully present with her. And, I work really, really hard to earn that right. Every day.

And it doesn't work every day. Sometimes, you know, I make it home in time for bedtime, and then I go right back to work at the dining room table. But, you know, I haven't missed a bedtime yet. I've had to travel a few times for work, but if I'm in town, I'm making it home for bedtime.

[00:34:52] Jason Rudman: Yeah.

[00:34:52] Andy Ellwood: And I can log back on afterwards. So, the prioritization of any moment that I can do it better, that I can do it faster, that I can give it to somebody on my team to do.

I think that for a lot of early stage founders, they're just afraid to let go of the control and they have a tough time trusting their team because they're not going to do it quite the way that they would do it. 

I'm really glad that my team's not going to do it the way that I would do it. They're all better at things than I am. I hired them because they're better than me at the things that they're good at.

As a CEO, there are only three jobs that I have—ruthless commitment to the vision, don't run out of money and make sure your team's not blocked. That's it. That's the only thing a CEO needs to do. If you spend all your time worrying about those three things, hire amazing people around you, and you make sure that they're not blocked in doing their work, you win.

[00:35:41] Jason Rudman: As you think about what's next for Stretch, what's something you're really intentional about not losing as the company scales? 

[00:35:49] Andy Ellwood: Our obsession with the families that we're serving. The really interesting part about the space that we're stepping into is the grocery industry is a one point eight trillion dollar industry. Has it really changed? Even Instacart, even curbside pickup is just a slight variation on the way it's always been. It's not actually a fundamentally different way of shopping for groceries.

It's still, you have to pick your store and then you shop from that store's list and you can't mix and match, and you can't compare, and you can't have all the information in front of you the way that you do in every other industry, in every other purchase that you make. A slight variation on the way it's always been. It's all changing.

Shoppers are going to be more in control than they've ever been and there's going to be so many different opportunities, so many different business models that will pop up because people are going to feed their families, people are going to buy food. The information asymmetry has been in favor of the industry for a very long time, and now, with information transparency that shoppers are realizing they have, they're going to realize that they're holding all the power in this relationship. And, they're gonna look for tools that allow them to take advantage of that.

That's where we hope that we continue to fall—is on the side of the shoppers because it is good for the whole industry. Informed shoppers making conscious decisions, saying here's what I'm planning on purchasing. What can you do for me? 

[00:37:20] Jason Rudman: I'm wondering if there's ever a point…so I'm thinking about I've got a Whole Foods app, I've got a Ralph's app. I've got a Gelson's app, I've got a Pavilions app, I can keep going. Again, I have seven grocery stores within about a mile.

I'm wondering if we get to the point where a partnership with something like Stretch, I could imagine Ralph's, for example saying we are not going to build this, we need Switzerland to build this aggregated data. And to your point, we're going to “demand price” groceries like the airlines. I wonder if we'll get to that stage where you'll be an engine for demand pricing at scale, which ultimately to your point, puts the power back in the consumer's hands.

[00:38:02] Andy Ellwood: That is a future that we can imagine. We've been talking with one of the co-founders of Priceline and he said that the reason that Priceline eventually worked was Priceline was able to say, here's a business traveler that travels three times a month, it’s first class, typically rents a full size car and likes to stay at the suite in a Marriott. You could win their business if you cut your price by this much. 

[00:38:29] Jason Rudman: Yeah. 

[00:38:30] Andy Ellwood: The Rudman family spends this much on groceries. They live in this area. What can you do for them?

[00:38:35] Jason Rudman: It gets back to the core of your idea, right, ultimately having grocery chains compete for the basket. You're on a tear, you've raised a round of money. What's next for Stretch and how do people who are not on TikTok connect with you to learn more?

[00:38:58] Andy Ellwood: We’re very much in the ‘get the fundamentals right’ part of the business. Our promise at Stretch is your grocery list priced locally and that is way harder than it sounds. That is the very simple promise that if you give me this week's grocery list, I will show you local prices that you want to buy for your whole list.

We are already covering twenty eight thousand stores in, across the country, but there's another sixty or seventy thousand stores to get to. We are doing that as fast as we possibly can, but we're a small team. So, look for partnerships, look for funding. Also, you know, we think a lot about the team that we want to build and the community that we want to build and we're pretty intentional that this is not just a good for the world company, but it's also a really great business.

So, we're gonna be raising more money from investors and that's always a fun process to go to. It's a slog no matter how much momentum you have, but it's something that I've done more than a couple times, so I'm grateful to know the ropes there. So, we're finishing building out the team in New York City, and it's going to be a really fun year.

I mean, my life has ebbed and flowed over the course of years, and I was really grateful when I woke up on January the first, twenty twenty six, that on December thirty first, twenty twenty six, and all things hopefully go in the right direction when you do pretty much the same time…I'm going to be building Stretch. I'm going to be Eloise's dad, I'm going to be Maddie's husband.

I'm going to be living in New York City. I'm going to be living in the apartment that I live in. The variables of this year are much lower than they were last year.

My daughter's six-and-a-half months old. My company is ten months old. A lot of things changed last year. So grateful for this year to just be heads down building what we're building.

[00:40:35] Jason Rudman: So people can go on the App Store or Amazon store. They can download the Stretch app. They can sign up, they can use the Stretch app, and they can find you at stretchformore.com.

[00:40:49] Andy Ellwood: Stretchformore.com. That's right.

[00:40:50] Jason Rudman: Awesome. I feel like maybe a year from now, we're going to invite you back and we're going to say you said it was gonna be fairly calm…was it really as calm? 

Eloise is six months old. Oh, just wait, my friend. Just wait. There's a big difference between six and eighteen months. 

[00:41:10] Andy Ellwood: The internet lives forever, so that comment makes me back to homemade. 

[00:41:13] Jason Rudman: I promise you, we're going to check back in and we're going to replay that little snippet and say, okay, you said it was gonna be pretty plain sailing. What's happened in a year?

Andy, what I appreciate most about this conversation is there are so many More Elephant moments that you've taken us through in your journey where the power of Stretch is you just sat and listened to people and understood that there was a problem to be solved, that you actually fell in love with. And it is something that is going to change people's lives because of what we said—finite amount of dollars, prices are increasing, dietary needs are evolving, and the consumer retaining power over that purchasing decision, I think, is a journey worth finishing.

So congrats on getting Stretch out the door. Appreciate you taking the time and we can't wait to see what you do next.

[00:42:15] Andy Ellwood: Yeah, appreciate it. Thanks for having me on and excited to continue to share the journey with you.

[00:42:19] Jason Rudman: Awesome. Thanks again. Talk soon. 

​ More Elephant Outro