Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: Scaling to $122M ARR IPO with $6M in Net Burn, Olo. The Ultimate Journey of Capital Efficiency, What Worked, What Did Not Work and How Leaders Need To Reshape Thinking Around Resource and Attention Allocation About this episode Noah Glass is the Founder and CEO @ Olo, the interface between restaurants and the on-demand world powering millions of orders per day. Olo is an incredible tale of capital efficiency, at IPO the company had a net burn of just $6M with $122M in ARR. Noah raised from some of the best in the business with names such as David Frankel @ Founder Collective, Danny Meyer, Scott Shleifer @ Tiger Global, all on the cap table. Prior to founding Olo, Noah was International Expansion Manager for Endeavour Global, launching the first African Endeavour affiliate. If that was not enough, Noah is also on the board of Portillo's, Share our Strength and the Culinary Institute for America. In Today’s Episode with Noah Glass You Will Learn: 1.) The Founding of Olo: What was the founding a-ha moment for Noah with Olo? What did David Frankel do that compelled Noah, now was the time to start Olo? What have been some of Noah's biggest lessons from working with David Frankel? 2.) Capital Efficiency: Scaling to $122M ARR with $6M Net Burn Why did Noah and the team not raise more money in the early Olo days? How does Noah advise early founders who are concerned if they do not raise, their competition will? What are 2-3 of the core levers that allow Olo to be so efficient? What can others learn from them? What would Noah have done differently fundraise wise, with the benefit of hindsight? 3.) Decision Making: The Secret What does Noah mean when he says; "capital allocation and attention allocation are intertwined"? How has Noah changed and evolved his decision-making as a leader? How does Noah use a CEO coach? What do they discuss? How often? What works? What does not? What decision did Noah make that proved to be the wrong one? How did he come back from it? 4.) Noah Glass: The Father and Husband How does Noah do so much as CEO and also not lose an inch on being an amazing father and husband? What does Noah believe is the secret to a truly successful marriage, while also being public markets CEO? How has Noah changed as a father and husband over the years? What has worked? What has not worked? Item’s Mentioned In Today’s Episode with Noah Glass Noah’s Favourite Book: Setting the Table by Danny Meyer
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Harry Stebbings? We are back. This is 20 VC with me, Harry Stebbings, and I'm so excited for the episode today. Now, capital efficiency are two words that we rarely hear in today's market, but this is an incredible tale of capital efficiency and true company building. When this company went public, it had a net burn of just $6 million and an ARR of $122 million. Now, that is rare. And so with that, I'm so thrilled to welcome Noah Gloss, founder and CEO at Olo, the interface between restaurants and the on-demand world, powering millions of orders per day. Noah raised from some of the best in the business, including David Frankel at Founder Collective, Danny Meyer, Scott Schleifer at Tiger Global, all on the cap table. And prior to founding Olo, Noah was International Expansion Manager for Endeavor Global. And I want to say a huge thank you to David Frankel, Danny Meyer, and Scott Schleifer.
0:45 Harry Stebbings? Some amazing questions, suggestions from them, and I really do so appreciate that. But before we dive into the show today, quantifying and predicting company growth can be a challenging task. With CoreSignal's historical headcount dataset, investors can easily see the historical growth trends of more than 20 million companies worldwide. Enriched with in-depth company information, this dataset is ideal for getting the complete picture of any selected company, including its growth and location trends over time. CoreSignal's historical headcount dataset includes continuously updated snapshots of headcount and social media follower trends dating back to 2018. With it, be sure to enhance your investment analysis and decisions with hard data. Go to coresignal.com/20vc and download a free ebook
1:30 Harry Stebbings? that explains the various benefits alternative data offers for VCs. Once again, that's coresignal.com/20vc. And speaking of incredible tools like CoreSignal there, from websites and online stores to marketing tools and analytics, Squarespace is the all-in-one platform to build a beautiful online presence and run your business. There are three things for me that really stood out about Squarespace. First, mobile optimized websites. All websites are optimized for mobile in a way that content automatically just adjusts so beautifully, so your site looks great on any device. Pretty awesome. Second is the email campaigns. Squarespace makes it super easy to grow and engage your audience with Squarespace email campaigns. And finally, SEO tools. Takes the guesswork out of SEO, so you'll get found in search by more people more often.
2:14 Harry Stebbings? And if that wasn't good enough, go to squarespace.com/20vc for a free trial. And when you're ready to launch, use the offer code 20vc and you'll save 10% off your first purchase of a website or a domain name. And last but by no means least, the incredible team at Angel List. They've been a key partner for me in managing my investments. I love using the Angel List platform because it abstracts away all the complexity and operational burden of fund management. So whether you're running SPVs, a traditional venture fund like me, or even a rolling fund, Angel List has you covered. I'm also though, super excited about their new product, Angel List Stack, which is purpose-built for founders. With Angel List Stack, you can create a fundraising-ready startup in just a few clicks. Angel List handles your company's incorporation, banking, cap table, and fundraising process, all in one single place.
2:59 Harry Stebbings? This allows founders to focus on building. If you're a founder, you can launch your company at stack.angellist.com/20vc. Whether you're a founder or funder, you're in great hands with Angel List. But that is enough for me, so now I'm so excited to hand over to the one and only Noah Glass, founder and CEO at Olo.
3:21 Speaker 01 You have now arrived at your destination.
3:25 Harry Stebbings? Noah, this is such a joy to do. I've heard so many great things from David at Founder Collective, from obviously Scott at Tiger, so thank you so much for joining me today.
3:32 Speaker 02 Well, Harry, what an honour. I'm a great fan of your work and I'm humbled to be here, so thank you so much for having me.
3:37 Harry Stebbings? That is so kind of you. It's amazing how far a posh British accent goes, but I do want to start with some context. It's incredible to see Olo today and all that you've built, but where did it all start? How did you come to found Olo and what was that aha moment for you?
3:50 Speaker 02 Yeah, well, it first started when I first moved to New York City and that was in 2003. And when I moved here, I was one of those weird people in 2003 carrying around a Palm Pilot, personal digital assistant. And I was really inspired by this device and particularly an application I was using on it called Vindigo and really looking at points of interest around me on a map and seeing restaurants and Zagat reviews, ratings and that sort of thing. Coming to believe that we were all going to have devices like this in our pockets. Enabled devices and once we did that they would be more than just communication devices or content devices, but fundamentally they would become commerce devices. So that was sort of like one seedling of inspiration.
4:30 Speaker 02 The other side was experiencing a busy coffee shop that was in my building every morning. And I was living on Wall Street at the time, which was a very weird place to live. And every morning there was this crush of people trying to get coffee at the same time. And so I thought if I could get that coffee faster, if it could be prepared and ready and waiting for me, and I could skip the line, that would be a great experience. I also had worked in the restaurant industry. So when I was 17 years old, back in my hometown of Newton, Massachusetts, I worked as a pizza delivery driver and I saw that there were operational inefficiencies on the restaurant operation side of things. So putting all those things together, I really felt like, okay, a mobile device that let me order ahead, pay ahead and have them prepare my order as I was on route, that would be better for me as a consumer and it would help them improve their throughput capacity.
5:14 Speaker 02 There's really a win on both sides. So I wrote the original business plan in 2003 and it's sort of sat there on my proverbial shelf. Until 2004, I moved to Johannesburg, South Africa. I was working full time for Endeavor. I started to see this as the opportunity to manifest this vision that I'd had back the year earlier in 2003. I showed an early copy of that business plan to David Frankel. I was all set up to go to Harvard Business School the following year. And David said to me, look, if you really believe in this enough to quit your job at Endeavor and enough to tell Harvard Business School that you're not coming, I'll back you. And that was this beautiful burn the boats kind of moment where it made me make Olo my only path forward.
5:56 Speaker 02 And I'm forever grateful for David for supporting me, but also for supporting me and putting me to that test of saying, are you willing to make this your only path forward? If so, then I'm willing to back you.
6:06 Harry Stebbings? I do want to ask though, because you mentioned David Frankel there and he in particular, but every one of your masters actually mentioned your unique insight and vision into how the market was going to play out. My question to you is, David Frankel said, I had to start with this, embrace the suck. What does that mean? He didn't tell me.
6:21 Speaker 02 Okay, well, it really originates, it's a Navy SEAL thing. It's what they say to people as they're going through basic training and it's really about getting. Uncomfortable being highly uncomfortable. And for Olo, it meant if we can endure, if we can outlast our competitors, if we can integrate into systems in the restaurant, point of sale systems that weren't meant to be integrated into, if we can get through that suck, we'll be in a place that nobody else will be able to stay with us. And so it's really about motivating the team that yes, things are bad now, but this is going to serve us well if we're able to get through it.
6:56 Harry Stebbings? Were there times in the early days when you were just going, I really don't know if this is going to work. The restaurants are not biting. It's not getting what I thought it would do from a response. And how did you respond to that? So did those times happen and how did you respond?
7:09 Speaker 02 There were so many times that we felt that way. And we really had to look at these little green shoots of hope and little instances of success and celebrate those wins and almost forget about all of the failures to be able to see things like we're doing twice the number of orders in this restaurant this month as we were last month. What's working well here? What can we take from that small example and extrapolate beyond just one restaurant as we think about scaling up into future restaurants? We were a team that was really good at embracing the suck and having a high pain tolerance, but also celebrating the wins and really being in it together.
7:44 Harry Stebbings? I'm totally carving the schedule up, but you said about kind of how it changes your mindset when you take investor money. You raised very little money compared to the majority of other startups. Why did you decide to raise little and be much more conservative?
7:58 Speaker 02 In the early days, it was just a matter of not being able to raise a whole lot of money. I mean, one of the things that was really an incredible moment in the company's history was we raised in March of 2008. That was our series A round. I believe on the exact same day, March 17th of 2008, when Bear Stearns collapsed. It felt like it was the last funding round that was done for some long period of time after it. And so we raised that money. We had it in our bank balance and we knew we had to make it last.
8:26 Harry Stebbings? How big was the aim? What was the price, if you can remember?
8:28 Speaker 02 It was seven on seven. It was a very dilutive round, but we were incredibly grateful that we did that round, that we got the $7 million on the balance sheet of the company. And that really became. This crucible moment of can we last to the next stage and we can raise again? And how do we make it so that we can really control our own destiny? And we can take these funds and enable ourselves to grow into profitability while still hanging on to this vision that we have and being tenacious around our conviction of one day, every restaurant is going to operate in this way.
9:02 Harry Stebbings? You've mentioned crucible moments a couple of times with David Frankel's first check, that funding around. I'm always in two minds on great leadership. Do you think great leadership is the way you navigate those crucible decisions? Or is it the thousands of little decisions you make throughout the year that add up to the fabric of a company?
9:19 Speaker 02 I think it's making the right call in those crucible moments, being consistent in between and really setting the example for the team about what are our values? How do we make decisions? What is that decision making process built upon? You can emulate that in these crucible moments and in all the other things where you have to weigh in directly as the founder or the CEO, the leader of the company. But really you need to replicate that. It needs to be in the fabric of the company and all of the leaders and all of the decision makers within the company, not just the leader.
9:50 Harry Stebbings? When you think about crucible moments where you made the wrong decision, can you take me to one of those? I'm too interested.
9:55 Speaker 02 We've only made the right decision, Harry. I mean, come on. No, I mean, so look, I remember in 2019, pre-COVID, I came to feel that we were at such a moment in the restaurant industry that Olo needed to go public, that Olo needed to become a company that was not a startup and not a company that large restaurant brands, who were our customers and our prospects, would have any sort of doubts about, are they going to be around next month? We needed to be a company that was rock solid. In order to do that, we wanted to show the scale that we were operating at. We wanted to show audited financials that showed that we were profitable. And of course, we wanted to show that we had a lot of cash on the balance sheet. So I became very fixated on this idea that Olo must go public.
10:41 Speaker 02 That is the thing that is gating our growth with the large enterprise restaurant brands. And I pushed really hard and the board was not 100% aligned on that. There were some that were saying, I think that's right. There were some that were saying, I don't really know, but I'll go along with Noah because he tends to be right about things. And there were some that were dead set against it. Looking back now, it was at best a toss up and maybe would have been too early in 2019.
11:05 Harry Stebbings? Noah, as a leader, you're very much a statesman. You're very much a very serene, calm, almost political leader. Has your leadership style changed over the years? And if so, what have been some big developments in your own personal way that you lead and manage?
11:21 Speaker 02 I think one thing, I was listening to a number of episodes of yours. I remember I listened to the Whoop episode. I was really struck by, as a Whoop user, I was really struck by how Will talked about the disassociation between the entrepreneur and the venture, or the CEO in the business, or the founder in the business, however you want to say it. I really struggled with that early on in a big way. When I was hearing Will speaking these words about a bad day for the business felt like a bad day for me, a good day for the business felt like a good day for me. I was just nodding my head like I have felt that so deeply. In these whiffy-o moments, these moments where it feels like you're gonna go under as a business,
12:01 Speaker 02 it feels like you are an absolute failure. It feels awful. And you need to be able to create a little bit of daylight between you and the business. I think I've been able to do that over the years with a lot of outside help and a lot of support from my family, which is my number one support structure, my wife primarily. With that also, understanding that I didn't have to do everything. I didn't have to make every decision. I could bring people into the company who weren't doing it for the first time on instinct, but had experience. I could delegate things to them. The ability to delegate, I picked this up from what Aaron said from the box episode. It is so critical as you scale the organization. If you want to move fast at scale, you need to be able to be a good delegator. And that's something that I think I've gotten much better at.
12:46 Speaker 02 Those two things of separating yourself from the business and delegating are really closely intertwined.
12:52 Harry Stebbings? I want to unpack them. I love that. I'm super intrigued though. When you say about kind of separating yourself from the business and finding support in your wife. Think about those communications. The thing I worry about is actually worrying her with what I say. And then two, being negative to the extent where she feels she can't talk to me about her problems because I've got too many of my own. Do you see what I mean?
13:12 Speaker 02 Mm hmm.
13:12 Harry Stebbings? How do you think about not worrying her too much? One, and then two, not making it difficult for her to open up just because you're going through a difficult time.
13:21 Speaker 02 Well, I think that's one of my favorite things about our relationship is that we work in completely different fields. Almost because of that lack of direct experience in one another's fields. When we talk about work, we're almost always speaking from first principles, reasoning with a beginner's mind. And that's really helpful sometimes. Sometimes you can have so much of your thinking that has been derived from preconceived notions or things that you think you know, or old assumptions that are no longer valid. And just bringing it to somebody who's from a completely different field and having them say, okay, take me through this from the elemental pieces and let's reason through it is just fantastic. My wife has been a huge supporter, worked in the business in the earliest years as our initial CMO.
14:05 Speaker 02 When we were really just getting started and had a number of brilliant ideas on the go to market strategy, but is a legal historian and just our joke is I sort of think about the future. She thinks about the past and we get to coexist in the present. And that's been a fantastic partnership over the years since literally moving in together on June 1st of 2005. That was the day that I incorporated Ola was the very day that my girlfriend and I moved in together, my now wife. And she has been a partner along the journey with very little expectations. There was no expectation from either of us that this is going to be a huge success. This is going to be a public company one day. I'd say if anything, it was we're going to do this together. And at some point, if it doesn't work, Harvard Business School is always there and you can reapply.
14:48 Harry Stebbings? Obviously, from that relationship, you have amazing children too. I love kids now, honestly. I'm like, I cannot wait to be a dad. One thing that I am shitting myself about, losing an inch on the operating side when you have kids. I think you have to build it in before you're in the moment of having kids and having family responsibilities. We actually, as a company, have always had our first.
15:10 Speaker 02 Value be family first and what family first has meant is if you ever have a conflict, if you ever have a tie between your family and Olo, your family wins the tie every single time, no questions asked. No one has abused that over the years, but it is something that has unified us and has brought together people, obviously myself included, that really do put a priority on family and being the best children that they can, being the best spouse they can, being the best parent that they can, et cetera, et cetera. That manifests in how we think about benefits as a company and making sure that we have a very generous benefits package. It also manifests in things like parental leave and something that when our son came into the world, I really wanted to model for the entire team.
15:53 Speaker 02 I did pretty well of taking the full 12 week paid parental leave off. Great that I was a Jedi master at delegation because in the early years that would have been really hard. But we really sort of built that family comes first value. And you are now emulating that by spending the time on yourself and on your family. And I always end all of our all hands meetings with, you know, please take care of yourself, your mental and physical health. Take care of the people that you love and then with whatever you have left, bring that energy to Olo. And I think that has served us really well.
16:25 Harry Stebbings? Can I ask on the CEO coach, how often do you see Patrick? What do you think makes a great CEO coach in your relationship with him?
16:32 Speaker 02 I see Patrick once a week and it is a very high priority meeting that I do not like to move. Sometimes I have to move for one reason or another, but it's almost always once a week for an hour. And I think what makes him great is he has his toolkit and he's teaching me the different tools that he has used and he's taught others to use. But every meeting starts with, is there anything that's top of mind that you need to talk about right now? I love the Eisenhower matrix as a way of thinking and understanding a low urgency and high urgency, low importance and high importance and understanding that so many people conflate things that are important and things that are urgent and they believe that the urgent things are the things they have to spend their time on and they forego spending time on the important things.
17:17 Speaker 02 Patrick asking that question of anything that's top of mind. Is a real gift because every time it sort of takes all these urgent things that are swimming around in my brain and we deal with them and then we're able to focus on the important things after that. That's amazing because most meetings you're thinking about something else and it's distracting and you're not really bringing your best focused self to the discussion at hand, the debate at hand, unless you've cleared that. And I think clearing that is so important and I really appreciate that he does that every time that we get together.
17:46 Harry Stebbings? I want to dig in on the urgent versus important. Is everything urgent not important? I can see that important things aren't always urgent, but isn't everything that's urgent important?
17:55 Speaker 02 There are a ton of things that feel urgent in the moment, but no importance whatsoever on your business and can be snoozed or delegated or just ignored because they're not truly urgent, they just feel urgent. And I think the real problem is that we focus so much on blinking lights in front of us or the loud alarm bells that are ringing. That is sort of the false narrative and there's a very important thing that's underlying that, maybe a root cause that we miss because we're just dealing with these things that are right in our face and so recognizable, but aren't truly the long-term important things that we need to focus on.
18:31 Harry Stebbings? Do you not think also with the important things, things today that feel important, in five or 10 years, you'll barely remember them? Now, they feel very important today, but that hire for that new head of sales in APAC, it won't be that important in five years' time. So I guess, how do you feel about like the gravity of important decisions over time?
18:50 Speaker 02 Well, I think that is a good way of thinking about it. I would say that those things that seem really important right now, but won't be over a long time, those are really what I mean by the things that seem urgent. Like, I need to figure this out right now, but is it really going to matter five years, 10 years down the line? I would define that really as the urgent tasks or the urgent things versus the important things. But I think time horizons can be different depending on your role and depending on sort of what you're thinking about in terms of the future and the time scale. I do think, thinking clinically about separating those two things, another thing like this that I think about a lot is separating facts and
19:30 Speaker 02 Judgments from one another. So many times you'll get into a debate with somebody and they'll be very passionate about something. And you realize that what they are arguing is purely a set of judgments and not really rooted in fact. And being able to say, I think you're judging this differently than I'm judging this. The facts are this. Now let's look at this and think about it fresh from this set of facts, removing the judgment from the conversation. That is another very clarifying framework that I use. I love debate and discussion and I love ultimately changing my mind on things. But I need facts to do that. There's a great Michael Bloomberg quote of in God we trust, everyone else bring data. I love that quote because I think so many times I'm up against somebody who's disagreeing and it's not truly based on data.
20:15 Speaker 02 And I will demand, please show me the data that should make me change my mind on this. And that is a key way that you can argue against somebody who might be arguing very passionately, but without a lot of ground to stand on.
20:28 Harry Stebbings? Can I ask, do you not think some decisions are dataless, intuition led, you just feel it? Data cannot prove it, but I tell you, the customers will want this. I know the data doesn't say it because they tell me they want this. Go back to the Henry Ford customers want another horse. The data says they want fucking horses. They don't want a car. How do you think about those intuition gut led decisions?
20:50 Speaker 02 I absolutely believe that. In fact, I believe that the very origin story of Olo exactly that. If you'd asked a restaurant operator, what do you want? They would have said, I want a faster drive through. They wouldn't have said, I want on demand ordering so that the entire paradigm shifts. And the drive through is no longer the fastest way of getting food. So I absolutely do think that there is room for intuition. I really thought about this from the side of when I feel conviction in something. And when I have the tenacity to be holding on to that conviction and some might say that's stubbornness. I can change. I love changing my view on things, but if I'm dug in like that, the thing that will help me to change is not a different intuition.
21:32 Speaker 02 It's a fact that disproves something at the core that has led me to this belief. So I think that is a very important. Part of how I like to engage and debate with others and make decisions and also rethink decisions. I'm a big fan of the Jeff Bezos type one and type two decisions. There are some that are permanent and there are many, in fact, most that are reversible decisions. And I think entrepreneurship is really all about reevaluating small assumptions that you've made along the way, getting to truth so that you can steer in a better direction going forward.
22:04 Harry Stebbings? You mentioned listening to the Will Armad show from Whoop. I asked him, what does high performance mean to you? And you said that about kind of really the essence of entrepreneurship. If I were to ask you, what does high performance mean to you? How would you answer it?
22:16 Speaker 02 I think high performance, I'll come back to the equanimity idea, like being able to manage through the tasks at hand, whether those are very high level kind of strategic tasks or of more executional tasks. And to do it with a level head about you, with a sort of calmness about you, an openness to seeing things along the way that maybe change the direction that you're on. I think from my perspective and my role, how I think about high performance for founder, CEO of the company.
22:48 Harry Stebbings? Now, you said the word stubborn there. I spoke to your cap table and some were too scared to tell me a weakness and about half gave me a weakness. And everyone who gave me a weakness told me that you were incredibly stubborn. Would you agree that you are stubborn and it's a weakness? Or would you say it's a strength? And how do you feel about that?
23:06 Speaker 02 I agree with the old adage that every strength is also a weakness and every weakness is also a strength. I think the flip side of being super high conviction and having tenacity is that to the outside world, that can appear like stubbornness, like you're holding on to a bad hand for way too long. Many, many people have said that, many investors have said that throughout Olo's journey. I can't tell you how many pitches I've had where people say, look, I really like you. You're a great entrepreneur. Let's clear. Don't like this business that you're running. I don't think that this is the right thing. I don't think it's going to work. And I had to say, like, I disagree with that. I obviously like have poured all of myself into this because I have conviction that it will work. Like I said, I welcome debate. I think debate.
23:50 Speaker 02 Makes us better and I'd love having data and not just judgment masquerading as facts. When I'm faced with somebody with an opposing view, of course, if it's a compelling case that they make, if they erode the case that I've made, I'm willing to change my mind and I don't think that that's stubborn. I think I'm stubborn on the big vision and I'm very flexible on the details. And that's another Jeff Bezos quote that I particularly like.
24:14 Harry Stebbings? I'm sure you have a lot of founders come to you today asking for advice. How do you think about kind of when you reflect on your journey with Olo, some of the biggest piece of advice, given the reflections, it could be conserve cash, be very efficient. It could be around communications to board. But if you get to say, hey, these are the things I wish I'd known when I started.
24:33 Speaker 02 One of the things that we already talked about a bit, the separating oneself from the company advice. I really wish I'd known that or really had taken it to heart in the early days. It would have saved me a lot of personal pain. I can tell you that.
24:47 Harry Stebbings? Sorry, is it not harder today though for you because you have this continuous ticker on your company? Well, at least in private markets, you don't actually have like a live price now.
24:56 Speaker 02 Yeah, that's true. I guess that's right. I guess I don't put nearly as much weight in that because it's not something that I am in full control over. There are so many exogenous variables that impact a stock price. There is sort of what's happening in the market, what's happening in the world. I focus on the things that I can control and I do have a lot more separation today from the business than I did in the earliest days when it just felt so deeply personal and like I was strapped to the mast of this thing. I think on other advice, I'm really proud to be in addition to founder and CEO of Olo, a founder partner at Founder Collective and you've talked to David and sort of know about the philosophy that I know you share, Harry, around being scrappy and not taking on too much capital.
25:41 Speaker 02 I really subscribe to that. I think Olo is really a poster child for it. Having a net burn of just $6 million to get to 122 million in ARR at the time of our IPO. I really think that capital allocation and attention allocation are intertwined with one another. And it's so hard. To do one thing well and to be best in class at that thing, it's nearly impossible to do many things well. That is, by the way, why I eat at Pan Asian restaurants. I think you can only really be good at one cuisine, not every cuisine in an entire region of the globe. I think that sort of focus and attention and capital allocation to that focus helps a company to control its destiny.
26:21 Speaker 02 And that was vitally important to Olo over its history, to be scrappy and to get to profitability during this very thin, impossible-to-do fundraising time in the market. And then when the market really arrived and we got to true product-market fit, having the flexibility to then say, okay, let's go into scaling mode and bring in people who know how to scale what is special about this culture, up from the 12 people that have been working together for these first eight years into the company that we are today.
26:50 Harry Stebbings? I have one final question. I could talk to you all day now, but my final question to you is, how do you advise founders who say, I get you, don't raise and be more conservative, but if I don't raise, my competitors will, they'll outspend me, and so I have to raise? How do you advise them in that situation?
27:07 Speaker 02 I think that out-raising can be a blessing and it can be a curse. I do believe that there are some times when there is an opportunity that is truly a once-in-a-lifetime or once-in-a-world-history opportunity. That's what I came to believe about Olo's opportunity when we took on the funding from David Frankel. If I don't do this now, someone's going to do it, and this is the one time that it can be done. If I'm off of business school and I come to this years later, I'll be too late. Another form of that is not having the capital to really gobble up all of the demand that's out there at the right time. So I do think that that's legitimate in some cases, that you need to raise in order to capture all the opportunity and the opportunity in totality that's out there. I think far more often, people convince themselves of that, and they convince themselves that,
27:52 Speaker 02 oh, we won't be able to compete if we haven't raised as much as this competitor. And the curse part of raising too much money is you have to spend the money, you have to go and do things, and oftentimes that can breed a huge lack of focus, and that can mean that you're trying to do too many things at once, you're stretched too thin. And nothing that you're doing is really best in class. And you can have a very focused competitor who is doing one thing really well. They're able to win on that one thing and use that one thing as a wedge into the other things over time. And that's a big part of our story. We did have better funded competitors along the way who tried to do more than what we were doing. And we stayed very focused on being a best of breed application in digital ordering for enterprise restaurant brands.
28:37 Speaker 02 In the US market, a lot of no's in that, you know, not going global, not doing this outside of the restaurant space, not doing this with SMB, not doing loyalty programs and all singing, all dancing apps, but just digital ordering only, not being a consumer brand. There were a lot of no's in there, but that focus on what we were and what we want to be best to breed at and saying, and we're going to be an open platform with APIs on all sides, with a rich partner ecosystem to fill in those gaps with other best of breed players to truly meet the needs of our restaurant brands. That was the key to our success. It can be different scenarios, but I have loved our own experience of being incredibly focused and as a result incredibly capital and attention efficient.
29:20 Harry Stebbings? It reminds me of Frank Slutman's Narrow the Focus, Increase the Quality. I want to move into my favorite though now, which is a quick fire round. So I say a short statement and then you give me your immediate thoughts. Does that sound okay?
29:30 Speaker 02 Love it.
29:31 Harry Stebbings? Okay, so tell me, what's the favorite book and why?
29:33 Speaker 02 The Bible at Olo Remains Setting the Table by Danny Meyer, who is one of our investors and board members. And it preaches this idea of enlightened hospitality, which is about putting your team first, then your customers, then your partners, then your community, and only then your investors. Having your stakeholders in that order ultimately is the way to best serve all of your stakeholders. And it's something that we take to heart at Olo and value as a company that these are our values and something that we can tell honestly to all of the new team members that join us.
30:07 Harry Stebbings? What's been your biggest takeaway from working with Frankel?
30:09 Speaker 02 Honestly, my biggest takeaway is what an incredible father and husband human being that he is. He's known for being a great operator and entrepreneur. He's known for being a great investor. He's known for just being a business savant, but he is such a good human being. He is a true mensch. He's someone that is a mentor for me in business, obviously, and in my own entrepreneurial journey. But he is a mentor for me as a human being.
30:34 Harry Stebbings? I love that. No, I totally agree with you. Such a wonderful guy. Tell me, what's the most challenging element of your role with Olo today?
30:41 Speaker 02 The most challenging role is probably delegating things, realizing when we need to bring someone into the organization who will take the lead of some new initiative or some new components of the company and not being caught in a, oh, I can do that. Or so and so can do that and make it their part-time job. We're big believers in single-threaded leadership and having the right person responsible and accountable and assembling the right people on the team and making sure that everybody is single-threaded in the right way and has autonomy and has the ability to execute is the hardest part.
31:14 Harry Stebbings? Tell me, what would you like to change about the world of startups?
31:17 Speaker 02 I'd like to see more companies that can honestly say, we're doing well and we're doing good in parallel. I think there's still a lot of vanity metrics out there and I'd love to see really kind of enlightened entrepreneurship, people who are going after big ideas and world-changing ideas that are going to make the world a better place for our kids. And I wish that everybody in the ecosystem celebrated those stories and not just sort of the flashy, salacious detail kind of stories that you see a lot of the time.
31:47 Harry Stebbings? What's your biggest weakness and what are you doing to change it?
31:50 Speaker 02 My biggest weakness-
31:51 Harry Stebbings? And would your wife agree with you on it?
31:54 Speaker 02 I am the youngest of three kids, so my biggest weakness is almost definitionally conflict avoidance. I think I've gotten better at realizing that and being able to call it out when there is a conflict and then take action. My wife is the younger of two, so I think we're very similar in that way and she would probably call me out for it, but would recognize it because she experiences the same.
32:17 Harry Stebbings? You can have a billboard anywhere. Where would you have it and what would it say on it?
32:21 Speaker 02 I was thinking about where Olo's marketing dollars go and where all those marketing dollars and PR dollars go is really not in anything consumer or in anything kind of tech press. It's really focused on restaurant buyers. And so the newest thing that I would promote if I had a billboard is our newest innovation. That's a product called Olo Pay and the billboard would say- One-click checkout for 85 million consumers across 79,000 restaurants. That's something that I'm really excited about. It is us creating this two-sided network between all of our restaurant customers and all of the consumers that use our platform to bring a win-win experience to the table on behalf of everybody, and that's what I would use for my billboard.
33:04 Harry Stebbings? Next 10 years for you and Olo, if we do this in, god, 2032, where does the world look like and where are you then?
33:11 Speaker 02 So we are driving toward what I call digital entirety, which is every restaurant transaction being digital. And I think what that will unlock is something that I call digital hospitality, where a restaurant brand will be able to serve you better, provide a higher hospitality experience because of all the data that they have about you and because of all the data they have about other guests like you. I think that Olo itself has 100x growth and then some opportunity ahead of us, more restaurant locations, more orders per location as we get to digital entirety, and then more revenue per order from Olo Pay and other products that we can sell into our customer base. I think ultimately what this means for consumers, I envision a world in which you walk into
33:53 Speaker 02 a restaurant for the first time, it's the server's first week on the job, and yet you get treated like you've been a two-decade regular at that restaurant. So the vision that every guest is now a regular is something that we're talking about internally and getting excited about as the manifestation of this digital entirety, digital hospitality vision.
34:13 Harry Stebbings? Man, I absolutely love that every guest being a regular, and I think that's such a good caption. I would almost have that on my billboard.
34:20 Speaker 02 I like that.
34:21 Harry Stebbings? But no, this has been so much fun to do. As I said, I heard so many great things from Franklin in particular, but thank you so much for joining me today and for putting up with the wayward questions.
34:29 Speaker 02 Harry, thank you so much. It's an honor to join you.
34:34 Harry Stebbings? Just what an incredible operator. I couldn't be more excited for the times ahead with Olo. No, it was incredible on the show there. Huge thank you to him for giving up the time. But before we leave you today, quantifying and predicting company growth can be a challenging task. With Core Signal's historical headcount dataset, investors can easily see the historical growth trends of more than 20 million companies worldwide. Enriched with in-depth company information, this dataset is ideal for getting the complete picture of any selected company, including its growth and location trends over time. Core Signal's historical headcount dataset includes continuously updated snapshots of headcount and social media follower trends dating back to 2018. With it, be sure to enhance your investment analysis and decisions with hard data.
35:17 Harry Stebbings? Go to coresignal.com/20vc and download a free ebook that explains the various benefits alternative data offers for VCs. Once again, that's coresignal.com/20vc. And to be even credible tools like Core Signal that, from websites and online stores to marketing tools and analysis, Squarespace is the all-in-one platform to build a beautiful online presence and run your business. There are three things for me that really stood out about Squarespace. First, mobile optimized websites. All websites are optimized for mobile in a way that content automatically just adjusts so beautifully, so your site looks great on any device. Pretty awesome. Second is the email campaigns. Squarespace makes it super easy to grow and engage your audience with Squarespace email campaigns. And finally, SEO tools.
36:01 Harry Stebbings? Squarespace takes the guesswork out of SEO, so you'll get found in search by more people more often. And if that wasn't good enough, go to squarespace.com/20vc for a free trial. And when you're ready to launch, use the offer code 20vc and you'll save 10% off your first purchase of a website or a domain name. And last but by no means least, the incredible team at Angel List. They've been a key partner for me in managing my investments. I love using the Angel List platform because it abstracts away all the complexity and operational burden of fund management. So whether you're running SPVs, a traditional venture fund like me, or even a rolling fund, Angel List has you covered. I'm also though super excited about their new product, Angel List Stack, which is purpose-built for founders. With Angel List Stack, you can create a fundraising-ready startup in just a few clicks.
36:44 Harry Stebbings? Angel List handles your companies in corporation, banking, cap table, and fundraising process, all in one single place. This allows founders to focus on building. If you're a founder, you can launch your company at stack.angelist.com/20vc. Whether you're a founder or thunder, you're in great hands with Angel List.
37:01 Speaker 02 As always, I so appreciate all your support and I can't wait to bring you an incredible set of episodes next week.
Previous 20 Sales: Zoom's Head of North America Sales on When To Hire a Head of Sales, Why You Should Hire a Head of Sales Before Sales Reps, The 3 Traits to Look for When Hiring Sales Reps & What Sales Leaders Can Do To Make Their Sales Team Feel Like They Are Wi Next 20VC: Scaling to $2BN AUM in 3 years, Fundraising Lessons and Tactics from 2,500 LP Meetings & What it Takes to Build a Firm That Stands the Test of Time with Harley Miller, Co-Founder and Managing Partner @ Left Lane Capital Page updated September 29, 2026 · transcript and summary are machine-generated
