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Howard Lerman
We have engineers that have tremendous egos. In fact, some of the best ones have huge egos and they're huge pains in the asses to work with. And the problem about these guys is that they're a huge pain in the ass and they can and they're right.
Interviewer
Today I'm very excited to welcome Howard Lerman, founder and former CEO of yext, which he took from an idea to a public company on the New York Stock Exchange, during which it traded at over a billion dollar valuation on the first day of trading. Howard shares his unique philosophy on cockroach resilience and startups, how founders can instill speed into their very company DNA, and why figuring out product market fit is the last thing a founder should delegate. Without further ado, here's my conversation with Howard. So Howard, you refer to yourself as a cockroach, which is a term coined by YC founder Paul Graham. Tell me what it means to be a cockroach. Context of startups it means that when.
Howard Lerman
You start a company, you have no idea what necessarily it's going to take or not. And you try to make something, you come up with a hypothesis for a problem you want to solve and you make it. And it may or may not work. It may or may not be the right problem. You may or may not have the right solution. A cockroach is the indefeatable sort of pest that over many, many millennia is still with us today. And so I think a lot of the surviving entrepreneurs are a little bit like cockroaches in that they are able to withstand external conditions and evolve in whatever market they see fit. And so some specific examples of that are just like pretty much when you come up with something, being flexible on the details while being stubborn on the vision and being able to sort of change whatever it is you want to change and evolve over time to make sure that you're not killed.
Interviewer
Tell me in the context of yext, how you were able to apply this cockroach, for lack of a better term, to building that business.
Howard Lerman
This was in 2006 by the way. So you got to go back 19 years. We, we were going to create a lead gen site for the health club industry that was modeled after Hotels.com a little bit like Class Pass, except way before that the very first thing I did was I realized this was going to be a two sided marketplace. We were going to need to have a bunch of gyms sign up. So I emailed the founder of the trade association for health clubs and his name is Rick Caro. He Was like in his 60s at the time. And he agreed to join us and make a lot of introductions to the New York fitnesses and the equinoxes and the crunch fitnesses of the world to help us build up the network. And then we were going to drive traffic to it and then people would book a free pass and get paid. And it turned out that this was not a bad business, but it was not an awesome business. And we got to about 2 million of revenue and then recognized that that was about as big as it could possibly be. It turned out that we realized we could apply the same idea to a different vertical. Then we took that and grew it to 20 million. And then, you know, we, we ended up coming up with a whole different concept later on. As long as you have infinite creativity and are willing to chase new things that, that are grounded in reality, then there's no problem, you know, continuing to evolve over time and surviving over the long run. Which is, I guess, the, the origin of the cockroach metaphor.
Interviewer
If you take a completely first principles look at it. A startup is a C corp that bundles together humans and some social relational capital and an actual capital going after a certain goal. So you could actually evolve that structure as the company evolves and as the.
Howard Lerman
Market evolves, you can evolve a lot of different things. And if you can install the willingness to evolve in the DNA of the company and the genes of the company, that's when the magic happens. And by the way, if you look at every great company over time, they never stand still. In fact, they typically have a founding CEO or somebody like that pushing the envelope. Obviously the famous ones like Apple and Microsoft and Google and Facebook. Look at how Mark Zuckerberg is pushing meta into AI and all these different things at the next rung down. You have Shopify, for example. Look at, I mean, Toby is personally coding constantly and pushing, pushing things forward. He is on the bleeding edge himself. He just announced, you know, that Shopify is going to become an AI first company. This is what it takes to sustain, sustainably build a company, not just for today and, you know, for something that works now, but for something that's going to work in the future going forward as well.
Interviewer
Are these founders actually instilling something in the very fabric of the company or is it more a lead from the front?
Howard Lerman
There are both flavors that exist. My bet is that when you look at the kind of people that Shopify has, we just were talking about them for a second, they probably attract a lot of engineers, given Toby being an engineer and still in the code all day, and that the AI first kind of stuff really speaks to them. Toby just retweeted a tweet that he put up the other day about, you know, trust people who make stuff. And I think we're probably going to be looking at a lot of, a lot of people that make stuff as the people that are, we're going to be listening to and inspired by going forward.
Interviewer
It's like the Elon, what have you produced this week? As applied to every single business, I.
Howard Lerman
Think he says, what do you get done this week? But you just evolved it to say, what did you produce this week? Which is a really important tweak, right? Because going from what did you get done? I mean, one of the things you can get done is scheduling a lot of meetings and having a lot of meetings and doing a lot of whatever that might be, things you think you got done, but it didn't produce anything. And so by focusing on production, that's clearly how companies are going to maximize output.
Interviewer
As CEO of Rome, your new startup, what tools do you have at your disposal that makes your employees want to evolve the business alongside you?
Howard Lerman
One of the cool things about running Roam is that we all live in our product every day, all day. The old, we're the ultimate connoisseurs of dog food. As a consequence of this, and I have, I've, I and my team are continuously sampling lots and lots of dog food. I like to, to, to lead by setting a really specific vision for the office of the future. And we say it's people and AIs working side by side to enable AI first companies and you know, and then, you know, the tools you have at your disposal. And again, these are not technical tools. These are, these are techniques or Jedi tricks. Like I, for example, give a founder mode update every night, literally every night. It usually happens at about 11pm because that's when I look at the final run of what's come through stripe for the day. And around 11pm I'll review the metrics of how many inbound new travels we got, how many demos were booked today. The most important job of a CEO, in addition to setting the vision and having the correct vision and making the right decisions, is then to make things go fast. And so I try to make sure that the company is operating at warp speed all the time. And back to my dog food analogy here. One of the neat things about Roam is that the office is always on and Office of the future is 24 7. AIs don't sleep and Neither will a lot of engineers that are working to ship code. And so I go into our virtual office at 9pm, at 10pm, there are people there at 11pm I'm able to engage people. My job is to make sure that I am never what is holding things up and then also that I am pushing people to go as fast as possible because there's an absolutely new standard of speed that we're witnessing kind of break out here in this new era of AI transformation. There's a renaissance happening that is going to leave a lot of companies in the dust if they don't kind of shape up pretty soon.
Interviewer
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Howard Lerman
I, I actually think that founders tend to over rotate on the non authoritarian side because all the advice out there from quote, smart experienced people on their board or advisors is to, you know, bring in the experts and let them do their job. And it turns out that that is a absolutely terrible advice and founders should try to control the details for as long as they possibly can. And I actually have a stack rank order by which I think founders should give up details by kind of function. I think the first thing they should give up should be, you know, legal. You have a lawyer, okay, like you don't need to understand like you know, case law to be able to run your business, you know, hr, you don't need to understand the HR laws in the Netherlands. You can let someone else think about those things and then you kind of get down the chain depending on exactly who you are, who you are. And the very last thing, the absolute last thing a founder should ever delegate is product market fit. The single most important determinant of the outcome of a company is how strong their product market fit is. That is how well the product that they've shaped and continue to shape because it's an evolving process, fits in the market and is being received in the market. And frankly, some companies have such strong product market fit that execution can't screw it up, that they succeed despite poor execution. Twitter has always been an example of that. They were not a greatly run company for a very long time and they just continued to succeed because people loved it. You know, if you look at like Google, Google was obviously very well run for a long time under Eric Schmidt. But like they frankly could have put anybody in there and I think the thing still would have exploded. Probably the, probably the case is true with a lot of companies. So a founder's job is to latch onto product market fit and make sure that whatever that the company is producing and putting out into the world has a very snug fit with a, a group, a market that, that loves it and all the other stuff like you know, sales and mark, all that stuff matters. But you can, you can give that up. You know, first, don't give up the product market fit with regard to, you know, controlling the details. Like I don't actually produce anything. I guess so that gives me an advantage in not being overly tyrannical. Like I don't control code and I don't design. Everything I do is a collaboration. But I'm the orchestrator of putting all the pieces together in a, in a symphony. That sounds good. And as the composer, it's my job to make sure that the violin plays well with the viola, playing well with the bass, playing well with the wood instruments, the whole thing, and that it's conducted properly. Founder mode is actually maybe a little bit of response to over rotation of companies delegating to professional managers. Professional managers can't do anything. In fact, that might not even be a job at some point going forward. Professional managers, it's like the famous example of course is what happens when Apple brings in John Scully. Just read Alex Karp's book the Technical Republic. Technological Republic. Many of our founding fathers who by the way were super young, like 20, 21, 22, they were scientists. Organizations tend to promote people that are like more on the lawyer side than the science side and who are capable of putting together and figuring out the secret statuses within meetings. And you know, this is whole elaborate, you know, bureaucracy.
Interviewer
You have a top Engineer, this mythical 10x engineer that comes to Rome. And part of what drives really top engineers is their autonomy, their ability to produce what they see as, as the right approach. How do you balance that with founder mode? And what are some best practices?
Howard Lerman
You call them S Tier. Like if you check out the Rome website, you'll see we hire s tier people 10x, 100x whatevers tier. In Japan, by the way, they have a grading system and you can get an A, a B. And many American students are surprised to learn that in very rare circumstances a Japanese teacher for something exceptional may award an S. S stands for shu, which means like extremely good in Japanese basically. And so this kind of S tier term took on a meaning within video games. Like S tier is like the best player in the game. And actually it turns out that in the Gen Z folks, a lot of folks use S tier to describe people who are in, know the best in the game at any sort of domain that they're playing in. We, we want to appeal to those kind of people. So we, we built out, we basically require at Rome to get hired or to have an interview that you submit your S tier achievements to us. And we look for S tier achievements like being a National Merit Scholar, winning a computer science competition, winning a math competition, placing in a math competition, these sorts of things. My goal is to not be the smartest person in the room. In fact my goal is to be the dumbest person in the room. And I surround myself with these incredible S tier individuals who are, who are way more capable than me, particularly at their respective domain. And so again I'm trying to kind of put the whole thing together. So if we bring in an engineer, engineer doesn't just get to make whatever they want. Like they don't. We're building a, an office of the future like powered by AI. Functionally there's, there's a clear thing that kind of you have to do how you implement it, the specific architecture that you put in to, you know, achieve the result, like how we implement that. There's a lot of kind of kicking around.
Interviewer
You mentioned the S or the S tier. If I was head of department of Education, I would actually institute an A plus and A plus plus grading system in order to codify within the schooling system this reward for excellence. When you can't get anything more than A, you default to doing just enough.
Howard Lerman
We don't reward the over the top exceptionalism quite enough. Who by the way, if you look at the history of the world are the people that tend to be moving civilization forward. You know, it's, it's the small number of few people who come up with the breakthroughs and the innovations that, that benefit everyone. Yet we're very focused on, you know, cutting you off at a, or whatever. You know, why, why would we do that?
Interviewer
You've managed quite a few of these 10x or 100x engineers at yext now at roam is part of what makes them so great. Their lack of ego is that essentially one of the features of a truly elite engineer. Thank you for listening. To join our community and to make sure you do not miss any future episodes, please click the follow button above to subscribe.
Howard Lerman
I think that's not really related. We have engineers that have tremendous egos. In fact, some of the best ones have huge egos and they're huge pains in the asses to work with. And the problem about these guys is that they're a huge pain in the ass. And they can. And they're right. They're. They're correct. And so I don't, I don't. Like, I'm okay with that. Like, I'm okay looking stupid. I'm okay looking dumb. You know that, by the way. Like, you know, when I talk to young, younger people that have joined our company that are like, you know, just graduating college and they school me on like, a demo and crush it where I couldn't have done it, like, I'm sort of looking at these people like, holy crap. Like, I have nothing to learn, nothing to teach you, like, and everything to learn from you. Like, you know, things I don't know. Ego is an independent dimension to talent. And part of, part of being a leader is, you know, knowing how to kind of put the right people together and let people cool off and heat up. But I, I have no issue whatsoever dealing with someone who has a huge ego when their, when their talent is also huge.
Interviewer
You mentioned these nightly 9pm founder updates and the sense of urgency. Is that something that you could instill in a person or organization? Or is that something that you have to hire for as an intrinsic trait of a top performer?
Howard Lerman
We look for people at Rome who are obsessed, who are able to get obsessed, who have a crazy streak and who want to be on a journey. And that when they wake up in the morning, the first thing they think about is the journey they are on. And then the last thing they think about that night is the journey they're on. That is the level of obsession. It's tough to teach that. So you have to kind of look for that. You can certainly nurture it, but if they don't have that right out of the gate, that crazy streak, it's tougher to. Tougher to find the right people. So we look for people who have a crazy streak that, that, that, that. And I think the right word is obsession.
Interviewer
And that obsession, that crazy streak, that's an. Mostly an individual trait or is that they love the mission so much they. They go into obsessive.
Howard Lerman
It can be either. I think you can have just crazy ability in general. The thing that tends to bring it out of people more than the mission itself is the people they're surrounded by. And if you're, if you're born with obsessive, crazy, if, if you're born with the ability to get obsessive about something, and I think most people are, by the way, depending on what it is, if you're born with the ability to get obsessive about something, it doesn't mean that you will get obsessive at work. It has to be the correct conditions for it to come out of you. So we try to find the people who are obsessive and then create the circumstances by which they will become obsessed. The dirty trick here is that it's really not about the content of the company so much as the people. And the people around you are the ones that you never want to let down. And when you get on a journey and you feel like you're at war together, that is the kind of mentality that brings folks together in a super awesome way.
Interviewer
The culture itself is a product. It's a product that's consumed by the entire company. How do you know that someone might have that obsession in them? Through the interview process and how you recruit?
Howard Lerman
It's hard. You can kind of tell from how they talk about things they have done and the level of detail at which they talk and then how fast they talk about it or if their eyes begin to light up. I like to, you know, talk to people that have. By the way, it doesn't have to be like, oh, you know, I was working at Facebook and it was so exciting because xyz. In fact, if you're working for Facebook, you may not be obsessive at all. Just unless you were there in your very early stages. It's almost, almost a disqualifier right out of the gate. Unless you're like a, like a senior researcher in a specific area. The thing that I like to see are people, people who have been obsessed with something in the past and have a, have a, have. Have a, a bit of an involuntary response to you asking them about it. And then they can just keep talking about it and talking about it and talking about it and the more. And they can talk about it at different levels of detail. That's the other key thing. And they can talk about the big picture of kind of the idea of it, but then also get into the Weeds get into the very specific things that make that, make you know, that, that showed that they were really, really, really deep diving into the, into this subject or project or dance competition that they were trying to win. And by the way, it can be getting obsessed with a dance competition or it could be getting obsessed with playing an instrument. It could be any of those things. They're all s tier types of achievements that we, we look for and you have to be a little bit crazy to, to invest that extra time into winning.
Interviewer
Something reminds me of a book, the Hypomanic edge, written by Dr. Gartner about two decades ago, which delves into this advantage that some entrepreneurs have where they get really elevated, really excited, almost manic, not clinically, but slightly in order to become an entrepreneur. So there's this like edge case of people almost being manic and wanting to drive a vision forward.
Howard Lerman
I'm certainly not a psychiatrist, so I can't speak to what actually is or is not clinically manic, but I would not be surprised if I would be categorized as occasionally manic.
Interviewer
So taking a step back, tell me about your high school experience and how that formed you as an entrepreneur.
Howard Lerman
I was very lucky in that I was not only born in America, I was born in, in Northern Virginia where there was an exceptional high school and it still is called Thomas Jefferson High School for Science and Technology. And you know, growing up I was sort of a weird kid. I, I played baseball, I sang opera at the same time. And you know, you can imagine what kids would say when your mom, kids at baseball practice would say when your mom would, you know, pick you up to take you to, to opera practice. It was not the coolest thing possible as a, as a, as a nine year old boy, but I think it really taught me to, to deal with being made fun of, being teased, being rejected. I'm very good at that kind of thing because I just really don't care. And, and I grew thick skin from being on stage, you know, as a child, being thrown into the opera, singing opera, you know, on the stage at the Kennedy center at 9, 10, 11 years old in front of 2,000 fancy people every night, because I was not a fancy person. I'm not, I mean, lower middle class dude on stage singing opera in front of fancy people. You get to, you know, you get comfortable on stage pretty fast. And so that was a really formulative thing for me. And then I was lucky enough to get into teaching a STEM high school where, you know, the only way you get in is if you get a Good score on the math test. You can't charm your way in, you can't essay your way in, you can't, there's no political influence, you can't buy your way in. You can't give $5 million and get in. It's just, you can take the test and then like that's how it's going to be. And they take the top 400 people and going there, you know, I, I, I met other people that were like me, that were, that were like a little different and in particular had like a love of science and math and technology and stem. So this is where, you know, the school had a supercomputer at the time. This was like 1995. Like so I met some people there and I met Tom Dixon and Sean McIsaac who I've been starting companies with for the last Now, I guess 20 plus years. They were, you know, at Yext and at Rome. I was very lucky to be able to meet folks in high school that were like minded and I was kind of able to just get started early.
Interviewer
You've told me about your superpower of being able to look stupid. How did you cultivate the superpower?
Howard Lerman
I'm reading a book right now called Improv and it's Written, it's a 1972 book written by a famous London improv troupe leader. This is like folks on stage. And you'll hear me coming back, this idea of a stage, because I think that's a recurring theme in my life. My favorite Shakespeare quote is all the world is a stage. And if you think about it like, you know, I'm on your stage right now when I'm at Rome. It turns out one of the room types we have is a theater because every company has all hands presentations. So we have this gorgeous theater with all these like little details like stereo effects with clapping and booing and hissing and all these different types of things that happen only in a real theater that we whispering to people next to you that we've tried to recreate in a virtual environment in an AI type of theater. And being on stage, like you can't hide anything. You just kind of get used to having a hard shell about looking dumb.
Interviewer
I've been really interested in this concept of mimetics, mimetic copying, how ideas are transferred within society. I think Elon has really mastered this. He went past using words and he realized that memes are harder to, they're harder to block out of the subconscious and they, they're easier to share and lower risk to share. And all these things that make this kind of memes and memetic behavior really powerful.
Howard Lerman
That just really gets to David Deutsch's book, right the Beginning of Infinity. All species are capable of transmitting information one way, which is through their genes. But we as human beings and thinking machines have a different way that we can transport information amongst each other, which is through memes. And memes are empirical. They have to be self experienced. And all knowledge is empirical, has to be self taught. But the idea that you can kind of create higher chunks of ideas, I think is really important, that there's so many things going back to the kids of today, if you will. This idea of these Gen Z younger people that I myself am learning from instead of the other way around. What's happened is so many of the concepts that I had to learn over time have now been memeified. So what that has done is it has increased the speed at which people can get really good at something kind of just with higher order chunks. Specific example of that is this idea of product market fit. You and I both know what that means now, but when I was 20 and I started my first company, I had the concept did not exist. The concept may exist, but the meme did not. And so you had to kind of find your way to product market fit or grow, growth, marketing, or all these things that now you can write a textbook about. Someone can read it and start from a jump, you know, begin from a jumpstart of, of these higher order ideas which, you know, are transmitted through memes in our brains. And what's funny about memes is the way that they evolve too. Just like genes evolve accidentally and through mutation. And the better ones are selected, the same exact thing happens for memes. I'll give you a very specific example of Rome. When we started roaming, I branded it as the Office of Tomorrow. And I'd tell people, Office of Tomorrow. And everyone would come back to me or I'd hear them saying someone else, oh, that's how, or he's making the Office of the Future. And so it was the same idea of the meme, but I was witnessing it live, being modified. And the surviving version was not the Office of Tomorrow, it was the Office of the Future. Recognizing that this was happening, I actually changed it to the Office of the Future because I knew that that was a more powerful meme and that it would actually drown out the Office of Tomorrow. And so that's an example of, you know, you can almost think of a gene, a better version, a more adapted version, a Set of genes basically beating a crappier version because it just landed with people there.
Interviewer
The reason why I think a lot of businesses compound and improve is that founders and people at the company are able to kind of spot the evolution of certain things and incorporate into the business how you phrase something. You kind of just observe how people are using your product and you're like, what did you do? You like, put this and you emailed it to your grandma and your grandma went on her iPad and clicked a button like, let's codify that and let's turn that into a product. And I think that's why there's such a value to being able to the duration of your business and being able to survive, because the longer you survive, the more these things start to compound.
Howard Lerman
It's a really great example, and I'll give you an example at Rome. I mean, right now we are witnessing this moment in AI and you could say, oh, it started a couple years ago. The fact is that the AI technology that's out there is now good enough to do a lot of the things that people have been talking about doing for decades and was never before, possibly. And we sit at this unique point in time where, where the things that are possible and the adoption has not caught up yet. And that gap is the opportunity for many entrepreneurs right now to seize the moment and be able to bring these new capabilities and superpowers to businesses around the world. Let's take businesses out there, tens of millions of businesses out there that are either going to basically become AI first or be disrupted by a company that that is AI first. That's the only choice. We've been lucky with timing, but been able to build in so many incredible AI features into our. Into our platform in the office of the future, starting with Magic Minutes or AI note taking, building agentic workflows off of the AI note taker so that after a meeting's over, you can see what are the action items and then also give some of those action items to AI agents. So, you know, I think a professional manager may not have jumped on these opportunities in the same way or been able to evolve things as fast.
Interviewer
You mentioned agentic workflows, AI agents. Oftentimes talking to AI agents, this is a little bit difficult to grasp. Walk me through what AI agents are and how they're being used early on in the early use cases and how you see that evolving.
Howard Lerman
There are different definitions of agents. Some people might say agents, a single entity. Other people are spinning up pools of agents to do things at the Same time, and then wrapping that up into a higher entity called an AI worker. I would just say that all these definitions are kind of in flux right now and are going to evolve over time. But what is clear is that there are specific actionable things that drive incredible amounts of productivity and speed and cost reduction and accuracy that has never before been seen. I'll give you a couple of really specific examples. Examples say that an agent is capable of examining the text of a meeting and deciding who's going to do what after the meeting and assigning those things to you. So David is going to follow up with Sally and Sally is going to write the report on this feature and Joe is going to file the JIRA ticket. Some of those things now can actually be handled by an agent. So an agent can look at. Oh, Sally was supposed to schedule a meeting with Frank. I have a skill where I am able to examine calendars and schedule meetings. And so an agent can jump in and do that. An agent can jump in and answer, you know, follow up with people. It can make sure David sends the creative assets to Sean so that the correct thing can happen. We've already seen success with agents in customer support, answering customer questions based off of knowledge feedback. These are the kinds of things that, like, are not. They're now possible and they're all happening in the real world, yet most companies have not adopted them yet. And that's why we've seen in the past few weeks a number of companies, starting with Shopify. Then just last week I saw Box. Then I just also saw Spotify. And then I also saw Duolingo, announced that they are now AI first companies, which means that, you know, and each of them has slightly different interpretation, but they're basically not like they say, managers are not allowed to hire people until they check to see if an AI can do the job first.
Interviewer
Howard. I only got to about half my questions. We're going to have to do this again soon. Where could people follow you and where could people keep up with Rome?
Howard Lerman
I'm pretty active on X. I like to post what I'm reading. So I'm at Howard on X. I was very lucky to have gotten that as an early user at Howard on X. And then Rome is also at Rome. And our website is RO am. You can check out the Office of the Future there and step in for, by the way, a live tour. You can literally just come in right now. And that is because we have all the presence and the live feeling of being in a real office together with.
Interviewer
AI coworkers Well, thank you Howard for jumping on. Look forward to sitting down soon. Thanks for listening to my conversation with Howard. If you enjoyed this conversation, please hit the like or subscribe button. This is a free way to support the channel and also helps build the audience and views we need to get the very best guests. Thank you for your support.
Podcast Summary: "How I Invest with David Weisburd" — Episode E164: How I Built a Billion Dollar Company by Failing Fast w/Howard Lerman
Release Date: May 16, 2025
In Episode E164 of "How I Invest with David Weisburd," host David Weisburd engages in a profound conversation with Howard Lerman, the visionary founder and former CEO of Yext. Howard shares his entrepreneurial journey, emphasizing resilience, speed, and the indispensable role of product-market fit. This comprehensive summary delves into the key discussions, insights, and conclusions drawn from their dialogue.
Defining the "Cockroach" Mentality
Howard introduces the concept of being a "cockroach," inspired by YC founder Paul Graham. This metaphor encapsulates entrepreneurs' ability to survive and thrive amidst unpredictable challenges.
Howard Lerman [01:00]: "A cockroach is the indefeatable sort of pest that over many, many millennia is still with us today. A lot of the surviving entrepreneurs are a little bit like cockroaches in that they are able to withstand external conditions and evolve in whatever market they see fit."
Application in Startups
Howard elaborates on how flexibility combined with a steadfast vision allows startups to pivot and adapt without losing their core objectives.
Howard Lerman [02:04]: "As long as you have infinite creativity and are willing to chase new things that are grounded in reality, then there's no problem continuing to evolve over time and surviving over the long run."
Early Beginnings and Adaptation
Howard recounts the inception of Yext in 2006, initially targeting the health club industry with a lead generation model inspired by Hotels.com. Recognizing the limitations of this approach, he pivoted to different verticals, scaling the company from $2 million to $20 million in revenue.
Howard Lerman [02:04]: "We realized we could apply the same idea to a different vertical. Then we took that and grew it to 20 million. As long as you have infinite creativity and are willing to chase new things that are grounded in reality..."
Evolving Business Models
This adaptability was pivotal in Yext's growth, demonstrating the "cockroach" resilience by evolving the business model to better fit market demands.
Balancing Control and Autonomy
Howard discusses the delicate balance between instilling a company's DNA with adaptability and the founder's role in leading from the front.
Howard Lerman [04:56]: "If you can install the willingness to evolve in the DNA of the company and the genes of the company, that's when the magic happens."
Prioritizing Product-Market Fit
He emphasizes that product-market fit should remain under the founder's purview, as it is the cornerstone of a company's success.
Howard Lerman [09:08]: "The very last thing a founder should ever delegate is product market fit. The single most important determinant of the outcome of a company is how strong their product market fit is."
Orchestrating Collaboration
Howard likens his role to that of a conductor, ensuring all parts of the company work harmoniously towards a unified vision.
Howard Lerman [09:08]: "I'm the orchestrator of putting all the pieces together in a symphony. Founder mode is actually maybe a little bit of response to over rotation of companies delegating to professional managers."
Defining S-Tier Excellence
At Rome, Howard prioritizes recruiting "S-tier" individuals—those who exhibit exceptional talent and accomplishments.
Howard Lerman [13:21]: "We hire S tier people 10x, 100x whatever tier. We look for S tier achievements like being a National Merit Scholar, winning a computer science competition..."
Fostering a Collaborative Environment
By surrounding himself with highly capable individuals, Howard ensures that his role remains as the team’s orchestrator rather than the sole decision-maker.
Howard Lerman [15:03]: "My goal is to not be the smartest person in the room. In fact, my goal is to be the dumbest person in the room. I surround myself with these incredible S tier individuals..."
Hiring for Obsession
Howard underscores the importance of hiring individuals with an intrinsic obsession or a "crazy streak" that drives their dedication.
Howard Lerman [17:26]: "We look for people at Rome who are obsessed, who are able to get obsessed, who have a crazy streak and who want to be on a journey."
Building a Supportive Environment
He believes that the right company culture emerges from the people within it and the shared journey they embark upon.
Howard Lerman [18:10]: "The people around you are the ones that you never want to let down. When you get on a journey and you feel like you're at war together, that is the kind of mentality that brings folks together in a super awesome way."
Interview Insights
During interviews, Howard gauges candidates' obsession through their passion and depth in discussing past projects or interests.
Howard Lerman [19:16]: "I like to see people who have been obsessed with something in the past and have a bit of an involuntary response to you asking them about it."
AI as a Transformative Force
Howard discusses how Rome leverages AI to redefine the workplace, branding it as the "Office of the Future."
Howard Lerman [23:38]: "We built out, we basically require at Rome to get hired or to have an interview that you submit your S tier achievements to us. ... Rome is also at Rome. And our website is RO am."
Implementing AI Agents
He explains the concept of AI agents—autonomous entities that handle actionable tasks to enhance productivity and efficiency.
Howard Lerman [30:16]: "An agent can look at, oh, Sally was supposed to schedule a meeting with Frank. I have a skill where I am able to examine calendars and schedule meetings. And so an agent can jump in and do that."
AI-Driven Productivity
Howard highlights specific AI integrations, such as AI note-taking ("Magic Minutes") and agentic workflows that automate post-meeting action items.
Howard Lerman [29:59]: "We have built in so many incredible AI features into our platform... Magic Minutes or AI note taking, building agentic workflows off of the AI note taker..."
Early Life and Education
Howard reflects on his formative years at Thomas Jefferson High School for Science and Technology, highlighting how diverse experiences like singing opera and playing baseball taught him resilience and comfort in the spotlight.
Howard Lerman [21:18]: "I played baseball, I sang opera at the same time... singing opera on stage at the Kennedy center... taught me to deal with being made fun of, being teased, being rejected."
Building Lasting Partnerships
His high school connections with future business partners like Tom Dixon and Sean McIsaac laid the groundwork for his entrepreneurial ventures.
Howard Lerman [21:18]: "I met Tom Dixon and Sean McIsaac who I've been starting companies with for the last... 20 plus years."
Memetic Transmission of Ideas
Howard draws parallels between genetic evolution and the spread of memes—ideas that propagate through society and influence business strategies.
Howard Lerman [25:24]: "Memes are empirical. They have to be self experienced. All knowledge is empirical, has to be self taught... Memes evolve just like genes, better versions survive."
Adapting Branding Through Memes
An example from Rome illustrates how Howard adapted the company's branding based on memetic feedback to resonate more effectively with the target audience.
Howard Lerman [27:52]: "I branded it as the Office of Tomorrow... changed it to the Office of the Future because I knew that that was a more powerful meme..."
Seizing the AI Moment
Howard emphasizes the unprecedented opportunity presented by current AI advancements, urging entrepreneurs to leverage these technologies to stay ahead.
Howard Lerman [28:30]: "We sit at this unique point in time where the things that are possible and the adoption has not caught up yet. That gap is the opportunity for many entrepreneurs right now to seize the moment..."
Vision for Rome
With features like AI agents and immersive virtual offices, Rome aims to redefine workplace efficiency and collaboration in the AI era.
Howard Lerman [32:29]: "Our website is RO am. You can check out the Office of the Future there and step in for, by the way, a live tour."
Howard Lerman's insights on resilience, strategic adaptability, and the integration of AI into business operations offer a compelling blueprint for modern entrepreneurs. His emphasis on maintaining control over product-market fit, hiring exceptional talent, and fostering an obsessive company culture underscores the keys to building and sustaining a billion-dollar enterprise. As AI continues to reshape the business landscape, Howard's forward-thinking approach positions Rome at the forefront of this transformation.
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This summary captures the essence of Howard Lerman's conversation on the podcast, highlighting his entrepreneurial philosophy, strategies for building and leading a company, and his vision for the future of work with AI.