10 Cheat Codes I Learned While Scaling to $400M with Yext and Roam Founder Howard Lerman

Please welcome to the stage Howard Lerman, founder at Rome. So bear with me as I walk you through a structure of specific ideas. Very tactical kind of things that seem unconventional, and they at least worked for me. Maybe they'll work for you, and I encourage you to at least try them. So with that, the very first Jedi Master, if you will, that I stole something from was John Lennon. Okay. And there's a lot of talk about how do you tell your story in a company? And telling a story is really important. You have to be a grandmaster storyteller to be a success. Let me ask you a question. How many of you are founders? By show of hands? Okay. We have a lot of founders in the audience. Y' all better become really good at telling your story over and over again to the point of exhaustion, where you lose your voice and you feel like a politician. But nailing the storytelling is absolutely one of the most important things you can do. And by the way, for me to just say that that's not good advice for you, because you already know that. Right? And the boring presentation would say, nail your storytelling. Okay, thanks. How do I do that? Let me explain one little trick I learned for how to do this, and here's it. I just caught this quote from John Lennon once, and it unlocks my mind. And I think it's apt to be quoting a Beatles thing here that obviously, because we're here in the UK what John did, and you see, it says, do live demos. I'll get there in a second. That's actually not the trick. That's not the first part of this trick. What John Lennon once said was when he would write a song, he would write the song, and he wouldn't write it down. Now, has anybody here ever tried to write a song like music, musically? Okay? Like, you write down your story and you come back to it later. He didn't do that. And he encouraged George Harrison and other people in the Beatles to not write their songs down. And I thought this was a fascinating thing. And he said, you. You will know it's a good song that you've written if, when you come back to it a day later, you still remember it. Now, think about how crazy that is. Because if you're a teenage person in the radio and you're listening, this was like in the 60s when the Beatles were around and you're listening to something, you're listening to a song. If for the first time you hear a song, like, you may remember it or may not remember it, but if the author can't remember the song they wrote, how could they possibly expect the audience to. And I just thought that was a brilliant insight. And so this is a long, meandering story, a way of saying, when you are crafting your story, I think you should memorize your lines. I think when you memorize, the mere act of memorization, being able to remember it later, forces you to craft a great story. Like a poem, like your iambic pent, like something, some sort of phraseology. The process of saying that same thing over and over again and almost getting into a rap like rhythm around it is actually a formulative process in storytelling and removing the words and saying them at certain beats and rhythms. I realize this is a little musical, will help people remember it. And by the way, that is how you're going to remember it too. And that's how you're going to craft it almost. So what I would say is the very first sort of cheat code I learned is memorize your lines. It's not that you need to be able to get up there and deliver something from memory. That's not the point. The point is the act of memorizing your lines is one of composition. And you will find yourself continuously editing as you do it and removing. And mainly it's subtraction. Mainly you're going to be subtracting words you don't need. Because I can almost assure you the story you have right now is too complicated. You need to be able to pitch your story or tell your story like a Beatles song and not from the White Album. We're talking the early stuff. You need to get up there. And she loves me. Okay. That's the first lesson I learned and I took it from John Lennon. And an extension of this lesson is to do the live demos. Live demos, I think are highly underrated. My whole career I've been doing live demos. And by the way, they're super risky. They're incredibly nerve wracking. You're practically every time you use your product in a live situation, it has nothing to do with the risk of your actual product. We all know this. A hundred percent of the risk is related to the WI fi not working or the AV being shit. And fortunately here the AV is awesome. Nick and Kate, thank you for that. I can hear myself clearly. Everything seems to be working so far. That's hard because when you plug a computer in, like you don't have the right dong, like everything goes wrong. But here's the thing, you've got to take that risk. You've got to take the risk to Do a live demo. And I didn't really want to put a picture of myself up here, but this is one picture that I did put up, which was, this was me in 2009. And by the way, this was before, like, you could transcribe something and prompt it like magic. This was pre anything working. And I got up in front of TechCrunch in 2009 and. And pitched a voice recognition product. And insanely, I did the demo in a live theater. And I got up there just like an environment like this, and there was like, a thousand people or whatever, and Marc Andreessen was here, and Marissa Meyer was there, and Paul Graham was on the stage. They were the judges. And I got up and I did a live phone call to a random auto repair shop and transcribed it. Now, I had no idea what was going to happen with the feedback and the AV, and the odds of failure were probably 1 in 4, 1 and 3. But what I've learned is that when you get up and you do a live demo, people understand that you're taking a huge risk. And it is so much better to do a live demo where, by the way, everyone in the audience is. Is with you on that risk. They're, like, on the edge of their seat. Like, when I was, like, making that phone call, and you can see how nervous I am. I'm like, on the phone, I'm calling a fucking auto repair shop in Minneapolis. Can I say that word here? Probably not in Minneapolis. Okay, I can say Minneapolis. I'm calling it auto repair shop in Minneapolis. And everyone, they're like, what is this crazy guy doing? And, like, here's the thing. It's like, they all knew that this could fail. They all knew. Like, there was a. So the minute that people know something could fail, it's like when you're watching a movie and someone could die. Like, you can't stop watching it. Like, you need to keep watching it. And so you keep watching it anyway. The point is that when you do a live demo, you bring your audience along with you, and the risk that you are taking, it's all related to environment, not product. And that risk is one that. That they're with you with, and they will discount and give you extra bonus points for doing that. I strongly recommend doing live demos that could break. And frankly, sometimes you should have it break, because people like it when stuff goes wrong. They do. You get sympathy points. You could get up there, and if I got. If I run up to the stage and tripped and fell down hard and broke my arm. Right here in front of you guys. You guys would be talking about that way longer than any gas bag stuff I have to spout out about up here. And people even tell me, hey, remember that time that crazy guy ran up on stuff? Especially if I had ran up and then just tripped and fell. That would be the only thing you remember from the conference, right? So maybe I should do that next time. Okay. Okay. This one is something that I've said for a long time and everyone used to get really mad at me about this. I think one on one meetings are terrible. I think all meetings are terrible. Okay? I think all meetings are terrible. I especially have it out for one on one meetings. And I, I remember in 2015 or 2014 I wrote a LinkedIn post that said it's time to end one on one meetings. And practically every proper HR person and every proper manager in the world seemed to have commented on this thing telling me what a terrible manager I was and how horrible it must be to work for me and how I was just ignoring basic management principles by not setting up a regular weekly meeting one on one for one hour with my staff. And gosh, Howard, how could you possibly not be hearing about employee concerns and what are you possibly doing to manage people? And then this guy starts talking about how he has a direct staff of 60 people and he never has one on one meetings and all of a sudden it's like accepted practice now. So I think the point is that it doesn't help to wear a black leather jacket if you're going to try to do this. You just have to start a trillion dollar company. Apparently a billion dollar company is not enough. All right, so why do I hate one on one meetings? First off, I can barely sit through them myself. Right? But the main thing is that they tend to evolve into if first off. Okay, let's talk about time. I also believe in the flat organization I used to have when I was running Yext probably technically 30 to 35 direct reports, but realistically everybody reported to me, if that makes any sense. Like I would just walk around and we just try to make stuff happen as fast as possible. Here's the thing, there's a lot of downsides to one on one meetings, but one of them is that that you end up if you have 30 direct reports and you schedule a one on one meeting with all 30 people once a week, all of a sudden all you do all week is 31 on 1 meetings. It's a terrible idea. It clogs your calendar up. Second people, if they need to talk to you. They queue up the stuff they need to talk to you about until the meeting. So if I have a meeting with Kyle, with Kevin on Thursday at 2 o', clock, let's say I need to meet him and he's got something really urgent to tell Howard, the CEO, guess what? Kevin is going to wait until Thursday at 2 o' clock to deliver the news or whatever, work it through. But I think we should just do it right now. People queue up all their items and it slows you down because people queue up the things that they need to talk to you about next. People tend to get inventive. What they do is they invent things to talk to you about that they just don't need to talk to you about. And I don't have a problem with therapy. I am pro therapy, but I am not a therapist. Okay. And they just tend to turn into therapy sessions. And you can sense that kind of happening. People walk in and all of a sudden this bad thing, they're like. They feel that it's a time to air their grievances. And frankly, we're trying to start a company here and take over the world. I don't really want to hear about why you weren't happy with what Sally said to you or whatever. It's just time to get shit done. Sorry. Get stuff done and move on. I just want to make sure they can't reuse the live stream or at least it gets some bleeps in here. So Jensen now today, famously has no one on one meetings. He barely has any meetings at all. You have to imagine that Nvidia feels like an amoeba, like an amorphous sort of, you know, blob of people just getting stuff done at warp speeds to be able to produce things and go faster and continue to excel, accelerate their speed, not clog things down and slow things down and do it. This is a trick that I was always using, but now that he has legitimized it, you should feel free. And I give you all permission to cancel your one on one meetings with your team. I promise you, if you do this, your calendar will be. This is the single most important thing that besides breaking my arm on the stage, this is the single most important thing that I hope you take away from this. Cancel your one on one meetings. Stop having them. By the way, that doesn't mean that if people don't need to talk to you about something that they shouldn't. Right? If you need to talk to me about something, come, let's do it. But don't wait till Tuesday. And let's not have some regular scheduled thing for you to be able to just sit there and do stuff. Gosh, we're only on number nine. I better move this along. Okay. Oh, this one's bad. Founders. Founders. I am such a jerk. I hold Sunday night executive meetings now. The room went silent when I said that. Do people here. Is Sunday like a sports day here? What's the vibe for Sunday sports? Drinking. Yeah, I see. Okay. Drinking. Here's the thing. When you are starting a company, every possible thing that could go wrong will go wrong, and then more things that you did not anticipate that will go wrong. One of the best hacks that I figured out was holding Sunday night executive meetings. And I see John and Grace sort of chatting here, and they understand that. For me, I always hated Sundays. Sunday is the worst day of the week for me because I'm constantly thinking about what we're working on, the mission, we're trying to do it. And Saturdays, there's always a flow of work on Saturday morning when you wake up Saturday morning and people are doing stuff. I actually always send up my board decks on Saturday morning before the board meeting. That is. I didn't write that in, but that is a tip you should do. The best time to send a board deck is Saturday morning the week before your board meeting. Because the VCs. Are there any VCs in the audience? Awesome. Okay. There's no VCs in the audience, so they don't do anything. Okay. So they're just, like, skiing or. I don't know what people do for fun, but, like, they're vacationing. They're in Aspen, they're in Zermatt. And they're all. I don't exactly. And, like, they're all, like, standing around, like, talking, and they like. Saturday is like, not a different day for them because they don't, like, Thursday is like Sunday to them. Okay. So when you send it Saturday morning, they're like, oh, I think we got one working here on a Saturday. But that's that usually they're probably like taking like a private jet back from Europe that day back to San Francisco. And if you catch them, then they'll read it Sunday night. It will. It will show up first. So Saturday is the best day to send your board deck. And I always do this, by the way, you do your board meeting probably a Wednesday or Thursdays, put them there, and then send it out the Saturday morning before. I'm totally lost here with what I'm Talking about just to say it. I have no idea what time it is, what time zone I'm in, but I do see Tim Cook here. So back to Tim Cook. So you send out your flow of work stuff on Saturdays, and then Sundays, Sunday nights we hold our exec meetings. And so for me, and what I always did was I do them. We start at 8pm and like by 8pm, 9pm Sunday night, people are ready for that next round of work. And by the way, this is not the ranking file, okay? I'm not saying that you need to ask all of your team to work Sunday night. What I'm saying is the fricking founders who are starting the company and trying to do something impossible and move a rock up a mountain ought to be available at 8pm Sunday night for an hour and a half to plan out the week and make that part of your routine. And I thought I was a total jerk until I heard Tim Cook does the same thing. Tim Cook holds his exec. And by the way, it doesn't have to be like a meeting with video. It can be a call. You do an audio call and you have a call Sunday night. And it just gets. Here's why. It gets you a whole cycle ahead. Because you guys figure out as a management group, your, Your founders, your management team, what you're going to do for the week. Then you can divide up on Monday and engineering can go after their priorities and marketing can go after their priorities. It saves you three hours. And you get a. You get ahead of. You get a whole thing ahead. By the way, if you think Tim Cook is a jerk for making you do Sunday night meetings, let me tell you, Sam Walton from Walmart used to make people come in on Saturday mornings and they would have a barn burner in Arkansas and there was a whole thing, and people would all come in Saturday mornings. And so just to get ahead, to get a full cycle ahead of the pricing and stuff, ahead of all the Walmarts, that Walmart could beat all the other competitors. So anyway, that was a great trick. I want to give you just a quick other trick now, okay? I'm now regretting putting a former Secretary of State up here from the United States in this European conference as a picture with an American flag behind it. But there is a point to this story, which is the gentleman with the glasses is Dan Daniello. He's the founder of the Carlyle Group. The gentleman with the American flag is James Baker, who is American Secretary of State, Carlyle Group, huge private equity firm. Turns out I grew up down the street from Dan. Daniela. He was my neighbor growing up randomly. And this is before he founded Carlyle. It was as he was founding Carlyle, he's. I was like, about 8 and he was in his mid-30s starting the company. And I watched this with a lot of curiosity, like, why is this? What are they doing? Why is this guy starting this company? How's it going to work? I thought it was, like the coolest thing ever. And then one day, after they became wildly successful, I was in college, and I was a sophomore in college, and I was. And he was super helpful to me. Asked him, how do you do this? Why are you doing this? And I noticed that they added James Baker, the former Secretary of State, to their board, as an advisor. And I just. It didn't make any sense to me. I was like, why would a private equity firm want to have a former United States Secretary of State as a advisor? It's not just about who you know. It's about. It's not just about what you're trying to do. It's about who you know. And he told me that James Baker is a phone call away from any. Anybody in the world. And so we can tap into that. And that, I think, stuck with me. And here's the thing. I. And let me just tie this back to SaaS for a second. I actually think a lot of the BDR SDR outbound model here is totally inverted. And when I was running yext, I used to get all the amount of gifts, like, crappy gifts that I got all the time. I had a junk pile and I went to Duke. So I'd have, like, all the BDRs would send me a Duke hat. And then the BDR would be like, hey, did you get the Duke hat I sent? Can I get a meeting with you? And I'd like, dude, I got like 46 Duke hats here, and they don't even fit. It's not a good hat. And by the way, I don't want a hat. And by the way, even if I take your hat, like, why would I? What does that have to do with your software? But I have a lot of empathy for BDRs and outbound. It's just. It's not a good model. And this bottom up kind of model, I think is backwards. And who. Who does have access to me and CEOs, it's top down, and it should be top down. And so that's what Carlisle did. And I was like, okay, I can do that too. And so when I started yext this is really going to make you laugh. I call it. We were starting up this vertical SaaS business. We were starting up a lead generation thing for gyms and for veterinarians. So I called the past president, the guy, the guy in the suit is the founder of ursa, which is the trade organization for gyms. And I called him and I made him advisor. And guess what? Rick Caro is a phone call away from any gym in America and got us into. And you might not know these brands, but Crunch and Equinox and Bally Fitness. And we had within six months 2000 gyms signed up and we're like, okay, this model really works. What am I going to do next? We wanted to sell it to veterinarians. So can you guess who the guy holding the dog is? He is the president of the American Veterinary Medical association and he's a phone call away. And by the way, veterinarians are not people. This guy. And by the way, I can't even begin to tell you how silly this is. This Guy's name is Dr. Little, which is a whole other story in itself. We signed up 3,000 vets. He's a phone call away. The point is this. Use your. Let me make this very concrete for you. Take your cap table and use it as a weapon and take all the stock options that you have to give out to folks. You probably set aside some percentage, I'm sure if you're venture backed or not. And think about who your target audience is. And instead of investing heavily in BDRs and SDRs and outbound to generate demand, use your stock options to bring on advisors who can make a fast introduction to the top people immediately and get you in. No BDR is gonna be able to get a meeting with the CEO of some place. Now maybe your target audience isn't CEOs. Even still, it's much easier for Rick Caro to call up the CEO of a gym and get you into the right place top down. They don't even when you're selling to people that are not the CEO but are a couple rungs over. When you come in through the CEO, the customer, the prospect doesn't even know what's going on behind the scenes. They might think that they have to buy. You want to come in as high as possible. And this just make this very tactical. Use your cap table, find advisors, give them stock. And let me give you some tip about this for a second. Very specific. Make the stock only vest over up to one year. Don't make it four years when you Hire employees. You make it. It's four years because most advisors lose their. You just use up all their connections in six months. So make it a year. They'll follow through, but give them some stock at Rome. My new company, we have 93amazing founders in our cap table. And I'm a phone call away, if you will, from any founder we want because it's our target audience. And so I put my practice where this was. And I learned this trick from Mr. Daniello, which I still call him Mr. Even though I don't know why, from the Carlyle Group. All right, so Teddy Roosevelt was the President of the United States. And this is a very specific tactic I stole from him as I'm very against one on one meetings. But as you grow your company, you need to keep in touch with what is going on around the world. And YEXT opened offices in London and in the Netherlands. We had offices in Japan and Beijing and from all over the world. And one time I noticed that Teddy Roosevelt, I read this book about him by Doris Kearns Goodwin, the Bully Pulpit, which is an amazing book. And he used to hold five minute meetings as President of the United States. And people would line up inside of his office. He'd have a secretary time it five minutes, and people would come in, they'd make their case, and he'd make a decision. And I was thinking to myself, wait a minute. If Teddy Roosevelt can make a decision of matters of national consequence for the United States in five minutes, I can certainly hold a five minute meeting about some trivial item at the company and just get it done. And so I strongly recommend you try this. Make your calendar available for five minute slots. Don't make them 30, don't make them 60, because when you make them 30, guess what happens? The whole thing fills up with you. I guarantee you the meeting will be 30 minutes. You know, if you make it five, the same amount will get done in five. People get right to the point. And what's shocking is when I used to hold these five minute meetings and you really have to put a clock there. And you don't have to necessarily. You can have an assistant put the clock there so you don't look like the. The clock nerd. Sorry, we have to end now. They just, you know, come on in five minutes, next meeting's here. Bang. What's hilarious is you get done in three minutes and then you sit there awkwardly for two minutes and you're like, whoa, that was good. We good? Yeah, we're good. Okay, cool. Next meeting. All right, so that's one I learned from Teddy. This is one of my favorite people in the world. He's Jim Steele. Does anybody know Jim or heard of Jim? Jim is the president of Salesforce. He was president of YEXT for a while. If you're ever having a bad day, just go meet with your customers and they will cheer you up. Get out there, get on a plane, go see them. Jim used to say, I've never had a bad day with customers. He told me that when Marc Benioff hired him to found the enterprise group at Salesforce that he, that Mark used to run around and say if he saw Jim in the office he'd be like, get out of here. Like, like, why are you here? I don't wanna see you. I want you on a plane. And so I have found that there's a direct correlation in the enterprise for the amount of time I see a rep in the office and how bad they are. And let me say this a different way. You will never see your best reps because where are they? They're with customers. Andrew Ross Sorkin from the New York Times used to say, there's no news in the building. Get outta here. Go find the news, go make the news. Go be with your customers. This is an obvious one, obvious one, which brings me to the next one here. This is a super tactical one. I never said this before, but one time Intuit thought about buying Yext. So this was 10, 12 years ago, way before we were public and we talked about it a little bit. There was this guy Brad who was running into it and there was Scott Cook who was the founder and visionary genius. And then there was like Bill. And Bill showed up and was like talking to a sports coach and he was like, let's go champ. And I was what? You know what? Why? What's the point of this? And then Eric Schmidt wrote the book Trillion Dollar Coach about Bill after he died. And here's a really tactical point here, which is I learned at YEXT that you have this position in your company. So founder, CEOs by show of hands. CEOs, okay. How many. Keep your hands up. If you're also the chairman, how many of you are the founder and CEO but not the chairman? Okay, that is the way. And let me explain why. And by the way, if you're a founder CEO and you are the chairman, I recommend this is a hack. And by the way, I did this at Rome. Give up the chairman title. Find someone who is amazing, that is that can open doors. Maybe they've been the CEO of a big company before maybe they're in your industry. Give up the chairman title. Make that person the chair of the board. The chair of the board has no power. It's purely ceremonial. It's just a title. They call the meeting to order. That's all they do. They call the meeting order. There's some organizational stuff that goes on and if you're a series A company or even earlier, here's a trick and by the way, since there's no VCs in the audience, I can give you a trick, a trick that, that, that gives you a little bit of advantage over a vc. If you are a series A company and your board construction is two founders and the vc, you've raised an A round. So maybe there's three people on your board but the VC has all the sort of preferential voting rights and all that kind of stuff and has to approve any financing. One thing you can do is if you were to find somebody that is just like a totally next stratosphere person and go to the VC and say, hey, I'd love you go and you find a Bill Campbell. You say, hey, Bill Campbell is interested in being in the board. What do you think? And if they're well known, the VC will almost invariably say that's awesome. This is a really positive signal. It's, you know, the fact that somebody like Bill Campbell is willing to join the board of this company means that there's something potentially awesome happening. So hell yeah, we're going to, we want to put Bill on the board and what you and as the chairman. And so here's something you've done. You've basically bought yourself an extra board seat because later on you now Bill's going to be likely is going to be in your corner and all of a sudden you have someone who is overpowered in your corner on the board as an extra seat. And it's also the chair and I can almost and the way they say it is, hey, somebody like Bill wants to be an independent and it's a no brainer to get someone like that on your board. So I did this at Yext and I did it at Rome and I put on and I put what I recommend you go for is a person who has been around to the other side and has gotten to a level or two kind of like more than where you have been. At Yexta I asked Mike Walrath to be the board chair early on and gave up the title. And at Rome when I founded the company I asked Brent Saunders who at the time was the CEO of Allergan Health, which is a $95 billion pharmaceutical company. And I had been through a $3 billion company with Yext, but I had never been to a $90 billion company like Brent had. And so Brent is the chairman. I gave up the title. It was a total no brainer to do that. Easy to get done. Okay, Every piece of advice in the world is going to say, hey founder, as you scale, you need to delegate. Do not delegate. Do not. Do not. Just repeat after me, do not delegate. Okay, here's the thing. You will have to delegate functions. So I'm going to give you the exact order of delegate of. This is your delegate function for the engineers in the room. Okay? Delegate things in this order. First delegate legal. That's easy. Then delegate accounting. Then hr. Then strategic finance. Then delegate operations. Then delegate demand. Gen Sales, Customer success, Engineering, storytelling. The second to last thing you should delegate is recruiting. And then never over your dead body. Over your dead body. Over your corpse. Delegate product market fit. You as a found and I'm speaking to the founders here, your job as a founder is always to completely own and dominate product market fit. You cannot hire someone to run product. You cannot hire someone to figure out product market fit with customers. You, only you. It is the, the single most important thing you do. Everything else is window dressing, naming a chairman, figuring out how to do Sunday night. Exactly. These are all little tactics. But the core essence of being, the meaning of being a founder is finding and holding and hugging product market fit and never letting it go. And that can be for your existing product line if you launch another product and another product. But never ever delegate product market fit. And the last one is this. Have fun. It is your company. Just remember that you're all, Nobody knows anything. Just remember that like you're all like out there walking around. Everyone's got this advice and you're all here to get advice from me. I don't know anything. Like nobody knows anything. We're all specks on this planet flying through the sky here for a blink of time. Okay? It's going to be over soon. But here's the thing. This is your opportunity at this moment in time to, to have a playhouse. It's your company. You can do things your way. I only can tell you the ways that worked for me. But if it doesn't hit with you, then don't do it. And if a board member or expert or VC has a playbook that works for them, but it doesn't feel right to you, don't do it. Do it your way. This company, your company I'm speaking to, the founders have to be an extension of what works with you, what works for you. And so it's your company. Founder is the only permanent title. Even if your company gets big and goes public and you step back and they bring in a new CEO, you're still the founder forever. It's your house. Construct it your way. Never let anybody tell you how to do it against your gut, because your gut, the whole thing has to come out of your gut. From product, market fit to everything. You can reinvent other things along the way. If you look at when Apple made the iPhone, they didn't just make a better phone, they reinvented the entire retail experience. You walk into an Apple Store, there's no checkout. That was the craziest thing ever. They didn't have to do that. They just. They made it their way. Tesla reinvented not just the car, but how you buy a car. Buying a car online, putting down a payment, getting this whole thing, it's just different. They did it their way. From soup to nuts. And so when you make your product, you can also reinvent the other parts of your business. In any construction you want. Go to market, you can make your way. Admin, you can make your way. You can make things. It's your. Here's a good metaphor. It's your chocolate factory, okay? You can build chocolate rivers. You can give out golden tickets. Do it your way. Soup to nuts. Don't be like, oh, I made my product my way, and now I'm going to follow the playbooks for exactly how to do sales and marketing. No, make the whole thing your creative canvas and fill it in for exactly how you want to do it.