YouSaid · the spoken record

Jonathan Lowenhar

lines on the record: 104
first: 2024-12-05
most recent: 2024-12-05
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“Yeah. So we actually think the CEO has three jobs. We agree with two that you said, but we think there's a third. One is make sure everyone knows where we're going. The second one, pick the right people for the team, third one, give those people the tools they need to win. And you can abstract from those what they all mean, but. Most founders are really bad at hiring They fall prey to all sorts of pretty common human biases The lazy ones, back to laissez-faire, think it's just gambling. Like, oh, cool. They worked at Meta and Salesforce already. So hire them. Just gambling. There was work done by and then codified in a beautiful book. I'm going to make sure I get the names right, Jeffrey Smart and Randy Street.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“To sell the company, it's one of the skills. We teach this to all of our founders, as well as hiring and management and planning. I don't care what the thing is. For every one of our founders, we audit them and say, here's what you're great at, here's what you're shitty at, and here's what you've never done before. Now, which of these do you want to work on next, given where the company is in its cycle?”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“A set of skills that I'm great at, and there are these things where I know if I'm really honest with myself, if I listen to the quiet voice, I'm soft at these things or I'm not good enough at these things, or I have some imposter syndrome about these things. And if I don't get better at them, danger. That's the one we work with And it's when they care that much about both the hard skill development and maybe the soft skill development in their path to become a great CEO.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“We meet two types of hounders. Founder One says, Fix this part of my business. Totally transactional. I want to raise the next round or I'm hiring people badly or my founders aren't getting along or I want to sell my company. I need to be honest, it's not interesting to us. That's not our work. Go find someone who is, and I don't mean this disparagingly, but like a screwdriver, like fixes one thing, fix one thing. Then we meet second type of founder. And that founder says Likely to themselves because it's the only safe audience, there's some gap between the CEOIM and the one my company needs me to be.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“You're looking for in that first conversation, and this is what we ask our CEOs to do is to ask questions like what do you care most about the next year? What's the mandate? What about for your department? What are the things that keep you up at night? What's the break? What's the thing that could actually kill everything? If you had a pre-mortem for the next year, those kind of open-ended questions, because one our CEO listening for is the fantasy. See if there's some intersection between what they care about and what we might be able to squint and say we do.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“Doing something really cool, so are we. You game just for a 30 minute chat because I don't know where it'll go, but I think it'll be fun. Keep it that informal. It's peer to peer. I'm not selling you anything You can draw a line to like some post that they had or some speech they gave, even better. But we found without fail, there would be math that would show up, one out of four, one out of five, or one out of six. Yeah, that sounds fun. Because a lot of those CEOs never talk to startups. And that's fascinating to them, especially when presented with the energy of. I just want to have a fun intellectual discussion.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“Small startup wants to meet the luminaries in a space and they have their PR agency set up a panel where they contact the CEOs of the potential buyers and say, we're putting together a panel of the world's foremost experts in X. We're going to put four people on the panel. And it's going to be you and famous person number two and famous person number three. And this fourth person. Is illuminary to us And it's our startup CEO. And suddenly you're at the table as a peer. It's a completely different conversation. Second one, and this is going to sound a little silly, but I am not exaggerating it works. You are a CEO founder and you have that title on LinkedIn. Amazing the responses we get. So we made this list and we just started to send connection requests to the CEOs or CPOs or CFOs on our target list and said something as simple as this.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“It could be for this particular example that was in my head, ERP companies could be a buyer, large banks could be a buyer, the big software companies like Microsoft could be a buyer. There were a few different categories. And we said, great, who are the companies within those categories that make sense? They're acquisitive. They have the balance sheet for it. There's a Corp dev department. So we know that they actually know what they're talking about here. Ideally, there's an existing relationship with core team or advisors or board members. Make a list. Now, how do we meet them in a way without selling them? So, one of the examples in the book, which I love.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“Ezra does this really well in the book. Again, it has to be not solicitous. So, one of our companies, we had maybe 20 months of capital left. The two co founders and our team were convinced this isn't a venture business. We thought it might be a venture business, not a venture business. It takes too long to do a deal that's not that interesting with each of our enterprise customers. It was disappointing, but at least we were honest about it. Okay, so who are we going to sell to? Let's go play this game. So we start with categories categories of buyers.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“In fact, I think more often than that is a negative signal until the very end of the dance. So instead, an enterprise selling where I'm pushing in Magic Box, I'm always trying to entice. I'm never ever trying to push. So instead, I might say things like, hey, I'm going to raise my next rounding Q1 because I've been intending to do this business independently. Now, all I really want to do is win I just want my product in his customers' hands as possible. Whether I do that on my own as I was planning in partnership with someone or under someone else's roof, honestly, I don't care. But I have a company to run. I'm going to go raise my next round in Q1. And if I do that, Probably too expensive for this deal to make sense anymore. And my board will want me to move on anyway. I'm enticing I'm never trying to push.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I think three things. One is there are a lot of moments in enterprise sales where we're trying to push for a compelling event. Don't work in seduction The playful metaphor that we'll often use is. You've been dating for a while Person could be the person, but they're not quite convinced yet that it should be a life together, and you're sitting at dinner Enterprise sales, you're eager to get it done. You're eager to move the relationship forward and move in and get engaged, what have you. And so you might be inclined to say. Hey, either we move this relationship the next step, or there are a whole bunch of people eye on me, and I'm going to go date someone else. That conversation never goes well. And in Magic Box, founders are eager to do the same thing, thinking that competition will improve their deal size.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“Most important things to understand is that they can be a leverage point to have a deal move with some process and some pace and some urgency because either deals have momentum or they die. And Corp Dev can help there. Second, they are way better at negotiating than you. So Anytime dealing with a superior negotiator, the only thing you can do to try and even the scales is move the negotiation async. So, founders repeat after me. I'm talking to you directly now. You will say to Korp Dev, you know I am not alone in this decision. Love what you just said, and I'm excited about this opportunity. Once I see it in writing, I can socialize it with advisors, lawyers, co-founders, whoever. But don't negotiate live, you will lose.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“One is the fantasy is beyond just what is the business change you can have. The fantasy is your books are Fantasy is all of your investors will sign off on the deal and you will have unanimous consent. That the key members of your team are going to stick around, that you're a joy to work with. Please God, founder, do not puncture the fantasy at any time. So, whatever is starting to shape in your buyer's mind, get to know it. Live that. Everybody wins from that game. Second, Corp Will probably show up in this dance Corp Dev make deals Are not deal sponsors. They are not a champion. They are not a buyer. Are an expert in negotiator. Their job is to facilitate deals and get deals done.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“A business sub 2 million in revenue, our prospects of raising Series B felt low. We were not yet profitable. And that was an exit that was generational wealth for the co-founders and their families. The CEO went on and spent two plus years with the now public company that did this acquisition. The technology did get integrated, but it took a long time and they had to do a lot of changes to it, certainly beyond what was envisioned during the diligence process. But all parties are happy. And if we hadn't done it this way and we had just been up for sale, Get a dollar for that company. A couple of other side points that are really important here for any of you founders out there that are thinking about working backwards from an exit, there are two things that I really want to stress.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“And the champion will tell you Retention does this or deal size goes like this or market share goes like this. And you'll say to them, fantastic, look, I'm going to build some shitty verse version of the model. Tell me what I got right, what I got wrong, but I have a board meeting in 16 days, and I need to be able to walk them through to justify why I'm spending so many calories on this exercise. Build the model, you hand it to them. They in any way respond to your model, you've won Because you have now divorced history from future. You are now playing in future. You are playing the Instagram game in this case. Ending of the story for the company that I was describing.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“We know we're already going to win the proof, and that's critically important in these dances. Number three, quantify. At this point, we're not up for sale. But we're spending a lot of calories on somebody. And they know it. So we have our CEO say the following phrase to them. Board's asking questions. They're wondering why we're spending so many calories on this when it's not really quarter we're not selling you our product. I am convinced of how exciting this could be together. But I think we need to do some math so I can explain to my board why this might matter. So let's imagine all this works because it's going to work. And it's a year from now or five years from now. Changes about your business”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“Because in almost all cases, big companies buying little company, and your champion doesn't have unilateral authority. Going to socialize the deal. They have to get buy-in from who? The aforementioned buyer. They have to be able to survive the aforementioned blockers. So Eventually, when they pitch this to whatever committee is in charge, That committee is going to say, What proof do we have that it works? And we just want to be able to provide the champion with enough evidence that it works. So, in this case, we said to the champion, well, give us video data. We will provide you the evidence that you need. But because we're dealing with a champion who's not a cynic, because champions aren't, we could tell them and provide us the data in this way, in this fashion. And here's what we'll send you after. Are we in agreement?”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“So, what happens is they've come up with a fantasy, and you as a CEO need to lean into it. This is an enterprise selling. I am not trying to sell you this thing that I have. I'm just trying to find ways to say yes. So, when in my story, the person says could we provide you all of our video data that we've collected forever and you now enhance our ability to predict whether large-scale construction projects are on time? I don't want the CEO saying anything other than we can do that. Now, phase two, I need to prove it. Okay Because I have a champion. Who wants to say yes? Proof can be really easy And the reason the proof is so important is not to convince the champion they're in love with the fantasy. They're already convinced.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“You have played chess. So advocates are pawns. Don't matter at all until they matter enormously. These are folks that you're the CEO doing a meeting with your potential buyer and there are somehow 12 people on the Zoom call, but only two do the talking. The other 10 might be advocates. They're rooting for you, but they will take no political risk. Their value is and give you intel. Is the person who can't say yes, but they can say no. This is Opsak. This is procurement. This is legal. Going to meet all these characters during the magic box dance. Your champion just wants you to get the deal done because they're so in love.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“There may be a fifth. You're going to meet your champion. You're going to meet your advocates. You're going to meet your blockers. And you're going to meet your buyer. You might meet Corp Dev along the way. Let me talk about each of those folks. The champion is one who's fallen in love. They're the ones with the fantasy. They're the ones who are arguing on your behalf. They're the ones fighting for you when you're not in the room. They are texting you. They're telling you things about the business that they're probably not supposed to tell you Buyer. All they care about is math. It might be a committee, it might be a group, the IC, the EC, the investment group, what have you. They're the ones who actually can sign off on a deal. They care about business case. Advocates Do you play chess”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“Is a person. And the reason I'm being specific about that is because you don't sell to a company Magic boxes about finding the person. You're finding the champion on the other side. The person who is motivated for their own reasons, career, money, reputation, what have you, they see the fantasy, they fall in love. And this person says, I'm in love with this idea. If I can grab security data into my product work. Now I have to prove the fantasy. What's different about a champion in this kind of process? Is they want to find a way to say yes. Not looking for a way to say no. And this brings us to the four characters you're going to meet along the path of Magic Box.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“And the business was doing pretty well. I helped the founders. We helped the founders launch the company. We got first product in market. We raised a couple of rounds of capital. The product mostly worked. We weren't sure it was venture scale as we were going along. And we had some large construction tech companies and real estate companies and development companies leaning into us. In one particular company then said Huh, we're really good at construction planning. And we've collected all of this video data that we don't use at all. The champion on the other side in the product org, he has a fantasy. Oh shit. We take your video analytics platform and plug it into what we do, and this is what happens to my business. The person on the other side.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“There was no math Facebook could use. Historically speaking, that would justify a billion dollars. It had to be a model on the future. Is Magic Box to a T. Had a fantasy that adding Instagram would expand ad revenue. Figured out some way to prove it. I'll explain more and what I mean by proof. And then their quantification was based on the future. And that's the difference between a magic box approach and traditional approaches. Traditional approaches are based on the past, magic boxes on the future. Let me tell a story. One of our companies in construction tech. Their technology was able to suck in video camera data from construction sites for project planning. No one was doing this yet.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“Generally speaking, another oversimplification here, large companies are interested in small companies because they're technology and small companies are interested in large companies because their distribution. And there's someone at the large company who becomes fascinated with you. What's the fascination What they see in their head is, oh, interesting. If I buy your company, this thing happens. Classic example of this is Instagram. This is the number one example of this. Do you remember how much revenue they had when they got acquired by now Meta?”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“And it's one that often will just hit the nervous system of any founder that's been through it a couple of times because, man, is it a fraught exercise? What Magic Box argues is that the best outcomes for early stage startups don't happen that way. You're never for sale. In fact, you have seduced a buyer. You have brought someone in. And there are three stages to magic box work. Is learn the fantasy There is prove the fantasy, and there's quantify the fantasy. All right, so what the hell do I mean by a fantasy? You're an early stage startup and you meet a company that is in your space, in your vertical, what have you, and they're much more advanced than you. It's a large business.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“Is a traditional sales process. You build a list of the companies that might want to acquire you. You figure out the categories of buyers, the companies there, the contact list within that, you ping them and say we're open to a transaction or some euphemism, the like. You contact them and say, I'll give you some information now, sign an NDA, give me an indication of interest by this date, and you work through a process and you pray you have more than one person at the end of the game. try and ratchet them up, sign a term sheet. They will then retrade along the way right up into the point you die and you hope you get a deal done.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“I can and I want to give credit where it's due. So there was a book by this name. It's called Magic Box Paradigm, written by an independent banker named Ezra Royzen. And the book's fantastic. And Ezra is fantastic. What we've done is we've operationalized it so that we could teach founders over and over and over again. If the founder wants to hire a banker for this particular process, because we're not bankers, we're not BD. We don't get paid that way. We're teachers. But if they wanted to hire a banker, go hire Ezra. The methodology itself? Is a inversion for how venture and venture boards have thought about startups being ready for sale for a long, long time. It's utterly counter to so much advice that founders have heard. There are Two ways you can get acquired. This is purposely reductive. One is you put up a for sale sign.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“I now no longer have to just guess all the time. And this only works for the CEO who says Improvisational efforts got me here. But I don't think they'll get me there. There's a guy I worked for a long time ago, and he had this phrase. He had like seven or eight phrases. He would use him over and over and over again. It was hard not to commit them all to memory. And one of them was, if you keep doing what you're doing, you'll keep getting what you're getting. And for the ready fire aim folks who realize the weakness of that at scale. Way to counteract that is to start with good planning.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“That's a qualitative and quantitative answer, but we write it down Need to get better at go to market. We need to land our first partner. We need to launch next iteration of the product and show this level of efficacy engagement. What have you? Can we codify that? Yes Can we talk through what actions would be required on what cadence to unlock that quantified set of results? Yes. Do we understand what resources would be required to do those things? Recognize we might have to squint through some of it, but again, the answer is yes. We've now aimed If we have a culture that has some accountability, that has a communication architecture, so there's some rituals about how we meet and how we share information and how we talk through problems and how we work through bottlenecks. Now we have a plan. And now we have accountability.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“Basic, basic business design and business planning is not some corporate effort. It's some thoughtful exercise that starts with what are we working backwards from? Because at any given time, Lenny, companies are working backwards from one of four things, whether they like it or not. I am working backwards from an exit. I'm working backwards from my next fundraise, working backwards from profitability or I'm working backwards from winding down. We don't talk about the fourth one that much, but I got to choose one. I got to choose the top of the mountain. More often than not, they're choosing a fundraise. So then we'll ask that founder You know your market, you know your investors, you know the next set of investors we've done some intel what has to be true to unlock the next fundraise?”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“I think ready fire aim is the most common that we've seen. And that has been an affliction that's been growing in the last number of years. It wasn't long ago that CEOs could paper over poor execution with easy access to capital. And suddenly, over the last number of years, we're expecting founders to be better operators. Better operators means eventually being on a path where more cash comes into the business than out of the business. Don't happen by accident. The ready fire aim CEO has probably suffered this pain. They took lots and lots of bets. Maybe they measured the outcome after the fact, and they were wrong and they were wrong and they were wrong in ways that were expensive. And they raised their hand to say, I see it. I want to get better at this.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“That's right. I enjoyed giving this talk on stage and watching different founders in the audience cringe at different moments. But it doesn't mean that they're all one or the other. If they were all one of these and then didn't want to even accept the possibility that there's a little bit of a lot of these that they could work on, they're probably not coachable and they're not going to be in the talk anyway.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“Micromanager, CEO doesn't see the difference between those two humans. They don't trust anybody. And that's actually the thing under the thing under the thing. So they want to do everyone's work. And that will succeed right up into the point everyone quits.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“The challenge with this one is it is massively disrespectful to those who work for you. And we think that, and this is a bit insulting, that everyone that works for a founder can be fit into one or two chunks. They're either an adult or a child. I have a three year My little girl's amazing. I'm utterly in love. And if she doesn't have a lot of structure and a lot of supervision, she's going to run into things, man, into things off things through things. Adults don't need to be given utter instruction and watched all the time. In fact, it needs to be the opposite. We agree on what success is, what resources are, and you let them go. And they'll come back to you when they have questions.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“A little bit of bottoms up planning to say what are we trying to achieve? How do we quantify it? What resources are required? What humans are going to do what? How do we shorten feedback loops so we know in a week and a month and two months whether we're on the right trajectory? The Ready Fire AIM CEO says, I don't want to do any of that because they're improvisational and they just want to take bets and they want to take shots. And that's what got the company started. And that's also what have the company go bankrupt. The micromanager one is the opposite of laissez-faire. They believe that no matter how many employees they have, they can do the job better.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“Going to run out of money really fast. And this kind of connects to one of our other challenging CEO types, the Ready Fire Aim. Most CEOs are really bad at planning. And that's because there's this little-known secret in the Bay Area. Most CEOs have never run a business before. Planning doesn't have to be some heavy bureaucratic multi month exercise that begins in August and ends in February”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“So every CEO we can reductively reduce to one of two characters. They're either comfortable with the break or comfortable with the accelerator. The challenge with those who are comfortable with the break, what I mean by that is they don't want to spend any money. They're driving this beautiful sports car, and they're just leaning on the brake the whole time. So, yes, they won't run any money. And yes, they will also get lapped by everyone else and miss the opportunity. And so where their opportunity is, is where can you take bets? Where can you actually downshift that car in such a way where you give yourself a chance in the market? Separate those who ride the accelerator. We've all met this one.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“Point being, no one wants to work for the angry person. Don't care what the equity potential is worth. No one wants to work for that person. And the moment they see greener pastures elsewhere, they're leaving. The next one is the one that drives me particularly crazy. It's a laissez-faire CEO who insanely believes that I can just hire great people and utterly ignore them and let markets take care of themselves and they will do all the right things. I have never met anyone, Lenny, that didn't benefit from good management. Laissez-faire CEO believes that management is not required. And so, what they ultimately find is they have really, really good people doing utterly disconnected things and goals are not achieved.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“He said, okay. I said, I think you wake up in the morning angry and you don't know it. And then you get to the office and you beat the crap out of the first employee that crosses path with you over something utterly unrelated because you're angry. You realize that a few hours later, and you will apologize, and your team hasn't quit yet because they believe you're a good human who doesn't. Good self control And then I shared with them, and you just had your first child. My guess is, because I'm not a psychologist, I'm not a therapist. You are modeling something that's happened in your life. Is this something you want to change? Answer is yes. And I said, Great. I have good news and bad news. The good news is because you said yes, we can do something about it. And the bad news is, I don't know what the fuck can do. That's not my job.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“It creates two problems in a business. One is you're just slow. And the other one is you'll never take any bets. You will build a team that realizes the CEO is not allowed to be wrong, so you can't disagree. You can't use intuition, you can't use gut. Everything has to be utterly factual, and that is simply not possible. In early stage startups, you have more questions than you do answers. Everything is circumstantial. It's not like watching CSI entrepreneurship. And you get to see a video to say, oh, look, the guy did it. No, we have a bunch of little data points you have to come to a conclusion. The next one's the angry CEO. I had a founder of mine a bunch of years ago, and we were seeing a pattern across the leadership team. And he and I get in the phone one morning, and I said, I have a theory for you. Might be a story. I might be wrong, but I want to share.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“Then running a business. So they can't tell anyone hard news. They can't break ties. They want a consensus on everything. And that's not possible. If you have a group of thoughtful people working for you, they're going to fight. They're going to debate and you want them to. And then at some point, you have to call it and say, no, we're going left, not right. Where the two of you need to go get in a room and deal with something, or hey, the way you just showed up is not the way I want you to show up. The pleaser CEO won't do any of that. They will simply hide and pray it goes away and it won't go away. Next one's a perfectionist CEO. I like to say that these are the CEOs with the most beautiful product to be delivered minutes before they file for bankruptcy. This is the person who is far more concerned with being”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“I also a little bit more. Little bit more graceful of an answer there is also our CEOs want urgency and passion and excitement from their teams. They want them working enormously hard for below market comp more often than not with this promise of equity that might return value five or ten or twelve years later. They want them to bring all of that emotion, but they're supposed to figure out how to surgically cut off the emotions that are inconvenient. That's the robot CEO who believes that we can just have sterile robots working for us, and you just press a button and they do a thing. Second one's a pleaser CEO. This is the person who is far more concerned with being liked.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“It's grim, but also if the two or three people in charge of the business can't get along, nothing else matters. It's all going to break apart. And then, fourth, execution. An execution now leads back to CEO. Okay, so now we have a bunch of playful ones here. Have the robot CEO who believes emotion should not ever exist at a startup. Which point we train them on a very simple formula. Emotions are messy, humans have emotions, they are Startups need humans, therefore, startups are messy.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, we do take a bit of a comical approach to some of this. As I've shared with you previously, the name of our company is not an accident. If we can't be playful, we can take the work seriously and not ourselves. So we do fuck around quite a bit. I think. If I would separate failure modes for companies versus CEOs for a minute, the company ones are not quite as comedic, but they are ones we see all the time. One is you chose the wrong market. I don't think we need to belabor that one. Lots of your prior guests have talked about the importance of getting that part right or nothing else really matters. Second, back to what we were discussing a minute ago, build something people want to buy. Gotta go build the right thing. Cool. Third one, founder dysfunction. We like to joke that more companies die from suicide than homicide.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“And they can drop into a product feature, they can drop into a customer conversation, or a partner conversation, or with a longtime employee that's still in IC and be impactful and then rise back up if they've gone the training and get back into a cockpit to run the company again. And that's to me the distinction. It's not manager mode is bad. It's the greatest CEOs know when to calibrate which one is needed.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“The idea that the founder who's writing code by themselves doesn't have to advance their skills to learn how to do all those things. And that, in fact, what the article even implies is learning how to do those other things is a negative Bananas to The things required to launch a company are not the same as grow a company, as scale a company, as exit a company. And the best startup CEOs learn them all along the way. There are lots of ways to learn them. I'm not suggesting there's only one path But Founder Mobe is almost an excuse not to. I do think what's unique about a founder that felt perhaps where that article was trying to go Is that unlike the professional mercenary CEO that gets dropped in? The founder knows everything about what built this company, and they can drop in at the most granular level. Play anywhere”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yes, founder mode gets me angry. That article just got me hot. Really felt like an excuse. We were giving founders a permission. Not learn the job. We think about an ascending startup, there's this phase of I have to invent something. I now have to figure out how to get my customer in front of this invention and see if it works. Then I have to build a business model around that to see if there's some repeatable way to attract, win, deploy my customer, and thrill them with whatever the solution is. Now I have to go build an enormous amount of demand. And then I have to build up an operation that can handle all that demand. Oh, and by the way, at some point, figure out how to turn positive revenues into positive cash flows.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“How can that possibly be true Instead, Describes skills This is a person who has to build stuff and sell stuff and recruit people and raise capital and organize humans and financially plan Question number three, my final one. Well, how does a founder learn those skills while doing the job? And I got blank fucking stares. Over and over again So it led me down this path that I'm now 10 years into with my colleagues of, well, how do we help founders learn those skills so that their venture investors don't fire them? That they can actually go build whatever company they want to build and stay in the job for as long as they want to stay in the job. So that's origin. That's what got me going”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“So I started to obsess about this question And what it led me to realize is that every well-run company has a rhythm. It's unmistakable. You can't miss it. You can't not see it. You just spend a couple of days, like through a spy cam watching a business, you'll see the pattern. So, how come some startups get there and some don't? How does a founder learn the rhythm? How do they learn how to run a company well? So I started to ask investors. Kind of obsessively. And I ask them all three questions. Same three over and over and over again. First question was well, describe to me your ideal founder. What's a great founder The answer is universally were the same. Investors would use words that meant grit and tenacity and courage and insight. I say, great question number two, describe to me a great startup CEO. And they use none of those words.”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source
“I had run a bunch of different types of companies, and they were really different ones. So I ran a big division for a public company that I was a private equity CEO, then I did back-to-back startups. And the first one didn't get very far, but we sold it, and the second one got really far. And when I left the second one, I was like many founders grossly unhealthy. 25 pounds overweight slept wasn't sleeping enough all the things and it took a few months to get healthy and then reflect on those parts of my career and one of the things that I noticed at the time was all of those companies when they got to a good place when they started to run well they were all run well in the same way How could this be? How could public company, private equity, startups, early stage, growth stage, when they were run well, they were all run well the same way?”
2024-12-05 · Lenny's Podcast · How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · IDENTIFIED FROM THE TRANSCRIPT · source