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

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“And you know that, like, there's better, you can see it. That's where we help. Send us a note. Love to chat. How can listeners be useful to us? So we are voracious readers All we try and do is study how do the best startups do X from tiny things like how do they run all hands meetings or off sites to the big metatopics of what is going to repeatable go to market even mean or what is financial planning in a way that's useful or how do you set goals that won't make you roll your eyes? We consistently learn from the ecosystem of podcasters and authors and journalists like, go look at this material. So, if your listeners have a favorite X on whatever topic in running a startup, send it my way. All we love to do is read and chew on that stuff.”
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
“Love that. So let me unpack those three. The first one is Enjoythwork.com or just find me on LinkedIn. I'm not hard to find. Send us a note. Who should ping us is very simple. If you're a founder out there or a CEO out there, and you know in your heart that there is some gap between how you're running the business and how the company's going and how it could be going and how you could be running the business. There's some gap there. We're here to help. Now, our expertise, as we talked about in this call, is company building. So if you just have an idea in a napkin or you have a science experiment that you're not sure worth, we're useless. Like, that's not us. But if you have some breadcrumbs worth following, like the business is starting to work, you're series A into B and beyond.”
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 primary game that I played was Caribbean stud poker. There's no skill of any kind. You get five cards, the dealer gets five cards. Whoever wins wins. And if you have particularly unusual hands, you get odds on the hand. And I got dealt three, four, five, six, seven of spades in five cards.”
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 get the phone call like 11:30 at night, go on downstairs, they're here, I go downstairs in the casino floor, we're staying at the Las Vegas Hilton. It's since been renamed. But I go downstairs and I can't find them anywhere. Like, okay, whoa, I have cash in my pocket and I'm now awake, so I might as well gamble. Shortly thereafter, Lenny, I have an experience that happens one in $369,000 occurrences and I win $35,421.92 for the trip, I ended up winning $40,000 that I turned $300 to and I was just 21 years old. Which has left me with one of my mantras that I've had for the rest of my life, which some people roll their eyes at, but that is gambling does pay.”
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 we go, and I immediately go sit at some table and start playing some games. And I turn $300 into a few thousand dollars in the very first evening. And that was exciting and it was crazy and it was wild, et cetera. On the third night, which happens to everyone who goes to Vegas for too long, we're all delirious because all of us are staying up all night and being silly and being stupid. And my parents ask me, by the way, this is pre-cell phones. They ask me, hey, can you stay awake? Your uncle in honor.”
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 $300 to gamble with. We're going to be here for five days. This is a vacation. My grandparents are coming in. My uncle and I were coming in. And they're encouraging me. This is all up to you, but try not to lose it all on night number one. Which was good advice to give me. I was 21 and I was pretty much a schmuck at the time. But also part of my experience being there was to interview for a summer internship. This was, I was a college going to be junior.”
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'll tell one of my favorite family stories then briefly. Yes, my family goes back in casino gambling one form or another several generations. My great-grandmother ran an illicit poker game. My grandfather ran numbers out of a gas station. My father's been in the casino industry since Atlantic City in the 70s. My sister is a prominent gaming attorney. And I worked in the industry for a dozen years. So this is my family. And Lenny, I didn't know any of this was weird until I was like in my mid twenties. I turned 21 Old, yes, I'm going to just hide the year. I'm kidding. Anyway, I turned 21 and we take a family trip to Las Vegas because that was normal for us. My father was doing a lot of work out there. So he got his hotel rooms, et cetera. I had never been there before and I was newly 21. And so my parents said,”
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've lived that ever since. So I try and show up. That phrase lets me show up the same way, no matter my setting. If you and I were having a beer or a meal or if I'm sitting with one of my co-founders or clients, it doesn't matter. I show up the same way everywhere. Part of the way I enjoy the work is by having a real friendship, a real intimacy with everyone I enjoy the work and including our clients as well. I want that level of conversation. I don't want the sterile stuff over here with my work environment versus my personal versus my family. It's just one version of me.”
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 first one, and the one I probably most commonly refer to is that there is only one life. Quick backstory, and I know it's a lightning round, but I'm guilty of these stories. I went for a walk with a girlfriend of mine a bunch of years ago, and we did this once a month, and we would always have a pretty typical ritual of kind of giving each other life updates to begin the walk. And so I started the conversation with, so there's the family update and then there's my work life, and then there's my social life. She's like, no, no, no, no, no. Stop. That's all bullshit. It's one life. Stop assuming that there are these pretend walls between them or among them.”
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 combination of the ease of the software and the quality of the imagery is better than anything I've tried and I've tried a bunch of them. A-U-R-A frames, and this is not an Enjoy the Work Company. This is just one I'm a giant fan Second one is an enjoy the work company called Augie Studio, AUGIE Studio. This is Canva for video. It can turn anyone with no engineering skills whatsoever, no code video creation with full editing tools. So suddenly you can create Branded, high fidelity, high quality commercial video in minutes with no effort. It's amazing. It was built by two media tech co-founders that were building this thing pre-Chat GPT. And it's just growing like this. And it's super fun. And the guys are great. So AUGIE Studio.”
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
“Two, and one is I'm going to talk my own book, but I still love it. The first one is Aura Frames. These are digital picture frames. They're amazing. The UX for them is incredible. The quality and their pieces of artwork. So grandparents, in-laws, parents, we have multiple in our house. Just love it.”
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's so many moments in it that are really sweet. As an aside, this was 20, I don't know, April 2020. And a group of our very close friends said, hey, how are we going to keep in touch? And so we started what we call the movie club, and we routinely either pick a TV show or a movie. We all watch separately. And every two weeks, we get together on Zoom at night. Talk about what we just watched. Some have been great, some have been terrible. But Willen Harper was our most recent.”
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 just watched and really enjoyed, by the way, I have a three-year-old at home, so the amount of content I now consume is reduced tremendously. But my wife and I just watched Will and Harper. This is the documentary between Will Farrell and his very dear friend, who just recently transitioned, and they road trip across the country together. And it was freaking delightful. It was sweet and endearing. And one of the better things I've watched in a while. TV show Slow Horses. I'm utterly addicted. I'm only midway through season two, but I've been voraciously Sleeping less and watching more.”
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 second one goes more personal, it's a book called Untethered Soul by Michael Singer. It's this wiz, at least for me, the first introduction to this idea that I am not my brain. And that my brain can be a tool that serves me well, and at times doesn't. So that would be number two”
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
“Number one business book that I've recommended. Would be five dysfunctions of a team. Do think it always comes back to team. The right team can solve all the things. And that book is a beautiful distillation of the most common problematic archetypes that show up in a leadership group. So that's the number 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
“I am now fully off the very awkward soapbox I've been sitting on for a long time. So we can go to lightning round whatever you're ready.”
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 be a founder is a state of being, it's an attitude. It's courage. Instinct It's a capacity to push through despite all sorts of evidence suggesting you're wasting your time. Be a CEO is a craft More founders who can accept that those are two separate things and they're both equally important to build. Ascendant startup, the better all of us will be. And so, what I would encourage every founder out there that wants to go build something substantial. Go work on your craft. In addition to working on the business. Honest with yourself about here's the shit I'm bad at. I don't know how to read a financial statement My board meetings suck. Half my meetings that I have with my leadership team, we all walk out of there saying, What did we just accomplish right now? Or I get to the end of my workday and I'm like, I didn't get anything 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
“Intuition comes from, in my point of view, A deep understanding of self The capacity to get quiet and be well resourced, meaning you've slept well and you've eaten well and you have enough love in your world. And I think Founder mod Can confuse. My intuition says I should just do this job for them and fire these three people. That's not intuition. That's reaction That's a fear response. And when the founder says, I sat with this. Felt it out I can see I need to terminate my whole go-to market team and start over. Isn't working. And I have data that supports it, but I know this isn't working. I'm like, let's go with that. I'm in. Let's do it.”
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 so, in those moments, we'll just say, can you get really quiet? And the founder you're talking about, if I have a story in my head, He was facing a breakup moment With his co founder And I asked him He's good at getting quiet What did the voice say to you way back when? And the boy said to him This is the wrong fit. This isn't going to work. He believes in different things than I do, and that's going to go badly. The lizard brain didn't want to believe that. So it took another year”
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
“When the mania of our chaos of our lives get in the way of that voice. And so whenever our founders face one of those moments, it's not a framework. It's not a playbook. Or even a directed piece of advice from us to say, you should just go left. I've seen this before. Go left. Nope. I trust founder intuition. If the founder says, this business is still going to work or this CEO is, this co-founder is the wrong person, or yes, it's time to sell. I'm in. We're just here to support them. And we try and be the only person in their life that is fully on their team because we're not on the preferred side and the caps table. We're not fiduciary. We're not board members. We're not a co-founder. None of those things.”
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 most of the time, Lenny, when I frame it that way, the person across me says, yep, I know that voice. And I'll ask, how do you hear it There usually be some version of I have to get really alone, really still, really quiet, walk on the beach, listen to music. Work out, play with my pet That voice is who you are, it's not your brain. Your brain is a tool. It's our hands, it's our feet. Just a tool. It's a pattern recognition machine. But who you are, if you can watch your brain, you know what you're thinking. Like, oh, look what my brain's doing. That means you're not your brain. It's something else. And that's the little voice. Little voice is going to be right. Where we get screwed up in life is when we stop listening to that voice.”
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 impossible not to be a startup CEO. Not face Many existential moments Is my company going to survive? Did I make a mistake? Will I ever be hired again? Should I sell the company now? Should I break up with a co-founder? Should I fire this critical employee? Happen to all of us. And fear is not a good decision maker. Our lizard brain is a really bad decision maker in those moments. And so, what will often Share with the founder who's facing one of these scenarios. And I know the CEO you're describing, and he was facing one of these scenarios. Say to them Do you know that little voice when you get really still, the quiet one, that says you should marry this person? You should take this job You should start this company. Watch out for that human. They're a bad 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
“Opposed to what do I really believe I can do to get there, changing top of the funnel, changing conversion rates along the way, changing deal size or deal length, et cetera, based on my recent history, and then have a conversation about the gap between where I think the business reasonably can get with some ambition. Where I think I need to be financially That's the more mature conversation. And that's the one the Ready Fire AIM CEO doesn't have. That's the one most founders have only started to learn to have over the last few years when capital dried up.”
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 one thing I'll share, this goes back to the Ready Fire aim that we talked about earlier. That there's implicitly a funnel, a mathematical funnel to what we just described. And founders often make the mistake when planning for the year ahead of I need to be at this revenue to justify this multiple. And then all of the funnel math is a plug. That's just death. Opposed to here's what's been true for the last three months, six months, nine months, 12 months. And then, what assumptions can I reasonably make with ways I'm going to influence that funnel going forward to go build up to where I think I'll be a year from now? It just lowers the bias that your planning process operates with. But when a founder starts from a place of, I have to get the 3 million or we're dead, you're already dead.”
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
“Amazon just sold books We can start with one thing and be great at it So, where the founders often get hung up on for us is that they've moved toward selling without contemplating ideal customer profile, without contemplating qualifications, without contemplating discovery questions to get to that, and most importantly, kill criteria of If this is true, do not sign them. Even if they want to go out on a date with you.”
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 said, so which of your four customers is your favorite? Which one, if I got them on the phone, they would rave about you. They would be salivating openly with a chance to evangelize what you're doing for them. And they was like, oh, that's clear. It's this one of the four. Great. Tell me about them. What you start to see and pull apart from that is the founder does have an ideal profile. They do have a dream. Now, there are all sorts of risks about is the world too small? Is it not a big enough market if they get too tight? And founders get so caught up in that and it's a mistake. Because all we're looking for in the beginning is a white hot center of opportunity, a small population that is an enormous fan and is getting enormous impact. We can worry about adjacencies and expansion later. I like to remind them that”
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
“What do they look like? And if you have any kind of install base, I'll ask the question. I just did this with the founder the other day. They are enterprise whale hunting business. They have four large customers.”
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
“Early stage founders, and this is certainly more true for the first timers, Lenny, than the veterans, because they learned this problem. The first timers are Like 20 something year olds in a bar. They're being social for the first time in their lives. And anyone that makes eye contact with them is enough for them to say, I want to go on a date with you. That's it. There's no discrimination of any kind. Like, oh my God, they like me. I'm in. That's the mistake that hounds first timers. Veterans and those we get our hands on instead we say Let's imagine you could build your perfect customer in a lab, like Petri dish, and you grew them.”
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 also allows for is an evening of the evening of the playing field between fast processors and slow processors, introverts and extroverts. Because they're all equally potentially talented in your room. But if you do live brainstorming, You have diminished all the folks that prefer to sit and chew on something first.”
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, when the founders weigh in, You don't know. They're just a part of the mass. Let everyone read the thing. I even like the Amazon. And then have a debate. What it allows for is Dampening Of the founder effect in meetings.”
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
“Brainstorming, especially. And so, what many of our founders don't recognize because they just see like, hey, I'm just sitting around a table with a group of folks I respect so we can just debate things as peers. No, you can't. You're a founder. Your voice has a megaphone attached to it, even if you can't hear it So you have to turn down the megaphone. If you actually want to learn what your people have to say, So, brain writing is I'm going to expose an idea and I want everyone to now write and weigh in on their offer. It could be in a survey. It could be in a shared doc, what have you. My preferences in through some sort of methodology, you are now sharing your opinions, comments, edits, dreams in an async way that no one else can see until it's all combined, maybe even ideally without authorship identified.”
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
“Oh, first time I heard of this was Adam Grant. I don't know if he's the originator of the idea. Brainstorming, you talked about this a bit in your Annie Duke podcast as well of how horribly coercive meetings can 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
“We try and break this complexity of going from individually selling to building a machine into just these four buckets. Who am I selling to? What do we want to say about ourselves? How do we reach them? How do we close them?”
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
“Instead, which of these might make most sense next? A simple 2x2 matrix can work here, like some experimentation, some brain writing love brainwriting, not brainstorming. I know you've talked about that on prior pods. And then high impact, low effort. Can we think of the three or four experiments we want to run by channel? Let's go play. And then fourth, sales. And this is the codification of a playbook. How are we having the conversation? How are we doing discovery? How are we handling objections? How are we doing demo? How are we moving to close? If we can get through those four, then we can start to talk about deployment and customer success and upselling and account management, et cetera, et cetera. Those are good problems to have. Oh my God, my install base is so large I need to manage it. Great, great freaking problem.”
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 then, how do we represent that in the world? That's branding and artifacts and identity work, et cetera. Next is demand Will simplify to say how do we go find the humans we want? Long loved the book Traction, Gabriel Weinberg. I'm going to forget, unfortunately, the co-author's name right now, Jason Maher? Sorry? They talk about the 19 channels that all companies have availability to, they're the same ones. The book has got a couple of years on it, so there are a couple of new channels that have popped out since. We then try and expand Aperture for our founders is rather than just think about meeting your next customer through however you did at your last company. Bias”
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
“Our founder is even the most capable of them find this topic pretty overwhelming because it branches into so many areas. So we do try and distill it to something that is in bite-sized chunks. We think of it in four pieces. First piece is ideal customer profile. Who do we really want to sell to What are their qualifications? What are the discovery questions we would use to get to those qualifications? What are the kill criteria to know that this is fool's goal? This really isn't the human. Second bucket loosely called marketing. Within that marketing is also positioning. So, what is our uncommon denominator from the enemies? So, who are we competing against? Is it actual companies or is it status quo in some sort? What are they great at? What are we great at? What are we great at that they're not?”
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 much of our work is to separate them from the day to day, which is enormously important, not in any way denigrating it and Need to know where I'm headed and why, and how I'm going to measure progress along the way. And so so much of what we're doing with them is saying. I want to hear from you what you think success looks like. I'm going to push back and pressure test a bunch of things. Define that in a way we agree on what who needs to do the work along the way and how we're going to keep checking on it to keep feedback loop short. We can go back into business and then we'll check again in a week or in a month.”
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 once I actually have the quantification of here's what work needs to be done. I now know what resources I need to be able to pull that work forward, and therefore now I know what kind of humans I need, whether I'm hiring or renting, and that should drive the conversation, not the, oh, God, I need another PM. No, here's the set of features that we've said matter most this year. Here's the gap in the resources we have and the resources we need. That's why we're hiring this role. And here's what success would look like 12 months from now or six months from now. So they're tying back to what would change about the business. And this is this recurring theme of our work with our founders. They're so in it, Lenny. They rarely have time. Sit above what they're working on this notion of working in the business versus on the 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
“Hiring is never the goal, and it's often the first thing that we'll hear from a founder. I have to hire this person. One that is so dangerous for confirmation bias, like the hiring manager is always the one most burdened by that particular bias, but it's also hiring's never the goal. So, we will pull them back to over and over and over again, which of the three milestones matter? Fundraise, exit, profitability. What is the change about the business, for example, to get to that fundraise? Do we quantify that change, some sort of goal setting framework? OKRs, EOS, I don't care. All goal setting frameworks have the same bones. There's some description of it. There's some quantification of it. There's some work that has to be done. There's some accountability rituals with clear owners and clear agreements.”
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
“Story in my head is that talking to me and my colleagues sometimes can feel a little like death by frameworks. We have one for everything. And in this example, I think if you're going to be sustainably successful in any kind of job, I don't care what it is. Three things have to be true. You have to be good at it. You have to like it and the market has to give a shit about it. And if one of those is off, you're not staying in that job long.”
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
“Scalar is saying, okay, now how do I find leverage? I have 10x more accounting X, or how do I get other people to sell for me? They're all going to be called VP of sales or chief revenue officer. They're completely different archetypes. And that same person exists in engineering and in product, et cetera. In those cases, I only would want to bring on an architect. They'd been an architect before. If they had only been an optimizer, they are going to fail because they've never written playbook from scratch.”
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
“Watch and listen and listen to recordings and pick their brain to pull the magic from the founder of like, oh, here's the dance that she or he goes through to actually close a deal. And they write first playbook. And the goal of the codification of that is so you can bring on a first account exec and the next account exec, because account execs back to our language earlier in this adult children dynamic are children. You need to give them structure for them to win. That's the architect. Optimizer. This is someone who's now going from a few account execs to maybe 10, 15, and we now have targets we have to hit. The business is now reaching a different level of Professionalism and expectation. And you have to optimize that earlier playbook to try and find more efficiency and performance out of it.”
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
“Want some evidence that they're comfortable getting on the phone or showing up at meetings or showing up at events. So that they've done it before should be reviewed or thought of creatively. Now, for more senior roles? Want it explicit. We think of, for example, for executives, Lenny, we think there are three types of executives that startups end up hiring over time. We call them the architect, the optimizer, and the scalar. Architect, let's use sales as an example. This is someone who has to build a playbook. So they are going to uncomfortably stay close to the founder.”
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 one of our companies is hiring a team of reasonably junior account exec Looking for folks that have been out of school for two years. Now that means they are highly unlikely to have had three years of quota achievement you get the point. Okay, so how do you hire someone who's already done it? We know what success looks like 12 months later. For that role, they've learned how to hunt. They've been able to create pipeline of X and close Y in business, et cetera. What we are looking for then in their history, do they have any sales chops of any kind They could be selling Girl Scout cookies or tickets to some of the event. Or they work for a nonprofit for a while. I don't care, but I want some evidence that they've sold.”
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, and if for the recruiters out there, a really simple way to kind of get rid of a lot of the crap that ends up showing it up at the top of the funnel is just to ask the simple question even in the cover letter of your last ex-bosses. How many would get on the phone and say you're amazing? If there's any equivocation in the answer, great, move on.”
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 beautiful example of how Interviewing for values is independent of title. You'll find people in the company at every stage of a company that are the best ambassadors, the best embodiments of those values, please use them for interviewing. And in addition, they love it. They're protecting their castle, like they love where they work, they want to keep it that 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
“They're designed to get at these notions of have they actually done this kind of work before they've been pulled or pushed in their career? And are they your kind of human?”
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 if you see a history of that ding ding ding, ding ding, really attractive candidate. Third Core values matter a lot. Culture is not an accident. Culture at scale is the codification of what matters to a business. And the ritualization of living those values. It starts with whoever the founders are, and that it will emanate across as long as the founders are super consistent. That also means you need a methodology for evaluating the next human in front of you on whether they actually represent your values. We think of these interview stages in a way similar to the book. We use slightly different language We think that there is a culture interview. There is a functional interview, and there is a technical interview.”
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
“Start with it's 12 months later. You hired the person, they started today, 12 months have gone by, you're clinking champagne because of how great it's been. What's changed about the business? What does success look like? 12 months later, document it. And then when you interview people. Look for people that have already done that stuff. The notion of Does the person in front of you have a history of creating raving fans? Talk in the book about this idea have you been pulled or pushed in your career? Outstanding performer in job A. Is a high likelihood that in job B, someone associated with you in job A is going to pull you into the next thing and then pull you into the next thing and pull you into the next thing. And you'll never do a job search because you were great.”
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
“They had a consulting firm that dates back to the mid 90s, and they wrote a book in like 2007 or 2008 called Who, the A method for hiring. We have operationalized that book and then expanded on it because there are some parts of it that we found a little dated, but it's really still as applicable today as it ever was. And I think there are three core mistakes that founders make all the time that can be really easily rectified. The first one is You should hire people who have already done the thing you need to have done next for them. And I know that sounds simple, but founders don't think of hiring that way. They start with a job description We've been taught that for a long time. Start with the job description. It's a fucking mistake.”
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