How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work)

**Lenny Rachitsky** (0:00)
You basically spend all your time working with founders, and through that studying, you create frameworks and training, and you use that in your work. I think that's what many, many founders are looking for, is how do I avoid pain?

**Jonathan Lowenhar** (0:11)
To be a founder is a state of being, it's an attitude. To be a CEO is a craft. The more founders who can accept that those are two separate things, and they're both equally important to build an ascendant startup, the better all of us will be.

**Lenny Rachitsky** (0:26)
I'm kind of tired of talking about founder mode, but it feels like what you're describing is founder mode and manager mode.

**Jonathan Lowenhar** (0:30)
Founder mode gets me angry. That article just got me hot. It really felt like an excuse. We were giving founders a permission to not learn the job. It's not manager mode is bad. It's the greatest CEOs know when to calibrate which one is needed.

**Lenny Rachitsky** (0:46)
Something you talk about is kind of these two phases to a startup journey, and most people focus on the first phase.

**Jonathan Lowenhar** (0:51)
Phase one is build something people want to buy. Phase two, the one we don't talk about is now you have to build a company around that thing people want to buy. Building a company is always the same. I don't care if it's MedTech or Fintech or hardware consumer.

**Lenny Rachitsky** (1:04)
You've come up with this methodology that you call the Magic Box paradigm that helps founders think about how to lead to a successful exit long term.

**Jonathan Lowenhar** (1:11)
This is a traditional sales process. You build a list of the companies that might want to acquire you. You ping them and you hope you get a deal. Magic Box argues 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. They see the fantasy. They fall in love.

**Lenny Rachitsky** (1:35)
Today, my guest is Jonathan Lowenhar. Jonathan runs a firm called Enjoy The Work, which I've heard amazing things about from so many people over the years. Their firm has a singular mission to help founders become great CEOs. They do this through a blend of mentoring and advising services, which are rooted in their study of how the best startups operate. They take these lessons and fold them into frameworks and advice and training that they offer their CEOs. Their insight, which you'll hear in our conversation, is that most founders don't come into the job knowing how to be a CEO, which includes learning how to do hiring, how to manage financials, figure out growth strategy, road mapping, planning, people management, and so many other skills that nobody teaches a founder. In our conversation, Jonathan shares the most common CEO failure modes that he and his team have seen, the magic box paradigm for successfully selling your startup, a bunch of advice for finding and hiring the best talent, a framework for building a repeatable go-to-market motion, why and how you should learn to trust your intuition more as a founder, and so much more we could have gone on for so many more hours. Maybe he'll be back to share more advice. If you're a founder or hope to be a founder one day, this episode is for you. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes and it helps the podcast tremendously. With that, I bring you Jonathan Lowenhar. Jonathan, thank you so much for being here. Welcome to the podcast.

**Jonathan Lowenhar** (3:02)
Lenny, I am damn excited.

**Lenny Rachitsky** (3:06)
The reason I'm excited to have you in this podcast is that you basically spend all your time working with founders and through that studying what causes them pain, what causes them to fail, what causes them to struggle. Then you take that and you create frameworks and training and you use that in your work with founders and I think that's what many, many founders are looking for is how do I avoid pain? How do I avoid these things that I'm going to probably run into? So to build on that briefly, can you just help people understand what it is you do, what it is your organization does with founders, how you work with founders?

**Jonathan Lowenhar** (3:38)
Yeah. Thank you. I'll tell a bit of origin story that I think ends up answering that question.

**Lenny Rachitsky** (3:43)
Let's do it.

**Jonathan Lowenhar** (3:45)
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, then 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. 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. Like, 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. 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 asked them, Lenny, I asked 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? And the answers universally were the same. Investors would use words that meant grit and tenacity and courage and insight.