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

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?"

(instrumental music) 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.

I'm kind of tired of talking about Founder Mode, but it feels like what you're describing is Founder Mode and Manager Mode.

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.

Something you talk about are kind of these two phases to a startup journey, and most people focus on the first phase.

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 or consumer.

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.

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. (instrumental music)

Today my guest is Jonathan Lowenher. 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 Lowenher. Jonathan, thank you so much for being here welcome to the podcast.