When Jonathan Lowenhar says he enjoys his work, he means it. He’s the founder of Enjoy the Work, a firm that helps startup founders grow into actual CEOs. Not “founders who can speak on panels,” but operators—leaders who can run companies with hundreds of employees and real stakes.
I had him on Keep Going to talk about what happens when the startup dream gets real—and why so many founders hit a wall once they find early success.
Startups begin with an idea. A spark. A product that someone has to build. But if it catches on, suddenly the job changes. “The market gives a shit,” as Jonathan puts it. And now you’ve got to run a company.
That’s where things break down. A lot of founders want to build the next Spotify or Airbnb but haven’t thought about what it takes to lead 100 or 1,000 people. Jonathan runs a thought experiment: How would you run a company with 100 employees? Most founders have no answer. That’s the gap Enjoy the Work tries to fill.
His firm doesn’t work with everyone. They only work with founders who want to get better. Not the ones who think they need a handyman to fix a broken team. They work with the ones who want coaching, feedback, and change.
One story he told stood out: a founder who wanted total control. He ran a climate tech startup with about 100 employees. His idea of management? A weekly spreadsheet detailing what every person should be doing. Engineers, PMs, executive assistants—everyone got orders.
Two weeks in, everyone hated it. It didn’t work. So Jonathan asked him, “Do you want to be right, or do you want to win?”
That’s the question at the heart of all this. Control feels safe. But real leadership is about trust. You don’t scale a company by acting like a parent to 100 kids. You hire adults. You lead, you don’t command.
They worked with his leadership team to change things. Moved from top-down control to clarity, autonomy, and purpose. Set goals, built systems, gave people the tools and trust they needed.
Jonathan sees the same patterns again and again. Founders stuck in fear mode. CEOs building companies around themselves instead of their customers. Startups built to please “the audience of one.”
Fear is a bad decision-maker, he says. It’s what leads to wild overcorrections, micromanagement, and burnout. The fix isn’t therapy (though maybe that too). The fix is building actual strategy. What does winning look like? What could kill the company? What can be fixed?
And most of all: what does the founder need to stop doing?
That’s where many crash. A product-focused founder hides in code. A sales CEO just hops on more calls. Jonathan’s advice is simple: your calendar reflects your priorities. If you’re spending your time in the wrong places, the company suffers.
There’s one more thing he said that stuck with me. Startups often fail not because of murder, but because of suicide. Founders kill their own companies. Not on purpose—but by refusing to adapt. By avoiding the hard work of learning how to lead.
So what’s the goal of Enjoy the Work? To help founders grow into leaders before the board replaces them. To give them the tools to not just start something great, but run it all the way to the end.
If you’re a founder—or even thinking about starting something—listen to this one. Then ask yourself: are you doing the job, or getting better at the job?
This is Keep Going, a podcast about success and failure. I’m John Biggs. See you next week.
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