We’re excited to introduce you to the always interesting and insightful Jonathan Lowenhar. We hope you’ll enjoy our conversation with Jonathan below.

Alright, Jonathan thanks for taking the time to share your stories and insights with us today. Are you happier as a business owner? Do you sometimes think about what it would be like to just have a regular job?

Owning a business is exhausting. The pressure can feel unrelenting. You’re the caretaker for everyone—your family, your employees’ families, your customers’ businesses. At times, the constant hum of responsibility makes you wonder what it might feel like to let it all go.

And then I think about the other side. Reporting to someone else. Losing autonomy. Losing agency. Giving up the ability to decide when I work, who I work with, where I work, and how I work. Losing the leverage to immediately and personally benefit financially from the impact I create.

I’ve had “regular” jobs—plenty of them. I struggled with the sclerosis I saw around me: the meetings about meetings, the jargon, the optics, the politics, the jockeying for favor that had nothing to do with creating real value. Sure, I had a steady paycheck, health benefits, and I rarely worried about the solvency of the company. But the inefficiencies, the limitations on my impact, and the ceiling on my compensation weren’t worth the creature comforts.

So for me, the choice was—and still is—clear: I’ll be a business owner for the rest of my career.

Jonathan, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I’ve had a long, varied, and fun career.

The first chapter was in the casino industry—starting in Atlantic City, then Las Vegas. I began in analytics, moved into marketing and sales, and ultimately operations. I ran a billion-dollar business unit for a public company and later led a PE-owned holding company with 3,000 employees.

In 2004 and 2005, I attended a joint MBA program between Columbia Business School and Berkeley’s Haas School of Business. That was my introduction to Silicon Valley—and I was hooked. In 2007, I made the move full-time. By 2008, my second chapter started and I co-founded my first startup, Trooval—an analytics tool for hospitality businesses – essentially real-time lead scoring. We raised venture capital, signed customers like Starwood, Marriott, and Hilton, but never quite reached escape velocity. We sold the company in 2012. It wasn’t a financial win, but it cemented my love for startups.

Soon after, I joined another startup, this time as the first non-founder President of a young fintech company called Taulia. At the time, they had $200K in revenue, a small client base, and about 30 employees. The founders were brilliant domain experts, and I loved the ambition. By the time I left, the business had grown to $20M in revenue and raised over $100M. A few years later, SAP acquired it for nearly $1B.

Those experiences left me fascinated by startups. I’d led a public company division, a PE-backed business, and two startups—and I noticed a pattern: well-run companies, regardless of size, share common ingredients. Vision and values. A real financial plan. Clear goals. Dashboards. Strong communication. Effective management. Talent systems that work.

But early-stage founders rarely focus on those things. They’re consumed with solving a problem and building a product. My question was: what happens if they succeed? The challenge shifts—from building a product to building and leading a company. And if that’s true, where do they learn those skills while racing the clock of a startup burn rate?

That question became my mission (and my third chapter). Ten years ago, I set out to solve it—teaching founders how to become great CEOs.

Our team at Enjoy The Work has since supported nearly 200 startups—many growing from scrappy early-stage teams to international category leaders in law, healthcare, financial services, energy, and climate. Just as importantly, we’ve built a community of well-intentioned, thoughtful humans trying to make a difference in the world.

The name of our firm—Enjoy The Work—isn’t an accident. It’s a privilege to be part of this journey.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

My father had an exceptional career. He was an economics professor, then ran a successful consultancy, and later served in the C-suite of multiple international hospitality companies before returning to private practice for nearly 20 years. He also had rules he lived by—and he passed those rules down to me.

One of them: don’t get close to the people you work with. He believed closeness invited political risk, clouded judgment on performance, and that friendship had no real place in the workplace.

I couldn’t disagree more.

It took time, but eventually I embraced a different perspective. I want no boundaries. There are people in my life who inspire me, challenge me, push me, and fill me up. People I laugh with, play with, explore with. I’m on this planet for a short time, and I spend most of my waking hours working—trying to create something meaningful. Why wouldn’t I want to do that alongside my favorite people?

To be clear, I don’t work with all my friends. I’ve learned there are friends I can work with and friends I absolutely can’t. But for me to truly Enjoy The Work, I need the people around me to be a source of real joy—if not outright love. So I unlearned the lesson of my youth and embraced a non-conventional approach: not only am I open to closeness at work—I won’t work with someone I can’t become close to.

How’d you build such a strong reputation within your market?

I believe startup founders are beset on all sides. Everywhere they turn, they face audiences with selfish intent: investors pushing for better terms, founder dilution be damned; employees asking for raises, regardless of runway; customers demanding new features, never mind the burnt-out engineers.

From day one at ETW, I believed that if we truly put the founder first—with fully aligned incentives—we could be the one party in their corner.

Here’s what I mean.

Our very first client was a young consumer robotics company led by two PhD roboticists, Nick and Andrew. They had a compelling prototype, minimal revenue, and a short runway. I met them through some prospective investors who were exploring the idea of me joining as CEO. After speaking with the investors and getting to know the founders, I told Nick and Andrew that no one should run the company but them. It was too early. Going from zero to one requires founder energy, not a hired gun.

They were passionate and brilliant—but unsure how to move forward: raising capital, managing investors, hiring, and going to market. I offered to help. They were interested but admitted they had almost no funds. I said, “Let’s just get to work. If we can get the round done and launch the business, we’ll figure out economics that work for both of us.” I had no interest in pressuring or exploiting them. I just wanted to help.

We ended up working together for nearly six years.

That approach has never changed. I don’t put myself before the startups I serve—and neither do our partners. Anyone who’s worked with us would say the same. We’re here to serve. If we do that well, everything else takes care of itself.

Contact Info:

• Website: https://enjoythework.com
• Linkedin: https://www.linkedin.com/company/etw-advisors/
• Twitter: https://x.com/EnjoyTheWork

Image Credits

All photography is owned by Enjoy the Work.