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HOUSEKEEPING 📨

I saw the tweet below recently, and it really got me thinking about the quote that; “Capitalism is the worst economic system, except for all the others.” The quote is attributed to Churchill, although like most good quotes he actually never said it.

The tweet—for all of you too lazy to click it—shows the incredible progress we have made on child mortality, life expectancy, GDP, women’s education, and more over the last century or so. But more and more and more all I see and hear from people around me is how much they are struggling. Financial stress is everywhere, real per capita GDP is going backwards, young people are giving up on the idea of buying homes. And yet Elon will likely become a trillionaire within the next decade or two.

I understand that the profit motive attached to capitalism motivates people to create more, and add value to the world. Hence why capitalism beats communism. But what is the utility of creating trillionaires? Was this what Adam Smith envisioned when he spoke about the invisible hand of the market? If you spent $1 million dollars a day, it would take you 2,740 years to spend a trillion dollars.

Recently, while walking my dog Ziggy, I came up with a thought as to how capitalism could be improved upon. Sure, we should have the profit motive we have today, but should a business actually begin to succeed, much more of the successes should go back to the people that built it. I jotted down what I thought it should be called—distributionism—in my phone, and kept walking.

Since I stumbled upon this lesser known economic model, I can’t really get it out of my mind. Think of it, the problem with capitalism is it knows no bounds. The problem with socialism is governments are somewhat inept at managing tax revenues, and the problem with communism is, well, no one has reason to want to work hard.

What if you could have the drive of a capitalist society, with greater wealth spread across the people, without the government getting in the way. The way I am thinking of it in practice would be some sort of a forced distributions of profit to employees. Kinda like a much higher minimum wage, but only scales as the company does. Sounds rather utopian to me.

Anyway, that’s enough of my ramblings for today. Let’s move on to today’s interview, which I think you might just love. I know I loved it!

INTERVIEW 🎙️

Jonathan Lowenhar, Founder & Managing Partner at Enjoy The Work

Jonathan Lowenhar, Founder & Managing Partner at Enjoy The Work, helps great founders become great CEOs. Over the last decade, Jonathan and his team of experienced startup operators have supported nearly 200 companies, with a combined valuation of $13 billion, spanning Tel Aviv to Montreal and New York to the San Francisco Bay Area.

Notable clients include Tipalti, Honeybook, Shef, Paper Education, PeopleOne Health, Mudflap, Darrow.ai, Indus.ai (acquired by Procore), Enview (acquired by Matterport), TheWild (acquired by AutoDesk), and Veo.

What is the biggest challenge founders face when becoming or transitioning to CEOs?

They don’t realize it’s a completely different job. A founder’s job is to invent something—to will a product into existence where nothing existed before. A CEO’s job is to steer an organization in a specific direction. So the biggest challenge is this: what got you here won’t get you there. It requires shifting from improvising to building systems, and managing people in roles you’ve probably never done yourself.

Let me give you an example. One of our big success stories from a few years ago: the CEO spotted a problem with how money moved between large companies and their suppliers, especially across borders. He wrote the code himself for two years, landed the first customer, and launched the product; and it worked.

But then came the next phase: building a company around that working product. He had to go from doing everything—coding, sales, deployment—to hiring people, managing them, and building a functioning operation. It was a totally different job.

Which founders make that transition successfully, and what do they have in common?

I’d say a few things. One, there are founders who are deeply self-reflective and those who are not. The ones who look in the mirror recognize at some point that the improvisational approach that invented their first product can actually get in the way of empowering others to manage, sell, or market it. They admit that what got them here won’t get them there.

Two, they embrace systems thinking. If I’m just managing myself, I don’t need process, protocols, or rules, I just figure everything out. But to lead an organization, you must care about how people operate: defining clear systems, rituals, and workflows so work happens repeatably and reliably. Founders who appreciate why repeatability matters—and who avoid doing everything from zero—make the leap most smoothly.

What are some examples of systems that need to be built as a company matures?

In the early stage, your entire focus is on finding product–market fit. For us, that means first identifying a real pain in the market, then building a solution that genuinely solves it, and finally testing whether your customers would scream if you took that solution away. To do this at speed and with rigor, you need an ‘experiment engine’—a set of repeatable processes for generating hypotheses, designing tests, gathering feedback, and iterating quickly.

The early stage is about building and validating an experiment engine; the late stage is about refining and scaling that engine into a dependable factory that delivers consistent results.

What are the common mistakes that startup leaders make?

Founders are often more product-obsessed than problem-obsessed. They fall in love with the thing they built, but in the early days that matters less vs the gap in the market you hope to address. Another mistake is hanging on to underperformers too long. Fear makes you keep the status quo. But founder intuition is a powerful tool; founders know when someone isn’t cutting it. After supporting CEOs through hundreds of such scenarios, I safely can say that every time one of our CEOs finally lets the poor performer go, every time they say ‘I wish I’d done that sooner.’

A third mistake among first-time founders is not knowing their own math. They worry about getting products in customers’ hands without understanding the unit economics of acquiring, deploying, and supporting those customers over time; J-curves are fine, but upside-down economics are not.

The final mistake I see—especially among younger founders—is believing they must know all the answers. Being a CEO isn’t about having all the answers; in fact, knowing is the enemy of learning. The CEO has 3 jobs; define the mountain to climb, surround yourself with the right people, and give them the tools they need to win. Problems are sure to come up along the journey. But our best CEOs know that if they’ve surrounded themselves with the right team, then their role is far more about offering great questions, then great answers.

What’s your philosophy on when and how to remove someone?

When we have to fire someone, it means we’ve made an error; whether in hiring, training, ramping, or support. As startup CEOs, we often overthink the process and lean on large‐company rituals like performance improvement plans or drawn‐out reviews, which exist more to avoid litigation than to actually close skill gaps. If you spot a mismatch, be it in someone’s alignment with your company values or their ability to meet role competencies, you need to address it head-on. Start with a straightforward conversation: explain what the role requires, share what you’re observing, and ask how you can work together to close the gap.

If they don’t know how to improve, you coach; if they aren’t willing, you need to understand why, because the business depends on it. When that discussion repeats without progress—especially for an early hire who hasn’t yet demonstrated excellence—it’s time to part ways.

There’s a different approach when a proven high performer suddenly dips. In that case, you lead with curiosity, reminding them of their past successes, pointing out the recent decline, and asking what’s changed. The goal is to recover the strong performance you once saw.

The hardest barriers are our own reluctance to have blunt, authentic conversations and our fear of the short-term disruption, but holding on to underperformance ultimately costs far more in team morale and company culture than the brief loss of headcount.

How do you craft a memorable startup story?

I receive different versions of this question; either how to craft a memorable story, or what are the essential elements of a thirty-second pitch. They’re really the same. The first thing we encourage founders to do is treat it as a conversation, not a pitch or a monologue, because monologues put people to sleep, whereas dialogues draw listeners in. No one enjoys being talked at. You don’t pull someone into your story by talking at them; you draw them in by inviting them into a back-and-forth.

When it comes to structure, I ask founders five questions in a row. Who is the hero?—Be specific; a doctor, an accountant, an astronaut. What is that person’s pain? How do they solve it today, even if it’s clumsy or manual? How do you, as the entrepreneur, solve that pain? And finally, imagine utopia: five years from now, everything has worked perfectly, how has the world changed?

For example, in my own story at Enjoy the Work, the hero is the founder whose company grows faster than they can manage. Today, those founders cobble together advisors, read books, scan blogs or hire polished executives. We solve that pain by auditing both the founder and the company to pinpoint skill gaps and then teaching the exact leadership practices they need as the business scales. In our utopia, every high-velocity startup CEO has the skills to stay behind the wheel for as long as they choose, rather than being replaced by impatient investors the first time the business hits a rough patch.

What are the most crucial elements of fostering a great culture?

A lot of first-time founders hear the word ‘culture’ and think it’s woo or assume that hiring reasonable adults is enough—and they’re grotesquely wrong. Culture is your cheat code for managing the inevitable gray areas, from interpersonal conflict to emotional swings. As a founder, you have a whole set of beliefs in your head about what professionalism looks like, how collaboration works, what trust, honesty, urgency, and service mean, but none of that matters until you make it explicit.

I don’t believe in telepathy—maybe one day Neuralink will change that—but today, if you want shared expectations instead of guesswork, you have to use words and write them down.

That’s just as true for culture as it is for any other part of your business. A few weeks ago, a new hire of mine showed up five minutes late to our one-on-one. Because we had already codified our core values, trained everyone on them, and reinforced them in Slack, in meetings, and even in our weekly letters, I was able to say, ‘Do you remember during onboarding when we talked about being present? That means showing up on time.’ She apologized and assured me it wouldn’t happen again.

That moment was a perfect example of how clear, documented values turn feedback into a simple ‘cheat code’ rather than an awkward negotiation.

🔥 Want to read more on culture? Check these posts to see how my startup, Athyna, does remote work, onboarding, and benefits.

What are the biggest green flags you see in the best founders?

Green flags start with deep curiosity. In every first meeting with a founder, we lovingly interrogate them, explaining, ‘We’re not investors or fiduciaries here; I just need to know everything.’ I’m like a doctor doing discovery. Then I ask hard questions—’Why are you doing it that way?’—and if they lean into that curiosity rather than get defensive (‘Yeah, but…’), that tells me they’re open‐minded and coachable.

The second green flag is boundless enthusiasm. A successful venture‐backed startup can take eight to thirteen years for an exit, and if sound bored by your own company, I don’t believe you’ll have the juice to see it through. I need to sense that deep passion for the problem they’re solving. Our most successful founders care enormously about the pain in the world they’re trying to solve. It shows up in every conversation.

Finally, I look for CEOs who see their role as a craft to be learned. Great founders can say, ‘Here’s what I do well, here’s where I fall short, and I want to get better.’ They understand that the ceiling of their company is tied to their own growth, and they embrace the work of sharpening their leadership skills over time.

How do you help founders achieve peak performance?

I’ll start with ‘your physical state drives your mental state.’ We explore how our founders take care of themselves; the mythology of the startup grind has gone too far—working 22 hours, barely sleeping, eating like crap—it is a stupid badge of honor that just leads straight to burnout. We ask how much they’re sleeping, how they exercise, whether they’re spending time with loved ones, if they’re drinking enough water, and what their self-care routine looks like.

Third, we model vulnerability. At the beginning of every call—and we’ve worked with now 200 founders in the last 10 years—we start with, ‘How are you?’ And not some truncated, polite version: ‘Really, how are you? The good, the bad, the ugly.’

Not all of our conversations are about dashboards or fundraising. Sometimes founders reach out in real crisis. Breakups, death, the kind of stuff that makes company metrics feel irrelevant. And when they do, we don’t jump back to work topics. We ask ‘How do we give you space to grieve? How do we take care of you? How do we protect you and the company while you recover?’

Most CEOs think they must wear armor that never comes off, but showing vulnerability. ‘Hey, I’m doing shitty today: my daughter’s sick, my wife’s traveling, my dog’s recovering from surgery, my elbow’s killing me.’ And not asking anyone to fix it permits founders to be human, and ultimately those are the kind of relationships that allow my partners and I to enjoy the work.

And that's it! You can connect with Jonathan at LinkedIn here. To learn more about Enjoy The Work, check out the website here.

BRAIN FOOD 🧠 

TWEETS OF THE WEEK 🐣 

TOOLS WE USE 🛠️

Every week we highlight tools we actually use inside of our business and give them an honest review. Today we are highlighting Paddle—a merchant of record, managing payments, tax and compliance needs—we use their ProfitWell tool.

See the full set of tools we use inside of Athyna & Open Source CEO here.

HOW I CAN HELP 🥳

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