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

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Jonathan Lowenhar is the co-founder of Enjoy The Work, an executive coaching firm that helps founders become great CEOs. Over the past decade, Enjoy The Work has supported over 165 founders on their journey to becoming better leaders. In our conversation, we discuss:

• The difference between being a founder and being a CEO

• Common failure modes for startup CEOs and how to avoid them

• The four key elements of an effective go-to-market strategy

• A framework for evaluating potential acquisitions: the magic box paradigm

• How to find and hire the best people

• How to build a repeatable GTM machine

• Why founders need to trust their intuition

• Much more

Some takeaways:

1. Being a great founder is important, but being a great CEO is a different skill. You need to spend time improving your leadership, financial literacy, and communication skills. Recognize your weaknesses and fill those gaps, because mastering the CEO craft is just as crucial as the entrepreneurial mindset that started your company in the first place.

2. Common failure modes for startup CEOs include:

   1. The Robot CEO: Believing emotions have no place in a startup

   2. The Pleaser CEO: Avoiding conflict and difficult decisions

   3. The Perfectionist CEO: Prioritizing being right over moving forward

   4. The Angry CEO: Letting frustrations negatively impact the team

   5. The Laissez-faire CEO: Believing great people don’t need management

   6. The Micromanager CEO: Not trusting employees to do their jobs

   7. The Ready, Fire, Aim CEO: Jumping into action without proper planning or direction

   8. The Riding the Brake CEO: Constantly hesitating to spend or take risks

   9. The Riding the Gas CEO: Driving growth without a clear strategy

3. If you’re thinking about selling your company (and you should, because that’s where most successful startups end up), don’t wait until you’re desperate to be bought. Instead, work backward from the type of exit you want. Whether that’s an acquisition, IPO, or winding down, you need to define the target first. A successful exit doesn’t just happen; it’s a product of thoughtful, proactive planning.

4. When dealing with corporate development teams, don’t try to negotiate in real time. You’ll lose. Instead, push for asynchronous discussions—get the deal in writing so you can take time to process it, get advice, and then respond strategically. This gives you an edge in negotiations.

5. When hiring, focus on three main criteria:

   1. Has the candidate already done what you need them to do next?

   2. Do they have a history of creating “raving fans” in their previous roles?

   3. Do their values align with your company’s culture?

6. There are four key elements to an effective go-to-market strategy:

   1. Ideal customer profile (ICP): Clearly define who you’re selling to and what qualifies them as a good fit.

   2. Positioning: Determine your unique value proposition and how to communicate it effectively.

   3. Demand generation: Identify the best channels to reach your target customers.

   4. Develop a repeatable process for closing deals.

Where to find Jonathan Lowenhar:

• X: https://x.com/jlowenhar

• LinkedIn: https://www.linkedin.com/in/jlowenhar/

• Enjoy the Work: https://etw.live/lenny

In this episode, we cover:

(00:00) Jonathan’s background

(02:56) Understanding the rhythm of well-run companies

(09:20) The founder mode vs. manager mode debate

(12:05) Common company failure modes

(13:36) Common CEO failure modes

(25:25) The magic box paradigm for selling your startup

(43:07) Advice for founders on building relationships

(49:28) Hiring and building an amazing team

(57:11) Types of executives: architect, optimizer, scaler

(59:45) Working backward in hiring

(01:02:54) Four key components of a go-to-market strategy

(01:15:01) Trusting founder intuition

(01:19:12) Founder vs. CEO: different roles, different skills

(01:20:52) Closing thoughts and lightning round

Referenced:

• Founder mode memes: https://techcrunch.com/2024/09/04/those-founder-mode-memes-keep-coming/

• Founder mode: https://paulgraham.com/foundermode.html

• “Founder Mode” Is a Dangerous Red Herring: https://enjoythework.com/founder-mode-is-a-dangerous-red-herring/

• Magic Box Paradigm: A Framework for Startup Acquisitions: https://www.amazon.com/Magic-Box-Paradigm-Framework-Acquisitions/dp/0692778047

• Facebook Buys Instagram for $1 Billion: https://archive.nytimes.com/dealbook.nytimes.com/2012/04/09/facebook-buys-instagram-for-1-billion/

• Chris Voss on X: https://x.com/fbinegotiator

• Who: https://www.amazon.com/Who-Geoff-Smart/dp/0345504194

• Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/

• Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/

• Nathan Blecharczyk on LinkedIn: https://www.linkedin.com/in/blecharczyk/

• 4 questions Shreyas Doshi wishes he’d asked himself sooner | Former PM leader at Stripe, Twitter, Google: https://www.lennysnewsletter.com/p/shreyas-doshi-live

• Traction: How Any Startup Can Achieve Explosive Customer Growth: https://www.amazon.com/Traction-Startup-Achieve-Explosive-Customer/dp/1591848369

• Adam Grant on LinkedIn: https://www.linkedin.com/in/adammgrant/

• This will make you a better decision maker | Annie Duke (author of “Thinking in Bets” and “Quit,” former pro poker player): https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke

• How to identify your ideal customer profile (ICP): https://www.lennysnewsletter.com/p/how-to-identify-your-ideal-customer

• How to get your marketing team to drive more impact: https://www.lennysnewsletter.com/p/how-to-get-your-marketing-team-to

• The Five Dysfunctions of a Team: A Leadership Fable: https://www.amazon.com/Five-Dysfunctions-Team-Leadership-Fable/dp/0787960756

• The Untethered Soul: The Journey Beyond Yourself: https://www.amazon.com/Untethered-Soul-Journey-Beyond-Yourself/dp/1572245379

• Will & Harper on Netflix: https://www.netflix.com/title/81760197

• Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o

• Aura frames: https://auraframes.com/

• Augie studio: https://augie.studio/

• Harrah’s Entertainment: https://en.wikipedia.org/wiki/Harrah%27s_Entertainment

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.