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

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

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Find the transcript at: https://www.lennysnewsletter.com/p/how-a-great-founder-becomes-a-great-ceo-jonathan-lowenhar

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Where to find Jonathan Lowenhar:

• X: https://x.com/jlowenhar

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

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

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

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

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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

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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: