Lenny's Podcast: Product | Growth | Career

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

Dec 5, 2024

Jonathan Lowenhar, co-founder of Enjoy The Work, shares his insights on transitioning from founder to CEO, emphasizing the importance of management skills. He discusses various CEO failure modes and how to avoid them, highlighting emotional intelligence. The conversation covers effective hiring practices, the 'magic box paradigm' for acquisitions, and building a sustainable go-to-market strategy. Lowenhar also advocates for trusting one's intuition and the value of reflective decision-making in leadership.

01:34:36

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Episode guests

Jonathan Lowenhar

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Episode notes

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Quick takeaways

Understanding the crucial distinction between the roles of a founder and a CEO is essential for startup success.

The Magic Box Paradigm provides a strategic approach for founders to successfully navigate acquisitions by focusing on narrative and alignment.

Recognizing common CEO failure modes like emotional detachment and people-pleasing can help founders develop more effective leadership styles.

Deep dives

The Differences Between Founder Mode and CEO Mode

To navigate the world of startups effectively, it is vital to understand the distinct roles of being a founder and a CEO. Being a founder is characterized by an entrepreneurial spirit and creative attitude aimed at creating new products or services. In contrast, effective CEOs hone their management skills and operational capabilities to guide their companies to success. The most successful individuals in these roles recognize the need to separate these two pathways, accepting that mastering both is crucial for building a thriving startup.

Intro

2min

Transforming Founders into Successful CEOs

5min

Enhancing User Experience and Leadership Transition

5min

Understanding CEO Failure Modes

13min

Navigating Startup Exits

17min

Strategic Networking for Founders Considering a Sale

5min

Founders' Growth and Hiring Strategies

19min

Navigating Founder's Intuition and Effective Brainstorming

18min

Exploring Meaningful Entertainment and Innovative Products

2min

10.

Life Lessons from Gambling

8min

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: 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

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

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