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

Lenny's Podcast: Product | Growth | Career

Lenny Rachitsky

Technology, Business, Entrepreneurship

5 • 1.5K Ratings

🗓️ 5 December 2024

⏱️ 95 minutes

🔗️ Recording | iTunes | RSS

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Summary

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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Lenny may be an investor in the companies discussed.

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Transcript

Click on a timestamp to play from that location

0:00.0	You basically spend all your time working with founders and through that studying, you create frameworks and training and you use that in your work.
0:08.0	I think that's what many, many founders are looking for is how do I avoid him?
0:11.1	To be a founder is a state of being.
0:13.3	It's an attitude.
0:14.4	To be a CEO is a craft.
0:16.1	The more founders who can accept that those are two separate things and they're both equally important to build
0:23.4	an ascendant startup, the better all of us will be. I'm kind of tired of talking about founder mode,
0:27.8	but it feels like what you're describing is founder mode and manager mode. Founder mode gets me
0:31.6	angry. That article just got me hot. It really felt like an excuse. We were giving founders of permission to not learn the job.
0:41.4	It's not manager mode as bad. It's the greatest CEOs know when to calibrate which one is needed.
0:46.4	Something you talk about is kind of these two phases to a startup journey and most people
0:50.3	focus on the first phase. Phase one is build something people want to buy. Phase two, the one we don't talk about is now you have to build a company around that thing people want to buy.
0:58.0	Building a company is always the same.
1:00.0	I don't care if it's MedTech or FinTech or hardware or consumer.
1:04.0	You've come up with this methodology that you call the magic box paradigm that helps founders think about how to lead to a successful exit long-term.
1:11.5	This is a traditional sales process. You build a list of the companies that might want to acquire you.
1:16.9	You ping them and you hope you get a deal.
1:18.5	Magic Box argues that the best outcomes for early stage startups don't happen that way.
1:23.7	You're never for sale. In fact, you have seduced a buyer. They see the fantasy. They fall in life.
1:34.9	Today, my guest is Jonathan Lowenhard. Jonathan runs a firm called Enjoy the Work, which I've heard
1:40.8	amazing things about from so many people over the years. Their firm has a singular mission to help founders become great CEOs.
1:48.8	They do this through a blend of mentoring and advising services,
	...

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