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[Navigating Entrepreneurial Challenges: Insights from WeWork Co-founder Miguel McKelvey]-[Advice Line with Miguel McKelvey of WeWork]

How I Built This with Guy Raz · B2 · 2026-03-05

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📋 Summary

Navigating the Rollercoaster of Entrepreneurship: Lessons from Miguel McKelvey

In this episode of How I Built This Lab, host Guy Raz invites WeWork co-founder Miguel McKelvey to the "Advice Line" to offer guidance to early-stage founders. The conversation bridges the gap between McKelvey’s high-stakes experience with WeWork and the practical, day-to-day struggles of small business owners. Throughout the episode, McKelvey emphasizes that entrepreneurship is a "rollercoaster" where every experience, regardless of outcome, serves as an opportunity to "grow from and learn something."

The Reality of Valuation and Business Models

Reflecting on his time at WeWork, where the company reached a $47 billion valuation, McKelvey draws parallels to the current "AI bubble." He distinguishes between the "tangible" value of his era—such as workspace or ride-sharing—and the current uncertainty surrounding AI monetization. McKelvey admits that while he uses AI tools daily, he remains skeptical of business models that rely on giving away incredible technology for free, noting that such competitive dynamics can often lead to a "race to the bottom."

Strategic Advice for Niche Founders

McKelvey’s core philosophy for mentorship is simple: be curious and ask questions. During the episode, he provides actionable advice to three distinct businesses:

1. Copa Threads: The Art of Storytelling

Jane Barthel, a neonatologist running a side hustle making colorful, small-batch trousers, struggles with scaling her high-price-point product. McKelvey urges her to "double down on the story." He argues that her pants are "wearable art" and that she must move beyond her website to explain why she charges $295. By highlighting the "artisanal" nature of the product and the local, women-owned factory behind it, she can justify the cost. He suggests using ambassadors and social media to show the "why" behind the brand, transforming the product from a simple garment into a craft-made experience.

2. Good Grief: Mastering SEO and AI Discovery

Melissa Jensky of Good Grief seeks growth strategies for her care-package business. McKelvey suggests a shift in marketing strategy, emphasizing that "AI crawlers" are the new SEO. He advises creating content for every conceivable scenario where someone might need support, ensuring that when a user asks an AI assistant for help, the brand appears as the solution. He also encourages diversifying into B2B channels, such as HR departments, acknowledging that the "managed grief" in the workplace is a significant, yet often overlooked, opportunity.

3. The History List: Experimenting with Narratives

Lee Wright, founder of The History List, wants to lower customer acquisition costs. Despite his success with a 50% margin and a $20 CAC, McKelvey pushes him to experiment further. He suggests that Wright leverage the "narrative" power of TikTok and consider smaller, niche history podcasts for advertising rather than just large-scale networks. McKelvey stresses that if a founder is in a niche, they should "continue to expand the edges of your appeal" to attract those who aren't yet enthusiasts.

Final Wisdom: Facing the Things You Avoid

When asked what advice he would give his younger self, McKelvey offers a poignant reflection on his time at WeWork. He notes that he was "bad at money" and, rather than engaging with it, he hired a CFO to handle it, effectively keeping it "out of sight, out of mind." He identifies this as a mistake, urging founders to be "more critical about the things that I was bad at." He concludes that a founder must be responsible for everything, even the tasks they dislike, because ignoring weaknesses is "not a great model for entrepreneurship."

Through these interactions, McKelvey reinforces that whether you are running a $47 billion company or a local boutique, the fundamentals remain the same: tell your story, solve a tangible problem, and never shy away from the parts of the business that challenge you most.

🎯Key Sentences

1
Here's the thing.
2
Isn't that why we work so hard?
3
It wasn't just somewhere to sleep.
4
What you build with shapes what you create.
5
All right, let's get to it.
Expand All

📝Key Phrases

1
soak up the design scene
2
making the most out of your money
3
live a little
4
building out
5
offset the cost
Expand All

📖 Transcript

Say you've always wanted to take that trip to Copenhagen just to soak up the design scene.
Here's the thing.
If you get smart with your money, you could do things like that.
With Empower, you can start making the most out of your money, so you can go out and live a little.
Isn't that why we work so hard?
To have some fun with our money, like building out that immersive, cutting-edge media room or surprising your partner with a one-of-a-kind weekend getaway.

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