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Advice Line with Miguel McKelvey of WeWork

Advice Line with Miguel McKelvey of WeWork

Update: 2026-03-05
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This episode of "The Advice Line" features insights from WeWork co-founder Miguel McKelvie, who discusses the company's tumultuous journey and his current role mentoring entrepreneurs. McKelvie contrasts the tangible value of businesses like WeWork with the speculative valuations of some AI companies. The podcast also addresses listener challenges: Jane Barthel of Copa Threads seeks to scale her niche apparel brand while maintaining quality and local manufacturing; Melissa Janski of Good Grief needs to diversify marketing for her care package business; and Lee Wright of The History List Store aims to expand his customer base and reduce acquisition costs. McKelvie offers advice on storytelling, content marketing, targeted advertising, and embracing entrepreneurial weaknesses.

Outlines

00:00:00
Introduction and WeWork's Journey

Guy Raz introduces "The Advice Line," featuring WeWork co-founder Miguel McKelvie. The episode revisits WeWork's rapid rise, its challenges, and McKelvie's reflections on the experience and entrepreneurship as an emotional journey.

00:03:37
AI Valuations vs. Tangible Value and Mentorship

McKelvie discusses AI business valuations, contrasting them with WeWork's tangible market need. He shares his current focus on mentoring entrepreneurs, emphasizing curiosity and helping others explore perspectives.

00:06:26
Scaling Copa Threads: Niche Apparel Brand Advice

Jane Barthel of Copa Threads seeks advice on scaling her women's pants brand while maintaining high-quality, local manufacturing and premium pricing. McKelvie advises emphasizing brand story, local production, and leveraging user-generated content and local partnerships.

00:17:44
Growing Good Grief: Care Package Market Strategies

Melissa Janski of Good Grief needs to diversify marketing for her care package business. McKelvie suggests focusing on content marketing for SEO and AI, exploring B2B gifting partnerships, and using direct mail.

00:31:16
Expanding The History List Store: Reach and Costs

Lee Wright of The History List Store aims to increase his customer base and reduce acquisition costs for his history-themed merchandise. McKelvie recommends increasing advertising, exploring TikTok for historical narratives, and collaborating with history podcasts.

00:41:15
McKelvie's Core Entrepreneurial Advice

McKelvie reflects on his entrepreneurial journey, advising founders to critically assess their weaknesses and take responsibility for all aspects of their business, even the less enjoyable ones.

Keywords

WeWork


A global network of shared workspaces that experienced rapid growth and significant challenges, impacting its business model and leadership.

Entrepreneurship


The process of designing, launching, and running a new business, involving innovation, risk-taking, and resource management.

AI Businesses


Companies focused on developing and implementing artificial intelligence technologies, characterized by rapid growth and evolving business models.

Scaling a Business


The process of growing a business to handle increasing volume, requiring strategic planning and adaptation.

Niche Apparel Brand


A clothing brand targeting a specific market segment with unique products, like Copa Threads focusing on comfortable, high-quality women's pants.

Care Packages


Curated boxes for individuals facing difficult life events, with Good Grief specializing in support for loss and hardship.

Marketing Diversification


Expanding marketing efforts across multiple channels to reach a broader audience and mitigate risks.

History-Themed Merchandise


Products based on historical themes, events, or figures, offered by The History List Store.

Customer Acquisition Cost (CAC)


The expense incurred to acquire a new customer, with strategies to optimize advertising and leverage organic growth.

Content Marketing


A strategic approach focused on creating and distributing valuable content to attract and retain a defined audience.

Q&A

  • What are the key differences between the valuations of AI companies and WeWork's past valuation?

    WeWork addressed a tangible, real-world need for workspace, similar to Uber or Airbnb. While AI applications are powerful, their monetization and exact value proposition are still evolving, making their valuations more speculative compared to WeWork's more concrete market demand.

  • How can a niche apparel brand like Copa Threads scale while maintaining high costs and quality?

    Focus on storytelling to highlight the value of local manufacturing and unique design. Leverage user-generated content and consider strategic local partnerships. Emphasize the "wearable art" aspect to justify the premium price point and attract customers who value craftsmanship.

  • What marketing strategies can a care package company like Good Grief use to break through a plateau in revenue?

    Diversify marketing beyond Google Ads by focusing on content marketing for SEO and AI discoverability. Explore B2B gifting partnerships with organizations and consider direct mail campaigns to increase brand recall during critical moments of need.

  • How can The History List Store increase its customer base and reduce customer acquisition costs?

    Given a low CAC, increase advertising spend on platforms like Facebook. Experiment with TikTok for historical narratives and collaborate with smaller history podcasts for targeted advertising. Continuously share compelling historical stories to attract and engage a wider audience.

  • What is Miguel McKelvie's advice for founders regarding their weaknesses?

    McKelvie advises founders to be more critical of their weaknesses and areas they tend to avoid. He suggests confronting these less enjoyable aspects of business management, rather than delegating them away, to ensure comprehensive responsibility and growth.

Show Notes

Today’s callers: Jane in Minnesota wants to scale her artful pants brand while staying true to her locally-made mission. Then Melissa in New Mexico wonders how to respond to diminishing returns on digital advertising for her grief care packages. And Lee in Massachusetts hopes to decrease customer acquisition costs for his history merch brand ahead of America’s 250th anniversary.

Plus, Miguel reflects on his WeWork experience and the similarities he sees in today’s AI-dominated tech industry. Miguel’s latest venture, Unbound, seeks to disrupt healthcare in the United Kingdom.

Thank you to the founders of Copa Threads, Good Grief, and The History List Store for being a part of our show.


If you’d like to be featured on a future Advice Line episode, leave us a one-minute message that tells us about your business and a specific question you’d like answered. Send a voice memo to hibt@id.wondery.com or call 1-800-433-1298.

And be sure to listen to WeWork’s founding story as told by Miguel in 2017, as well as his second appearance on the show in 2022.


This episode was produced by Sam Paulson with music by Ramtin Arablouei. It was edited by John Isabella. Our audio engineer was Kwesi Lee.

You can follow HIBT on X & Instagram and sign up for Guy’s free newsletter at guyraz.com or on Substack.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Advice Line with Miguel McKelvey of WeWork

Advice Line with Miguel McKelvey of WeWork