How I Built This with Guy Raz

Advice Line with Miguel McKelvey of WeWork

March 5, 2026

Key Takeaways Copied to clipboard!

  • Founders should critically examine and engage with the aspects of their business they dislike or avoid, as complete delegation can be detrimental. 
  • For niche, high-quality, or artisanal products, scaling requires aggressively communicating the 'why' behind the high price point to build demand. 
  • Businesses facing marketing plateaus, especially in highly situational markets like grief support, should prioritize content creation optimized for both traditional SEO and emerging AI discovery tools. 

Segments

Miguel McKelvey Reflects on WeWork
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(00:05:02)
  • Key Takeaway: Entrepreneurial experiences, including painful ones, offer continuous opportunities for personal and business growth.
  • Summary: Miguel McKelvey views his WeWork experience, including the hard times, as a source of ongoing lessons about self and business conduct. He finds fulfillment in hearing how WeWork impacted former employees, even years after his departure. Engaging with past pain is considered productive for future endeavors.
AI Valuations vs. Real-World Business
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(00:06:56)
  • Key Takeaway: AI valuations are potentially confusing because, unlike tangible businesses like WeWork, clear monetization models are still emerging, drawing parallels to the dot-com boom.
  • Summary: WeWork’s success was rooted in solving tangible, real-world needs like workspace, which made its high valuation easier to see. AI applications, while powerful, present valuation confusion because their monetization strategies are less clear. This uncertainty mirrors the excitement and unsound business models seen during the early dot-com era.
Scaling Local, High-Cost Brand
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(00:09:51)
  • Key Takeaway: For high-cost, locally-made artisanal brands, scaling requires aggressively communicating the unique story and ‘why’ behind the product to justify the premium price point.
  • Summary: Jane Barthell’s Copa Threads produces high-quality, locally-made pants at a $295 price point, limiting rapid, cheap growth. Miguel McKelvey advises doubling down on storytelling—highlighting the local manufacturing and artisanal nature—to attract customers who value those attributes. Getting the product seen publicly, perhaps through local gifting to servers or baristas, can drive organic awareness.
Marketing Strategy for Grief Care Packages
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(00:21:57)
  • Key Takeaway: Grief-focused businesses must prioritize content marketing optimized for search and AI discovery to capture users seeking immediate, specific guidance during difficult moments.
  • Summary: Good Grief, which sells care packages for various losses, struggles to break past $200,000 in revenue due to diminishing returns on Google Ads. Miguel suggests creating extensive, targeted content pages answering specific search queries (e.g., ‘what to do after a miscarriage’) to capture intent-based traffic from both search engines and AI assistants. Exploring B2B gifting channels, like HR departments, represents a significant, high-value growth opportunity.
Reducing Customer Acquisition Cost
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(00:35:23)
  • Key Takeaway: A blended Customer Acquisition Cost (CAC) of $20 for an $80 Average Order Value (AOV) with a 50% margin suggests increasing ad spend is viable, alongside exploring niche podcast advertising.
  • Summary: Lee Wright’s History List store has a favorable CAC of $20 against an $80 AOV and 50% margin, suggesting current advertising efforts are efficient. Miguel recommends increasing spend on existing successful channels like Facebook, while also experimenting with TikTok for narrative content. Targeting smaller, niche history podcasts for advertising or merchandise partnerships could effectively reach the older, dedicated audience.
Advice for Past Self
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(00:45:16)
  • Key Takeaway: Founders must be more critical of the business aspects they avoid or are bad at, rather than immediately delegating tasks like financial oversight.
  • Summary: Miguel McKelvey advises his past self to critically engage with areas he disliked, such as money management, instead of quickly hiring a CFO and ignoring it. Complete avoidance of challenging areas is not a sustainable model for entrepreneurship. Founders must maintain responsibility for all facets of the business, even those they find less motivating.