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Mar 5, 2026 · 44m · how-i-built-this

Advice Line with Miguel McKelvey of WeWork

Miguel McKelvey · 13m spoken Guy Raz · 13m spoken Melissa Jenski · 5m spoken Jane Barthel · 4m spoken Lee Wright · 4m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this episode of 'The Advice Line,' Guy Raz and WeWork co-founder Miguel McKelvey provide strategic mentorship to founders navigating pricing, marketing channels, and customer acquisition. Drawing from McKelvey's extensive entrepreneurial experience, the hosts offer practical frameworks for scaling niche e-commerce businesses through storytelling, SEO, and targeted outreach.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 33.7% of the talking time here. How this is scored →

Guy as informed peer 5.3 Guest teaching 2.2 Guest disagreement 1.3 Guy pushing back 2.7
05100:0015:0030:000:40–3:36 · Guy as informed peer 4/10 Reflections on WeWork's Rise, Fall, and Lessons Learned Guy provides historical context on WeWork's rise and valuation drop while inviting Miguel to reflect on the experience. Miguel responds collaboratively, framing the highs and lows as valuable personal lessons without defensiveness.3:37–6:30 · Guy as informed peer 5/10 Analyzing the AI Startup Bubble and Founder Mentorship Guy asks Miguel to compare the current AI startup bubble to previous valuation frenzies. Miguel articulates key structural differences, pointing out that WeWork addressed tangible physical needs whereas AI business models remain largely unproven.6:31–17:29 · Guy as informed peer 7/10 Caller Jane Barthel on Scaling Ethical Apparel Brand Guy analyzes Jane's business model and compares her pricing dilemma directly to American Giant's domestic manufacturing strategy. He presses her on the fact that her compelling artisan backstory is completely absent from her storefront.17:44–30:46 · Guy as informed peer 6/10 Caller Melissa Jenski on Marketing Channels for Grief Care Melissa discusses the collapse of her Google Ads ROI and challenges in marketing grief packages. Guy and Miguel offer constructive advice spanning AI search engine optimization, direct mailers, and specific problem-solving copy.31:03–41:12 · Guy as informed peer 7/10 Caller Lee Wright on Growing The History List Store Lee asks how to lower his customer acquisition cost, but Miguel points out his $20 CAC on an $80 order is already strong. When Lee dismisses podcast advertising based on rejection from a major show, Guy firmly pushes back, urging him to target smaller, niche history shows.41:14–43:35 · Guy as informed peer 3/10 Founder Blind Spots and Archival WeWork Origin Story Guy asks Miguel to share advice for his younger self, prompting a candid confession about avoiding financial oversight early in his career. The segment closes with a brief archival clip from Miguel's original interview.0:40–3:36 · Guest teaching 2/10 Reflections on WeWork's Rise, Fall, and Lessons Learned Guy provides historical context on WeWork's rise and valuation drop while inviting Miguel to reflect on the experience. Miguel responds collaboratively, framing the highs and lows as valuable personal lessons without defensiveness.3:37–6:30 · Guest teaching 3/10 Analyzing the AI Startup Bubble and Founder Mentorship Guy asks Miguel to compare the current AI startup bubble to previous valuation frenzies. Miguel articulates key structural differences, pointing out that WeWork addressed tangible physical needs whereas AI business models remain largely unproven.6:31–17:29 · Guest teaching 1/10 Caller Jane Barthel on Scaling Ethical Apparel Brand Guy analyzes Jane's business model and compares her pricing dilemma directly to American Giant's domestic manufacturing strategy. He presses her on the fact that her compelling artisan backstory is completely absent from her storefront.17:44–30:46 · Guest teaching 2/10 Caller Melissa Jenski on Marketing Channels for Grief Care Melissa discusses the collapse of her Google Ads ROI and challenges in marketing grief packages. Guy and Miguel offer constructive advice spanning AI search engine optimization, direct mailers, and specific problem-solving copy.31:03–41:12 · Guest teaching 3/10 Caller Lee Wright on Growing The History List Store Lee asks how to lower his customer acquisition cost, but Miguel points out his $20 CAC on an $80 order is already strong. When Lee dismisses podcast advertising based on rejection from a major show, Guy firmly pushes back, urging him to target smaller, niche history shows.41:14–43:35 · Guest teaching 2/10 Founder Blind Spots and Archival WeWork Origin Story Guy asks Miguel to share advice for his younger self, prompting a candid confession about avoiding financial oversight early in his career. The segment closes with a brief archival clip from Miguel's original interview.0:40–3:36 · Guest disagreement 1/10 Reflections on WeWork's Rise, Fall, and Lessons Learned Guy provides historical context on WeWork's rise and valuation drop while inviting Miguel to reflect on the experience. Miguel responds collaboratively, framing the highs and lows as valuable personal lessons without defensiveness.3:37–6:30 · Guest disagreement 1/10 Analyzing the AI Startup Bubble and Founder Mentorship Guy asks Miguel to compare the current AI startup bubble to previous valuation frenzies. Miguel articulates key structural differences, pointing out that WeWork addressed tangible physical needs whereas AI business models remain largely unproven.6:31–17:29 · Guest disagreement 2/10 Caller Jane Barthel on Scaling Ethical Apparel Brand Guy analyzes Jane's business model and compares her pricing dilemma directly to American Giant's domestic manufacturing strategy. He presses her on the fact that her compelling artisan backstory is completely absent from her storefront.17:44–30:46 · Guest disagreement 1/10 Caller Melissa Jenski on Marketing Channels for Grief Care Melissa discusses the collapse of her Google Ads ROI and challenges in marketing grief packages. Guy and Miguel offer constructive advice spanning AI search engine optimization, direct mailers, and specific problem-solving copy.31:03–41:12 · Guest disagreement 2/10 Caller Lee Wright on Growing The History List Store Lee asks how to lower his customer acquisition cost, but Miguel points out his $20 CAC on an $80 order is already strong. When Lee dismisses podcast advertising based on rejection from a major show, Guy firmly pushes back, urging him to target smaller, niche history shows.41:14–43:35 · Guest disagreement 1/10 Founder Blind Spots and Archival WeWork Origin Story Guy asks Miguel to share advice for his younger self, prompting a candid confession about avoiding financial oversight early in his career. The segment closes with a brief archival clip from Miguel's original interview.0:40–3:36 · Guy pushing back 1/10 Reflections on WeWork's Rise, Fall, and Lessons Learned Guy provides historical context on WeWork's rise and valuation drop while inviting Miguel to reflect on the experience. Miguel responds collaboratively, framing the highs and lows as valuable personal lessons without defensiveness.3:37–6:30 · Guy pushing back 1/10 Analyzing the AI Startup Bubble and Founder Mentorship Guy asks Miguel to compare the current AI startup bubble to previous valuation frenzies. Miguel articulates key structural differences, pointing out that WeWork addressed tangible physical needs whereas AI business models remain largely unproven.6:31–17:29 · Guy pushing back 4/10 Caller Jane Barthel on Scaling Ethical Apparel Brand Guy analyzes Jane's business model and compares her pricing dilemma directly to American Giant's domestic manufacturing strategy. He presses her on the fact that her compelling artisan backstory is completely absent from her storefront.17:44–30:46 · Guy pushing back 3/10 Caller Melissa Jenski on Marketing Channels for Grief Care Melissa discusses the collapse of her Google Ads ROI and challenges in marketing grief packages. Guy and Miguel offer constructive advice spanning AI search engine optimization, direct mailers, and specific problem-solving copy.31:03–41:12 · Guy pushing back 6/10 Caller Lee Wright on Growing The History List Store Lee asks how to lower his customer acquisition cost, but Miguel points out his $20 CAC on an $80 order is already strong. When Lee dismisses podcast advertising based on rejection from a major show, Guy firmly pushes back, urging him to target smaller, niche history shows.41:14–43:35 · Guy pushing back 1/10 Founder Blind Spots and Archival WeWork Origin Story Guy asks Miguel to share advice for his younger self, prompting a candid confession about avoiding financial oversight early in his career. The segment closes with a brief archival clip from Miguel's original interview.

speaking balance: gold is Guy, purple is the guest (3 minute bins)

0:00 · Guy 69.6% · guest 30.4%0:00 · Guy 69.6% · guest 30.4%3:00 · Guy 28.7% · guest 71.3%3:00 · Guy 28.7% · guest 71.3%6:00 · Guy 25.9% · guest 74.1%6:00 · Guy 25.9% · guest 74.1%9:00 · Guy 15% · guest 85%9:00 · Guy 15% · guest 85%12:00 · Guy 55.4% · guest 44.6%12:00 · Guy 55.4% · guest 44.6%15:00 · Guy 40.3% · guest 59.7%15:00 · Guy 40.3% · guest 59.7%18:00 · Guy 10.8% · guest 89.2%18:00 · Guy 10.8% · guest 89.2%21:00 · Guy 15.7% · guest 84.3%21:00 · Guy 15.7% · guest 84.3%24:00 · Guy 24.1% · guest 75.9%24:00 · Guy 24.1% · guest 75.9%27:00 · Guy 37.9% · guest 62.1%27:00 · Guy 37.9% · guest 62.1%30:00 · Guy 43.3% · guest 56.7%30:00 · Guy 43.3% · guest 56.7%33:00 · Guy 11.6% · guest 88.4%33:00 · Guy 11.6% · guest 88.4%36:00 · Guy 44.4% · guest 55.6%36:00 · Guy 44.4% · guest 55.6%39:00 · Guy 33.3% · guest 66.7%39:00 · Guy 33.3% · guest 66.7%42:00 · Guy 53% · guest 47%42:00 · Guy 53% · guest 47%
Sharpest disagreement ▶ 11:41 Jane rejects customer demands for conventional designs

Jane emphatically rejects consumer pressure to produce neutral black pants, declaring that customers looking for plain clothing should go to Banana Republic.

 Hardest push from Guy ▶ 38:38 Guy refutes caller's skepticism of podcast marketing

When Lee dismisses podcast advertising because a major network-backed show turned him down, Guy refuses the conclusion and insists he pursue smaller shows with 10,000 listeners.

 Biggest teaching moment ▶ 4:12 Miguel reframes AI valuations versus physical startup eras

Miguel educates Guy on the difference between tangible real-world problem solvers like WeWork and Uber versus AI platforms whose business models and monetization paths remain unsettled.

 Guy holds their own ▶ 13:35 Guy critiques apparel positioning using American Giant benchmark

Guy demonstrates deep business acumen by contrasting Copa Threads' poor website messaging with American Giant's transparent supply-chain storytelling to explain how to justify premium pricing.
the scores for every segment, with the reasoning behind each
ChapterTopicGuy as informed peerGuest teachingGuest disagreementGuy pushing backWhy
Reflections on WeWork's Rise, Fall, and Lessons Learned 4211 Guy provides historical context on WeWork's rise and valuation drop while inviting Miguel to reflect on the experience. Miguel responds collaboratively, framing the highs and lows as valuable personal lessons without defensiveness.
Analyzing the AI Startup Bubble and Founder Mentorship 5311 Guy asks Miguel to compare the current AI startup bubble to previous valuation frenzies. Miguel articulates key structural differences, pointing out that WeWork addressed tangible physical needs whereas AI business models remain largely unproven.
Caller Jane Barthel on Scaling Ethical Apparel Brand 7124 Guy analyzes Jane's business model and compares her pricing dilemma directly to American Giant's domestic manufacturing strategy. He presses her on the fact that her compelling artisan backstory is completely absent from her storefront.
Caller Melissa Jenski on Marketing Channels for Grief Care 6213 Melissa discusses the collapse of her Google Ads ROI and challenges in marketing grief packages. Guy and Miguel offer constructive advice spanning AI search engine optimization, direct mailers, and specific problem-solving copy.
Caller Lee Wright on Growing The History List Store 7326 Lee asks how to lower his customer acquisition cost, but Miguel points out his $20 CAC on an $80 order is already strong. When Lee dismisses podcast advertising based on rejection from a major show, Guy firmly pushes back, urging him to target smaller, niche history shows.
Founder Blind Spots and Archival WeWork Origin Story 3211 Guy asks Miguel to share advice for his younger self, prompting a candid confession about avoiding financial oversight early in his career. The segment closes with a brief archival clip from Miguel's original interview.

Statements from this episode (7)

Assertion Supported
Raz: WeWork still operates around 330 locations worldwide
“WeWork, by the way, still exists today. There are about 330 locations around the world.”
Guy Raz Mar 5, 2026 ▶ 1:39
Opinion
McKelvey: Unclear Monetization Makes AI Valuations Hard to Understand
“The AI applications are so incredibly powerful and amazing, but because they can do so much, and it's not yet clear exactly how to monetize them, it is a bit confusing to understand how will they be evaluated, you know.”
Miguel McKelvey Mar 5, 2026 ▶ 4:36
Opinion
McKelvey: Google offering free AI tools could threaten ChatGPT
“When you have big players who are competing, you know, it can be a race to the bottom, and that's scary, too, because if Google wants to give their AI tools for free, what happens to ChatGPT?”
Miguel McKelvey Mar 5, 2026 ▶ 5:24
Assertion Supported
Raz: WeWork co-founder Miguel McKelvey is part owner of American Giant
“Miguel is an owner of, part owner of a brand called American Giant.”
Guy Raz Mar 5, 2026 ▶ 13:48
Assertion Supported
Jenski: Unmanaged workplace grief costs employers $75B+ annually
“I mean, unmanaged grief in the workplace costs employers, you know, seventy-five billion dollars a year and up.”
Melissa Jenski Mar 5, 2026 ▶ 25:20
Insight
McKelvey: TikTok favors raw, direct storytelling more than Instagram
“And again, I think what you find in the difference between tick tock and Instagram is You know, narrative, like, rough storytelling, real people in front of a camera, that's really on TikTok these days, and it's less so on, on some of these other platforms, …”
Miguel McKelvey Mar 5, 2026 ▶ 36:39
Insight
McKelvey: Founders must stay responsible for business areas they dislike
“Sort of out of sight, out of mind. It's not a great model for entrepreneurship. You know, I think you have to be responsible for everything when you're a founder.”
Miguel McKelvey Mar 5, 2026 ▶ 42:06
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