Overview

In this episode of the Advice Line, WeWork co-founder Miguel McKelvey joins Guy Raz to counsel three entrepreneurs grappling with the tension between values-driven production and sustainable growth. The conversation moves from a neonatologist's artisanal pants brand in Minneapolis to a grief care package company in Santa Fe and a history-themed merchandise business preparing for America's 250th anniversary. Throughout, McKelvey draws on his experience building WeWork from a shared office space to a $47 billion valuation—and its subsequent collapse—to offer grounded advice about storytelling, customer acquisition, and the importance of confronting the parts of business you'd rather ignore. The episode also features McKelvey's reflections on parallels between the WeWork era and today's AI boom, particularly around valuation uncertainty and the challenge of monetizing transformative technology.

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3:33Opening Reflections: WeWork's Legacy and the AI Parallel

Guy Raz introduces Miguel McKelvey by revisiting the arc of WeWork: founded in 2007 when McKelvey, an architect by training, met Adam Neumann in a Brooklyn office space; reaching a $47 billion valuation by 2019; then the failed IPO, Neumann's ouster over mismanagement allegations, and McKelvey's departure in 2020. Raz notes that McKelvey emerged from the WeWork saga with his reputation intact—portrayed favorably in documentaries and dramatizations—and asks how he views the experience with more distance.

McKelvey says he still reflects on it constantly. Speaking to entrepreneurs at an accelerator the night before, he found them intensely curious about both the highs and lows. He describes entrepreneurship as "a roller coaster no matter what scale you're at," and insists that every experience—especially the painful ones—offers a chance to learn about himself, about how to treat others, and about doing business the right way. He still encounters former WeWork employees who share how the company changed their lives, which gives him a feeling of having done something powerful and lasting.

Raz then draws a parallel to the current AI landscape, where valuations have soared in ways reminiscent of WeWork's peak. McKelvey sees a key difference: WeWork solved a tangible, real-world problem—people need workspace—just as Uber solved transportation and Airbnb solved lodging. AI's applications are "incredibly powerful and amazing," he says, but it's not yet clear how to monetize them. He compares the moment to the dot-com boom, where excitement about technology outpaced sound business models. He notes that he uses AI tools constantly but barely pays for them, which feels "a little bit scary"—especially if major players like Google give away AI tools for free, creating a race to the bottom that threatens companies like ChatGPT.

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9:53Caller 1: Jane Barthel and Copa Threads — Scaling an Artisanal Pants Brand

Jane Barthel, a 54-year-old neonatologist from Minneapolis, founded Copa Threads, a women's pants brand built around colorful, printed trousers made from 100% cotton canvas. The idea came from deconstructing a pair of scrubs—the most comfortable pants she knew—and remaking them in fun, funky fabrics. Friends and strangers alike stopped her to ask about the pants, and she launched in June 2025, generating about $15,000 in sales in roughly six months. The pants are manufactured at a woman-owned factory in northeast Minneapolis, with fabric sourced from a Florida mill via a Chicago-based supplier. They retail at $295 per pair.

Jane's question is about scaling while staying true to her values: local manufacturing, high quality, and a commitment to colorful, wearable art. She has no interest in making black or neutral pants—"go to Banana Republic," she says—but she's struggling to find enough customers willing to pay $295 for a pair of pants made in small batches.

McKelvey immediately identifies the core tension: the bottleneck isn't production capacity but customer demand at that price point. He asks where her existing customers came from, and Jane admits most are friends and family, plus a local high-end boutique. Raz jumps in with a pointed observation: Jane's website doesn't tell the story of why the pants cost $295. He contrasts this with American Giant, a brand McKelvey is part-owner of, which makes its story of U.S.-sourced cotton and domestic manufacturing central to every customer interaction. "Nothing that you've told us is here," Raz says. "You don't know it's made in a factory in Minneapolis by a group of women. It's handmade. These are hand-sourced. Now I need to know why I'm paying $295."

McKelvey agrees that storytelling "moves the needle 100%," but emphasizes that it must be repeated constantly—on Instagram, through the founder's personal narrative, through the stories of the people making the pants and where the fabric comes from. He also points to the power of user-generated content: photos of women wearing the pants at music festivals sell the product visually, but the "why" behind the product needs to accompany every image. He suggests a guerrilla marketing tactic: gift pants to servers at local restaurants or baristas at coffee shops, so people see them in the wild and ask where to buy them. Jane says one of her goals is to see a stranger wearing her pants at the grocery store, and McKelvey encourages her to make that happen through visibility and storytelling.

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24:49Caller 2: Melissa Jenski and Good Grief — Navigating Diminishing Returns on Digital Ads

Melissa Jenski co-founded Good Grief in Santa Fe, New Mexico, with her sister Kristen, who is based in the UK. The company sells care packages for life's difficult moments: loss of a loved one, pet loss, infertility, miscarriage, cancer, mental health struggles, breakup, job loss. Each box contains practical, healing-oriented products—books and journals specific to the type of loss, consumables like tea and chocolate, cozy items like socks and sleep masks, and even add-on services like one-on-one grief coaching. The idea came from Melissa's own experiences: diagnosed with rheumatoid arthritis at 29, then infertility and a miscarriage, followed by a family member's spouse dying by suicide. She realized society is "super great at celebrating the good stuff" but falls short when it comes to the tough stuff—people don't know what to say or do.

The business launched in April 2021 and has plateaued at around $200,000 in annual revenue for three years, with a 7% decline in the most recent year. Melissa's primary marketing channel has been Google Ads, which initially delivered strong returns but "completely collapsed" in the summer of 2024. She's now trying to diversify but feels overwhelmed by the number of scenarios her business touches—each type of grief is a different audience, and she has limited time and budget.

McKelvey's first observation is about content. He imagines someone experiencing a difficult moment turning to an AI assistant like Gemini and asking, "This just happened, what do I do?" Good Grief needs to be the answer. He recommends creating a webpage for "literally every single web search you can imagine" related to grief and loss, optimized both for traditional SEO and for AI crawling. The same content should be distributed as TikTok videos, YouTube videos—anywhere people might search for guidance. "You want to be there to help people deal with it," he says.

Raz pushes on a different channel: partnerships. Has Melissa worked with hospices, oncology centers, funeral homes, or HR departments? Melissa says she's done cold outreach to funeral homes and launched a custom care package with author Erica Sinner for pet loss. She's also seen repeat orders from companies like Chewy, Nike, Microsoft, and the Gates Foundation, but can't get a foot in the door with HR teams. McKelvey suggests starting locally in Santa Fe, and Raz notes that unmanaged grief costs employers an estimated $75 billion annually, making the B2B gifting channel a huge opportunity.

McKelvey also raises the challenge of recall: grief care packages are a "back of mind" purchase—people need to remember the brand exists when a crisis hits. He suggests direct mail, like a card that people put on their refrigerator, so when the moment comes, they know where to go. "The more times someone touches a brand, the more likely they are to recall it," he says. "You might need to touch them three, four, or five times." Raz adds that the messaging needs to be direct and problem-solving: "How do you help somebody who just got a horrible diagnosis?"—not just product features, but a clear answer to the customer's unspoken question of how to show support.

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39:01Caller 3: Lee Wright and The History List Store — Lowering Customer Acquisition Costs Ahead of the 250th

Lee Wright runs The History List Store from Marlboro, Massachusetts, near Boston. What began as a content site about historical events evolved into a merchandise business when Lee designed a "history nerd" T-shirt in 2016. The store now sells hundreds of SKUs—T-shirts, hats, pins, jewelry, and even selected antiques like a ship's passport signed by John Tyler or World War posters. The products are designed in-house and nearly everything is made in America. Revenue hit $750,000 last year, with an average order value of $80 and gross margins around 50%. Customer acquisition cost is about $20, primarily through Facebook ads.

Lee's question is how to increase the customer base and drive down acquisition costs, especially with the 250th anniversary of American independence approaching—a major opportunity for a history-themed brand.

McKelvey is initially puzzled: a $20 CAC on an $80 order with 50% margins sounds healthy. "If I was going just on that, I would be saying, just spend more money on more advertising," he says. But he offers several growth ideas. First, TikTok: while Lee's audience skews older, McKelvey argues that age demographics shift, and TikTok's strength is raw, narrative storytelling with real people in front of a camera. Second, podcast advertising: rather than chasing big history podcasts with large ad networks, McKelvey suggests finding smaller shows with dedicated audiences of 10,000 rather than 100,000, where a direct partnership or ad buy is more feasible. Third, creating original content: Lee already has a successful newsletter with a 50%+ open rate, and McKelvey suggests expanding into a podcast where Lee highlights a cool historical fact and connects it to a product the store sells.

Raz adds that the key is expanding the edges of the brand's appeal. The core audience is history enthusiasts, but there's a larger group of people who could be attracted by surprising, accessible, fun historical facts. Lee mentions that their social media manager, who goes by "Dame," already does this effectively—sharing obscure and timely content. McKelvey encourages more experimentation across platforms and formats.

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49:05Final Advice: Confronting What You Avoid

At the end of the episode, Raz asks McKelvey the question he poses to every returning founder: if you could go back to the early days of building WeWork and give yourself one piece of advice, what would it be?

McKelvey's answer is personal and specific. He says he knew early on that he "didn't care about money" as a motivator, so as soon as he could hire a CFO and never think about finances again, he did. But that "out of sight, out of mind" approach, he now believes, was a mistake. "You have to be responsible for everything when you're a founder," he says. His advice to his younger self—and to other entrepreneurs—is to "go into the things that you don't like as much as you do the things that you love." The parts of the business you avoid are often the ones that can sink you, and confronting them directly is essential.

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Conclusion

This episode matters because it captures a recurring tension in entrepreneurship: how to grow without betraying your founding values. Each caller faces a different version of this problem—Jane with her commitment to local manufacturing and high prices, Melissa with a mission-driven product that resists easy marketing, Lee with a niche audience that limits scale. McKelvey's advice is consistently practical and grounded in his own experience, from the power of storytelling to the importance of confronting uncomfortable parts of the business. His reflections on WeWork's rise and fall, and the parallels to today's AI landscape, add a layer of perspective that makes the episode feel less like a tactical clinic and more like a meditation on what it means to build something real in an era of hype.

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Key takeaways

• Storytelling about why a product costs what it does—materials, manufacturing, craftsmanship—is essential for justifying a premium price point, and that story must be repeated across every channel.
• For businesses with situational or "back of mind" demand (like grief care packages), building recall through repeated touchpoints—email, direct mail, content—is critical; customers need to remember the brand exists when the moment arises.
• Content optimized for both traditional SEO and AI crawling is becoming the new front door for customer acquisition; creating pages for every possible search query related to your product can capture demand before it becomes a transaction.
• B2B partnerships, especially with HR departments, represent a significant growth opportunity for businesses addressing workplace pain points like unmanaged grief, which costs employers an estimated $75 billion annually.
• A customer acquisition cost of $20 on an $80 order with 50% margins is healthy; the right response may be to spend more on advertising rather than trying to lower CAC further.
• Experimentation with emerging platforms (TikTok, podcast advertising, original content) is worth the investment even if the core audience skews older, because audience demographics shift over time.
• Founders must confront the parts of the business they dislike or avoid—not just the parts they love—because neglecting critical functions like finance can create blind spots that undermine the entire enterprise.