Podcast Summary: How I Built This with Guy Raz

Episode: Advice Line with Miguel McKelvey of WeWork

Original Airdate: March 5, 2026
Host: Guy Raz
Guest Advisor: Miguel McKelvey, Co-Founder of WeWork

Overview

In this "Advice Line" episode, Guy Raz is joined by Miguel McKelvey, co-founder of WeWork, to take live calls from three entrepreneurs seeking guidance on scaling, marketing, and customer acquisition. Throughout the episode, McKelvey shares personal reflections on WeWork’s journey, lessons learned, and specific, actionable advice tailored to each caller’s business dilemma. The episode is rich in practical insights on brand storytelling, marketing innovations, and navigating rapid growth while staying true to core values.

Key Discussion Points & Insights

1. Reflections on WeWork & Entrepreneurship (04:06–09:25)

• McKelvey on Looking Back:
  Reflects that the WeWork experience is still a huge part of his life, provides ongoing lessons, both good and painful, and continues to bring him fulfillment when hearing from former employees.
  • Quote:
    “Every one of those experiences is an opportunity to grow from and learn – about myself, about how to treat other people, about how to do business in the right way.” (05:40, Miguel McKelvey)
• AI Bubble Parallels:
  Draws a comparison between the WeWork/tech startup bubble and the current excitement (and anxiety) around AI company valuations.
  • Quote:
    “With AI...because they can do so much and it’s not yet clear exactly how to monetize them, it is a bit confusing... It’s like the dot com boom – everyone’s super excited, but no one’s exactly sure if the business models are sound.” (07:43, Miguel McKelvey)
• Mentorship Role:
  McKelvey values advice-giving and mentoring, finding fulfillment in helping others see challenges differently.

2. Caller 1: Jane Barthel, Founder of Coppa Threads (09:59–20:39)

The Business

A small-batch, high-quality women’s pants brand bridging the comfort of scrubs with the sophistication of trousers, manufactured in Minneapolis with U.S.-sourced fabrics.

Challenge

How to scale and build demand while maintaining local, ethical production (and the resulting high price point).

Discussion Highlights

• Brand Storytelling as Differentiator:
  Emphasize the “why” behind the product’s price and values. Clearly communicate the story of local manufacturing, artisanal process, and handmade quality on every channel—not just once, but repeatedly.
  • Quote:
    “You gotta do a better job at explaining why. ... Go to your website: nothing that you’ve told us is here. ... Now I need to know why I’m paying $295.” (16:31, Guy Raz)
  • Quote:
    “You need to be on Instagram telling your personal story and why you care... And then also have the story of the people making it and the story of where the fabric comes from.” (17:54, Miguel McKelvey)
• Leverage User-Generated Content:
  Showcase real customers (“ambassadors”) wearing the unique pants; encourage them to share on their own social channels.
  • Quote:
    “When a woman is standing with three others and her pants compared to theirs – you’re like, those are some great pants.” (18:55, Miguel McKelvey)
• Grassroots Local Marketing:
  Suggests “seeding” pants with local restaurant servers or coffee shop baristas to drive organic word of mouth.
• Stay True to Brand:
  Don’t dilute the uniqueness by chasing black/neutral pants requests—lean into the artful, colorful identity.

Timestamps

• Storytelling & values: 16:31–19:10
• UGC/ambassadors: 18:00–19:10
• Local marketing: 19:11–19:44

3. Caller 2: Melissa Jensky, Co-Founder of Good Grief (23:31–36:15)

The Business

Online care package company for “life’s twists and turns” (from loss to illness to mental health), featuring curated, practical products and supportive services.

Challenge

Growth plateaued at ~$200k per year; difficulty breaking through with paid digital marketing due to intent and emotional context; seeking new channels and strategies.

Discussion Highlights

• Content and SEO as Core Strategy:
  Create highly targeted, situation-specific landing pages and content for every grief/loss scenario imaginable—both for SEO and for visibility in new AI-driven search experiences.
  • Quote:
    “Having a webpage for literally every single web search you can imagine that someone might make in one of these scenarios would be really smart...If [they] go to AI to ask that question, they're going to find you as well.” (27:54–28:35, Miguel McKelvey)
• Social/Video Content:
  Short TikTok and YouTube videos answering “what do I send someone who...?” kind of questions; meet audiences in their moments of need.
• B2B Partnerships:
  Collaborate with hospices, funeral homes, HR departments, and local organizations for employee gifting or direct referral.
  • Quote:
    “It would seem to me that, and it sounds like you're trying to [do] that channel, that B2B gifting channel–working with HR teams could really be game changer.” (30:53, Guy Raz)
• Experiment with Direct Mail:
  Establish physical brand presence for top-of-mind recall when the need arises.
  • Quote:
    "...It's almost like that thing you want to have on the refrigerator for when that time comes..." (31:18, Miguel McKelvey)
• Problem-Solution Messaging:
  Frame the offering as the solution for those who want to help but “don’t know what to say or do” (i.e., “We are your solution”).
  • Quote:
    “What you want to telegraph is your problem is you don’t know how to help, and we are your solution.” (34:09, Guy Raz)

Timestamps

• Content/SEO advice: 27:54–29:20
• B2B discussion: 29:48–31:04
• Direct mail/recall: 31:12–32:23
• Messaging: 34:09–

4. Caller 3: Lee Wright, Founder of The History List Store (36:58–46:43)

The Business

E-commerce for history lovers: original T-shirts, hats, jewelry, and rare antiques—all designed by the team and made in the USA, rooted in the original “History List” content site.

Challenge

How to leverage the upcoming 250th anniversary of America’s founding to grow the customer base and reduce customer acquisition costs (currently ~$20 CAC, $80 average order value).

Discussion Highlights

• Cost Analysis:
  McKelvey calls out that Lee’s current CAC is quite low given the order value and margin, suggesting scaling ad spend could be a strong, immediate next step.
  • Quote:
    “$20 per customer? ... I would love to acquire customers for $20. That sounds great.” (39:57, Miguel McKelvey)
• Expansion Via Content Marketing:
  Lean into storytelling across channels—especially TikTok and Instagram—even if target audiences skew older, since social platforms' age demographics shift over time.
  • Quote:
    “People love to learn through TikTok. You might need to go post a TikTok a day with a cool historical narrative, and people will start gravitating directly to you.” (41:44, Miguel McKelvey)
• Niche Podcast Collaborations:
  Consider both advertising and co-branded merch partnerships with history podcasts, particularly mid-sized to niche shows.
  • Quote:
    “Some of them probably don't have merch. Maybe you can be a merch person for them.” (43:30, Guy Raz)
• Newsletter & Email:
  Lee’s high open rates (50%) are a major strength—suggests leveraging newsletter further for launches, pre-sales, and retention.
• Broaden Appeal Beyond “History Nerds”:
  Experiment with content that might pull in more casual fans—obscure but accessible facts, behind-the-scenes product stories, etc.

Timestamps

• CAC/margin discussion: 39:48–41:44
• TikTok/social strategy: 41:44–42:35
• Podcast/collab suggestions: 43:30–44:57

Notable Quotes & Memorable Moments

• McKelvey’s fundamental advice to his younger entrepreneurial self:
  “Be more critical about the things that I was bad at, to think more critically about things I avoided. ... You have to be responsible for everything when you’re a founder.” (47:14, Miguel McKelvey)
• On instant execution:
  “If I do all this stuff and come back tomorrow, it'll seem like we were planning it for weeks in advance.” (49:00, Miguel McKelvey, describing early WeWork hustle)
• On finding core customer connection:
  “When people say to me, ‘When are you going to make black pants?’ I say, ‘Well, go to Banana Republic. I’m not making black pants.’” (14:37, Jane Barthel)

Episode Structure & Key Segments

• 04:06-09:25: Miguel’s post-WeWork reflection & AI bubble insights
• 09:59-20:39: Caller 1: Coppa Threads (Jane Barthel)
• 23:31-36:15: Caller 2: Good Grief (Melissa Jensky)
• 36:58-46:43: Caller 3: The History List Store (Lee Wright)
• 47:14-48:18: McKelvey’s advice to his younger self

Tone & Language

The tone is supportive, practical, and conversational, with Guy and Miguel interjecting personal anecdotes and humor, reinforcing a “master class” feel for founders at any stage.

Takeaways

1. Storytelling and clear articulation of your “why” is especially crucial for premium, ethical, or niche brands.
2. SEO and AI-driven content indexing are essential frontiers for businesses addressing specific emotional needs.
3. Experiment broadly with content and channels—even if your audience seems “set”—to find surprise sources of growth.
4. Strong customer retention, community, and owned channels (like newsletters) can be levers for sustainable growth.
5. Entrepreneurs benefit by confronting their weaknesses rather than outsourcing them completely, especially in early stages.

This summary captures the actionable advice, entrepreneurial wisdom, and engaging dialogue from this episode—providing real-world strategies and inspiration for founders and would-be founders alike.