Miguel McKelvey, co-founder of WeWork, joins Guy Raz to provide advice to entrepreneurs facing growth and marketing challenges. McKelvey co-founded WeWork with Adam Neumann in 2007, growing it to a $47 billion valuation by 2019 before Neumann's resignation and the company's IPO withdrawal. McKelvey left in 2020 and now focuses on mentoring and advising founders.

Three callers seek guidance on scaling their businesses: Jane Barthell from Copa Threads struggles with high manufacturing costs for locally-made women's pants, Melissa Jensky from Good Grief faces marketing challenges for grief care packages, and Lee Wright from The History List wants to expand his history-themed merchandise business during America's 250th anniversary year.

WeWork's Rise and Fall: Lessons in Entrepreneurship

WeWork grew from a Brooklyn shared office concept in 2007 to a $47 billion valuation by 2019, before Adam Neumann's forced resignation and IPO withdrawal led to Miguel's departure in 2020.

Miguel reflects on WeWork's impact: 'I'll run into a former WeWork employee who will share how WeWork changed their life... we did something really powerful and it touched a lot of people' - Miguel.

Comparing current AI valuations to WeWork's era, Miguel notes that WeWork solved tangible problems like Uber or Airbnb, while AI applications face unclear monetization despite incredible power.

Copa Threads: Scaling Local Manufacturing

Jane Barthell's Copa Threads generates $15,000 in revenue since launching June 2023, selling $295 women's pants manufactured in Northeast Minneapolis using Florida-sourced canvas.

The pants originated from deconstructed scrubs: 'I deconstructed a pair of scrubs and started making pants just for fun... I would have friends, family, even strangers saying, Oh my God, I love your pants' - Jane.

Miguel emphasizes storytelling: 'You need to be on Instagram telling your personal story and why you care about the product and the way it's made... giving your why will be what really translates to people.'

The recommendation focuses on visibility: gift pants to restaurant servers and coffee shop workers because 'they really jump off the page... the more they're in public, people will say, hey, where are those pants from?' - Miguel.

Good Grief: Breaking Through Marketing Plateaus

Melissa Jensky's Good Grief maintains $200,000 annual revenue for three years but declined 7% recently, selling care packages for life challenges including loss, illness, and mental health struggles.

The business emerged from personal experience: 'When I was 29, I was diagnosed with rheumatoid arthritis... I experienced infertility and a miscarriage... we're not super great at the tough stuff' - Melissa.

Good Grief collaborated with author Erica Sinner on Pets Are Family to launch a custom pet loss care package, demonstrating successful partnerships with grief-focused content creators.

Miguel suggests content-first marketing: 'Having a web page for literally every single web search you can imagine that someone might make in one of these scenarios would be really smart.'

The B2B opportunity remains untapped: 'Unmanaged grief in the workplace costs employers $75 billion a year' but getting 'a foot in the door' with HR teams proves challenging - Melissa.

The History List: Capitalizing on America's 250th Anniversary

Lee Wright's History List achieved $750,000 revenue with 50% margins and $20 customer acquisition cost, selling history-themed merchandise and selected antiques through direct-to-consumer channels.

The business evolved from content to commerce: started as 'a content site for information about events' in 2016 with a History Nerd t-shirt, now offering 'hundreds of SKUs covering a wide range of historical topics.'

Miguel questions the CAC concern: 'I would love to acquire customers for 20 bucks. That sounds great' with $80 average order value creating strong unit economics.

The recommendation emphasizes podcast partnerships: 'Contact some of these history podcasts... see if you can make bespoke things for them that would drive their audience to your site.'

Newsletter performance validates audience engagement: 'more than 50% open rate' mailing every Saturday with new merchandise and Thursday with rare finds - Lee.

Founder Advice: Confronting Weaknesses

Miguel's key lesson for founders: 'Be more critical about the things that I was bad at, to think more critically about things that I avoided.'

He warns against delegation without oversight: 'As soon as I had an opportunity to hire a CFO and never think about money again... that sort of out of sight, out of mind, it's not a great model for entrepreneurship.'

The fundamental principle: 'You have to be responsible for everything when you're a founder... go into the things that you don't like as much as you do the things that you love' - Miguel.