WeWork as a cautionary tragedy

Christina Farr is an investor, startup advisor, and former health-tech journalist. She’s the author of The Storyteller’s Advantage: How Powerful Narratives Make Businesses Thrive and the creator of the Second Opinion newsletter, where she decodes healthcare and technology for leaders.

Most leaders try to move markets with features, roadmaps, and metrics. But the winners often move them with narrative—stories that rally investors, customers, and teams to build the future with them. Christina unpacks how great storytellers create belief that becomes momentum.

You’ll learn a simple framework to make your strategy legible and compelling, how to pick the right plot for your message, and practical ways to craft origin stories, pitch decks, and CEO communications that persuade.

In this episode we cover:

• The SOAP framework: Surprise, Openness, Authenticity, Pathos
• Seven classic plots for business (from David vs. Goliath to Rebirth) and when to use each
• Case studies: PillPack vs. incumbents; Apple’s comeback; Microsoft’s reinvention; WeWork’s cautionary tale
• Fundraising and sales: decks that move capital and customers
• Leading in tense moments: speaking to charged issues without fracturing culture

Episode Timeline:

00:00 – Highlight from today’s episode

01:05 – Introducing Christina + the power of narrative in business

03:05 – “If you really know me…”

04:20 – What is strategy? Story as prognostication

07:10 – Why story beats data alone in pitches, sales, and retention

10:55 – The SOAP framework (Surprise, Openness, Authenticity, Pathos)

18:40 – Engineering surprise; calibrating vulnerability

22:00 – Seven plots leaders can borrow (with modern brand examples)

28:45 – Case study: PillPack’s David vs. Goliath playbook

32:40 – Rebirths and tragedies: Apple, Microsoft, WeWork

36:10 – Origin stories that travel (and ones that don’t)

38:10 – CEO comms on divisive topics, without breaking culture

39:20 – Where to learn more from Christina

Additional Resources:

• Book: The Storyteller’s Advantage — Christina Farr (Basic Venture) -https://basic-venture.com/titles/christina-farr/the-storytellers-advantage/9781541704299/
• Newsletter: Second Opinion - https://secondopinion.media/
• Christina Farr on LinkedIn - https://www.linkedin.com/in/christinafarr/

Thank you to our guest, our executive producer Zach Ness, our editor James Pearce, and the Outthinker team. If you enjoyed this episode, please follow, download, and subscribe. I’m your host, Kaihan Krippendorff—thank you for listening.

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