Hey everyone,

This week on the Tim Ferriss Show, Tim sits down with Rich Barton, the serial entrepreneur and tech visionary behind giants like Expedia, Zillow, and Glassdoor. This is a fascinating dive into the mindset of someone who has repeatedly disrupted massive industries, often by challenging conventional wisdom and empowering consumers with data.

Rich shares the inside stories of spinning Expedia out of Microsoft (against the initial wishes of some), the “aha!” moment that led to Zillow (making home values transparent), and the thinking behind Glassdoor (bringing salary and workplace data into the open). They discuss the importance of taking “big swings,” fostering innovation within large companies, the nuances of leadership, building great teams, and Rich’s core philosophies on business and life – including his framework for deciding which opportunities to pursue (Is it local? Is it fun? Is it lucrative?).

Beyond the business strategy, they also touch on personal habits, longevity theories, Rich’s experiences living in Italy, and even his favorite books (spoiler: mostly fiction!).

Here are the detailed key insights and takeaways:

1. The Genesis of Big Ideas: Zillow & Expedia

• Zillow’s Origin: Came from Rich’s frustration while house hunting post-Expedia sale. He couldn’t easily access home price information online, despite the data existing. The core idea: make real estate data transparent and empower consumers, creating a digital marketplace. The “Zestimate” (real-time estimated home value) was the killer feature, a “provocation” that got everyone talking.
• Expedia Spin-Out: Started as a small project within Microsoft (initially focused on travel guides on CD-ROM!). Rich pitched spinning it out as an independent company, primarily as an HR strategy to retain entrepreneurial talent who might otherwise leave the large corporation. It was a way to keep innovators engaged by letting them build something new. Steve Ballmer greenlit it as a “talent retention pitch.”

2. Building & Scaling: Lessons Learned

• Taking Big Swings: Brad Chase (Rich’s first boss at Microsoft) instilled the value of taking calculated risks on big ideas and not punishing failure if the effort was sound.
• Protecting Innovators: Mainline corporate culture often rejects disruptive ideas (“foreign bodies”). Leadership needs to actively hire, cultivate, protect, and invest in innovators.
• Team Building: Surround yourself with great people who care about the mission. Hire for passion and alignment. Reference checks are often flawed; focus on observing passion for interests during interviews.
• Delegation & Letting Go: Rich describes himself as a “delegator.” A key leadership development technique is for senior leaders to truly disconnect (like a 2-week vacation with zero connectivity) to force their teams to step up and make decisions, revealing future leaders. Secure leaders let go; insecure ones make themselves indispensable.
• Spouses as Investors: The hardest “investors” to convince when spinning out Expedia weren’t VCs, but the spouses of the employees who had to sign off on leaving stable Microsoft jobs.

3. Provocation Marketing & Finding Your Angle

• Create Emotional Resonance: Build features or take stances that you know people will feel strongly about (positively or negatively). This sparks conversation and builds brand awareness organically (e.g., Zestimate, Glassdoor salary transparency, AO rating attorneys).
• Give to Get: Glassdoor’s model required users to share their own salary/review to access the broader dataset. This built the initial database.
• Meet an Unmet Need: Identify a “big obvious problem” where information is opaque or consumer power is lacking (travel booking, real estate data, salary info, legal services).
• Big Pond, Good Fisherman: Focus on large markets (“big ponds”) where even a small share is significant, and ensure you have the right team (“good fisherman”) to execute.

4. Naming Philosophy: Make it Stick

• Avoid Literal: Don’t just name your travel site “hotels.com.” While easy to explain, it lacks ownable brand equity.
• The Hard Way is Better: Invented words (Zillow, Expedia) are harder initially (you have to define them) but ultimately ownable and more memorable.
• Rules for Invented Names:
  • Use Rare Letters: Z, X, Q jump off the page/screen.
  • Fewer Syllables: Two is the sweet spot (Expedia was maybe too long).
  • Good Dog Name Test: Can you easily call for it? (e.g., “Zillow!”)
  • Verbable: Can it become a verb? (“Let’s Zillow the house.”)
  • Positive Evocation: Should feel good or hint at the benefit (Expedia = expedition + speed).

5. On Personal Habits & Mindset

• Morning Routine: Up early (around 6:30 AM), coffee, checks news (CNBC for business, avoids depressing general news), sifts email, gets brain “on,” uses a Venom heating/vibrating back device, then workouts.
• Longevity: Skeptical of overly complex supplement regimens or pushing the body too hard against its natural limits. Believes basic health pillars (diet, exercise, sleep, stress management, purpose, connection) are key. Favors consistency over extreme measures.
• Hobbies & Balance: Painting (via Procreate on iPad), family time, travel, skiing, road biking. Values integrating work and life rather than strict separation. Moved family to Florence, Italy for a year after selling Expedia.
• Fiction as Escape: Reads primarily fiction, especially sci-fi and magical realism, as an essential way to relax his “monkey brain” from the constant operational focus of business. Recommends Ted Chiang, Mark Helprin, Neal Stephenson.
• Billboard Message: From the movie Bowfinger: “Even though I feel like I might ignite, I probably won’t.” Or, simply: “Don’t Panic.” A call for calm and perspective amidst perceived chaos.

Final Thought:

Rich Barton offers a masterclass in identifying huge opportunities hidden in plain sight, often by looking at established industries through a consumer-empowerment lens. His journey underscores the power of intellectual curiosity, calculated risk-taking, building strong teams, and the crucial role of provocation in capturing attention and driving change. His emphasis on balancing intense work with deep engagement in family, health, and personal interests provides a compelling model for sustainable success.

Find Rich Barton: While less active on traditional social media, you can find interviews and talks online. He recommends checking out works by Bill Gurley and Benchmark Capital for venture insights.

Until next time,
The Podcast Notes Team