Lenny Distilled

Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, TripAdvisor)

November 05, 2023

Featuring: Chip Conley (Founder, Modern Elder Academy; Former Head of Global Hospitality & Strategy, Airbnb)

8 quotes · 8 insights

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Your hardest struggles become your greatest teachings

Your painful life lessons are the raw material for your future wisdom.
Chip ConleyFounder, Modern Elder Academy; Former Head of Global Hospitality & Strategy, Airbnb 01:15:07

Regulated industries demand mastery of details

If we're as big as we're going to be three years from now, I promise you we're going to be regulated. I promise you we're going to be paying occupancy taxes. Let's take some proactive steps.
Chip ConleyFounder, Modern Elder Academy; Former Head of Global Hospitality & Strategy, Airbnb 00:23:51

Clarify decision rights before diving into work

I want you to start the meeting with the following... let's get really clear on what both, what's the intention of this iteration that we're doing on the product? What defines success, and what do I want to get accomplished in this meeting?
Chip ConleyFounder, Modern Elder Academy; Former Head of Global Hospitality & Strategy, Airbnb 19:25

Founder relationships require exceptional trust and alignment

There was a sense that Brian assumed everybody else was going to work at the same pace and duration, and he still has this issue... his point of view is like, 'Hey, we're having a meeting in the office tonight at 10 o'clock, be there.'
Chip ConleyFounder, Modern Elder Academy; Former Head of Global Hospitality & Strategy, Airbnb 14:20

Start with vision and conviction, not customer validation

Chip Conley, former hotelier, joined Airbnb as head of hospitality where tech teams focused on optimizing the website/app as "the product."

Everyone's talking about, 'We got to make the product better. We got to optimize this button, and improve conversion, and product, product, product.' Isn't the product the homes and the apartments?
Chip ConleyFounder, Modern Elder Academy; Former Head of Global Hospitality & Strategy, Airbnb 08:59

Build in public - authenticity beats expertise

Show up with curiosity and a passionate engagement for what you do, and people won't notice your wrinkles as much as they'll notice your energy.
Chip ConleyFounder, Modern Elder Academy; Former Head of Global Hospitality & Strategy, Airbnb 00:31:28

Build for your best users, not edge cases

I just said, 'Listen, let's get some older people who are hosts in here' to see how well they will be versed in managing their listing purely on mobile.
Chip ConleyFounder, Modern Elder Academy; Former Head of Global Hospitality & Strategy, Airbnb 10:18

Wisdom becomes accessible when you're ready for it

Your painful life lessons are the raw material for your future wisdom.
Chip ConleyFounder, Modern Elder Academy; Former Head of Global Hospitality & Strategy, Airbnb 01:15:07

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