Important Life Lessons from 5 of the World’s Top Performers

In episode 100 of the Masters of Scale Podcast, LinkedIn co-founder Reid Hoffman and executive producer June Cohen gathered five of their favourite guests for an open and honest round table discussion about their entrepreneurial journeys.

The Highlights

1. The Toughest Entrepreneurship Challenges – loneliness, self-doubt, and failure.

2. Most expensive lessons learned – holding onto people for too long, not trusting yourself and your instincts, not hiring senior people early enough.

3. Previous episode reflections – building a great team, coming up with an outstanding product, cultivating a personal brand, and building a network.

4. Effective storytelling tips – make it human by using emotions, tell it in real-time, know your audience, be vulnerable, and tell it passionately.

The Knights Of The Round Table

Tyra Banks

Tyra is the founder and CEO of SMiZE cream and Bankable Productions, the creator and executive producer of America’s next top model.

Brian Chesky
Brian Chesky is the co-founder and CEO of Airbnb, an online marketplace that connects those seeking to rent out their homes with those looking for accommodation in the area.

Sallie Krawcheck is the co-founder and CEO of Ellevest, a Robo-advisor run by women and marketed primarily for women.

Franklin Leonard is the founder of The Blacklist and film executive. The Blacklist is a platform for film and TV writers to showcase their screenplays for industry members and get their work evaluated by professional readers.

Angela Ahrendts is the former Apple head of retail and former CEO of Blueberry.

Best Quotes

 • “Build something a hundred people love. Not something a million people like.”Brian Chesky

 • “To do anything great, you need to build trust in your team.”Angela Ahrendts

 • “Startups can come and go. So do the employers. The thing that remains constant is you. How you solve problems, learn from mistakes, build networks and relationships, and what you stand for matters most.”Tyra Banks

 • “It’s not about what I can get from it. It’s about what I can give, and it will come back later.”Sallie Krawcheck

 •  “I don’t know if there’s any other way to tell a story effectively. And that’s true in entrepreneurship, movies, or if you’re sitting in a bar next to somebody, you gotta make them feel it.”Franklin Leonard

Top Lessons from the Guests

The Toughest Entrepreneur Challenges

Brian Chesky: The more successful you get, the lonelier life becomes. Loneliness and isolation are the most challenging parts of entrepreneurship.

Franklin Leonard: The crippling self-doubt that you’re doing it wrong. Therapy is a valuable survival tool.

Sallie Krawcheck: When you’re successful, making money and creating impact, you win together. When you fail, you’re alone and stuck with that failure as the team moves on to something else. This happened during the pandemic, when founders and business owners were left alone to figure out how to survive, with little support.

Most expensive lessons ever learned.

Sallie Krawcheck: When you start a business, everyone tells you it’s too hard when it isn’t going well. Nobody tells you it’s going to be hard if things are going well. She’s also learned to let people go who aren’t performing earlier. Holding on to them for too long was an expensive mistake.

Franklin Leonard & Angela Ahrendts: You need to trust yourself. Keep using your instincts if you have an idea, vision, or dream.

Brain Chesky: Try and hire senior leaders fast. Listen and take advice from them, but also listen to yourself and trust your instincts.

Actionable Advice

Brian Chesky On Building A Great Product

 •  Airbnb’s model of entrepreneurship: Ensure people have good stories to share about your product. It can be tough, but if you spend time with your customers and understand their needs, you can create the perfect experience for those people.

“Build something a hundred people love, not something a million people like.”

 •  Often, the challenge for entrepreneurs is scaling, which is your enemy. Many entrepreneurs are obsessed with scaling. But the biggest gift you have is a lack of scale.

 •  Embrace being small, make something perfect because that’s what will fuel your company in the future.

Angela Ahrendts On Building a Team Around Trust

“To do anything great, you need to build trust in your team.”

When the time comes to make a critical decision, a skilled team can show you the correct answer.

Inspire your team with a guiding mission, connect face to face, give them a reason to buy in, think big, then watch them take ownership of the mission.

Everyone feels empowered if you build a team around trust.

Tyra Banks on cultivating a personal brand

“Startups can come and go. So do the employers. The thing that remains constant is you. How you solve problems, learn from mistakes, build networks and relationships, and what you stand for matter the most.”

When things aren’t going well, it’s okay to take a break, find space and think deeply about your product. Know when it’s time to shift, especially when the world is changing. You can’t be doing the same things you were doing.

Sallie Krawcheck on building your network

 •  Building a network early enough can be helpful. Sallie’s approach to networking is to give people as much value as possible.

“It’s not about what I can get from it. It’s about what I can give, and it will come back later.”

 •  Men learn early on that business is a team sport. They fund each other, invest together, bring each other on the deals, boards, and talk each other up.

 •  Most women, however, picked up that business is an individual sport. But women coming together to support women is the key to success.

Franklin Leonard on the business of making movies

If you can make something that people love, and it’s easy to access, like Netflix, you have a winner.

Story Telling

 •  Franklin: The most compelling stories centre on a person, make them human, and shows their emotions. You can do this by recounting adventures.

“I don’t know if there’s any other way to tell a story effectively. And that’s true in entrepreneurship, movies, or if you’re sitting in a bar next to somebody, you gotta make them feel it.”

 •  Tyra Banks: A remarkable story should take people through the journey because they imagine things happen. Since it’s hard to show people the journey, the most effective way is to work out loud and tell real-time stories.

 •  Brian Chesky: The way to tell your story as a founder is passionately all the time in a way that everyone can relate. Don’t just tell them what happened, but also why it happened.

“Every time you tell a story, tell it as if it’s the first time.”

 •  Angela Ahrendts: Being vulnerable and sharing with your team that you don’t always know what to do and that you need their help unites the team the best.

 •  Sallie Krawcheck: Knowing who your audience is and tailoring your story to them.

Relevant Links

Guests
Tyra Banks (@tyrabanks) • Instagram photos and videos
Brian Chesky (@bchesky) / Twitter
Sallie Krawcheck | LinkedIn
Franklin Leonard (@franklinjleonard) • Instagram photos and videos
Angela Ahrendts | LinkedIn

Episodes

Tyra Banks on Masters of Scale with Reid Hoffman
Brian Chesky on Masters of Scale with Reid Hoffman
Sallie Krawcheck on Masters of Scale with Reid Hoffman
The Black List’s Franklin Leonard on Masters of Scale with Reid Hoffman
Angela Ahrendts on Masters of Scale with Reid Hoffman

Smize Cream | Super Premium Ice Cream Shop | Frozen Custard
Airbnb: Vacation Rentals, Cabins, Beach Houses, Unique Homes & Experiences
The Black List: Where filmmakers & writers meet (blcklst.com)
Ellevest: A financial company by women for women.
Apple

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