Famous Failures

Sahil Lavingia is the founder and CEO of Gumroad, a web platform where creators can sell products directly to consumers with quick, simple links. Sahil was the second-ever employee at Pinterest before starting Gumroad with the goal of making it a billion-dollar company. Gumroad got off to an explosive start, but it eventually imploded. Sahil managed to keep the company afloat and made it independent, healthy, and profitable. Although Gumroad isn’t the billion-dollar company Sahil originally imagined it would be, it has created tremendous value for creators who’ve generated nearly $190 million from selling their creations on the website.

You can say hello to Sahil on Twitter and read his viral article on his failure to build a billion-dollar company at this link.

Sahil and I discuss:

• Why he dropped out of college only after a semester
• What it was like to be the second-ever employee at Pinterest
• The critical difference between one-way and two-way decisions
• Why Silicon Valley is far less risky than people assume
• How he ended up with $8 million in his bank account as a 19-year-old founder of Gumroad
• Why Gumroad eventually imploded after an explosive start
• What it was like for Sahil to navigate this public failure and what advice he would have given himself
• How Sahil finally turned the company around
• Why he believes his definition of success as building a billion-dollar company was flawed from the very beginning
• Why you should start a company if you’re thinking about it.

Julie Zhuo is the Vice President of Product Design at Facebook. As one of Silicon Valley's top product design executives, she leads the teams behind some of the most popular web and mobile services used by billions of people around the world. She writes about technology, design, and leadership on her popular blog The Year of the Looking Glass and in publications like the New York Times and Fast Company.

Her book, The Making of A Manager:What to Do When Everyone Looks to You, was published last week by Penguin.

You can say hello to Julie on Twitter.

In the interview, Julie and I discuss:

• How she became a manager at Facebook when she was just 25 years old
• The most valuable failures she experienced as a manager and what she learned from them
• Three strategies she uses to deal with imposter syndrome
• How managers can create an environment where team members are willing to share their mistakes and failures
• The importance of saying “I don’t know”
• What you should consider in building a support network for yourself
• How to stay in the “discomfort zone”
• Why the best results don’t come from fear

Amy Edmondson is the Novartis Professor of Leadership and Management at the Harvard Business School.  She is best known for her pioneering work on psychological safety and failure. The topic recently gained widespread popular attention after a February 2016 New York Times Magazine article described psychological safety as the key factor in determining team performance at Google.

Her new book, The Fearless Organization: Creating Psychological Safety in the Workplace for Learning, Innovation and Growth (2018), offers a practical guide for organizations serious about success in the modern economy.

In the interview, Amy and I discuss:

• How an advice-seeking letter that Amy sent to the iconic American inventor Buckminster Fuller landed her a job as his chief engineer.
• How Amy went from engineering to becoming a business school professor.
• What psychological safety is, and why it’s crucial to creativity and high performance
• What factors set apart organizations that promote psychological safety from those that don’t
• How corporate leaders can foster an environment where employees are willing to openly share their mistakes and failures
• What we can learn from the organizational causes behind the 2003 Columbia space shuttle disaster, which Amy spent over two years studying
• How teachers can promote psychological safety in the classroom.

Resources mentioned:

• Amy Edmondson, A Fuller Explanation: The Synergetic Geometry of R Buckminster Fuller
• Amy Edmondson, The Fearless Organization: Creating Psychological Safety in the Workplace for Learning, Innovation and Growth
• Building a Psychologically Safe Workplace, TedX

-

Get your FREE copy of my e-book. Text OZAN to 345345 or navigate to weeklycontrarian.com to download a free copy of my e-book, The Contrarian Handbook: 8 Principles for Innovating Your Thinking. Along with your free e-book, you’ll get the Weekly Contrarian — a newsletter that challenges conventional wisdom and changes the way we look at the world (plus access to exclusive content for subscribers only).

Don’t want to miss future episodes? Be sure to subscribe to the podcast and leave a review on iTunes or Google Play.

As always, thanks for listening. 

Rachel Simmons is the author of Enough As She Is: How to Help Girls Move Beyond Impossible Standards of Success to Live Healthy, Happy and Fulfilling Lives, and the New York Times bestsellers Odd Girl Out and The Curse of the Good Girl. As an educator, Rachel teaches girls and women skills to build their resilience, amplify their voices, and own their courage so that they—and their relationships—live with integrity and health.

Rachel was the host of the PBS television special, “A Girl’s Life,” and her writing has appeared in the Washington Post, Atlantic, Slate, and The New York Times. She’s is a regular contributor to Good Morning America and appears often in the national media.

You can follow Rachel’s work at this link and get a copy of her latest book Enough As She Is, just released in paperback, here.

In the interview, Rachel and I discuss:

• Why Rachel dropped out of a prestigious Rhodes Scholarship program to pursue her research
• How women and girls struggle with an acute fear of failure
• How parents can build resilience in their children
• What educators can do in the classroom to help students overcome their fear of failure
• What you can do to stop overthinking after a failure
• How you can exercise your failure muscles to build up your resilience

-

Get your FREE copy of my e-book. Text OZAN to 345345 or navigate to weeklycontrarian.com to download a free copy of my e-book, The Contrarian Handbook: 8 Principles for Innovating Your Thinking. Along with your free e-book, you’ll get the Weekly Contrarian — a newsletter that challenges conventional wisdom and changes the way we look at the world (plus access to exclusive content for subscribers only).

Don’t want to miss future episodes? Be sure to subscribe to the podcast and leave a review on iTunes or Google Play.

As always, thanks for listening. 

Maren Kate Donovan is an entrepreneur and writer. Her first venture-backed startup, Zirtual, grew to over 400 employees before she turned 30, but then, due to the perfect storm of missteps, was forced to shut down overnight. She now uses her unique experiences as Managing Partner at AVRA, a firm dedicated to creating a world where good help isn’t hard to find.

In the show, Maren and I discuss:

• How a haunted cane launched Maren’s entrepreneurial career
• Why she decided to start her own virtual assistant company and how she overcame the mental hurdles in making that leap
• How she grew Zirtual to 400 employees and $1 million/month in revenue
• Why the company failed overnight and the lessons that this public and painful failure taught Maren
• What strategies Maren used in coping with the fallout from the company’s demise
• Why she decided to become a founder again by starting a new company called AVRA Talent Partners
• How Maren used the lessons learned from Zirtual’s failure in starting AVRA

You can sign up for Maren's newsletter, We Love Work, at the bottom of this link and receive all the news that's fit to email, from the world of work.

Resources mentioned:

The ONE Thing: The Surprisingly Simple Truth Behind Extraordinary Results

The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich

-

Get your FREE copy of my e-book. Text OZAN to 345345 or navigate to weeklycontrarian.com to download a free copy of my e-book, The Contrarian Handbook: 8 Principles for Innovating Your Thinking. Along with your free e-book, you’ll get the Weekly Contrarian — a newsletter that challenges conventional wisdom and changes the way we look at the world (plus access to exclusive content for subscribers only).

Don’t want to miss future episodes? Be sure to subscribe to the podcast and leave a review on iTunes or Google Play.

As always, thanks for listening. 

Jennifer Dulski is the head of Facebook Groups, a product used by more than 1 billion people. She has more than fifteen years of experience at successful startups and big-brand Internet companies, including as a business unit leader at Yahoo! and as CEO of The Dealmap, which was acquired by Google in 2011, making Jennifer the first woman to sell a company to Google. Prior to Facebook, Jennifer spent 4 years as president & COO of Change.org, a social impact company that empowers people globally to start and win campaigns for change.

Jennifer’s first book, Purposeful, about how each of us can be movement starters, is a Wall Street Journal Bestseller. You can join the Facebook group for Purposeful at this link to connect with others interested in starting or supporting movements.

In the interview, Jennifer and I discuss:

• How Jennifer dealt with the uncertainty and fear of failure involved with leaving her leadership position at Yahoo! and joining a startup as CEO
• How the startup failed three times, but she refused to go home
• Why she uses a strategy called “icked-tickda” to be less scared of big or unknown things
• Why she deliberately places her in situations that make her nervous or uncomfortable
• How she destigmatized failure at Change.org through a Festival of Failure
• Why sharing your vulnerability is crucial to becoming a movement starter
• How she uses a trick from the movie Rocky to get back on her feet after losing a round or two.

-

Get your FREE copy of my e-book. Text OZAN to 345345 or navigate to weeklycontrarian.com to download a free copy of my e-book, The Contrarian Handbook: 8 Principles for Innovating Your Thinking. Along with your free e-book, you’ll get the Weekly Contrarian — a newsletter that challenges conventional wisdom and changes the way we look at the world (plus access to exclusive content for subscribers only).

Don’t want to miss future episodes? Be sure to subscribe to the podcast and leave a review on iTunes or Google Play.

As always, thanks for listening. 

Selina Tobaccowala is a serial entrepreneur who started coding in her Stanford dorm room in the late 1990s. Selina and her college friend Al Leib co-founded Evite, which was the dominant platform for online invitations. After Ticketmaster acquired Evite, she served as Senior Vice President of Product and Technology at Ticketmaster. She left Ticketmaster to become the President and CTO of SurveyMonkey.

Selina is now back to being a founder. She started Gixo, a live fitness app that aims to improve global health.  Gixo offers professional coaches teaching live classes to people of all fitness levels in all locations, making exercise more accessible in people’s busy lives.

If you sign up for Gixo and input the promo code OZAN, you’ll get a free trial and a discount on the membership. [Note: This is not an affiliate deal. I don’t make a dime from any sign-ups. It’s simply Selina’s generous offer to the audience].

In the interview, Selina and I discuss:

• How Selina literally stumbled upon the idea for Evite when she was in college.
• The three questions her father asked Selina to help her decide whether she should go with the uncertainty of a start-up as opposed to the certainty of salaried job.
• The most valuable failures she experienced in growing Evite
• How Selina and the SurveyMonkey were able to scale the company rapidly
• How businesses can go beyond paying lip service to failure and actually create a company culture where people are willing to fail and share those failures
• Why she decided to go back to being a founder again.

Resources mentioned:

Annie Duke, Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts

-

Get your FREE copy of my e-book. Text OZAN to 345345 or navigate to weeklycontrarian.com to download a free copy of my e-book, The Contrarian Handbook: 8 Principles for Innovating Your Thinking. Along with your free e-book, you’ll get the Weekly Contrarian — a newsletter that challenges conventional wisdom and changes the way we look at the world (plus access to exclusive content for subscribers only).

Don’t want to miss future episodes? Be sure to subscribe to the podcast and leave a review on iTunes or Google Play.

As always, thanks for listening. 

Dina Kaplan is Founder of The Path, which teaches meditation for the modern mind. The Path has taught thousands of people to meditate around the world.

Before founding The Path, Dina was co-founder and COO of the tech start-up Blip. Before Blip, she was an Emmy-award winning TV news reporter for local NBC stations. Prior to reporting, Dina worked as an associate producer for MTV News and at the White House as Director of Research for the Office of the White House Counsel.

Dina was named one of Fortune Magazine’s Most Powerful Women Entrepreneurs and Fast Company’s Most Influential Women of Web 2.0. She has taught classes at Columbia and NYU, and spoken at TEDx, SXSW, the World Economic Forum, among many others.

You can learn more about The Path here and apply to attend Mela, a weekend meditation retreat in Mexico, at this link.

Dina and I discuss:

• The secret that Dina was hiding when it seemed to the rest of the world like she had it all
• The challenges she experienced as a female tech founder in a male-dominated world
• Why she decided to leave her job and travel for over two years in Asia
• How she came upon the idea of starting The Path
• Three strategies you can use to overcome the tendency to people-please
• How you can build more play into your work

Resources Mentioned

The Disease To Please: Curing the People-Pleasing Syndrome by Harriet Braiker.

-

Get your FREE copy of my e-book. Text OZAN to 345345 or navigate to weeklycontrarian.com to download a free copy of my e-book, The Contrarian Handbook: 8 Principles for Innovating Your Thinking. Along with your free e-book, you’ll get the Weekly Contrarian — a newsletter that challenges conventional wisdom and changes the way we look at the world (plus access to exclusive content for subscribers only).

Don’t want to miss future episodes? Be sure to subscribe to the podcast and leave a review on iTunes or Google Play.

As always, thanks for listening. 

Matilda Ho is the founder of Yimishiji, one of China's first online farmers markets to bring organic and local produce to families. She’s also the founder and managing director of Bits x Bites, China’s first accelerator and venture capital fund that invests in purpose-driven startups to shape the future of food.

Before becoming an entrepreneur, Matilda filled leadership roles at IDEO and BCG (The Boston Consulting Group) in both Shanghai and Washington DC. She holds an MBA from the University of Chicago Booth School of Business. She currently serves as an advisor on the board of Shinho, China’s first and largest organic condiment company.

Matilda and I discuss:

• What Matilda learned from working as Taiwan’s first female dove magician
• Why she enjoys jumping into danger and uncertainty
• How she decided to work on organic food in China, a country that’s had an epidemic of food safety issues
• Why finding an early investor for her company was a blessing and a curse
• The questions that she likes to ask in interviewing employees and startups
• How she creates an environment in her companies for encouraging her employees to share their mistakes and failures
• Why being a CEO is a lonely job, and the strategies that Matilda uses to cope with that challenge

Resources mentioned:

• Bits x Bites Application Form

-

Get your FREE copy of my e-book. Text OZAN to 345345 or navigate to weeklycontrarian.com to download a free copy of my e-book, The Contrarian Handbook: 8 Principles for Innovating Your Thinking. Along with your free e-book, you’ll get the Weekly Contrarian — a newsletter that challenges conventional wisdom and changes the way we look at the world (plus access to exclusive content for subscribers only).

Don’t want to miss future episodes? Be sure to subscribe to the podcast and leave a review on iTunes or Google Play.

As always, thanks for listening. 

Erica Ariel Fox is an advisor to CEOs and other senior executives on their leadership challenges. She is the New York Times best-selling author of Winning From Within: A Breakthrough Method for Leading, Living, and Lasting Change, and she's taught at Harvard Law School for most of the last 20 years. Her thought leadership is shared with clients through Mobius Executive Leadership. Her writing has appeared in Harvard Business Review and McKinsey Quarterly. She is also a LinkedIn influencer and a regular contributor to Forbes in the leadership section.

You can follow Erica’s work on her website and on Facebook, where she has over 200,000 followers.

Erica and I discuss:

• Why the most important negotiations you can have in your life are the ones in your own mind
• The biggest negotiation challenge a foreign supreme court justice presented to Erica
• Why a massively successful initiative that Erica led at Harvard Law School was shut down
• How you can go about challenging conventional wisdom in traditional places
• How the stories we tell ourselves get in the way of our full potential
• The strategies you can use to have conversations about other people’s failures.
• Why you must stand in the truth of your failure to learn and grow.

-

Get your FREE copy of my e-book. Text OZAN to 345345 or navigate to weeklycontrarian.com to download a free copy of my e-book, The Contrarian Handbook: 8 Principles for Innovating Your Thinking. Along with your free e-book, you’ll get the Weekly Contrarian — a newsletter that challenges conventional wisdom and changes the way we look at the world (plus access to exclusive content for subscribers only).

Don’t want to miss future episodes? Be sure to subscribe to the podcast and leave a review on iTunes or Google Play.

As always, thanks for listening.