Famous Failures

Nadya Okamoto is the Executive Director of PERIOD (period.org), an organization she founded at the age of sixteen to provide menstrual hygiene products to those in need. PERIOD is now the largest youth-run NGO in women’s health, and one of the fastest growing in the United States.  In 2017, Nadya ran for office in Cambridge, Massachusetts. Although she did not win, her campaign made historic waves in mobilizing young people both on the ground and at the polls. Nadya’s debut book, Period Power: A Manifesto for the Menstrual Movement, made the Kirkus Reviews list for Best Young Adult Nonfiction of 2018. Earlier this year she made InStyle Magazine’s The Badass 50: Meet the Women Who Are Changing the World list along with Michelle Obama and Ariana Grande. Today Nadya is also the Chief Brand Officer of JUV Consulting, a Generation Z marketing agency based in New York City. Keep in touch with Nadya on Instagram: https://www.instagram.com/nadyaokamoto/ In this episode Nadya and I discuss: Why receiving a lifetime

Christine Carter is a sociologist, columnist and speaker. She’s the author of the books Raising Happiness: 10 Simple Steps for More Joyful Kids and Happier Parents, as well as The Sweet Spot: How to Achieve More by Doing Less. She is also a Senior Fellow at the Greater Good Science Center where she explores the science of happiness and researches how to thrive in our stress-filled, fast-paced modern world. Christine has appeared on the “Oprah Winfrey Show,” the “Dr. Oz Show”, the “TODAY” show, the “Rachael Ray Show,” “The Daily Show with Jon Stewart,” and many others. She has been quoted or featured in The New York Times, the Los Angeles Times, USA Today, and other media outlets. You can subscribe to Christine’s monthly newsletter at christinecarter.com/free-updates/. In the episode, Christine and I discuss: Why Christine began to fantasize about being hospitalized What drove Christine to cancel a keynote speaking engagement at the last minute  Why the opposite of busyness is not laziness How the first indus

Tiago Forte is one of the world’s foremost experts on productivity. He writes and speaks on how knowledge workers can revolutionize their personal effectiveness using technology, and has taught more than 20,000 people around the world through his online courses and live workshops. Tiago’s online course Building a Second Brain has been taken by more than 1,000 people from more than 60 countries. You can learn more about Building a Second Brain at https://www.buildingasecondbrain.com/. In the interview, Tiago and I discuss: How Tiago quit his consulting position to pursue a career as an entrepreneur What you can do to prepare for being an entrepreneur  Why Tiago’s first business venture was a massive success.  How that massive success was followed by a colossal failure and the lessons Tiago learned from that failure How Tiago validated his next business idea, the Building a Second Brain course, before launching it Why showing your failures and vulnerability can make you more appealing Resources mentioned: Ta

This is a special episode of Famous Failures. Instead of doing an interview, I recount the story of the first three failures that SpaceX experienced on the launchpad, which brought the company to the brink of collapse.  You’ll learn how SpaceX leveraged these failures for later success and how you can implement the same strategies in your own life.  The content of the episode is based on the following sources: Tim Fernholz, Rocket Billionaires: Elon Musk, Jeff Bezos, and the New Space Race (2018); Shane Snow, Smartcuts: The Breakthrough Power of Lateral Thinking (2014); Chris Bergin, Falcon I flight – preliminary assessment positive for SpaceX, Spaceflight.com (March 24, 2007) https://www.nasaspaceflight.com/2007/03/falcon-i-flight-preliminary-assessment-positive-for-spacex/; Tim Fernholz, What it took for Elon Musk’s SpaceX to disrupt Boeing, leapfrog NASA, and become a serious space company, QZ (Oct. 21, 2014) https://qz.com/281619/what-it-took-for-elon-musks-spacex-to-disrupt-boeing-leapfrog-nasa-and-bec

Ryan Levesque is the CEO of The ASK Method ® Company, and the #1 national best-selling author of Ask: The Counterintuitive Online Method to Discover Exactly What Your Customers Want to Buy, which was named by Inc. as the #1 Marketing Book of the Year. Ryan’s work has been featured in the Wall Street Journal, USA Today, Forbes, and Entrepreneur and over 250,000 entrepreneurs subscribe to his email newsletter offering business advice. His latest book, Choose, helps readers avoid making the single biggest mistake when starting a business and guides people through answering the all important question: What type of business should you start? You can get a free copy of Choose (just pay S&H) plus over $200 in bonuses (including the audiobook) by visiting http://choosethebook.com/famousfailures. This isn’t an affiliate link—if you choose to buy Ryan’s book, I don’t make a dime. In the interview, Ryan and I discuss: How Ryan quit his dream job at AIG Insurance to pursue a career as an entrepreneur Why people are

Khe Hy is the founder of RadReads, which is a community of 20,000 professionals seeking to reexamine their relationship to money, ambition, and ultimately themselves. Khe has been called Oprah for Millennials by CNN and the Wall Street Guru by Bloomberg. He spent the first fifteen years of his career in the financial services industry researching hedge fund investments. He was one of the youngest Managing Directors at BlackRock where he oversaw the New York Research Team. You can sign up for Khe’s newsletter, RadReads, at https://radreads.co/. In the episode, Khe and I discuss: Why Khe did the unthinkable and quit his job at a Wall Street investment firm without a plan How Khe coped with the self-doubt and fear of failure in leaving a prestigious job and strike out on his own What advice Khe would give to people contemplating a similar career transition How he grew his newsletter, RadReads, from 0 to 16,000 subscribers How you can stop caring about what other people think What the scarcity mindset is and wh

Tali Sharot is a professor of cognitive neuroscience and a leading expert on the neural basis of emotion, decision making and optimism. She has been featured in numerous media outlets,including The New York Times, Time magazine, The Washington Post, CNN, BBC, and more. Her TED talk on the optimism bias was viewed over 2 million times. Her latest book, The Influential Mind: What the Brain Reveals About Our Power to Change Others, tackles the neuroscience behind influence -- what we so often get wrong about it, how we can learn to influence others, and how to understand when we are being influenced. In the interview, Tali and I discuss: How our brains are wired to look on the bright side, and why that tendency can both help and hurt us. Why stress can diminish our bias toward optimism How we can remain optimistic in the face of failure or fear of failure Why a failure in Tali’s own life ended up giving her the idea for her research on the optimism bias Why facts and data don’t tend to change minds once we for

SUSAN CAIN is the author of Quiet: The Secret Strengths of Introverts, and Quiet: The Power of Introverts in A World That Can’t Stop Talking, which has been translated into 40 languages, is in its seventh year on the New York Times best seller list, and was named the #1 best book of the year by Fast Company magazine, which also named Susan one of its Most Creative People in Business. Susan’s writing has appeared in The New York Times, The Atlantic, The Wall Street Journal, and many other publications. Her record-smashing TED talk has been viewed over 20 million times and was named by Bill Gates one of his all-time favorite talks. You can join Susan’s newsletter at this link, and follow her on Twitter, Facebook, and LinkedIn. In the interview, Susan and I discuss: Why Susan left a high-powered career as a Wall Street attorney to become a writer What advice she has for others who are contemplating a career transition How she decided to write a book about introversion Why all literary agents, except one, Susan

Rob Walker is an author and journalist covering design, technology, business, the arts, and other subjects. He writes the Human Resource column for Lifehacker, and has contributed to The New York Times, Bloomberg Businessweek, The Atlantic, TheNewYorker.com, and many others. He is on the faculty of the Products of Design program at the School of Visual Arts. His new book is called The Art of Noticing: 131 Ways to Spark Creativity, Find Inspiration, and Discover Joy in the Everyday. If you live in New York City, you can attend free event on May 7th where Rob will discuss his book (details here). You can sign up for the Art of Noticing newsletter at this link and follow Rob on Twitter. In the interview, Rob and I discuss: How a broken coffee mug sent Rob on a creative path to launch the Significant Objects project Why a meaningless object purchased on average for $1.50 can sell for $36 on average on eBay if it has a story attached to it Where Rob’s creative ideas come from How Rob bombed a news interview with

Julian Guthrie is an award-winning journalist, New York Times best-selling author, and all around adventurer who loves underdog stories. Her new book, due out April 30, is Alpha Girls: The Women Upstarts Who Took On Silicon Valley's Male Culture and Made the Deals of a Lifetime. Julian has interviewed some of the world's most dynamic leaders and loves improbable stories and contrarian thinkers. You can say hello to Julian on Twitter or on her website. In the interview, Julian and I discuss: What attracts Julian to the stories of underdogs, ordinary people doing extraordinary things How Peter Diamandis, the entrepreneur best known for being the founder and chairman of the X Prize Foundation, was rejected over 150 times in raising funds for the X Prize, yet managed to keep pursuing his goal. The surprising strategy Julian used to get an interview with Larry Ellison, the co-founder and former CEO of Oracle The critical difference between rejection and failure Why infiltrating a system can be the best way to cha

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 ass

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 H

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’

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 c

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

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

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 s

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-domin

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

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 t