Whitney Wolfe-Herd: The Power of Making A Radical Bet on Yourself - Sarah Chen
Impact Investing, Impact Washing, Investment, Philanthropy
post-template,post-template-elementor_header_footer,single,single-post,postid-30361,single-format-standard,bridge-core-2.5,exclusive-addons-elementor,,qode_grid_1300,footer_responsive_adv,qode-theme-ver-23.5,qode-theme-bridge,disabled_footer_bottom,elementor-default,elementor-template-full-width,elementor-kit-7,elementor-page elementor-page-30361
Whitney Wolfe-Herd and her son Bobby, pictured at Bumble’s IPO on Feb. 11, 2021. Photo creds: Kristen Kilpatrick


Hours after she became the youngest woman ever to take a company public, Whitney Wolfe Herd blinked back tears. These were not however tears of joy and relief, but frustration at the way her narrative was being told by the media: focused on Whitney’s alleged harassment and toxic relationships at previous company, Tinder where she was credited as the co-founder and VP of Marketing.


And yet of course, these experiences is what led her to building Bumble, a dating app that continues to challenge misogyny in tech, and where notably women in heterosexual relationships “make the first move”. Today, Whitney Wolfe Herd is a recognizable name, then, at 31 years old becoming the youngest female CEO who had taken a company public in America.


To call her career trajectory a “comeback” is an understatement and this is why, Whitney makes first on the list of #BillionDollarMoves we should all be learning from.


This article is part of the #BillionDollarMoves CEO series, which unpacks the mental models, and key leadership strategies of today’s movers & shakers as they navigated crisis, failure and built success.

#Billiondollarmoves dECONSTRUCTED

1. Don’t be afraid to make radical bets, especially on yourself

Despite the less than favorable end in 2014 where she sued Tinder for sexual harassment and began receiving death and rape threats on social media, she decided to bet on her belief that the dating culture was ripe for change. Even when it felt like the world was not ready for it, encouraged by Bumble backer and builder, Andrey Andreev (then, CEO of Badoo, a multi-billion social network in Europe) to do what she’s good at; Whitney created the first women-first, major social platform to embrace behavioral guardrails and content moderation as part of its business model.

Catapulting herself back into the dating space that she was scarred by, and further calling out current bad practices was a radical bet she made when it would perhaps have seemed less contentious to have exited the industry completely and stayed out of the limelight.


2. Success can be built on personal setbacks and challenges

According to TIME’s interviews of Whitney’s friends and family, her clash with Justin Mateen, co-founder of Tinder was not the first abusive relationship she had been in. Whitney’s mother alleges a high school boyfriend threw a watch at Whitney’s head at a family birthday party, while a friend recalls going to that same boyfriend’s house after being told he had threatened Whitney with a gun. Whitney’s drive to change the landscape of dating is deeply rooted in her early trauma and experiences; to create a world where women feel safe connecting with others online and developing healthy relationships. A well-rooted founder’s purpose is one of the key success factors investors take note of and Whitney clearly checks the box.


3. Building and upholding a purpose-driven brand identity


Of course, focusing solely on her story of redemption minimizes Whitney as a strategic leader who built a brand that continues to stand above the crowd in what would have been deemed a red ocean of dating apps. From the consistent nods to the app’s namesake from the reference to the company’s headquarters as “the hive” to the color yellow, which notably strays away from the standard blue (Facebook, Twitter, Skype) or red (Tinder, OkCupid, Pinterest), Bumble’s brand identity is one that consumers can easily recognize. More importantly, is how Whitney continues to bake in the company’s core brand value of inclusivity; taking a rare stand against non-compliant users in what could have otherwise become a PR nightmare. 


At a moment when most tech executives are making excuses for why they should not and can’t be held responsible for the behavior on their platforms, Whitney’s team took this opportunity to address a woman’s “atrocious” experience on Bumble with a man named Connor in an open letter, “Dear Connor”, that said in no uncertain terms that the behavior he showed was unacceptable on Bumble. The letter went viral and had more than 1 billion impressions. #ImWithAshley

Mental models so you can think like Whitney:

We live in an increasingly uncertain world, and in the framing of my Harvard Professors, increasingly filled with adaptive challenges where solutions are not always clear (see chart below, extracted from my notes from Prof Tim O’Brien’s class).


Whitney’s obstacles clearly included “hearts, minds, and deeply held values” and yet, she continues to take these challenges head on; while, yes, clocking out a >$760 million revenue business last year.


Here are three actionable questions you can ask yourself to think like Whitney:

1. Instead of jumping head first into a radical bet, ask yourself, what is a small risk that you can take on yourself to prove out an open question you have? What are the possible outcomes? Challenge your status quo bias.

2. What setbacks and challenges have you experienced in your life that you can turn into an opportunity? Remember that your unique experience could be the very reason why your solution has the strongest value proposition: because of the depth of your understanding of the problem.


3. What is your current brand identity? What is that of your company? Go beyond a self-inquisition and ask your stakeholders/customers/followers/peers. Are they aligned, and if not, how can you better do that?

It’s clear that Whitney Wolfe Herd will remain one of the most notable self-made businesswomen I’ll be watching; even as more challenges lay ahead for her and her business. To follow her lead, we must be open to an uncertain future, drown out the naysayers, and bet on ourselves. How else has Whitney Wolfe Herd inspired you?



This article is part of the #BillionDollarMoves CEO series, which unpacks the mental models, and key leadership strategies of today’s movers & shakers as they navigated crisis, failure and built success. Sign up here – you won’t want to miss the next CEO profile!