what we can learn from female founders

tennie’s first inspirations

One of the biggest indicators that a girl will pursue entrepreneurship? Exposure to a woman who has started her own business. That’s why these stories are so important, and why we’re dedicating an entire Substack to share some fascinating female founder stories, starting with the first women who showed us that starting a business was possible - even if you didn’t look or act like Mark Zuckerberg.

Whitney Wolfe Herd (Bumble)

Whitney Wolfe Herd built Bumble after leaving a toxic environment at Tinder. Her idea was simple but radical: what if women made the first move in online dating? In an industry where women were often on the receiving end of harassment, she flipped the script. Bumble quickly became more than just a dating app; it was a cultural statement about agency and respect. Whitney took the company public at 31 and is still innovating in the digital dating world today.

why her story matters: I’ve listened to her How I Built This episode more time than I care to admit. Whitney’s story shows what happens when you not only see the gap in the market but then rebuild the system around women’s needs. That’s what’s been missing in professional clothing: for too long, men have had a comfortable uniform while women have had to settle for “good enough.” No more, not if Tennie has anything to say about it.

Sara Blakely (Spanx)

Sara Blakely started Spanx with $5,000 in savings and no outside investment. She spent years refining her idea and convincing a department store buyer to take a chance, and in doing so, reshaped an entire industry – literally. She became the world’s youngest self-made female billionaire at the time, all while keeping her brand rooted in comfort, confidence, and humor. We have no choice but to forgive her for the Sneex design.

why her story matters: It’s easy to feel imposter syndrome when starting a business. I’ve asked myself, “who do I think I am starting a fashion brand after working in finance?” Then I remember Sara’s story. She’s proof that grit, creativity, and mission can be enough to break into any industry.

what controversy teaches us

One of the first pieces we wrote for The Tennie Times talked about the “downfall” of the girlboss. For a while, the persona reigned supreme: ambitious millennial women building big brands and making even bigger headlines. But they were not without controversy. Here’s what the OG girlbosses teach us about operating in the startup world – and in the business world in general.

Sophia Amoruso (Nasty Gal / Girlboss)

The originator of the term “girlboss” herself - Sophia Amoruso grew Nasty Gal from an eBay shop into a fashion empire and later built Girlboss into a cultural platform. But when both ventures faced setbacks, and Nasty Gal ended up filing for bankruptcy, the word “girlboss” itself became shorthand for failure. Instead of letting this define her, Sophia used it to help the next generation of female founders, launching a VC firm and digital entrepreneurship course.

why her story matters: Sophia’s story shows how women are often forced to carry the weight of an entire movement. Male founders fail and move on; women founders fail and become symbols or cautionary tales. I’m glad Sophia was able to rewrite the narrative and use her story to inspire women to try, try again.

Ty Haney (Outdoor Voices)

Ty Haney founded Outdoor Voices in 2013 with the slogan Doing Things and quickly built a brand that embodied playful, everyday activity. After stepping away in 2020 following management struggles, she returned with new ventures — TYB and Joggy — and is now back at Outdoor Voices to revitalize the brand for a new Gen Z demographic.

Haney has been candid about the backlash female leaders face, especially when they are the “face of their brand.” Her response? That building publicly means you’ll face hard moments, but ambition requires resilience. Is “ambition requires resilience” my new mantra?

why her story matters: I decided to put myself out there in my development of Tennie in a way that is fun but, if I’m being honest, feels a bit awkward at times (see above: imposter syndrome). Ty’s journey highlights both the excitement and scrutiny of building in public. Her willingness to keep pushing forward underscores a great lesson for every woman with big goals: pursue your dream boldly and – sure – with a bit of delulu. Nobody’s going to believe in your vision if you don’t.

Audrey Gelman (The Wing)

The Wing launched with huge fanfare as a co-working and community space for women. It promised empowerment and inclusivity, but reports of toxic workplace culture told a different story. By 2022, the company had shut down completely.

why her story matters: The Wing reminds us that branding isn’t enough, and inclusivity can’t just be a marketing message – it has to be built into the foundation of the business itself. I feel like people love to use stories like Audrey’s to mock “women supporting women” as performative, but as we learned in last week’s edition of The Tennie Times, authentic community amongst women is such a valuable asset that shouldn’t be downplayed.

the bigger picture

When we look at these stories together - the wins, the controversies, the hard lessons - one theme emerges: female founders are held to a higher standard and scrutinized in ways their male counterparts simply aren’t. But that doesn’t diminish their impact. It sharpens the reminder that building something real takes authenticity and the courage to lead on your own terms.

At Tennie, that’s what inspires us most. Not the glossy girlboss era or the headlines about failure, but the women who keep showing up, creating solutions, and reshaping industries despite the odds. Because the future of entrepreneurship isn’t about perfection, it’s about persistence. And women aren’t just part of that future. We’re building it.

the next generation: new founders we’re rooting for!

Listening to How I Built This is inspiring, but it’s hindsight, or the polished version of success. What excites me most are the stories still in motion: founders in the early, messy stages, testing ideas and building in real time. These are some of the voices shaping the next era of entrepreneurship.

Lucy Guo (Scale AI, Passes)

Lucy Guo co-founded Scale AI before going on to launch Passes, a platform that helps creators monetize their communities. She’s part of a new wave of Silicon Valley founders rewriting the rules of what’s possible, unapologetically dominating in the tech space where women are unfortunately still very rare.

Sophia Kianni and Phoebe Gates (Phia)

Sophia Kianni and Phoebe Gates – yes, that Gates - recently launched Phia, a venture aimed at making secondhand shopping more accessible. With sustainability top of mind for Gen Z, Phia focuses on curating secondhand fashion in a way that feels elevated rather than like a compromise. Sure, being Bill Gates’s daughter makes raising capital a little easier (Kris Jenner was even an early investor, casual), but money alone can’t create cultural relevance. They also started a podcast called The Burnouts on Alex Cooper’s Unwell network, which I love because, like I said earlier, seeing women in the startup world encourages more women to enter, which may tip the uneven scales in venture funding going to women.