Photo by CanvaFemale entrepreneurs often face unique barriers, such as limited funding and gender bias, which can amplify the impact of setbacks. Yet, many turn these "fails" into fuel for future success. Below is a curated list of 10 notable examples of business failures or major challenges experienced by prominent women founders. These aren't just collapses—they're turning points that highlight resilience. I've drawn from well-documented cases to focus on high-profile instances, including startup shutdowns, leadership exits, and rejected ventures.
# | Entrepreneur | Venture/Failure | Key Details | Lesson Learned |
1 | Kathryn Minshew | Pretty Young Professionals (PYP) | Launched in 2010 as a career site for young women; shut down after just six months due to poor user engagement and funding struggles. | Pivot quickly—use feedback to iterate. Minshew relaunched as The Muse, a thriving job platform valued at over $100M. |
2 | Christina Wallace | Quincy Apparel | Founded in 2012 with Harvard backing; collapsed in 2015 after supply chain issues, cash flow problems, and team burnout, leaving $200K in debt. | Balance passion with operations. Wallace co-authored a Harvard Business School case study on the failure and now leads growth at Bionic. |
3 | Arianna Huffington | First two books (biographies of Picasso and Maria Callas) | Rejected by 36 publishers in the 1970s-80s; seen as too niche and risky for a young immigrant writer. | Rejection builds grit. She later founded The Huffington Post, sold for $315M in 2011, and Thrive Global. |
4 | Sara Blakely | Early Spanx prototypes | Cut feet off pantyhose for demos in the late 1990s; pitched to Neiman Marcus and got rejected repeatedly before landing a meeting. | Persistence pays—cold-call and demo relentlessly. Spanx hit a $1B valuation; Blakely became the youngest self-made female billionaire. |
5 | Audrey Gelman | The Wing | Co-founded in 2017 as women-only co-working spaces; Gelman stepped down as CEO in 2020 amid racism allegations, toxic culture claims, and pandemic layoffs, leading to its sale. | Culture must match the mission. Gelman reflected on prioritizing growth over inclusivity; the brand was acquired but never fully recovered. |
6 | Tyler Haney | Outdoor Voices | Founded in 2014 for activewear; Haney ousted in 2020 after burning $70M in VC, executive turnover, and reports of favoritism and cash mismanagement. | Scale sustainably. Haney stepped back but later advised on fitness ventures; the company stabilized under new leadership. |
7 | Steph Korey | Away (luggage startup) | Co-founded in 2015; stepped down as CEO in 2019 after employee backlash over "toxic" management, including public shaming via Slack. | Lead with empathy, not intensity. Korey focused on personal growth; Away hit $1.4B valuation despite the scandal. |
8 | Leandra Medine | Man Repeller | Started in 2010 as a fashion blog; shut down in 2020 after 200+ staffers alleged a culture of fat-shaming and size bias in a company memo. | Authenticity requires accountability. Medine apologized and pivoted to consulting; the brand's influence waned but inspired media reforms. |
9 | Christene Barberich | Refinery29 | Co-founded in 2004 as a women's media site; Barberich resigned in 2020 following accusations of racial insensitivity in editorial content and leadership. | Diversity isn't optional—embed it early. Refinery29 was sold for $400M in 2020; Barberich shifted to advocacy work. |
10 | Jen Gotch | Ban.do | Co-founded in 2013 for stationery and lifestyle; Gotch resigned in 2020 amid employee claims of racism and lack of inclusivity during BLM protests. | Values must guide decisions. Gotch became a mental health advocate; the company was acquired by Hallmark but faced ongoing scrutiny. |
Top 10 Habits That Almost Guarantee Failure as a Female Entrepreneur
(Things many of the women in the previous list did at some point—and later fixed)
If you want to join the 90% of startups that crash and burn (especially as a woman already fighting an uphill funding battle), religiously practice these habits:
# | Toxic Habit | Why It Destroys You (Especially as a Woman Founder) |
1 | Trying to be the “perfect” founder instead of the real one | Investors and media punish women twice as hard for any perceived weakness. Pretending you have no flaws makes you brittle and inauthentic—when cracks show, trust collapses (see The Wing, Man Repeller). |
2 | Raising just enough money to survive, not to win | Women already get ~2% of VC. Taking tiny “safe” rounds keeps you in constant fundraising mode, burning runway and credibility. Quincy Apparel and Outdoor Voices bled out this way. |
3 | Hiring friends and people who only say “yes” | Loyalty over competence + no pushback = blind spots and groupthink. Multiple 2020 resignations (Refinery29, Ban.do, Away) started with echo-chamber teams. |
4 | Obsessing over optics and “girlboss” branding instead of unit economics | Aesthetic co-working spaces, viral merch, and glossy photos feel good but don’t pay servers. The Wing raised $100M+ on vibe and still imploded. |
5 | Ignoring culture until it explodes on Twitter | Women founders are held to higher moral standards. One racism or toxicity allegation in 2020 was enough to force CEO exits at The Wing, Refinery29, Away, Outdoor Voices, Man Repeller, etc. |
6 | Scaling the team before scaling revenue | Hiring 100+ people on hope is a classic trap. Outdoor Voices went from 5 → 200 employees while still pre-profit—cash incinerator. |
7 | Believing “if you build it, they will come” without ruthless customer validation | Pretty Young Professional and early Spanx both started with assumptions that almost killed them. Women get fewer chances to be wrong. |
8 | Avoiding conflict and hard conversations | “Nice” founders delay firing underperformers, confronting co-founders, or saying no to investors. The fallout is usually public and brutal (Away’s Slack scandals). |
9 | Tying your entire identity to the company | When it fails (statistically likely), you crash personally. Many of the founders above needed therapy or full sabbaticals after stepping down. |
10 | Never asking for help because it feels like weakness | Male founders brag; female founders often whisper their struggles. Result: isolation, burnout, and missing the exact mentor or investor who could have saved them. |
Do all ten of these consistently and you’ll fail faster than the market average—and with a lot more public shaming.
The good news? Every woman from the first list eventually dropped most of these habits… and either rebuilt stronger companies or became wildly successful advisors, authors, or investors.
Avoid these ten like the plague and your odds of surviving past year five go up dramatically.
Top 10 Critical Mistakes These Female Founders Fixed — And How That Correction Led to Massive Success
Here are the exact pivots and corrections made by many of the women from the “failure” lists — turning near-death experiences into billion-dollar companies, nine-figure exits, or legendary personal brands.
# | Founder | Original Fatal Mistake | How She Corrected It | Result |
1 | Sara Blakely (Spanx) | Selling only through cold calls to department stores; almost went bankrupt waiting for one “yes” | Took a week off, drove to Charlotte herself, did in-store demos wearing the product, forced Neiman Marcus buyer to try it in the bathroom | First order from Neiman Marcus → Oprah’s “Favorite Things” → $1B+ company, youngest self-made female billionaire |
2 | Kathryn Minshew (The Muse) | Built Pretty Young Professionals as a content site with no clear revenue model; died in 6 months | Talked to 500+ job seekers, realized they wanted real career advice + jobs → pivoted to a recruiting platform with paid company profiles | The Muse now valued at >$200M, profitable, 75M+ users |
3 | Arianna Huffington (HuffPost → Thrive Global) | After 36 book rejections, almost gave up writing entirely | Moved to New York with almost no money, started networking aggressively, wrote freelance columns, built a public persona first | Huffington Post sold to AOL for $315M (2011); Thrive Global valued at ~$800M |
4 | Melanie Perkins (Canva) | Spent 3 years pitching 100+ VCs for her first startup (Fusion Books) and got rejected by all of them | Simplified the deck to 10 slides, flew to San Francisco with $300, cold-emailed Bill Tai, got intro to Lars Rasmussen (Google Maps co-founder) | Canva now worth $40B+ (2025), Melanie is Australia’s richest woman under 40 |
5 | Whitney Wolfe Herd (Bumble) | Left Tinder after harassment lawsuit; almost walked away from dating apps forever | Flipped the script: made women message first → solved safety + empowerment in one move | Took Bumble public in 2021 at $13B valuation; youngest female founder to ever IPO (age 31) |
6 | Katrina Lake (Stitch Fix) | First version was manual (she personally shopped for clients); almost impossible to scale | Built proprietary algorithm + data science team instead of relying on stylists’ taste alone | Stitch Fix IPO 2017 ($3B+), still the only female-founder-led public tech company for years |
7 | Emily Weiss (Glossier) | Into The Gloss blog had millions of readers but zero revenue for years | Listened to comment section begging for products → launched 4 SKUs with almost no marketing budget (just community) | Glossier hit $1.8B valuation at peak; sold minority stake to private equity in 2023 |
8 | Payal Kadakia (ClassPass) | Original product (Classivity) was a search engine for classes — nobody used it | Pivoted to monthly subscription pass after watching users hoard class packs → solved the “I paid but didn’t go” problem | ClassPass raised $500M+, sold for >$1B equivalent in 2023 |
9 | Anne Wojcicki (23andMe) | Launched $999 DNA kit in 2007 — sales were terrible, FDA banned it in 2013 | Dropped price to $99, got FDA approval for health reports, partnered with GSK for drug discovery | 23andMe went public via SPAC (peak $6B), now profitable on therapeutics pipeline |
10 | Julia Hartz (Eventbrite) | Started as a side project while both founders had day jobs; almost sold for $20M in 2009 | Turned down the offer, raised proper VC, built marketplace instead of just ticketing tool | Eventbrite IPO 2018 ($2.9B valuation); Julia is one of the few female co-founders to ring the NYSE bell |
The Pattern That Repeats in All 10 Stories
They listened to real customer pain instead of their original vision.
They simplified ruthlessly (one channel, one product, one insight).
They asked for help aggressively after years of going it alone.
They changed the business model until cash flow made sense (subscription, marketplace, lower price, etc.).
Do what they did after the mistake — not what they did during the mistake — and you dramatically increase your odds of building something that lasts.
The Biggest Financial Losses by Female Entrepreneurs: Theranos and Beyond
Female entrepreneurs face systemic barriers in funding, but when they secure big investments, the stakes—and potential losses—are enormous. The most catastrophic example is Elizabeth Holmes' Theranos, which evaporated over $900 million in investor capital through fraud and hype, wiping out $9 billion in paper valuation. Below, I've ranked the top 5 documented cases based on total funding raised (a proxy for money lost, as these ventures collapsed without meaningful returns). These draw from high-profile failures where women were primary founders or leaders, emphasizing the human and economic toll.
Rank | Entrepreneur & Venture | Funding Raised (Lost) | What Happened | Key Impact & Lesson |
1 | Elizabeth Holmes Theranos (2003–2018) | $900M+ (valued at $9B peak) | Promised revolutionary finger-prick blood tests; tech was fake, using third-party machines. Exposed by WSJ in 2015, SEC charged fraud in 2018. Holmes was convicted in 2022, sentenced to 11+ years. | Investors like Murdoch lost $125M each; patients got false diagnoses. Lesson: Hype without validation erodes trust—especially in health tech, where lives are at stake. Holmes' story stigmatized women founders in STEM. |
2 | Meg Whitman (Co-Founder & CEO) Quibi (2018–2020) | $1.75B (net loss ~$1.4B after $350M returned) | Short-form mobile video app launched amid COVID; ignored TikTok, poor marketing, no desktop access. Shut down after 6 months, 1.7M subscribers. | Hollywood backers (Disney, Warner) lost big; Whitman invested $10.5M personally. Lesson: Market timing and adaptability matter—legacy execs can't always pivot fast in consumer tech. |
3 | Audrey Gelman The Wing (2016–2022) | $118M (near-total loss) (valued at $365M peak) | Women-only co-working spaces; scandals over racism, toxic culture, underpaid BIPOC staff. Pandemic closed locations; sold to IWG in 2021, shut down 2022. | Backers like Sequoia lost most; Gelman resigned amid protests. Lesson: Mission-driven brands must align culture with values—growth can't trump inclusivity. |
4 | Tyler Haney Outdoor Voices (2014–present, but ousted 2020) | $70M+ burned pre-profit (company stabilized post-ouster) | Athleisure brand; rapid scaling led to cash burn, favoritism claims. Haney ousted; company nearly collapsed. | VCs like Forerunner Ventures wrote off much; Haney lost control. Lesson: Sustainable scaling over hype—women founders face extra scrutiny on "likability" in leadership. |
5 | Christina Wallace Quincy Apparel (2012–2015) | ~$1M+ (debt: $200K) | Harvard-backed women's workwear; supply chain woes, burnout. Shut down in debt. | Personal financial ruin; Wallace turned it into a HBS case study. Lesson: Operations must match passion—early validation prevents small losses from snowballing. |
Broader Insights
Total Ecosystem Loss: These cases alone represent ~$3B+ vaporized, amplifying gender biases: A 2025 NBER study shows women post-failure raise 53% less VC than men from the same ventures. Investors penalize women-led failures more harshly, reducing future funding by $31M on average over 5 years.
Patterns: Overfunding without product-market fit (Theranos, Quibi), culture mismatches (The Wing), and scaling pitfalls dominate. Yet, survivors like Wallace pivoted to success (e.g., advising at Scale Investors).
Silver Lining: Failures fuel resilience—Holmes aside (due to fraud), most here rebounded: Whitman to boards, Gelman to hospitality, Haney to fitness advising.
These aren't just losses; they're cautionary tales for the 90% startup failure rate, hitting women harder amid the $2% VC funding gap. Aspiring founders: Prioritize ethics, validation, and diverse teams to beat the odds.
CONCLUSION
These stories underscore a broader truth: Women-led startups fail at similar rates to men-led ones (around 90%), but women face steeper penalties post-failure, raising 53% less capital for future ventures due to investor bias. Despite this, these entrepreneurs demonstrate that failure is often a "steppingstone," as Huffington puts it. For aspiring founders, the takeaway? Build networks, prioritize culture, and view setbacks as data—not defeat. If you're navigating your own challenges, resources like Goldman Sachs' 10,000 Women program can help.
