When Being First Costs You Everything

This Women's History Month, three founders are showing us what first-generation leadership actually looks like and what it costs, even if it's the very thing you built.

We often race to be the first, but no one talks about how fragile that position can be -- first to build something from nothing, without a blueprint, without a safety net, and without the quiet assurance that someone who looks like you has done it before and survived.

A few years ago for Harvard Business Review, I wrote about how first-generation leaders are constantly doing two jobs at once: the work itself, and the work of figuring out the work, in real time, without a map and with double the expectations of success.

This Women's History Month, I keep coming back to three women who know exactly what that feels like, but are publicly navigating some of the toughest moments in their entrepreneurial lives this year.

Creator: Andrea Hutchinson | Copyright: Andrea Hutchinson

Fawn Weaver, CEO of Uncle Nearest Premium Whiskey

Uncle Nearest Premium Whiskey is named for Nearest Green, the first known African American master distiller in U.S. history and the man who taught Jack Daniel how to make whiskey.

Fawn Weaver, a self-made entrepreneur who experienced homelessness as a teenager, resurrected a legacy which turned into $1.1 billion valuation according to Forbes in 2024.

In the background of the success, however, her former CFO allegedly overstated inventory, executed $67 million in unauthorized loan drawdowns, concealed vendor payables, and forged stock transfer documents using Weaver's own signature.

When the lender discovered the discrepancies, they filed a $108 million lawsuit and placed Uncle Nearest into federal receivership, stripping Weaver of operational control of the company she built. The court-appointed receiver's own report found no evidence of wrongdoing by Weaver or her team; however Weaver is still fighting to reclaim what she built today.

Pinky Cole, Founder of Slutty Vegan

Pinky Cole, Baltimore-native and the daughter of Jamaican immigrants, watched her first restaurant burn to the ground in 2016.

She came back and built Slutty Vegan into a cultural institution -- a plant-based burger brand so loud and so joyful that by 2023 it was valued at nearly $100 million.

She returned to hands-on leadership in 2024 to find $10 million in corporate overhead, a C-suite that wasn't working, and expansion that had outpaced the cash flow to sustain it.

On February 13, 2025, she lost the company entirely through a state-level restructuring.

On March 28, 2025, she bought it back, renamed the parent entity "Ain't Nobody Coming to See You, Otis" and promised to rebuild on new terms -- slower, leaner, under a franchise model built for sustainability over speed.

This week, she filed for personal bankruptcy, listing $1.4 million in debt and calling herself "unemployed" in the filing.

Anifa Mvuemba, CEO of Hanifa

Anifa Mvuemba built Hanifa from scratch. No fashion school. No investors. No connections -- just 'bootstraps.'

She taught herself to sew from YouTube videos, hand-stitched every order herself until 2018, and in 2020 staged a virtual runway show dedicated to Congo, 3D models floating through space in her designs, streamed live on Instagram -- an innovation that shocked the fashion world during the COVID-19 pandemic.

By 2024, Hanifa had dressed Savannah James for the Met Gala and built a loyal community of Black women who had never before seen their bodies centered in luxury fashion.

Invetiably, a site-wide pre-order sale in November 2025 generated more volume than the brand had ever processed. Manufacturer delays cascaded and orders arrived weeks late causing customers to turn to social media to express their frustration.

Mvuemba was six weeks postpartum when she stepped away from maternity leave to manage the crisis. And this week, Hanifa announced an indefinite pause to reset business operations.

Three different industries. Three different circumstances. One shared truth.

These companies, and their leaders, scaled at the speed that every business publication celebrated them for.

Though the capital structures, the media, and the networks were not built with them and their unique circumstances in mind, first-generation leaders like these women still learn to build the confidence to trust their own instincts though each headline tells them they're wrong. They build the muscle to redefine what success and failure look like when no one before them set the standard. They build the courage to keep going when the cost of being first becomes impossible to ignore.

And increasingly, Black women in these positions aren't waiting for the system to resolve itself. They're building new ones, like becoming the fastest growing group of entrepreneurs despite being pushed out of corporate at record rates.

You can see this change in Fawn Weaver's refusal to quietly accept receivership, fighting in court to reclaim what she built. You can see it in Pinky Cole buying her own company back 43 days after losing it, then immediately reframing the story as a comeback rather than a collapse. You can see it in Anifa Mvuemba choosing, against every capitalist instinct, to stop instead of racing towards infinite market goals and scalability.

Women's History Month, at its best, is both a celebration and an invitation to look closer.

To ask: what are you seeing that I'm not? Am I curious enough to hold the full context -- the 43 days, the alleged fraud, the postpartum nights?

These women and their common threads are one of many lessons, and won't be the last in our lifetimes.

They are a sign of the times. And a turn of the tide.

How we answer and show up for for the next swath of first-generation of leaders is up to us.