Stories the Ecosystem Isn’t Built to Hear (Yet)

We say we want founders to be vulnerable. But try telling a room full of investors you’re burnt out. Or that you haven’t been the same since your loved one passed away. 

Watch how fast the energy shifts.

The truth is, we’ve built an ecosystem that praises openness in theory and punishes it in practice. Where “real talk” is fine for a podcast, but not for a boardroom. It’s about time we had a real real talk. There are reasons why founders don’t share the struggle — and the silence affects not just them but their teams and businesses, too.

We realized this when a founder, in an off-script moment, told our Global Chief Marketing Officer Silvia Cavalcanti, a former founder herself, that sharing struggles openly while scaling felt “like bleeding in a shark tank.” That raw honesty lingered.

For the past year, Silvia has been sitting down with entrepreneurs to hold space for the emotional realities behind the scenes, often for the first time. The result is Endeavor Untold, a series of stories that we’re not built to hear, but that we can’t ignore. 

Here’s what we believe the ecosystem is getting wrong. (P.S. This might get uncomfortable.)

1. Founders can’t show “weakness”

Paulo Veras signed the closing of his company’s Series B round from the hospital. He was battling leukemia, but insisted on working relentlessly. His two co-founders visited once or twice a week. Skype meetings would happen between treatment sessions. A few years later, that company — 99 — became Brazil’s first unicorn and was later acquired by China’s DiDi.

Now, 10 years after his diagnosis, Paulo speaks openly about one of the most challenging periods in his life. Before that, however, there wasn’t much space for vulnerability. His focus was on beating cancer, of course, but also on keeping the business afloat.

Boards still want performance updates rather than personal realities. Pitch meetings still prioritize confidence over candor. Tech media often profiles “overnight success” instead of quiet resilience.

Tony Jamous, founder of Oyster, a global employment platform currently valued at $1.2B, faced this dilemma as he processed the trauma of growing up in a war zone while not letting anyone in on how that affected him as an entrepreneur. 

Upon moving to a new country, Tony had no safety net, no fallback, and no community. So he poured everything into succeeding, both for himself and his family back home.

Tony used his addiction to work as a shield knowing that, in this environment, emotional honesty is risky. The safer bet is silence, even if it consumes you.

2. Founders think the problem is theirs alone

When Javier Vallaure sold his company, Allpago, to PPRO in YEAR one of the largest fintech exits in Latin America, things should’ve felt like a win. But the stress of the merger collided with something much more personal: the birth of his second child, and the illness (and eventual passing) of his father.

Javier’s health declined. He grew irritable, disconnected. He no longer recognized the person he’d become. The diagnosis, once he allowed himself to ask for help, was depression.

This kind of cycle, believe it or not, is common. Though founders you know might not share the details with you, they all have feelings of inadequacy. 

Endeavor Brazil’s research on mental health shows that 85% of entrepreneurs reported experiencing anxiety. Nearly 40% faced burnout. One in five had panic attacks. Overall, 91.5% know another entrepreneur who has faced mental health challenges on their journey.

The longer we treat this as an individual issue instead of a systemic one, the longer the system will keep breaking its own talent. That applies not only to founders but also to the teams they lead.

When one founder speaks up, another somewhere else exhales, reminded they’re allowed to be human. When their teams become aware of the burden their leader is carrying, they might just step in and pick up the load — or at the very least, understand why things seem different.

Our hope is that, by making vulnerability part of the narrative, not the footnote, we’ll start to shift what “strong leadership” looks like. 

3. Founders don’t know who to call

Every founder’s path is shaped by unseen variables: geography, team dynamics, cultural context, personal history, all wrapped up by the unique experience that is entrepreneurship. 

That’s why advice from the outside often misses the mark. And why sharing the struggle with a therapist, spouse, or best friend — although always helpful — may not be enough to see the way through if they haven’t been in similar shoes.

Peer circles, like those we build through Endeavor Outliers, work differently. They don’t hand out one-size-fits-all answers. They offer lived wisdom, specific to the messiness of the moment, in a trusting environment. No stakeholders or conflicts of interest, just people who get it. 

What we found out, however, is that more seasoned entrepreneurs adopt the practice of sharing personal challenges way more than less seasoned ones. Perhaps that partly explains why founders with more than 10 years of experience also have a less stressed routine compared to those with less than five years of experience, according to Endeavor Brazil’s report.

The bottom line is: founders will go through pain sooner or later, and their performance will be affected by it, whether we talk about it or not. Speaking up is not just better for them, it’s also better for business.

While we can’t change the ecosystem’s attitudes overnight, we can help rewrite the narrative of mental health in entrepreneurship. 

Endeavor Untold is one way we are helping to reveal the gritty, uncomfortable truths that are always part of the journey, even if they stay hidden until founders are safely out of the shark tank. 

This isn’t a call for founders to speak louder. It’s a call for the rest of us to start dismantling the expectation that entrepreneurs must mask these emotional realities to earn respect or validation — to listen differently, reward differently, and create a safer and more resilient environment for companies to grow in.

The seventh and last story of this season of Untold will be published next week. Keep your eyes peeled and, in the meantime, check out all the other ones here.