While vast inroads have been made toward recognizing the value of women in senior management positions, on boards and within organizations, a considerable imbalance remains. Female leaders’ path to the top takes longer and is stymied by societal expectations, unconscious bias and legacy gender roles.

Sometimes, you have to actually “walk a mile in someone’s shoes” to understand the extent of the problem. Craig Enenstein, CEO of Corridor Capital, LLC, unexpectedly learned that 13 years ago when he joined YPO. 

This unforeseen “walk” would lead him to discover an untapped market of phenomenal talent that would transform not only his business, but his YPO community as well.

A startling inspiration

Soon after Enenstein joined YPO in 2009, he was placed in a forum with, among others, Lizanne Falsetto, CEO, Chairman and Founder of betterland foods™. 

Forum is, to a large degree, YPO’s fulcrum — small groups of members who forge deep, trusting relationships by confidentially sharing their most intimate challenges, goals and dreams. In return, they receive open and honest insights, perspectives and unmitigated support. Forum is widely considered the most valuable aspect of membership. 

So, when Falsetto expressed her frustrations navigating the Draconian ins and outs of selling her company, Enenstein, an institutional private equity investor, offered his help.

“I read her contracts,” he says. “I sat silently in on phone calls. Because she didn’t have any history in the deal world, she was at greater risk of investment firms treating her terribly, taking actions which made her feel disempowered. I helped her see that she held power when it all looked like it was crashing down.” 

Asked to explain who “everyone” was, Enenstein says, “The private equity jerks. Principally men. And with very few exceptions, they’re all men. And I thought, ‘there’s something wrong here.’ I’m going to take this information and make a difference in my business and in my YPO chapter.”

At the time, only 4% of Enenstein’s chapter was female.

Empathy is critical 

Enenstein thought about two integral lessons he’d learned over the years about running a business.

“My first boss in private equity was Michael Milken, who taught me that when everyone’s running out of a burning building, that’s a really interesting time to be in the building entry business,” Enenstein says, then smiles. 

After a pause, he adds, “The Warren Buffett equivalent would be, ‘when people are greedy, be fearful; when people are fearful, be greedy.’ And if you extrapolate those into a very simple version of being contrarian in your thinking, it begins to raise some really interesting questions.”

Those questions include: What if the dearth of bankable companies run by women is a fallacy? What if, as everyone had long stated about YPO, it wasn’t that capable women weren’t out there, everyone was just looking in the wrong place? 

And so Enenstein engaged in open, honest discussions with women in private equity attempting to see the industry through their eyes. What he heard, compelled him to create a platform “that while still horribly imperfect,” he admits, “is kinder and more aligned than any of our traditional male counterparts.” 

What that looks like literally, on a daily basis, takes a page from NLP (neuro-linguistic programming), which suggests that you can connect to someone by mirroring their cues. 

“I have CEOs who need that traditional male, ‘attaboy!’ kind of stuff,” explains Enenstein further. “I have other CEOs who are very sensitive and emotional and my interactions with them are going to mirror who they are to give them what they need. And I built a team that’s similarly empathic.”

Empathy has long been an advisable leadership skill, but in the past few years, has become critical. A 2021 study by Catalyst found that 76% of people who worked with empathic leaders were engaged compared to 32% who experienced less empathy. And when it comes to retention, 57% of white women and 62% of women of color said they were unlikely to leave their companies when they felt respected and valued.

Since 2014, 40% of the Corridor Capital portfolio companies have been women-led. 

“My rhetoric — and this is a phrase you will never hear in my industry from anybody, ever — is that we are servant capital,” says Enenstein. “We’re here to help you unlock your greatest potential through a collaborative, transparent and high-integrity model. Our purpose isn’t to make money. Our purpose is to transform people, companies and ecosystems to become their best. Money is a derivative of these behaviors.”

Prioritizing is key 

When it came to creating greater gender diversity in his YPO community, Enenstein made it clear that if anyone in his chapter wasn’t on board, they were welcome to leave. 

“I know it sounds super simple,” he shares, “but I believe that if you don’t say ‘gender diversity is my no. 1 priority and that you are either on the bus or off the bus,’ you won’t get there.” 

Everyone stayed on the bus, and Enenstein’s next order of business was to comb through every resource possible to find qualified candidates. 

“I was staying up until two or three in the morning on services such as LinkedIn, tracking down potential women, then tracking down every woman they knew, then every woman they knew until I had exhausted the entire database,” he recalls. “I scoured newspaper articles, magazine articles, organizations, nonprofits, I looked to see who was getting awards, teamed up with a woman in YPO in Northern California and asked for her HR databases.”

In the end, he found 100 women. And less than a year later, his chapter rose from 4% to more than 20% female. 

“It wasn’t like we were horrible people doing bad stuff before the initiative, we just weren’t aware and when you’re not aware, you can’t make a change.”

Innovation = success

In 2020,Fortune 500 companies with at least three female directors saw returns on invested capital of more than 66%. An economist from Carnegie Mellon found that teams with at least one woman on them had a collectively higher IQ than teams of all men. Organizations with women in leadership positions regularly enjoy lower turnover rates. 

We have all read statistics like these, but we don’t need any more statistics — we need prioritized action and empathic leadership. And, we need to understand that gender diversity is an asset to a company’s culture, its business outcomes and ultimately, the world at large. 

As Enenstein puts it, “Having more women in my company has enriched the way I run my business. We’ve been honored to hire women CEOs, put many in the C-suite and other leadership roles and I’m exceptionally proud. But you can never rest on your laurels, so we will continue to innovate. And because of that, we’ll continue to grow.”