Five powerful pieces of advice for founders (from founders who’ve made it)

Building a company is one thing. Building a company while taking care of your well-being is another. At WeWork’s first-ever Leaders’ Wellness Summit, two successful founders — Janine Yancey and Doug Lessing — opened up about their founder journeys and how wellness played an essential part.

Five powerful pieces of advice for founders (from founders who’ve made it)

1. Be kind to yourself.

Moving on from his first company after three decades was a huge transition for Lessing. His coach advised him to be kind to himself, leading Lessing to, of all places, a float tank. Though he’d never been, he went 100+ times while exiting one company to build another. “There you are, lying in the dark, in six inches of water,” he recalls, “and it was one of those things that allowed me to be kind to myself, to absorb all the shocks to the system coming from the uncertainty and transition to a new company.” It stuck to him. When an audience member asked what his first action would be if he had a vision for something new, Lessing answered, “I’d go into the float tank.”

2. Know it pays to be intentional

Yancey used to not think twice about reaching out to team members on weekends or early mornings. In her mind, she just wanted to get the message off her doorstep and onto theirs. Observing how expectations around employee experience had changed recently (and having a teammate admit the last thing they wanted on the weekend was a paragraph on Slack from the founder), Yancey challenged herself to become more intentional about how she communicates. She noticed the payoff nearly immediately and now does the same with her self-care strategy, intentionally scheduling an hour for herself on her calendar.

3. Play the long game with patience

“The biggest risk to startups is not funding, not the idea, not product market fit, it’s the founders giving up,” says Lessing, who notes that practicing patience can help keep founders from quitting. “Building a company is very, very hard, and it’s going to take time,” Lessing states. He likened it to triathlons, explaining how, in a race, it pays off not to be the fastest swimmer, so you have the legs for the bike and then the run. “You have to take the long view, get rid of the transactional mindset, and be patient because it’s an endurance game.”

4. Making caring your superpower.

“When I look back over the 30 years in my last business and building this company, I realize my strength is that I care,” notes Lessing. “I care about people, about relationships, about details, and about being authentic.” His experience has shown that things like safety and well-being come naturally in a place where people care (especially leadership). Caring also empowers top talent. Lessing points to the triangle of trust and how empathy (making sure people feel you care about them) is a core piece to the triangle and, coincidentally, a core attribute of Lessing’s high performers.  

5. Let go so you can grow.

Yancey is a CEO most comfortable in the trenches…but she also knows the most successful CEOs can see what must be done from 30,000 feet. To get her there, one of her mentors, a 4x founder, explained, “You will never have someone on your team that’s going to do the job as well as you because they don’t have the same level of investment or skin in the game — and that’s okay.” He explained how part of her job was to get comfortable delegating, even if it was to someone who was a little less skilled or would put a little less time into it. They’d still get the job done. She’s leaned into this advice while growing her team — knowing it’s what’s best for her and the business.

Turning advice into action

From exercising kindness to being more intentional, these pieces of guidance have helped both founders succeed — and even move on from success — while honoring their well-being. As you try this advice to see what works for you, know that change doesn’t need to happen overnight. “Don’t rush off in all these different directions,” says Lessing, “study yourself.” And know, too, that wellness is what can make all the difference in your business. 

Practicing wellness with WeWork

This advice stemmed from WeWork’s 2024 Leaders’ Wellness Summit, a half-day, bi-coastal event focused on bringing well-being to work. Whether they joined from New York or San Francisco, wellness was on the agenda. Beyond the fireside chats, attendees learned how to build a culture of well-being thanks to a panel of experts from the Founders Network. Guests had a chance to practice yoga and meditate with a session led by CorePower Yoga. And meaningful networking opportunities were paired with snacks and sips from Boisson and Athletic Brewing

About the speakers 

Janine Yancey

Janine Yancey is an expert in the future of work. A lawyer and HR leader, Janine founded Emtrain to provide an online learning solution to develop and measure employees’ skills in ethics, respect and inclusion, and give employers a scalable tool to proactively manage employee behaviors. Janine’s vision of a skills-based, data-driven talent approach on culture topics has put her at the forefront of thought leadership on sexual harassment, bias, diversity and ethics issues. Janine is a sought-after speaker and has been published and interviewed in the mainstream media including Washington Post, USA Today, ABC, MSN, CNET, Bloomberg Business, Tech Crunch, and Startup Grind.

Doug Lessing

Founder of Phin, advocate for companies doing good and becoming stronger while doing so.

Doug Lessing, as a speaker and longtime partner of multiple tech companies over the past 30 years, has made it his life’s work to evangelize the importance of using business as force for good in a fractured world. As the Founder of his latest venture, Phin, a philanthropic tech platform and certified BCorp, he is an advocate for companies being great by doing good. Phin models the BCorp ethos of using business as a force for good while helping companies build great teams and company culture by incorporating positive values and social good into their daily actions. Doug is featured on Worth Magazine’s Worthy 100 Entrepreneurs. He currently serves as an advisor to several founders and is on the leadership team of Founders Network, a group of 700 tech founders from around the world. Doug was born and raised along the Great South Bay of Long Island, NY and now resides in Blue Point, known for its oysters and beer. Married to his wife Grace, with 3 Gen-Z daughters, Alexie, Jillian and Lindsay, Doug has been surrounded, outnumbered and influenced by strong women. This positive influence has encouraged him on his quest to be an exponential force for good and compassion, creating a more equitable, healthy and peaceful world for future generations.

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Management and Leadership