What Happens When Startup Founders Connect at Scale

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To realize any major goal, two heads – or three, or four, or eight to ten, connecting authentically in a circle – are better than one. Steven Krein, CEO & Co-founder of StartUp Health, knows this from personal experience. As he and his partner Unity Stoakes built a company to invest in “Health Moonshots” that strive to improve the health and wellbeing of everyone in the world, he has tried to bring this kind of deep, intentional community support to his portfolio of 350 investments in 26 different countries. 

When first designing a peer network for StartUp Health, Krein drew upon his personal experience as a young entrepreneur in the Young Presidents Organization (YPO). There, through monthly meetings with fellow entrepreneurs, he learned that even though everyone has their own exciting projects, they don’t have to navigate challenges alone. “The trust and peer support,” Krein says, “and knowing that I’m going to have dedicated hours every month to do that, has been invaluable to me as an entrepreneur.”

So, when StartUp Health started out almost ten years ago, Krein arranged his founders in groups, based on the YPO model, and brought them together to gather face-to-face. But, as their portfolio grew from local to global companies it was no longer feasible to gather entrepreneurs in a physical space.  In shifting to a virtual format, Krein tried using “Zoom, and all of its predecessors” hoping to still parallel the YPO magic the community brought to his career. In short, it just wasn’t the same. “We had been connecting eight to ten entrepreneurs at a time,” Krein says, “but we didn’t have a reliable, dependable, intimate way of doing it that really created the trust and consistency that I thought was needed from what I experienced in YPO.”

startup health circle

Then came 2019: A fellow YPO member asked Krein if he had seen Circl.es. “It was instantly the answer for what I was looking to bring to my community,” Krein says. “To be honest with you, I think it’s made all the difference over the past year for our portfolio. Circl.es gets you off Zoom and makes you feel more connected. There’s a warmth to being in Circl.es.”

“I think it’s made all the difference over the past year for our portfolio. Circl.es gets you off Zoom and makes you feel more connected. There’s a warmth to being in Circl.es.”

Besides recreating a feeling that mimics how individuals connect in a physical space – in circles as opposed to “rows of tiles” – Krein and StartUp Health’s entrepreneurs love Circl.es for its design with best practices on how humans best build relationships in mind. Instead of relying on a hierarchical structure for how sessions are typically hosted in traditional meetings or on webinars, everyone is in the circle and no one is the host; they are all equal, as in the simple yet universal symbol of the circle. 

“You can tell Dan [Hoffman, the creator of Circl.es,] is intimately focused on the details of a YPO-like experience,” Krein says, “It shows that it’s not just people working on a product – it’s a product that’s had a lot of thought gone into it.”

To make this warm, thoughtful experience possible, Circl.es collaborated closely with StartUp Health to design Health Transformer Circles and a program that tailored the software to their objectives. They worked together to create 14 circles, with an average attendance of 8-10 per circle, including co-moderators. In just four weeks, Circl.es launched the personalized program, laying the foundations for a culture of belonging and engagement with consistent norms and protocols. As a nod to his inspiration, Krein even integrated YPO members to serve as mentors within each circle giving his entrepreneurs an opportunity to collaborate with additional outside perspectives that also understand the power of surrounding a startup founder with the right network. 

“It’s an incredibly useful replication of what happens in person”

Krein especially appreciates a few key features. He says it’s helpful that the presenter goes to the middle of the circle with a timer in the upper-righthand corner to guide. He also loves the virtual representations of raising your hand, giving a thumbs up, or even having everybody’s circle crowd into the center for a virtual hug. Details like incorporating music and changing colors, too, provide a sense of progress and closure, while the agenda lets the group know when it’s falling behind. All of these aspects help recreate the closest version to an in-person meeting as possible, while reminding members that they’re in it together. “It’s an incredibly useful replication of what happens in person,” he says.

Of course, Krein couldn’t love Circl.es if his entrepreneurs and staff didn’t see the value. These entrepreneurs say that it offers a fresh and engaging approach to discussing business and personal issues, while helping them build the deep and value-aligned relationships they need in order to solve complex problems and make the world healthier. And for his staff, there’s been an opportunity to engage further with these entrepreneurs as well and become more embedded in their needs, strengthening the overall company focus and culture within the portfolio.

Now, already in year two of the program, Krein realizes that a hierarchical and cold video conferencing software could never work. In addition, when the pandemic hit, StartUp Health had already embraced a virtual format of their program which eliminated the need to pivot quickly to this approach. All he had to do was remember, from his YPO meetings, the essential role that a reliable, dependable and intimate circle of peers plays in innovation and connection. Krein says, “Circl.es is very much one of the monthly rhythms that all of the entrepreneurs get to participate in.” Now, when StartUp Health’s entrepreneurs feel disconnected or stuck, they look forward to their next session on Circl.es as a reminder of collaboration and inspiration. 

“Even though creating communities is hard, Circl.es makes it easier.”

Building the best peer network collaboration opportunities for entrepreneurs has been an ongoing quest at StartUp Health and Krein now rejoices in seeing the entrepreneurs in his portfolio connect, make strides towards their goals, and is reminded that even though creating communities is hard, Circl.es makes it easier.

To hear more from Steven Krein about working with Circl.es to create Health Transformer Circles watch his interview with Logan Plaster, Editor, StartUp Health Magazine here.

In a world of physical distance, circles facilitate authentic human connection.

In a circle, 3-12 participants contribute equally, share openly, and push each other to act.

We spent years with academics and practitioners, honing best practices and building a technology platform. Our circles have helped scale peer learning, sustain manager and leadership development, move live training online, onboard new employees, support career development, teach collaboration, and build community.

We’ve been grateful for the support and the referrals from our large corporate partners, schools, and communities who have been hiring us to help design, facilitate and manage Circles programs.

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