What Happens When Startup Founders Connect at Scale

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.

This Is How We Can Shape A Better Virtual World

I have worked as an entrepreneur for the past 20 years, doing my part to build out the Internet. During that time, I’ve been comforted by the idea that helping humans connect is good for the planet.

But mass interconnection has drawbacks. Communication bubbles deepen tribal divisions. Mega-companies, like Amazon, are wiping out local brick-and-mortar shops. Misinformation abounds and we’re increasingly aware of our lack of privacy on the Internet. And, ironically, many of us feel more isolated than ever before.

Thanks to the pandemic, the world of virtual communication has seen a building boom. Clubhouse, an app that lets people gather in audio chat rooms, is one of the newest structures on the market; announcements of its arrival exploded onto front pages and Clubhouse received a $1 billion valuation after just a few months of live service. 

Companies like Clubhouse show that virtually, we can build big audiences and communities, and even companies, quickly. But are we architecting thoughtfully? As Winston Churchill said in 1943, “We shape our buildings; thereafter they shape us.” Can we imagine a new way to design these virtual spaces so they reinforce the best of our humanity?

Here’s a small example. Jodie McLean, CEO of EDENS, a real estate owner, operator, and developer, was, like so many other CEOs in 2020, grappling with how to help her newly remote workforce avoid the risk of being divided by this isolation. McLean was also aware that this physical isolation was occurring at the same time that the company needed to come together for conversations about systemic racism perhaps more than ever before. The first thing she tried was a large-format webinar for her 200-person staff. But it didn’t generate real conversation or connection.

The next time, she tried a different virtual structure. Staff were placed in small rooms of ten, faces arranged in a circle. They met for two 90-minute sessions. They had some quiet time to reflect, and then timers and an agenda guided their conversation. They talked about their identities at work and how the issues roiling our country show up in the physical communities EDENS constructs for customers. Staff were apprehensive at first, used to sitting back with cameras off. But after the sessions 95% of the staff raved about their experiences, noting that their conversations were authentic. No professionals facilitated the sessions. At the end of the day, McLean observed, “We’ve never felt more grateful for each other.” 

Sitting in circles is a very old idea. When people are in a small group, all facing each other, they feel included. They engage. They offer ideas and share their challenges. Over time, people connect and begin to help each other. Many of our physical spaces are not set up for people to be in circles. Think classrooms, or trading floors, or churches, or auditoriums. These spaces deeply embed ideas of hierarchy and assembly lines and teacher-as-expert. Our move to virtual spaces is a chance to question this. 

Double-click on the example of corporate learning and development. From 2000-2012, my previous startup had to grow fast to keep up with an exploding market. We couldn’t hire for new skills fast enough. We needed our people to grow, so our company could grow. I began to focus on what it would take to build a learning culture at work. Unfortunately, the learning tools we had fell short: a corporate “university” filled with out-of-date slide decks, skills training videos, managers coaching subordinates 1:1, a performance management system no one kept up to date, and the occasional one-off workshop. They failed to engage all but a few very self-directed learners. 

One thing we tried, though, worked: a “Battle of the Bands,” where about a third of the company took up bass, drums, guitar, keyboards, or singing. Music teachers helped remind people how to learn, how to listen to each other, how to practice. It was an exercise in how important it is to create an engaging experience where learning in teams can push individuals to be their best selves. 

Our common corporate learning structures were built for old circumstances. We no longer have to mass-produce workers for assembly-line jobs. Information is no longer scarce, requiring people to gather around an expert. We have the opposite problem: there’s a tsunami of information every day. Our workforce needs highly diverse and flexible creatives that can work together.

Corporate learning and development echoes the education system overall, which is also made of traditional structures and has a similar disengagement problem. While 63% % of kids are served by the four-year college system in the US, 40% of those students do not complete their degree within six years. It makes me think, if more of those students are fully engaged during college would graduation rates increase?

There’s evidence that study groups improve matriculation rates and success, and small groups or “team-based” learning improves the satisfaction of both student and teacher over lectures. The Harkness method, pioneered by Philips Exeter Academy in 1930, in which all classes are conversational and conducted at an oval table, is gaining popularity. Many states now have mandates to use restorative practices, a circles-based approach to community building and repairing at schools, which is proven much more effective than the traditional ways of organizing schools.

In fact, it turns out that many educational approaches draw on the power of circles. They have different names: forum, which is used by organizations such as YPO;  communities of practice, which are used across businesses, schools, and in government;  text-based dialogue, which is used by the Aspen Institute; and the list goes on. They all have common practices. Harvard Business School programs house their attendees in a living group of eight single rooms around a kitchen, and a coach helps each “living group” jell into a circle that works together on cases and projects. 

I’ve personally had some learning experiences in circles that helped me, taught me, and pushed me more than any class or coach or even consultant had done before. In my 30s, I was a first-time leader of a scaling company and my EO and YPO forums, each with 7-8 other CEOs meeting every month, were how I really learned to do that job. When do I reduce staff or leases when the economy was giving out? How do I show up at the office when my dad is slowly passing from ALS at home? How do you negotiate partner differences, is PR worth it, is my public speaking good enough? After exit, I was lucky enough to be picked for the Henry Crown Fellowship, a circle of leaders at similar transition points. In this Fellowship, The Aspen Institute gave me the space to explore values, what I thought was good for society, and next steps. These circles were transformational.

The learning field is bubbling with new ideas, technology, neuroscience, and data science. But quietly one of the oldest ideas is gaining traction with both approaches to learning and how best to work: sitting in a circle.

Almost everything we do at work is performed in a team. Team structure methodologies like Agile (cross-functional teams working sequentially in a structured manner), Scaling up (daily huddles to improve communication), EOS/Traction (working quarterly towards a set of company goals) and Holocracy (employee flexibility to take on tasks in a flat corporate structure) emphasize the importance and power of small teams learning together, quickly. They each have a small-group structured meeting at their heart. 

The success of these small group structures relies on teams to collaborate openly. Google’s Aristotle project found that psychological safety –  the belief that one will not be punished or humiliated for speaking up with ideas, questions or concerns  –  was the clearest success factor across hundreds of teams they studied. Circles practices foster this kind of safety, through group conversations where no one dominates the conversation, everyone is made comfortable speaking and feels heard. They help the boss sit alongside you on the team modeling vulnerability, instead of issuing updates and orders from the front of the room.

I spent a lot of energy as CEO trying to produce a consistent corporate culture and alignment throughout the company.  But the actual culture that an individual experiences day-to-day has everything to do with their immediate team. We need to learn to lead “teams of teams.” This will help with the ridiculously low level of employee engagement that Gallup reports across our companies year after year. As my Aspen Fellow, now Heineken’s CEO, Dolf van den Brink said to me, “We’ve done a good job of building structure across the global org chart, but not where it matters most: inside teams.”

The idea that led me to found Circles Learning Labs, Inc. (Circl.es) was to help make it easy for people to learn and work in circles. I wondered why everyone in the world doesn’t have a Forum, like I did when I was a new CEO? Or a Fellowship to help them figure out their next career move? I asked myself if I could help solve problems for all the restorative practice leaders or the Holocracy crowd who were increasingly working on this? 

When I started experimenting in 2016 I thought that we’d be building a matchmaking service: use LinkedIn to find, for example, eight new marketing leaders at small companies. But it turned out that this part was relatively easy: communities and companies had already collected like-minded peers. We didn’t think we’d have to build a video space at all, but when we experimented with a new interface where people were in a circle instead of a grid, we got incredible reactions. It turned out that all these different kinds of circles have very similar best practices, making it a good candidate for software. It was hard and expensive for companies and communities to set up and run lots of circles – another problem that lent itself to a software solution. 

So we’ve set out to build a virtual space where every feature we add or take away fosters authentic human connection and makes it easier to run and scale lots of circles. The outcomes so far leveraging Circl.es with organizations like EDENS, are encouraging:

  • Harvard Business School struggled for years to find the right way to support executive education students to practice and apply learned skills after leaving campus. Their “Virtual Living Group” program keeps busy CEOs meeting monthly in circles. When Covid hit, we added Circl.es to their virtual campus, reducing truancy in virtual programs to almost zero and “significantly deepening the in-classroom conversation.”
  • Millennium Schools ran circles of teachers and 89% said it improved their ability to support students, 90% said it boosted their wellness, and 92% said it reduced their sense of isolation.
  • Ken Blanchard companies found that breakout circles improve workshop outcomes and lead to successful follow-up. “There’s two things that lead to successful learning sustainment – accountability and relationships,” noted Diana Urbina, Head of Coaching Services. 
  • Chris Anderson, TED’s founder, started TED circles to help move his community from inspiration to action. The program has exploded to thousands of circles globally in under a year and is quickly becoming a core part of the TED community.
  • Jumpcrew, an outsourced revenue company in Nashville, TN, began its Circl.es program before the pandemic. It has continued to grow quickly in a remote working environment as they’ve found that building “circles for our upcoming leaders has reduced employee churn and improved our culture.”

Even more encouraging than the program outcomes are the participant testimonials we receive after a session on Circl.es.

“I love the discussion in each session and navigating real, deep life situations together.”

“Circl.es makes space for a high level of open honest communication.”

“So good to hear from others – so many common threads of struggle and celebration which is incredibly encouraging!

“Continuing as a tight-knit group to grow, evolve, learn and gain insight from one another.”

Circles are humanizing. Research suggests that when we feel we can show up more authentically, we are more open to new ideas and feel a greater sense of well-being. It has never been technically easier to form small circles of people from all over the world and run a circle well. Anyone can use Circl.es’ best practices to facilitate the energy, timing, and flow that makes time together in a circle feel packed. The output from a well-run circle in a virtual setting can expose us to true diversity and change the way we think.

Maybe the future of learning and work is a return to the past. Fewer presentations, more conversations. Space and time for small groups to connect, without the torrent of thousands of voices reaching you through your screens. Space to reflect and process, instead of taking in more information second-by-second.

Over the years, we’ve built big, hierarchical structures; now leaders can focus on what happens at the edge, fostering more intimate connections where people can bring their authentic, full selves to conversations and connect as humans. And with a little help from the pandemic, we can take advantage of the fact that many employees aren’t returning to their rows of desks, and change the shape of our reality.

Dan Hoffman is CEO & Founder of Circl.es. To hear more from Dan, connect with him on LinkedIn here or continue to follow our blog.