USV & Circl.es – Unlocking Social Learning in a Portfolio Community

Union Square Ventures is a New York based venture capital firm that believes the best way to support their portfolio is by helping them learn and connect with each other. In addition to broadening access to content and community, their team has focused on building strong, trusted leadership networks across their portfolio of 115 active companies around the world. Their Network Lead, Lauren Young noted: “our team’s primary focus is to help our companies build better businesses. One way we do this is by increasing the speed of knowledge shared across the network.

“USV as a firm believes that we are not the experts in the room; rather, leveraging and building upon network effects can be one of the most impactful ways to build successful companies.”

USV as a firm believes that we are not the experts in the room; rather, leveraging and building upon the collective knowledge within our ecosystem can be one of the most impactful ways to help our companies build successful businesses.” Because of Lauren and her team’s proximity to the intense realities facing leaders of growing companies, they continually see the need to keep company leaders connected. “Building a company can be very hard, and today, the pace and intensity of growth and problem solving is never-ending. That’s why we seek out new ways to provide a trusted environment for senior leaders, executives, and founders in our portfolio to connect with industry peers.”

In the fall of 2021, as part of their ongoing efforts to connect leaders across companies, USV in partnership with Circl.es customized a version of Circl.es Foundations; a six -session journey of 90-minute sessions facilitated in curated small groups. Lauren explains how it fits a specific need in their broader learning and development curriculum: “Partnering with Circl.es has enabled us to provide a new layer of support: small group peer connectivity. Over the years, we’ve been asked by countless portfolio leaders for access to a space where they can ask questions and connect with others who are facing similar challenges. The foundation of this program was built from their feedback.”

“Partnering with Circl.es has enabled us to provide the exact layer of support we wanted– which was small group peer connectivity.”

Based on participant feedback, they have focused on two sorting criteria: department and seniority level. “Enabling participants to meet leaders who not only have the same functional expertise, but who are also facing similar leadership opportunities, increases the chances for them to develop stronger, more fruitful relationships.”  Lauren shared that one of the reasons they’ve partnered with Circles is to enable the executives in their network to really build a personal advisory board that they can turn to when they’re facing a challenge. Participants validated the importance of the peer element, with quotes like “I’m able to get perspectives on real time issues from peers” and “it’s great to have a place where I can be vulnerable with peers.”

Across the board, Circl.es Foundations yielded a fantastic response from USV participants: 100% of respondents would recommend the experience to a colleague. Overall, the feedback overwhelmingly validated the need for peer small groups in order to lead in the current climate. As one participant shared: “Being able to have a deep-dive session on problem-solving, and having it facilitated through a discussion broken up by certain themes, was very useful.” Participant Emily Bunin–Senior Controller at Kickstarter–shared that “transitioning into leadership as a professional can be challenging, and lonely at times. My USV circle provides a safe and supportive environment for me to face my fears, practice vulnerability, and remember that I’m not alone.” At Dwolla, Director of Finance Alicia Eichmeier mentioned that “it’s great to have a place where I can be vulnerable with peers” and Operations VP Jackie Ward said “it pushes me outside my comfort zone.”

“Transitioning into leadership as a professional can be challenging, and lonely at times. My USV circle provides a safe and supportive environment for me to face my fears, practice vulnerability, and remember that I’m not alone.”

Looking ahead, Lauren plans to continue to integrate participant feedback as well as the overall needs of the portfolio into this program. “Understanding our portfolio’s needs is critical to understanding where we, as a firm, can provide the strongest value proposition for them.” She appreciated the emphasis on strong facilitation, leadership-specific content and peer-led development that Circl.es has prioritized in their product and platform. Together, USV and the Circl.es team will add a layer of social learning into the fabric of the USV Network in 2022, forming new Leadership Squads each quarter, and providing peer learning & growth in a scalable format that reaches leaders one circle at a time.

Is Your New Year Powered by a Learning Community?

Every January, humans make (and sometimes break) New Year’s resolutions. Much has been written on how to master the process, everything from discerning and focusing on your why, to turning when into actionable calendar items. Results vary as we engage the hard work of change in our personal and professional lives. At Circl.es, our work focuses on an overlooked but powerful dimension of change, one that might not emerge as readily when making resolutions: the who. How does one’s community augment not only personal growth á la annual resolutions, but also noticeable change in the workplace?

Our clients have experienced the transformation that happens when employees connect and grow together in small groups. Head of Platform at Union Square Ventures, Lauren Young, knows there’s no curriculum robust enough to keep up with the challenges facing executives in USV’s fast-growing portfolio: it’s not necessarily what those leaders need, but who–they need community with each other. As she puts it, “Leaders working at rapidly growing companies are constantly facing challenges that require a quick decision or response. One way we try to support leaders within our portfolio is by connecting them with peers who either have gone through that experience, or can provide a safe space to discuss and brainstorm ways to approach it.”

“Great leaders don’t move people around a board like pawns;
they cultivate conditions for growth”

Lauren practices what General Stan McChrystal refers to as the difference between  “gardening” and “playing chess.” Great leaders don’t move people around a board like pawns; they cultivate conditions for growth. In his video The Leader as Gardener, McChrystal expands the metaphor: “A gardener grows nothing, plants do that–that’s what plants are designed to do, and they’re really good at it. But the gardener’s role is not unimportant…all the things the gardener does to create an environment and ecosystem allows the plants to do what they do, and do it very, very well.” Like plants, humans naturally circle and grow together, provided leaders present the right conditions.

When the pandemic deprived leaders of offices, campuses, and hotel event spaces, it forced intentionality and creativity as they grappled with how to create garden-like spaces where employees can gather and flourish. Priya Parker, in her book The Art of Gathering, discusses the sin of being a “chill” host at a party, “Chill is a miserable attitude when it comes to hosting gatherings … I want to convince you to assume your proper powers as a host.” Thoughtful hosts decide who needs to connect with whom, and with a little forethought, what topics they should discuss. Like a good party host, organizational leaders can use small groups to set the stage for deep connection. Fortuitously, this combats pandemic realities like disconnection, disengagement and loneliness.

“Like a good party host, organizational leaders can use small groups to set the stage for deep connection.”

Leaders increasingly look for learning groups for themselves, many joining professional cross-company learning communities that connect them with others working on similar projects. Despite limited ability to gather in-person, our clients like YPO and Executive Networks reported record growth and renewals this year. New communities like Atlas One for sales professionals and Round for technology leaders emerged. Ryan Fuller, CEO of Round, says that “A vetted community rich with perspective and grounded in shared values provides unparalleled access to knowledge and opportunities from fellow members dedicated to helping each other.”  Degreed upskilling platform has documented this shift from internal connection to connecting professionally between organizations–their data revealed that 62% of executives sought to learn from professional networks in 2019, and we believe the pandemic has accelerated this trend.

This movement is consistent with an approach known as communities of practice, a term Ettiene Wenger-Traynor coined while studying the ancient system of apprenticeship. His studies informed him that many have long misunderstood the role of an apprentice’s master: traditionally, apprentices actually spent very little one-on-one time with masters–like the plants in McChrystal’s garden, apprentices mostly learned from each other. As we heard him say in a recent workshop: “finding the knowledge we need to solve today’s problems starts with coming together in uncertainty and figuring it out. We even saw university presidents form peer groups to figure out Covid.” 

Those of us who have taken a class from an expert or read a book alone have experienced the absence of such a community; we emerge swamped with expertise, yet starved for the practice and peer support that produces true change. Many leaders we work with also describe falling into another trap: while they may successfully group employees or community members together through directories, social media groups, and email newsletters, the results have been lackluster. As pointed out by Gina Bianchini–founder of the community management platform Mighty Networks–these large, flat groups are truly social media–that is, one-way communication that most of us passively consume, making it the junk food of human connection. Actual conversation and connection are vital to transformational small group communities.

“Actual conversation and connection are vital to transformational small group communities.”

In contrast, our partners are proving that small groups, like circles, elevate a community into a learning community, facilitating authentic connections and enabling social learning. The recipe is clear: gather a diverse cross-section of people with a common purpose.  Foster a safe place. Watch as the power of peer connection pressures action, and taps into another great need–the desire to serve something beyond themselves. At this point, the community benefits just as much as the individual, as shared trust and vision compels greater job longevity and performance.  

As February nears and we distill our lists of resolutions–some fade, and the right ones will inevitably rise to the top and stick–consider adding to your list of resolutions something that focuses not on why or how, but on who. Will we actively host our parties, tending the gardens of our companies and communities? We can not only improve the chances of seeing our own resolutions through; we can help create spaces and learning communities where others can thrive and become their fullest selves. 

We’re here to connect with you.

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Virtual hugs,
Dan
CEO, Circl.es

Interested in becoming a part of the Circl.es team? Check out our open roles.

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.