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Unlocking Founder Potential in a Rapidly Changing World: Introducing the Real Fellowship

The speed and unpredictability at which the world is shifting, especially the world of technology and venture, requires founders to have a more adaptable and robust way of making sense of this ever-increasing complexity. We have come to see that the lack of a fit-for-purpose navigation and decision-making framework for founders is the underlying cause of co-founder conflict, founder burnout, depression, conflict at home, and in many cases the real reason for business failure.

It is our belief that the rapid speed at which the world is evolving has created an environment where the current systems of thinking and operating within the startup ecosystem are no longer serving entrepreneurs. In fact, we think these outdated systems are actively limiting their potential to build and scale massively impactful companies. They are limiting entrepreneurs’ leadership capacity. For more founders to be successful in their entrepreneurial pursuits, a mindset shift better adapted to the challenges of today is needed.

The structure of a program to facilitate this shift had been percolating in our minds for some time, but we realized that with a portfolio of over 70 companies, we would need a much larger team to deliver the type of impact required to catalyze this shift at scale.

And so six weeks ago we launched a first-of-its-kind new program designed to attract, develop and support a dozen new allies in service to supporting Real Ventures portfolio founders as they develop and test out these new navigation and decision-making frameworks. These allies are the Real Fellows and the program itself is called the Real Fellowship.

What is the Real Fellowship?

The Real Fellowship is a select group of diverse and accomplished entrepreneurial leaders who intimately understand the operational, mental, and emotional challenges inherent in the founder journey. Fellows share a desire to give back to the startup ecosystem by supporting other founders in their entrepreneurial pursuits. Just as importantly though, they, like the founders they are supporting, understand the importance of expanding their own leadership capacity through a commitment to personal development.

Our objectives for the program are twofold;

  • To provide our portfolio founders with monthly support from human-focused entrepreneurial leaders (fellows) with whom they can develop a deep and trusting relationship where they feel heard, healthily challenged, and supported;
  • To cultivate a community of leaders committed to developing their own leadership capacity in service of their organizations, missions, and the evolving needs of society and the planet in an era defined by evergrowing rapid and complex changes.

Fellows are matched with 1-2 founders from the Real Ventures portfolio for monthly calls aimed at growing their organizations based on a process that prioritizes the nurturing of deep and authentic relationships. These interactions serve as a crucible for fostering trust and vulnerability, where both fellows and founders can freely express themselves and navigate the complexities of entrepreneurship together. When pitching the Fellowship program to both fellows and participating founders, we emphasized that Fellows were not meant to be mentors or advisors for businesses but peers and collaborators for founders. So many of the exchanges CEOs engage in are transactional by nature, often leaving them feeling used and alone. When engaging with a fellow, the relationship is rooted in humanity and empathy from day one.

Leadership Retreats Designed to Generate Human Connections over Transactional Exchanges

In exchange for their support, Real Ventures provides each fellow with a series of all-expense-paid leadership development retreats led by world-class facilitators, meticulously crafted to deepen their self-awareness and catalyze their leadership capacity.
The first of these retreats took place in Montreal this February. Unlike most professional events, we didn’t start by asking fellows to introduce themselves by sharing their names and listing their professional accomplishments. Instead, everyone introduced themselves by sharing who their favourite superhero is and why. For a group of individuals who are used to being judged by their professional accomplishments in most of their interactions, this approach to meeting and connecting with peers was uncommon but met with enthusiasm and appreciation.

In fact, throughout the entire 3-day retreat, we didn’t discuss missions and visions, strategic planning, change management, team building, and other more common themes explored in traditional leadership development retreats. All activities and workshops were centred on three main themes:

  • Creating a cohesive and connective experience for fellows to bond with one another;
  • Enabling fellows to experience meaningful and authentic connections and;
  • Empowering fellows to deepen their personal developmental journey.

We wanted to create a safe environment where fellows felt they could show up as their authentic selves with a group of peers and feel heard, accepted, and empowered through a shared purpose.

At the beginning of the retreat, each participant agreed to the following:

  • Be for each other
  • Listen deeply
  • Speak real and keep commitments
  • Balance support and challenge
  • Praise generously

These simple yet powerful agreements set the stage for an experience unlike any other in the venture startup community.

Real Fellowship fellows and members of the Real Ventures team engaged in a personal development exercise led by facilitators Pete Strom and Aithan Shapira from Made to Tilt during the first fellows retreat on February 16th, 2024.

Fostering Meaningful Peer Relationships Between Entrepreneurs

Exceptionally during this first retreat, we also invited Real Ventures portfolio founders to attend a portion of the event. Because a shared purpose or experience is so important when forging new relationships, we wanted founders and fellows to have the opportunity to interact in an open and playful environment before proposing official pairings. This also afforded founders the opportunity to engage in self-exploratory activities and exposed them to some of the development frameworks shared with the fellows.

One particularly well-received activity was the “higher self” exercise. In this exercise, participants formed small groups of five, arranged in a circle, and engaged in a series of open-ended questions directed at one group member at a time. However, there was a unique twist—the individual responding to the questions was instructed to stand behind their chair and offer insights from their “inner consciousness” or “higher self,” necessitating responses in the third person. This approach encouraged participants to adopt a reflective stance and provided an opportunity for self-reflection and introspection.

For instance, a group member might pose the question, “What does Isabelle enjoy doing in her free time?” The respondent, speaking as Isabelle’s “higher self”, could reply, “Isabelle loves to play basketball. She played during college and it is one of her favorite pastimes. She feels she hasn’t made enough time lately to play and I think she would like to change that. I think it would help improve her overall well-being and give her renewed energy and creativity in other spheres of her life.” By articulating personal insights in the third person, many participants found themselves uncovering truths about themselves they hadn’t previously recognized. This unique approach fostered a sense of safety within the group, encouraging individuals to share candidly about themselves. As a result, the group quickly cultivated a profound level of trust and camaraderie, given the deeply personal nature of the discussions.

The results speak volumes. Following the first retreat, participating Fellows reported an average satisfaction rate of 4.7/5. In terms of feedback, participants shared that they learned more about themselves, discovered new tools for personal and team development, and developed deep connections with other Fellows. Similarly, founders who were able to join us also reported an average satisfaction rate of 4.6/5. Many appreciated the refreshing focus on their humanity and valued the opportunity for self-reflection, energizing them to bring renewed vigour to their businesses.

The outstanding feedback, coupled with the enthusiasm from all parties to begin their monthly calls underscores the significance of this novel approach to founder support and development. It reinforces the notion that such initiatives are not only appreciated but vital in cultivating a startup ecosystem where founders feel a profound sense of belonging, are empowered to embrace their authentic selves, and are better equipped to navigate their businesses through the trials of a rapidly changing world.

Laying the Groundwork for Regenerative Entrepreneurship

We believe increasing leadership capacity starts with the development of a deeper sense of self-awareness and system-awareness. By cultivating an intentional practice of inner reflection, in which founders are focused on better understanding their relationship with themselves and how they relate to other individuals, their teams, and their environments, they are more likely to develop the resilience and the mental fortitude needed to navigate rapidly evolving environments.

Real Ventures’ desire is to create deliberately developmental environments in which founders can continuously grow themselves so they are better equipped to build successful businesses in service of people and the planet. Given the persistence of external pressures shaping the market, it stands reasonable to think that founders open to changing the way they think about business-building will also need the support of a robust network of experienced and dedicated peers and mentors who share this same mindset shift. This is where the Real Ventures Fellowship comes into play.

The Real Fellowship is part of an increasingly expanding founder education and development approach built around the twin pillars of self-awareness and system-awareness. This type of development is sometimes referenced as “inner development” or “conscious leadership”, but another term we have come to appreciate is “regenerative entrepreneurship”. Regenerative speaks to the capacity to understand and act in ways that prioritize the health, well-being, and prosperity of any system, including that of the individual, the team, the company, stakeholders and the natural world.

Our ambition is to continue to build from the learnings acquired through the Real Fellowship (and other programs we’ve led, such as those offered during the last three cohorts of our accelerator program FounderFuel) and share our insights so that they may serve as a catalyst for systemic change with the power to shift the mindset and approach for the whole of the startup ecosystem, and perhaps even beyond, from a purely profits driven system to a regenerative system that generates profitable outcomes across all spheres of human and planetary activities.


For more on our thoughts on helping founders become wiser, faster, so they can build sustainable companies with global impact, sign up for our newsletter and follow us on TwitterLinkedIn, and Facebook

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