In this essay, we explore the formative experiences of the founders in the Redbud VC portfolio and why we believe these moments, often found at the intersection of circumstances and opportunities, are critical in a founder’s journey to success and key factors in forming an outlier.
In 2014, Marc Andreessen sat down at Stanford University to candidly share what his firm looks for in founders, “The venture capital business is a 100% game of outliers- it’s an extreme exception.” Simple as that: great founders are outliers. Chasing these outliers has since become a common trend in Venture Capital as firms boast and argue what makes them the best at choosing who has these “extreme exceptions.” The irony is that no one truly knows, but as VCs, we do our best to build reliable frameworks around who to choose, and we wait, on average, 7–10 years to see if our assumptions are validated and if we successfully chose the outlier.
Emerging frameworks designed to capture outliers fall into a few categories: education, geographic area, professional experience, motivational factors, personality traits, network, and challenges. Many VCs rely on “pattern recognition” in those areas, i.e., checking boxes on key points such as prestige or pedigree. The dependence on attempting to replicate previous formulas for success has arguably led many VCs to invest only in certain areas or within specific groups, e.g., Ivy League alumni or ex-FAANG. VCs tend to place bets where opportunity and privilege are plentiful; often, a belief exists that entrepreneurial success is directly correlated. In other words, although VCs are driven to search for outliers, they end up falling into the trap of pattern matching to the median. At Redbud VC, we are betting that entrepreneurial talent is evenly distributed even though opportunity is not, an idea that is not original in thought but is in practice.
Education and Pedigree
Education is the easiest box to check for VCs, as there is clear data on how founders from top-tier universities have the resources and networks that are robust enough to support them as opportunity comes. Recent PitchBook data showcases that the vast majority of VCs prioritize founder and executive team pedigree first when evaluating an investment opportunity. In 2022, McKinsey conducted a study on commonalities between the founders of Unicorn companies, finding that 95% of unicorn founders completed an academic degree and over 70% have an advanced degree such as a master’s, MBA, or PhD. Educational statistics have led VCs to deploy a third of their capital in their university alma mater when 40% of the VC industry is dominated by Harvard and Stanford alumni. Acceptance and completion of a higher educational program is a statically strong signal towards entrepreneurial success but is once again a pattern, not an outlier.
VCs tend to place bets where opportunity and privilege are plentiful; often, a belief exists that entrepreneurial success is directly correlated.
We asked the founders in our portfolio to share details about their educational background and significant experiences or learnings that happened throughout that time. One founder shared, “I was a terrible student in undergrad, especially the first 2 years. I had to take a lot of classes over and had to fill my final semester with over 30 credits of classes to boost my GPA. It taught me to manage my time and push myself to work harder than I had ever worked before.”
Another founder shared, “I worked as an auxiliary campus police officer while at [University]. One of my duties was to stand at an intersection for 8–10 hours directing traffic on home football game days. A lot of days it rained or snowed, and I’d just be out there completely soaked, freezing my ass off. I learned a lot about toughing out the unpleasant parts to get to the other side.”
A common thread across many responses in this category was remembering a specific experience that shaped the lens through which they approach being a founder rather than a person or connection. These small but defining moments early on have the biggest influence (or impact) on present-day principals.
The prevailing belief that prestigious universities serve as reliable predictors of entrepreneurial success is flawed. While a substantial number of founders emerge from institutions like Harvard and Stanford, this correlation does not guarantee outlier achievements. In fact, founders who studied or worked at the University of Cincinnati are 3.3x more likely to achieve unicorn status than other founders. Admission to elite universities is often influenced by socioeconomic privilege, family networks, academic coaching, and other factors unrelated to entrepreneurial talent. The bias toward graduates from prestigious colleges triggers an influx of capital into said founders, creating an inaccurate perception of reduced risk. In other words, as a founder, having the “right” educational institution associated with you can erroneously signal safety to investors, perpetuating this cycle of bias.
Professional Experience
Professional experience is another key determinant of securing VC funding and evaluating founder backgrounds. Founder pitch decks often flex points of operational, technical, or prestigious work experience and are quantified by products shipped, revenue increased, etc. It’s hard for investors to ignore startups founded by ex-Meta, Twitter, Uber, or any top tech company talent. A founder’s professional experience undoubtedly contributes to a founder’s credibility, yet is not always directly correlated to quality.
When speaking to our founders about key moments in their professional experiences that shaped them, many spoke about pivotal moments of opportunity: “I spent 15 years as a civil engineer, eventually getting to a position normally occupied by people with 15+ years of experience more than me. I was really lucky; the companies I worked at needed someone organized, and I could step up; otherwise, no one in their right mind would hand a multibillion project to a 30-year-old.” Challenging moments of opportunity are essential to developing empathy for a problem.
Another founder stated, “I was previously a Legal Officer at eBay, conducted due diligence at an angel investor group, analyzed the status of international contracts at the Court of Justice of the EU, worked at a community legal center, and have some law firm experience. My legal professional background absolutely equipped me to build the venture I founded, as it couldn’t exist without it.” Robust experiences with moments of opportunity often outweigh flashy company names or titles. At Redbud, we listen to these learnings and believe they can happen at any organization regardless of prestige.
Geographical Influence
Geographical influence is arguably the most explicit line drawn by investors — narratives about the coasts vs. Midwest and SF v.s. NY, etc., are a continuous topic of VC blog posts at all stages. It’s no secret that founders historically flourish in places like Silicon Valley, New York, Chicago, and other bustling urban hubs brimming with venture capital and abundant opportunity. A prime illustration of this phenomenon is when investors assess the “quality” of founders. Take, for instance, a founder hailing from the heart of San Francisco, a city synonymous with technological innovation. Investors instinctively place these founders higher on the scale of talented entrepreneurs. In stark contrast, investors may scrutinize a founder emerging from less tech-centric geography like Nebraska or Missouri and question, “What do they truly understand about being a startup founder?” Again, a seemingly inherent bias is in fact, the manifestation of pattern recognition rooted in geographical bias.
Living in a traditionally overlooked area can instill unique traits in founders that are cultivated through the experience of building a company where there are limited examples of past success. In contrast to coastal cities with plentiful examples, opportunities, and blueprints for success, small, less VC-populated areas have the potential to breed founders who are grittier and more resilient. As one founder in our portfolio put it, “I and others frequently felt like we were alone on a remote island fighting for basic things that coastal startups enjoyed in abundance.” Resilience can be a formidable asset in the entrepreneurial world. It encourages founders to be resourceful, adaptable and focused on problem-solving. Founders from such overlooked areas often have a deeper connection with their local communities as they have had to first look locally for support and resources. “I was born and raised in the midwest and believe, after living on both the West Coast and East Coasts, there is definitely an aspect of community, helping your neighbor, and holding honesty and transparency that is deeply embedded in my approach to life, business, and people.”
While building a company or hailing from an overlooked area can bring founders with strong traits and principles forward, the limits of said geography can restrict founders to operating within the confines of what they’ve seen. There often becomes a point where thinking outside of one’s community is discouraged, and founders retreat to the patterns of what has been locally “successful.” “[I’ve lived in] London/Ireland/Frankfurt/Lagos [and] living in multiple places made me realize how big the world is and how much opportunity there is however, there are (real but often over publicized) statistics surrounding my community who are always portrayed as ‘under’ served/estimated/funded so you’re mocked or actively discouraged for thinking big or outside the norm.” Founders often feel a tension between what they are striving to create and an existing mold of “success.”
We believe providing these moments of exposure to our founders is important as they often prove to be essential learnings that deeply influence future decision-making and the shaping of an outlier.
Exposure to top-tier ecosystems and thriving markets can push founders to think outside of the norm. Accessibility to examples of outlier founders can help others avoid mistakes, create relationships, and iterate alongside an individual who has done it before.
More than one founder in our portfolio wrote about the moments that pushed them to embrace their strengths while simultaneously thinking big: “I have always had big goals for myself, and I knew that I’d eventually build something big on the world stage. I grew up in an environment that encouraged ambition (albeit, traditional). Having access to a variety of TV channels (specifically, [shows in the] US like Disney Channel — I’m serious!) and the internet made me be more extroverted and think bigger than most of my peers.”
Exposure to diverse media, people, things, and places, no matter how big or small, is critical in a founder’s journey toward perspective. We believe providing these moments of exposure to our founders is important as they often prove to be essential learnings that deeply influence future decision-making and the shaping of an outlier. By recognizing how to nurture such experiences, Redbud is able to identify founders that would typically be overlooked if evaluated against an investor’s traditional framework for success.
Motivating Factors
The motivational factors that propel founders forward are the unseen catalysts of creating outliers and are unique to each founder. It’s difficult to dissect motivation and place it into distinctive categories. Unlike education with statistical ties to “founder success,” motivation cannot be statistically grouped, and therefore, it is difficult for investors to drive patterns and assumptions around it. When we spoke with our founders about what motivated them, some attributed defining moments in forming a “chip on their shoulder,” while some founders spoke of the circumstances that provided the privilege and opportunity for them to build a company.
As we dissect the formative experiences of our portfolio founders, it becomes apparent that motivations are not just personal narratives but powerful drivers influencing the trajectory of their entrepreneurial journeys. One founder shared: “Being immigrant founders, our success impacts our visa status, intensifying our drive to excel. My motivation is also deeply rooted in Chinese familial values and my academic achievements. However, another chip comes from my passion for architecture.” The intertwining of visa status, familial values, and a passion for architecture forms a unique blend of motivations that extends beyond the conventional markers of success. It’s the blend of diverse and very real motivational factors that are the tipping point in propelling founders outside of the binary success and into outlier status.
Another founder shared: “I am the underdog and have been told I always have had a chip on my shoulder. I love solving problems, and there are so many [customers] that I have come across where I have been able to solve their problems [through my company].” The motivation to solve problems and create a company where both customers and employees genuinely love doing business is deeply rooted in the founder’s identity as the “underdog.” A sense of challenge can be a powerful driver for founders, fueled by the times when they’ve been overlooked. Such heart has the potential to serve as fuel to break an existing mold, thought, or perception of success and prevent them from becoming disheartened.
It’s the blend of diverse and very real motivational factors that are the tipping point in propelling founders outside of the binary success and into outlier status.
The absence of a chip on the shoulder doesn’t diminish or lessen the potency of motivational factors. For instance, one founder with a stable family life was inspired by dissatisfaction with a predetermined career path. “No chip. I had a good family life. I have a supportive wife. I wouldn’t say that I faced any adversity other than the usual ‘that’s not how you do life’ unsolicited advice. I went to school thinking I was going to be a cubicle engineer my whole career, and after a while, it started to scare the hell out of me.” This revelation that life could become more than a routine ignited a spark, pushing this founder to break free from the expected and embrace the excitement of the unknown.
Motivational factors are incredibly diverse in nature and collectively underscore a crucial point: the journey to outlier status is not solely paved with external markers of success. Instead, it is inspired by the deeply personal internal fires of passion, ambition, resilience, and a commitment to self-improvement. Recognizing and understanding these motivational forces is integral to Redbud VC’s approach. It informs our strategy in identifying founders with deeply rooted motivations regardless of the driving force.
Conclusion
Our interviews with our portfolio founders found that seemingly small moments often play much larger roles in a founder’s journey toward success. Thus, there is no neatly packaged pattern that can guarantee the manifestation of an outlier founder, nor is there a combination of factors that can be matched. While many VCs continue to align with inherently flawed frameworks to find outlier founders, we at Redbud look to our founders for context on their experiences. We understand the journey to success is not a linear trajectory attached to your alma mater, geographic area, professional exposure, motivational factors, etc.; instead, it emerges from a tapestry of life experiences that have the propensity to cultivate an outlier founder.
Taking a note from Malcolm Gladwell’s book Outliers, we are betting that investing is about recognizing the unique blend of advantages, inheritances, and experiences that make each founder who they are. “In the end, the outlier is not an outlier at all; their success is a product of a web of critical elements deserving attention, understanding, and appreciation.” At Redbud, our commitment lies not in adhering to rigid patterns but in embracing the richness of individual stories and fostering the connections that propel outliers into existence.
Maria Heyen is an Associate at Redbud VC, a venture capital fund and studio investing monetary and social capital in early-stage tech founders.
Interested in more of Maria’s insights? Subscribe to her newsletter and follow her on LinkedIn and Twitter.