An Extended Reflection by Kam Phillips-Sadler

To know me is to know that I come from a unique rural upbringing that shaped my perspective in a manner that translates from pastures to pitches. Ranchers can spot a snake in the grass and smell bull sh*t a mile away- literally and figuratively. When I started business school, I steered away from sharing this and was further embarrassed to say out loud that I had a Social Work degree. The field is associated with case files and extracting individuals from systemic issues which, to the surprise of even myself, is an aspect of the role I've actually never experienced. After founding a social franchise model, the macro level coursework of the major was most closely aligned with my desire to build and scale organizations. I've later come to realize that being the only person at HBS and in every VC pitch with this background has put me at a strong advantage. "You have a third eye like no one I've ever seen..." said a fellow investor recently. Marry a cowgirl catalyst with training to evaluate body language, practice active listening and analyze non-verbal signals, and you find an unexpected recipe for early stage investing secret sauce. But to simply say, "I have an innate gift for picking up on that special ✨je ne sais quoi✨ in founders because I'm a founder who was born in the saddle and have a humanities degree..." feels insufficient. When I step back and decode the qualities of founders that have stirred up that gut feeling, they demonstrate three key attributes:

Informed Yet Imaginative Vision

The most captivating founders mortar a vision, brick by brick with every word of their pitch. As you ease on down the golden road they've paved, the path towards outsized returns takes shape. The founders that resonate most can articulate a clear vision for their product, the entire market landscape, and bring to life a clear picture of where the sector is headed down the line.

But watch out: founders can't simply be charismatic or engaging. Their ability to weave together dreams of an imaginative future must be paired with a business that demonstrates radical product market fit. They should have a toolbox that equips them to scale. Whether that is a novel sales conversion strategy, possession of market insights unique to them or proprietary distribution channels, many great founders with a captivating vision will play a tune that woos VCs like a Pied Piper and should not be assessed in a vacuum.

One holy grail visionary founder of today is Olamide Olowe, who upon first meeting, outside of a pitch setting, compelled me with an awe-inspiring insight into not only the long term outlook of her company, but her expectations for future financial activity in the beauty sector, her intention around future cap tables and even the societal impact a company like hers could be positioned to help usher in.

Rarely will you have the opportunity to meet a founder like Olamide, in the presence of whom you will lose track of all time and obligations, and should cut a check immediately. In most instances, of all of the strengths of founders expressed here, this is the trait that must be most carefully risk adjusted. Don't simply rely on the lure of imaginative vision. Recognition of this trait is step one to be paired with meaningful diligence and demonstrated sector brilliance on the part of the founder.

🧠 Gut check: Did the founder paint a vision of the future that made you want to do further research in a particular area? Perhaps they shared insightful stats that piqued your curiosity, challenged your preconceived notion or gave an informed glimpse into a sector that stretched your brain. While the unknown is uncomfortable, this prompt can be a good indicator of conversations worth further exploration. You should be prepared to be pushed mentally in the presence of extraordinary founders.

Cool & Composed Conviction

The very nature of fundraising is a brutal battle. As a Founder, you make your war plan, put your armor on and engage in a head to head duel that is statistically designed for you to end in defeat. Day after day, you zoom into the arena and repeat the same battle cry you've expressed ad naseum. Despite this, there are founders that, regardless of what pokes and prods come their way, are relentless in their belief of the opportunity ahead. Their conviction is not tampered by criticism or VC doubt and their passion doesn't fade in the face of reluctance.

These founders tend to be quick with their answers, sharp with knowledge of their space and will surprise you with "hot takes" that illuminate a prospective strategy in the future.

I'll never forget how evident it was that Conner Sherline's time in his previous roles had so perfectly equipped him with unique insights to build his concept of a partnership platform for modern brands. We were one of 25 meetings he had scheduled that week, yet with confidence and facts, he rhythmically navigated our queries, asserted his wedge into the market and drew thought provoking industry parallels that drove his points home.

Oddly, I remember the exact moment that I knew I wanted to invest. "You heard it hear first!..." he exclaimed, before regaling us with an informed vision of the future of customer acquisition that made me reach for my invisible checkbook.

The best of these founders, like Conner, recognize a large market opportunity and have a strong hunch as to the ideal plan of attack, yet are agile and modest enough to concede that the grander vision may change over time. Their product roadmap is well thought out yet open to evolution. They are steadfast but not stubborn. Assured but not arrogant. Passionate but not pugnacious.

🧠 Gut check: As VCs, we pound the table for ideas. Do you see that spirit in the founder pitching you? Is the founder confident yet calm in their approach? Conviction is one area where body language can be meaningfully telling. While we want a founder who would pound the table, we don't want them to do so literally, nor do we want to see agitation. Look for founders who are composed and seemingly unbothered. The reality is, for these founders, regardless of your opinion, they're betting on themselves and the market and will pursue this regardless of your check.

Gracious Humility

Founders should have a grounding compass, not a printed set of MapQuest directions that they blindly adhere to. It is the inevitable nature of the sector that founders will need to be amenable to shaping their end result on the quest to finding product market fit. Founders who acknowledge their shortcomings on the path to identifying this fit evoke a trust that should be heeded.