My inspiration in leading Guava’s seed round
April 7th 2017, was my first weekend at Pelican Bay State Prison, California’s only “SuperMax” facility and by the 2nd day, my brain was running a million miles a minute. I was surrounded by some of the most incredible high-potential people, many of whom were serving life sentences and even some serving “LWOP” (Life Without Possibility of Parole) and I was quickly connecting the dots in how a number of societal factors served as massive inhibitors to the potential of men who grew up as almost every single person I have ever met in prison has grown up: In communities that were shaped into being by policies designated to isolate people based on their race and socieeconomic standing, where most men currently and formerly incarceated have also experienced both domestic violence and community violence and where selling drugs or becoming a professional athlete or successful musician were the only paths seriously considered for their way out of impoverishment.
Other than having our two children, that weekend jolted a new level of ambition and determination inside of me. I knew that no matter how wealthy we are and become, that our family would not be able to fund all of what needs to be funded in America to ensure that every American - especially those who have had multiple levers of power rigged against their success - to operate on a level playing field.
Some of you might know that my first and still held investment thesis of mine has been the “Survival Economy” driven by a belief that America as both a society and an economic engine of growth has been suffering from a life threatening illness for years and that I’d at least seek to find the right palliative care whilst also searching for the cure but my time in prison made me start to hone my search for the types of investment opportunities that either help pool people climb the economic ladder and/or prevent people from falling further.
2020 marked the beginning of a new chapter of my investing career where I decided to focus the majority of my new investment activity on formative founder bets. That is to say, find a founder or founders as early as possible in their entrepreneurial journey and to write them their first check or first big check and partner with them in helping them build their team and go-to-market. When starting with this investment focus, I knew that one of the founders I wanted to back was a founder who would build the largest financial institution for America’s Black business owners. I combed through my entire network and the network of others I knew to find anyone that was already starting to think about this opportunity. After almost a year of searching and interviewing several compelling entrepreneurs, I met Kelly at the end of 2020 and instantly knew in our first meeting that she was the entrepreneur I was searching for and led Guava’s pre-seed round last year.
I make only a small number of new investments a year and of the companies in a year that I have the highest conviction are likely to live up to their potential, try and also lead the seed round. Few other investors, especially those who haven’t grown up in or who have close friends and family who live in the communities in which Guava‘s customers are most heavily concentrated can truly understand the magnitude of Guava’s appeal and I’m so excited for Kelly and her team to show the investment community just how big this business will become.
With today’s funding announcement of Guava’s seed round, I want to be more vocal in making it clear that I am biased toward underrepresented founders and especially to market opportunities that serve the millions of Americans who many people overlook as valued customers and that my DMs from my LinkedIn profile are open and that I provide very specific instructions on how to write the cold email that has the best chance at getting my interest.
I am grateful to Kelly that I’ve had the opportunity to lead this round and that this round has brought together a great group of investors who are similarly excited about what Guava’s success can look like, not just for financial returns but for helping the millions of Black business owners thrive and just as importantly, for also showing that the next big venture scale companies are in using software and the power of networks to elevate groups of people that individually have struggled to have their voices heard. Indeed, I believe that we are in a new era of network formation in which the balances of power can be transformed like at no time in human history. I am particularly interested in finding founders who are thinking about the power of this opportunity so please reach out!
