Kingside in the Winner’s Circle: It’s Not Just the Horse and the Jockey—It’s the Trainer
A few decades ago in the early days of venture capital, , my longtime colleague and dear friend Atty. Joseph Bartlett, – a legal pioneer in the venture capital space – wrote a white paper that I still think off as it still echoes through the investing world and has been reaffirmed many times as I have witnessed in my 4+ decades of experience : “It’s not just about the horse, it’s about the jockey.” Joe’s point was simple —yes, a promising business model (the horse) is indeed critical. But equally vital is the management team (the jockey) tasked with execution. The best model in the world won’t go far without a talented rider in the saddle (but still not yet fully experienced).
Joe was no ordinary lawyer. He was president of the Stanford Law Review and a law clerk in the United States Supreme Court for Chief Justice Earl Warren (1960 term). More relevant to my career, Joe served as a mentor and he was an icon in the venture capital space. Joe literally wrote the defining authoritative book – the Encyclopedia of Private Equity and Venture Capital– that guided the venture deal world, particularly in that era. Joe was considered one of the leading teachers and practitioners in the field of venture capital, focused on emerging companies, IPOs, corporate governance, corporate restructurings, private equity finance and buyouts. Joe advised numerous large and small companies on capital raising and M&A, and was notably counsel to Bain Capital and Chemical Ventures. The Daily Deal characterized Joe as follows: “If someday a supreme court for venture capital were to be created, Joe Bartlett would be the chief justice.” Joe and I served together as directors on a large NASDAQ public company board. I learned a lot from Joe.
Joe passed away in 2019 and while views remain true, the analogy must evolve just as the world of high stakes professional thoroughbred racing itself has evolved.
Today, if you attend the Kentucky Derby, Preakness, or Belmont Stakes, you’ll see that success is no longer defined solely by a champion horse or an elite jockey. You’ll also see a third vital figure standing in the winner’s circle: the trainer.
In high stakes thoroughbred racing, names like Bob Baffert, Brad Cox, and Chad Brown are as celebrated as the emerging horses and the premier jockeys. These trainers impact the unseen variables to a racing fan — the long multi-phase conditioning, distance and turf strategy, in-race pace timing, mental readiness. In many cases, it is this third party – the trainer – that is the defining influence that turns a good horse into a great winner.
The Business Parallel for Lower, middle market companies
In the world of emerging, lower middle-market businesses, the same three-part structure should be applied :
– The horse is the business itself— the investment appeal and success potential .
– The jockey is the management team—hard-working, skilled, motivated, hands-on capable.
– But the trainer—that’s often what’s missing. – this is where Kingside Partners steps in.
Readying the Young Horse—and the young company that seeks to scale
In high level thoroughbred racing, no horse simply wakes up ready for the Kentucky Derby. The journey begins long before. A talented young thoroughbred must be carefully developed as a two-year-old—tested at lower levels, conditioned for discipline and distance, and gradually introduced to higher-caliber competition. A seasoned trainer is essential during this phase, ensuring that raw potential doesn’t become wasted promise. They manage setbacks, choose the right prep races, and pace development so that the horse peaks at the right moment—when the stakes are highest.
The same is true for a young company. Early-stage businesses are full of promise but face countless obstacles that can derail growth—misaligned priorities, flawed business decisions, incomplete go-to-market plans, fragile financial controls, and lack of institutional readiness and governance. This early phase demands a steady, experienced hand to help guide the path.
At Kingside Partners, we serve this role—being hands-on, adding bandwidth, bringing C-suite experience and seasoned, battle tested advice from having sat in the seat. Helping the business and the management team scale – getting ready for the equivalent of the Triple Crown season: business affairs, capital formation, marketing, financial management, measured capital deployment in pursuit of value accretion and exit-readiness.
Kingside Partners: Your Strategic Trainer
Like a trainer, we complement the team effort – we don’t seek to displace the jockey or impair the horse. We’re here to help win . We work shoulder-to-shoulder with equity sponsors, owner managers and the management to deliver business acumen, performance improvement and corporate finance insight. Whether it’s preparing for a transaction, accelerating growth, or solving operational hurdles, we serve as the third party helping to ensure every part of the team is aligned and primed for success and the winner’s circle.
