Lessons from the Trenches: One Founder’s Candid Look at Bootstrapping

Starting a business is often romanticized as a journey filled with exciting milestones and instant success stories. Yet, as most seasoned entrepreneurs will attest, the reality is far more complex and challenging, particularly when you decide to bootstrap your business. Reflecting on my own journey with Equifund, I aim to shed light on the trials and triumphs of entrepreneurship, especially for those who, like me, choose not to rely on outside funding.

My entrepreneurial story didn’t start with an invention or a groundbreaking technological breakthrough. Instead, it began with 15 years of hands-on learning in capital markets, working closely with entrepreneurs, investors, and bankers. This experience allowed me to identify a critical void in financing companies: building healthy capital stacks and navigating the public offering process. By the time I founded Equifund in 2016, I was deeply familiar with the landscape and felt prepared to tackle the challenge.

The problem I was solving was so clear to me. What could go wrong?

Embracing the Entrepreneurial Challenge

Unfortunately, confidence in my business model didn’t shield me from the harsh realities of starting up. I was not licensed, did not have a college degree, could not code. I also did not have a business partner. My first pitch was not to investors or potential clients; it was to my fiancée, convincing her to delay our wedding plans until Equifund was up and running — a promise that took significantly longer than the anticipated six months to fulfill.

The early years were grueling. Despite securing the necessary approvals to operate as a funding portal where entrepreneurs and investors could connect and transact, attracting those people proved to be a Herculean task. I felt like I was selling the first fax machine: “If you buy this machine, trust me, I will sell another one and you will be able to use it.”

With no revenue three years in and an ever-increasing pile of expenses, my personal finances took a hit. Loans replaced savings, and credit lines were stretched to their limits. Yet, the belief that Equifund could bridge a vital gap in the market kept me going. Didn’t investors want to find new and exciting companies to own a piece of? Weren’t entrepreneurs tired of the golden handcuffs of venture capitalists and bankers?

Navigating Tough Financial Times

Managing finances during this period was an exercise in frugality and creativity. When you invest in your business with your own money rather than investment dollars, you pay attention to every penny. Negotiating every expense and extending payment terms wherever possible became second nature. My family and I lived a minimalist lifestyle, relying on the support of friends and relatives to make ends meet.

The so-called J-curve of business growth — a period marked by initial investment losses before the eventual upturn — was a dark and isolating time. Doubt crept in with every setback, making the journey seem insurmountable. The motivation to succeed for my family provided a beacon of hope. I doubled down on my efforts, making more calls, writing more content, and networking tirelessly. It was a brute-force strategy, devoid of any fairy-tale twists, but it was effective.

Looking back, I realize the importance of having a mentor during those challenging times. Someone who could offer guidance, share their own experiences, and validate the struggles inherent to the entrepreneurial grind. While I eventually found success through perseverance, strategic partnerships, and the unwavering support of my wife and team, I often wonder if the journey could have been less daunting with the right mentorship.

To fellow entrepreneurs at any stage of their journey, my advice is clear: If you are committed to bootstrapping your business, be prepared for the long haul. Understand that success rarely comes overnight, and that the path is often fraught with challenges that test your resolve. But also know that with perseverance, a supportive community, and strategic thinking, it is possible to navigate the journey and emerge victorious.

Entrepreneurship — especially when bootstrapped — is not for the faint of heart. It requires a blend of unwavering conviction, strategic acumen, and the ability to endure through the toughest of times. For those embarking on this journey, remember that while the challenges are many, the rewards of building something from the ground up and on your own terms are immeasurable.

Contributed to EO by Jordan Gillissie, the founder and CEO of Equifund, an alternative investment platform that provides retail investors with access to emerging companies. Registered with both FINRA and SEC, Equifund is dedicated to empowering entrepreneurs and educating investors. With his extensive industry experience and visionary leadership, Jordan has established Equifund as a pivotal player in disrupting middle market investment banking. He is committed to fostering an informed, engaged investment community, aligning business growth with investor education. Prior to founding Equifund, Jordan founded capital markets consulting and investor relations firm Novea Capital Inc in 2009.

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