Olajuwon Ajanaku and Earl A. Cooper—both 34 and Morehouse College alums—are driving an expanding cultural revolution with their Eastside Golf lifestyle and fashion brand. Launched in 2019, the company brings youth and hip-hop swagger to traditionally staid golf courses.
The duo’s creative sportswear is just a piece of a larger mission to attract young African Americans to golf and bring greater diversity to the sport.
“When I first started playing golf as a child, golf wear was all khaki pants and a white Polo shirt—our culture and fashion were missing, and I didn’t enjoy it,” says Ajanaku. He was introduced to the sport at an early age and later aspired to a pro career. Unable to garner sponsorship, he turned to entrepreneurship to finance his dream.
The two have also used Eastside Golf to not only drive their business passion on the greens but also use the venture to get on deck to master the lessons required for long-term financial success.
Eastside Golf started with Ajanaku’s self-designed logo for his golf gear – a cool graphic of a Black golfer based on himself, with a club raised and a swinging gold chain. His friend and Morehouse brother Cooper, a PGA professional and Eastside Golf co-founder, immediately sensed that the logo was lightning in a bottle.
The response from the tee box has been strong. Ajanaku says he shipped the first 3,000 orders from his apartment in Detroit, where he lived during the company’s inception. At the same time, Ajanaku and Cooper forged a strong partnership based on their love for the sport and their desire to bridge the traditional golf world with the culture. “I think we’re well qualified to do just that because of our common experience,” Cooper says. “We both started playing golf at six years old and went on to compete at the junior and collegiate levels. Something that we’ve talked about forever is that golf needs culture…golf needs representation. We’ve worked together and figured out ways to align passion with purpose. That separates us from any other apparel business or golf company.”
Both partners have finance backgrounds and learned about money management and budgeting early on.
For instance, Cooper gained his introduction to personal finance and business while in grade school. He and a friend realized they could buy a box of brownie mix for a dollar, sell the cut-up baked product for 50 cents each, and earn a tidy profit. He’s been focused on figures ever since.
That’s not to say that Cooper hasn’t had to learn valuable lessons from financial challenges. “I was introduced to saving and investing really significantly around college. Because, again, you had an allotted amount of money, and it had to stretch. I can also remember my first credit card. I went off to spring break and ran it all the way up. I’m fighting this hole, right, because I didn’t have the steady income coming in, he says. “But as I progressed. It taught me how to really learn how to manage finances by setting a budget, which we do obviously for the company, but that’s something that we need to do with our own personal finances.”
Ajanaku, who graduated from Morehouse with a degree in accounting, worked in regional sales management for eight years after graduation. He says money management was vital once he launched the business since “I started off with my savings, a credit card, and my cryptocurrency [account].” With limited funds, he had to be extremely precise about managing inventory – how quickly he sold items and when he had to replenish stock across an array of different sizes. “I didn’t do a very good job of that at the beginning. But now, we’re hiring a fractional accountant. Hiring people [who] can actually help us figure [out] what those sizes are that we need. Learning from our mistakes is definitely helping us move forward.”
The company bootstrapped for a year and a half, but it was clear to Ajanaku and Cooper that they couldn’t sustain the business on savings and sweat forever. It was time to raise capital to promote business growth. The funding avenue they chose was a SAFE note – a Simple Agreement for Future Equity.
For many startups, SAFE notes are a simpler, more “founder-friendly” alternative to more traditional funding sources and represent a simpler alternative to convertible notes and other more conventional routes to funding. A SAFE note is a legally binding agreement that allows investors to buy future shares at a set price. Like convertible notes, SAFE notes include valuation caps and discounts but provide the founder with a more straightforward formula and greater flexibility.
“You still need to hit your valuation threshold, but there are safeguards in it,” says Cooper, adding that the SAFE note documentation opened the company to the kinds of investment opportunities they weren’t prepared to take advantage of in the earlier stages of the company’s development. “We had the desire, we had the intensity, but at the end of the day, you needed the paperwork.”
Another critical challenge for growing e-commerce retailers like Eastside Golf is keeping pace with tax requirements across the many states where the business is bringing in sales. Cooper stressed the importance of enlisting a CPA to ensure tax compliance and conducting a nexus study to determine when earnings hit tax thresholds in each state. “If you don’t do the study, it’s easy to fall behind in your tax payments and not realize it until it’s time to file.”
The hard work and lessons learned have produced impressive dividends for the company. The founders recently announced that Eastside Golf secured an investment from the PGA, marking the first time the golf association partnered with an apparel company. “To have that credibility, to have the game’s governing body decide, ‘We’re going to park our money with you” – that’s huge,” Ajanaku says.
The company continues to grow. Their focus on promoting diversity in golf has bolstered its partnership with NIKE’s Jordan Brand, including its Change 1961 collection—inspired by the year the ban on Black golfers earning tour cards and participating in competitions was lifted in professional golf.
Adds Cooper: “Having a partnership like that puts us in a unique position to get young people back to the game.”
The two are also focused on building generational wealth as they build the business. “The advice that I would give to other entrepreneurs as they develop their own personal finance goals, and even for the business, is you need to start preparing today. I know it’s a cliché, but you need to be looking [at] ‘where I am today is, not where I want to go.’ In order to be prepared with where you want to go, there may be financial advisers that you need to start talking to now.” It doesn’t necessarily mean you need a ton of money, but at least you’re prepared, as Ajanaku mentioned earlier when the moment does arise.
The partners are still focused on their personal finances. Cooper, who manages his money from a conservative standpoint, says: “We need to be saving. We need to be thinking about contingency plans. One of the things that I’ve always done is never make a move that can affect my lifestyle.”
Asserts Ajanaku: “At the end of the day, what do you want to do with your life? That is what the money is for. You can do your job for 40, 50 years, then retire, and then you can go on to your retirement, or you can take that money and actually invest it into your dream and make that retirement even so much larger.”
Swing by swing, Eastside Golf continues to build bridges between words and bring youth and cultural authenticity to professional golf.
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