Reframing Failure: What I Learned from My Startup Experience
“Failure can be a lousy teacher because it seduces smart people into thinking their decisions were terrible when sometimes they just reflect the unforgiving realities of risk.” —Morgan Housel, The Psychology of Money
During my journey to becoming a brother of Alpha Phi Alpha Fraternity, Inc., we learned a lot of poems—words that carried deep meaning and wisdom.
Throughout my time building OjaExpress, I found myself leaning on those poems again and again, drawing strength from their messages. One of my favorites was If by Rudyard Kipling, and these lines, in particular, resonated with me the most during the highs and lows of my entrepreneurial journey.
These words have never felt more real to me than they do now, after my journey with OjaExpress. Triumph and disaster—both are fleeting, both are teachers, and neither should be mistaken for the final chapter.
Before I dive deeper into my experience, I want to acknowledge that this post is, in many ways, therapeutic for me. I’ve been overwhelmed by the outreach—messages, emails, and texts. To all of you, I say: don’t worry. I fully intend to reply to everyone in due time. This post is part cathartic, part memorializing of my journey, and also a message to future founders, sharing the lessons I’ve learned along the way.
Why I Started OjaExpress
For most of my career, I was firmly planted in the world of healthcare. I’m a registered nurse by background and hold a master’s degree in healthcare administration.
Over the years, I worked across various sectors of healthcare—hospitals, long-term care facilities, and ambulatory services—leading teams, managing operations, and growing comfortable in my role as a healthcare administrator.
I was doing well. I had a good salary, financial security, and a lifestyle that could be described as upper-middle class. I was also deeply involved in my community, serving on boards and leading the Nigerian American Professionals Association. Life was stable, and I was on a somewhat predictable career glide path.
But despite the comfort, something gnawed at me.
OjaExpress was born out of both personal experience and observation. As a first-generation Nigerian-American, I noticed a growing immigrant community around me, particularly a professional class that, despite its size and influence, was largely underserved. There was a dearth of services catering to this group—people who longed for access to the foods and products that reminded them of home but were unable to find them easily in mainstream stores.
The idea was simple but powerful: OjaExpress would bridge that gap, creating a platform that made ethnic groceries accessible to everyone. It wasn’t just about food; it was about culture, identity, and making people feel at home, no matter where they were.
I believed business could be a force for good, something that could benefit the community while also being profitable. And with that vision in mind, I left the comfort of my healthcare career and leaped into the unknown world of startups.
The Highs, Lows, and the Dark Days
In the early days, things looked promising. We got positive feedback from customers and local grocery stores. We were building momentum, and there were moments when it felt like we were truly making a difference. Every sale, every partnership was a small victory, affirming that we were onto something.
But there were also lows—real, painful lows. Running a startup meant pouring all my time, energy, and resources into OjaExpress, often at the expense of everything else. Funding was a constant struggle. The work hours were relentless. And slowly, the sacrifices started to pile up.
There were moments when I wasn’t just broke—I was broken. I went from being a cheerful giver to feeling like a penny pinching pauper, forced to count every dollar because of the financial sacrifices I felt compelled to make for the company, all in the hope that everything would turn out right and lead to future success.
The weight of those burdens made it hard to enjoy even the smallest moments with my loved ones, like treating them to something as simple as ice cream or pizza. That weighed heavily on me. Even with my friends, the carefree nights out became a thing of the past. I had to plan weeks in advance just to go out because I simply couldn’t afford to anymore. I became distant—not because I wanted to be, but because I didn’t have the means to participate in the life I once knew.
I had a comfortable life before I ventured into entrepreneurship. I could have stayed in healthcare, living a solid middle to upper-middle-class lifestyle without ever worrying about making ends meet. But I took a risk—a big one—because I believed that fortune favors the bold. What I didn’t expect was how deeply the lows would affect me—not just financially but mentally.
No one really talks about the impact on your mental health that being a founder can take. Therapy was never in my vocabulary until I became a founder. As a Black man and the child of African immigrants, we’re often taught to brush things off or pray about them. But the mental toll of being a founder is real, and it’s something that isn’t discussed enough. For me, therapy became a necessary tool in navigating the emotional strain that comes with entrepreneurship.
One day, I was walking by the Merchandise Mart in Chicago, a place I’ve spent a lot of time in over the years. As I looked over the Chicago River, anxiety suddenly hit me. How many people had I let down? Was I too optimistic? Where did things go wrong? My investors believed in me. Some customers relied solely on OjaExpress to get their groceries—I’d seen their children grow. In that moment, it felt like the weight of the world was on my shoulders.
That’s exactly what it felt like. I had poured my life into OjaExpress, and now, I was staring at what felt like the broken pieces. As an OG millennial, I grew up in an era where you took your L’s on the chin, but this one felt different. This felt like a concussive body blow, the likes of which I’d never experienced.
Earlier in my career, I worked as an ICU nurse. I’ve literally seen it all—disease progression, death, the hardest moments of life. Every day I walked onto my unit, someone’s life was in my hands. In that moment by the river, I had to remind myself: no one has died. There are losses people don’t come back from, and this wasn’t one of them.
The Decision to Let Go and Reframing Failure
“If you can make one heap of all your winnings And risk it on one turn of pitch-and-toss, And lose, and start again at your beginnings And never breathe a word about your loss;” —Rudyard Kipling
This verse captures the essence of the decision I had to make. I had poured everything I had—my time, energy, finances, and heart—into OjaExpress. But despite all the effort, it became clear that the business couldn’t go further. After giving everything I had to the business, I had to make the painful decision to let go and close its doors. At first, it felt like the ultimate failure, and I questioned every decision I made. I wondered, Where did I go wrong?
But here’s the thing: failure isn’t always a reflection of poor decisions. Sometimes, it’s just the brutal reality of risk. Entrepreneurship is unpredictable, and despite our best efforts, things don’t always go as planned.
Winning in business is stacking more wins than losses. But some losses have greater magnitude than individual wins. One major L can wipe out 20 wins.
And more importantly, “as much as we recognize the role of luck in success, the role of risk means we should forgive ourselves and leave room for understanding when judging failures.” This became key to how I reconciled with the outcome of OjaExpress. I’ve learned that we have to leave room for forgiveness when failure strikes, not just for others but for ourselves.
Finding Gratitude
After the initial shock, I started to feel a sense of gratitude. I began listing out the things we did right, the things that many people may never see. The interns who worked for us went on to do phenomenal things. The vendors we partnered with created amazing content and products. The stores we worked with were elevated through our platform.
More than that, due to the places OjaExpress has taken me and the people I’ve met, my mental expanse has widened. I dream bigger. My perspective on the world and the good that can be done has actually increased. I now have a greater appreciation for what’s possible, and that has been one of the most rewarding outcomes of this journey.
The painful part is that we didn’t have enough to keep going, but there are seeds of goodness we planted that I believe will have a lasting impact. For that, I am beyond thankful.
What I Gained
What I gained from this experience wasn’t just business acumen or resilience, but an expanded network. I met people I never would have encountered had I stayed on the healthcare administration trajectory I was on. From investors to entrepreneurs, from tech leaders to cultural champions—I learned from all of them.
And beyond that, I gained an extended family who I love dearly (and sometimes vehemently disagree with—if you follow me on social media, you’ll see those disagreements 
). I now have more brothers, sisters, aunts, and uncles who have been there to support and mentor me over the years. Their love and support cannot be measured, nor can it be adequately described in English. I am endlessly grateful to them.
I also want to take a moment to express my deepest gratitude to our early investors. You believed in us when all we had was a vision—a dream that, on paper, might have seemed far-fetched or unattainable. But you saw potential where others saw risk, and you trusted us to turn that potential into something real.
Your belief in our mission, your willingness to invest not just financially but emotionally in OjaExpress, meant more than I can put into words. Even in the toughest times, knowing we had your faith behind us was a source of strength. Thank you for standing with us and for daring to dream alongside us.
Lastly, I want to shout out my co-founder, Fola Dada. We fought, we disagreed, but you stayed committed as long as you could. I appreciate your sacrifices and effort. The journey wasn’t easy, but your dedication through the ups and downs didn’t go unnoticed. We might not have achieved everything we envisioned, but your presence made the fight worthwhile.
Lastly, I also want to give a huge shoutout to my family and friends who really held me down. The calls to ask how I was doing—and not letting me get away with a simple “I’m fine”—and the countless random acts of kindness and love went a long way. You were there for me when I needed it most, and I will always be grateful for that.
The Opportunities We Created for Others
Even in failure, there were successes. OjaExpress may not have lasted, but it created opportunities for others—opportunities I’ll always be proud of. We employed people who might not have had jobs otherwise, connected small ethnic grocery stores to a broader customer base, and made it easier for countless families to access the foods that reminded them of home. We built community.
That impact is real, and it’s something I’ll carry with me as one of the most meaningful outcomes of this journey.
Was It Worth It?
So, was it worth it?
Yes, without a doubt. I sacrificed a lot, and I experienced immense pain and hardship. But the personal growth, the resilience I developed, and the impact we made on others make it worth it. OjaExpress may not have been the success story I imagined, but it shaped me in ways I’ll never forget.
My advice would be to stay grounded in your values and conviction. Assess the sacrifices, and determine if it’s worth it to YOU. Everyone’s conviction and values aren’t the same, so make sure you’re in tune with who YOU are. I was willing to die out of a false sense of honor and bravado. But today, I live to fight another day—and that’s the real victory for me. That’s what winning looks like today.
OjaExpress, as we know it, may be gone in its current form, but the spirit of OjaExpress thrives and resides in the people, businesses, and communities we supported—and the people we hopefully inspired along the way. Who knows? Perhaps one day OjaExpress will rise again, like a phoenix, transformed into something new.
by Boyede Sobitan, former co-founder of Oja Express
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