From Westlands High-Rise to Rock Bottom: Bobby’s Raw Lessons on Redefining Success

 

I’ll be honest: I was nervous. Not the butterflies-before-a-first-date kind of nervous, but the sweaty-palms-what-if-this-goes-wrong kind of nervous. And no, it wasn’t the elite police officers stationed outside Westgate Mall that made me feel that way. These guys looked like extras from an action movie, stone-faced, guns holstered but itching for action—the kind who could arrest you just for blinking suspiciously. But my anxiety wasn’t about them. It was about the coffee date that awaited me.

I was about to meet Bobby.

Now, Bobby wasn’t some old buddy or long-lost cousin. He was a stranger plucked from the infamous Founders Battlefield WhatsApp group. If you’ve never had the pleasure, or trauma, of being in that group, let me paint a picture. Imagine a gladiator pit where the weapons are business theories, startup jargon, and the occasional philosophical grenade. It’s the kind of place where founders duel with “synergies” and “scalability,” and you risk being verbally KO’d before your morning tea. Honestly, it’s more entertaining to spectate than to participate.

So, when I posted a request for a speaker for The Men’s Group, I braced for silence. I’ve run WhatsApp groups where you could announce your engagement, and the only reply would be the lonely “👍🏾” emoji from an auntie in a different time zone. But within minutes—ding!—A message came through.

“I’ll do it,” wrote Bobby.

Now, at this point, my brain had questions. Who is Bobby? Why is Bobby volunteering? Is Bobby one of those people who wears sunglasses indoors like the cops outside? But Bobby quickly disarmed me. He sent a link to his recent Financially Incorrect interview, which, as it turns out, was trending. I clicked.

Within minutes of watching, I was hooked. Bobby was raw, funny, and brutally honest. He wasn’t selling dreams; he was dissecting them. He spoke like a man who had been through life’s blender and lived to write a recipe book about it. Immediately, I knew I had to meet this guy.

Which brings us back to Artcaffe.

Inside, the air was thick with the intoxicating aroma of roasted coffee. Soft jazz floated from the speakers, trying to convince me that everything would be fine. Ceiling plants stretched across beams like acrobats on holiday. I sipped my cappuccino and rehearsed possible greetings: too formal, too casual, too desperate. Then the door swung open, and Bobby walked in.

And suddenly, I knew this was going to be interesting.

He looked exactly like his video version, except now I could read the small details. The way his eyes flicked around the room, scanning, calculating. His smile seemed both warm and battle-hardened. This was a man who had faced storms and brought back souvenirs.

We shook hands. His grip was firm, reassuring, the kind that said: “I’ve been through hell, but I can still afford to smile.” Within minutes, we were deep into conversation. Bobby didn’t just talk; he painted stories. He didn’t just answer; he questioned. He was part philosopher, part stand-up comedian, part negotiator. Honestly, I half-expected him to whip out a whiteboard and start charging me for a masterclass.

Two days later, he was standing in front of our men’s group, ready to deliver his talk: The Broken Dreamer—a romantic title for a brutal story.

He told us about his glory days: owning a prime building in Westlands, running a multimillion-dollar company, living the high life. Then came the crash. The debt. The divorce. The suffocating despair. At one point, he confessed he considered suicide, but then chuckled and said, “I was too chicken to go through with it.” The room laughed nervously, but in that laughter was power. He had stripped fear of its authority.

His mantra was simple: Awareness. Accept. Act.

Be aware that you always have choices. Accept that your world has changed—denial doesn’t pay bills. Act, even if all you can manage are baby steps.

What struck me most wasn’t just his resilience, but his emphasis on community. Bobby said, “Do you know I was never blacklisted on CRB, despite my massive debts? Relationships saved me.” He explained how friends gave him space to cry, to vent, to be vulnerable without shame. That community was his lifeline.

Then came his final punchline:

“What is your definition of success?”

Silence. You could have heard a WhatsApp notification ping in that room. We realized most of us were chasing borrowed dreams. Skyscrapers. Cars. Headlines. But maybe success is simpler. Maybe it’s sending your kids to school. Maybe it’s having free time. Perhaps it’s about growing old with dignity and good health. Maybe it’s not living in Naraka.

Three Lessons

1. Vulnerability is power. Asking for help doesn’t make you weak; it attracts the right people.
2. Isolation kills. Build your tribe. When storms come, they’ll be your oxygen.
3. Define success before it defines you. If you don’t write your own script, society will sell you one you don’t even like.

Call to Action

Here’s my nudge as your coach: Don’t let Bobby’s question float away. Write down your definition of success this week. Share it with one trusted person. Then take one action—just one—that pulls you closer to it.

And if you feel stuck, that’s where I come in. I help strip away the noise, clarify your vision, and align your habits with your own definition of success. Don’t wait for Naraka. Start now.