How ‘nice guy’ Tobi became Mum’s hero

As promised, today I bring you the underdog story of Tobi Chapman.

One that shakes me to my core and brings tears to my eyes as I write it.

Tobi isn’t just another name or fleeting success.

He’s one of us. A warrior who has risen through the heart of the David to Goliath community, clawing his way from the shadows of doubt towards a life of undeniable impact.

It’s not a fairy tale. More a relentless battle of will, bravery, and unshakable purpose.

A defiant roar from a wounded lion who just wanted to become his mum’s hero. 

Prepare to be inspired, humbled, and reminded of what’s possible when you refuse to quit.

This is the Underdog tale of Tobi Chapman.

And it starts with a life altering accident…

Every hero’s journey starts with a breaking point.

For Tobi, it came on a mountain-biking trail.

A split-second miscalculation.

A slick patch of mud, a razor-sharp slate, and the sound of his knee smashing, slicing, snapping.

Then the aftermath:

• A completely ruptured patella tendon.

• Five surgeries across 6 weeks of hell.

• Infections clinging to the metal screws and implants in his knee.

The doctor told him straight: “We can’t guarantee you’ll keep your leg.”

Now imagine this for a second…

You’re Twenty years old.

You’ve followed the rules, earned your place at university for next September, and set yourself on the steady, conventional path toward becoming a veterinarian.

And suddenly, you’re alone in a sterile hospital room. The pandemic has locked the world down.

No visitors. No roadmap. Just endless IV drips, and blood transfusions.

The one thing you took for granted – your ability to stand, to walk, to move – dangling by a thread.

In the abyss, surrounded by nothing but uncertainty, the questions thundered through Tobi’s thoughts:

• Is this who I’m meant to be?

• What if I never get back to "normal"?

• What if… I don’t want "normal"?

But what haunted him the most wasn’t the uncertainty or the isolation - it was the weight of his mother’s sacrifices.

She was the warrior who never stopped fighting. Through a brutal divorce, she had clawed her way forward, juggling multiple jobs, sacrificing sleep, energy, and dreams - all to give him and his siblings a shot at something better. . 

And now, here he was - the promise he’d made to himself to give her the life she deserved, feeling impossibly out of reach.

It was at this moment that something stirred.

Not clarity. Not hope.

Just a fire that whispered ‘this isn’t over’.

But would it be enough? 

For months of recovery, Tobi was locked in stillness, staring at a blank slate.

As he replayed his mother’s sacrifices over and over again, he limped into the online world like a wounded lion, scavenging for opportunities.

Odd jobs, scraps of income, freelance copywriting gigs.

The quiet, diligent kid, the bookworm who always followed the rules, was now rewriting them out of necessity. 

Hustling. Adapting. Fighting.

By September 2022, Tobi was back in the system, thinking that university would be the answer.

“Get your degree, keep your head down, and follow the well-worn trail to a safe, steady job.”

At first, he convinced himself he could adapt.

The course itself wasn’t the problem; it was everything else.

• The halls of predictability.

• The hum of conformity.

• The culture where ambition was a whisper, drowned out by the monotony of student life.

And by December, the cracks began to show.

Every day, the claws of dissatisfaction tore deeper into his soul. He hated it.

But hate alone wasn’t enough to make him leave.

Fear held him captive: fear of the unknown, fear of stepping into the chaos, fear of failing and crawling back to the very cage he wanted to escape.

He knew he needed to jump but he couldn’t bring himself to take the leap of faith.

So he waited. And waited.

For months, Tobi wrestled with his instincts, the roaring voice inside him growing louder, until finally, in November 2023, he couldn’t take it anymore.

The dam broke, and he walked away from university on a temporary leave of absence.

Hitching into the wilderness carrying nothing but dreams and a fragile spark of determination.

His small E-mail Marketing agency, Everboost, became his battleground.

Yet it was barely alive…

Projects trickled in like drops of water and became a temporary reprieve. A flicker of light quickly swallowed by the looming darkness.

Around him, other online entrepreneurs his age thrived – building empires, landing deals, and moving with the aura of giants.  

Meanwhile, Tobi fought just to keep breathing.

He saw failure in the mirror, heard it in his own thoughts as he was mocked by his own mind:

• What if this doesn’t work?

• What if I’m not enough?

• What if I have to crawl back to the life I just walked away from?

The jungle doesn’t welcome the weak.

But remember, Tobi wasn’t just fighting for himself…

He was fighting for his mum.

It was time to become her hero.

By April 2023, desperation drove Tobi to take a gamble that could either save him or sink him.

His solution was Spending £900 - money he didn’t have - on a LinkedIn branding course. 

The allure was undeniable: shortcuts, fast wins, effortless success. You’ve heard it all before.

At first, it seemed like the lifeline he needed. The course turned into what appeared to be the perfect partnership.

But as the months passed, the illusion of alignment began to crumble. 

Their visions for the agency couldn’t have been more different.

Eventually, they parted ways, splitting the clients between them. 

For Tobi, it felt like watching his hard-earned progress sail away with someone else.

The walls were closing in once again.

But this time, something was different. 

He learned one of the most critical lessons of his journey:

Trust is a weapon that cuts both ways. Misplace it, and you’ll lose more than time.

If Tobi was going to turn things around, he needed clarity, focus - and above all, something real.

Someone real.

Through the chaos, Tobi found David to Goliath.

When I started this newsletter, we were searching for our people. Building a movement.

Tobi wasn’t loud. He wasn’t trying to get noticed. But from day one, he was in the trenches with us.

• Engaging with my LinkedIn posts.

• Tuning into the David to Goliath podcast every single week.

• Reading every newsletter.

• Devouring every story like it was fuel for his own battle.

Connecting with the mission as I rebuilt my life and business brick by brick.

Gravitating toward the raw, unfiltered truths we stood for:

• This path is brutal.

• You’ll bleed for your wins.

• You’ll feel alone.

Like a hand on his shoulder, a voice saying, “Keep going. You’re not crazy for wanting this.”

For Tobi, it was like someone had thrown charcoal on a dying ember.

He wasn’t alone. He wasn’t crazy. And the fight was worth it.

But what IS crazy is how everything comes full circle.

All those months searching for an avatar for David to Goliath, and there he was – listening, connecting, grinding in silence.

By January 2024, when Tobi and I properly connected, he was on the edge.

The scars of betrayal still burned. His confidence was shattered into smithereens.

Everything screamed at him to quit his fledgling agency.

Go back to university. Take the safe route. Crawl back into the cage. Bury the dream.

But deep inside, the wounded lion still roared.

He wasn’t done. He couldn’t be. He had to give every last ounce of energy to fulfil his promise to repay his mother for her sacrifices.

Then came the choice: invest $7,000 – 90% of his savings – into the David to Goliath mentorship program.

With one last roll of the dice, he wired the money and stepped into the fire.

Out of that mentoring cohort, Tobi definitely had the worst hand dealt to him. Others in the group had lucky breaks, better resources, and smoother starts.

Tobi had nothing but scars as he quietly grinded in the dark for months.

Every day, he dragged himself through the trenches with nothing to show for it. 

Then came the go-karting event. The Awakening. The birth of the killer. 

For Tobi, the bike accident had taken something vital: his connection to competition.

The spark that once blazed through sports, through every moment where he could prove himself, was gone.

Now… in Summer 2024 I organized an event for my mentoring cohort.

A casual outing, a chance to meet other young entrepreneurs in person and blow off steam by go-karting.

For a bit of context, even when he was struggling to make ends meet, Tobi would always offer a helping hand to others. He was always the nice guy. 

Yet as the engines roared to life and the race began, something changed. The sleeping giant within woke up.

He annihilated us all like an absolute savage.

Thundering around the bends like a beast unleashed.

And left us all with one simple, raw, yet powerful mantra…

At first, it was all about the track – don’t lose momentum, don’t falter under pressure.

But as we’d all come to realize, it was far more than that. “Don’t break” became the metaphor that defined Tobi’s journey.

That carried him through the hardest days of his life.

This in-person event didn’t just reignite Tobi’s competitive fire; it shattered the illusions that had weighed him down for months.

He’d spent so much time believing that everyone else was miles ahead, armed with advantages he didn’t have.

But meeting those entrepreneurs face-to-face changed everything.

He realized they were human just like him, with two arms and two legs.

Grinding, struggling, figuring it out one step at a time.

The isolation lifted. The doubts began to fade. For the first time, Tobi believed:

• I’m not that far behind.

• I can do this.

Most importantly, he saw business for what it was: another track.

A place where strategy, grit, and resilience could level the playing field.

The giant was awake, and this time, he wasn’t going back to sleep.

The Tobi who hesitated, who second guessed, who pulled back his punches… 

GONE.

No more Mr. Nice Guy.

The wounded lion was ready to roar.


Do. Or Die.

Everything Tobi had learned, every scar he had earned, slowly started rekindling his self-belief. Now it was time to fire a hail mary and reflect this in his business.

So I set him a challenge.

100 pieces of outreach every day for 100 days.

Day 10? Nothing.
Day 20? The silence was deafening.
Day 40? He hit rock bottom.

Now, seriously, his agency Everboost teetered on the brink of collapse. The voice of doubt whispered louder than ever:

• Maybe this isn’t for you.

• Maybe it’s time to quit.

But Tobi had been here before. He knew this feeling, the one that creeps in when the world pushes you to your limits.

This time, he held onto the words that had carried him through the go-karting track:

“Don’t break.”

I’ll never forget the voice note Tobi sent me on day 64. 

Before he even finished speaking, I could hear it: something had shifted.

“I can’t believe I’m telling you this,” he said, his voice trembling with disbelief and triumph. “I’m about to sign four clients.”

After months of grinding in silence, the floodgates opened. In a single week, Tobi went from near zero to securing $20K in monthly revenue.

And two months later he’s closing in on $40K months.

One of those clients is a $50 million/year company turning down far larger agencies to work with him.

When the silence drags on, don’t break.
When the doubt creeps in, don’t break.
When the world tells you to quit, don’t break.

This quiet, academic kid has become a warrior.

An emblem of everything David to Goliath stands for.

The predictable career path has evolved into a limitless horizon of possibilities.

And now he’s on the brink of changing his mother’s life forever. 

Watching this story unfold has been one of the most inspiring moments of my life.

It’s proof that success isn’t about talent or luck. It’s about self confidence.

And a reminder that the best gift you can give anyone is belief.

But the best and most important person to believe in is yourself.

Nice guy Tobi answered the call. Now it’s your turn.

If you enjoyed reading this story forward it to your friends. Remember this isn’t just another Newsletter.

David to Goliath is a movement.

A movement to empower underdogs to write their comeback stories using the power of self-belief.

The only way it grows is if we find more people like you.

So keep dreaming like a Giant.

But Fight and Believe in your dreams like a God Damn Underdog baby!!

The end.

-Nigel Thomas