The Underdog Still wins

August 4, 2025

Hello there,

It’s your financial literacy guide, CoachMO.

This week, we are diving into an interesting tale: The Underdog Still Wins.

Ever felt like you drew the short straw? A job that slipped away, a bad investment, or someone else grabbing your moment in the sun? We’ve all been there.

Today, we are diving into the epic tale of Esau, the ultimate underdog who turned betrayal into a masterclass in resilience and wealth-building. This isn’t just an ancient story; it’s a roadmap for anyone to flip setbacks into success.

Imagine twin brothers born into a high-stakes family drama. Esau, the rugged hunter, bursts onto the scene first with red, hairy, and Dad’s favourite. Jacob, the quiet schemer, follows, clutching Esau’s heel like he’s already plotting. Their mom, Rebekah, favours Jacob, and a prophecy sets the stage: “The older will serve the younger.” Destiny seems to have a favourite, and it’s not Esau.

Fast-forward to a pivotal moment.

Esau stumbles home, famished from a hunt, and finds Jacob stirring a pot of lentil stew. In a moment of pure impulse, think blowing your paycheck on a whim, Esau swaps his birthright (the family legacy, inheritance, the whole deal) for a quick meal. Instant gratification? Sure. Buyer’s remorse? Big time. The birthright wasn’t just cash; it was his stake in the Abrahamic covenant, his future.

But the real blow comes later.

Dad, Isaac, old and blind, is ready to pass on the big blessing, both spiritual and material gold. Rebekah and Jacob pull off a con for the ages: Jacob dresses up as Esau, tricks Isaac, and snags the blessing. Esau returns, realises he’s been duped, and lets out a heart-wrenching cry: “Have you only one blessing, Father?” He’s left with a lesser promise, a life by the sword, far from Jacob’s fertile lands. Betrayed twice, he’s the ultimate underdog.

If the story ended here, Esau would be a cautionary tale of loss. But here’s the twist that hooked me. Esau doesn’t collapse. He picks up, moves out, and builds an empire. We are talking wealth, livestock, servants, land and the Edomites, a powerhouse nation. Archaeological evidence, like The New Encyclopedia of Archaeological Excavations in the Holy Land, shows Edom as a complex society controlling trade routes, not some sad footnote. Years later, when Jacob comes grovelling with gifts to make amends, Esau, already loaded, says, “I have enough, my brother; keep it.” Contentment from the “loser”? That’s a plot twist. Jacob inherits the spiritual legacy (Israel’s line), but Esau crushes it materially. Success, it turns out, has many faces.

So, what does this mean for us?

Esau’s story is a goldmine for anyone chasing financial freedom, especially if finance isn’t your thing. Let’s break it down. First, impulse decisions kill dreams. Trading his birthright for stew? That’s like draining your savings for a flashy gadget.

Lesson:

Pause and ask, “What’s the long-term cost?” A 24-hour rule for big purchases can save you from regret.

Second, setbacks don’t define you.

Esau could have stayed bitter, plotting revenge. Instead, he built wealth. Resilience and grit trump resentment, turn “why me?” into “what now?” Third, his reconciliation with Jacob is huge. Holding grudges drains you; forgiveness frees you to focus on your goals. Esau’s story screams: You can thrive against the odds.

Now, let’s talk money.

Esau nailed diversification without a finance degree. He didn’t bet everything on the family inheritance; he built multiple streams of land, people, and influence. Today, that’s mixing stocks, real estate, or a side hustle. Aim for at least two income sources by 2026. His “I have enough” moment?” That’s the antidote to lifestyle creep. Track your net worth monthly, celebrate small wins, and know when you’re good. Contentment compounds faster than any interest rate.

Behaviorally, Esau flips the victim mindset. His “sword” life, which is tough and scrappy but became his strength. Success paths are rarely straight; embrace the twists.

Life lesson: Blessings come in many forms, material, spiritual, or a mix. Esau challenges us to define our own “win.” Is it wealth? Impact? Peace? You decide.

Let’s ground this with modern underdogs echoing Esau.

Take Dean Graziosi, 2025’s real estate mogul. Raised by a single mom, dyslexic, moving 20 times by 19, no birthright here. Like Esau’s stew blunder, he could’ve settled for struggle. Instead, he sold firewood as a teen, bought a fixer-upper at 20 with no money down, and built a $1 billion empire across 13 companies. His secret? Resourcefulness, self-education, and fierce confidence. In 2024, he’s still thriving, proving underdogs turn “no” into “now.”

Then there’s Dana White, UFC president, with a $520 million net worth in 2025. From a single-parent home, he saw UFC crumbling in 2000, Esau-level betrayal vibes. He convinced friends to buy it for $2 million, absorbed $40 million in losses, and turned it into a $12 billion juggernaut. Diversified? Absolutely! Real estate, endorsements, even a whiskey brand. Like Esau’s “enough,” Dana says money buys freedom, not happiness.

Esau’s journey, from betrayal to triumph, shows that underdogs win by rewriting the rules of victory. Material or spiritual, it’s about crafting your path.

CoachMO’s Takeaways:

Financial Lessons: Skip impulse buys, build an emergency fund first. Diversify income (stocks, gigs, skills) for stability. Practice “enough” with a budget to avoid overspending.

Behavioural Principles: Choose resilience over regret. Forgive to move forward. Flip setbacks into strengths, like Dean’s hustle.

Life Wisdom: Success isn’t one-size-fits-all. Define your win, wealth, purpose, or both. What’s your underdog move? Hit comment below and let’s talk!

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