White Collar Advice | Sunday Newsletter | April 6, 2025
Welcome to this Sunday’s newsletter I call, The Underdog’s Edge.
Earlier this week while reading The Land of Stories: The Wishing Spell with my daughter, I came across a line that stopped me cold. It wasn’t a quote from the Harvard Business Review or a line from a personal development podcast. It came from a conversation between Snow White and her imprisoned stepmother—the infamous Evil Queen.
On page five, Snow White says: “Outside these prison walls, the world refers to you as the Evil Queen.”
Her stepmother responds: “If that is what the world has labeled me, then that is the name I shall learn to live with. Once the world has made a decision, there is little anyone can do to change its mind.”
That line made me think. “Once the world has made a decision, there is little anyone can do to change its mind.”
It reminded me of how the world sees someone who has been convicted of a crime. Once the Department of Justice issues a press release, once the headline reads “Former Executive Sentenced to Prison”, the story is written. The world reads that version. They consume the government’s narrative. And for many, it’s final.
There’s no follow-up story about your remorse, the work you did in prison, the people you helped, the family you healed, or the business you built when you got home. The world moves on. You, however, do not.
And yet, in that same line from the Evil Queen—intended to feel hopeless—I found a seed of empowerment. Because while it’s true the world makes biased decisions quickly (to learn more watch our webinar on “Thin Slicing”), what it rarely anticipates is the strength of the underdog. Especially one who doesn’t waste time trying to convince the entire world. The strategic underdog doesn’t tell. They show.
That’s the topic of this week’s newsletter.
The Underdog’s Edge: When You Live With a Label
Once someone pleads guilty, or a verdict is entered, or the sentencing order is signed, a person is labeled: felon, fraudster, convict, or criminal. It’s an identity the world applies broadly, and often permanently. And trying to change that perception head-on—trying to go toe-to-toe with it—is usually futile.
Malcolm Gladwell writes about this in David and Goliath. He explains that underdogs rarely succeed by fighting the battle on their opponent’s terms. David didn’t pick up a sword and try to match Goliath’s strength. He used a sling—an unexpected weapon that leveraged his speed, his accuracy, and his creativity.
That’s the path forward for someone with a felony conviction. You don’t win by pretending you’re not the person the government described. You win by showing the world something different—a new narrative, authored through action.
And that means refusing to adopt a victim’s mindset, even when it’s tempting. Even when the label is unfair. Even when you are misunderstood or misrepresented.
On page nine of the same book, the Evil Queen adds another line that’s just as revealing:
“I will continue to be degraded into nothing but a grotesque villain until the end of time. But what the world fails to realize is that a villain is just a victim whose story hasn’t been told.”
There’s some truth in that. But there’s also danger.
If you adopt this mindset—if you begin to see yourself as a victim of the government, or of unfair media coverage, or even of your co-defendants—then you run the risk of living inside that identity. And no matter how long your prison sentence is, if you fully embrace the role of the misunderstood villain, then you’ll still be serving a sentence long after you leave federal custody.
I’ve seen it too many times. Someone does 24 months in a federal prison camp, but they carry that bitterness and self-pity for 10 years. That’s not freedom. That’s just a different kind of prison.
The Underdog Advantage
Let’s take this idea further. In The 48 Laws of Power, Robert Greene outlines Law 36: Disdain things you cannot have—ignoring them is the best revenge.
For someone living with the reality of a criminal conviction, the temptation is often to correct the record, to plead your case again to the public or to anyone who will listen. But that’s not power. That’s distraction. True power comes from building something undeniable, not from spending time explaining why the DOJ got it wrong.
When I went to prison, I felt the world had made its decision about me. I had lost everything—career, credibility, certainty. But I came to understand what 50 Cent meant in The 50th Law when he wrote about embracing fear as fuel. He said: “People who fear losing something are weak. When you’ve already lost everything, you become dangerous.”
There’s power in that reality. Bob Dylan captured it simply when he sang, “When you ain’t got nothing, you got nothing to lose. You’re invisible now, you’ve got no secrets to conceal.”
There’s power in having nothing left to lose—and recalibrating your life around that moment. When you no longer fear loss, you’re free to fight. And even if you fail, you walk away with two invaluable assets: the dignity of trying and the wisdom earned from effort.
That’s what most people never experience. They stay frozen. You don’t have to.
You Only Need a Handful
One of the great myths of success is that you need to win over the masses. In reality, you don’t need “the world” to believe in you. You need a few right people to believe. The right partner. A few clients. One or two advocates in your industry. A mentor. Maybe a judge, probation officer, or licensing board.
My first handful were: my family, Sam Pompeo, Brad Fullmer, and Michael Santos.
You build back not by talking about what you’re going to do, but by doing it. Not by asking for second chances, but by creating something valuable—even if it’s small, even if it’s just the first brick in a long wall (I just watched Wicked for the 4th time with my daughter, so the “brick” analogy made sense!).
In the digital age, content is leverage. Writing, teaching, mentoring, building a track record of discipline and value—these are not just tactics. They are tools of reinvention. They show the world that the person in the press release is not the person you’ve become.
The Real Narrative Shift
When I speak with people in our community many of them are obsessed with “changing the narrative.” They want people to see them differently. And I understand that. But the hard truth is: you don’t change the narrative by debating it—you change it by building a new one alongside it.
It’s the same reason athletes come back from scandal when they win again. Not because they ran an apology tour. Because they got back to doing the work—and winning. That’s what people believe. They believe what they see.
The “felon” label doesn’t have to go away. You just make it irrelevant.
The Final Lesson from the Evil Queen
At the end of the day, the Evil Queen had it right in one sense: The world does make decisions. But where she saw the world’s decision as the end of her story, you don’t have to.
Yes, the DOJ may have issued a press release. Yes, your name might show up in Google with an ugly headline. Yes, some people will never forgive or forget.
But you’re not here to change their minds. You’re here to create outcomes that speak for themselves.
And to anyone facing a felony conviction, I say this: don’t waste your time trying to convince the world you’re not who they say you are. Show them something better. Show them what you’ve built. Show them the strategy of the underdog.
Because when you do that, you don’t need to change every mind.
You just need to change a few—and that’s enough.
See you tomorrow for our weekly webinar.
Justin
