Standing up from an Underdog Position Using Stories and Community with Jamie Russo

Jamie Russo is the author of The Underdog Paradox. We discussed the writing process, publishing his first book and the power of Twitter friends.

Jamie russo first time author

It’s November 2019 and the headlines aren’t yet filled with COVID-19 news. Instead, business papers around the country report on WeWork. Due to a huge IPO crisis, the company announces they will have to lay off a large part of their employees. One of them is Jamie Russo.

During his time at WeWork, Jamie had met all sorts of interesting founders and creators. Many of them were underdogs; people who had nothing and still made it happen. He now had three months before he would have “nothing”. Three months to figure out what to do next. 

So Jamie made a decision. A big decision. He would write a book about the social entrepreneurs he had met. He would share their stories to inspire you. If they could do it, you can do it too.

It’s now exactly four months since The Underdog Paradox’ launch on 9 December 2020 and I’ve scheduled a video call with Jamie. COVID-19 is very much in the news now but that’s not the only reason we scheduled a video call. We also live 6.000 km apart — give or take a few.

Funnily, this interview wouldn’t have happened without COVID-19. I’m sure our lives would be very different and I’m even more certain we wouldn’t have met on Twitter.

The Underdog Paradox book cover

But we did. And Jamie accepted to be part of this project. Within minutes of contacting him, Jamie had scheduled a call for 4 pm the following day. My first interview was scheduled.

Was I nervous? No. But Murphy and his law were present as ever. My laptop didn’t start, my baby woke up and needed care, and I couldn’t find earphones to call in with my phone. This all happened at 4 pm sharp, of course.

I was obviously a few minutes late, but Jamie didn’t mind. I was a terrible interviewer as well, but Jamie didn’t mind. Jamie is without a doubt the nicest person I could’ve started with. 

Underdogs have Resilience, Grit, Authenticity and Hope

In The Underdog Paradox, Jamie shares the stories of five incredible underdogs. Five people who had the world against them overcame their struggles and found solutions.

Those people are:

Lual, who founded Junub Games, a video game company promoting peace and social impact. He spent his entire childhood in a refugee camp after his family had fled the civil war in South Sudan. Even though he didn’t have internet access at home, he learned to code and design video games.

A river cuts through rock not because of its power but because of its persistence.

The Underdog Paradox

Marcus, who was sixteen when he was sent to prison for eight years. Back on the street, he started working in a paint store and soon launched his own painting business for people with similar backgrounds. Shortly after he founded Flikshop, an app that allows friends and family to print and send personalised postcards to prison.

Clarence, who grew up in a family with fighting parents. They took little care of him so he sold drugs to survive. In his adult life, he managed several companies and turned into a successful businessman, founding his own company Upsie.

visual about the underdog paradox by @Sathyanand1985
“When underdogs reject the status quo, they inspire the rest of us to dream big.”
By @Aurasky_ (More of these in The Yellow Visual)

Manu, who was raised in a poor French family. He was working on campus and everyone in his family was contributing to his studies in the US. His situation was difficult and many are experiencing the same struggles. That’s why he founded MPOWER Financing, an organisation that helps with student loans for international students.
Shavini, who had breathing issues from a very young age. Doctors in Sri Lanka told her she had a strange incurable disease. She wouldn’t live. But she didn’t give up. At John Hopkins University, they found the cause of her problem. There wasn’t anything to be done about it but she could potentially monitor the situation. That’s why she developed OxiWear, a small ear device that constantly monitors oxygen levels and gets help on time.

If these people could do this, then no one should have any excuse. 

Some say they had an advantage, being an underdog, but would you want to go through their struggles to get that “underdog effect”? Probably not. 

Pieces of the puzzle

Jamie says the entire writing process took him about one year. While he was off work, he decided to write 500 words for 90 days without failure. 

For the juicy details about how to write a book with fancy tools and techniques, Jamie is not your guy. His stack is super simple: he used Grammarly to fine-tune his writing and to turn speech into text. He would just write whenever he felt like it. Sometimes early in the morning, sometimes just before midnight. The only thing that mattered was to write daily. 

It just shows that you don’t need all the shiny stuff and carefully carved out time blocks to make it happen. 

Writing daily gave him a rough total of about 40.000 to 45.000 words.

He never thought about it as writing chapters of his book, though. Instead, he wrote one article per day. 

“All a book is, is just a collection of stories.” 

Jamie Russo

Jamie assumed that if he could connect one article to another with just a few lines, he would have enough content to create his book. For each chapter, he decided he should include at least one interview, one personal story and one research study. 

With a completed first draft, three months of editing followed. Jamie found the Twitter community to be extremely helpful here. He also had 50 beta readers and a few editors from his publisher who helped him out.

During this process, he says he rewrote the book about three times. He may have ended up with a total of 120.000 words, which were reduced to the original number of 40.000 again. 

Much of the rest of the process was handled by his indie publisher: New Degree Press. They took care of projects like the book design, marketing assistance and layout formatting. 

The secret of close friends

Of course, writing your first book is a big venture. Being a first-time author, Jamie was a bit of an underdog himself. Who would help him? Who would keep him accountable?

Fortunately, he met an old university professor who introduced him to his publisher. After paying one upfront fee, they would take care of the rest, including a community of fellow writers.

So that was part one. Building in public is another accountability tool Jamie applied. If he were to maintain his credibility, he would have to write every day for ninety days. And so he did. 

Jamie Russo campfire

His Twitter friends, finally, are his true secret. Moving together and jumping on a weekly call each Friday has pushed him week after week. Knowing someone has your back is a great feeling. It’s powerful.


On the Marketing side, he tried two platforms. Initially, he grew a newsletter via LinkedIn. Thanks to his daily writing habit, he soon had 10.000 subscribers but he didn’t feel like they were the right audience.

So halfway through writing his book, he changed course. Even though he had few followers on Twitter back then, he found the audience to be a lot better. These people were engaged. These people were helping and giving feedback. These people would be interested in buying his book. 

And so, in July 2020, he launched the pre-sale of his book. Selling over 200 copies, he made enough money to cover the upfront fees of his publisher. 

Behind the horizon

People who follow Jamie on Twitter know that he’s always moving. He’s always exploring new and different horizons. Jamie is known for his 280-character stories, for turning 1000+ profile photos into avatars. Overnight. And for supporting his fellow creators.

If one of those horizons has another book in store for him, this is what he’d do differently.

First, he says he would “screw imposter syndrome”. People are more positive than you’d expect so there’s no need to feel that pressure. 

This reminds me of Coelho: “You cannot sell your next book by underrating your book that was just published. Be proud of what you have.”

I think Jamie’s in a perfect place here to move on from The Underdog Paradox and create something even bigger.

Secondly, he would embrace the learning process. The interesting part of a book is doing the research and trying to find the story.

His advice for other writers and his future self: “Don’t feel like you need to know exactly what your story is about at the beginning. Let the story emerge. Your job as the writer is to connect the dots and turn what might appear as disparate ideas, disparate themes and disparate subjects into a book.”

Jamie’s story summed up with a quote from the book:

Underdogs don’t think “I can’t.” They think: “I’m going to prove I can.”

And he did. You can buy the proof here. 

Book Title: The Underdog Paradox
Author: Jamie Russo
Twitter: @jamierusso


1 thought on “Standing up from an Underdog Position Using Stories and Community with Jamie Russo”

  1. Thanks for this interview Kjell! Really enjoyed reading the article and the insights from other’s stories as underdogs.

    My big takeaway: persistence is key to moving from being an underdog to achieving big dreams.

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