Gavin Southwell rang the bell at the Nasdaq twice as a CEO, knowing his company had outperformed Apple, Amazon and Facebook. His company was Fortune Magazine's number one fastest growing public company from 2017 to 2019, and it wasn't just a tech story. It was a lifesaving operation helping millions of vulnerable Americans access healthcare for the first time.
"That we were number one, and that we had done it the right way with the lowest complaints percentage in the industry. That was cool." Southwell says regarding an achievement he’s very proud of.
He's from Northern England and moving to London was a big deal for him. Now he splits time between advising technology companies and investing in growth businesses, carrying decades of experience in investment banking and insurance technology across continents and crises. The path from there to here runs through darkness most people never see.
"I had worked in Investment Banking and Insurance Technology for almost 20 years, based in London, then when my son sadly died, and after a period of grieving and raising money for charities to help other families in the same situation, I had the chance to work in Technology for health and life insurance based in the USA," he says. "As that business grew, we helped millions of Americans protect themselves and their families, most for the first time due to the high cost of healthcare in the USA."
That business became Fortune’s number one. The one that rang the bell twice.
He now focuses on technology where there are market inefficiencies or consumer challenges that can be solved by technology and artificial intelligence. He's built businesses on three continents, survived regulatory battles, lost what matters most and kept going anyway.
Gavin Southwell has been fortunate to work for some very inspiring people throughout the early part of his career. Andrew Beazley taught him to build on strengths and not to focus so much on trying to solve weaknesses. He's also been lucky to work with positive, high-energy people who wanted to build good businesses and address market challenges through technology and improving processes.
"A defining moment was when I realized that there are more important things than money, that bad things happen, and it's how you react to that darkness that will define you," Southwell says. "After the loss of my son, and the broken life that created, I led Fortune's number one fastest growing publicly traded company, and it was a business that was doing a good thing and helping the most vulnerable in our society. I'm proud of that."
His values come through in conversation. Family first. You win, we win. Just get it done. Make it count. You never know what will happen tomorrow, so you may as well do it today.
When people ask what he does, he always replies the same way.
"I work really hard," he says.
He's only recently worked out the work-life balance. Time is precious so he believes in making the most of each day, staying in the present and choosing quality over quantity. He exercises and meditates which helps keep his head clear.
The achievements pile up like frequent flier miles. Back in London, Southwell joined a privately owned insurance broker. Within a few years as the chief operating officer, they became the largest privately owned insurance broker in the world. They won London Broker of the year. Transaction of the year when they acquired the largest wholesale broker in the United States. Claims team of the year when their office in Chile helped pay billions in claims following the Chile earthquake.
As a broker, they had the largest insurance contract in the world covering Venezuela's oil companies. They were the largest broker in most of Latin America. The business grew quickly and Southwell lived on flights around the world for a few years. It was really hard work but they built a great global business. They then sold that business to private equity.
In his early career, he was part of the team that built the world's first Quote, Buy, Print insurance business. They sold that to the world's largest insurance company. At Beazley, they were the first Lloyd's insurance company to be rated Strong for Risk Management.
Then came the United States. The Fortune number one. The company that created thousands of jobs and trained blue-collar workers to become licensed insurance agents. It was a very diverse company. About 70 percent of the staff were female. Around 75 percent were minorities.
Every year the top performers would qualify for a trip to the Bahamas. Southwell remembers one of the agents telling him how they had been able to move out of their mother's house with her two kids for the first time, and get great gifts for her children's birthday. How she had been taking swimming lessons so that she could swim with dolphins. How the trip to the Bahamas was a dream come true as she had family on the island she had never met.
All of this because she spent her days helping people a lot like her access healthcare for the first time.
Gavin Southwell has always been data driven. Facts matter and numbers tell stories. When his son died, he looked at the statistics. For parents who have to deal with the death of a child, the statistics are bleak. Most families never recover. Marriages fall apart. Men especially struggle with substance abuse and mental health challenges.
He's fortunate to have a good support network. Being able to help others less fortunate has been a blessing. The charities he supports focus on families facing similar tragedies. He also makes quiet donations that don't make headlines.
His company's success wasn't just measured in growth rates or stock performance, it was measured in lives changed. The agents who could finally afford their own homes. The families accessing healthcare for the first time. The tens of thousands of lives saved each year. He kept that folder on his desk as a reminder of why the work mattered.
The company was valued at 2.2 billion dollars when he left to focus on advising and investing in technology businesses. His experience building businesses across three continents has given him perspective on what works when connecting technology with human needs.
Southwell has been fortunate to attend an annual weekend gathering of leading business leaders and leadership of the United States several times: The ALFALFA event. He's been able to talk with a lot of very well known business leaders and politicians and see them interact with each other.
One of the nicest people, and most friendly was Warren Buffett. At the time, he was the richest man in the world, even today probably the most respected. He was very smart, fun and friendly. In that crowd, that really stood out.
"There are a lot of very successful and smart people, few are so pleasant to spend time with," Southwell says. "It was so interesting watching some of that crowd interact."
Less well known in the United States but a huge figure in the London market was Andrew Beazley. He built the second largest Lloyd's syndicate, made billions, and gave Southwell his first big role at a young age. When he died, hundreds went to pay respects. "I've never heard a bad word about him," Southwell says. "What a legacy."
Southwell has raised significant money for charities over the years. He organized and completed cycling events including cycling across the United Kingdom. He's still involved in a Tampa based charity as one of the largest supporters. His old business supported several charities and made community work part of their people's development.
When asked what advice he would give his younger self, Southwell pauses.
"I'm fortunate really, everything before brought me here, so although there have been highs and lows, that's all part of it," he says. "Just be brave and do your best, that'll be enough."
He currently serves as an advisor and investor to technology-focused growth businesses. His background includes significant experience across all aspects of capital market transactions, including successfully executing a private sale substantially above the trailing share price, negotiating large debt facilities, and managing a SPAC process.
From a poor part of Northern England to ringing the bell at the Nasdaq. Twice. The man who built America's fastest growing company while keeping a folder of lives saved on his desk. Gavin Southwell keeps working and keeps making it count.
