Gavin Southwell grew up in a poor part of Northern England where moving to London felt like a distant dream. Today, he’s the former CEO who twice rang the bell at the Nasdaq as president of Fortune Magazine’s No. 1 fastest-growing public company from 2017 to 2019. That company outperformed Apple, Amazon and Facebook.

The path wasn’t smooth. Personal devastation forced him to reconsider what success actually meant. “After the loss of my son, and the broken life that was created, I led Fortune’s No. 1 fastest-growing publicly traded company, and it was a business that was doing a good thing and helping the most vulnerable in our society,” Southwell says. “I’m proud of that.”

Southwell has more than 17 years of technology experience and has worked with some of the largest insurtech exits in history. He currently advises and invests in technology-focused growth businesses.

What stands out isn’t just the resume. It’s what he chose to do when everything fell apart. When his son died, statistics painted a grim future; most families don’t recover. Southwell looked at the data, acknowledged the darkness, and decided facts still mattered. “I knew that data didn’t lie, I knew that facts mattered,” he says.

That belief in truth would define not just his recovery but his entire approach to leadership.

Building Global Businesses Before Loss Changed the Game

Southwell’s early career reads like a masterclass in scaling operations across continents. After working in investment banking and insurance technology for nearly 20 years in London, he joined a privately owned insurance broker. Within a few years as chief operating officer, the firm became the largest privately owned insurance broker in the world.

The wins stacked up. London Broker of the Year. Transaction of the Year when they acquired the largest wholesale broker in the U.S. Claims Team of the Year after their Chile office helped pay billions following an earthquake. “As a broker, we had the largest insurance contract in the world (Venezuela’s oil companies), and we were the largest broker in most of Latin America,” Southwell says. “The business grew quickly and I lived on flights around the world for a few years.”

That business was sold to private equity. Earlier, he helped create the world’s first quote-buy-print insurance business, which was sold to the world’s largest insurance company. At Beazley, he was risk manager when the company became the first Lloyd’s insurance firm rated strong for risk management.

The pattern was clear: Identify inefficiencies. Build solutions. Scale. Exit. Then came the defining moment. “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 which will define you,” he says.

Grief, Data and a Return to Purpose

After his son’s death, Gavin Southwell took time to grieve. He raised money for charities helping other families facing similar tragedies. Instead of staying in London, he took an opportunity to work in technology for health and life insurance based in the U.S.

The business grew fast. As it scaled, it helped millions of Americans protect themselves and their families, many for the first time, because of the prohibitive cost of healthcare. Gavin Southwell was leading a company that was successful by Wall Street metrics but also doing something meaningful.

He kept a folder on his desk filled with emails and letters from people whose lives were saved by the healthcare coverage his company connected them to. Tens of thousands of lives each year. “It still amazes me how many lives we were able to help save,” he says.

At the company’s annual top-performer trip to the Bahamas, an agent told him how she’d been able to move out of her mother’s house with her two kids for the first time. How she got great gifts for her children’s birthday. How she took swimming lessons so she could swim with dolphins and how the trip was a dream come true because she had family on the island she’d never met.

All of this happened because she spent her days helping people just like her access healthcare. Hearing an agent describe everything she’d achieved while helping others made him proud.

The company created thousands of jobs. It trained blue-collar workers to become licensed insurance agents. About 70% of the staff were female. Around 75% were minorities. “We were probably one of the most diverse and female-heavy tech businesses to ever exist,” Southwell says.

Ringing the Bell at the Nasdaq and Weathering the Storm

Ringing the bell at the Nasdaq once is a milestone. Doing it twice as CEO knowing your company outperformed Apple, Amazon, Facebook and everybody else is rare. “That we were No. 1, and that we had done it the right way. With the lowest complaints percentage in the industry,” Southwell says. “That was cool,” The company became the go-to source for data. They were quoted by Fox, CNN and the White House.

Ask Southwell about his personal and professional values and the answer is direct. “Family first, you win we win, just get it done, and make it count.m,” he says. “You never know what will happen tomorrow so you may as well do it today.”

When people ask what he does, his reply is simple. “I work really hard,” he says.

He’s learned the importance of work-life balance only recently. If you enjoy what you’re doing, spending a lot of time on it feels natural. But he’s realized how precious time is. “You should make the most of each day, stay in the present,” he says.  “You can always work more, but quality is better than quantity.”

To manage stress, he exercises and meditates. Simple practices with discipline.

Gavin Southwell and a Leadership Philosophy Forged in Fire

Gavin Southwell’s leadership philosophy was shaped early in his career. Andrew Beazley, founder of the second-largest Lloyd’s syndicate, taught him to build on strengths. Beazley made billions, gave Southwell his first major role at a young age and spent time offering advice. When he died, hundreds attended. “I’ve never heard a bad word about him,” Southwell says. “What a legacy.”

At the Alfalfa Club’s annual gathering, he met Warren Buffett, at the time the richest man in the world. Buffett was remarkably pleasant. “He was very smart, fun and friendly. In that crowd that really stood out to me.”

Success, for Southwell, isn’t about fame. “I don’t care what people I don’t know think about me,” he says. “I care about family and friends, and I want them to know that I’m doing well and living a good life, that just means trying to be happy and content.”

There’s always more to do, things that could have been changed or done differently. Dwelling on that is pointless. “Make it count right now, do your best, and that to me is success.”

If he could give advice to his younger self, it would be brief. “Just be brave and do your best, that’ll be enough.”

Gavin Southwell Solves Market Inefficiencies with Technology and AI

Gavin Southwell now focuses on technology where market inefficiencies can be solved by technology and AI. He has significant experience in capital market transactions including a successful take-private sale, negotiating large debt facilities and running a SPAC process.

His philanthropic work continues. He remains one of the largest supporters of a Tampa-based charity. His former company made community work part of people development. He organized cycling events across the U.K. to support causes that mattered.

“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. “And 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.”

Loss reshaped his worldview. It didn’t break him. It only clarified what mattered.

Southwell has stood in global boardrooms and weathered political storms that would have crushed most leaders. Through it all, he’s maintained a relentless belief in truth and building businesses that solve real problems.

The future is about leveraging technology and AI to address market inefficiencies. It’s about helping businesses scale with integrity. It’s about making sure that when the work is done, lives are better because of it.

What he cares about is simple: family, friends, doing work that matters and making each day count.