We’re excited to introduce you to the always interesting and insightful David Tossie . We hope you’ll enjoy our conversation with David below.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

My name is David Tossie, and I am the founder of Tossie Advisory Group (TAG). My journey into financial literacy wasn’t born in a classroom or on Wall Street—it was forged through lived experience, decades of earning and spending without guidance, and the awakening that came when I realized how much wealth-building knowledge was withheld from working-class families like mine.

I grew up in a household where money was simply about survival, not strategy. After serving in the military for twenty years, I saw firsthand how many hardworking men and women lived locked in a “work, get paid, spend, repeat” cycle that robbed them of the chance to create a legacy. Those observations, combined with personal lessons from my own financial missteps, shaped my mission: to teach everyday people the financial literacy skills that can change the trajectory of their families for generations.

Through TAG, I provide a mix of books, journals, courses, and community programs that are designed to be approachable and practical. I don’t sell “get rich quick” promises or stock tips. Instead, I equip people with tools: how to understand basic investing, how to build habits around saving, how to start with as little as $5, and how to think about money as a tool for freedom instead of a source of stress. My clients are often hourly workers, single-income families, or veterans—the very people I grew up with and served alongside.

My hobby is ownership now. How many families can I help become true owners instead of just insurance recipients? How many communities can I impact for the better? I come from humble beginnings, and my own transition took decades of mistakes and failures before I found the clarity to change. If I can do it, then I can help others do the same. My brand is not about ego or debt-driven status symbols—it’s about education, empowerment, and reshaping the legacy conversation.

For people from my socioeconomic background, life often felt like a chessboard where every move was already predetermined: work hard, pay bills, repeat. But adversity gave me vision. I had to stop obsessing over my bank account and start embracing a new destiny—one centered on serving others. I want my brand remembered the way my mother is remembered: as someone who cared deeply about her family and her community, even into her mid-90s.

I believe things don’t happen to you, they happen for you. Yes, I wasted thousands of dollars in my younger years, but I’m alive today and determined to be better—and to help others be better. At TAG, we believe financial literacy is more than numbers; it’s emotional intelligence, discipline, and the courage to build wealth instead of chasing appearances. The “other side of the tracks” isn’t successful because of flashy cars or 5,000-square-foot houses. They succeed because they focus on wealth, not image.

If you interact with Tossie Advisory Group, you will be changed. Our mission is to destroy debt-driven thinking, challenge egos, and open a dialogue about true legacy. This work is humbling, spiritual, and it cannot be silenced. Too often, men and women in my community shut down at the first sign of adversity—whether in money, relationships, or life itself. But in survival mode, no light of legacy can shine through. My purpose is to help people break that cycle.

This financial literacy mission is the most important work of my life. It is the place where adversity and service meet. I cannot change the past, but I can use the lessons I’ve lived to help others claim a brighter future. That is what TAG stands for: not just advising, but equipping people to build, grow, and leave something lasting.

Can you tell us about a time you’ve had to pivot?

I’ve only really had two jobs since I was 17. At seventeen and a half, I left home, joined the military, and never had the chance to return and reset. For 26 years, 7 months, and 22 days, I honored my commitment to both my country and my family. My mission was simple: provide the capital, stability, and love my family needed to become a stronger, better generation than me.

After retiring from the military, I transitioned into federal civil service, where I worked another 12 years. But when a new administration swept into office, everything changed. Suddenly, I was no longer seen as a faithful servant to my community and my nation. Instead, I became disposable. Layoffs and dismissals came one after another, and I was forced into an unthinkable decision: early retirement. The result was humbling—a monthly stipend that worked out to about $1.65 an hour for a lifetime of service.

I couldn’t dwell on the unfairness of it. I had to pivot. I began to pray for direction. Watching loyal federal employees—some with 20, 30, even 40 years of service—locked out of their offices and unsure where their next meal would come from shook me. I thought about the lowest-paid workers, those most vulnerable to being cast aside, and I picked up a pen and pad. I asked myself: How can I help them not just survive transitions, but never again be unprepared for life’s adversity?

That question birthed my first book, Stock Investing for Poor People, which was followed by an interactive website providing automated tools to help hourly workers, single-income households, and veterans build wealth. Soon after, I published Stock Investing for Broke People. What started as a personal pivot grew into a platform and a voice—a way to transform adversity into opportunity and help others find strength where I once felt none.

We’d love to hear the story of how you turned a side-hustle into a something much bigger.

I grew up in central New Jersey, right between New York and Philadelphia. In Trenton, nearly every family had a hustle. Somebody cut hair in the basement, somebody sold clothes out of the trunk of their car, others worked extra shifts at the steel mill. Even my mother’s schoolteacher friends often had second jobs just to make ends meet. That environment taught me early that having a side hustle wasn’t optional—it was survival.

From a young age, I picked up that lesson. I shoveled snow before school during blizzards. I delivered items door-to-door. I tutored kids in basic math and English. Over the years, I always found a way to generate extra income, and every hustle gave me a new skill set. I learned how to connect with people, how to sell in a way they understood, and how to create value where others only saw obstacles.

The military added discipline and structure to that natural hustle spirit. By the time I retired, I realized all those experiences had been preparing me for something bigger. Instead of hustling for the next bill or the next car payment, I wanted to hustle for a legacy. That’s what pushed me to turn my financial literacy mission into my full-time focus.

Key milestones for me have been publishing my first book, Stock Investing for Poor People, launching an interactive website to help hourly workers and veterans with automated investing tools, and then expanding with Stock Investing for Broke People. Each step wasn’t just about scaling my hustle—it was about scaling my impact. What started as finding ways to survive has transformed into a mission to help others build, grow, and pass on wealth for generations.

Contact Info:

• Website: https://tossieadvisorygroup.com/
• Instagram: https://www.instagram.com/tossieadvisorygroup/

Image Credits
David Tossie is the owner of these photos