The Story of Our Founder: Part 1

From a broken home in Astoria to building a business empire across all 50 states : this is the remarkable journey of Randy S. Dinwiddie, the man behind Dependable Brokers and the driving force who earned the nickname "The DealMaker."

The First Memory That Changed Everything

Randy Dinwiddie's story doesn't start with silver spoons or family connections. It begins in Astoria, Oregon, with a memory that would shape everything that followed : chaos, tears, and a father carrying his youngest son away from a breaking point.

Born into a household of six children, Randy's earliest recollection isn't of birthday parties or Christmas mornings. It's of his mother crying, her spirit worn paper-thin from the relentless demands of raising six kids in a broken home. His father rushed in, scooped up young Randy, and carried him from the room as she broke down completely.

That was the last time he saw her clearly : her strength spent, her heart simply done.

"That moment became my first lesson in survival," Randy recalls. "I didn't know it yet, but life was already teaching me that when everything falls apart, you still have to find a way forward."

From that day on, Randy learned to depend on three things: faith, grit, and the quiet conviction that he could make something out of nothing. These weren't just childhood coping mechanisms : they became the foundation stones of a business philosophy that would eventually span the entire country.

Finding Strength in the Missouri Hills

After Astoria, Randy's father moved the family to central Missouri, near the Lake of the Ozarks. The rolling hills stretched deep and green, the air carried the scent of water and wood smoke, and everyone knew the value of working with their hands.

Money was tight : tighter than tight. Randy's father worked when he could find it, and the family stretched every dollar until it squeaked in protest. But the Lake became Randy's real classroom, teaching him patience, rhythm, and the kind of resilience you can't learn from textbooks.

When the family coffers ran dry, twelve-year-old Randy found work wherever he could: mowing lawns, cleaning boats, stacking wood. By his twelfth birthday, he already understood a fundamental truth that would drive his entire career : if you don't hustle, nobody else is going to hand you anything.

"Hardship was steady company, but so was hope," Randy remembers. "I learned early that poverty doesn't define you : it refines you."

These weren't just feel-good platitudes from a successful businessman looking back. They were survival lessons learned in real time by a kid who understood that his next meal might depend on his willingness to outwork everyone else.

The Decision That Defined a Life

As Randy grew older, home grew louder. Fights, frustration, and silence all shared the same cramped space. His parents were worn out from years of struggle, and the weight of it all fell increasingly on the children's shoulders.

At fifteen, Randy made a decision that would define the rest of his life : he left. This wasn't a teenage tantrum or a dramatic storm-out. He simply walked away quietly, carrying a bag of clothes, a few dollars, and an unshakeable belief that peace had to exist somewhere outside those walls.

The first nights were brutal. He slept on couches when he could find them, porches when he couldn't, and sometimes in cars. Hunger came and went like an unwelcome visitor, but loneliness took up permanent residence.

Then, one evening while walking along a road near Barnett, Missouri, a woman pulled over. She looked at Randy, saw something in his face that spoke to her, and said simply, "You look hungry. Come eat."

That meal changed everything. "I realized kindness is God's language," Randy says, "and that faith shows up in the form of strangers."

It was a lesson he'd carry forward into every business relationship, every employee interaction, and every deal he'd make over the following decades.

Faith Forged in Fire

Out on his own with no safety net, Randy faced a choice that confronts every person who's been knocked down hard enough: bitterness or belief. He chose belief.

Prayer became as essential as food. Sometimes he prayed for his next meal, sometimes for direction, and sometimes just for the strength to make it through another day without giving up entirely.

Randy remembers praying for a man he met who'd lost everything. Weeks later, that same man tracked him down to share that things had turned around. "Kid, you've got something in you," the man told him.

Randy didn't fully understand it then, but that "something" was his calling : the same faith that would carry him through every failure and every success that lay ahead.

Those hard nights on the road built more than character : they built an unbreakable backbone. Randy's confidence didn't come from comfort or privilege. It came from the fire of necessity.

The Education of a Entrepreneur

Randy worked anywhere that would hire him: sweeping floors, hauling boxes, fixing whatever was broken. Every job taught him something new about the value of honest sweat and the satisfaction of earning your way forward.

By his early twenties, Randy found himself deep in the collections and repossessions business, learning firsthand how systems collapsed and how people responded to extreme stress. It was here that he began developing a philosophy he'd later call "Trimming the Pyramid."

The concept was elegantly simple: remove waste, empower people at the bottom, and hold leadership accountable at the top. It wasn't just a business model : it was survival thinking applied to organizations.

"You can't lead from a swivel chair," Randy learned. "You lead by doing."

This hands-on approach would become the signature of every company he'd eventually build, from his early collection agencies to the nationwide network of Dependable Brokers operating today.

The Phoenix Office

At twenty-five, Randy inherited a failing office that everyone else had written off. No morale, no structure, no hope. The previous management had given up, the staff was demoralized, and profits were a distant memory.

But Randy had been written off before, too, and he knew something about rising from ashes.

He rebuilt that office piece by piece, arriving early and staying late while refusing to accept excuses from himself or anyone else. Within months, they were profitable. People smiled again. The same staff that had been updating their resumes started believing in themselves and their work again.

That turnaround taught Randy one of life's purest truths: "You can't teach hunger : you either have it or you don't."

Building an Empire, One Deal at a Time

In 1992, Randy founded Raven Financial Group, his first real company, handling collections and auto repossessions across Missouri. The business made money, but over time Randy realized he wanted to build rather than just collect.

So in 2004, he launched Atlas Bail Bonds, helping families get their loved ones home during their darkest hours. In 2005, he added Deal Maker Publishing, providing local businesses with affordable advertising solutions that actually worked.

Each new venture pushed Randy closer to his true purpose: turning problems into opportunities, not just for himself, but for everyone he could reach.

By 2010, Randy founded Amerishop Mobile, combining marketing and technology to give small businesses the tools they needed to compete. In 2013, he launched Dependable Brokers Insurance Agency, offering life and annuity products with the same personal touch that had made all his previous ventures successful.

Eventually, these companies united under the Amerishop Services LLC umbrella, operating in all 50 states and serving thousands of clients nationwide.

How "The DealMaker" Was Born

The nickname didn't come from a marketing meeting or a branding consultant. It came from Randy's clients themselves.

Randy would sit down with shop owners, towing operators, and small-town entrepreneurs, working through numbers and possibilities until they found something fair for everyone involved. When the deal finally closed and both parties walked away satisfied, they'd smile and say, "You're the DealMaker."

Soon, phone calls started coming in with people asking, "Is the DealMaker in?"

That's when Randy realized it wasn't just a nickname : it was a promise. If he was in the room, the deal was getting done, and both sides would walk away stronger than when they started.

"The DealMaker was born not from ego," Randy explains, "but from earned respect."

This wasn't just about closing transactions. It was about creating relationships and opportunities that would last for years. It was about being dependable when dependability mattered most.

The Power That Drives Everything

Success came, but it was never easy. There were sleepless nights, cash-flow squeezes, and setbacks that would have broken lesser resolve. But persistence became Randy's secret weapon.

Every obstacle became a blueprint for a better system. Every failure taught him something that the next victory would require. When competitors gave up, Randy re-strategized. When markets shifted, he adapted faster than anyone expected.

"That's the DealMaker way," Randy says. "Don't quit : re-strategize."

This philosophy would prove essential as Randy's companies expanded nationwide, eventually serving clients from coast to coast while maintaining the personal touch that made them successful in the first place.

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This is Part 1 of Randy Dinwiddie's remarkable journey from a homeless teenager in Missouri to the founder of a nationwide business empire. In Part 2, we'll explore how Randy built his modern companies, earned national recognition, and developed the systems that make Dependable Brokers the trusted name it is today.

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Written by Sarah Mitchell for Amerishop Services