Tom Gatos didn’t always plan to become a founder. But looking back, the signs were there early—and often. Growing up in Frankford, Philadelphia, Tom figured out quickly that if you could create something useful (or even just cool), you could probably sell it.

“I realized early on that making your own money meant having independence,” he says. “And when you gave someone something they needed, and they smiled? That was everything.”

That instinct never really left. It just evolved.

Today, Tom is the founder of On-Call CMO, a fractional marketing agency for early-stage startups that can’t yet afford a full-time executive, but still need high-level guidance.

When Amanda Stein graduated college, she joined her dad’s company.

A small, family-run commercial furniture business. She started with case studies. Stayed seventeen years.

She thought she’d take over the whole thing someday.

Then the world flipped.

The pandemic hit. Her priorities shifted. She didn’t want the company. She wanted something of her own.

Now she runs Joya Creative—a content studio helping founders sharpen their message, find their voice, and finally say what they’ve been trying to say.

When Payal Raj moved from Toronto to Chicago, she thought it’d be easy. Same language. Same continent. Same culture — more or less.

It wasn’t.

Credit history didn’t transfer. Medical records didn’t matter. Even the unspoken rules of day-to-day life felt unfamiliar. And it wasn’t the first time she’d experienced it.

Payal has lived in six countries. Every move came with a new wave of stress, confusion, and loneliness. Now she’s building something to change that.

Settle Smart is her AI-powered platform to help immigrants settle faster — by giving them local context, cultural norms, and practical answers right when they need them.

When Henry Dabrowski was five years old, he started selling cups of water to runners and cyclists passing by his house in Milwaukee.

No plan. No pricing strategy. Just cups from the kitchen sink, a front yard, and the confidence to give it a shot.

“I kind of remember it being cups,” he says. “We didn’t have water bottles. But we had a sink and some clean cups.”

That’s still how he builds. See a need. Get moving. Make it work.

Today, Henry runs DarkFusion Systems, a boutique technology company that builds custom PCs, supports small businesses with white-glove IT services, and manufactures its own mechanical keyboards — all from a tight, four-person team.

Allison Ditmer didn’t leave her corporate job with a perfect plan.

She left because she couldn’t ignore the feeling any longer — that tug that maybe life wasn’t supposed to feel this misaligned. The back-to-back meetings, the frantic daycare pickups, the “mad dash” between dinner, dishes, and trying to soak up even five minutes with her kids before bed. It wasn’t sustainable. And it wasn’t the life she wanted.

“I don’t know exactly what this next chapter will be,” she told herself in 2021. “But I know it has to be different.”

Angela Ryan didn’t plan to start her own business. She just couldn’t ignore the signs anymore.

After a decade of working in creative and marketing roles across startups and scrappy teams, she kept seeing the same patterns: over-posting, under-strategizing, and brands desperately trying to make noise without actually saying anything.

So when she got laid off a month and a half before her wedding — blindsided, stressed, and unsure what would come next — she did what came naturally.

She got to work.

Dora Gutierrez didn’t grow up planning to be a founder. She grew up watching her mom hustle on the side and her grandfather run restaurants in Jalisco — the heart of tequila country. Business wasn’t something abstract or glamorous. It was a way of taking care of people. And it was always there, in the background.

But her world didn’t start with startups. It started in the structure of big companies.

“I was close to the C-level early on,” she says. “The projects I worked on were high priority — but never well resourced. So I had to figure things out. That made me more creative, more independent.”

Michael Jensen never wanted to work with salt. In fact, he hated it.

As a kid, his dad used to bring home eight 40-pound bags of water softener salt and make him carry them down to the basement. That was the worst part of his week. So when his dad suggested starting a salt delivery business, his answer was clear: absolutely not.

But that painful chore planted a seed. And years later, it became the foundation for EZSalt—now scaling fast, with real traction in a space that billion-dollar competitors couldn’t crack.

Bellamy Grindl didn’t set out to become a consultant. She just kept getting hired to fix the same problem, over and over again.

She’d spent nearly 20 years working in retail—big names like Gap and Walmart, plus digitally native brands and startups of all shapes and sizes.

“Every company I joined, I was doing the same thing,” she says. “Setting up their demand planning. Building their data infrastructure. Trying to help them stop flying blind.”

So in 2021, when her last company shut down, she made the jump. Bellamy launched Retailytics, a boutique consultancy that helps founder-led consumer brands stop throwing spaghetti at the wall and start making smarter, more strategic decisions.

Jake Walbert didn’t launch Pagoda Search to “change the recruiting industry.” He started it because he knew exactly how it felt to be on the other side of the interview process—getting ghosted, misrepresented, and overlooked. And he thought there had to be a better way.

“There’s always going to be pain in job hunting,” he says. “But I’ve been that person hoping to hear back before the weekend, sitting on it, unable to be present with friends or family. I know how much that silence weighs on you.”

Lidija Newman didn’t grow up thinking she’d be an entrepreneur. But she knew early on that she never wanted to be trapped.

She was raised in Serbia during wartime. Her dad was an engineer, but like so many others, had to improvise to survive. He traveled across borders, imported goods, and figured out how to provide for the family when nothing was stable. “That was my first view of entrepreneurship,” Lidija says. “Sometimes you don’t choose it—you just have to figure things out.”

That mindset stayed with her. Even as she built a career in fashion, moved to London, then LA, and worked for some of the biggest names in the industry, there was always a restlessness beneath the surface.

“I tried going back into 9-to-5 so many times,” she says. “But every time I felt trapped. I couldn’t express my creativity. I couldn’t live on my terms.”

Michael Raab didn’t plan to start a business. In fact, for most of his 20-year career in ad tech, he did everything but that.

He ran customer success teams. Led support and operations. Helped build account management from scratch. If it touched the customer lifecycle, he did it. The only thing he didn’t do was sell—which makes it all the more impressive that now, as the founder of Raab Insight Consulting, he’s in the thick of it: prospecting, pitching, and closing his own clients from day one.

“I’ve never been in direct sales before,” he says. “But now I’m writing the messaging, doing the outreach, and having the conversations. And weirdly? I actually like it.”

Entrepreneurship wasn’t a buzzword in her house. It was how you lived. How you worked. How you got paid.

“I built a dropshipping furniture business on the side while I was working full-time,” she says. “Eventually, it paid me enough to leave my job.”

It wasn’t glamorous. She wasn’t pitching investors or building a personal brand. She found a supplier, set up a site, and figured out how to sell chairs while working 9 to 5.

That business funded her next move—her real goal.

In 2023, Lorenza launchedSecure AIs, a startup built to tackle one of the most complex problems in tech: securing and sanitizing data for AI development. But unlike the dropshipping days, this wasn’t an immediate win. It’s been slow. Strategic. Painful, at times.

Cameo is no stranger to doing hard things. Her dad—an experimental, self-taught entrepreneur—once mailed her boxes of gold so she could make earrings in her college dorm room. She sold enough of them to pay her tuition. Years later, when her job at a restaurant chain imploded, she stood at the front door and handed layoff checks to every employee—including herself. And when that life collapsed, she chased a dream instead. She tried to become a rock star. Toured the western U.S. as a lead singer. Got some traction. Signed with a lawyer. Didn’t make it.

For years, she didn’t talk about that chapter. It felt like failure.

“I thought I should’ve been successful. And because I wasn’t, I carried shame. But eventually I realized—how many people never even try?” (Give them a listen here!)

Melvin Varghese didn’t grow up dreaming about building a business. In fact, everything in his upbringing pointed the other way.

“My parents actively did not want me to pursue business at all,” he says.

He was supposed to follow the path they carved.

The plan was stable: teach, see patients, maybe go the tenure track. But a mentor gave him a new perspective. “She told me, think of your skill set as something you can deploy beyond the clinic,”

In 2015, he started a podcast—Selling the Couch—to interview other therapists and learn how they built their practices. It was a side project. No real business model. Just curiosity.

Most people don’t build businesses designed to make themselves obsolete.

Mary Southworth did.

Her company, The Shiftly, helps small and midsize businesses clean up their HR and payroll systems—so clean, in fact, that she doesn’t need to stick around. That’s the goal.

“Our whole motto is HR that wants to get fired,” Mary says. “We go in, clean it up, get it organized, hand it back to you, and leave.”

Caitlin Modestine never planned to be on stages, coaching companies, or building a business from scratch. Her earliest ambition was much simpler: become a third-grade teacher. And she did—landing the job at the very school she grew up in. It was a full-circle moment. Dream realized.

But just months in, everything changed. The archdiocese shut down and merged a number of Catholic schools, including hers. Faculty were laid off and forced to reapply for their own jobs. She was rehired—beating out more senior teachers—and taught for two more years. But something had shifted.

“I realized I wanted to work with big people,” she says. “I wanted to make a bigger impact. I just had this calling that I was meant to do more.”

When Candice Thompson first launched her private therapy practice, she didn’t think of it as a business.

She thought of it as a calling.

“I didn’t realize I had a business until I’d had it for over 10 years,” she says. “As therapists, we’re trained in mental health—but there’s no training in grad school around marketing, scaling, branding. None of it.”

What she did have was deep clinical expertise.
Thousands of supervised hours. Years working in underfunded nonprofits. A passion for helping people find clarity and healing.

Jennifer Cresswell never expected to start her own business.

She built her career the traditional way— she worked her way through the ranks of some of the biggest financial institutions in the country.

But over time, the work stopped fitting.

“Corporate life started to feel like a box,” she says. “I realized I wanted more autonomy, more creativity. I wanted to build something of my own.”

When Ryan Welti boarded a flight from Dallas to Miami, she had no plans to start a company.
She was in yoga teacher training at the time—deep in a moment of personal reset—and casually started sketching out retreat ideas in Freeform on her iPhone.

By the time the plane landed, something had shifted.

“I thought—what if there was an Airbnb for wellness retreats?” she says. “That was it. That was the moment.”

It wasn’t her first idea.
But it was the first one she couldn’t walk away from.