From Rideshare Driver to Startup Founder: How Chad Mastagh Built Rides2U on Faith and Grit

Chad Mastagh will be the first to tell you he's "just a dumb fireman." He puts wet stuff on the red stuff. He fell asleep reading the Bible this morning. He has ADHD, barely reads books, and watches Shark Tank every night until he drifts off.

He's also the founder and CEO of Rides2U, a rideshare platform that has raised nearly $2 million since 2021, is on pace to process $2.5 million in rides this year, and is preparing for a Series A that will push expansion to 100 locations across the country.

And if you ask Chad how all of this happened, he won't lead with his business model or his funding rounds. He'll lead with what happened when he nearly ran out of money and got on his knees.

The Problem Nobody Wanted to Name

It started nine years ago with a favor. A coworker at Ryder Truck Rental asked Chad to do five rides on Uber so he could collect a referral bonus. Chad had no idea what he was getting into — but once he started, his competitive instincts kicked in hard.

He found Facebook groups where drivers shared strategies. He upgraded to a larger vehicle. He became obsessively good at the craft. And soon, riders — especially around Notre Dame — were hunting for ways to book him directly, slipping him their Venmo and phone numbers, unwilling to risk getting someone else.

Before long, Chad was running what amounted to a private car service, doing $60,000 to $70,000 a year through Venmo alone. But he noticed something nobody was talking about: the drivers his customers thought were covered by commercial insurance weren't. They had personal auto policies and no protection if something went wrong.

"People do this all over the country every day. They think they're safe because the driver passed a background check. But commercial insurance costs $8,000 to $13,000 or more a year, so most drivers just skip it."

Chad got the commercial insurance. He built the compliance. And when the Notre Dame Idea Center invited him to pitch in 2021, he showed up not entirely sure what a pitch competition was — genuinely wondering if they were playing some kind of baseball.

They won the best community idea award. And Rides2U was born.

The Pivot That Changed Everything

The early version of the business was straightforward: grow organically, serve college markets, build a brand as the safe, reliable rideshare alternative. But as Chad expanded, he kept running into the same character again and again — a driver in a college town or suburban market, doing great volume, beloved by their customers, managing a complex schedule through text messages, and completely uninsured.

One of those drivers was running a thriving private rideshare operation near a major university, juggling dozens of clients, building a real business — and when Chad called her out of nowhere, she assumed he was a scammer.

He wasn't. He was offering her a lifeline.

The model Chad had been building quietly clicked into focus: Rides2U wouldn't just be a rideshare company. It would be a platform — almost like Shopify for independent rideshare operators. Partners bring their existing book of business. Rides2U handles the app, the payments, the commercial insurance, the compliance, the 24/7 customer support. The partner just drives. Or manages. Or both, at whatever level they want.

"None of us can become Uber alone. They spent $32 billion at a loss over the past 15 years to own that brand. But if thousands of us across the country come together under one umbrella, we can get there a whole lot faster — and we've all got the local trust they'll never have."

Their biggest partner, a driver in Detroit, came in with a $350,000 book of business. Two weeks into the transition, he called Chad while he was on vacation in Florida, ready to quit. Chad talked him back from the ledge. Today, the Detroit area driver drives and lets Rides2U handle everything else. His words at a recent dinner together: "My nights are back. My life is so much easier. I just had to trust."

Running Out of Money — and Into Something Bigger

The summer of 2023 was the moment Chad stopped pretending this was all his doing.

The company was burning through its runway. Fundraising had slowed. Chad had long since stopped driving himself — he'd given all the rides to his drivers, which meant no side income — and the savings were thinning fast. He wasn't drawing a salary. The pressure was relentless.

He prayed. Not a polished prayer, but the real kind — the kind where you admit you don't know what to do next.

"I wake up the next morning and I just felt it clearly: cash out your Ryder 401k. I had completely forgotten I had it. I told my wife, and she said, as long as you don't touch the fire department retirement, I don't care what you do."

He cashed it out, paid the early withdrawal penalties, put part of it in his personal account and the rest into the company. Enough to survive the summer. Within two days of making that move, a passenger he had driven months earlier called from California with a $195,000 investment commitment. Days after that, a connection through the rideshare industry came in with another $25,000 and a second business opportunity that licensed the Rides2U technology into the bus industry.

"I try to be obedient," Chad said simply. "And then all this happens."

That season didn't just save the company. It changed how Chad carries himself as a leader. The hustle was still there — it never really leaves a man who grew up grinding — but something beneath it had shifted. The business wasn't just his anymore. It was something he'd been entrusted with.

Preaching From the Mountaintop, Whether It Costs You or Not

A few months later, Chad drove down to Muncie to watch his daughter and her husband get baptized at a small church. The pastor delivered his message that Sunday morning having lost his son — a police officer struck and killed on the side of the road — just three nights before.

He preached anyway. He talked about praising God in the highs and in the lows. He talked about being used as a vessel, growing up in the trailer parks of Muncie, and how none of us fully know what we're supposed to do with the platform we've been given.

It hit Chad harder than he expected.

"I always joke that I'm a dumb fireman. But in that moment I thought — you're supposed to use this opportunity to shout from the mountaintops every day. God did this for us. He provided the way."

Not long after, a board observer reached out and flagged that Chad's increasingly faith-forward posts on LinkedIn might put off potential investors ahead of a Series A. Chad's response was immediate and unambiguous: "If someone won't invest because of my faith, that's not the right investor. God will give me the right investor. I'm not going to stop."

He carries a small cross in his pocket now — the kind he first saw on TikTok, the size of a thumb. When he drives and feels road rage creeping up, he reaches for it. When he gets anxious about the next funding round, he reaches for it. And when a conversation at the fire station turns toward faith, he gives one away.

What This Looks Like on Monday Morning

Chad Mastagh is not a polished motivational speaker. He's a 22-year firefighter working his weekly shifts, a founder managing partners on the edge of walking away, a husband who married the woman from the front row of his parents' church and has been figuring it out together for nearly 28 years. He falls asleep to Shark Tank.

But there's a throughline in everything he's built, and it's not a business strategy. It's a posture — a willingness to act on what he's heard in prayer even when it doesn't make financial sense, to credit God out loud even when it might cost him, and to keep going when the runway is short and the answer hasn't arrived yet.

He's not waiting until his faith is perfect to integrate it into his work. He's doing it now, imperfectly and publicly, because he believes the opportunity in front of him is bigger than him — and that believing that changes how you lead.

"I'm like, Lord, I'm a terrible Christian. But I feel like if I stop talking about what He's done, I'm letting Him down. And I'm not willing to do that."

The Series A is coming. The hundred locations are coming. The $25 million in ride volume is coming. But if you ask Chad Mastagh what the real story is here, he'll tell you it's simpler than that: he prayed, he listened, he acted, and somehow — in ways that still surprise him — it worked.

Maybe the question worth sitting with this week isn't whether you have enough funding, enough traction, or enough certainty. Maybe it's whether you're willing to be obedient before you have any of those things.