Founder’s Friday featuring Chad Mastagh @ Rides2U

Chad Mastagh, CEO of Rides2U

Please provide a brief description about your company.
Rides2U is the operating system for local transportation operators. Think Shopify for local transportation: one platform for booking, dispatch, payments, compliance, and insurance, so independent operators can run and grow their business like the big players. Founded at Notre Dame in 2022, Rides2U powers reservation-based rides with guaranteed reservations, flight tracking, and Instant Booking.

What do you consider your greatest achievement?
My family. Being a husband to Nancy and a dad to my kids is the thing I’m proudest of. Professionally, it’s building Rides2U from an idea at Notre Dame into a platform that helps local operators grow, all while serving my community for 22+ years at the South Bend Fire Department.

What is your idea of perfect happiness?
A day where my faith, my family, and my work are all in sync. Time with the people I love, knowing I helped someone, and ending the day grateful.

What is your greatest fear?
Not making the most of the time and opportunities God has given me. I never want to look back and wonder “what if.”

If you could change one thing about yourself, what would it be?
I’d be more patient. As a founder I want everything done yesterday, and I’m learning that some of the best things take time to build right.

What are your top tips for balancing work and life?
Put faith and family first, and schedule them like a meeting you can’t miss.
Be fully present wherever you are. When I’m at the firehouse, I’m all in. When I’m home, the phone goes down.
Build a team you trust so you don’t have to carry everything alone.
Rest is part of the work, not a reward for finishing it.

What is something new that you learned about running a business this year?
Speed matters, but focus matters more. We launched Instant Booking and expanded into new markets this year, and I learned that saying “not yet” to good opportunities is what lets you execute great on the right ones.

What is your most marked characteristic?
Persistence. Twenty-plus years in the fire service taught me to keep pushing when things get hard, and that carries straight into building a startup.

What is your greatest regret?
Not starting sooner. I spent years thinking about building something of my own before I finally took the leap.

What is your motto?
Show up, do the work, trust God with the results

What is a legal mistake you wish someone warned you about?
Underestimating how different the rules are from state to state. Transportation regulations and permit requirements vary everywhere you go. Get experienced counsel involved early, before you expand, not after.

When running your business, what do you struggle with most?
Time. Between the fire department, family, and building Rides2U, there are never enough hours in the day. I’ve had to get disciplined about delegating and trusting my team to own their pieces.

What advice would you give to yourself at 25 years old?
Bet on yourself sooner. Your experience is worth more than you think, so stop waiting for the perfect moment. Stay close to your faith and your family, surround yourself with people who make you better, and don’t be afraid to fail. Every setback is training for what’s next.

Tricia Meyer 301

Tricia Meyer is Founder + Managing Attorney of Meyer Law, one of the fastest growing law firms in the United States. Meyer helps entrepreneurs and technology companies from startups to large corporations with day-to-day matters and notable clients include companies that have appeared on Shark Tank to companies gracing the Inc. 500 to some of the largest companies in the world.

Tricia has been named on the Forbes Next 1000 list, is one of the Most Influential Female Lawyers in Chicago according to Crain’s Chicago Business and been recognized as a top 10 technology lawyer.

As an entrepreneur and a lawyer, Meyer has a unique perspective and has mentored thousands of startups and scaling companies at tech incubators and accelerators across the United States such as 1871, WeWork Labs and Techstars. Tricia has been featured in Inc., Crain’s, Chicago Tribune, NBC Chicago, American Express OPEN Forum, and more. Learn more at www.MeetMeyerLaw.com and follow Meyer Law’s story on Instagram @loveyourlawyer.