Steve Wilbourne of Questis

An exclusive Tech Tribune Q&A with Steve Wilbourne of Questis, which was honored in our:
Tell us the origin story of Questis – what problem were you trying to solve and why?

I worked as a financial advisor for 25 years. After the 2008 financial crisis, I saw that even the 1% of people I was serving were struggling financially. So with 75% of people living paycheck to paycheck, why in the world would we be talking to them about saving for retirement when they can’t handle even a small unexpected expense and have to put it on a credit card because they have no emergency fund? There was a huge need to meet employees where they are on their journey, and provide financial guidance around everything from budgeting to investing and everything in between. I realized that a fundamental change in the way all people see and engage with their personal finances needed to take place immediately. That’s when Questis was born.

I partnered up with John Tabb, Questis co-founder, and we pulled together a team of passionate builders, engineers, financial advisors, and visionaries who all share one driving goal: to bring the value of financial healing and empowerment to everyone.

Combining the accessibility of software with the power of actionable, personalized financial guidance, Questis bridges the gap between people and their financial health. By getting to the root of the problem and offering customizable solutions that scale with coaching, plus the power of software, we can both redefine financial health and offer actionable ways for people to achieve and surpass their goals. Saving for retirement is necessary, of course. And at the same time, people have more immediate questions, like “How am I ever going to pay off my student loans?” or “How on earth do I buy a house?”. Questis can help.

What was the biggest hurdle you encountered in your journey?

Resource constraints – human and financial. Finding the right people and managing the human capital piece when you’re in early stage start-up mode. But, when you find the right people, things start to happen. Remote work is allowing us to source great talent from everywhere, and we’ve built a team that works hard and is inspired to work together. And we’re finding greener pastures in where the company is now and where we are heading.

What does the future hold for Questis?

I believe that in too many organizations, retirement benefits have become the cart put before the horse. People have more immediate financial needs in addition to retirement, and that’s what too many employers are not addressing. Retirement is really the only financial benefit in the workplace currently, but people have additional financial needs. For example, we would love to see companies matching employees’ ability to get out of debt the same way they match their 401k.

What we are doing is changing the way benefits are defined and delivered. Financial empowerment is personal and intelligent, personalized to the individual in the workforce, no matter where they are in their journey. Questis sets employees and employers up for success today and tomorrow.

What are your thoughts on the local tech startup scene in Charleston?

In the past, Charleston’s prosperity has always been driven by the port or hospitality. The tech scene is the best growth opportunity Charleston has going for it now. There are some established investors looking to put money in early-stage companies. Good Growth Capital is a great example of that, and that kind of funding is so important – it’s the lifeblood of young companies getting their feet on the ground. It’s a critical first step to become healthy and thriving. We all benefit when we have more technology innovation and more demand for talent. A growing tech scene means more talent coming to Charleston, which also brings business diversity. New money moving to Charleston could take a role in the local tech community and help it all to blossom.

What’s your best advice for aspiring entrepreneurs?

It’s a marathon, not a sprint. If you believe in what you are doing, you keep working until you find a way. You never know when your breakthrough is going to happen. The only difference between a successful and unsuccessful startup is that one said, “I can’t take it anymore”. You’ve got to be willing to live through tough times. If it were easy, everyone would do it. It’s not going to be a layup.


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