Spotlight on Small Business Owners: Darren Smith, Traipse

Spotlight on Small Business Owners: Darren Smith, Traipse
Darren Smith

Darren Smith spoke to us about finding the right balance of visibility and control over accounting and admin tasks while staying focused on running his startup, Traipse.


The mobile app startup Traipse guides users through streetscapes, historic landmarks, and locally owned businesses while challenging them with scavenger hunts and puzzles. When Founder and CEO Darren Smith aimed to solve the puzzle of accounting and payroll, he found a guide in FINSYNC.

We spoke with Darren Smith about how Traipse got started, the challenges and successes he’s faced as a startup, and how he’s found the right balance of oversight for his accounting.

What inspired you to start Traipse?

I started with a background in urban planning and have a passion for the historic business district as an important piece of the economy, and of our society. That was the underlying thing for me.

Then, for about ten years the Washington Post ran an annual event called The Washington Post Puzzle Hunt which brought thousands of people downtown to solve puzzles they had set up. Before that, my hometown radio station used to do a treasure hunt where clues would be posted in local stores.

So the idea was a combination of those things — a way to engage local merchants and to get people out exploring and learning about different places, whether or not they live there.

That got my brain thinking about how something like that could be built to run at any time. I set out to create an app that lets people in a neighborhood or business district solve puzzles built around things that are always there: signs, statues, etc. 

What are some of the biggest rewards of running a small business?

The flexibility is nice. There are things that I never anticipated in terms of what it does to your psyche. To always be thinking that you need to be working to build the business. But, particularly early on, for the first years of my son’s life, I was able to be home with him three days a week and work on the early stages of the business. That was great to be able to do that.

In terms of the business itself, it’s really cool to create something and then hear from people who have used and enjoyed it. We hear from people who have walked through an area hundreds of times and never knew or noticed something. Or to hear from local merchants who are able to increase business from the added foot traffic. That piece is unique to our business and makes it really rewarding.

What are the biggest challenges you’ve faced as a startup? 

For someone who had not done this before, and didn’t come from a business background, there was a lot of learning I had to do and mistakes that were made. Things that if I had known six months ago I could have avoided. But there’s no instruction manual.

Some of the challenges related to capital, especially with a business like this where you’re trying to build a user base while making sales. Our model is we have contracts with local tourism and business development organizations. So we’re trying to please a lot of people. Sometimes the things you need to do to build a user base versus a client base can make it difficult because you are allocating resources to two different areas. It is the challenge of a B2B2C business. 

Why did you choose to start working with FINSYNC?

We’ve been FINSYNC users for a long time. I hadn’t done really good accounting of the business to that point and I was about to start getting everything into Quickbooks. When I heard about FINSYNC, it sounded like it was more tailored to the needs of a startup and had other tools that no other provider had at that point. It was very appealing to me.

It seems easier to manage as a business with investors and various revenue streams. We haven’t really taken advantage of a lot of the FINSYNC features. I hope to be able to do that in the future. We’re currently laying the foundation needed to do some of those more advanced things. I’m looking forward to getting to the point where we’re able to take advantage of the different possibilities.

What challenges has FINSYNC helped solve?

I feel like it’s the right place on that spectrum of hands-on and hands-off. It is the most affordable solution that I know of that allows me to manage accounting, payroll and other administrative tasks that as a startup founder I don’t want to be dealing with. I also don’t want it to be a black box that I’m not aware of at all times. To me that was the biggest advantage.

Do you have any advice for other small business owners?

You need to figure out early on where on that spectrum you want to be. Also where you can be in terms of how much you want to manage your own accounting and how much you want to or are able to turn that over to someone else. Most startups can’t afford to pay a full-service accounting firm to do all this stuff for them. FINSYNC allows a founder to affordably turn some of that over to other people who know what they’re doing. It allows you to have some automated processes, synced accounts and other features that allow you to generate reports very easily and create the types of things you need as a founder.

My advice is to figure out early on how you’re going to address your accounting and payroll as a business. Then, figure out what tools are out there. Focus not just on the functionality they offer, but where on that continuum they allow you to be to suit your needs.

Helping small businesses is our core mission at FINSYNC.

Centralize your accounting, payroll, and cash flow management on our all-in-one platform.

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