Insights from a serial software startup founder

Meet David Heller, the co-founder of Reimbi: a software startup that enables fast, streamlined reimbursements for job candidates and other non-employees, like conference speakers and contractors.

David Heller of Reimbi

David has achieved a lot of the things early-stage entrepreneurs dream about. He’s able to work for the business full-time and be his own boss, his team has grown, and Reimbi was recently accepted at Tinyseed (a new startup accelerator for early-stage software companies).

All these things have happened within the past couple of years, but David’s entrepreneurial journey goes back over a decade and it involves a few twists, pivots, a little luck, and a leap of faith. Here’s the longer version of the story.

Starting in the corporate world

David spent a lot of time working for others before deciding to start his own company.

I did a lot of work before I created my first company. I was in the Army for eight years, and then I kind of did the corporate America thing. I worked for some big companies (like, I worked for HP for a while). Then I started to migrate to smaller companies because I wanted to get closer to making a day-to-day difference, and that can be hard in a bigger company. You might be super smart and everything, but probably your impact on the company on a day-to-day basis is pretty small because you’re one of 5,000 or 10,000.

Through this experience, David learned a couple of essential facts about himself (he really likes solving problems and making boring processes run flawlessly) and about the problems that businesses commonly face. The idea for his first business was borne out of these realizations and some spare time.

I was living in Colorado Springs at the time but I was working in Denver and commuting back and forth on the bus. So, I’d have 45 minutes on the commute, and a lot of days I’d just sit there and write down ideas for businesses I could create or things I’d like to do.

One of those ideas stuck, and he started his first business—a site that allowed businesses to review other businesses as clients and vendors (essentially a business-to-business version of Yelp)

Gaining entrepreneurial experience

When he started his first business, David says he had no idea what he was doing. His product was software and this was back in 2006, when there were very few resources for new software founders. The business didn’t get too far but he learned a lot from this first entrepreneurial experience. One of the biggest learnings was that he wanted to be more involved in the development of his products.

After that, David decided to learn a bit more about web development and started prototyping concepts himself. That experience led to his second company, where he worked with a co-founder to create event marketing software.

The second company made it a little farther than the first, but he and his co-founder eventually decided it wasn’t quite the right product or the right niche. David says that one of the biggest things he learned with his second company was this:

“It’s relatively easy to build stuff nights and weekends, but it’s really hard to sell stuff nights and weekends. This is especially true when you’re selling to a business because they’re not going to want to talk to you Saturday morning or Thursday at 6 pm. You need to be available at 2 pm in the afternoon. It’s really hard to sell stuff when you’re doing it part-time.

Founding and growing Reimbi

Reimbi started out much the same way as his previous two businesses.

David came up with the idea after he saw how painful the job candidate reimbursement process was—both for candidates themselves, and the recruiting and finance team handling the reimbursement. The process is entirely different from reimbursing employees, and it’s very time-consuming. David says that on average, it takes about 81 minutes of work for the recruiting and finance teams to reimburse a candidate. After that, the candidate has to wait 4-6 weeks to get their money back. All in all, it’s a pretty dismal process for everyone involved.

Shortly after he decided to create a new product to solve that problem, David met his co-founder through an online software development community.

David and his co-founder, Paul, started building the product in their spare time. Soon enough, they had a solution that made employee reimbursements substantially quicker and easier. The tricky part, however, was finding clients to use their new product. Since Reimbi is designed for businesses, the market is smaller and it can take a lot of work to convert a potential client.

David quickly realized, again, that it was going to be really hard to get momentum when he was only able to work on the business part-time.

Reimbi was one of those nights and weekends efforts. We started out with a small Google AdWords campaign to gauge interest from people (other than people I knew) and it was really slow. I began to realize that getting it off the ground would require a lot of work, and I just didn’t want to work 90-100 hour weeks. I had a 50-hour a week job already, and I’ve got a kid and a family and all of that. There wasn’t a lot of time and mental space for the business. So, things were slow. Paul and I had built this thing, but no one was using it.

And I got laid off, for the first time in my life. I was trying to figure out what I was going to do, and I realized … I’ve got some runway now. For the first time in my life, I could work 100% on a project for six months, or three months, or whatever. So, I was trying to decide what I wanted to do. I was thinking, well, “What’s my best idea? Well, my best idea is Reimbi.” I felt like we didn’t give it enough of a shot and it might work with more attention.

He decided to focus on the Reimbi full time (except for a few short-term contract jobs) and his bet paid off. He was able to phase out contract work in February 2019 and his co-founder went full-time on Reimbi in December 2018. Now, Reimbi has been accepted into TinySeed, a new accelerator that provides funding and mentorship for bootstrapped startups. Reimbi is also adding clients, growing the team, and working to achieve ambitious growth goals.

Looking back, he says “No one enjoys getting laid off, but I wasn’t mad. In hindsight, it couldn’t have been better.”

What he’s learned from business #3

David says that each of his businesses has made him learn something new. “You know, I think that’s part of what I like about entrepreneurship and small business. Every day you should be learning something.”

With Reimbi, one of the biggest learnings has been this: “As a B2B company, there are all these hoops to jump through. There are all these steps with legal and procurement. Luckily I worked in big companies, and I’m familiar with these departments and I think that’s helped, but I still learn from every interaction.”

He’s also learned that getting through the hoops is easier if you’ve got a product that people really want, and you’re solving a problem that people really care about. He says, “In every deal, there’s been one person championing the product and the candidate experience, and they are working almost as hard as I am to get Reimbi for their company.”:

When you look back at David’s entrepreneurial journey, it’s easy to see how each step fits together and brings him to where he is today. It’s equally easy to see dozens of moments where it would have been easy to give up, or get discouraged, or take a different path.

If you’re one of the lucky few who starts a business that immediately has rapid, consistent growth and traces a clear trajectory towards profitability and a successful exit, David’s story might not mean a lot to you.

On the other hand—if you have great ideas that don’t always work out quite the way you hoped, and you’ve got tenacity and a tremendous drive to make things better—hopefully, it helps to know that a venture that seems like a false start is actually a step in the right direction, and sometimes a great idea won’t pay off until you get enough momentum.


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Hi there! This post exists to offer you (hopefully) useful information but it cannot take the place of personalized professional advice. Please consult a qualified expert if you have questions about your business. Also, Azlo doesn’t endorse any third-party sites that are linked here.

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