How Erin Rollenhagen built a million dollar software business in a recession
In 2007, everyone was naïve about what would happen to the economy.
Erin Rollenhagen was no exception—she was equally unaware of the economic turmoil ahead and the challenges of starting a software agency simultaneously.
Erin is the founder and CEO of Entrepreneurial Technologies, a software agency with over 20 full-time employees based in Iowa.
Yes, the state you might associate only with cornfields and a football team with a questionable offense is home to a highly successful software agency. Who knew?
It's been over 17 years since Erin founded Entrepreneurial Technologies. Let's dive into how she started and grew the company into what it is today.
The start of Erin’s software career
Erin started at the University of Iowa thinking she would become a writer. Within her first creative writing class there, she knew that it wasn’t the right fit. Once, the professor took all of the class’ papers and threw them across the room and shouted, “This is all crap!” it was time to look for a different career path at that time.
Later, Erin became a writer by writing her first book, Soul Uprising, which tells the story of how she started Entrepreneurial Technologies.
After that creative writing class experience, Erin was offered an internship at a software company. She was mostly just excited about the high hourly pay rate. She thought she would be doing the stereotypical intern tasks: typing emails, making copies, and doing a lot of small tasks.
Instead of those tasks, Erin got to see how the team worked and how it changed the original picture in her mind of what creating software looked like. It wasn’t “someone in a basement with a two-liter of Mountain Dew, a bag of Cheetos, and typing ones and zeros.” Instead, it was “a small group of 20 people, in the middle of Iowa, and they got to work on these really big projects and do things that had real impact”.
After that internship, Erin returned to the University of Iowa, got a degree in Management Information Systems, and found herself back at that same company.
This time, she was one of the software consultants.
She loved working there and worked there for over 5 years.
There was still something missing though.
Erin became a software consultant because she wanted to make a difference and see the impact her work could have on the world.
As Erin put it, “The entire time I worked there, I never met an actual person who used our software as an end user.”
Erin’s motivation to become a software developer just wasn’t being met by working at this company. They were doing great work, and she enjoyed the experience, but ultimately, Erin didn’t feel she was making the greatest impact that she could be at that company.
As a slightly naive and overconfident twenty-seven-year-old, Erin decided to start her software agency, Entrepreneurial Technologies.
The start of Entrepreneurial Technologies
Erin didn’t immediately quit her day job at the software company. She started Entrepreneurial Technologies as a side hustle.
Thankfully, the software company she worked for focused solely on government software projects, and her side hustle had nothing to do with those types of projects.
To get her first clients, Erin met a man at a networking group who had his own software consultancy. Although he didn’t do any software work himself, he would refer Erin to do the work instead.
Shortly after Erin started Entrepreneurial Technologies, that same man decided to shut down his own consultancy, and Erin was able to absorb all of those clients into her business.
That ended up helping snowball the growth of Entrepreneurial Technologies as those new clients would refer even more clients to Erin.
As Erin put it, “Word of mouth was pretty kind to us in the early days,” and that was the main driver of growth for Entrepreneurial Technologies back then and still is in 2024. More on all of these referrals later on in this post.
At one point, they invested resources into SEO and ranked pretty high for terms like “iPhone app developer,” which drove a decent amount of people to their website and to fill out the form to become clients, but typically, that wouldn’t turn into a good project.
The best projects and clients came from referrals.
With these referrals, Erin could quit her day job and be full-time on Entrepreneurial Technologies.
Within 2 years of starting, Entrepreneurial Technologies had over $250k in annual revenue.
It has been over 17 years in business, and Entrepreneurial Technologies has grown a ton.
In 2024, Entrepreneurial Technologies is a team of over 20 full-time team members who have worked on any project you could imagine and are headquartered out of Iowa.
The growth strategy of Entrepreneurial Technologies
The growth strategy of Entrepreneurial Technologies has been simple: referrals.
After chatting with Erin about these referrals though, there’s actually two different types of referrals that have grown Entrepreneurial Technologies. Let’s get into them.
Client Referrals
This has been and still is the best referral source for clients for Entrepreneurial Technologies.
Even Erin’s first clients were sending referrals to Entrepreneurial Technologies.
Erin gave this advice judiciously, but she believes clients refer Entrepreneurial Technologies because they “do things a little bit better than people expected.” Another way Erin phrased it was, “You don’t ever want to put work out there that you’re not proud of.”
This is the classic case of underpromise, overdeliver.
It’s easier said than done to say, “Here’s what we’re going to do at a basic level, and then just exceed that a little bit.” It’s human nature (especially for founders) to get excited about what we can all deliver and overpromise because of that.
This is emotional intelligence in some ways. When you’re pitching a client or whoever you’re delivering work to, realize that you’re getting excited or confident about what you can deliver, but take it down a notch for what you’re going to communicate to that person.
Aim for the 5-star plan in your head, but pitch the 3-star plan you know you’ll deliver on.
Industry Network Referrals
From the start of her career, Erin has been active in the local business and startup community in Iowa. That led to her meeting her first referral partner, which snowballed quite a bit.
Erin has continued to be active in the local community, which still helps her find clients, especially now that she’s been running Entrepreneurial Technologies for 17 years. It has quite the reputation at this point.
As a result, she’s built a network of people in the local community who are adjacent to Entrepreneurial Technologies’ work and who will refer clients.
They might be investors or adjacent service providers like marketing agencies that don’t do software work.
This makes sense. Investors might have a company that is growing like crazy but needs a software partner to keep up with growth. If they know Erin or have worked with Erin before, it’s super easy for them to tell that company, “Let me intro you to Erin at Entrepreneurial Technologies”.
The same goes for a marketing agency.
A marketing agency might be working with a client on a new marketing campaign but realize that the client needs some work on the software product before they can make the most of that marketing campaign. As mentioned in the Asia Orangio deep dive, you need marketing and product to work well to have growth.
There are many software agencies in the world, but this deep dive shows how important relationships and trust still are. By exceeding expectations, even just by a tiny bit at times, and doing that for 17 years, Erin and Entrepreneurial Technologies have developed a reputation and a network that creates a growth web that continually sends potential clients their way.