An Idea Walks Into a Restaurant
Des Moines is often described as a business community with just one degree of separation—everyone, somehow, just seems connected. It was in that spirit of openness that I reached out to Erin Rollenhagen, CEO of People Friendly Tech (formerly Entrepreneurial Technologies), author of Soul Uprising: It’s Never Just Business, and a prolific voice at The Revolutionaries’ Notebook on LinkedIn. I invited her to reflect on what it meant to build a startup from within her company—and I'm deeply grateful she accepted.
Erin isn’t a self-professed thought leader or serial entrepreneur, but her actions reflect both titles. Her creative software, art, writing, and speaking all exhibit a passion for human-centricity expression.
Erin’s story below offers something rare: a candid glimpse behind the veneer of startup culture, told with inspiring vulnerability. My minor additions include hyperlinks and callout formatting to lessons learned.
The problem and the benefit of writing an article about a startup nearly 15 years after its demise is that the details fade and you mostly remember the feelings and the lessons. I remember the excitement of starting it, the slog of building and selling it, the sparks of hope at some successes, and the utter exhaustion that led to shutting it down.
Some people might regret failure. I don’t regret much of it—and lest you feel awkward reading this article, I’m not embarrassed by it either. It was a slightly expensive learning experience, but it was absolutely worth it. If we hadn’t done that, we wouldn’t be where we are today, dozens of mobile apps later.
But I’m getting ahead of myself.
In 2011, you really weren’t anyone in the Des Moines tech scene if you hadn’t attached yourself in some way to a startup. The thrill of walking around Startup Drinks with your Peace Tree Brewing Blonde Fatale in hand, sporting a ‘founder’ nametag and your American Apparel tri-blend startup tee, was unmatched.
As a tech consulting company, we’d always been startup-adjacent. We mentored at Startup City. We worked with some local startups. We provided free advice where we could. We had mostly played in the web space and wanted to start doing mobile app development. In the back of my mind, I’d already decided that we weren’t going to learn on our clients’ dime, so we needed our own app to build. The obvious move would have been to turn our client portal into a mobile app, but that sounded both boring and self-indulgent—even to me—so I was on the hunt for an idea.
That was lesson number one: never be a founder on the hunt for an idea. If the idea is that great, it will find you. You don’t have to go hunting.
But a-hunting I went. I was driving back from the Big Omaha conference with Tej Dhawan, all wired on caffeine and startup enthusiasm, having just listened to Bo Fishback’s rousing closing speech as he launched Zaarly. And inspiration struck.
“What if there was an app where people could nab open restaurant tables on the fly?” Two-sided markets were hot, and it seemed like a great place to start: industry-specific but common (everyone eats), so an easily addressable market.
Building the app (and the market)
I had an advantage a lot of startup founders don’t have: a development team at the ready. I quickly pitched it to the Entrepreneurial Tech team (that’s what we were called before our name change). Everyone was on board—we all wanted to get into the app business, and this was our path.
One of our developers at the time, James Armstead, did most of the design work (and did a great job). The logo got less care and attention. We used 99designs and asked people to vote. I cringe a little writing that, but those were the times. Apps were so new and so hot that speed mattered more than just about anything else at that moment. I want to mention here that this is an anti-lesson: the market has dramatically shifted and what worked in 2011 does not work today.
But we got the thing launched. I don’t recall too much about the development process, but I don’t think it took very long—maybe 3-4 weeks. It’s amazing how different things are today, but there were almost no expectations in those days in terms of testing, security, or user experience. You just did your best and went for it. And so we did.
The biggest challenge I recall as a founder was that it required me to go, in person, and pitch restaurants to sign up. As an introvert, this was a character-building experience. I remember sitting in my car in an empty restaurant parking lot at 2 p.m. on a weekday, psyching myself up to go in there and sell.
Restaurants were wary (Groupon had just had its big moment, and many restaurants had not had positive experiences) but open. We got over a dozen to sign up initially. Then came the next hurdle: getting participants on board.
We had some help from in-person startup events. Dwolla let us pitch at one of their meetups. The Des Moines Register and Silicon Prairie News both covered the app, both leading to a spike in downloads and requests. It was happening!
But there was a problem. We had expected that most people who put out a request would ultimately book a table. I am still amazed at this little bit of hubris on my part. I work in tech. I know that conversion rates are notoriously low—generally single digits. And yet, we thought our app would be the exception. It wasn’t.
The reason this presented a problem is that restaurants were individually responding to each request. In order to have their people trained and take the time to respond, they needed to see a return. With up to three restaurants presented to each customer, and customers having single-digit acceptance rates, it was too discouraging for restaurants. They’d have to respond to 100 requests just to get a single customer. That wasn’t worth it to them.
This is lesson number two: do not assume you are the exception to established truths, especially around human behavior. Your business model needs to be able to survive in average conditions, not exceptional conditions.
The broader picture
Ultimately, Des Moines was not a good test market for this product. We had lots of community enthusiasm, but most people didn’t need to wait for a table in Des Moines, so the benefit to the consumer was low—and the incentive to actually book was also low. Our conversion rate hopes were certainly way overblown in any market, and we also chose a market that didn’t really need our product, so they were even worse than they likely would have been elsewhere.
We soldiered on. I hired some part-time, commission-based salespeople (mostly my friends) to get restaurants on board, and we kept at it—releasing some needed updates and continuing to work on the little problems that come to any startup.
Despite the hurdles, we managed to obtain enough traction that some advisors were suggesting I should move to Chicago or San Francisco to make a go of it. That was a wake-up call for me: I didn’t want to do that.
I was also coming to terms with the fact that I’d started an app without any real passion to see it through. I wanted the experience of doing it, and I wanted our team to acquire the technical experience, but this wasn’t a problem that I stayed up at night pondering (at least, not until I put 50K of my own capital into it). I didn’t have the intrinsic motivation necessary to see it through. It was a fun adventure—or it seemed like it when I started.
This is the third lesson: if you’re looking for an adventure, go backpacking. Jump out of an airplane. Climb a mountain. Do not start a startup—it takes a lot of grit and determination, and a taste for the unknown won’t sustain you through that.
I was also privately fighting a health battle at that time. Over a series of months, I lost strength and mobility in my body and was ultimately diagnosed with young-onset Parkinson’s Disease. In a miraculous twist, I found out years later that it was a misdiagnosis, but at the time, I was dealing with some debilitating symptoms and the pressure of trying to hide it, because being sick really wasn’t a part of the whole startup founder program. I was also going through a divorce at the time.
Lesson number four: you’ve got to account for your own readiness to take on the needs of a startup. It needs your time, your passion, your energy, and your money. I didn’t feel I had enough of any of those to give.
Eventually, I decided—with some relief—to shut it down. Strangely enough, I don’t really recall much about the decision or the time. I know my heart wasn’t in it, and I was scared and sick. My one regret is that I didn’t do enough to communicate with those who supported us, especially the restaurants, when we decided to shut down. I didn’t think I had the energy, but it would have been more dignified to communicate with them in person, and I didn’t do that.
Which brings me to the final lesson: this Iowa community is supportive and warm. But that’s not enough. People will download something once to support it, but they will only make it a part of their lives if it fulfills a genuine need.
Would I do it again? No, not that way. Most of my lessons were signals that I shouldn’t have picked that particular idea in the first place. But I wouldn’t undo it either. That kicked off a series of events that led to our successful UX and app development agency, and sometimes you need those early at-bats to get experience – even if you strike out.
I had a personal connection to Startup City Des Moines and was able to join Erin on some of the restaurant sales visits. Our city’s restaurants who opened their doors to try a startup’s early product are deserving of much love and credit. The meetings I vividly remember 13 years later at Table 128 and Open Sesame underscore the important role early customers play in defining (or euthanizing) a product.
Lessons such as these are painful to experience but leave lasting impacts on business. Erin’s massive engagement with the community’s businesses is a testament to that legacy.
I am a proud member of the Iowa Writers Collaborative and the Iowa Startup Collective. Each writer is independent and publishes via Substack across Iowa and I hope you are able to explore my fellow amazing writers’ work.
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"In 2011, you really weren’t anyone in the Des Moines tech scene if you hadn’t attached yourself in some way to a startup. The thrill of walking around Startup Drinks with your Peace Tree Brewing Blonde Fatale in hand, sporting a ‘founder’ nametag and your American Apparel tri-blend startup tee, was unmatched."
thanks for the quick trip on the time machine! miss those days
Well done, my friend! 🌺❤️