My First Year as an Entrepreneur: An Exercise in Humility
One Millennial’s story of overcoming failure in hopes of uniting generations through technology.
Fifteen months ago, I started a business with my older sister. It was exciting to the point of being scary, socially fulfilling yet financially disheartening, and a lot of fun but incredibly stressful…
But more than anything, starting your own company is humbling. There is no better framework for failure. While most people cringe at the thought of setbacks, negative feedback and rejection, entrepreneurs must learn to thrive on it.
I was so naive. Having taught my technophobic 82 year grandmother how to use an iPad, I was absolutely sure I had found a wide social need and had the skills to fill it. “Find a need and fill it!” That’s all there is to a successful business, right?!
It was obvious. Who wouldn’t want to help their beloved Grammy, Nana, Gramps or PapPap learn how to use an iPad? All I had to do was outline the methodology, package the training resources and our service goes viral. Six months later I’ll be in Cupertino with Tim Cook, jiving each other over who has more fuel points as we talk acquisition.
Boy was I wrong. Younger family members and friends were either too busy, not patient enough or completely uninterested in training. Even more troubling for our fledgling business, the 70, 80 and 90 year olds were too intimidated or resentful towards technology to want to learn something new.
I decided to take on the training myself, and for months, I had trouble giving it away. My first attempt to offer our service at a 50+ Expo trade show in Hershey, PA was a disaster.
Alongside countless retirement communities, health care services and local contractors, our booth was the lone technology exhibit. I enthusiastically recruited foot traffic to show off iPad features and offer complimentary training sessions. Most smiled politely and declined my offer, or assured me that they were “too dumb” to learn. One lady was interested and asked what it could do — FINALLY!
After coaching her through viewing photos, I explained that FaceTime would let her talk face to face with anyone in the world. She tapped on the app and gasped in horror as her own image displayed on the screen via the front facing camera. She dropped the iPad on the table and hurried away from the booth before I could explain.
I left the trade show feeling defeated; hundreds of attendees and no one took me up on my offer for iPad training. We had invested thousands of dollars and six months of our lives and were still without a single customer. And our service was free!
There had to be a better way to encourage potential students and convince them that the iPad wasn’t just some futuristic toy with angry birds and fruit ninjas that consumes their grandchildren during family get-togethers. It is a tool to sharpen their minds, open a new world of learning opportunities, and transcend time and space to help them stay connected with loved ones.
This challenge led to the birth of our ReThink Technology presentation — a cross between a motivational speech and technology magic show. Discussing the current dynamic surrounding technology and different generations, we make the case for changes at both ends of the spectrum.
For younger generations, our message is to value face-to-face communication and recognize that technical savvy is not a direct indicator of intelligence. “We are all ignorant only in different topics!” — Hey Mr. Knowitall eighteen year old, your mom is not stupid because she doesn’t understand the new Gmail interface; she was preoccupied for a couple of decades raising children and juggling a career.
For older generations, the challenge is to let go of frustrating past experiences with computer crashes and viruses. With an open and clear mind, it is much easier to understand what is now possible through modern day technology. With a few taps from an iPad first-timer in the crowd, the Google Search app responds to a voice request for Cary Grant movies, my Gram stops in for a FaceTime call, and we trade pictures via email with former iPad students (we call them the Generation Connect family).
ReThink Technology was gold, and we took every opportunity to present it — community centers, libraries, churches, hospitals and anywhere else that provided a captive audience. The response was overwhelmingly positive, and soon I had a backlog of training opportunities.
Just as soon as I had my first taste of success as an entrepreneur, I came to the realization that this service would not grow effectively. The logistics of coordinating small group trainings, preparing devices, helping with wireless connections and providing support made these services impossible to offer at a competitive price point.
We decided that the only way to scale the service was to go back to our original idea of “training the trainer” but with a more specific focus. By providing iPad training methodology and documentation to senior living staff, we could help them add value to their communities.
Having no experience in the senior living market, I reached out to an industry leader for help on promoting technology in this marketplace. After I drove over four hours for the meeting, she opened by informing me that our service would fail because senior living communities have always resisted technology. Of course we might have a chance if we paid for access to her network of connections through a $9,000 “minimum consulting engagement”…I passed.
However, her point had some basis in truth. Most communities were not interested in paying for a service to enhance the lives of residents, if it didn’t affect their bottom line. After months of cold calling, presentations and rejections, we finally got our first opportunity.
At Bethany Village, a community in Mechanicsburg, PA, we hosted our ReThink Technology presentation to “gauge interest”. Over 70 people attended and practically demanded that the community partner with us to offer Starter Classes and monthly content. Soon thereafter, we partnered with a handful of new locations, largely in part to the resident enthusiasm following ReThink Technology.
Working with staff at our first group of partner communities, we discovered an added benefit of the iPad training classes — members of the public were interested in attending and participating! Not only was this an opportunity to generate additional revenue to cover the training costs, but more importantly it exposed the public to their community facilities and commitment to residents.
With this potential marketing benefit in mind, we started to pitch the sales team at prospective communities. They were much more receptive, recognizing the potential to differentiate their community and attract the next generation of residents. This new strategy has resulted in an influx of new partner communities.
If I had known how hard it would be, I may not have ever started down this path. Now I am addicted to the entrepreneurial lifestyle and look forward to the inevitable adversity that awaits.
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