Here is everything Ben Rapkin learned from the life and death of his startup - Technical.ly Delaware

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Jan. 26, 2017 12:45 pm

Here is everything Ben Rapkin learned from the life and death of his startup

In a remarkably self-aware guest post, the UD grad outlines his startup war stories and how you can learn from them.

ProjectedU cofounders Ben Rapkin and Austin Crouse when they presented at NYC Media Lab 2015.

(Courtesy photo)

I felt like I was dropped off a cliff when my team and I were forced to close down our most recent startup, ProjectedU. Over two years of work, thousands of hours, hundreds of meetings, all for what?

It is not easy to learn from failure. Ego and emotion can get in the way of rationality when you have dedicated thousands of hours to a project with seemingly no return.

After experiencing a few failures in the past, I knew that this was an opportunity to learn from my mistakes. Since there seemed to be interest in the recent Technically Delaware article about my startup journey, I’d like to take the time to further explain the most important lessons from my experiences founding ProjectedU.

The ProjectedU technology acts similar to previews at a movie, but with university and employer information. (Find Technically Delaware’s first story about us from May 2015 here.) It is a communication platform that displays images and videos to students before class begins using the room’s existing projection system. Our database intakes class schedules and rosters to enable micro-targeting of specific student groups with relevant messages and on average engaged 89 percent of its intended audience. You can learn more about ProjectedU and my thoughts on higher education issues on my Linkedin. I am sharing these lessons because I hope you can learn something from my experiences that will give you a better chance at succeeding in your own endeavors.

1. “Why” is the most important question you need to ask yourself.

You have to ask yourself WHY you are starting a business, and you have to be honest with yourself. Are you starting a business to solve an important problem or to make a ton of money? What is your vision and when have you succeeded? How will your company mission guide you and your partners to success?

Since it seems like a lot of people are attracted to entrepreneurship because of the potential to add more commas to their bank account balance, I should tell you that starting a business is one of the most difficult ways to make a lot of money. I’m talking about eighty-hour work weeks, every week for months with no pay, and that’s if everything goes as planned.

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You are going to get hit and you need to be able to remind yourself why you are going to get back up.

For ProjectedU, my cofounder Austin Crouse and I worked together every day before, during and after class, and in between school and work. Whenever someone asked me about work I’d say, “I work 9 to 5 for the man, and 5 to 9 for ProjectedU.” Austin and I worked a 22 hour shift the day before our products went live in UD’s classrooms, and that really takes a lot out of you.

The main reason to ask yourself “why?” is because you are going to get hit, and you need to be able to remind yourself why you are going to get back up. You are going to get hit by the word “no”. You are going to get hit by fatigue. You are going to get hit emotionally by the friends and family you are neglecting to pursue your vision.

Austin and I started ProjectedU because we wanted to help our classmates make the most of their time in school. We noticed students feeling lost and helpless drowning in debt, and we wanted to help them find their respective paths. If your answer to “why?” is money, that’s cool. Just know that in the time it takes to build the foundation of a business, you could have made at least six figures working for someone else.

2. You choose your fate when you architect your business model.

Some businesses are harder to execute than others. For example, investors used to tell me, “I stay away from fed, med and ed.” They used that little tidbit to explain quickly that government, healthcare and education are risky industries with a ton of red tape, and a billion reasons not to change or adopt your idea. They are right, but that won’t deter an entrepreneur who honestly answered the “why?” question above. You, as an entrepreneur, can choose to disrupt these industries, or go for the low-hanging fruit.

Research and in-person interviews with potential early adopters are key to figuring out a working business model. What is the hardest thing you need to accomplish to make this model work? What is the easiest? The hardest part for ProjectedU was getting old giant universities to trust a technology built by two undergrads. The easy part was inventing the first ever in-classroom projection-based communication platform.

The key to failure is trying to please everybody.

Additionally, when you design your business model, it helps to design it for a very specific group of potential early adopters. The key to failure is trying to please everybody. The idea is to build a small tribe of people who love what you are doing and grow organically. In other words, you need to architect a monopoly, a very small one.

For ProjectedU, there were a bunch of competitors in the university digital signage market. However, none of them were able to get inside the classroom and none of them had a captive audience like ProjectedU. Those unique differentiators would allow us to swoop in and redirect advertising budgets being used for less impactful digital signage. The plan was once we had built a tribe of students and professors and employers using our products, that we would be able to chip away at other, more deeply rooted communication systems being used in universities and leverage the trust we earned to secure more business for ourselves. How are you going to create a tribe of people who trust your business and agree with your mission?

3. Crafting your story is vital to success.

What story are you going to tell and who are you going to tell it to? Are people able to connect directly with your mission or do you need to tell them a story to hook them in? For ProjectedU, we told the students that we wanted to help them identify and explore learning opportunities outside the classroom. We showed the university administration that the platform works exponentially better than email, and we told our Fortune 50 clients that this is an entirely new and underutilized way to recruit specific groups of students. Those stories got us through the red tape of the university and into over 70 classes and secured us a dozen clients for the pilot in just a few weeks.

This is also connected to your “why?” reasons from the first lesson. Your story and your purpose can be intertwined and can have a very powerful emotional impact when used correctly. Think of how Duracell shares stories about firefighters powering life-saving flashlights with their batteries to rescue people in thick smoke. Those same batteries are used to power tobacco vapes but Duracell chooses stories that facilitate emotional connections with their brand. For a startup, creating trust and emotional connections with your tribe can make the difference between success and failure. What are you trying to accomplish? Why does it matter? And what story are you going to tell to attract the right people?

4. The importance of having a partner with different strengths and weaknesses.

Peter Thiel says that a startup is “the largest group of people you can convince of a vision for a different future.” Well, for ProjectedU that started out as Austin and me. We were aligned in our mission and our vision, but we had very different strengths and weaknesses. Austin is a great technology designer, with the ability to invent hardware and improvise solutions on incredibly short timelines. I did not have those hard technical skills. I was better at building relationships, understanding the needs and problems of others, and crafting stories. We did have some things in common, like our birthday, our entrepreneurial ambition, and our commitment to each other.

The cofounders after they finished installing their product for the first time.

The cofounders after they finished installing their product for the first time.

Aside from mission alignment, having a complementary partner allows your team to generate and maintain momentum. While Austin was designing circuit boards, I was curating content for classrooms. We would make goals and deadlines for ourselves and come back later with progress in multiple areas. The Gant chart was a good friend of ours and consistent forward motion created small accomplishments to boost motivation during the hard stretches. There is a lot that goes into choosing a great business partner, but I didn’t realize how lucky I was to find Austin until we really got moving with our startup.

5. Be ready to pivot.

At some point you have to stop planning and actually execute your vision. This is where I have seen a lot of people get stuck because they know they have a better chance at success if they think ahead. Some people never build up the courage to implement their ideas, and I think that is a real shame. However, there is good news for those who jump in! It turns out that your startup can have a built in steering wheel, and you can change it’s direction. In fact, it is very common for startups to pivot based on what they are learning during implementation.

For example, ProjectedU was originally planning on monetizing by selling a percentage of airtime in classrooms to major consumer brands like Sperry’s, Red Bull and Rayban. However, when we implemented the communication system in classrooms, the professors did not want advertising in their learning sanctuaries before class began. We had to pivot the startup’s revenue model to something the professors could not complain about, so we chose job opportunities. These same brands could post recruiting messages instead of advertisements, and we could push back against professors by saying we were helping students find jobs.

Sometimes pivoting is not this straightforward, but if you consider it an option at all times, then a perfect situation may present itself to help you navigate around a major roadblock. It is also important to note that it is easier to pivot a smaller organization because there are fewer people and fewer moving parts.

6. Learn how to deal with red tape.

Many large organizations, especially in the so-called fed, med and ed have deep, multi-layered organizational structures with responsibility spread across departments and teams. This can create serious challenges when it comes to finding decision makers, internal champions and getting things done. Even if everyone in the entire organization was on your side and supported your mission, all of the regulations and paperwork and people needing to be looped in could kill a startup with time.

As for ProjectedU, we held dozens of meetings with professors, students,  administration, local businesses and recruiters. It took months just to get the meetings we wanted, and then more months to actually see results from those meetings. These long sales cycles are what eventually put us out of business.

I spent so much time in the fast-moving entrepreneurial buildings on campus that I forgot there were “drifters” in the world: people who just want to show up, get their paychecks and go home. They fear change, don’t like extra work and are often unconvinced by startup missions and stories. I learned that if you encounter a drifter, it is best to leave them and find another person who can help.

Austin and I happened to identify multiple internal champions at our pilot university. The director of career services was our biggest supporter, and the CIO put together a committee to help evaluate the platform and gather feedback. The evaluation committee kept a very close eye on our work, but Austin and I played by their rules for the most part.

Sometimes you have to play by the rules.

I think the reason we lost UD’s business is because I eventually broke their trust. When they would tell me I had to wait weeks or months for a meeting, I would go around them and get a meeting for later that same week. I didn’t abide by all of their rules and processes because I saw a more efficient way of accomplishing the same tasks, but it did not matter. In the end, winning a customer is actually just winning enough trust from another person or group of people for them to invest in you. I should have played by their rules or communicated better when I intended to break them.

7. A supportive community really makes a difference.

When I first came to Delaware for my freshman year of college, I was a music major. Inside the conservatory were students who had dedicated most of their consciousness on earth to becoming excellent musicians. This endless dedication and passion is something I had been surrounded with my entire life. It sets a high bar for training and performance, and the entire community improves at an accelerated rate because of this culture.

When I left the music school for a year to explore other options, I encountered a ton of cheating, students snorting Adderall the night before an exam, skipping class, being hungover in class, not participating and other blatant displays of apathy and fear. This drastic change in my surroundings helped turn me on to higher education issues and eventually led to ProjectedU.

The beautiful thing about Delaware is how small the state and community are.

However, when I discovered the Horn Program in Entrepreneurship after a year of exploration, I was suddenly a part of that ambitious, dedicated and passionate community I was searching for outside of music. Not only did the program offer money, resources, office space and mentorship, but it introduced me to the broader Delaware startup scene. I was going to multiple networking events a semester, meeting new people, running into people I had already met and building relationships. The beautiful thing about Delaware is how small the state and community are. You just end up running into the same people over and over again, and it is easy to form trusting relationships. Those relationships turned into ProjectedU’s first advisors, partners, clients, users, and friends. In fact, ProjectedU was first created at a community hackathon called Start It Up Delaware at the CoIN Loft in Wilmington, one of the many great tech and startup events in Wilmington every year.

The startup community in Delaware is really something special. Everyone is trying to help each other grow and be the best they can be. Everyone felt like a partner and a friend, and I truly miss the feeling of being an average-sized fish in a very small pond. Here in NYC, it is tough to make a significant name for yourself, and it is even harder to build trusting relationships with strangers. A supportive community makes your startup more influential, your story more viral and your obstacles easier to traverse. Delaware is a great place to start a company for many reasons, but the community and support network are my number one.

Please feel free to reach out to me and discuss further!

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Ben Rapkin

While earning his bachelor’s degree in entrepreneurship and public policy at the University of Delaware, Benjamin Rapkin cofounded three startups in the digital advertising, publishing and market research industries. He currently works as a marketing and demand generation specialist at a software startup called Parse.ly in New York City. Benjamin is also a lifelong musician. He is a New York native, having grown up in Westchester County, but is now a proud resident of Park Slope, Brooklyn.

Profile   /   @BRapkin   /   Send an email

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