Article: 10 — My First experience with Entrepreneurship and The Wrong Way To Do it In College

preface: Given the nature of this series, spanning the last 11 years of my life (chronologically), I will be writing each story in first-person as if I was writing at that age.

ages: 18–20

My First experience with Entrepreneurship and The Wrong Way To Do it In College

The Setting

It was freshman year second semester, the weather was warm, the students at the Kelley School of Business were slinging around the word “entrepreneurship,” and creativity was in the air. I befriended a buddy from New Jersey, Brandon K, or just BK. What a crazy coincidence meeting him. After a few conversations we realized we had a past together. Back in 8th grade there was a rumor he liked my girlfriend and was trying to undermine me, but thankfully it was just a rumor.

We spent a lot of time together and were always brainstorming about random entrepreneurial endeavors. We even thought we could eventually present one of our ideas to Mark Cuban, a successful alumnus of our school. Nevertheless, it wasn’t really going anywhere, so we let it slide. But Brandon definitely left a good mark on me and I am happy we are still friends to this day.

Thoughts Brewing

My entrepreneurial mindset continued and really sparked in the second semester freshman year business class with Professor Loucks. She was tough on me, but I knew it was because she believed in me. Towards the end we were challenged to come up with a “final sales pitch” presentation, showcasing skills we had acquired throughout the year. I was talking it over with my roommate, Tyler, (ironically, “Big T”, deeming me, “Little T”), was obsessed with working out… I mean literally OBSESSED, but I was pretty much in the same boat. We worked out together all the time, but there were times our schedules simply did not match up. During those times I would message Brandon and sometimes we worked out together instead.

First Ideas and Quick Pivots (already)

But, it was when they BOTH were not free when it hit me, and “Workout with Me” was born. This was the idea I selected for my final sales pitch, my million dollar idea. I told my roommate, and he quickly shot it down. However, he did offer some good constructive feedback, in that the app would be slightly weirdly connoted, as in, people don’t just “meet up and workout.”

A week later my sister and mother were visiting for an awards ceremony. It’s not a big deal, but it was a good excuse for them to come visit. We were walking to Hartzel’s (an ice cream shop) and I was telling them the story thus far. I suddenly stopped in my tracks when it hit me, as I quickly arrived at my first pivot: “Exercise with me” was born. I convinced myself that “Workout” had this aggressive, overly masculine, and potentially misogynistic connotation as an app, but “Exercise” was so much more open, inclusive, and just made more sense.

Phase 1 — Getting Started

So I had this idea, great. No really, outside of my computer science classes, looking back now after my entire education, I don’t remember ever being so excited for a class project in my entire life. I needed a decent grade to finish the class with an A, but this was slowly becoming more than just a class project. I was spending all of my free time researching, preparing slides, iterating on ideas, coming up with long-term plans, etc.

I got to a point in which the presentation was done and I was ready to really get the ball rolling — I saved the powerpoint that you can view here. I had one close friend in computer science, whom we all recognized as one of the smartest in the group: we will call him “NN”. I told him I had an idea, I felt really good about, and I wanted to build an app to accomplish it. He said he’d entertain the idea, but I told him I needed him to sign an NDA first, because this is how I was groomed in the business world. He was really against this, and for good reasons (I later came to understand when people would ask me to do the same).

Silicon Valley

At this point, I had already taken my 3rd and final pivot and expanded to “All Events.” I came to this one day when I was walking to an event and got 2 notifications on my one for 2 other events scheduled on 2 other different platforms. I was so annoyed at the lack of proper planning and due diligence of these different platforms and organizations, because it precluded me from the ability of attending all these events.

He signed the NDA. I was still so scared to tell him, because I truly believed in my idea, and I thought an entrepreneur is supposed to keep the idea a secret, right? That’s the only plausible way to prevent anyone from stealing your idea, or so I thought…

He liked this final idea. It was 3 am and we were watching Silicon Valley. I crashed at his place and just before we fell asleep, I told him the idea. He said he’d sleep on it and let me know in the morning. That show lived in infamy with me as it became a real-life narrative of what was about to happen.

The Beginning

It was good. There were a few weeks left in the school year, so I continued my business research, and he started his technical planning. He slowly came to software decisions, which was nice, I guess, since I didn’t understand any of it at all. I had no technical background. We set our objectives officially but informally, I would “handle the business side,” and for him, the technical side. It was pretty simple.

We had a friend who was business savvy and super interested in our idea, even if he would work free, he just wanted experience. So, he too signed the NDA, and we “brought him in.” This was my suitemate, Joey. I liked Joey, a very honest and simple guy. We didn’t really know where he would fit in, so we figured we’d let him do a blend, but he claimed he could learn the technical side, so we put him to the test. NN had provided him with some learning modules and told him to come back when he completed them.

The Grand Naming

When NN and I would sit and work together, it felt so exciting and invigorating. We were working on a startup, though extremely early on. The semester was coming to a close, and we realized we needed a name. So we picked a day, and agreed by the end of it we’d emerge with one, no matter how many hours it would take. I don’t know why, but we were thinking latin, given the allure and wealth of possibilities. Something about the language lent itself as a good app name.

We found a website with a list of 1000 latin words, and both picked our top 5. Ironically, there was one we both chose, and that name was Vigeo.

Still to this day I am surprised something liked that happened. I remember it like it was yesterday when I got to that name, naturally it was near the end as the list was sorted alphabetically, so at that point I’d already have seen some 900+ words.

We didn’t know why, but it just felt right. We later realized it stood for “thrive and flourish and when people come together” — which was exactly the purpose of the app, and later became the app slogan. We now had a name and a purpose, and all went home for the summer.

Phase 2, The first summer — making progress

I set up a google drive, as I would be producing a ton of documents. His equivalent was GitHub (whatever that meant). In a month’s time I had come up with a phased marketing plan, stock plan, accounting book-keeping records, a bunch of legal documentation, general business and executive documentation, a funding plan, pitch decks, etc. Looking back, I really produced a decent amount of content.

I need to give a special shoutout to a family friend of mine and my soccer coach throughout high school. Together the two of them helped me navigate the extremely complex and convoluted accounting and incorporation processes imposed on us by the US government. If it wasn’t for them, I definitely would have made some legal mistakes and not have been able to successfully start a company.

NN coded. He would research and code, code and research. He did some planning and would tell me the technology decisions he made and started sketching the UI. Neither of us were designers, and that became apparent pretty quickly.

A Day in the Life

For seven days a week, the entire summer, I would wake up at 5:30 AM and go to the caddy yard. I’d wait for a few hours and do my summer homework, sometimes even while walking the golf course, caddy for a few hours, then return home. I’d hit the gym, and or go for a run if I had the energy. I’d come home and finish my summer homework. I was not in summer school because I was behind, I was actually trying to get ahead, so I could take fewer classes back at school, and focus more full-time on the app. So I took three summer classes. After my homework was finished, I got right to working on the app which included soliciting funding and learning to code. I’d cook my own dinner, work on the app, pass out by 12, and do it all again. It was a long and tough summer for sure, a summer I will never forget.

The Power of Github and the definition of Insanity

So at this point, my knowledge of coding went quickly from nonexistent to novice. I had just recently heard of GitHub, so that was pretty exciting because it was no longer a myth! I was following a tutorial on database migrations, as we wanted to explore moving from a postgres instance to the Microsoft Entity Framework on asp.net, where I setup a RESTful application that mirrored the flask application I worked on previously. I spent 12 hours working on this, trial and error, starting over, I had no idea what I was doing, to be completely honest.

That day I started at 6 pm after caddying, and literally finished at 6 am. I thought I might as well commit it to GitHub, why not… What I didn’t know at the time was that my repo was on my desktop, I realized this after the fact, reverted the change, reset — hard, uncommitted my project, pushed with that bloody -f ( — force) command and before I knew it I lost the project. I can’t remember exactly, but somehow I also lost some stuff along the way on my desktop. In either case, it wasn’t a good situation. I sat back in my chair and stared at the computer for 5 minutes, trying to mentally process what I just did.

After around 12 hours, finishing the project, and deleting the entire project, I decided I needed a break. I went to my favorite breakfast place which is only open 6–9 am and brought my dad breakfast as a surprise, where he obviously questioned why I was up so early. I replied, “don’t ask…”

I finished my breakfast, and started again on and off from 6 PM until 6 AM the next day, when I finally finished again. It was like deja vu, I literally could not believe it. I didn’t sleep for over 2.5 days, but I eventually finished it.

The Power of Mentorship

That took care of the backend, so let’s talk about the front-end. Our app had to be cross-platform, and Xamarin at this time was the best option. Xamarin was a newer technology at the time and not well documented (IMO). There weren’t a lot of tutorials, so you kind of just had to figure it out and do a lot of trial and error (my favorite)! It was a tough choice to make, and came with a steep learning curve.

Then I came along this one fellow, Adrian, who had a blog tutorial I followed that really helped me get going. Naturally, I got stuck at one point so I sent him an email, begging to take my call. I had very low faith in reaching out, I thought I was alone. A few days later he replied, and low and behold, we were on the phone shortly after that. We spent a lot of time chatting over the next few weeks, and he really helped me learn a lot. What a remarkable man, taking the time out of his busy day to help a random kid across the country. Fast forward a few years, he is now a great friend and mentor to this day!

Phase 3 — Seeking Investments

As I was caddying, balancing saving money for school and putting it towards Vigeo, I tried pitching my idea to the golfers, which was the best avenue I had to solicit for seed investors. It was humbling, trying to get rich golfers to listen to a young golf caddy with a dream. Nevertheless, I made some great contacts along the way.

• There was Jason, who worked at a tech company in NY. He was super friendly and wanted to be a mentor to me. He brought me to NY and took me out on the town. I put on a suit, packed my suitcase, and took a bus to NY. I practiced my pitch the entire bus ride. At the end of a night of drinking, he said “Tyler, I like you kid, but I can’t invest right now, you just have an idea.” It was a shame, as I had higher hopes for my first investment attempt, but I didn’t let it get me down.
• There was Paull from Instagram, yes two L’s was key. I caddied for a man named Will Mullin and told him my idea. He said he wasn’t really in the tech or startup space, but had a friend, Paull, who might take a listen. Paull worked for Instagram in strategic partnerships, which I thought was perfect for Vigeo. I followed the same process, but changed the approach a little. I went business casual, took a bus to NY again, and showed up at the Facebook Headquarters in NY. This was really cool. Long story short, it ended the same. But once again, I left with great feedback and learnings, which is really what I needed at this stage.
• Next was Bob… Good old Bob. I caddied for Bob, who was retired and lived on a golf course. I decided to wait till about the 15th hole to tell him, instead of what I usually did, which was tell the golfers right away, before establishing rapport. Not only did I wait to butter up Bob, I made sure he had the best experience at my golf course as a visitor. Bob had one of his best rounds of golf in recent years, thanks to my expertise on the course. I told him what club to use, how far to hit it, and where to putt it — I truly couldn’t be wrong that day if I tried. When I eventually told him the idea, he was immediately interested, but as a much older man than the first two, his approach was very different. Bob was interested in me and my team, and our passion, and less about the idea itself. He brought in his partner, David, who was a stud NY Banker with a lot of connections and experience. Together they taught me a lot and mentored me. They challenged me to produce documentation (that I alluded to earlier), revise it, make it succinct, improve it, iterate, etc. The final products were very professional and I was proud. These conversations spanned a few weeks and a few fancy dinners. In the end, they made an offer. Now, after watching too much SharkTank, and Silicon Valley, the numbers meant a lot more to me than they should have. We kind of played around with the numbers on the investments and the percentages and kept going back and forth like a game. They did make an offer, so it was rewarding in the end, but my partner was against the numbers, and said we’d get future offers… and he was right.
• There was one kid who I was close with at school, Chris P, with a long Italian last name. Chris was a dreamer, a phenomenal listener and loyal friend. Many late nights I would stay up working on the App and he would join me, to keep me company, and let me bounce ideas off him. He knew about the idea from earlier on as I trusted him. I told him that we were looking for an investor. One thing led to the next, and said his father wanted to call me to learn more. I had no idea what would come from this, but I figured it wouldn’t cause any harm.

My First Investment

When he finally called, I told him I had a 20 page business plan and a 1 page executive summary, but that I would only send over the summary… If it wasn’t enough, he probably wasn’t going to invest, as were the results of my previous attempts. We spoke for a few minutes, he was interested, and said send me the one pager and then we’d be in touch.

A few weeks later, I had left for Indiana University to volunteer at Camp Kelley the week before school started. I was a camp counselor and helped mentor incoming freshmen to help transition into college. It was late at night and just after I had sent all the campers to bed I received a call from Mr. P. I ran outside and held my breath, until I heard those magic words: “We are going to invest.”

This was honestly one of my single biggest accomplishments to date. With a piece of paper, an idea, and a dream, I convinced a group of small investors to purchase 10% of a company that didn’t even exist yet, but one that I surely was going to make it so.

Back to School

Camp came to an end and I was eager to meet up with the boys to see the progress they made on the coding side after the first summer of work. Not only was I eager to see the progress, I also was excited to show the coding skills I acquired over the summer and put them to work more regularly.

I immediately started drafting up all the official stock plan paperwork over the next few weeks and incorporated the company. Once again, Dan was a huge help and I am super grateful to have him in my life to this day. We planned our first meet up after everyone moved in and we were met with a rude awakening — NN faced technical difficulties and was not as far along as expected.

He was able to get the basics done … On my end I was proud because I put forth a great deal of time in that summer, while also managing school and caddying.

Work Work Work

A few weeks later NN and I finally got in the groove of things. We were finally making some progress and seeing deliverables getting completed and features coming to fruition. I was happy — more lines of code were being written, the repository was growing, and we were getting better at development. Personally, I was taking on more tasks and learning along the way, and really contributing autonomously by the end of the second month back.

Awareness

Since we were making such progress, we wanted to slowly start telling people to “ready them” and “build anticipation.” Although, we did this very very slowly because obviously we didn’t want people stealing our million dollar idea… could never forget that!

All of our friends naturally started catching on as they saw NN and I working together often and at weird hours. They knew we didn’t have any overlapping classes so they became suspicious. I would give people hints, as I did not fear telling them the basics. For example, I told them that I was working on a mobile app, which made me feel pretty cool.

Outreach

In my “spare time” I came up with a marketing plan. I reached out to hundreds of different organizations that hosted events and explained to them the opportunity of partnerships. They were all intrigued, as mobile apps were still up and coming at this time. In addition, student organizations always have trouble with attendance and participation, so they were eager to have some type of social media tool to help them better reach their members.

The App Store

We finally got onto the app store… It took a few months to get this accomplishment, but we finally got onto the app store… There were a few failed attempts, because Apple had very strict guidelines. The boys all celebrated and popped champagne! What great feeling it was. In just a few short but tough months, we were able to receive an initial investment, build a first-version cross-platform mobile application, and get it onto both app stores.

The failed Theta Thursday and Grilled Cheese

It was time to pick up the speed with getting awareness and getting some downloads. We wanted to do a soft launch and I had the perfect plan. I worked part-time (also in my “free time”) in order to afford meals as I did not have a meal plan. I had a meal-job at Sorority called “Theta” (Kappa Alpha Theta), which was filled with a bunch of nice and friendly girls. I told them about the app and they were all super supportive. Every Thursday they had “Theta Thursday,” which was grilled cheese and cookies for lunch. However, once a semester they would have their philanthropy where they sell hundreds of GC and cookies.

Since I worked there they agreed that if I arrived early and helped set up (and make 200 grilled cheese sandwiches and 300 cookies), I could take the rest of the night off and speak to people in line to tell them about the idea. This was a really interesting and eye-opening experience for me. I walked up to people in line and just tried to explain to them about the app. Halfway through the event one of the MCs agreed to make an announcement about the app and ask people to download it. She had a nasally voice and actually completely mispronounced the name of the app. I talked to about 50 people that night and maybe got 5 downloads if I was lucky. I knew everything about the app and the problem very intimately, but didnt know how to market it.

Everyone liked the idea, and wanted to see the final product, so when they saw the bare minimum I had to offer, they lost interest very quickly. The backend was slow, there was leftover dummy data we forgot to remove from the sample data, it was poorly formatted, and looked very much like a rough draft. I was ashamed and felt devastated.

Big Decisions

In the midst of class, work, and working on the app, I still needed to play it safe. So I decided to apply to a few internships for the summer and actually got quite a few interviews at some good companies. The interviews were pretty easy, I just told them about the app and everything I had done and was planning to do. A few of them even asked me, “if you’re going to build this app, why do you want to work for us?”

A few weeks went by and I actually got a few internship offers which was really exciting. I told NN and he told me that working for a corporation would not teach me nearly as much as I could learn if I just stayed the summer and worked with him on the app. I told myself just like I already was, that I could intern during the day and code at night… I was already used to being productive for 18 hours a day, while sleeping 6 hours a night for 2 years already. In the end, I think he was right.

But in order to turn it down, along with the amazing summer salary that would have helped me pay for school (which I really needed), I at least needed some alternative to justify my decision. Fortunately, there was a new summer program on the horizon at my school.

Travis Brown was the Dean of Entrepreneurship at the School of Informatics, who I had already connected with to discuss major startup competitions. He said we weren’t ready for those and he was right, which is why they created an incubator program to help emerging startups come together to collaborate and help them in their early stages. The timing was perfect, so I thought. I immediately applied but wasn’t going to be notified until the second semester, which was after the deadline for the internship. I went with my gut, and turned down the internship.

Second Semester — Sophomore year

We both locked down over the winter and set some good momentum for the second semester. We got to a point where we could really start visualizing progress. I became Project Manager and set plans, iterations, features, etc. This really helped to keep us on track and working on the right things. In addition, we actually found some cool UI/UX kits so we could start visualizing what our app was meant to do, which share local events catered to people’s interests, at the core.

Second Summer

We eventually were accepted into the summer incubator program officially called the BEST Aspiring Entrepreneur program. This granted my team mentorship from Travis and some of his colleagues and a small stipend to use for food and housing, and whatever other expenses we had. This was great and truly characteristic of Travis’s amazing commitment to students and their growth; he sparked numerous initiatives over the years to achieve this goal.

I told my family I would accept the program and be staying in Bloomington in the summer to participate. There was only one problem … I had nowhere to stay. Summer was a few weeks away and I needed to find temporary housing that was relatively close to the campus where my team was allotted a small office to work in.

Rachel Ray

No, not the famous chef, but that would have been cool… in fact I would have switched careers right then and there! Anyway, Rachel is an awesome friend of mine that I met on Halloween freshman year. We became great friends and stayed in touch ever since. We always had each other’s backs and supported each other when we were down.

Rachel had a 3-bedroom with 2 roommates who would be gone for the summer. She herself would also be gone half the summer… so I had a thought; I proposed the idea of me living in the apartment in the summer if I covered utilities. She had no reason not to agree, so I moved over with a garbage bag full of clothes.

My Summer Routine

I would wake up naturally to the sunlight around 8–830 am, do my morning yoga and core workout, then make and eat breakfast and pack my lunch. My meals consisted of eggs and tortillas with salsa, and rice, chicken, beans and salsa for lunch as well as for dinner. I would eat about 3–6 eggs a day and 1–2 pounds of chicken a day depending on how much I exercised and how long I was up for working. I got really good at cooking the same things over and over, so that’s a plus. Also that salsa was amazing… It was homemade from one of the girl’s from the apartment’s grandmother’s recipe. She was gone for the summer and there were hundreds of jars in the cabinet so that kept me busy.

Once I finished breakfast I would make a plan for the day with regard to what work I would accomplish — keep in mind I was also taking 3 more summer classes on top of working on Vigeo, just like the year before. I would do some homework for 30 minutes or so for one of the 3 classes, then pack my bag and head off to the office. It was a hot summer, so everyday I wore a tank top and my Teva sandals that I traveled the world in.

Once I arrived at the office I’d plug in my monitors and chargers and plan to stay there for the next 10–14 hours depending on the day. I would code, do push ups and situps, do classwork, plan, take phone calls, etc. I had a playlist that I grew to over 1000 songs and was able to go through the entire playlist in a week because of how much time I spent coding, literally.

Occasionally I would go back home for dinner if it was a productive day or if i needed a break, other days I would just eat in the office or on the porch of the building and enjoy the view of people playing pick up soccer and sometimes even quidditch across the street in the IU Woodland parks.

A Lonely Summer

As you can tell from the above, it was a lonely yet humbling summer. I definitely spent the majority of it alone, and only when I was working with others in my summer program cohort did I really have the opportunity to interact with people.

Rachel also had a cat that I took care of and hung out with. I would feed and clean up after it. What a cute fellow that was psychologically good for me. I didn’t have many friends at all that stayed in Bloomington that summer. The few that I knew were all in classes and hung out in their cliques, or were 21 and could go to the bars, which I was not.

The Beard and the Quintessential Developer

No… not like James Harden… Because I was mostly alone and definitely didn’t have anyone to impress, I decided it would be cool to see how much I could grow out my bear and hair for the summer. It made me feel like a “Quintessential developer” that I aspired to be like one day. There is not much more relevance here on this, but I figured this was not atypical to a typical startup story.

Our New Hires

Going into the summer program we know we needed help on all fronts, on the business side and the developmental side. NN had suggested we bring in his friend Otto who would be there for the summer and really liked outreach-related work. We figured we had nothing to lose and it did increase our chances of getting accepted into the summer program as we had more dedicated teammates.

First Hiring: Otto

What an interesting guy with such an interesting backstory. Otto grew up in Utah and transferred to Indiana University halfway through his collegiate career. He had a ton of experience with social work, outreach, local governments, and many other related areas of municipality functions. He loved the idea and had such a powerful presence about him. As I became more strictly a developer, he became our lead presenter and marketer. He helped us a ton with the planning efforts and getting connected with various groups and businesses around Bloomington. He even lent me the bike I used all that summer to get around town. At the end of the day he became a great brother of mine and still is to this day.

Pizza, Love, and Startups

Rachel came back for the summer, so I relinquished the room to her and moved to the couch where I would remain for the next 2 months of the summer — now we’re talking startup culture; every real startup starts with someone bumming a place to stay in a garage or on a couch… That is the story behind AirBnB and it worked for them, so I figured I was doing something right… This is what I had to tell myself at least.

Rachel also became lonely quickly as she and I were in a similar boat. I did what I could to help her out as a friend and to pay her back for letting me stay at her place. Rachel wanted a job, which is why the fact that they called me the “godfather” came in handy. I made a few calls and within a week got her a job as a server at a local pizzeria that she would go on to keep for 2 years after that.

Otto would often come by when I was at the office or working from home on the weekends to hang out… It’s not that weekends were any different from weekdays as my daily routine spanned all 7 days all summer; however, I used this to help myself psychologically so as to maintain a notion of “time,” which quickly lost meaning.

However, a few times I noticed Otto would be waiting for me to return from work to be hanging out with Rachel on the couch watching tv. It didn’t affect me at all as I was so wired in to my work, and not until a few weeks later did they sit me down to tell me they had started dating. They were nervous about telling me and worried it would complicate things, but I was so happy for both of them and thought it was kinda cool I had set them up!

Second Hiring and CPTs

I printed out some flyers and put them around the tech school. One Masters student reached out to me who had tons of experience in industry. He was a bit older than us and had a friend with a similar background. We even offered to pay them stipends that came from the pool of investment funds and the money we got from the program.

NN took the lead on training them, getting them setup with the dev environments, etc. He tried, but there were technical difficulties in getting them onboarded and explaining to them the vision of the app. A few weeks went by and there was very little traction they made together. We eventually let them go after spending weeks of hiring them because of the legal obstacles we faced hiring international students. This was called CPT, which stood for “Curricular Practical Training.” This how international students who were here on educational visas were able to participate in “extra-curricular” activities that were run by “for-profit businesses.” I had to file a bunch of paper-work, meet with the legal counselor of the school, and go in with them for a screening to prove we were a legitimate business and to sign off on a curriculum that we would complete as a result of participating in a CPT with Vigeo… In the end it was a waste of time and effort — the little code they wrote I could have done on my own and not have had to train them. Once again, a lesson learned… If you want something done right, you have to do it yourself.

Summer in the Entrepreneurial Program

So yeah, in the actual program itself we were big shots. There were a few other teams, and we all were pursuing a technical solution to various problems. We also greatly varied in the complexity of the solutions themselves — one team was trying to provide a delivery service, another team was building a simple web application for pick up sports, and then over course we were building a cross-platform mobile application with a bunch of complex features.

KISS — Keep it Simple Silly

On the technical side, we didn’t really take the advice we were given, which was so simple: deliver our core feature of event aggregation and curation. We had 10 features planned and only 2–3 down, including event aggregation, thanks to me. A few months earlier I took on the challenge of learning what an “API” was when I had to write one for our backend server. Once that was completed, I learned there were many public facing APIs out there that we could use. I searched for days and had to even apply for some for our app to use. I got a response from one and went back and forth with their 3rd-party team until we were approved; this granted access to an API that allowed us to give users a beautiful selection of events going on around in them across various categories. Now-a-days, you use the Facebook events platform… our platform pre-dated that public release and would have been pretty damn cool to use as a predecessor.

It’s a shame because our first feature, our core feature, is the one everyone really wanted. Travis and everyone in the program had begged us to just put that out and get it tested. It was very complicated to explain that we were overcommitted with our other features and couldn’t produce a standalone application that was sufficiently functional with only the core feature. What this really means is we did not do a great job of planning the different iterations. We kept delaying launching because we wanted everything to be right.

Apple (TLS) Security updates — When Sh*t hit the fan

A few weeks later we made some more progress. We finished some features and figured out how to remove/undock some features that were blocking the launch. The specific software we were using was Xamarin, a cross-platform mobile software IDE. It was because of this, that Apple refused to help us debug our crash logs, even though we had it in the app store. We have produced a few incremental builds in the beginning, but then the next build had around 6 months of code in it that had not been verified by the app store.

When we tried to submit this newest version, we received numerous symbolized crash logs from Apple. I imagine years later they have gotten better, but man this experience was hell. I would receive anywhere from 5–7 crash dumps that were all symbols, I then had to manually link each one with their symbols, and thousand line stack traces. I made the call that we needed to pinpoint each bug and get back to a good state before that bug — something we should have done from the beginning.

Eventually we effectively had scaled back 5 months of work, upwards of 2000 lines of code, because we discovered that the authentication feature was broken, which needless to say existed extremely early in the app boot and user experience sequences. Week after week for 1.5 months we were just debugging and flighting, trying to find a needle in a haystack. In the end we reasoned that there were one or two edge cases in a giant application that didn’t always reproduce, however, Apple was able to do so, they just could reject our application and not tell us how. We never really recovered from this.

When reality sets in

Fast forward a few more weeks and It was already junior year: a little under 2 years into the project. Now, just like always, I was prepared for another busy semester, but this one would be different. I was taking 18 credits spanning 2 majors and I was still debugging and refactoring code, by myself, as my partner and I went separate ways. The investors wanted to cash out, so I returned all that I had left.

Looking back on An Experience of a Lifetime

Working on Vigeo was was tough in so many ways. It was mentally challenging working on a complicated application, physically tough working so many hours along with many other commitments, and psychologically tough overcoming mental hurdles and challenges I faced. It was definitely diminishing and even depressing at times, but I always pushed on.

When all things were said and done I had lost about $9000, which was quite a lot to a college student, a few hundred hours of sleep, an internship on my resume with an top 100 company, a dream, and the interest in entrepreneurship. I had the idea of trying again and could never get over it, but a few months later I took a step back to think about the entire situation, and realized I made out alright in the end. It took me a while to get this story written, as I hope you could imagine why, but this is what I needed to do in order to really have closure with my longest and most challenging journey to date.

Lessons Learned

Not for nothing, but I learned a hell of a lot. Here are just a few of those lessons:

Go with your gut:

• I knew Otto as a great partner and that we would remain friends for years to come
• I knew we had one core feature that is all we needed to get user adoption
• I knew I would eventually learn to code and love it
• I learned feedback from the actual users is more important than my own opinions

Working with others:

• If you are onboarding new people, you have to invest ample time in training to ensure that your team succeeds
• You don’t have to love who you work with, you just have to be able to work with them

Planning is one of the most underrated skills in project management and what could make or break a project

Mentorship is something to never take for granted

Trust: trust and accountability are among the most important traits needed in a startup.

Entrepreneurship is tough: it’s definitely not made for everyone, and takes a special kind of person, which I would like to think I am and why I hope to have the chance again some day

Acceptance: i learned that if I could accept my greatest enemy and defeat, I could live a happier life without hate

In the End

In the end, I believe that if it wasn’t for all the hard times I put up with I wouldn’t be where I am today.

• I ended up switching in to computer science and falling in love with the field
• I ended up with a story that changed my life
• I went on to get a job at Microsoft

To conclude, I’ll quote the famous entrepreneur Paul Graham, who I studied during this endeavor: Don’t start a startup in school.

Thank you for the read, I hope you enjoyed learning about more startup journey and hope to write about a future one!