Transforming my little startup into a greater learning experience!

Sefunmi Osinaike
18 min readSep 4, 2017

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Waterloo Ontario has a great start up ecosystem. It’s easy to get sucked into the compulsion of trying to solve problems around you. My case wasn’t any different. The influence of those around me went a long way in motivating me to take certain actions.

Majority of students come into the engineering program at the University of Waterloo (UW) as former high rising students back in their high schools. Admission is granted to the 90th percentile performers and is extremely competitive. We all come into university with our egos massaged by our previous teachers. This brings a shock to us all when we receive our first midterm grades and they look nothing like we expect. I wasn’t any different and was quickly heart broken by my poor performance in the majority of my courses right after hell week (a week where engineers have all their midterm exams written).

I tried to investigate what the cause was for myself and my classmates who were eager to get back to being thought of as smart and more importantly didn’t want to fail out. I sat with a few curious friends back at our first-year dorm rooms and we all tried to figure out what was wrong by analyzing ourselves. What we all seemed to agree upon was that we spent too much time on social media and not enough time studying for our courses. We all felt that we used social media the same amount as previous times in high school even though University turned out to be a lot harder than we imagined. This to us meant reducing the time we spent on social media in order to succeed at school.

This was the first hypothesis me and a group of friends had for a problem we realized we all experienced. As a result, we decided the solution would be to create an anti-distraction tool that would prevent students from going on social media at certain times in the day, therefore creating time for learning. Without any validation, we speculated that majority of students felt this way since most of our classmates complained of similar problems. We thought we struck gold by coming up with this idea and if we were accurately able to provide a solution then we would become famous and potentially make a lot of money. As young and determined as we were, we decided to keep this idea to ourselves and work on a solution in secret. We regularly had meetings at our dorm rooms and thought about all the features we would include and how it would be used by students. We often fantasized about the result of our efforts to make such a great product. Brainstorming sessions followed shortly after where we began to imagine what the application would look like and we began drawing low fidelity wireframes. At some point, they looked something like this:

First brainstorming session for Yellow Brick Me in 2014

We called the app Yellow Brick Me themed after the wizard of Oz as a path to lead you back on the right track. We were very excited and bought domain names and began to design our logo. A year passed by and we still had not spoken to any other student that had something to say about the problem. We all feared that if we talked about it, people will steal our idea. We continued to try and develop the idea in secret and as school sometimes got in the way, this slowed down our progress. During internship terms, we felt that we’d have more free time to work on our idea after work hours and so decided to plan for most of the development to be done at that time. Unfortunately, we interned in different cities which made working on development challenging for us. Time went by and still no app had been built, I started to question the motivation behind the team and called for a meeting to see what the future of Yellow Brick Me would be.

At the second semester of 2nd year in the summer of 2014, I took an entrepreneurship class (BET 300) as an elective to learn about solving problems and finding product market fit. I realized that we went about the whole problem wrong. My friends and I already split up from working on the project and I was now alone to try and figure something out for the future of Yellow Brick Me. I also learned that the University would allow students to take an enterprise co-op term to work on an idea they were passionate about. I decided to read into this but missed the application deadline for the fall of 2014. I was still passionate about this problem because I had seen a lot of people suffer from it and I was still battling distractions from my studies. I had also lost a lot of friends who had to leave the program and the university because of their academic performances. I was motivated to ensure that those who come into university would have a guided path on how to do well. That fall term, I strengthened my technical and design skills to try to overcome any hurdle I might face when bringing this idea to life. On this path, a good friend of mine named Joshua helped me as I struggled to piece together an MVP. He was the first person I spoke with besides my previous team, that believed in the idea and would try to work with me to develop this product. My roommate Ian also showed some interest at that time and would later become a crucial member of my team.

Creating a successful product was more than just developing a fancy app. I tried to also make a business model canvas as the entrepreneurship class taught me. That fall I also prepared my first pitch deck for Yellow Brick Me and presented the idea for the Velocity Venture Fund (VVF) qualifiers. Unluckily for me, I stuttered on stage and received all forms of criticism on the idea I had just presented. At this point my confidence had a dent. This was the first time I had spoken to a large group of people about the idea that I had but I didn’t receive the reaction I had expected. It was a real problem, I thought, but I failed to communicate effectively.

I didn’t give up on my start up dreams but took a different approach to the earlier hypothesis of the problem statement I had. Yellow Brick Me was meant to be an anti-distraction tool for students to take back their time and focus on the more important things. I took a step back from this and realized that my friends and I only concluded this after we guessed on what we thought was the true cause behind bad student performances at school. We didn’t validate this by speaking to other students or truly digging deeper at the emotional triggers that cause such actions. In my first semester of 3rd year, the winter of 2015, I went on the path to truly try and understand the problem which started by talking to students and professors. I regularly went to the common areas around campus and randomly spoke to students who would give me the chance. I tried to have regular conversations with them to learn what kind of students they were and how they could stay on track with school. I also went to professor office hours to engage in conversations on what the leading cause for poor student performance was. One professor who was very helpful was the legendary Larry Smith. I met with him several times to discuss the nature of the problem I was looking to solve and he showed great interest and support in the cause. He recommended books and studies to consider which went a long way in building the case for a potential solution. I learned a lot from those I spoke to and I was slowly gaining the confidence I needed to try another attempt at the problem.

As I continued to speak to hundreds of students, I simultaneously tried to test some of the proposed methodologies on how to be successful in a challenging school environment. This led me to determine what could work for the proposed software product I was trying to build. I made enormous progress in my studies and I found that as I was learning about the problem and trying out potential solutions on myself. I saw a 13% increase in my term average; a significant improvement on what I had seen in previous terms. I was the guinea pig of my experiments and felt that if the solutions I tried could help me, then they could help others. I signed up for enterprise co-op for the summer, and this time, I did so very early. This was going to give me ample time to focus on building a software solution that could help battle my problem and that of others as well. I continued speaking to students and as I got to the 500-person mark, I decided to redefine what a proposed solution would look like.

I now understood that students always had the freedom to do whatever they wanted with their time. Spending time on social media isn’t bad. It can sometimes be rather helpful and can act as a stress relief. Blocking it wouldn’t have solved the problem. Instead, a proper way for students to delegate and manage their time would go a long way to ensure they are focusing on the right things at the right time. So, this then defined Pave; a time management tool for students to improve and enhance their productivity. The new name was simple and precise with a promise to simplify productivity.

Before the start of the E co-op term in May of 2015, I then decided to move forward to determine the right number of features needed to accomplish our mission. This is where I now moved from a more flexible conversation with students to a more structured survey to find clues on what the needs of the users might be. This survey was intended to help me narrow the scope of what I wanted to build and provide more validation for the upcoming pitch I was about to present. Every team is required to pitch at the beginning of the term to demonstrate to the school the worth of their idea. This opportunity also provided some selected teams with $5 000 to encourage students to carry on with their venture. While surveying students and practicing my pitch I met Toluwa and Seun who were very interested in the idea. They admitted this was a real problem students faced and wanted to help solve such a problem. Additionally, my friend from high school who just finished his first year of UW, Dike, was looking for a co-op job for the summer. He is a nanotechnology engineering student but agreed to work with me on Pave and I slowly started to build my team.

Day one of enterprise co-op I gave a 5-minute pitch on what Pave was and how me and my newly formed team were a right fit to solve the problem. This time, my pitch was clear and I passed the message of Pave confidently. The judges nodded and understood what I was trying to accomplish. One of them then asked, “How do you plan to make money?”. I responded saying I had the intention to grow the user base before thinking about monetization. Our focus at that moment was getting the product out there and getting users. The judges were skeptical and to my surprise, I was not chosen as one of the winners. Knowing that there would be more downs than ups while initially building a startup, I shrugged off the feeling of disappointment and proceeded to execute the plan I had for that term. The goal was to create a new iOS and Android application for Pave by the end of August of 2015. This would give us the opportunity to release right before new students come into the university. The plan was to put it in the hands of students in first year so they carry it along with them throughout their education to keep them in check. This was our main strategy and initial target group; we finally had something to work towards.

By the end of May, I had successfully spoken to ~ 1000 students across several universities and thus my validation was complete. I knew this was a problem indeed and now understood the proper way to solve it. There were many solutions out there in the market and I played with several apps to get a feel of the market and how we could be truly unique. In addition to hearing what others had to say about those apps, I found that the biggest issue for most people was the motivation to keep using the apps they downloaded for time management. This also followed with the numerous complaints people had of getting over the initial hurdle to add tasks in the app to manage their tasks. I continually went back to students to show them low fidelity prototypes of what we were trying to build and how we were trying to solve some of said problems. The feedback we got was encouraging and pointed us to the right direction. I had never taken a product from an idea to life before and so this process was all new to me. I tried to be disciplined and went to the co-working space the school provided with Dike every day to work at least 9–10 hours a day. I was learning a lot about executing on the software product development life cycles and tried to follow the steps of sprint to get tasks done.

I worked closely on design with Toluwa and Dike to create the visual aspect for the high-fidelity prototypes which I would use to return to students for further validation. This time, I wanted to ensure that every step I took, I was moving in the right direction and thinking of the users every step of the way and not on a personal or team bias of what we thought was right. I would later present the demo video at the start up showcase hosted by the Entrepreneurship Society of UW. After spending the whole day and talking to hundreds of curious students, we now proceeded to iterate to finalize design. I also took some time to consult with UX expert Karin Schmidlin to explain the approach we had and ask for tips on how to improve. I was learning a lot from those I spoke to and was excited that Pave was slowly coming to life. The team and I soon had a very clear visual representation on what Pave would look and feel like. This was encouraging to then proceed to development while making only minor design changes as we moved on and iterated.

The development stage was the most challenging for the team. I had a lot of fun brainstorming flows and design languages for Pave in May. This was one of the most interesting stages for me because we got the chance to be more flexible and try out new things. Speaking to customers to truly understand the problem we were trying to solve was another layer I enjoyed. Moving into June, we were faced with the initial question on the choice of cross platform development vs native development. I thought very hard about this. We were very low on resources, Joshua and Ian would only have time to work on Pave after they got back from their respective jobs every day. They were the more experienced developers on my team with specialties in Android. Dike was new to Software development and I would work with him as we tried to build the iOS app. Cross platform meant everyone would work on the same project and in theory, it might have made development faster since we now had 4 people working on one thing. None of us had ever done cross platform development before, it would have been a steep learning curve for us all. The two choices had their pros and cons. However, I took a step back and did some more research into the decision at hand. We would have to make several tradeoffs with the results of cross platform development. We would have to give off a lot of the experience we wanted to provide for users. To get the intended flow and animations previously designed, we would have to thoroughly optimize our cross-platform development which will require a lot of native knowledge. I convinced the team to go native and stated my reasons. It was a difficult choice, but it gave us more confidence moving forward. I later wrote my work term report at the end of the term on how I went about making the decision to go native.

To kick off development, I broke down all the features we intended to build into user stories and then further into tasks that each person was responsible for. I wanted to follow an agile approach to make sure we built Pave in usable chunks that we could possibly roll out. We had only 3 months to complete the application, that wasn’t enough time if we wanted to do thorough testing to ensure we maintained a high quality of the product. As development goes, some estimates turn out to be falsely projected and expectations had to be constantly reset. This was all part of the package and I learned to get used to things not quite working perfect all the time. I learned how to balance bug fixes vs working on new features that were in our sprints. Our efforts to QA every chunk of the product as they were completed slowed down the pace of the overall development of Pave. This was sometimes tough to deal with and tougher to make some of the decisions to maintain our goal of a successful launch by the beginning of September for orientation week.

While development was going on, I had to ensure that I was building the right relationship with multiple schools to secure partnerships for orientation week. I’d reach out to representatives of UW and other universities across Ontario to speak about Pave having flyers for the students’ package. This was difficult as we had nothing to show yet. The app wasn’t ready and our high-fidelity prototypes weren’t enough to convince some schools. This made the goal tougher as we needed to complete the app to make it easier to secure partnerships. I also had midterm pitches and VVF summer pitches to prepare for, all happening in July. We had no traction yet and only a small chunk of Pave was ready. I had to make another tough decision. I wanted us to release an early version of Pave on both platforms to gather numbers of usage and feedback. I wanted to use these numbers for my pitch to further prove that people could benefit from a product like this. However, the android team was not comfortable with this idea and discouraged me. Pave wasn’t stable enough to be in the hands of users and Ian feared the damage an initial bad first impression would have on the product in the long run. iOS was in a much better state and we proceeded to submit the initial version to the app store. Thankfully it got released:

Initial iOS app store listing for Pave

I also began to create the brand image of what Pave should sound like to potential users, I built the site and proceeded to make a video that would demonstrate the promise of Pave to simplify productivity. Making the script for the video was a team exercise led by Vanessa who helped me with partnerships. This enabled everyone to contribute to the creative process and bring these ideas to life. Toluwa and I then worked on the storyboard and visuals to animate the video and complete the message we were trying to send. The video ended with a goal to urge people to find out more and visit the website. This was then followed by signing up for our mailing list to stay updated with the progress we were making with the app. We measured these metrics to keep track of how the video was performing.

Landing page for Pave to showcase the video we created

The video campaign gave us more numbers I could play with in my pitch to show more interest people had in our product. We received a lot of email sign ups and clicks on to the Pave website. I gave my pitch and emerged as one of the winners on midterm pitches for enterprise co-op award of $5 000 and made it to the VVF finals for the first time after 2 previous attempts. This made the team happy and motivated; things started going in the positive direction for us. Unfortunately Pave lost by 7 votes in the people’s choice category on the VVF finals day along with our chance to secure another $5 000.

After a challenging month of July to improve the brand image of Pave and work on pitches, I decided to focus on finishing off the development of Pave for the rest of the term. Development had slowed down and we were officially behind schedule. We now had the more complex parts of the app to complete and this posed several difficulties in our progress. We tried our best to mitigate some of the issues we had but they proved persistent. I accepted that we would not meet our initial goal of launch in orientation week and decided to look for other strategies to gain usage.

We successfully completed the development of the iOS application in the second week of September of 2015 but had a massive backlog of bugs we had to fix. The android app followed a week later with less bugs. We had all returned to school for the fall semester and were trying hard to work on Pave but our demanding schedules didn’t allow that to happen for too long. We decided to launch the android version of Pave first and work on getting iOS to a stable state. As the fall term went on, I made the difficult decision to park Pave and I no longer worked on the product. After the android release, we didn’t see the growth we would have preferred and I realized my long-term strategy for monetization would prove futile. I was devastated by this and refocused my priorities to other things in life.

Working on pave was one of the more stressful things I’ve had to do in my life. Although I really enjoyed the entire process and it still goes down as my best co-op term. The feeling of creation was euphoric and working with a lot of brilliant people was an icing on the cake. I enjoyed the creative freedom I had and enjoyed all the processes that got me to the finish line. I was sad I couldn’t take Pave to where I felt it could go but I learned a lot during this journey. Knowledge that thrusted me into a great career path and was one of the defining experiences in my career. With over 2 years passed since working on Pave, I still think back and smile through all these moments I lived through. My top key takeaways:

1. If you have an idea you want to pursue, always talk about that idea. This is a means of validating your hypothesis and understanding the problem.

2. No one is going to steal your idea! We’ve all watched the social network and we are paranoid of sharing ideas. Chances are, if you have an idea and started working on it, you should have a better understanding be more ahead of the person who might come steal it.

3. Understand the problem from an emotional level to see what drives people to do what they do. This gives you more tools that you can leverage when using emotional triggers in your product solutions.

4. When you have a new way of solving a problem, you can’t just be marginally better than the competition. You must be substantially better, some say 9 times better to really capture people or make them switch to your product. A much better approach is to truly have a better understanding of the job that needs to be done and deliver a better outcome for the users.

5. Ship as many times as possible. When you work towards a big release it’s sometimes difficult to get everything right and perfection will never be the case. Many small steps are better than bigger launches. Prior to launch, I only shipped once (bad idea!), you learn a lot from shipping, do it as frequent as you can to know how to reposition your product.

6. It takes a lot of discipline to start on an idea and even a lot more to be persistent to keep moving forward. It is never a straight path but with a lot of determination, you can get through the rough patches and do something great.

7. NEVER STOP TALKING TO CUSTOMERS — This is very important at every stage.

8. If you are a for-profit business, always have a plan for monetization from day one. Yes, we have seen a lot of products grow their user base and then start making money but they are very few. It’s easy to look at the success stories and feel attached to their journey. If the goal of your venture is to make money, it’s helpful to start experimenting on pricing strategies very early.

9. Growth is important. Think of ways to do this from day one. Even when circumstances change, always have plan A-Z and further sub plans on how you are going to capture your target market. This is the last stage of product development. The goal of spending so much time and effort to think of an idea and build a solution is to get it in the hands of people to be used. Prepare for this stage as this is when success can truly be measured.

10. Work on something you are passionate about. This should really be the first thing you ask yourself. “Am I passionate about this?”. Time is better spent working on ideas you truly care about or have experienced. You have a better chance of succeeding if you do this.

I would like to thank every member of my team that helped me throughout this journey, both immediate and external. I would never have learned so much if you all weren’t present to walk me through this. A big thank you to Joshua LEO-Irabor, Ian Osawaye, Dike Aduluso, Toluwa Awodiya, Vanessa Krause, Demilade Olagoke, Marcus Osobase, Karo Oki, Seun Makinde, Youssef Medhat, Tobi Ogunleye, Professor Wayne Chang, Larry Smith, Professor Stephen Smith, Mike Kirkup. A special thank you to my mum for all the emotional support through this journey.

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Sefunmi Osinaike

Human 💡| Promoter of peace, entrepreneurship and technology!