What we learned from failing as first-time founders straight out of college

Successes, failures, and lessons learned from taking the leap.

Written by Dilip Rajan

Over 90% of startups fail. We always hear about the successes but we don’t hear enough about the failures. Unlike most of our peers who went into finance and consulting, my co-founder and I started a startup straight out of college. After working on it full-time for 9 months, we’re now calling it quits. The following is our story and what we learned from our experience.


Taylor and I met during undergrad at Penn, where we both studied business. After Taylor developed the initial idea for Vyrtex for a class project, we started working on it together during our senior year. Our mission was connecting millennials with smart, thought-provoking articles. In a world where millennials primarily get their news from social media — populated with listicles, clickbait, and other low quality content — we wanted to cut through the noise and create a space for quality content to thrive.

May 2015 — graduated and ready to hustle.

We started by creating a website where anyone can sign-up and share curated collections of the best articles they’re reading, organized by topic — like Pinterest for articles. We also send a daily email newsletter with the best articles on tech, politics, and culture, curated by us and other Vyrtex users.

As graduation approached last May, we decided to forego recruiting and work on our startup full-time. After nine months of sweat, blood, and tears, we’ve made the decision to stop working on Vyrtex full-time. The site isn’t shutting down and the daily emails will continue, but Vyrtex is becoming a side-project for us as we pursue other full-time endeavors.

Our experiences taught us a tremendous amount both about ourselves and what it takes to start a startup. Here are the pitfalls we encountered and the lessons everyone can take away:

Lesson 1: Team

Big takeaway: if you’re building a tech product, have a technical co-founder.

When we started Vyrtex, we had business and design skills — what we lacked was technical experience. I was a computer science minor with several hackathons under my belt but after I built the first version of our site, Taylor and I decided that we wanted someone with more experience to continue developing the product. We were faced with 3 options:

  1. Find someone to join the founding team as a technical co-founder
  2. Have me attempt to get my technical skills up to speed
  3. Use freelancers to build the product until we accumulated the necessary traction to fundraise and hire technical talent

We briefly went with option 1, but after a few weeks of searching, we were unable to find anyone to join the team and switched to option 3. This was a fatal mistake.

We knew that outsourcing our product wasn’t a good idea. But Taylor and I initially thought that we could get by — at least until we could build significant traction — because we weren’t freelancing the traditional way. Instead of hiring a development firm and completely outsourcing the product to them, we took a much more hands-on approach: Taylor and I designed product features together, I created detailed mockups, and we found talented college freelancers who would implement the features cheaply. But as time went on, the cracks in our plan began to show. Speed was crucial — we needed to constantly iterate on existing ideas and test new ones to see what would stick with our users. And due to a lack of aligned interests and accountability with deadlines, freelancers slowed us down considerably.

Months passed and we began to realize that we needed a technical co-founder. We tried to bring on one of our freelancers to the team — we skyped him several times, talked to several references who had previously worked with him, and even had him agree to move to Philly as soon as possible so he could work with us in person. After several weeks of ensuring that he would be a good fit, we extended him an offer to join the team. Within a week of working with us, he ghosted us.

With nowhere else to turn, we tried option 2 out of necessity. I dove into the existing code, tried building new features, and reached out to experienced friends for help whenever I hit a wall. After a few weeks of getting up to speed, I was at a point where I could confidently handle most of the technical work. But by this time it was too late — the consequences of going months without a technical co-founder had taken their toll.

Make sure your team is complete before tackling your startup’s other major challenges. This means that if you’re building a tech product, you absolutely need to have technical skills on your founding team, whether you bring on someone else or you build-up the skills yourself. The more you try to push ahead without resolving your incomplete team first, the more you accumulate problems that hurt your pursuit of product-market fit.

Lesson 2: Product-Market Fit

Big takeaway: early on, maintain a “testing” mindset and find your product-market fit.

When we started building Vyrtex, we had read The Lean Startup and all of the startup wisdom around the importance of validating your assumptions about the user and market. We started-off by following this wisdom closely — testing our initial assumptions with surveys, a minimum viable product, and extensive user feedback. For every new feature we wanted to add to the product, we made a hypothesis of how it would affect our key metrics and laid out a plan to measure the results.

We often stuck to the story that we wanted to tell, instead of listening to the story that was unfolding.

But as time went on, we became increasingly biased by our initial hypotheses. We often stuck to the story that we wanted to tell, instead of listening to the story that was unfolding. We sought out and listened to the feedback of the one user who loved a feature instead of the fifteen other core users who didn’t. One primary example of this was our focus on web rather than mobile. We weren’t completely ignorant. We knew the industry trends, and many users even told us that we needed to build a mobile app since people increasingly read articles on their phone (during their commute, while waiting in line, or on the toilet). But because of confirmation bias, we paid more attention to anecdotal cases of users who preferred reading longer articles on their laptops. Perhaps we could have reduced our bias by having a larger sample size to run tests on. In hindsight, we should had been more aggressive about pushing Vyrtex to audiences beyond the low-hanging fruit that we had reached through our friends at Penn.

Our lack of a technical co-founder also hurt us here by preventing us from failing fast and iterating on our product properly. While we had plenty of ideas we wanted to test, our reliance on freelancers meant that it took too long to build and test them. By the time we released a new feature, we had grown impatient and would completely switch our approach, without first gathering quantitative feedback and making tweaks. We ignored or changed our key metrics frequently and this led us in circles instead of progressing incrementally.

Nothing matters more for an early stage startup then figuring out product market fit. Forgetting this was a crucial mistake. You need to build something that your users actually need and that solves their problems 10 times better than any existing solution — this requires a rigorous focus on testing every assumption about your users and market. Never lose sight of this.

Lesson 3: Systems

Big takeaway: even early-stage startups need formal systems in place to maintain communication and accountability.

Taylor and I were great friends when we began working on Vyrtex. We were able to discuss our thoughts and feelings without hesitation and we took our constant communication for granted. But as we spent more time working together, our natural tendencies kicked-in and we had no system in place to account for them.

Taylor is naturally more silent and independent and he often avoided direct confrontation about issues. I was hesitant to force this confrontation in an effort to avoid seeming overbearing or irritating.

Taylor needs work-life balance and a sense of personal space to stay energized and motivated — he enjoyed working hard on Vyrtex during the day but preferred keeping Vyrtex-related discussion to a minimum after returning to our apartment. I was more intense and preferred to talk about Vyrtex around the clock, which only caused Taylor to close-up and become more silent.

We never explicitly addressed our preferences adequately and they contributed to our decreasing lack of communication over time. We were less able to have candid conversations about Vyrtex on a daily basis. We both started off as leaders but increasingly became followers, each relying on the other to push things forward without proper communication.

Eventually, we realized what was going on and we put systems in place like a daily scrum and discussion of our “feelings” — this improved communication and accountability, but it was too little, too late.

Through this process, we learned that it’s not just big companies that need formal systems of communication and accountability. Even if you feel like your team gets along well through informal communication, take the time to establish more formal habits. That way, when things inevitably start crumbling, you’ll have a system in place to talk through the problems that arise.

Communication is 🔑

The Importance of Having a Mentor

We were bound to make a lot of these mistakes as first-time founders. Starting a startup is a uniquely stressful and challenging experience. That’s why we could have benefitted immensely from a close mentor who could have steered us away from some of our larger pitfalls.

We were fortunate to have a number of people we were able to reach out to for advice. However, the type of mentor that would have been most beneficial to us should have met the following 3 requirements:

  1. Pertinent experience with building a successful startup
  2. Strongly invested in us (close personal relationship or a financial stake)
  3. Able to talk to us on a very frequent basis (at least weekly)

A mentor who meets these requirements is able to constantly give honest and quality advice to the founders, act as a sounding board for their ideas, and coach them through overcoming most of the common obstacles that first-time founders encounter. Such a mentor isn’t absolutely required, but they greatly improve the odds of success.

Successes

In addition to all of the lessons we learned, we scored a number of wins throughout the process.

We’re proud of the product we built — it feels professional and well-designed, it does what it does really well, and many of our users get significant value from it (just not enough value and not enough people).

Our marketing campaign at Penn was really well executed. With very little spending we were able to reach a wide audience outside of our immediate personal network and achieve a high level of awareness about our brand and product — we only wish we had continued to do with other college and communities.

We’re most proud of accomplishing our primary mission: carving out a space for the best content on the web. We never lost sight of this goal, and without a doubt, a lot of the best articles published in the past year are all on Vyrtex.

Was it worth it?

Working on our own startup was akin to working on a very difficult and complex project, in a very small team, where we had tremendous responsibility and flexibility. This was the first time that either of us were in such a situation — when confronted with a problem, we couldn’t just lean on existing organizational processes, traditions, and systems. Nor could we rely on having a boss tell us what to do. We had to confront problems head-on and solve them from the ground-up.

There’s no faster way to learn to swim than to be thrown in the water and forced to survive. We were often forced to learn new skills out of necessity — I learned a ton of technical skills, including Ruby on Rails, SQL, Google Analytics, and Mixpanel. We developed the confidence in our self-discipline and internal drive to stay motivated without a boss or supervisor. We learned what really goes into building an innovative, high growth business. And above all, we developed a more nuanced understanding of ourselves. Our day-to-day interactions, our successes, and our failures — all came down to just me and Taylor. The buck stopped with us — which made for a very humbling and immensely rewarding period of personal growth.

If we could make the same decision about starting a startup straight out of college we’d do it again in a heartbeat.

Of course we wish Vyrtex had taken-off, reached tremendous scale, and generated millions of dollars in revenue. But at this early stage in our career, it’s still a big win for us to walk away from this experience having grown rapidly both personally and skill-wise. If we could make the same decision about starting a startup straight out of college we’d do it again in a heartbeat. Forget all of the business, product design, and entrepreneurship courses — nothing better prepares you to be an entrepreneur than to just take the leap and go for it. We’re still figuring out our next steps, but we know the lessons we learned here will serve us well as we continue our careers and perhaps someday, return to entrepreneurship as second-time founders.


We haven’t shut down Vyrtex completely — it continues to deliver value to our users and we plan to keep it going as a side-project. If you want to get 5 quality articles about tech, politics, and culture in your inbox every weekday, signup here. And you can check out our social bookmarking tool here.

If you want to reach out to us to talk more, contact team@vyrtex.com or find us on Twitter: @dilipsrajan / @tculliver