We Slept in an Office for 6 Months…and Still Failed

Story of a Startup — Wisdomly Post-Mortem


You always hear about the college grad who slept in his car while building a product, worked out of a basement to save money, or secretly resided in the AOL office as testament to his determination. But you never hear about those who hustle just as hard, make similar outrageous sacrifices…and still fail. As founders, you expect to be telling your story to eager reporters and not writing it on the pages that will soon become your post-mortem.

Accepting failure is never easy, but there’s a point where you come to terms with it, learn from it, and move on. I was the co-founder and CEO of a tech startup called Wisdomly. Wisdomly started as an educational platform for virtual meetups but ultimately pivoted to a customized online event platform. Our team included a former VC and former Google Engineer, and we received funding from Princeton’s Tigerlabs as well as Startup Chile. We hustled our asses off to make a killer product, but ultimately we failed.

The Journey

We had a wild ride and made a lot of sacrifices trying to get Wisdomly off the ground. Here are a few of them:

  • I lived in my former professor’s Wall Street office for 6 months, and another teammate joined me for the final two. We used the cleaning lady’s shower and got around using the freight elevator.
  • 4-5 team members slept at our accelerator workspace in Princeton at least once a week. When we weren’t sleeping there we’d live with an intern of the accelerator and his entire family.
  • We brought on our CTO from Google. He lost his H1B visa in the process of joining our team and had to leave the country to legally continue working with us.
  • At one point our team of 5 was working from Chile, NY, and India. It wasn’t easy but we made it work.
  • We once went on such a work binge that one of our founders nearly collapsed from exhaustion and an ambulance had to be called.
  • Finally, after being told we couldn’t actually live out of the workspace and concluding that biking the 4 miles to/from our residence was overly ambitious, we bought this beauty for a cool $500. If you recognize it from the side of Nassau St… that was probably us. It tended to stall every other day.

Gosh, she was a sweet ride


Shutting Down Shop

Unfortunately determination doesn’t always correlate to success as we shut down in early 2014. We weren’t seeing the demand we had hoped for, and after months of searching we decided it was time to move on. Wisdomly was a great experience and I was fortunate enough to have met so many incredible people, including my teammates who will forever remain lifelong friends.

I learned the most valuable lessons of my life during those seven months, both personally and professionally. Here, I share seven of the most influential ones with you in hopes that they impact you nearly as much as they have me.

Startup Lessons

1. Remember that your company is a collection of individuals

  • It’s easy to let the company become something greater than the people you work with on a day to day to basis. Realize that the company is an abstraction, whereas the people you work with are very real. It’s too easy to get lost in comments that revolve around the betterment of the company at the sacrifice of those who represent it.

Bottom Line: In order to retain talented individuals, people must feel like they are being valued. If they do not, time must be taken to address this issue.

2. Successful entrepreneurs do not inherently make good advisors

  • We had a vision and a clear strategy…until we met with a potential advisor/investor that had raised upwards of $100M. He loved our passion and strongly encouraged us to shift from live online education to live virtual events. “The opportunity is huge, imagine what could happen if you just land one big client. I can help.” We were pumped and high-fiving all over the place. That is, until our “advisor” stopped responding to emails and we found ourselves pivoting into an unfamiliar market that suddenly didn’t seem to be as lucrative as we once thought.

Bottom Line: Don’t let advisors steer your company. They are referred to as “advisors” for a reason.

3. Remove barriers to open and honest feedback

  • The first day we were all together we tossed around a ball and discussed our goals, thoughts, and expectations on how we should operate going forward. We promised that we’d have open and honest feedback sessions every two weeks. We laughed, and then we all came together and hugged. After that day, we never had a single honest and open feedback session until after we had failed. As a leader this was completely my fault, and I learned in hindsight how important candid discussions are to the success and well-being of the team

Bottom Line: Implement and enforce mandatory feedback and review sessions

4. Do whatever it takes to maintain momentum. Literally fake it until you make it

  • I believe that momentum is everything to a young startup. During the first few months we were receiving good news everyday, be it from an advisor, a new team member, or another program. During periods of non-excitement and development however, there were periods where nothing uplifting would occur. This is when we needed to manufacture momentum, and that should have started with effective goal setting and the intentional placement of positive “flags” (any event that you know will have a positive outcome).
  • Note: If you find yourself expending too much energy on this then it probably points to inherent and sometimes critical flaws in the company that need to be addressed. While in the short-term this is a great fix, in the long-term it can lead to disillusionment and distrust, especially if things go awry.

Bottom Line: There needs to be a fine balance between organic and artificial momentum.

The Tigerlabs workspace in Princeton

5. All work is not created equal: applying the 80/20 rule to everything

  • We worked too long and didn’t accomplish nearly enough. We slept at our workspace in Princeton weekly, passed out on our computers nightly, and felt stressed hourly. We put in all our time and effort, but failed to get a proportional return. No matter how many “lifehacks” you incorporate, there will always be only 24 hours in a day. Learning to prioritize will always be the most effective method to accomplishing your goals.

Bottom line: Choose the two most important things you want to accomplish today and start doing them. Right now.

6. Genuinely love the work you’re doing

  • We started with a vision that united everyone on the team: “To create a platform where users can learn, discover, and engage with others who share their passions.” We wanted to build an education platform, but ended up in virtual events. Once we stopped getting excited about our product, work was no longer considered a fun challenge. “Woo, I’m sleeping in my professor’s office!” became “ Why have I spent the last six months sleeping in an office on an undersized orange couch and showering in a janitorial closet?”

Bottom Line: It sounds so cliche, but ask yourself if you genuinely love what you’re doing. It’s a binary question, so if you’re able to honestly answer yes, then congratulations — otherwise begin making changes now.

7. Calculated risks are rewarded

  • Deciding to start a company is usually a calculated risk, yet people often fail to muster the courage to actually do it. If you have the expertise, passion, and hunger to build a successful company then I can promise that wherever the road takes you, you’ll end up better than you were before. The amount of learning that goes into taking a company from ideation to launch is unparalleled, and I can assure you that no classroom lecture, TED video, or well written article can prepare you for the challenges you’ll face.

Bottom Line: When starting a company, what is the worst possible thing that can happen? I’ll answer that for you. You’ll fail. Speaking as someone who is in the “worst possible position”, it’s worth it every time.

Get in touch at klokus.a@gmail.com

Special thanks to everyone who made this possible, including everyone at Tigerlabs, Startup Chile, and our wonderful professors.