The original UPlanMe homepage #RIP

UPlanMe began as a consumer app—a personalized “smart calendar” that updated itself automatically when your favorite bands were in town, TV shows were on, sports teams were playing, stores were having sales, and restaurants/bars were having events. 

After about a year, we pivoted the company to a SaaS platform for restaurants, bars, and stores to manage their specials, sales, updates and events from one dashboard that pushed out to their own website, their Facebook page, and a third-party network of apps and sites that were ingesting our data.

The OG UPlanMe was the brainchild of my brilliant cofounder, Sean Barkulis and me after a coupl’a beers one night at an Alphabet City, New York dive. It was going to be our game-changer. Our Facebook. Naive, I know.

We envisioned a world where everyone was on UPlanMe. You could see what your friends were doing or wanted to do, no longer being forced to seek out the answer to the question “What should we do today?”

UPlanMe 2.0 was where we ended up when we realized that OG wasn’t going to work as well as we had hoped. It was a smart pivot, for sure, but not one we were passionate about.

UPlanMe 2.0

While UPlanMe was perhaps a “failure” by definition—the company shut down and we lost our investors hard-earned money—we both learned tons. I’m forever grateful that we made the decision to do it.

Here are some of the key lessons I learned in no particular order:

  1. Raising money to launch a company is easier than you think if your vision is clear, your network is strong, and your roadmap is realistic.
  2. Raising enough money to make that company succeed, however, is harder than you can possibly imagine. That’s why so few startups become profitable, go public, or even get acquired.
  3. When it comes to tech startups, specifically, if neither you nor your cofounder can code well enough to build your product yourself, you need to bring on another cofounder who can. You can’t simply hire a developer or development firm to execute on your vision. You will run out of money, then they will leave, and you will be stuck. SOL. You need a full-on skilled partner with real skin in the game. A partner, not an employee.
  4. You can make six month’s worth of cash last two and a half years if you forgo a salary, Airbnb your apartment for more than you pay in rent and sleep on someone’s couch.
  5. “If you build it, they will come” only works in the movies.
  6. Be nimble. I know this one has been said before, but bears repeating. My cofounder noticed the one bright spot in our blatantly failing OG iteration. We made the decision to cut away 90% of what we had built to focus on that 10% that had real promise. Still failed, though.
  7. Just because something shows promise, doesn’t mean it will work in practice.
  8. If I ever start another company, I’m not going to quit my day-job before it launches. I won’t consider making it full-time unless real cash-flow is coming in or I am no longer dependent on a salary for long-term survival

You can make six month’s worth of cash last two and a half years if you forgo a salary, Airbnb your apartment for more than you pay in rent, and sleep on someone’s couch.