Lessons from my startup’s demise

This is a story I wrote three years back when we closed the doors of startup, TappedIn, and decided to move on. I am pulling it out of the archives and republishing here because I always want to remember what we did and why. Or more importantly what we didn’t do. After all, the measure of an experience, good or bad, is the lesson we walk away with.

Here’s the full story, again.

Three weeks back we decided to kill our baby. It was not out of the blue. This had been coming for almost a year now. But like good, gritty entrepreneurs we kept plugging away until the roof finally fell through. You would think it took a big crash for us to call it quits but it didn’t. It was the smallest thing.

A missed meeting. That’s all it took.

I’m glad for that missed meeting. Glad for the slightness and triviality of it. If it had been a major setback, like a deal falling through, our entrepreneur instincts would have kicked in and we might have hunkered down with renewed energy to ‘fix’ it.

But something simple like a missed meeting did such a great job of sealing the deal and helping us move on.

TappedIn officially launched in Feb 2011 but my cofounder and I had been plugging away at it since September 2010. TappedIn was a pivot from our 6-month endeavor of testing the waters with our original concept. And now 2.5 years later we have reached the end of our road.

This post is not going to be a eulogy or sob story recounting our failures. I mean it to be a document of our journey, a testament to the bumpy ride we had and reminder of the reasons we have bruises right now. More importantly, it is a compilation of the lessons learned along the way. It is mostly for us to learn from and move forth with gusto but it is also a gift so someone, somewhere can avoid the mistakes we made.

Here goes:

The early bird gets the worm: We were relatively early in the social discovery space. No one was talking about or interested in the ‘discovery’ of people, until early 2012. It exploded at SXSW 2012. By then we were 18 months into the game. We had a beta product, partnerships with TEDx and Eventbrite, we had proven the concept with a handful of clients and had even made some revenue. My cofounder and I were plugging away at it fulltime. We should have raised money then. Instead we waited for ‘just one more improvement’, ‘ just one more event’, ‘just one more bug fix’ and before we knew it, we were at the end of 2012. Social discovery had fizzled out by then, our competitors had raised a ton of money, my cofounder had had to find a full time job and we weren’t dramatically better than where we were a year ago. It became really hard for us to raise money at that point. Without cash in the bank, our CEO was unable to work full time, nobody was taking home a paycheck, we were barely able to pay bills and were severely demotivated. Lesson learned: If you know you have a short runaway with personal cash, raise early so the question of paying rent is off the table.

“All great things are simple and many can be expressed in a few words”:(Churchill) Our tagline was ‘Make conversations matter’. To this day we still aren’t sure if that was the right tagline for TappedIn. We spent weeks, maybe months trying to figure out what it was. We knew it would evolve over time but we just wanted to get close. And we couldn’t. This was because our stated vision was too big and too vague. It didn’t directly tie in to the product we were building. We were unable to tell our story well or connect the dots well because we claimed we wanted to change the world but we were building something that most people didn’t think they’d even need. Lesson Learned: Have a powerful vision but make it easy to relate to, easy to build toward and easy to adopt.

It is not the unmelodious but the discordant who ruin the orchestra: There’s still no unilateral consensus on the tagline. We all had different ideas\perceptions of what the mission and vision of the company was. If you’d ask the three of us (CEO, COO, CTO) to pitch, you would hear different words come out of our mouths. This stemmed entirely from the fact that we hadn’t truly internalized the mission. This made decision-making extremely tedious and complicated. We each approached it from three different points of view, spent hours, days, sometimes weeks going back and forth figuring out the next step. Before we knew it, a lot of time had slipped away in ‘brainstorming’ without getting any real work done. Lesson Learned: Make sure the entire team is on the same page and is united in their thinking about the purpose of the product and its impact.

That which can be broken will be broken This is such a simple lesson oft retold. And like all basic rules of life it is easier said than done. We knew we needed to have unwavering belief in our vision and the problem we were solving but it was so hard to stick to our guns in the face of ‘feedback’ from seniors in the industry. We were looking to sell our story not looking for someone to buy our story. We should have firmly believed that there’s someone, somewhere out there who will ‘get it’ — who will believe in the story as passionately as we do. Lesson Learned: If there’s magic in what you’re building, trust that there’s someone out there who will believe in the magic too. Your job is to find that someone. Not change the colors of your magic.

Observe the opportunity, define the problem, discover the market and invent a solution: This seems like common sense but is so easy to forget when you are in the thick of things, lost in system crashes, bug fixes and an oversized social media diet. We easily ridiculed the Silicon Valley ethos of ‘build it and they will come’ but were unable to shake out of our day-to-day business to go out there, sell, collect some letters of intent and come back to the drawing board. Until recently we kept pursuing a customer model that was just not working. The pieces fell into place recently and we did figure out who to sell to and how but it was too little too late. Lesson Learned: Don’t work in a bubble. Go out there and find people who will pay for what you’re building. Do this early.

Communication can make or break you: It sounds cliche but its true. Its do or die when it comes to internal communication within the team. It is key. Words matter. Intent matters. And most importantly, communicating the right thing at the right time with the right person matters. Our communication was broken due to several factors unique to our situation — past experiences, full time jobs, differences in personal values and misalignment of priorities. Communication sets the tone and energy within your startup so work on it from day one. Set the rules and create an internal protocol. Lesson Learned: Take the time to create a culture around communication. It is worth the time and effort.

Your team can be democratic or totalitarian, not diplomatic: What this means is that while every one enjoys the principles of universal adult franchise in decision making, they also have to accept the will of the majority, and if there is no majority the leader should rule with the fist of law. Either way is fine because it leads to decisions and therefore progress. The worst thing one can do is try to make everyone happy and in the process delay important decisions. We believed in looking at the 360-degree view of things, inviting everyone’s opinion and evaluating the situation from every possible angle. The result was bad decisions and terribly slow progress. Lesson Learned: Ensure the team is aligned but don’t pander to every whim and fancy.

If you are not the solution, you are the problem: Self-criticisms is one the most important skills entrepreneurs should have, but even more important is having an undying resolve to find a solution. We made a big deal of the obstacles that would get in our way instead of focusing on problem resolution. This stemmed partially from our lack of faith and partially from natural disposition. It put brakes in our progress and hurt team morale. Lesson Learned: There is a fine line between self-criticism and doomsday thinking. Be careful where you stand.

“Hard-work always pays off” is an over statement: At some point we started feeling entitled to success. We felt burnt out by the long hours and sweat we were putting in and just wanted to see some light at the end of the tunnel. We were spinning our wheels and while that was squeezing every ounce of breath within us, it wasn’t helping moving us forward. This sense of entitlement played a big role in making us slowly fall out of love with our company. Lesson Learned: Burning the midnight oil doesn’t automatically guarantee success. Results do.

There you have it. This was our tale with all its pitfalls and holes.

We feel heavy-hearted right now but humbled and grateful to have been part of the journey. We were a great team that truly loved and supported each other and we were deeply fascinated by how TappedIn could forever change the way people networked. We couldn’t quite get it right this time but we will be back with something sturdier and better.

If this helps even one person avoid some pitfalls on their journey, this will have been worth it.