Reboot
Starting over after leaving my start-up. What a ride.
Why am I traveling around South America?
I got booted from my own start-up and thought ‘hey, why not?’
Postponing my academic program, I took the year and worked full-time on Plexx, a start-up I co-founded focused on job training for youth without college degrees. We had began working in late October of 2012 and wow, has it been a journey since. In a matter of a year we dreamed up a product, identified an opportunity, secured funding, developed a product, piloted, filed as a company, and the original team disbanded. The speed was insane. At times it felt like a movie…and looking back I am still in disbelief.
Was it…
What we accomplished in such a short time?
The amazing people I worked with and met along the way?
The burn from my eyes from days and nights of barely sleeping?
Holding the first check from a funder?
Our hands clenched together as we waited for the judges to announce the winners of a hackathon?
…The air mattresses, sleeping on couches, endless nights, seeing the hue of the sun rise from the iLab, the rush from the pitch, suiting-up (orange shirt and blue tie), missing the deadline, struggling to put my thoughts into works, being too flexible, playing ‘moving man’ with my cousin, being too ridged…starting over.
It was all those things, wrapped in one package.
So what happened?
Well the entire story can be a book on its own, but in the end I decided I was leaving because my co-founder and I disagreed on the vision and direction for the organization.
After over 100 sessions observing and interviewing youth using the product I realized delivering all the job training needed on a mobile device to get a full-time job (and most importantly, the youth consuming all the training independently) was not a practical stand alone solution. It was not the phone as a vehicle, but the sheer volume of content and technology limitations that would need to be consumed to be ready for a full-time job.
At this point we needed to adapt our vision of being training vehicle or job search tool for those to get a full-time job or pick a new direction. My co-founder wanted to keep the solution we developed and offer it as a support service for organizations facilitating job training. I wanted to offer specialized training focusing on getting project based work and completing specific tasks to get paid, as I believed that was closer to what we can deliver as a stand alone solution. Both are viable routes…
At the time I was running our pilot in New York, representing the team in an incubator program in Santiago, Chile called Start-Up Chile, and handling logistics and other activities (which explains the travel between New York and Chile the passed few months). Through all that, we discussed that I was going to leave, when, and what I would do until then.
The conversation was tough but, comparatively that was the easy part.
We were in disagreement on whether I would remain an owner of the company and maintain equity. We had previously defined terms in our founders agreement, but my co-founder wanted to renegotiate. Our positions: I wanted to maintain my ownership and I was being pressured to give it up.
I went to Boston and we spent days discussing, debating, reflecting, and revealing. Feeling I was being pressed, I made a ridiculous offer for my ownership because I did not want to sell (that definitely did not make things better). But I felt there was a bit of sun after a meeting with an entrepreneurship professor and our presentation on our motivations to start a social enterprise at Harvard.
The next day on a bus, traveling back from Boston to New York, I received a call with the start-up lawyer and my co-founder. In short, the lawyer explained that I continue to accrue equity as long as I have not been ‘terminated’. Within the hour I got an email ‘terminating’ me from the start-up.
Going 100 miles a minute and all of the sudden it felt like was jolted into reverse. That night and the next morning I recall falling asleep and being awoken by the elevated heart beat from the race through my mental checklist and my sub-conscience searching for meaning from the last user observations.
It was time for a break…a real break, not a ‘working’ break, not another start-up, or a part-time gig…a reboot.
The flight to head back to Chile for the Start-up Chile program was already set and I needed to go back to finish the documentation, reporting, and events as part of the commitment to the program, so I did. By the end of December, it was all wrapped up and January was a blank page.
With my sketchbook, ample time, and a list of ideas, I was tempted just to dive back in.
Why not just pick another idea and keep moving?
Once you start seeing problems around you as entrepreneurial opportunities you really can’t turn it off. But I had this ticket and brought be back to the US in March after the program was over. So I decided to go, take a bus across South America, get lost, explore, discover, and adventure. I am blessed to have time time to do it now. So that’s what I decided to do, and what I originally felt was a tragedy turned into a gift. I got back time.
The journey has been awakening. Listening to the thunder of the avalanche crashing down the mountain in Patagonia and being soothed by the rawer of Iguazu’s falls has brought peace and awe. Hearing stories in hostels of travelers who have just finished school, lost a loved one, ended a relationship, and finished service in the Israeli army, has made a solo trek seem like a journey with friends.
As my friend Adrian from Start-Up Chile said,
They are all searching for something
What am I searching for? I’ll know when I see it!? Instead of simply executing to a plan, I am letting life take me. Trying to follow the designer mindset and doing what feels right instead of the engineering mindset of having goals, a plan, and executing. One thing that has taken me awhile to learn is following a feeling, even if I can’t explain the logic behind it, is the best reason to do or not do something.
Doing something your gut says not to do or vice versa is you telling your soul not to speak.
To end, I will share the quote that has been my guide on this journey.
— Steve Jobs, Stanford Commencement, June 12, 2005
