What 1 Year Running A Startup Has Felt Like

The dice were in my hands – it was my turn to roll. I had hotels on Kentucky, Indiana and Illinois Avenue, and a few houses on New York and Tennessee. I was down to my last few dollars and knew that if I landed on anyone else’s property, I’d be bankrupt. My only shot at winning was to dance around the board, hoping to land on chance / community chest until someone landed on me enough times to put some cash in my hand. As I got ready to roll, I couldn’t help but feel a familiar feeling. It was exactly what I was thinking every day as I got up to work on our startup.

The story of our startup in a nutshell

We spent months pre launch cycling through various developers (majority of them from India), each with the same story – A broken promise that they could get what we wanted done by the date we gave them. They all ended the same way – deadlines missed, sub par work, tons of frustration being at the whims of someone else.

We must have pushed off our launch date a good 5 times before we made the following decision: 

Come January 1st, whether or not we have a working website, we are launching this company.

The weeks leading up to it were stressful as we pulled close to 16 hour days to meet our deadline. Finally, the day hit, and we pushed the launch button.

Ok, We’re Live. Now what?

We got our website up, which included tons of bugs and missing features,  and had no idea how we were gonna market this thing. Probably the toughest lesson that we learned really quickly was that you could have the best product / service in the world with a poor marketing strategy, and you’ll be as good bankrupt. Conversely, you could have a mediocre product with a solid marketing strategy and you’ll be a millionaire (a billionaire is probably pushing it).

But how do you market a service? Do they teach us that in school? No, they teach us how to find the slope in calculus, or how to calculate the present value of a bond. Here we were, 2 young kids who just quit their full time jobs, with a new company that we had dreams would revolutionize the way education is being done, and we had no idea how to generate traffic and earn a dollar on our own. How would you get the word out?

Tell Anyone and Everyone and Hope They’ll Listen

We emailed friends and family, we posted all over every social media outlet, we cold called and cold emailed 100’s of organizations we thought may be interested in our service. The results were minimal. I had just started taking a Brazilian Jui Jitsu class, and I didn’t know what was a bigger struggle. Fighting off a 200lb guy from choking me out, or trying to get someone to try out service. Note that I said “try out”. We weren’t even focusing on sales, we just wanted someone to try a free lesson and give us their thoughts. Another one of the many things we learned really quickly is that just because something is free, doesn’t mean people are going to try it.

A Few Sales Later and We Were Making Traction

Finally, we had someone who heard about our services from Judah’s dad try our services, and make a purchase. Now, I don’t know if you’ve ever experienced the feeling of convincing someone to go into their bank account and transfer their hard earned money to you for something that you created, but let me tell you, it’s a real powerful feeling. True, it was only about $150, but it was a step in the direction that we were dying to go. Shortly after, we picked up a few more people, mainly through reaching out to people on Twitter, and we had our first few recurring customers.

Let’s Talk Coding School – You Up For Manning The Front While I’m Gone?

Judah reached out to me one day that he had real big news that he wanted to discuss with me. He reminded me of the struggles we were facing with dealing with developers who didn’t care for our vision, and who were slowly depleting our bank account and our peace of mind. “What are your thoughts on me going to a coding bootcamp for a couple months, learning all of this stuff, coming back and doing things differently with our company?” I’d never heard of a coding bootcamp before, and the thought of Judah leaving when as it was we were already struggling freaked me out. We spoke it over, and I could tell that it was something he really believed in, and that regardless of the outcome of our company, would add a ton of value to his life. I gave him my blessing, and a few interviews later he was scheduled to go out to a bootcamp in Hawaii starting the end of May.

At What Point Are We Throwing In the Towel?

Judah going to coding school forced us to have some real tough talks that would outline the potential fate of our company. The ultimate question was “Where do we draw the line between deciding we’re not capable of carrying out this idea at this point in our lives, and continuing full force until we 

make it big?” We came up with a number and agreed that if our sales weren’t at that amount by a month or two after he got back, it’ll be sayanora to our idea. It was easily one of the most challenging moments I had experienced. The thought alone of us calling it quits petrified me – so much to the point that I remember going to sleep craving I was back working at KPMG for a steady paycheck. Things were rough, and now for the next 3 months I would be doing it all alone.

Easily the biggest 3 months of the year

Something really strange happened during those 3 months while Judah was gone. Maybe it was because we put all of our development on hold and just focused on marketing, or the fact that we starting using Google adwords, or even the change in seasons from the cold gloomy winter to the beautiful sunny Spring; but suddenly we started getting the traction and validation we were looking for. People were trying our service – people who we’d never met or spoken to before, and they were making large repeated purchases.  We had multiple lessons going on every single day, and our professors were finally busy. We even started breaking a monthly profit. It was one of the most exciting thrills I had ever experienced. No, we weren’t pulling in 10s of thousands of dollars, but we were finally getting traffic. Our actions were finally being reinforced. I was even beginning to tap out a couple people in Jiu Jitsu. Amazing how sometimes when it rains, it pours. I’m glad to say that we hit the number Judah and I set before he went off to coding school, and we agreed when he got back that we would continue on this path in the hopes of expanding more and more every month.

Where we’re at right now

The biggest thing that happened to us this year wasn’t the increase in sales, it was bringing on a new partner, our close friend Akiva. I told Akiva a while ago that he always had a spot in our company, but at the time he didn’t sound too interested. By some miracle, on his wedding day, he told me the good news that he was planning on joining the team. We went from 0 developers, to 2 developers ( I even learned some HTML and CSS along the way). Now, all 3 of us are working on expanding to a new website which will include 10+ languages, and a couple musical instruments(Check us out over here!). Will we crash and burn? Still unclear. Are we loving it, learning a ton, and hopeful for the future? You bet ;-)

Drop me a comment below – I’d love to hear from you!