The Most Important Advice I could give any Entrepreneur

My last few posts have been India-centric, so you’ll be surprised to know that I am now in San Francisco. I probably wouldn’t be in San Francisco right now, a part of Batch 6 of the 500 Start-up Accelerator program if I had given up or played it safe. It took a slew of irrational decisions and a downright crazy way of thinking to get this far (which is not even half way to where I want to be, but I’ll take it). So if you don’t want to read anymore, than take this advice: having a dream is one thing, but reaching it requires not giving up and risking everything.

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The Journey to Now

As I winded down my full-time involvement in my second start-up (which happened to be in India at the time), I was faced with a decision of what to do next. Fashion and Technology was always something I wanted to get into, it was this pesky thing at the back of my mind that never really went away. For seven years, I filled up Google docs on ideas, made little PowerPoint presentations on various concepts, and even wrote guest blogs on fashion and technology innovations for awhile. So finally, I felt that I had enough confidence and experience to make a go of it, plus I had a bit of cash to live off of for a few months. So it was now or never.

While vacationing in Goa, I began thinking up ideas and landed on women’s accessories at the intersection of travel. I met a few fashion forward individuals to get their thoughts and together I curated a few accessories for women. It was a fun idea, but what I lacked was knowledge on the target market, and technical development. I did meet a girl along the way who had similar interests and killer experience, but lacked the entrepreneur “oomph”. Her idea of entrepreneurship was to take a sabbatical for four months from her day job so she could minimize risk and go back to it if it didn’t work. This thinking was too logical for someone like me who had nothing to go back to after failure, hence failure was not an option.

Having grown tired of being in India and the incessant hot weather after my stay in Goa, I booked my ticket home (Toronto) on a whim in early September. A few days before I left, I connected with my then co-founder’s friend who was working on a cool travel concept for men. I instantly loved the idea. My first start-up was in menswear and It was something I wanted to get back into but with a tech spin (and travel was just bonus), over women’s wear which I knew nothing about. But, he was in the States, and ironically, headed to India right when I was heading back home.

While I was home, I decided that perhaps I would just forget about the idea of fashion altogether, but then what would I do? I wasn’t really in the right mindset to get a job (which was probably a rational move, after years of mediocre success in start-up life). I slowly began working with the other co-founder of the men’s travel concept on various ideas and concepts through Skype. As luck would have it, I had to attend a family wedding in India in November anyways, so it was easy to convince my parents/family that I had to go back to India a few weeks early. I could meet with the team and try to work with them. I had never met them in person, and I went entirely on gut feeling. In fact, I had nowhere to stay, so relied completely on the kindness and hospitality of my eventual co-founder.

From there, we spent about 4 months, playing around with various ideas outside of fashion, pivoting and eventually getting the whole team to focus on one particular direction. It wasn’t easy, as we were all on our third or fourth (failed ot mediocre) start-up so there was that sense of defeat and anxiety as cash was low and was slowly becoming non-existent. A few times, I wanted to give up as our team while brilliant, lacked focus. Between the 1 hour commutes to an office, and the challenging living conditions – I felt that it just wasn’t worth it, especially when I had what felt like a utopia life back home. I went through what I call the dark days of entrepreneurship, where you question everything about your life, your past, your skills and realize how easy it would be to just quit.

But, thankfully, I did have support in Delhi. With that, I knew we had to keep going until we really had absolutely no choice. At the four month mark, we were politely asked to leave our office arrangement. Our last meeting in that office was us deciding that it was time to focus all our efforts on one idea and give it all we had. But with no office, and no money, it did seem impossible. We resorted to working in cafes with free wifi.

After a few weeks of café life, we finally began building something worthwhile and through some borrowing got ourselves an office and some wiggle room to build logistics. It was every so slowly becoming something that we could actually grow and scale, but most importantly, something that we enjoyed working on together as it played to all of our strengths. Regardless, it was still hard, and I had moments where I wanted to give up.. I was paralyzed with the fear of failing on yet another start-up. But, still I persisted.

Thankfully, we had someone who had watched us for months and saw that we did have what it took to grow a company given our combined strengths and past experience. He vouched on our behalf and became sort of our investor “cheerleader” and got us into 500 Start-ups. We had one day to put together a summary of our company and team to be considered.

To an outsider, this may look like luck, or an easy way in. But, nothing comes easy in life. It took years of working on start-ups, relationship building and even coming together as a team from all over the world.

It still feels a bit unreal. To go from struggling and wondering if we should go on, to meeting top investors, mentors and getting legit feedback on how we can improve. This is what I have been working for, not for the past few months, but for the past seven years. To be in Silicon Valley and running a funded fashion and technology start-up to eventually raise more money or sustain ourselves on our revenue.

It would not have been possible without risking everything and never giving up. It would not have been possible without following an irrational gut feeling. I flew half way across the world to find like-minded people who had similar values and  goals, but had a completely different skill set than me.

It’s not easy, and it still isn’t. Things have just gotten harder, or “shit just got real.” But for some reason, I just wouldn’t have it any other way. I don’t know, call me crazy. I’ll definitely write another post or several on the 500 Start-ups program.. #staytuned.

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