Observations from a 1st-time Entrepreneur

It’s the beginning of a new year and I resolved to blog more – mostly for posterity-sake. So I’ll start from the beginning of what I call “Act II” of my career.

During the Fall of 2011, I was canned from my job as a Product Manager at a company where I spent the better part of my twenties (8 years!). Things were pretty rocky towards the end of my tenure (which I won’t get into), so I was pretty relieved when the cord was cut.

I spent a lot of time trying to rediscover myself: I traveled, took up long-distance running, and hiked for hours in unclaimed forest. After months of trying to figure out what to do with the rest of my life, it was only after Steve Jobs’ death where it really started to sink in. After immersing myself in the numerous online tributes to the visionary, it was his 2005 Stanford Commencement Address (an amazing piece of oratory) that made me vow to never take a “job” ever again. I need to “do what I love.” Life is too damn short.

It was also around this time where I expressed my desire to work on starting my own company. But before getting there, I wanted to educate myself. So I took on two jobs helping two startups get off the ground (and working 100+ work weeks). I immersed myself in startup culture: I learned how to code, read Lean Startup cover-to-cover, attended meetups, hackathons, and fireside chats with Silicon Valley luminaries. In the Fall of 2012, I decided to take the plunge, quit my jobs, and work on my boot-strapped startup full time. 

The journey, to this point, has been enlightening, testing, and rewarding. While my words will sound familiar, I thought I should jot down some practical lessons I’ve learned over the past few months:

  • Start-ups are hard. This is something that people say, but you won’t really understand why startups are hard unless you’ve been through it. There are so many facets of building a business that you continually find yourself outside your “comfort zone.” You learn to become a better sales person, to build products, and find talent – not because you want to but because you have to/forced to in order to succeed. All of these activities have a way of grinding/gnawing away at your mind and body, which, I think is why many entrepreneurs have problems sleeping and find themselves in general poor health.

    Advice: If you are going to work on a startup, you need to be willing to put everything into it (time, money, relationships) because startups will literally take everything out of you. Exercising is a great way to clear your head, be productive, and kick a sedentary habit.

  • Rejection & loneliness. Being an entrepreneur is kind  of a lonely road to travel. Most people you talk to won’t understand your idea, no matter how good your pitch is. Investors sort-of understand what you’re trying to do, but they want to see who will lead your fundraising round before signing a check. Your parents think you’re crazy to give up financial stability to go chase a dream. Sometimes you even question yourself if you’re doing the right thing. It takes a different type of person to dismiss/accept rejection and continue marching down a path with no clear end in sight.

    Advice: Find yourself a co-founder who shares your vision. Surround yourself with supportive people. Rejection is quite possibly the biggest source of motivation to prove people wrong.

  • Figure out what’s important. Bootstrapping a startup makes you ultra-conscious about your lifestyle choices. Do you hang out with friends or do you spend time working on user on-boarding processes? Do you go out for sushi or will ramen suffice? Should a button have a 5-pixel radius edge of 7? All of these little decisions affect how much sleep you get, the balance in your bank account, and your relationships with people. 

    Advice: Life is full of decisions. Time is a luxury. Choose wisely.

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I’ve found these past few months to be the most scary, frustrating, exciting, fun and self-enlightening experiences in my life. In fact, I recommend that everyone should try to make something of themselves, because life is too short to NOT find out. There’s no harm in trying and you’ll learn lots, promise.

PS. If you want a preview of what I’m working on, check out www.dandilyapp.com