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The Dark Side of Being An Entrepreneur

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I have been asked by several folks about my experiences in building out Skoop and the sacrifices I made to get here. I still don’t know what “here” is as we have just begun our journey but nevertheless, I always tell my story with the good and bad.

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Life as a new or budding entrepreneur is one of the most challenging and lonely journeys you will ever take. Here’s my story:

1. Depression is ever present and threatens to sneak in every day. I have intense highs on good days and intense lows on bad. But when your blood, sweat and mind is tied to your baby, this is unavoidable.

2. You work longer hours than anybody else because there is a constant threat that someone out there is working harder than you to take it all. Until you are an established startup, always assume that someone is doing it 2x times faster and better than you. If you stop, you lose.

Dark Side of Being An Entrepreneur

3. Entrepreneurship complicates family life in a way you never imagined. I have a wife and a young daughter. I am a workaholic by nature. But I had to learn and learn again that you must manage time for both every day. If you don’t, you will lose one or the other.

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4. Failures are a common and necessary part of your growth. Learn how to move past them with new knowledge. Our first product failed miserably. I was devastated because we had put so much into launching it. But I had to make a choice; blame the world for not accepting my product or blame myself for not studying my market enough. In any case, we dug into our failure and made our next version better.

5. Do not be swayed by massive valuations and round raises. Big numbers are certainly enticing but the #1 question each founder should ask him or herself is at what cost to my company am I raising x round? Cash infusion isn’t cheap. I had to learn the game here as I raised my seed round and chose my investors. I’ve had to deal with some pretty bad term sheets from investors where I walked out. Know your worth and stay true to your vision and only raise enough to get you going in that direction.

These are the musings of a 31 year old entrepreneur who left 9 years in corporate life to build something unique. Along the way, I have been through every possible emotion and then some.

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