Categories: Entrepreneur

The Dark Side of Being An Entrepreneur

I have been asked by several folks about my experiences building 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 the bad. Here are some of the points in The Dark Side of Being an Entrepreneur.

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 days. 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 as fast and better than you. If you stop, you lose.

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.

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 himself or herself is: at what cost to my company am I raising x? The cash infusions aren’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 since I walked out. Know your worth, 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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