After nearly a decade of offering business planning services for startups located across 6 continents, I have seen entrepreneurs struggle with all kinds of obstacles. In this post I cover an obstacle that is at the top of my list - the Obstacle of Starting.

When I was 19 and attending college in Chicago, I had an idea for a custom-tailoring startup. The startup had an element of social entrepreneurship to it - the custom suits would be stitched by a community of skilled yet unemployed tailors in India. By 21, I had formed a great team, identified a profitable market segment, created a network of tailors and even won an award of $8000 from the Idea 2 Product Social Entrepreneurship Program at Purdue University. I flew to India, built a website that allowed customers to customize their suit online, trained the tailors to follow our new geeky measurement processes and completed a few successful paid orders by beta customers (success determined by the final "fit and feel" of the suit on the customer in the United States). With a little local publicity, I was soon approached by an investor who offered to invest $100,000 in my startup to take it to the next level. I declined.

When I look back now, I probably should have taken the money.

I remember my biggest fear at the time was that I didn't want to lose his money. Hiding behind that fear, was a lack of confidence. I hadn't figured out all the details yet with customs and imports, international payments and taxes, distribution, packaging, products returns and more. I chose to focus on these unknowns rather than focusing on what I already knew. The prospect of a large investment suddenly multiplied these unknowns tenfold and I froze. The startup never moved forward, my team disbanded and I moved on to other things.

Fortunately, I have learned a thing or two since then.

If you find yourself in a similar situation where you are unable to take the leap, there are two approaches that I recommend depending on your personality type - I call these approaches the Romeo and the Dr. Watson. At the risk of oversimplification:

1. The Romeo Philosophy begins with asking yourself "Am I really passionate about this startup?". I mean really passionate - the passion that transcends money and profit. If you are, then bet the house and the car (and other people's houses and their cars) and don't look back. If you are not, then try the Dr. Watson.
   
   
2. The Dr. Watson Philosophy begins with asking yourself "What is the worst that can happen?". This process will help you identify the biggest risks ahead of you which you can then systematically categorize and address. Over a period of time, you will find that your answer to this question is something that you are comfortable with. When you reach that answer, START.

I've had the good fortunate of working with both Romeos and Dr. Watsons. WomenLEAD is a classic example of a Romeo startup (or Juliet in this case). WomenLEAD is a women's leadership development platform. In 2013, they participated in the Boston Mass Challenge, the world's largest startup accelerator and I assisted them with their pitch deck. They were selected as finalists (128 finalists out of 1200 startups) and have since advanced from a simple concept into a full-blown platform with beta test customers. The video of the CEO below is a powerful example of the passion that I am talking about.

So, which approach do you see yourself taking for your startup? I would love to hear your comments.