Four Keys to Achieving Bootstrapping Success

Guest Article

When I began my entrepreneurial journey back in 2007, I had no idea what was on the horizon. An economic crash in 2008 brought my life to a screeching halt, and I’m sure the same happened to many of you. After weighing my options, I decided to start a new type of advertising company in a brand new industry. Some entrepreneurs have thought things through, developed a business plan and are fully prepared. Like many business owners, I didn’t do that, and I just wasn’t prepared for the challenges, obstacles, and struggles that would follow in those early years.

Sand Hill Road Fallacies

Living near the famous “Sand Hill Road,” I thought the investor community would take kindly to a local boy who was trying to achieve his dream. Instead, I had nearly every door shut in my face. And I met the snickers and stares of doubt, which I began to think was due to my then 20-something appearance.

The questions were like a broken record. “What makes you think you will be successful at this?” “We have never heard of you before, where did you go to school?” “What does your family do again?”  Then the brutal assessment would come, “We just don’t see this idea working or making any money.” “Come back and see us when you make $1M in revenue”

Through these trials and tribulations, I’ve learned to discover some key rules that all entrepreneurs should be aware of and must follow in order to achieve bootstrapping their own business:

  1. Establish relationships with other highly credible entrepreneurs

Iron sharpens iron. You need to surround yourself with other business owners who are going after just as big and exciting things as you are. Build as many professional relationships as possible, and align yourself with a new circle of friends who are going through the same steps paces you are. Find time to meet for 30 minutes over coffee or drinks to hear what they’re doing/ Always looks for ways you can be of assistance. These meetings are great opportunities to strengthen your network relationships – pay attention and stay engaged by listening.

  1. Have an unwavering belief in what you are setting out to achieve

Never allow doubt or disbelief to drown out the motivation of success that has led you to this point. Learn to distinguish constructive criticism from negative comments from those who just don’t get it. Completely ignore opinions that hold no value. Adjust the time you invest in people, while also making the necessary sacrifices in order to follow through on strategic networking opportunities. You real friends will understand your need to prioritize your business.

  1. Be willing to make any sacrifice necessary

I was a senior in college when I created my company. Others around my age began to settle down. I chose the focus on building my business as that was more important to me than getting married and starting a family. I have no regrets. You have to make these kinds of sacrifices in life to live your dreams.

  1. Stay humble, grateful for every single opportunity

Understand that there is a very fine line between being excited and coming across as arrogant. Don’t be a jerk, or you’ll turn off many people who can help you. Remember your roots and how hard the struggle was for you.  To this day, even the smallest deal means the world to me. Anytime anyone is willing to invest in what we are selling, it’s a great opportunity to show my appreciation. At all costs, never lose that “customer first” mentality.

If you are going to bootstrap your business, this mentality should be your outlook as you build your business. Starting a small business on your own with zero outside financing is hard but very possible. You certainly appreciate the wins a lot more, because you earned them. Keep these four keys in mind and stay coachable, and you will have the business of your dreams.

About the author

Matthew Olivieri is founder and chief executive officer of AdSemble, the leading online marketplace where advertisers can name their own price for digital out of home campaigns.

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