A successful entrepreneur shares her thoughts on business success and failure.

Sharing my journey to one million dollars (Part 1)


There is a reason why I am compelled to write. As I follow along the path of creating my own business, gaining customers (and sometimes losing them), listening and understanding other entrepreneurs, I feel the almost uncontrollable urge to write it all down and create some sort of … story, per se. Something that people will resonate with. Something that makes you get up out of that chair and have courage to do what it is that you truly want in this life.. not just a “job”, but to really enjoy every moment of your being. I feel absolutely compelled to write it all down and share my knowledge so that you, too, can do this.

Someday (I assure you) this will all go in a book. But for now, you can read it first, here… my story of becoming a millionaire at age 26, and how I’ve almost lost it all, and how it almost never got started. Fear, courage, anger, passion, frustration, joy — you will experience all of these things should you decide to embark on a path of fulfilling your dreams. I can assure you that it will be worth it, and help you through the bad times. Hopefully you can learn something from my mistakes, and be inspired by the true stories of how I did what I did.

First, where I am now: My company, Simpli Hosting, which I started just after turning 20 years old, today has 7 employees and a few hundred customers, who on average pay a few hundred dollars a month for dedicated servers or colocation from us. Today I’m 26 and my company is valued at approximately $1.1 million. It was bootstrapped by me, and I own 91.5% of the company. The other 8.5% is owned by two people: one of my best friends in the world (Seth) and one of my most loyal employees (Sohrab.) I never took on any investors or venture capital, and strived always to make the company profitable while still offering reasonable prices to our customers…a message which I believe has come through to all who know me. I put my heart and soul into my business for 6 years, and now it’s time to write the whole thing down so you believe, at the end of reading what will become quite a book, that you can do this, too.

You’ll often hear it said that entrepreneurs are fearless. Let’s start, then, with the biggest fear of any entrepreneur: FAILURE. I like starting here because it’s a fear we all share. Remember this, when looking across the table and seeing other small business owners there, who may become your customers, investors, or mentors: They have all looked in the mirror and thought “What if I fail?” You share this with them. It’s the (mostly) unspoken bond between you and every other business owner in the entire world.

The best thing I can advise to get over this fear, then, is to set up an environment where you are not allowed to fail. What do I mean? My next piece of advice will be controversial. It goes against most of those startup “rules to live by”, and your accountant may turn slightly green at this… but it’s the only way my company would have ever turned into a full-time job and a million-dollar moneymaker. I set up an environment where I could not fail. If I failed, I would be out on the street. If I did not close deals, I wouldn’t be able to pay rent. I had very little money saved up (about $8,000). That $8,000 was only enough to live on for about 3 months. That was the key — if I couldn’t get the business off the ground in that time frame, it wasn’t going to happen for me. Lo and behold, I made it work, but there were definitely some scary moments!

How does setting up an environment where you cannot fail change your attitude? That’s the key question, and one that many fail to answer. Most entrepreneur/startup guides will tell you to have 6 months of cash reserves in the bank, and so on, and so forth. But what will make you succeed is not, by any stretch of the imagination, related to how much money you have in the bank. Your success is entirely dependent on 1) your attitude and 2) your willingness to listen. Let’s take a look, then, at how being “hungry” for those deals changes your attitude.

1) You quickly learn exactly what your customers don’t want. Having that extra money in the bank allows you to shrug your shoulders and say “Oh well, his loss” when a client turns down your proposal or, worse, stops working with your company. It allows you to point that finger of blame at anyone but yourself. But being hungry (and watching that bank account balance dwindle) forces you to look in the mirror and re-examine exactly what happened. What could you have done differently to save that customer or to get her to sign? Sometimes, realistically, there wasn’t anything you could have done. Someone in their company wanted to do business with a larger (more “stable”) company, or they had hired someone on their team who had other ideas about what needed to be done. But a lot of times, you start to realize that you could have tweaked your pitch, responded more quickly, or treated them more kindly. Perhaps meeting them in person would have helped (hint: it almost always does.) Don’t hesitate to ask, by the way, when a potential customer doesn’t sign or someone leaves… “why?” This will give you a great insight as to exactly what you can do differently.

2) You’re forced to listen to what your customers DO want. I found out that my customers were coming to Simpli because we offered personal service in an industry that’s not known for friendliness. I adjusted Simpli’s website and my sales pitches to emphasize this, quickly weeding out those who just wanted a low price and courting those who valued our service levels. I listened to existing customers, who said “More communication, please!” and started a company blog to keep in touch with our customers, as well as reaching out to them through networking services and sending personalized congratulatory letters whenever I saw them making news headlines.

Let me back out for a minute and tell a quick story. I was reading a popular tech news website and saw a mention of a new company being introduced. I recognized the name of the company owner, who was a customer of ours. However, he only had one small server with us, and his new company was hosted elsewhere. I emailed him, mentioning that I saw his company in the news, congratulating him on the new site, and dropped in a quick line at the end saying “If you need any help from us in the future, please don’t hesitate to ask!”

Later, he decided he didn’t like the huge company where his new website was hosted, and replied to that email of mine, asking for a quote. We ended up signing the deal for his new company in its entirety. Today he spends about $1500 a month with us. That’s because I reached out — not with a sales pitch, but with a “Hey, congratulations!” People like to be recognized. They love that you’re paying attention. And they’ll shower you with business if they know you’re supporting them 100% in their new venture. That doesn’t mean that you necessarily have to invest in their business, or think it’s the hottest thing since sliced bread. Just show that you recognize that they’re out there, trying to accomplish something and that you wish them success, and they will respond in kind.

That’s one of the most valuable lessons I learned about business. Being hungry to succeed means listening to your customers. It sounds simple, but it’s all too easy to point fingers and make excuses instead of thinking of your business as a fantastic learning experience.

More of this series (much more) to come soon!



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I'm Erica Douglass.
After selling my online business at age 26 for over $1 million, I created this blog to help you grow your own business quickly.

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