9 Lessons from 9 Years as an Entreprenuer

Exactly nine years ago I acted on my decision to never work for anyone again. I started Brand5 out of the dining room in my apartment with exactly zero clients and a very small bank account balance.

Nine years later I’m proud to say that Brand5 is still very much alive (and thriving). The company’s success has afforded me the opportunity to take some additional entrepreneurial leaps. I’ve been fortunate enough to start and sell two other companies in addition to Brand5 – Beelya and FileLater – and I’m working on my next one already. As a result, I’ve become passionate about starting, and helping other people start, their own online technology companies (my term for websites). For me, nothing is better than taking something from the back of a napkin or a white board, turning it into something real, getting customers, generating revenue, and wrestling with all of the things that can happen trying to make it grow into a real product or service.

Along the way I’ve learned a crazy amount of lessons. I do my best to take those lessons with me when I work with clients or on my own ventures. Here are nine (9 years, 9 lessons get it?) that I hope will help others out there trying to find their way building their own online business. As always, forgive the plethora of sports analogies. I’m a big fan of business and sports and the two often get mixed together.

Do one thing really well first.
It’s easy to get caught up in the potential of an idea, to look ahead at everything it could be one day. Chances are an idea’s potential is almost impossible to achieve out-of-the-gate. Instead, use a logical, realistic starting point to begin your online company. When thinking about what an online business should look like the day it launches, make sure it does one thing really well (as opposed to more than one thing done not so well). That one thing should be the core functionality – the reason the site exists. If your idea is to make it easier for people to share photos, make sure it’s easy for your users to upload and share their photos. Resist the urge to do the next 10 features that will make it even better. If that one thing doesn’t work, it will be hard to get people to try the other 9.

Give me a winning team over a killer idea.
For sports fans, this is akin to the veteran athlete signing with a team because he says it gives him the best chance to win a championship for before he retires. This idea proves itself to me over and over again every year. If I’m weighing getting involved in a new project, I’d much rather work with a team loaded with talent and people I like and believe in over a project where I don’t know the other parties as well. If something I’m working on takes off to the point where a lot of time will be required, it’s critical to spend that time with people you like, respect, and trust. Starting something new is stressful enough. Interpersonal drama is wasted energy. It can, and should, be avoided.

Keep moving the chains.
The life/work combo gets busier every year. A couple of years ago I learned that it’s important to try really hard to keep things fresh. That’s why I vowed to launch at least one new product/idea/website every year. While I focus most of my time on what pays the bills (client work) I’ve found that I feel fulfilled if I have an idea working in the background at the same time. The more ideas I launch, the more I increase the chances that one of them will take off. What if it does? Then I’ll spend more time working on it and a little less time on client work. But here’s the key: you’ve got to keep moving the ball down the field with every idea. An idea stuck in neutral will tend to stay stuck in neutral. Set modest goals of moving the chains to get more first downs. You’ll find a nice balance of paid work and risk that can be extremely rewarding.

Don’t watch the standings.
It’s hard not to pay attention to what everyone else is doing.  Unless you are the luckiest person ever, competition is inevitably going to pop up. In my experience it always seems to happen at the worst possible time. Stop watching the standings on the scoreboard and get over it. Focus, instead, on making your product the best it can be. My suggestion is to keep an eye on what your competitors are doing, but don’t become obsessed with following their every move.

Try not to assume the worst.
Related to the last point – don’t assume everything your competitors are doing is smarter than what you’re doing. They got an article on a popular blog? So what. Stay focused on keeping your customer happy. Do that and it won’t matter what your competitors are doing.

Learn by failing.
Mistakes are a reality of being an entrepreneur. It’s what we do with those mistakes that shape our career path. We can either ignore the mistakes or, worse, blame them on someone else. Or, we can embrace the mistakes, chalk them up to experience, and move on. I’ve learned a lot over the years by failing on ideas, a lot of which I was convinced would work (like hiring a high-priced PR form to get press). When those ideas failed I moved on and remembered the important lessons I learned. I’m convinced that this is the only way to get better as an entrepreneur.

Cash is the ulimate power.
Starting a new idea or company without the cash to launch it and fund it for an extended period of time (in my opinion at least 18 months) is a one-way ticket to Failure Town. Without cash, ideas fall flat on their faces. Nothing ever gets done and the door is left wide open to competition. I see it all the time.

Your own cash is best.
I used to think that in order to be successful I had to go out and raise a bunch of money to fund a startup. Let me tell you that raising money isn’t the holy grail. Neither is running a VC-backed company for that matter. Contrary to popular belief, there are other ways to build successful businesses. For me, the best way to do it is with your own money. I’ve raised money and I have heard too many horror stories from people who work for BC-backed companies. It’s a super tough route to success. I’m not bashing angels and VCs. I’d be a moron if I was. All I’m saying is if you have the option, put together a great advisory board and fund the company yourself. This way you get the valuable advice that you need and you end up with a whole lot more equity and a lot less headaches and obligations. The obvious downside here is that self-funding is way easier said than done. Not many of us can afford to fund every great idea we get.

You never know who you’re talking to…unless you care to find out.
This is not a new lesson learned in the last 9 years. It’s something my Dad always preached that has been constantly reinforced over the years. It’s so important to treat everyone you meet with respect. You never really know who they are or who they know that could help you. I constantly see people lose interest in the person they are talking to after falsely surmising in 20 seconds that person is valueless to them. Not only is judging people so quickly rude, it’s a terrible move business-wise. All I’m asking is that you give people a chance. Over the years I have seen time and time again that the best entrepreneurs will always engage with you. And they all ask you, “so how can I help you?”.  They don’t worry about you stealing their ideas or taking up their time. They genuinely just want to help. We are all in this entrepreneurial thing together. More of us need to act like it.

Best of luck to you in 2012 with your endeavors. Keep a few of these lessons and mind and you will save yourself some time and money.

Feel the same or different about any of my points? Let me know what you think in the comment section below.