Want to be an Entrepreneur? Read This First


I was just starting to find my professional groove, but something didn’t feel right. I knew certain aspects I had always wanted were missing from my professional life. Namely, I wanted to feel inspired — and challenged — by the work I was doing. I also was through working with clients that I didn’t choose. I wanted to be in charge of those relationships from start to finish. And, I wanted to be able to work location-independent.

Although it was a risky route to take, I discovered the quickest way to achieve all three of the points above would be to start my own company.

I said goodbye to health insurance and started taking vitamins. Steady paychecks and paid time off were a thing of the past and were replaced by new business wins few and far between to pay the bills, and tireless weekend work to refill my pipeline of potential prospects.

And guess what? It’s been an exhilirating roller-coaster ride every step of the way. There’s nothing like waking up in a pure panic in the middle of the night thinking, “Did I submit that RFP on time?!” or “Can I afford name brand ketchup, or should I buy generic until my next new business win?” I learned one thing about life as an entrepreneur very quickly …

Every single time you succeed or fail the experience is magnified because you are the one who is  quarterbacking the game; it’s yours to win or lose.

With that in mind, I’ve learned four essentials for every entrepreneur in the short time since I’ve left the stability of a day job for the helter-skelter lifestyle of a start-up entrepreneur. Hopefully, they can help you as you’re debating whether or not this career path is right for you.

Start Drinking Coffee

No, this isn’t a blatant plug for Starbucks (though I wish they were a client). What this does mean, however, is that you should be asking every single prospect, business contact, family friend, third cousin’s ex-wife once-removed … well, you get the point, out to a cup of coffee to pick their brains. Coffee is cheaper than dinner and can be scheduled at the very beginning of other’s work days when their minds are still fresh.

It’s the perfect way to learn something new about your/other industries, start a relationship with a new prospect or simply find out what your third cousin’s ex-wife’s name actually is (always important). It doesn’t matter if that connection can help your company immediately or 24 months down the road, you need to get in front of people and explain what your company is, what it does and why they should care about any of the above.

Say Hello to Kevin Bacon

Most people don’t realize how few degrees of separation actually exist between themselves and people they’d like to become their personal mentors/potential clients to pitch/connected individuals who could open up new prospect pipelines. More importantly, those degrees of separation are usually more than happy to blast off a one sentence, “Hey XYZ, this is a friend whose company does X …” e-mail introduction so that you’re not forced to cold call them yourself.

Take advantage of the connectivity we are blessed with these days and ask for introductions. Just make sure that you (see below) …

Give Back (a LOT)

Right when you start your company, it’s more likely that you are going to be asking for more favors than granting them. By asking for favors or introductions, pitching potential clients when you’re really only halfway prepared and generally looking like a fish out of water on how to start up a successful company, you’re going to soak up a lot of people’s time, which is the most important asset anybody in this world has.

Memorize the phrase, “What can I do for you?” as it will make you look like a complete Southern gentleman (or woman) … even if you’re a liberal hipster like myself. It also will help establish your credibility as a general nice guy/girl. Favors are built up over time; rarely does a contact need something right that very second, but I can guarantee that at some point along the line they’re going to need your assistance with something. You definitely want them to remember your offer to help out and hope to god they call you on it; this puts you in the +1 category when collecting favors.

Expect (and Accept) Failure

Nobody knows about you and nobody cares. If you think I’m being unrealistic, try cold calling a big company like Apple and getting through to a product marketing director on the first try. Yeah, that’s right — he did just send you straight to voicemail. Ouch!

Get used to it. You are going to crash and burn — a lot. It will feel like getting rejected by a thousand women/men at a bar in a single evening, and it will begin to take its toll on you. That said, don’t allow any negative energy to hover around yourself or your organization; negativity is real and it will steal every once of positive momentum your company has.

Instead of getting down, embrace failure and learn what things worked/failed you during your pitch process and incorporate these learnings into your next call. Keep in mind that you don’t need every single person to buy your product, just enough to keep the lights on through those first couple years as you build up experience and exposure in your industry.

And back to that coffee … you’re going to need a cup with all the sleep you’ll miss. So, why don’t you grab one now and dive right in. Your future awaits.