May 2

8 Lessons for Entrepreneurs

Happy Anniversary to me. Yep, eight years ago this week (May 1, 2010) I re-entered the world of entrepreneurship by starting Converse Digital with a mere two weeks notice, no money in the bank, no investors, no credit line, a wife, four kids, a big mortgage payment and lots of private school tuitions. I’ve learned a lot along the way and today I wanted to share some of those learnings with you.

You Need an Entrepreneurship Runway

The common rule of thumb for starting a business is to have at least a few months income in your bank. Unfortunately, I wasn’t able to do that. I didn’t have the luxury so many of my fellow entrepreneurs have, where they don’t take a salary out of the company for months or years, instead reinvesting all profits to quickly grow the business. Nope, Converse Digital had to be cash flow positive from day one.

But this lack of runway has been a blessing and a curse.

It’s been a curse because I’ve never really had the chance to strategically grow the company. Sure, here and there we launch little initiatives like our Social Reconnaissance Products… or  our CIBER product (that I don’t even have a full webpage live for yet – just a quick landing page) usually after they’ve been on the drawing board for months or more.

But on the flip side, that lack of runway makes you scared. Every day you wake up expecting the other shoe to drop — a client to fire you, cut their budget, or maybe you don’t get that big project you were counting on or my favorite, a client falls way behind on their payments.

Every day you’re scared that today might just be the last because you’re living on the edge. But that fear, when properly focused, can be an incredible motivator. It creates a dedication that ensures you never “mail it in” and that you’re always trying to push the client’s work further, harder, making it more successful. It’s never good enough to just keep next year’s plan “status quo.”

It can even make you believe that you can actually will things to happen… new projects, new clients, or for me, new speaking engagements. Now whether or not I’ve actually been able to will those things to happen is up for debate but it’s funny how when I’m the most scared, and I really, really buckle down, that we pick up new clients or projects or a couple of speaking gigs land in my lap.

Learn To Network At Scale

The biggest mistake I’ve made, well maybe not the biggest but definitely in the top 3, not leveraging the same automation software I counsel clients to use so that I can maintain a constant follow up pattern with all of our leads.

I’ve started and stopped, did little micro-automation programs, etc., but I’m still not fully leveraging the power of automation to remarket to folks that have raised their hands and said, “I’m interested in what y’all have to say.”

Be Fearless

Whatever you do — be fearless. There is no shame in failure or falling down. There is only shame in not getting your ass back up. And that goes for those of you that aren’t starting your own company. Too many people are scared of failure in this world. From where I sit, there is only one time in your life to fear failure — skydiving. When you jump out of a perfectly good airplane and find yourself hurtling towards the earth at hundreds of miles an hour, then fear failure. Because if that chute doesn’t open you’re probably going to die. But in pretty much everything else, you’re just going to bruise an ego and scrape a leg, but you’ll live to fight another day. Trust me, I know of which I speak.

Have A Unique Point Of View

It’s gets really easy to just become kind of vanilla. Having a very distinct point of view, service offering or target audience means you can’t say yes to every client or customer that tries to hire/work with you. But man, let me tell you, it’s a killer.

First, it makes you harder to find in a digital first world. It’s hard enough to win Google and frankly, most folks won’t or can’t, when you’re highly focused and leveraged against a very unique, consistent point of view. But if you start trying to be all things to all people, folks just don’t know what parking space to park you and your company into, so you’re never the obvious choice for anything.

Second, if you’re always doing a project for the first or second time, you can’t achieve any real efficiency in how you solve that problem. The more you do something the faster you get and the faster you get the (in my case) higher the variable rate — since we charge by the deliverable vs hour.

Make Lots of Friends

And invest in those friendships, not because you expect anything in return but because you just want to create strong connections with people you like, respect and want to see be successful. Find folks for whom you’re comfortable serving as a Social Agent. I’ve developed a pretty simple filter… I ask myself, “would I invite this person to my kid’s birthday party?”

If the answer is yes, then I make the investment. If the answer is no… well, my kid’s birthday party isn’t the only thing they won’t be getting an invite to anytime soon.

It’s funny how these friendships end up saving your ass just when you need it the most by pushing a referral to you or hiring you to handle a project.

Make Momma Happy

There’s an old saying… if momma ain’t happy, nobody’s happy.

But it’s really not about momma… it’s really about family. Make sure your home life is solid. Make sure you’re investing as much in your family, friends and significant others as you are your business. Maybe it’s just me, but when things at home are askew, it’s just funny how fast that disruptive vibe bleeds over into the business and begins to cause problems.

Hire As Fast As You Can

Holy shit — why would you want to take on that commitment? That would just mean you’d need to sell more widgets or bill more hours or something. Just save the money, ease the pressure on yourself and hire the cheapest employee you’ll ever find — YOU!


Trust me… I did that during my first foray into entrepreneurship and while it wasn’t the only reason the company failed (Hurricane Katrina was a big factor) it definitely made it a lot easier.

Believe In God

Ok, for you non-religous folks, this one may be kind of a stretch. But hear it out non-the-less. If you truly think your success is completely in your own hands, that you and you alone are driving your destiny, great. But man that’s a whole lotta stress.

And not that you won’t feel that even if you do believe in God, but believe me when I tell you, over the last eight years I’ve had so many times where I truly needed a miracle to keep the doors open and the lights on. Funny thing — they always came.

There are those out there that will tell you they are just “killing it” and “they can’t field all the business they have” and in some cases they might just be telling the truth. But for every one of those “killing it” companies there are a hundred, maybe a thousand that have dodged their fair share of close calls. And in those cases, sometimes believing that someone bigger than you has your back can be the thing you need to keep your sanity, focus your attention and find a way to live another day.

And that’s it… eight crazy years… eight simple lessons. Take them or leave them… hopefully they help you think more about what you’re doing right and what you’re doing wrong in your own business.

Till next year’s post… Godspeed to you and may success find us both.

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