Is Entrepreneurship For You?

Here’s the first session I did for our Pre-Entrepreneurship Bootcamp at The Div in December 2011. We had a great group of speakers with 12 budding aspiring entrepreneurs in the room for one full day of training.

I believe entrepreneurship should be a noble cause. As entrepreneurs, we should seek to change the world for the better.

Download the Audio recording here.

Here is my video:

Here are my slides:

On Rowing the Boat

Lately I’ve been using a metaphor about rowing boats to illustrate how each person on our team must add value or be removed from the team.

(Please know I don’t take letting someone go lightly. I’ve had to do it several times at iThemes, but it’s always a hard, and often emotional decision and one of the duties I don’t enjoy as part of my job.)

So here’s the deal … with any small business, everybody is in the same small boat together fighting against the current of normal business activities.

Unlike some big corporations, where a person could possibly “hide” and slip by with little or no actual work product to show, small businesses need everyone contributing, working together, as there’s often more work than enough warm bodies.

There’s little margain for error. (Google the statistics of small business failure if you need more convincing or ask an entrepreneur.)

So here are the rules of small business “boating”:

  • Everybody on the boat must row — Nobody gets a free pass on rowing. I realize sometimes you need a break from rowing. So yes, sometimes you need to take time to rest, relax, get re-energized and motivated, but then it’ll be time to get back up and start rowing hard with everybody else again.
  • Each person must carry their own weight and then some — This is about adding value to the team effort. Merely jumping in the boat and rowing your own addition means you’re simply watching the scenery as others are rowing the boat ahead. Each person should add something to the effort of the team in their own unique way. This doesn’t always mean someone is the strongest rower but maybe they are the most efficient. Either way, when you’re rowing next to your teammates toward the same goal and vision, you start realizing your rowing for a greater cause – the person next to you. Rowing comes in all kinds of different flavors but all must advance the mission of the team first and primarily.
  • Each person must be rowing in the same direction as the group — Sometimes people get in the boat and decide to steer the boat in a different direction than the rest of the team. This doesn’t just mean the team is carrying that person’s weight now, but they are actively battling AGAINST them. Or maybe they are distracted and don’t realize their oar is dragging. Either way, it must be corrected quickly, or else it’s wasted energy and time and money.
  • Failure to heed the laws of small business boating means …. you get dropped off at the next campsite (or worse, thrown overboard) — it’s a tough decision to take someone out of the boat, but I’ve found it also can dramatically increase morale (especially if the person is rowing against the team or causing distractions and problems within the crew).



On Doing Things the Right Way

As an entrepreneur almost every week you’re faced with an opportunity to do things the right way. Money and revenue allow our business to stay going and the lights on and our health insurance paid and all those fun things that let us do passionate, purposeful work.

But oftentimes when we’re scraping to get to the next level or pushing our beloved product out or see a competitor arrive suddenly in our space, we’re constantly faced with decisions to do things the right way.

Personally, I made a choice, a commitment early on to do things the right way and to be above reproach in my business dealings. But admittedly, it’s a constant decision I must make in business. Almost every day. And it’s not easy. At times, I have surely failed at it. But overall, I know doing right by people is the best and only way to do business.

Yet the other way looks remarkably easy and tempting. It often has quicker results. But it’s also a recipe for long-term disaster. (And to have people label you as a douchebag.)

In the early days I saw fellow entrepreneurs use controversy and shady tactics just to get fame and exposure. They leveraged other people’s hard work and reputation and took shortcuts every way they could.

But they lost all respect in my book. I made mental notes that I’d never want to do business with them, or even get to know them, and figured others might feel the same way. I thought to myself, “When they grow and need people to work with them, how will they go about recruiting good, talented team players when they act this way?”

As the saying goes … what goes around, comes around.

This type of consistent behavior will catch up with you.

So here are some questions I try to ask myself before I make critical decisions ….

  • Are my actions ultimately going to damage the long-term health and reputation of my business?
  • Would people want to work for me?
  • Would people be more or less likely to want to partner with me?
  • Would key people still like or at least respect me as a result of my decision?
  • Or here’s the big one … is this the right thing to do, no matter what the cost?

I sleep well at night because I know consistently I seek to do the right thing in business and by the people I’m involved with and that our business has a purpose for helping make our corner of the world better each and every day. When I mess up, I hope to always acknowledge my mistakes, ask for forgiveness and learn and grow from it.

(And by the way, doing things the right way doesn’t mean you allow people to walk all over you or stomp on your face. But that’s another post on Boundaries.)

Doing things the right way means it costs more, takes longer, hurts more …. in the short term. But it’s really the only way to do business.

On Being Too Soon or Too Late

Fear is indeed a great motivator sometimes.

Today, I thought about some of the things we’re trying to do with our business – from hiring 6+ new people in the last couple of months to starting a nonprofit foundation after just being in business for 3.5 years.

And I had to ask myself this question: Would I rather be too soon or too late?

When I think of this question it is in the context of innovative and new things that push the envelope of traditional (or normal) business operations… i.e. anything that involves taking a chance on something that typically is untraditional, unorthodox, untested … or even at a faster rate than usual (like a startup starting a nonprofit).

The answer for me is simple … I’d rather make a mistake doing something too soon (generally speaking) than being too late to the party.

I’d rather have tried and failed, then never have tried and be bitter about missing the opportunity. And I’ve met my share of bitter people who either squandered an opportunity or watched it sail away. (Either way – they have themselves exclusively to blame.)

Oftentimes, being too soon means somebody behind you sees what you are doing, is inspired, and creates something even better. That’s because being too soon sometimes means you are a pioneer. You are busy cutting the trees in the forest, when others can watch from a distance and see the forest you’ve discovered.

It sucks for the pioneer, but only if fame and glory is your chief game. True pioneers enjoy the journey of discovery.

But the opposite side of being too late to the party often means you are perhaps overly resistant to risks or anything new and therefore, apathetic. You sit on the comfortable manicured golf greens far away from the trailblazers and scoff behind your binoculars at them (while often being consumed with jealousy). You mistakenly think that the safest place is to stay exactly where you are.

Think of the trailerblazers, the innovators, the creators, the explorers throughout history who took a chance and did something perhaps “too soon” …. they conquered new worlds and created new nations, economies, life-changing inventions and industries. Think of all their detractors. Their names are lost, while the names of the ones they mocked are craved forever into history.

For me, I’d rather push the envelope and take calculated risks (see the affordable loss principle) to do something new and innovative and make a bold step forward into unexplored lands … all the while taking the risk of falling flat on my face and being laughed at, for the sole purpose of doing something special with my life and business that MEANS and STANDS for something.

To innovate and to explore and to create.

I don’t mind taking the chance on being a too-soon embarrassment rather than being a too-late, has-been, never-was.

What about you?


Introducing The Startup Handbook Series

As part of StartupSofa, I am going to be sharing our Standard Operating Procedures (SOP) that I have been rough drafting for iThemes for several months (well, ok, years) but just now filtering through our internet communications.

I’m calling this series the Startup Handbook … it is my/our way of doing things, our formula if you will.

The goal of doing this for our team is to communication our “way” of doing things, our procedures, values, etc. for new people we add to our team.

I quickly realized that if all of this information was locked in my head, I would quickly go crazy and also become the bottleneck for our business.

I think this is a big area where founders, like me, struggle. Taking a one-person shop and becoming a team as you add more and more people to the equation. And the tendency for founders is to micromanage and hang onto everything we can because “it’ll get done the way I want it” or “the right way if I just do it.”

That’s a recipe for disaster.

So anyway, here is the first SOP or post in the Startup Handbook series, which is an introduction followed by some videos I did for it …


I did these short videos this week to highlight some of the core values and philosophies that define us as a team and business.

My purpose in these videos is simple: I want you to get to know us and what we’re about at our core.

They can also double as our team handbook as we preach and teach these daily.

If you know who we are, then you’ll better understand how and why we do things, deepen your relationship and trust with us, and ultimately, be happier in our community knowing these things, which makes us happy!