Scars

The skin between my second and third finger on my left hand has been dry and flaky since middle school; no one knows why. I have a scraggly patch of hair on my right calf from when I scraped off a swath of skin in an Ultimate Frisbee tournament. (I made the catch for the score. My wife asked “Was it worth it?”)

We all have scars. The interesting ones aren’t physical, and are more subtly revealed. It’s the guy who’s a little too steadfast in his claim that “VCs are evil.” It’s the founder who says she doesn’t need to talk to customers before embarking on a $100,000 development project because “my customers are idiots.” It’s the developer who is sure that “Java sucks.”

Scars are part of what make us unique. Dwelling on our peculiar trauma can be a comforting way to develop that uniqueness.

I like scars.
I want to remember.
I want to feel blood and tears.
I want it to feel tender.
I’m watermarked, just like forever.

– Matt the Electrician, Home

That uniqueness is good, or so says most advice. Embrace your scars, embrace your identity, own it completely, and suddenly you’ve solved one of the key riddles in life, not just in startups: Who am I, and how is that different from who anyone else is?

Some of my baggage, however, is a hinderance, whether it’s “defining me” or not. I still find myself sometimes running WP Engine like the bootstrapped startup that it was for the first 18 months of its life, instead of the funded growth machine that it’s evolved into.

For example, last week I spent about 10 hours saving about $1000/mo in hosting costs. Not bad, you say, that’s $1000/mo right into your pocket! You can even make a financial argument: That’s 10 hours to earn $12,000 over the next year, which means my time was worth over $1000/hour, and that’s a good hourly rate no matter what.

No, not no matter what. I could have used those 10 hours to make it easier to share a website speed report and to tell a friend about our free WordPress management portal. And that might have resulted in 1000 people seeing those two things over the next year, 10 of which end up moving their blog to us, and a few consultants who collectively put 20 of their clients on us. Even at $50/mo, that’s 30 x $50 = $1500/mo in direct new revenue plus side benefits in marketing and branding.

If you’re bootstrapping, getting that $1000/mo right now in bottom-line money is in fact the better choice. Money is scarce, time is precious, and $1000 today is better than $5000 next year (which you might not survive to see).

But if you do have money in the bank it’s just the opposite. The goal of investment is to turn “money today” into long-term value, meaning a growing, predictable revenue machine.

So even if you know your scars, embrace them, and have perfectly tight rationalization of why every decision is the correct one for you, it still might be wrong.

What can you do to mitigate this?

First, decide to build a company in which the correct, consistent decisions are the ones you’ll naturally take. If you love optimizing the last dollar out of the process — as I apparently do — build a bootstrapped company. If you don’t like working with people, be a Micropreneur like Rob and Patrick. If you want to leave a mark on the world, have big ideas with lots of people and lots of money, seek advice from those who have walked that particular path before you, to help construct your rules and structure.

Or second, do what I’m doing now: Surround yourself with trusted advisors and be completely and continuously honest with them, then actually listen and learn. I know I’m naturally a bootstrapper, a “get to the first $10m in revenue, but only after seven years, and then what?” type of person, so I know I need constant course corrections.

Really both of these reactions are the same: Get outside yourself and open your ears. Because, as in the example above, you literally cannot possibly know you’re wrong, not even if like me you’re proactively introspective and have a few successful startups under your belt.

I still rationalize. I still follow the ruts of my scars. I need other people to at least be an honest mirror and at best be a loving kick in the pants.

You need it too. Seek it out.

P.S. I’ll be your sounding board and your devil’s advocate, but in public (albeit anonymous, unless you ask for the exposure). Either write me at asmartbear -at- shortmail -dot- com to be a part of my Mailbag Series or better yet call in to the monthly Smart Bear Live show. Next one is in early February!

Where do you go for advice? Where are you blind spots? Let’s continue this in the comments.