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.

11 responses to “Scars”

  1. Hey Jason,

    Blind spots? Everything is a blind spot. I am cold calling, building relationships, and trying to develop an early customer base. I don’t know what I am doing, but it seems like it is working. Then I am recruiting people to work with me because I hate being alone. Being a lonely entrepreneur is, in my opinion, the worst feeling in the world. Especially when everything is a blind spot. I don’t know what I am doing, but it might be working. And I am trying to get myself organized enough to fundraise. I seriously don’t know what I am doing.

    It isn’t enough for me to get advice. I can be a little obstinate from time to time, and I also catch some junk advice from some places. So, to avoid allowing people who might not care enough to work through something with me to influence my decisions, I reject low effort advice. If it is a low effort idea, I will tinker with it.

    Put another way, I have my biases like everyone else. The kind of advice that is most useful to me is the kind that listens, deconstructs the poor decision, and then constructs alternates using the lens through which I view the problem. Of course, this kind of advice is really hard to find. For the most part, I really only get it from a few people, and they are people I have close friendships with.

    In the end, I sometimes choose to reject the advice and do it differently, but after having been through one of these kinds of sessions, I am at the very least better equipped to change course if I realize the results are not there.

  2. Question on this part: ‘Surround yourself with trusted advisors and be completely and continuously honest with them, then actually listen and learn.’

    How do you do that?  Do you have some sort of formal arrangement where you share stuff like this every week with these advisors?  That sounds like it could be overkill, but I also think that, if it’s informal/ad hoc, one might forget to share regularly and thus accidentally deprive yourself of important lessons.

    • Great question, probably worthy of an entire post.

      Here’s one thing I’ve seen a lot of people do: Find a small group of other entrepreneurs who agree to meet regularly.  People you trust and who hold everything you say with utmost confidence.  Inside the group you are required to be completely honest with everyone else, both in your own statements and in their reactions.  But also everyone understands nothing is to be taken personally.  Dispense with pleasantries and just focus on helping each other.

      With correct-minded folks, and ideally diverse both from background and industry, so you get new ideas, this is very powerful.  The people I know who have build successful groups say it’s the single most valuable thing they did for the business, and one of the most fulfilling things they’ve done as a human being.

      • I think I’ll adopt this idea.  If you can delimit a physical place in which nothing’s personal and set clear rules for what kinds of honesty is allowed (you can’t use it as an excuse to call someone stupid or ugly), then it’s possible to negate a lot of bad juju. 

  3. Good stuff, Jason. I’ve been a part of two mastermind groups for about 1.5 years now. We meet once a quarter for an entire day. The group includes people outside the Internet space, and that helps me bring an entirely different viewpoint to my business. It helps get me out of the linear way of thinking into a different realm. While not all the ideas are applicable, there’s true benefit of challenging past assumptions and looking at the world – and busines – a different way. 

  4. “you  literally cannot possibly know you’re wrong”

    It is *always* easier to see clearly from the outside where you are not weighed down by scars.   Getting outside perspective for you and your company is perhaps the single best piece of advice; but you only know this from being on the outside looking in. :)

  5. Oh man, that hurts.  It almost feels like you literally had me specifically in mind when you wrote this.  Guilty, guilty, and guilty.

    Actually I don’t think all VC’s are evil, but I did have a bad experience that cost me dearly.  And I don’t think Java sucks, it’s just that I have several years worth of C# code built up and I can’t just port it overnight.

    But yeah, not spending enough time talking to potential customers is a weak spot of mine.  I have my reasons, but they aren’t good ones.  Part of it has to do with time to vett vs. time to build.  If it takes 6 months to vett but only 1 month to build, why bother?  Why not just do it?  That’s the rationale, but then I wind up spending 2 years on it.  Oops.  Also, I haven’t had the best track record with vetting.  I’ve been talked out of good ideas, and lulled into pursuing questionable ideas.  Anyways, it is something I struggle with and try to get better at.

    – Kevin Dietz

  6. I keep on rewriting this post, but I’ve boiled it down to three principles:

    1) Vanity: Let yourself think you’ve “come up with the idea.”  If I’m doing something idiotic and eventually find a strong argument on a blog (such as this one), then it feels like I came up with it and I don’t feel like I’ve been attacked/ridiculed/etc.  A lot easier than having someone argue with me about why I’m wrong.

    1a) On that same note, indirect feedback is easier.  If I ask a candid question that predicts whether someone I know would buy a product I’m building, then there’s no visceral feeling that makes it seem personal.  And hell, why not do it that way? Directly stated opinions usually aren’t very reliable (if I had a nickel for every time I’ve heard people say “what a stupid product” only to buy it the minute it comes out…)

    2) Respect: There is always a way to show someone that what you’re saying comes from a place of complete respect.  If someone is being disrespectful to me and making it personal, I’m not going to sit around while they cause irreversible damage to my hippocampus; especially since those more disrespectful people are usually doing it from a place of insecurity.

    3) Reality: Reality is the most impartial teacher of them all.  I use fear as a compass for where the feedback is.  When you go into situations with intense feedback, you can get a very decisive and reliable idea of what works and what doesn’t.

    The underlying argument behind all of this:

    Our irrationality is here to stay, and social/emotional stressors are extremely expensive in terms of the energy we pay for them with (a bad day makes it hard to get up and work.)  Rational thinking/action is NOT CHEAP, so choose your rational thoughts and actions carefully.

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