4 Common Startup Mistakes I Made While Cutting Down A Tree

Last weekend, I chopped down a tree. I was too cheap to pay an extra $200 to have it cut down by the construction crew building a fence in my backyard, so I did it myself. Although I’d never cut down a tree before, it wasn’t a particularly large tree, so I figured I’d make quick work of it.

As I walked outside to unearth the offending oak, I told my wife I’d be done within an hour. Five hours later, I was exhausted and sore and had one less tree in my yard.

Since this isn’t a timbersports blog, I won’t describe any of the actual lumberjacking. Instead, I want to reflect on my naive “done within an hour” prediction because my miscalculations about cutting down a tree are the same kinds of mistakes I often warn my students about when advising them on their startups.

Mistake #1: Having the right tool doesn’t mean you won’t spend time configuring it

Though I don’t foresee myself felling many tress in the future, I took the time to get a chainsaw (in this case, a chainsaw borrowed from my in-laws). Why? Because cutting down a tree with a chainsaw is simple. Even as someone who’d never held a chainsaw, the time between blade-touching-bark to tree-on-the-ground was less than a minute. The relevant lesson here is that having the right tool for a job is usually well worth the cost.

What I didn’t account for was the time I’d spend getting the chainsaw working. It needed oil. It needed gas. It still wouldn’t start even with fresh oil and gas. The starter chord was sticking. It needed some extremely-hard pulling before it was finally loose enough to crank the motor.

All together, getting the chainsaw to actually saw things took an hour.

The same phenomenon often appears in startups. When you integrate a new tool or service into your workflow, the value-add can be enormous. But don’t assume the tool will magically start doing its job. You’ll spend a lot of time learning it, configuring it, and troubleshooting it. Be sure to account for that time in your planning.

Mistake #2: Trees that look small are much larger once you chop them down

Sure, the little hardwood I hacked was tiny compared to the massive pine tree next to it, but once it was lying horizontal, what I thought was barely more than a bush was actually five times my height. I’d originally planned on carrying it to the street for the garbageman to deal with, but I quickly discovered I couldn’t even drag it.

The corollary in startups usually appears when choosing a problem to solve. Young startup founders are often oblivious to how complex a problem and/or market is. Instead, they only see what they believe is the simplicity of their solution. Once they start working on the problem — once they chop down the proverbial tree — they discover it’s much bigger than they initially thought. At that point, they’re too far in to stop. Instead, they’re stuck with a fallen tree in the middle of their yard, and they have to find some way to move it.

Mistake #3: You’ll spend relatively little time on “fun” things like your product

Since my goal was to cut down a tree, I figured most of my time would be spent gloriously wielding a chainsaw and forcing mother nature to crumble before me. However, as mentioned previously, the tree cutting took maybe 60 seconds. The next four hours were spent cleaning up a tree. That task involved only a tiny bit more chainsaw-wielding fun, but lots more bending, bagging, and hauling of heavy things.

Doing a startup is the same. You begin the journey expecting to do glamorous product-related work like development, pitching VCs, disrupting industries, and selling millions of dollars worth of stuff. However, no matter how successful your company becomes, the overwhelming majority of your time gets spent doing things like building lead lists, writing emails, creating reports, fixing bugs, sitting in meetings that go nowhere, and providing customer support.

Mistake #4: Sometimes it’s better to just pay someone else

While revolutionary startups do exist occasionally, they’re rare. Instead, most startups solve problems other companies are already solving. Their solutions might be expensive, but they probably exist.

If you’re creating a company to solve a problem that’s already being solved because the current solution is too expensive, you should take time to understand the real reason it costs as much as it does. Is the current solution expensive because the company that makes it is greedy? Maybe. Or the problem might require a more expensive solution than you recognize based on your limited knowledge of the space.

That was the case with the tree I chopped down. Based on my limited experience, the problem seemed solvable with an hour of chainsawing-fun. Instead, it was five hours of lugging, hauling, sweating, backbreaking exhaustion. Now that I’ve cut down a tree — now that I have more knowledge about a particular type of problem — I would absolutely pay $200 to have someone else solve the problem for me.


I teach in Duke University’s Innovation & Entrepreneurship program and founded RocketBolt. I write about startups, pedagogy, entrepreneurship, engineering, and poetry. They’re all related, I promise.

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