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The 7 Deadly Sins of Entrepreneurship

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These are the mistakes that successful founders avoid, and you should, too.

Last week, I shared what I consider the seven virtues of entrepreneurship.

Practices that I see the founders that I look up to hold near and dear; things that top performers are always working to get better at.

But just like successful entrepreneurs share many positive habits, I’ve also noticed that the people that I try to emulate tend to do everything in their power to avoid the same types of behaviors.

Today, I want to share the sequel to last week’s post: the seven deadly sins of entrepreneurship.

Make these mistakes at your own risk.

1) Losing Focus

Every day, new blog posts pop up with “the ONE thing you need to be doing to grow your business.”

The problem is that in 100 of these posts, you might find 100 different “one things”.

Hell, I’m guilty of it myself. We’re always sharing the “X things” that we’ve found success with in a given initiative.

But I always try to temper those takeaways with the caveat that it might not work for you, and that you should be really careful about what you actually try to execute on.

Because successful founders know: trying to chase tactics is a sure way to get distracted and derailed from your big picture goals.

Don’t get me wrong: I’m not saying that you shouldn’t try new things and test different approaches to your growth challenges.

After all, that’s the only way to determine what truly works.

But the wave of tactical tip posts that we face has created a culture of trying to do a million little things at once, and not doing any one thing particularly well.

That’s why it’s so important to have a plan, and focus on that plan with laser precision.

Set goals that are short-term enough so that you can re-evaluate and re-align every few months or so, but during those sprints, focus.

If it’s not in the plan, it doesn’t happen.

2) Assuming You Know Best

When we first launched Groove years ago, we build the product—and our site—on the assumptions we had about our market.

What we ended up with, after spending nearly $50,000, was a bloated, bulky app that had all of the features that we thought users wanted, but in reality didn’t really align with the needs of the market at all (the full story is here)… and the marketing site to match.

When we weren’t finding the adoption we wanted, we dug in, spent hundreds of hours talking to our users and prospects to figure out why, and basically scrapped the whole thing and started over, this time focusing on building the simplest help desk software we could, driven by the things that we now knew actually mattered, versus just what we thought mattered.

That was when everything changed for us, and I still look back at that initial build as perhaps the biggest mistake we’ve ever made.

Great entrepreneurs don’t operate on assumptions. They operate on an insanely deep understanding of their customers.

3) Small-Picture Thinking

The tech startup community is a close-knit one.

On one hand, I think that that’s a very good thing. Building a startup is hard, and having each other’s support helps a lot.

This community has given me a lot of incredible feedback, connections and opportunities.

At the same time, being in such a small group can change the way you think.

I’ve seen many entrepreneurs that are unable to look beyond SaaS startups as potential customers, because:

  1. that’s all they see around them, and
  2. that’s what they are.

But the thing is, this community makes up a tiny—as in, not even a blip on the radar—fraction of the businesses out there.

Now, selling to startups because you’ve built a product that’s truly best for startups is one thing.

But selling to startups because that’s the only market you see puts an invisible ceiling on your growth that you’re going to have a very hard time breaking through if you don’t get out and explore other markets.

There’s a reason that most of the successful startups that we idolize don’t make the biggest chunk of their revenue from other startups: that’s usually not where the money is.

4) Analysis Paralysis

People in businesses all over the world, every single day, spend far too long making decisions big and small.

It’s especially true, however, in startups, where we’re building things from the ground up. With the feeling of ownership that comes with, we feel a need to get every little piece “perfect.”

Unfortunately, that hurts us badly.

And it’s a lesson that I didn’t learn the first time that it hurt me. Or the fifth. Or maybe even the fiftieth.

But over time, I’ve internalized this lesson well, driven to the same conclusion as Mark Suster, who laid it out very well:

There’s a certain cadence that you can feel when you spend time hanging any well-run startup company. The management team has to have a bias toward making decisions. They know that a 70% accurate decision made quickly and based on sound principles is better than a 90% decision made after careful consideration.

The startup entrepreneur knows that they’re going to be wrong often. They’re flexible and willing to admit when they’re wrong. They don’t create a culture of punishment for mistakes. They live be the credo that if you’re never making mistakes you’re not trying hard enough.

In my mind the sign of a great entrepreneur is the one that spots the 30% scenario quickly and adjusts but doesn’t get gun shy about rapid decision-making in the future.

In fact, analysis paralysis drives me fucking bonkers. It is not uncommon in a meeting for me to say, “There are three choices: A, B, C. My gut tells me that we ought to do B. But let’s decide as a group. I don’t care if my view isn’t selected. Let’s make a decision and move on.”
Mark Suster

Great entrepreneurs are thoughtful, but they don’t let analysis slow down the business.

5) Avoiding Discomfort

Thanks to this blog, I talk to people who ache to pursue their startup idea, but won’t.

They say that they’re scared to fail.

But I’m not so sure it’s failure that they fear.

It’s discomfort.

The discomfort of telling people that you failed.

Of knowing it yourself.

Of hearing the word “no.”

Of coming to terms with the fact that things didn’t turn out the way you wanted them to.

It seems like a silly, semantic difference, but I think it’s really important. Because it’s a lot easier to get okay with discomfort than it is to get okay with failure.

Avoiding discomfort leads to keeping bad hires on the team, missed opportunities of all sizes, stalled growth, and ultimately dead businesses.

6) Not Taking Care of Yourself

I’ve lost count of the number of founders I’ve spoken to in their 40’s, 50’s and 60’s who wish they took better care of themselves in their 20’s and 30’s.

It’s a huge fear of mine.

Like most founders I know, I can be obsessive. Not “60 hours a week” obsessive. More like “forget to eat, sleep and acknowledge the people around me” obsessive.

I have to work really hard to not work too much. And while I’m not perfect, I do make that effort, for the sake of my own health.

Because a founder in poor health is doing a disservice to their employees, their customers, their business and themselves.

Don’t forget to eat healthy. Be active. And every now and then, take a vacation.

7) Not Investing in Culture

We’ve spent a lot of time and energy trying to build our remote team culture.

It’s not because I innately knew that it was important.

It’s because I’ve been warned about the massive risks of not doing it by the entrepreneurs I trust most.

I wish I had focused more time, thought and money into the company culture from day one. I have since discovered this to be the most important factor in the success of scaling any business. Core values, core purpose and integrating these into everything will give the largest returns you will ever see as a founder.
David Hauser

It’s never too early to invest in building a strong culture, and it’s (almost) never too late to right the ship.

How to Apply This to Your Business

Just like the seven virtues of entrepreneurship are meant to be practiced and improved, the seven sins are meant to be avoided.

I hope that by explaining them, I’ve helped you spot at least one or two things that you could stop doing today that would make a big impact on your business, no matter where you are in your journey.

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From “aha” to “oh shit”, we’re sharing everything on our journey to $10M in annual revenue. We’re learning a lot and so will you.

About the Author

Alex Turnbull is the CEO & Founder of Groove (simple helpdesk software for small businesses) who loves to build startups and surf.

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