12 Common Ways You’re Sabotaging Your Startup and Your Life (Stop These Immediately)

Please, stop wasting your potential.


Sabotaging your startup is like crack, except that it won’t get you high. What it will do, is it will bring you down.

And as with alcohol and any other drug, we get addicted to it, and only realize its impact when it’s too late — team members leaving, investors not doing another round, customers not buying anymore, you spending 10 years of your life on nothing.

It’s a pattern of actions that can, if you’re not careful, result in something much worse: 90% of startups fail (I’m in that 90%.)

In general, it’s extremely challenging to recognize the signs, figure out what causes it, and resolve it. Often, it’s a pattern you don’t recognize until someone else spots it for you.

That’s not to say you’re the one whose fault this is. It’s root cause often lies outside out sphere of awareness at first.

What’s crucial, though, when your startup’s failing or just not really satisfied with how things are going, or feeling your passion turning into indifference or experiencing uncertainty a bit more often than you’re used to, is to do one thing:

Take control of your startup’s trajectory.

Or, seeing as you never control 100% of the outcome, as much control as you can.

You owe it to every potential customer you can help, every team member, every partner. But most importantly, you owe it to yourself to stop sabotaging your startup and being the one who’s in control of where you’re going.

The startup world is fucked enough — there’s no need for you to make it more shitty by making a bunch of thickheaded decisions.

Your startup is like a human body. You need to diagnose it once in a while, maintain it and do repairs where necessary.

In this article, I’ll explain what I’ve seen the most successful entrepreneurs do to move their startup from startup to thriving business.

Let’s dig in.

Disclaimer: I failed my own startup and am no successful entrepreneur. I actually messed up all of these, but especially point 9. Because of that, I can’t tell you how to be successful. What I can do is tell you which things will kill your potential.


1. You Don’t Build Habits

We often think success happens overnight. The question I get asked a lot is: “What can I do to go from zero to income ASAP?”

Even though it’s a great question to understand how to build a business in principle, it assumes one thing that’s quite dangerous: that success can happen in an instant. The truth is: It hardly ever does.

We want immediate results. We want meditation to turn us into Buddha within 20 minutes, we want a diet that cuts our weight in half within a week, we want an app that brings us the love of our life in the next hour.

But nothing is going to change for you tomorrow. Meditation doesn’t work tomorrow. But meditation works. Your habits won’t change your life today, but habits do help us improve and do help us get better. And that is what in the long run makes them work.

So the question shouldn’t be what you can do to make that success happen right now, or tomorrow. Rather, the question should be how you can organize your life so that your goals will be be a result from all of your continued action.

Solution: Step one is to take your time to read this article. Then come back here, and ask yourself: How can I build habits around all of these?

2. You Don’t Take Care Of Mental And Physical Health

When you buy an expensive car, you take care of it. You make sure to change the oil once in a while, you check the brakes, you take the car to the garage to get your engine maintained.

And the truth is, you’re probably taking better care of your car than of your mind and body.

I mean, people already knew this in the third century BC. Herophilus, a contemporary of Euclid, said:

When health is absent, wisdom cannot reveal itself, art cannot manifest, strength cannot fight, wealth becomes useless, and intelligence cannot be applied.

That health is physical and mental.

Physically, you’re probably not drinking enough, not getting enough sun, not moving enough, not eating enough vegetables, drinking too much and smoking too much.

Mentally, you’re probably not getting enough rest, online too much, not being present enough, not having enough fun, not learning enough, not in the flow state enough, and not spending enough time with your loved ones.

Solution: Simply take one of the things you’re not doing enough, and try to create one habit each month (challenge: each week) that helps you build better mental and physical health.

3. You Don’t Start At The End

Have you ever heard the story of Alice in Wonderland? It’s a story about a young girl that ends up in a strange world called Wonderland. One of the moments that’s most telling is where she encounters a fork in the road. Here, she meets the Cheshire Cat, and the following conversation takes place:

Alice: “Which road do I take?”,
Cheshire Cat: “Where do you want to go?”
A: “I don’t know”
CC: “Then it doesn’t matter.”

The point is: it doesn’t matter what you do, if you have no idea where you want it to lead you.

Research has found that most successful founders are driven by where they want to go: their vision of making a positive impact. What that vision looks like? Basically four factors:

  1. What trends currently have a strong influence world?
  2. What will the world look like in 5 years?
  3. What problem has a huge impact on a huge group of people?
  4. What role do you want to play in solving this problem?

Solution: Spend time determining what the end-point looks like, and then reflect upon this every 3 months.

4. You Don’t Question Assumptions Enough

Is your target customer everybody? Is the world full of evidence in support of your ideas? Are your tactics and strategies not leading to enough growth? Guess what: you’re suffering from Innovation bias.

Somehow when we get new ideas, we only see potential. We see all sorts of problems and needs that we can solve. We only see the evidence supporting our ideas.

These assumptions overwhelm us with optimism, which in turn kills our ability to think critically. Without thinking critically, we lose perspective of the actual risks and figure out how exactly we can realize our dream. (You know this if you’ve started your business for the first time.) Resulting in… you guessed it… an epic product launch!

Without any customers.

Solution: Print out the picture below and hang it on your wall.

Did that? Great!

I take every Friday to write down my assumptions about how my new ideas might work, and then determine which ones are the riskiest (likelihood I’m wrong (1–5) * impact on business if I’m wrong (1–5).) Then I start experimenting with them.

For an example of how I do that in the early stages of a startup, read this piece.

5. You Don’t Empathize Enough

People have a subjective view on the world, have goals for what they want to do in that world, and have problems achieving those goals. Your role as an entrepreneur is to understand your customers’ worldview, figure out their goals and solve their problems.

Put differently: your role as an entrepreneur is to create something that makes their experience in this world a bit nicer. That’s why people buy from you.

But how can you create something of extreme value for someone if you cannot imagine the world their eyes?

How are you going to buy an awesome birthday gift for someone you don’t know?

How can you build something valuable for someone when you don’t empathize with them?

Right, you don’t. And that’s why 42% of startups fail: because they didn’t create value for someone real.

Solution: Seriously… Talk to customers. Be curious. Make a connection. Spend time with them. Customer interactions are you way to strike gold and becoming the best you can be. Don’t make the mistake of not doing it.

If you want to know how to do that, you can read more here.

6. You Don’t Fail Enough

When you’re in an uncertain situation, the last thing you want is doing another thing that’s uncertain. I understand.

That said, did you ever try something and not seeing it work? Like writing a blog and not having it read? Or launching an app and not seeing anyone use it? Some people call it failure, I call it learning.

Paradoxically, improvement at whatever comes from a loop of trying, failing, learning thousands of time. And, not so paradoxically, your success, it so happens, directly follows your improvement.

Solution: So stop over-preparing. You’re keeping everything to yourself, and basing your decisions on your own assumptions. Shift focus from ‘I want to be right’ to ‘I want to maximize my learning.’ Ship yesterday. Publish last week. Try today.

7. You Try To Boil The Ocean

Startup news is filled with Apple going beyond $1T, some scooter-sharing platform raising $600M, Elon starting a teleportation company (fake news.) I get it that you feel like you’re going to be the next change-maker. But honestly, that’s just the fast lane to being discouraged, before burning out in general. The path from zero to hero isn’t one step, it’s a million small steps. So don’t try to boil the ocean.

Solution: Start small and simple. Boil one drop. Figure out how that works. Then boil two. Learn. Then boil a glass, a bole, etc. Break your complex and overwhelming “world-domination” down into manageable (this word is important) chunks, and start on the first one.

8. You Think Business Is Busyness

The data is out. Working 24 hours a day for 7 days a week makes you miserable and kills you. All that time you’re mindlessly emailing customers, micromanaging the team, writing code for hours, keeping investors updated with weekly meetings, looking for new investors, talking to new employees, basically doing everything? It’s killing your potential and satisfaction with what you’re doing. You’re not working towards building a business, you’re working towards an extremely busy freelancer with some helpers.

Truth is: your time is worth something, but you’re spending it foolishly. We would never hire someone whom we know doesn’t do the work. We wouldn’t buy a train ticket to a train we know won’t go. We wouldn’t invest in stock we know is going to crash. Somehow, though, your time has another standard. We don’t think about the output we’re creating versus the input it requires. The only question that matters is: did I create enough value for the time invested?

Especially as founder, your job isn’t to be busy. It won’t get you what you seek. Your job is to create value. That’s it.

Solution: 1) Measure your input against your output. (See point 1.) 2) Think about alternative strategies to create the output you’re seeking, then compare input and output. 3) Analyze the moments you’re waiting for someone or something. 4) Figure out whether your input/output ratio differs per strategy, then figure out why and focus on those that create maximum value. 5) See the next point.

9. You Don’t Build (The) A Team Around You

Like me, I know your parents have probably been telling you you’re the best. And I’m sure you are a force to be reckoned with. But what happens if your company grows from 2 customers to 200,000?

If you want to grow beyond a freelancer and into a business, you simply need to move away from working “in” the business to working “on” the business. This means you need other people to be working “in” the business. People who focus solely on engineering, product, sales, HR, business development, communications and marketing (not in that order specifically.) Then, you can use your time and energy and start to actually be productive.

Solution: Organize your business so you’ll have so much time left that you’ll have no idea what you should do with it. Figure out how you create value for your customers, then figure out which positions need to be filled, make a list of people you want to fill it with, and go talk to them. There’s no need to hire them right away if there’s no money, but seeing as time is of the essence, it’s best to get them in the loop ASAP.

10. You Don’t Hold Yourself Accountable

Humans are raised and trained that if we do badly, someone’s going to pull our shirt and tell us we’re sucking.

When you didn’t clean your room, your mom told you to get your shit together. When you didn’t study for the test, your teacher gave you a 1 (yeah or an F if you’re in America I get it) — and your mom’s going to nag your even more. When you didn’t deliver your project before the deadline, your boss complained, and if you continued not delivering, she fired you — and your mom didn’t like you sleeping on her couch.

But for an entrepreneur, there’s no one to keep you accountable. There will be no one to say “Hey, you’re doing terrible. Stop doing a terrible job.” In the early days, the only ones to do that will be your customers. But they won’t use those words. They’ll simply not buy.

There will only be a lot of signals for you to draw that conclusion. But if you’re not keeping yourself accountable, you’ll miss them and you’ll continue sucking.

Solution: Get in the habit of assessing your progress. See point 3: start at the end. Write down where you want to be in a year. What do you need to achieve in the coming quarter, in the coming month, and the coming week. Then every end of the week, reflect on whether you made that goal, and why you did or didn’t. This way, you don’t need your mom to tell you you should get your shit together.

11. You Don’t Think Effectively

Most entrepreneurs make bad decisions because of these three biases:

  1. Preparation bias: Do you ever think ‘If I only add this one extra feature, the market will be super happy?’ or ‘I need it to look better before shipping it’? Yeah, that’s killing your progress. We get stuck because we don’t think about where we want to go, what we need to learn, and how we can best learn that. Perfectionism is hardly ever (I dare say never) the way forward.
  2. Innovation bias: You’ve got all these amazing ideas, and people will love them. Except, often they don’t. That’s because we come up with problems around our ideas, that might not actually be grounded in reality.
  3. Overconfidence bias: That data you find that doesn’t support your idea, that’s not significant. Right? Wrong. But I get it: you’re an entrepreneur, so you’re naturally extremely confident and optimistic that this doesn’t mean anything. Until it does.

Solution: Reverse these three biases by doing the following:

  1. Prioritize learning over perfection. Let you customers tell you what works and what doesn’t, and then improve.
  2. Get out of the building. Be grounded in reality. Use actual data from the real world. Assume less. Test more. Talk to real customers.
  3. Be your worst skeptic. Work like Google X. Look for things that don’t support your idea.

12. You Think Scale Is Always More Important Than Profit

Are you getting ahead of yourself? The answer is probably yes, but you have no idea you are. And that’s not your fault. Because consensus for startups is this:

Raise a lot of money at seed, grow your revenue, raise more money at series A, rinse and repeat through series B-G, then IPO or exit. You basically focus on raising cash so you can spend that cash so you can raise more cash so you can sell the business for cash.

In the real world, that doesn’t actually work. Research found that for 1,100 companies raising seed, only 89 managed to exit for more than $50M. Only 5 exited for over $1B. So that doesn’t really work.

Why? Because if you raise funding, it’s more important that you grow your customer base than it is to important your unit economics (profit). It’s more important to grow from 1,000 to 10,000 customers with a negative margin (i.e. losing money on each customer you’re onboarding), than it is to figure out a way to create a positive margin and then scale acquisition.

But there’s nothing wrong with building a real business that’s profitable. There’s nothing wrong if you acknowledge that using startup as an excuse for not making money is actually ridiculous. There’s nothing wrong with shifting your attention from growth of revenue to growth of profits.

Solution: The most important thing to figure out first is whether you can get costs lower than revenue at scale. Measure your performance metrics (to start, it might be a good idea to measure what and how you’re earning, what and how you’re spending), and then figure out how you can improve them. Once you’ve nailed it, you can scale it. You can then focus on scaling up hiring, customer acquisition strategies, and new product features.


Did I do all these things in my own startup? No way, Jose. I sucked. But I’m working on sucking a bit less every day. At the same time, I’m helping other entrepreneurs flip these negative practices into positive ones, and seeing it make a world of a difference. They become aware of their strengths and weaknesses, and know what they have to do to grow. They go through their weeks feeling a bit more in control. They can engage in deeper conversations with meaningful people again. And sometimes, even the small improvements are all we’re looking for. The results won’t come in a day, but the small victories will lead to a happier, more stable, and more successful business.

Your startup’s potential is much higher than you think it is, and if you can master its trajectory you’ll be able to appreciate what you’re working on, the possibilities it offers, and the major impact you can make for others.

Follow your dreams, and put in the work.


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