What are 16-things you need to avoid in order to be a successful entrepreneur

What are 16 things you need to avoid in order to be a successful entrepreneur?

So often founders look for tips and magic bullets to be a successful entrepreneur. Successful people are the worst to learn from, there is often luck involved (of course, not always. Respect the hustle). What worked for one person might not work for you.

The reality is there are so many things you can do, it can be easier to focus on what you shouldn’t do.

We are going to cover 16 things you should not do if you want to succeed as an entrepreneur.

There are a few things I need to get across first:

  1. There are NO shortcuts on the path to success. Startup is a marathon and you need to put in the work each and every day so it compounds. Compounding is a crazy powerful thing
  2. I’m going to tell you things you should not do, but you are going to ignore them. You will refuse to internalize them. You have to experience your own stupidity to learn really internalize things. All I can hope is you become aware of these negative aspects and when you catch yourself doing them, you think “Alex told me that. I can see myself doing it now. I need to fix it!”

16 points for you to ignore in order to be a successful entrepreneur 😉

1/ Don’t join a company to learn how to do startup first.

Every time an aspiring founder asks for advice about setting up a company, I always tell them the same thing. This is from my own hard gained experience.

  1. Join another startup first
  2. Pick the quality of the founder over the startup idea
  3. Join as early as possible- get on the ground floor
  4. Work your ass off like you are the CEO already (without crossing boundaries)
  5. Talk to every person in the company, regardless of the department and get them to teach you how they do their job. Try to get them to give you the templates they use, the schema for SalesForce, anything you can get! You can reuse this when you start your company
  6. Make the CEO your mentor for when you startup

There is so much to learn as an entrepreneur. You need to know something about every department that you have.

Join another startup and blow their resources learning. Just do it. Trust me. You are a total retard right now. You haven’t earned an opinion on anything.

You will learn so much about what to do and what not to do so that when it’s your brand and your investor relationships on the line, you will be all the more better for it.

Ok, assuming you have a startup already, the rest of this advice will apply to you.

2/ Pick a small market.

The market always wins. Pick a BIG market. The same effort that it takes to build a company for a large market applies for a small market (you just have a bigger budget, more department heads etc).

Think about it, you will always be poor if you are selling offshoring strategies to hippies in a commune with market size of zero.

‘Small market’ depends if you are building a bootstrapped or funded company.

  • Bootstrapped: If you are building more of a lifestyle business, a hundred million dollar industry is fine if you can take a few % of it. If your profit margin is high enough, you can still make millions a year, which isn’t bad 😉
  • VC funded: If you are doing the VC thang, then the market size is imperative. Min is a bill, you ideally want something greater than $5b. Why? You can’t be a huge company unless you have a huge market. VC math is different to founder math.

In any case, if you find a sexy underserved niche, make sure the market is large enough for you to meet your financial goals. If you have 100% of a $1m market you can only ever make $1m.

3/ Hire dumber than you.

What is an excellent startup?

It’s a team of excellent people doing the right things. Excellent people do the right things at the right time.

When you hire dumber than you it is what Jobs called a bozo explosion.

  1. A hire A (And it stays like that)
  2. B hire C
  3. C hire Trump…

A lot of people who have an ego or suffer from imposter syndrome consciously of subconsciously hire people dumber than them so they aren’t challenged and never look stupid.

Stupid is as stupid does.

Please hire the smartest people you can possibly find, can afford, and frankly manipulate into joining you.

Next, hire slow and fire fast.

Everyone ignore this advice. I’ve done it too because I needed stuff done, but they just made more mess.

If you only hire people that know more than you do and make you look like a retard, you will make money. You won’t do it until you learn for yourself.

4/ Solve a problem no one cares about.

So many techies have tech looking for a problem. It’s called a solution looking for a problem.

The entire blockchain and crypto space is a case in point.

Aside: I was talking to a new friend in NYC who does DD for VCs on crypto and he said there are probably only 3 quality projects in the whole space. But they refuse to lie to investors so they are horrifically underfunded.

It does not matter:

  • How awesome your ninja team is
  • How large the potential market is
  • How awesome your tech architecture is
  • How awesome your solution is
  • how much funding you have…

If you are not solving a problem people care about and want now.

They just will not sign up and your CAC will be horrific.

You need to solve a problem people are willing to pay for as they have a real problem. This is all that matters. The bigger the problem, the shorted the sales cycle (which is key for enterprise companies).

5/ Don’t accept feedback/be humble.

sit down
(Hol’ up lil’ bitch, hol’ up lil’ bitch) be humble
(Hol’ up, bitch) sit down
(Sit down, hol’ up, lil’ bitch)
Be humble (bitch)
(Hol’ up, hol’ up, hol’ up, hol’ up) bitch, sit down
Lil’ bitch (hol’ up, lil’ bitch) be humble
(Hol’ up, bitch) sit down
(Hol’ up, hol’ up, hol’ up, hol’ up) be humble

– Kendrick Lamar

Girls, investors, staff, etc. Everyone loves humble people. Think Keanu, the obsession du jour.

No one likes an arrogant know it all that refuses to listen to anyone. Think about the people that you like the most… they’re the ones that let you talk and actually listen (to your ideas).

If you want to be loved like Keanu but are actually an egotistical tyrant, then fake it and secretly call them a twat in your head. But keep up the facade. It’s called being a sociopath. Be like Bateman.

Always take feedback from your peer founders and your staff, frankly everyone in the company you started. You hired them for a reason, right? Even the hotty you hired to look hot in reception has insightful views about your insta game, right? (What do you think she does all day?)

The staff that is most likely to leave are those that don’t feel like their opinion matters and that they do meaningful work.

Finally, if you want to have a toxic workplace, start blaming others for all your fuck-ups. You will cultivate a blame culture where nothing will really get done.

You need an environment of better to ask for forgiveness than permission and don’t blame those people if they tried their best. I promise you they will never take the initiative again. Staff needs to feel safe to make informed risks and you need them to. Otherwise, guess who is going to do all the thinking?

You. Thinking and work are overrated. Get smart people to do it for you ;).

6/ Don’t pick up the phone.

I know that we all live in WhatsApp messaging with each other. Hell, when is the last time you called a lady to ask her on a date? Like, 2004?

I’ll let you in on a secret, the phone works. It worked for my father and it will work for you.

I was having A chat with my friend about his father’s accountancy business. his father wasn’t the world’s greatest marketer and largely relied on the Yellow Pages as everyone did back in the 90s and 80s. Sometimes he would lose clients and we need to make it up and order to gain the financial Returns that he needed to maintain himself, so he would always just do one thing. He would pick up the phone find numbers for businesses and start calling them.

If you are ever in doubt about what you should do you should pick up the phone and make a call.

Pick up the phone. Do sales.

7/ Don’t know the job you are hiring for.

A great recipe for disaster is not knowing the jobs and the roles of each and every person in your company. As the CEO you need to know the basics of every department that your company operates full stop if you launch a new customer success initiative then you need to know how customer success works in order for you to understand the KPIs and effectiveness of the people in your team. How do you know who to hire the head of customer success if you don’t even know the job that they do?

If you want to be a s*** CEO, then stay in your ignorance and just hope someone else we’ll figure everything else out. Look at Elon Musk, he learned to be a rocket scientist by talking to people and studying books. he could have just had some people to hopefully figure it out but he did not leave it to that kind of chance, he wanted to understand the rocket business.

For the vast majority of people in this world, there is one thing that costs the most fear in their Souls and they want to avoid as much as possible. it’s called sales full stop if I were a betting man I would say that 99% of people would love to not have to do sales at all of possible and just hope they hire someone and they will figure it out. that is total and utter b*******.

The person who is going to be doing sales up and to the point where you can’t handle doing any more sales calls and meetings is you at the CEO. you need to know how to sell your company, you need to know what resonates with prospects and how to close the deal. when you’re getting To series a you think you’re just going to hire a VP of sales and that will magically be it full stop that’s not the way that it works you need to know how the sales process works how to handle objections in order to be able to teach your new VP of sales how to do their job. it is only after a period of time at which point you can let the VP of sales ride with things.

Until you know how to sell your own company you cannot and should not hire someone to do sales for you.

If you want to hire someone for a job you need to understand the job.

8/ Stop learning every day.

One of the key requirements to be the CEO of a start-up is that you have a passion and commitment to learning each and every day. you need to constantly up your game and get smarter. if you are struggling in the very nascent stages of your business you are suddenly going to hit a brick wall when you need to start scaling at your series a comedy series b or even at your growth rounds. 

If you do not commit to learning you will suddenly find yourself replaced as the CEO. Frankly, if you have vested shares should probably be grateful for it because that CEO will actually do a proper job. 

But why does the new CEO do a better job than you? Well, no one was known was born knowing how to be a CEO. at the person who replaces you learned faster and worked harder than you did in the previous years.

There will always be a never-ending requirement for you to learn. Buy books, get a mentor, hire consultants to teach you how to do things, do whatever it takes and however you learn in order to get your learnings.

You need to learn like a machine learning model with a continually improving labeled data set.

9/ Be in a shit mood.

Your attitude and how you interact with staff as the CEO matters.

As CEO you don’t realize the impact you have on staff. It took me a long time to realize this.

I’ve shared this story many times before because it matters, so I’ll share it again. (You can read about this here, CEOs impact the productivity of the office with their attitude)

When I was running a company I often was stressed by working too much and frankly getting up in the morning is not my favorite thing in the world. at one point one of my juniors came up to me privately and said to me that I need to get my s*** together because my attitude was negatively impacting the staff on the floor. When I come in a bad mood and I’m tired everyone knows it and it impacts the entire attitude of the whole office. I never quite realized this myself and it was quite profound. I knew I needed to make a change

I then would have two cans of red bull and four fags before I walked into the office after working all night. I then would high five people. When I was in a bad mood, the office reflected me. The staff looks to the leader.

To be a successful entrepreneur, your job is to help others achieve their best and you can’t do that when they are walking on glass.

10/ Buy into your bullshit.

At some point in your startup’s life, you’re going to have some level of success. there is a tendency for certain types of people to them want to buy into their own fame and basking their glory. this then leads them to negative cognitive biases when they believe that they are the chosen one.

Amoruso at Nasty Gal bought her own PR. She was too busy jerking herself on book tours etc to care about her business. She built an insane business off her passion and hustle and is an inspiration. But she blew it on her ego.

Again, stay humble.

11/ Set up construction sites:

When I was building a start-up I was trying to get a lot done because it was a complete show and so many things need to be fixed. I was multitasking and multitasking is bad.

I would often have 5 to 10 projects ongoing with different people executing on things that I had to keep on top of.

One day a colleague came up and had a chat with me about what I was doing. He said “it’s great that you are trying to accomplish all these things but what have you actually s***. What’s actually in production and finalized. you need to pick one thing and just get it done and ship it. what you’re doing is creating construction sites. There’s a lot of things happening there is a lot of activity but I think is really actually getting done?

I was creating construction sites. it would have been better if I just picked one or maybe even two things and make sure that they got done in a shorter time period so the company could see the benefit from it immediately and compound from that.

12/ Be a perfectionist:

Perfection is the enemy of progress.

In a start-up done and good enough is the definition of perfection. You frankly just don’t have the resources to ever actually do things perfectly, so don’t even bother trying.

the most nefarious kind of product is the one where you think you know exactly what the customer wants and try and appeal to every single potential Avatar of customer that there is and results in feature bloat with a totally impossible to use the product because there is far too much in it.

Wanelo in the early days had built a fully-featured product and it failed to get a lot of traction, so what they did was take the large decision to completely redo the product and only had in one or two features and then put it out into customers. Once they listened to customers as to what they wanted they would then add the exact features and no more than what was required to meet the needs. By doing this they started taking off like the proverbial rocket ship.

Often less is more.

13/ Procrastinate:

If you do not like getting things done and want to put things off then a startup is not for you.

If you’re working in a dead-end job and a recruiter is trying to get in touch with you but you can’t really be bothered to talk to them in order to get that job you want, so you might call them tomorrow then that is not making progress.

A startup is about making progress each and every day and just getting things done. as a startup, it’s like lighting a match and seeing the flame study burn down.  you are about to get your fingers burnt.

To be a successful entrepreneur you don’t have time to procrastinate. 

14/ Don’t delegate:

As everyone knows there is never enough people and time to get all the things done that are needed in a start-up. As the founder of a company, you cannot do everything yourself.

Your job is literally to tell the people you hired what to do and offload all the work. Whenever something needs to be done you need to think whether or not you can delegate it, or if you are the only person in the company that can?

You can’t delegate pitching investors, you can delegate getting a Perfect Pitch deck.

If you do not need to do it then you need to think who is the best person to execute that given the workflow that they have.  whilst they may not be able to do things as perfectly as you, but done is better than perfect as we have discussed before.

If you have hard quality people and they want to take on more and very tasks and so frankly been delegated to so long as it is not cleaning the toilets is something that they actually want.

So delegate till they break and focus on what you need to.

15/ Burnout:

Startup is a marathon not a sprint.

You really do need to think about your health and well-being full stop Richard Branson constantly tells people that he gets an extra 3 hours a day by spending an hour in the gym. He is just so much more productive because of it.

I’ve come close to pretty much totally burning out the fourth and I can tell you what is not pretty. what do you basically feels a sense of ennui and you do not want to face doing anything. looking at emails it’s just something that you just do not want to do. Do not get to this place.

When you can afford to you need to take a holiday every now and then. of course as a CEO you have to be available on the phone for emergencies but you still need to take a holiday.

When you can afford to you need to start taking weekends off and enjoying life so that you remember while you are working your ass off to build a start-up.

16/ Chase distractions:

There are only so many activities which are going to deliver the big results for you. They are called Pareto activities. They are the ones that deliver 80% of the results for just 20% of the effort (Learn about the Pareto law here).

If you are a later stage company and have a relatively large audience and functioning business model then you can start thinking about doing business development.

If you’re not a large company, and that de facto means 90% of all other startups out there, that I have a big piece of advice for you.

Don’t do any business development unless that’s key to your business model (you need APIs etc).

If you get an email from a big company like Twitter or Facebook, simply respond “it is an honor for you to reach out to us but we are focused on building a product right now we would love to be in touch with you in the future”.

Congrats, I saved you about a full-time equivalent of 2 weeks.

What the fuck Alex? Are you serious?  Facebook just reach out to us isn’t that amazing!?


  • Business development deals take a long time to happen and you don’t have the resources for them
  • Assuming the deal actually works out incredibly well then you probably don’t have the scale to facilitate them
  • They are lying to you. You think that you’re going to get access to their massive resources of uses, but in reality, all they give a s*** about is getting your users. Unless you have a lot of users you’re going to end up having a bunch of pointless meetings that will never actually close with anything. If you have enough users for them to be interested then they’re going to structure up a deal where they’re going to benefit and you’re going to get nothing out of it

Business development in the early stages of a start-up is a total and utter waste of time. It’s a distraction.

The main thing is to keep the main thing the main thing.

Conclusion on what to avoid to be a successful entrepreneur

That’s some advice. I could write more, but frankly, if you are able to internalize these and ‘hopefully’ implement one or two ot them you will have a shot at being more successful.

What do you think about these? What would you add in your experience?

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