10 Ways I F**ked Up My Startup (& How I Fixed Them)

Zero To €100k Revenue In 12 Months — Month 10

It’s time to stop feeling guilty, quit working 18 hour days and give yourself a break!

I’m going to reveal the 10 biggest mistakes I made to help you avoid making them. Even writing them now some of them seem so incredibly obvious that it is embarrassing to write. At the time it can be difficult to remove yourself from the situation and see objectively.

Wrong Way Sign

1. You’ll take it personally

Yep, you will fall into that trap. Because at the start, it is personal. Deeply personal. It's your idea, your risk, and your reputation. As the business progresses you’ll find a way to separate yourself from it as you hire staff and other stakeholders in the business but in the beginning, it is as personal as it gets.

The trick here is to work like it’s personal but try to detach yourself at some level from the negative feedback or criticism. That will only serve to demoralise you if you take personally. Positive and negative feedback is vital to improving but learn to identify what is positive feedback and what is someone venting or complaining without evidence or solid reasons.

Solution: Maintain outside interests that are completely separate from your business. Sports, hobbies, meeting your mates, whatever gets you out of business mode for a few hours. It helps keep your identity separate from the business and also helps you switch off.

Business not personal.jpeg

2. Stop feeling guilty

There is very low external social pressure when working for yourself. This means, you don’t have to be at your desk at 9am each morning. However, it also means there’s no one to tell you not to work 18-hour days.

Being self-employed requires more discipline than any job ever will. If you start taking it easy, the negative results won’t be immediate like in a real job, but they will come. When they do, they will come with a magnitude of 10x.

“The first principle is that you must not fool yourself and you are the easiest person to fool.” — Richard Feynman

This is a two sided coin. The mistake I made here was working crazy hours and continuing to do that long past the point when it made sense to do to. You are going to put in an unhealthy amount of hours at the start of the business. There is no avoiding that and if you are passionate about what you are building, you will want to put in those hours. The key lesson is to find some balance. Don’t neglect everything else in your life.

Solution: Be ruthless with your time management. Plan your week in 30–45 minute segments and stick to it. Avoid task hopping as this creates a firefighting mentality of swapping attention to whatever grabs your attention at that moment.

3. Lonely

Yes, its damn lonely. We are social creatures and the loneliness can have a negative impact on you, your decision making and your business.

Think about your normal day job. You go to an office filled with other people. You might eat breakfast in the canteen and take a coffee break with your work colleagues mid-morning. There are organised events and team meetings. You need to find a way to replace that as an entrepreneur.

The temptation is to shut yourself away and furiously build your startup. While that mentality will get stuff done, it will also create a vacuum for new ideas and positive outside influences.

Solution: Make time to meet people. For me, I meet fellow entrepreneurs, friends, and clients regularly to ensure I am forcing myself out the entrepreneur bubble. For the first 18 months in business, I cut myself off completely from the world. That strategy is counter productive as the people you meet can propel you forward quicker than you can on your own.


4. You will be broke (for a while at least)

Getting a business off the ground will stress your finances at the start. I’ve written how much a founder can expect to earn in the first year here.

The first year is tough, even if things go extremely well. During my first year, the business was cash generating from month 1. That is rare so you must prepare for that. Even though my business was generating cash, I felt a massive burden of expectation and pressure.

Working for yourself is the quickest road to creating wealth but its not a linear path.

Solution: Save at least 1 years worth of salary, if possible, to ensure you aren’t under extreme financial pressure. This should remove any rash decisions you might make that will bring short term financial reward but longer term, do damage to your business.

5. Hard Choices, Easy Life

Birthdays, holidays, parties, you will miss them all through bad choices or through the sheer demands of work. Unless you are out of the country due to work commitments, there’s no need to play the martyr and miss important events. Don’t be a dick!

Solution: Try find a balance in the early days otherwise, it’ll become a self fulfilling prophecy. “I’d love to go but I’m too busy”. No, you probably aren’t. Get more efficient about your workday and be incredibly strict with yourself.

hard choice.jpeg

6. If you have money to solve the problem, you don’t have a problem

I made this mistake repeatedly for the first 18 months. I would spend 3 hours doing something that I should have paid someone €8 to do for me. Silly. I would run all over the city collecting laundry and dropping it off to clients. In hindsight, it’s funny but at the time it put me under massive personal stress.

There are so many websites that you can use to outsource tasks such a design, writing, finance, to even going to collect parcels. I’ve used UpWork for design and found some really great contractors. You can also try TaskRabbit, and 99Designs.

Solution: Print the phrase in italics below and stick it to the wall beside your desk. I’m not advising spending money without knowing the cost. To truly understand your worth, calculate exactly how much an hour of your time is worth. Lets say it’s €16. Ok, now if you have to collect laundry or supplies and can pay someone €8 to do that, it’s simply a no brainer. You are making €8 by simply outsourcing that job.

“If you have money to solve the problem, you don’t have a problem”

7. One man band

There’s generally two traps entrepreneurs fall into here. The first, are people don’t take the time to learn their own business and do the dirty work. They hire lots of staff even when not generating a profit.

The second trap is the one I fell headfirst into.

For the first 12 months, I worked totally solo. Apart from my girlfriend helping me when I was double-booked or friends who stepped in to help me in a few emergencies, I did everything. 24/7 for a year. You can see where this is going. It was awful, inefficient and it was small minded thinking.

Put yourself under pressure for too long and you are not giving yourself time to think. By taking back your life, you’ll avoid growing to resent the business you’ve created.

Don’t major in the minor. (Don’t become so obsessed by the small thing in front of you, that you miss the giant opportunity to your left or the train coming right down the tracks towards you)

Solution: Once you are generating a positive cash flow and profit (most importantly, profit), you should hire someone to take the pressure off you. It’ll have a very positive impact on your business. Instead of being a slave to it, have a second pair of hands will allow you to step away and see your business from a fresh perspective.

8. The Yes Man

You will say yes to every single opportunity that comes your way. I was so delighted that the phone was ringing that I took on some absolutely ridiculous jobs that made me zero money. However, at the start, this is something you will almost need to do as it has two benefits. First, it’ll teach you really quickly what works for your business and what is just a time drain. Second, it teaches you the inner workings of your industry. Think of it as paid learning.

Sometimes you’ll take a job that turns out to be a massive time drain. Just learn from it, do it to the best of your ability and move on. Don’t dwell on it or allow it to make you angry or resentful to your customers. You took the job so just get it done and move on.

Solution: The trick here is to know when the time is right to start saying no to the wrong kinds of opportunities. That is the tough part. It comes back to what we discussed above, you must know how much an hour of your time is worth and then work out if the opportunity is worth it.

9. I didn’t document my journey

This is probably my biggest regret. There are so many rich details and great stories that I’ve simply forgotten as I didn’t keep a regular journal or even make a video diary each week.

So why didn’t I? Fear. I was afraid my business wouldn’t work and I would look ridiculous for documenting my failure. It is easy to look back now with rose-tinted glasses and say I’d have learned something from that too, and I would, but at the time, I was consumed by fear.

Writing this Medium series has given me the chance to understand how valuable the process of documenting is.

Solution: Keep a daily or weekly journal. Write down the mad/interesting/funny/mundane things that happen to you. Trust me, what seems memorable now will have slipped your mind in 3 months time.

Halfway though writing this Medium series, I realised that video & voice will form a much bigger part of my ongoing content creation. I’ve listed some channels below to help you get started.

For longer form videos use Youtube, or document in realtime using Instagram Stories. Voice continues to rise in popularity and I’ve started using Limor, a social audio platform.


10. Ignore your rivals

At the start, I was spending time watching my local competitors. I was trying to see what they were doing and if I should be too. Total waste of time.

I realised what a negative use of energy this was when I received an angry email from a local competitor. He was furious that a newspaper article had called my business “the first Airbnb concierge service in Dublin”. He couldn’t contain his anger and I found it hilarious. He was spending his energy and emotion worrying about me, so I vowed to spend mine building an even better business.

Another one of my largest competitors in Dublin engages in repeated tactics to target me and my customers. They run Google Adwords campaigns against my company using my business name as a keyword. They even ring my office posing to be new customers to try find out some insider secrets. I wish I had that much free time but I’d definitely spend it doing other things!

Solution: If you have time to engage in petty rivalry with your competitors, then you are running a shitty, inefficient business. You should be focusing on your customers and profits. I meet the owner of a similar company to mine almost weekly for coffee or lunch. We discuss the industry and share recommendations for new software and tools. It’s a much better use of my time than engaging in negative tactics.

Winners focus on winning, losers focus on winners.

Winners focus on winning
Gary Foxlessons