Put a few entrepreneurs in a room and you'll find the topic of conversation will inevitably gravitate to who's done more screw ups than the other. I've been in that room enough times to know that after a while it's the same record all over again. I share with you below the 10 most frequent, which also reflect my experience starting PeoplePerHour:
1. Hiring too quickly
As an entrepreneur you are naturally eager to move fast and build a big business. Not only that but you are by nature impatient, no matter how fast you're moving. That's partly what makes you who you are; and why you don't fit into the normal routine of a corporate job.
Inevitably you make the mistake of hiring someone too quickly that you shouldn't have. Not only that, you hire them against your instinct. That niggling hunch that there's something about them you don't like, but you are conscious of being too fussy, too slow, too much in pain to say no.
Every one of these cases backfires multifold. And in some cases can bring your business to a grind. Just don't do it. Listen to your hunch. Take your time on hiring - it's the single most important investment you make. Do it carefully.
2. Giving too much equity too quickly
Every entrepreneur's been there: needing cash imminently, door after door gets shut in your face, people turn you down, people don't answer your calls; they laugh at your idea; they think you're crazy. Then someone comes along and he's listening. But he's vulture. Only you're so starved that the vulture looks like an angel (hence angel investor) a white knight who's a bout to save you. And believe you me the sense your starvation. They use it to get the most they can. And then you're screwed.
Make sure that however hungry you are you protect your equity. It's the one thing you cant claw back - not very easily at least. Negotiate like a bull even if you're hungry. Frankly an investor will respect you more if you negotiate at tough times eve, they'll know you're tough and have nerves of steel.
3. Not listening to your hunch
I hate regret. I don't normally regret things. But one of the only things I do regret consistently is the times I didn't listen to my intuition. Whenever I did that I always - ALWAYS - regretted it. The founder's hunch is one of the most important assets of any startup or business. It's your compass that guides when all else fails. Its what gets you to shore.
USE IT! And be confident enough to stick by it, to know that if you have this burning feeling in your stomach there is probably a very good reason why
4. ONLY listening to your hunch
Most entrepreneurs are very intuitive people. They are hunch driven. If you think about it you have to be: in the beginning you don't have much else! With time what you need is to complement that hunch with proper management discipline: looking at numbers, KPIs, and formulating strategies and plans that you stick to with some discipline (although remaining nimble enough at the same time). For a lot of entrepreneurs this is nemesis; it goes against their nature. They are used to going in in the morning, seeing what's broken and fixing it. And then the next day doing the same thing all over again. You fix enough things you'll eventually get there (you think)
And the reality is you probably will. But it will be a lot slower, it will be a lot more painful and will be costly in terms of missing out on what is probably the real big prize. You can stumble on a big opportunity, or you can harness your talent to get there systematically.
5. Listening to Outsiders too much
Having outsiders around you - especially smart ones - is a great. It gives you fresh perspective. It helps you step back once in a while and see things fresh. It helps you take a helicopter view of your business. Which is healthy once in a while.
But it can also lead you down the route of destruction if not done with care. No body knows the business better than you do. Remember that. You built the thing. So it's all too easy for some hot shot investor or successful entrepreneur to come along and blind you with their money or success, leading to think they have the magic answer to everything. They don't!
In fact some of the smartest investors and operators talk the best kind of sh*t money can buy! (in many cases that's what got them there in the first place). They're usually are very opinionated, very strong minded and exaggerate every belief they have by a factor of 10. So where they start off a little wring they end up VERY wrong. Make sure you take everything with a pinch of salt
6. Taking things for granted
Especially when it comes to investment; whatever anyone has promised you, whatever they have said, take nothing for granted. Investors have amnesia, and their money will come before their promise to you. They walk in every day and think "what's the best investment I can make today" without any emotional attachment to yesterday. You may have been sh*t hot yesterday, but today someone else came along they're hotter. It may have nothing to do with you, you're hotter than ever. But today there's someone hotter. You lost.
So make sure you have a contingency plan. Make sure you take nothing for granted.
7. Underestimating competitors
The best entrepreneurs are fiercely competitive and they are paranoid like crazy. They watch competitors with very little pride, but with a lot of determination and feistiness; a tenacity to win. The losers are the ones who gloat in their own achievements and end up losing the game. The best ones are those who shamelessly copy competitors or borrow ideas, who have no pride to steal good idea and make them better; who are only concerned with one thing: to win.
8. Not letting go
Most entrepreneurs struggle - at some point or another - of letting go. They are used to doing everything themselves. They are perfectionists and obsessively detailed in some things, while very stand-offish and hands off at others. Those things they find hard to let go of
I must admit a turning point for me was letting go of certain things and hiring great people to take them on from me; people who can do those things better than I could ever do. And then an amazing thing happens: its like a massive weight is offloaded from your chest. You now have time to think, play around with things to find things you otherwise would miss, bond with your team, check out the competition and get the hell out and meet people. Those things are super important not for today or tomorrow but for the future. And entrepreneurs are way too focused on fire fighting most of the time: they sit in their office fire fighting all day, getting sh*t done. Solving problems.
That gets things done today. It doesn't build a business. Get out of there!
9. Working too hard
As a workaholic myself, this may come as amusing statement to many who know me. I work all the time and even when I'm not working my mind is working and thinking about the business.
Yet I've come to appreciate the importance of not working so many hours. Especially if you are a creative person, and that creativity is important to your business. You should get out, do things that get your mind off of work. That's when I get most of my best ideas (of course then I get my phone out and send off an email, so I just spoiled it but at least I got the idea and iPhone versus a BBerry has done miracles there. Much harder to just shoot off an email.)
10. Forgetting to enjoy the process
Last but not least: having fun in what you do is key. Especially if you are the founder. People in your team will look at you and mirror you; some will emulate you. So if you're miserable your whole company becomes miserable. If you're upbeat - well not everyone necessarily is automatically upbeat - but they sure as hell have more chances.
So make sure you enjoy. Building a startup is a experience very few have the opportunity to do in life. Whether you succeed or not, you've already done more than the vast majority of people: which is to get off your ass and do something. To not be afraid. To have the guts to try.