How to Have Startup Swagger Without Being a Complete Asshole

You need a sizeable ego to succeed in the world of startups and venture capital. Without that ego propelling you forward it’s going to be hard to wake up every morning, take the risks you need to take, and aggressively go after what you want. You won’t be able to negotiate from a position of weakness but make it seem like a position of power. You won’t be able to motivate others around you when things are crumbling. You won’t be able to power through 20-hour days and execute like a maniac. This is true for startup founders and it’s true for investors. A healthy ego is important.

I think of this as “startup swagger.” Every founder needs it and has a right to it. After all, starting a business is a big step – one that few people ever take – and that alone gives you the right to be proud. Unfortunately, swagger can be taken too far.

Founders and investors need startup swagger, without crossing the line into the domain of assholes.

Lately, I’ve been getting quieter. I’m rarely the most talkative in meetings, although that wasn’t always the case. There’s something to be said for sitting back, listening, and only speaking when you really want to make a point. I want to be more thoughtful and patient, but at the same time don’t want my voice going unheard or getting lost in the noise.

In thinking about startup swagger and assholes, I want to share some ideas on how to manage a healthy balance between the two:

  1. Listen more than you talk. Filling the air with words for the sake of it is a form of pollution. Perhaps less harmful on the environment than CO2, but still…
  2. Stop name dropping. I get it. You know a lot of VIPs. Me too. So what? If those VIPs aren’t materially helping you right now, I’m not particularly interested.
  3. Share your past achievements. Don’t hide your past experiences and successes. Chances are you’ve got something special to share, so do it. Just don’t bash me over the head with it.
  4. Be ambitious. There’s no shame in wanting to succeed, and succeed big. Be ambitious with your plans. Feel free to tell me that your startup will be worth $100M someday. Ambition and passion are a must for any startup founder (and frankly for any investor too.)
  5. Be humble. Don’t go overboard aggrandizing your expertise, network, success, etc. There’s a good balance to be had between talking a good talk and recognizing when enough is enough. Someone once said to me (re: pitching & presenting to investors), “Don’t act like the smartest person in the room.”
  6. Actions speak louder than words. The best way to impress people is to make things happen. Big things. And small things. Crazy audacious things and the nitty gritty that just has to get done. It’s pretty hard to talk your way to success, actual work needs to take place. But at the same time you can’t hide in a corner and work by yourself quietly and expect people to care. You’ve got to make sure people can connect you to the work and your accomplishments.
  7. Don’t be lackadaisical. When given the opportunity to present your startup, do it and do it right. Respect people’s time and put in the effort. You never know what value you’ll get out of the experience.
  8. Speak with purpose. People who speak clearly, loudly (but not too loudly) and appear engaged (think: good body language) are always going to garner more respect than those who speak quietly, mumble and slouch.

I’ve hesitated for over a week in publishing this post. Normally I write something, go through a couple edits and hit publish. In this case I’ve been waiting and thinking it over a lot. And it’s been nagging me; I actually get grumpier when I have writer’s block and don’t publish content at least once per week. Then I read The Top 10 Types of Douchebags in Tech and How NOT to Be One and decided to publish the post. So there you have it.

Don’t be an asshole. Feel free to swagger and put on a good show. Make sure you always deliver, and be cognizant that there is a line you can cross that’s hard to go back over again. Once people see you as an asshole, it’s hard to change that perception.


Lying to Yourself is a Leading Cause of Startup Failure

Although I did complete a Psychology degree at university, I’m no psychologist. And I’m no self-help guru either. But the more I think about startups and entrepreneurs, the more I think that one of the leading causes of startup failure is lying. Not lying to other people, but lying to oneself.

People lie to themselves all the time. We’re so good at it we do it subconsciously. We bury the truth so deeply that it doesn’t come out until the walls are crumbling around us and our bank balance is bloody red. We mask the truth and apply a heavy reality distortion field.

But here’s the thing: We have to. Entrepreneurs have to lie to themselves. I don’t think we could get through it if we didn’t. The level of uncertainty entrepreneurs face is extremely high. We’re asked to make decisions on a constant basis with partial information and little experience. We need to sell a vision and a dream as much as reality, which is in essence a lie. We have to get up every day after being punched in the head and keep going. We know the odds of success are slim, and yet we keep going. When an entrepreneur succeeds it’s almost always because of drive and passion (luck and timing play a huge role too!) Drive and passion are there to mask the truth.

And yet, I think too many people lie to themselves too much. As a result, too much passion, drive and enthusiasm is pointed at the wrong things. Entrepreneurs stick with zombie companies too long, get burnt out beyond recovery, bang their heads against the wall until they collapse, make critical mistakes … all because they’re lying to themselves. And they believe their own hype. Positive feedback is wonderful as long as it doesn’t overly reinforce an entrepreneur’s lies. Reason, judgement and strategy are thrown out the window so quickly when things are going incredibly well or bad, in large part because the lies we’ve ingrained in ourselves either propel us to false heights or buoy us against disaster. Lie too much to yourself and your startup has a very good chance of failing.

Somewhere there’s a line between a necessary amount of lying and too much. I’m not quite sure where it is, but I’m keeping myself on alert, so I don’t delude myself beyond reason.


My Three Words for 2011

I don’t know if Chris Brogan started the meme or not, but every year he publishes 3 words that will serve as his guiding pillars for the year ahead. Last year I didn’t publish 3 words; instead I stuck with one: Freedom. Looking back at that post from the beginning of 2010 I can reasonably say that I did find more freedom last year than in previous years. At least in some ways. I’ve also taken on more projects than ever before.

2011 is going to be a big year.

Here are my 3 words for 2011:

Create. Accelerate. Win.

Create: I’m an entrepreneur at heart. And I live to create things. I have to be careful not to create too much and take on more than I can handle, but this year is all about wiping the slate clean and starting new things.

Accelerate: It’s time to move even faster. No one is waiting for me (or anyone else), and the old adage is certainly true, “If you want something done [right] do it yourself…” I can’t sit on the sidelines and expect things to happen. And I want to accelerate everything I’m doing, and help others accelerate successfully as well.

Win: I want to win. I want to win big. I want to win all the time. Winning is good. I know I’ll lose once in awhile, and I’m certainly going to stumble and make my share of mistakes, but I have no problem planting the proverbial flag in the sand and saying, “I want to win.” That’s not ego talking, it’s drive.

Create. Accelerate. Win.

The year is long. There are always ups and downs, emotionally uplifting moments and plenty of emotionally draining ones as well. As they say in hockey, “It’s a long season.” And during the year it’s hard to maintain momentum (or in my case, acceleration!) – we get tired, sick, beaten down, angry, sad, frustrated… But humans have an amazing ability to take a kick in the teeth, get back up and do even better than before. I want to maintain that inspiration throughout the year by using create, accelerate and win as my 3 words for 2011. Do what you need to in order to buffer yourself against all the craziness of life and get ready to kick some serious ass. Maybe it starts with 3 words of your own…


About Ben Yoskovitz
I recently joined GoInstant as VP Product. GoInstant changes how we use the web, making it shareable like never before.

I'm also a Founding Partner at Year One Labs, an early stage accelerator in Montreal. Previously I founded Standout Jobs (and sold it). I'm a hands-on startup guy, helping companies grow successfully from the idea forward. You can reach me at byosko at gmail dot com.

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