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How to Have Startup Swagger Without Being a Complete Asshole

April 8, 2011 by Ben Yoskovitz

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.

Filed Under: Personal Development

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Ben Yoskovitz

Founding Partner at Highline Beta, a hybrid venture studio and VC firm that works with large, ambitious companies to identify new areas of opportunity through internal and external innovation.

Previously I was VP Product at VarageSale and GoInstant (acq. $CRM), and Founding Partner at Year One Labs.

Angel investments include: Breather, Spoiler Alert, SendWithUs and others.

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