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.


You Have to Jump First

jumping off a cliff

Startups are founded by people that make the leap before anyone else. If you don’t leap first, you don’t stand a chance of winning. Jump. It’s up to you.

No one else can jump for you or before you. If you’re waiting for some form of validation from existing co-workers, family or even worse, investors, you’ll be waiting a long time. You have to jump first.

Julien Smith gets right to the point in his post about making things happen. I’ll add some context from an investor-perspective (not just mine, but from what I’ve seen with others as well.)

You can’t go to an investor and say, “I’m going to leave my job, just as soon as I get funding. Then I’ll do it.” I don’t know of any investor that’s going to write you a check. That’s like telling your girlfriend that you’re going to leave your wife, honest … you’re just working out the details …

Bullshit.

You have to jump first.

Every so often someone asks me, “What are you looking for in an entrepreneur?” It’s a complicated question, and more often than not it comes down to a gut feeling, but when you see someone jump first, that’s a very good sign. Those that are just looking over the edge, but staying on solid ground, or even dangling a foot off the edge, tempting fate, don’t count.

You can’t expect investors, business partners, employees or anyone else — even a co-founder — to take a leap of faith with you if you’re not willing to do so first. Reid Hoffman said that launching a startup was like jumping off a cliff and building the plane on the way down. Tons of risk. Insane. Total madness. All true. Well, maybe … but I can just as easily argue that there’s absolutely zero risk. If you believe in yourself then you can always survive, get a job, initiate a backup plan … whatever. Sure there’s an opportunity cost to starting a company, but the opposite is true as well.

You have to jump first. No one else can do it for you. And no one can push you over the edge of the cliff; well they can, but it doesn’t work well, because chances are they forgot to give you the materials and tools to build your plane. Splat.

Jump. It’s worth it.


The Death of the Business Founder

The commonly accepted structure for startup teams is one business founder and one technical founder. Theoretically it makes sense: one guy builds the product and the other sells it. But it’s not that simple.

Some time ago I wrote that founders can’t live in silos. If the business guy doesn’t get the tech side and vice versa, it can lead to a host of problems. Having spent the last few months talking to entrepreneurs, I’m going to take my concerns one step further and say that the business founder is dead.

We’re seeing more and more startups built by two technical co-founders. That doesn’t mean they can sit by themselves in the dark and code all day and night. Quite the opposite. But technical people are becoming more and more savvy on how to build their businesses. They’re learning about and actively figuring out things like customer development, viral loops, user acquisition, marketing, etc. They’re taking over the responsibilities of traditional business founders but remaining close to and active with product development and code.

The value of a classic business founder without any technical know-how is dropping significantly. That might change when a company hits product/market fit and is ready to scale, but early on, startups are succeeding without pure business founders.

The “new” business founder is someone that gets technology and can build products. It’s someone that can hack together a WordPress site with landing pages for A/B testing. It’s someone that gets analytics. It’s someone that can be in charge of product management (not “project management!”) Either traditional business founders need to acquire these skills ASAP or get out of the way, because technical founders are moving into these domains aggressively. And they should: technical founders need to understand, embrace and excel at these elements of the business.

When you think about your startup and you’re asking, “Who will speak to customers?” it shouldn’t be an either-or question between two founders. Both founders should be speaking to customers. Both founders should be conducting early customer interviews. And when you’re asking, “Who will be involved in designing the UI, product flows, hacking the MVP?”, the answer is everyone.

The traditional business founder is dead. But that doesn’t mean that startups can focus on technology and ignore business. Quite the opposite. Most risk in startups today is market risk, not technical risk. The key is that the people identifying the market risk, problems to solve, market opportunities, customers, acquisition tactics, pricing, etc. are the same people that should be building the solutions. Everyone in a startup is a business founder. Everyone is a technical founder.


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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The opinions and commentary on this site are mine and mine alone. They do not necessarily reflect the opinions or positions of my employer, GoInstant.