Why crime bosses are hot or How to become a pirate

Posted on January 23, 2012 by


Well, not all of them are hot. But think of the real bad ones. Those with the money. With charisma. With muscles and posture. Those who know what they want and get it. Those from the top of the food chain.  Still doesn’t sound familiar? Never mind, as this is neither going to be an empirical analysis of evolutionary attractiveness, nor a woman’s confession. This post is about … leadership! And you will understand the connection soon.

Emily already reflected about startups from the employees’ perspective. Now, I’m going to switch to the “leader’s” perspective. Why is good leadership in startups important? What are the goals of a startup leader?  How does a good leader get stuff done? And what about those crime bosses?

Beyond Nerdyness

In my last post about the mentality of startups I revealed that the personality, mentality and attitude of an entrepreneur are strongly related to success. Matt Ridenour from Momentum Venture Management confirms that many people with “good ideas have good academic pedigrees, professional experience and technical skills, and yet very few of their ideas ever make it to market”. The reason for that is not that they lack motivation, don’t like risks or that they don’t get the funds. According to Ridenour the missing ingredient is good leadership! He remarks that getting entrepreneurs to think beyond their technology can be challenging.

Think of it as a city…

“Budgets are a mess and job growth has been minimal for a good swath of the country. Cities in need don’t just need strong leadership, they require transformational leadership. It’s no easy feat but it’s likely that the more that mayors view their cities through an entrepreneurial lens, the better they will be able to adapt to a rapidly-changing world” illustrates startup-advisor Jon Bischke on Techcrunch. Apart from that, cities or areas like Silicon Valley or Berlin have to attract talented young people and avoid their emigration in bad times. The same conditions are true for startups. An entrepreneur needs to see the whole picture and “understand how to navigate the unique and challenging path that start-up ventures need to take”.

Lessons from a crime boss

I doubt that reading another manual is going to make the next good startup leader. It’s about experience, states Ridenour. So why not benefit from the experience of others?  Here’s what Donald DeSantis learnt about startups from a crime boss, the kind of guy I referred to above.

  1. Think big: The bigger the market you address, the lower your marginal risk. And he must know since his transactions were likely to be more risky than those of a “normal” startup.
  2. Cut out the middle man: Cut costs. And who knows, you might even be able to capitalize your intermediate product.
  3. Don’t screw with your users: That’s why DeSantis stays true to his visions and protects his customers from greedy investors.
  4. If it don’t make dollars, it don’t make sense: Have a viable business plan before proclaiming the next big thing.
  5. Ask for it or take it: Fortune doesn’t fall into our laps.
  6. Be a badass: “If we want to captain a pirate ship, we must become the most badass version of ourselves”

DeSantis claims that’s all he needs to know.

The pirate ship’s crew

To keep your crew on your ship under all weather conditions I just found another list on Gründerszene about how to motivate your employees. Feel free to read it. To make it short: Emily illustrated the advantages for people to work in startups. Now, the leader has to emphasize those and be a charismatic and strong example.

Have you met any pirates?

As for many things in life, there doesn’t seem to be a universal method of how to become a good leader. Fact is, leadership is important for startups and has to focus on different challenges than other enterprises, such as higher speed, a less defined course and a crew that won’t fall overboard. Leadership also implies experience and I liked DeSantis approach of learning from a crime boss because I have also had the sensation that sometimes sources of learning  are where you least expect them and that sometimes someone you would have given a wide berth turns out to be a great mentor. What was your most unconventional source of influence?