Max Power & Calculating Your Confidence


In Homer to the Max, Homer Simpson stumbles upon a television show character by the same name. After the character goes through a negative transformation, Homer gets ridiculed for being associated with such a person. In an effort to overcome this, Homer legally changes his name to Max Power. Garnished with compliments about his new identity, Homer embraces it. Improving his image by shopping in high-end retail and befriending the affluent Trent Steele, Homer has convinced himself that his new name improved his lifestyle.

Hubris was Homer’s real identity change. Which may not be as negative as it sounds.

Being overly-confident helps you set and achieve goals that were otherwise unthinkable and seemingly unattainable. Being realistic in your challenges can undermine your ability to meet goals. If you realistically viewed your challenges, there is strong possibility you’d never attempt to overcome them. Allowing yourself to overstate your own abilities can be beneficial in taking a risk you may not have even considered.

Jason Zweig, in his book Your Money and Your Brain, writes that 81% of entrepreneurs gave their own businesses a 7 to 10 chance of success. 33% of entrepreneurs say there is zero possibility their business would fail. Zweig goes on to note, “roughly 50% of new businesses fail within their first five years”. This shows a huge dissociation between perceived success and actual success. Being overconfident in their abilities and challenges allows them to deceive themselves of their own probability of success. Without this mindset, we may have been without such unicorns as Uber or Airbnb. Disrupting the taxi monopoly would have been unthinkable without a dash of over-confidence in Uber’s success. Airbnb was a failing startup before rocketing to success. Confidence in these projects success kept them afloat

Using this knowledge in your daily tasks may not be as reckless at it seems. Calculating your overconfidence is the key to avoiding failure. Do this by asking yourself such questions as: When can I take on more risk to push a project to succeed? When can I tell myself this will not fail (and if it does, not be destroyed along with it)? Being overly-confident can push you over the hills of “It won’t work” and “It’s not feasible”.

In the end, Homer eventually goes back to his original name. I’ll attribute this to a necessity of having the episode end where it started, rather than a lack of confidence.


HUBgrown: Q&A with Michael Skok


Boston is booming with new thinking, interesting people and revolutionary companies. Many businesses are born here, thanks to the city’s renowned institutions and incubators, accelerators and other startup programs around the greater Boston community. While some grow up and move on to other places (hey, Silicon Valley) we believe there’s something unique about companies born and bred out of our great city.

In this new series, HUBgrown, we’ll explore what makes Boston’s business scene one-of-a-kind. That means insights from local entrepreneurs; investors that can predict which companies are going to make it big; and, media dedicated to the Boston innovation scene.

We also want to hear from you along the way. Have a question you want to ask one of Boston’s thought leaders? Share it with us. Know someone that is doing something cool but hasn’t shared it? Tell them to speak up. Something bugging and/or exciting you about the state of entrepreneurship in Boston? Let’s hear it.

For our first installment of HUBgrown, we spoke with Michael Skok. Well-known in the city as an entrepreneur, investor, mentor and educator at Harvard, Michael talked to us about why Boston’s rich history has a significant impact on the culture and what makes entrepreneurs successful.


HB: In your Startup Secrets workshops, you discuss company formation and how important culture is to hiring. How would you describe Boston’s entrepreneurial culture?

MS: Boston’s culture was born out of its first settlers. There has always been a great sense of dedication and persistence  here that you don’t find in every city. This differs from my experience in Silicon Valley, where the culture was all about the next shiny and new thing. In Boston, hard work and loyalty in particular really stand out.

HB: Do you prefer the Boston tech scene to Silicon Valley?

MS: I strongly believe that there is no wrong or right culture, there are just intrinsic differences. In Silicon Valley, you can’t go anywhere without being touched by technology and a wide open sense of possibility. It’s built into the fabric of the area. In Boston, we have a strong tech scene, with less critical mass but more rich diversity with the arts, sciences and academia.

HB: How do these differences attract entrepreneurs to Boston vs. other cities?

MS: Because Boston is a city built on such substance, entrepreneurs here are focused on solving long-term problems, not just building the next trendy app. Change doesn’t happen overnight, but the entrepreneurs here know that and are focused on what’s going to have the most significant impact, not just the quickest return.

HB: You frequently write about how in order to pursue and solve big problems, you need to learn to tap into your internal energy. Can you share a specific tip for how entrepreneurs can accomplish that?

MS: It’s simple. Look at what makes you unique and build on it. What one person experiences in life is completely unique to their upbringing and life experiences. We have all come from different places, have different backgrounds, interactions, perspectives and understanding. As an investor, I’m always looking for people who are uniquely qualified to address the problem or opportunity they are going after. There’s no one answer, so start this self-discovery by separating your experience from your ability, attitude and aptitude.

Tap into your own experience, look at what you have to offer and what you love and focus on what you really care about to find your genuine passion. And be authentic and honest with yourself. The saying, “Fake it ‘til you make it,” is bullshit. If you’re faking it as an entrepreneur, you’re not tapping into what makes you unique. Your customers and team will also see through it and you’ll ultimately fail.

HB: Can you give an example of an entrepreneur you’ve worked with that successfully tapped his/her own energy?

MS: I think all the good ones I’ve worked with do this. I specifically screen for it when I’m investing. I don’t back ideas, I back people who see problems they’re uniquely qualified to solve and have the resolve to execute. Boston has many such entrepreneurs such as Paula Long, Dries Buytaert, Brian Halligan, and Jason Purcell to name just a few that I’ve enjoyed having share their stories in my Startup Secrets workshops. And I have a very long list I’d like to back, including more and more great women entrepreneurs like Ellen Rubin who are going to make their mark.

HB: What has been your defining moment as an entrepreneur and an investor?

MS: I love the question. It makes for good one liners. But for me, it’s been a learning journey, with no one defining moment. I often say the older I get the more I realize I have to learn. So if anything, I’ve learned that it’s best to keep evolving and change perspective so that you keep curious and frequently question answers. That’s also why I try to teach with frameworks rather than answers. I want the next generation to come up with their own, new and better answers. The problems of tomorrow will not be solved by the answers of today.

And in this regard our next generation of young entrepreneurs have a major advantage. They aren’t prejudiced with experience. Instead they’re unbounded and therefore free to try everything and learn from experimentation that can lead to breakthroughs. That’s why I love working with students and young entrepreneurs. They’re just starting out and have limitless potential to realize the opportunities in front of them.

At least what I hope to do is help remove any barriers to them realizing their full potential so they can dream big, tap into their passion and realize their potential with the focus and persistence it takes to build something really meaningful and valuable. Here’s to that being a Boston made difference we make.

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