Author Interview: Insights: Reflections from 101 of Yale’s Most Successful Entrepreneurs


The Value of Preparation

Roger McNamee

Co-Founder, Moonalice,

Co-Founder, Elevation Partners, Silver Lake Partners, Integral Capital Partners

Co-Founder, The MoonTunes Project, Reverb



Many entrepreneurs discount the value of preparation in disrup-tive technology startups on the theory that if you are inventing a new world, you are better off approaching it unfettered by precon-ceptions. Some investors have stopped backing companies with ex-perienced teams, believing that disruptive change comes most often from first-time entrepreneurs. That was certainly true with Micro-soft, Oracle, Google, and Facebook, but the other side of the ledger includes tens of thousands of companies that crashed and burned because of inexperience.

What is the best way to begin an entrepreneurial project? If you are not a domain expert, become one before you start. Domain ex-pertise gives you an edge in identifying product or business model changes that customers will value. It also enables you to “make new mistakes,” rather than repeating ones that have been made by oth-ers. Once you identify your opportunity, then you have to figure out whether or not you are capable of executing the strategy. This re-quires self-awareness, which is not as widely distributed in the entre-preneurial population as one would hope. At this early stage, uncer-tainty has value, as it provides an incentive for greater preparation.

Then comes the moment of truth. You’ve got your idea; you have a plan for making it happen. Should you do it? My rule of thumb is to sleep on it for a few nights. When you awake, if you can’t imagine doing anything else, then you are good to go. If you can imagine anything at all that you would rather do, bail out from the start¬up. It’s not the right thing for you. Remember that startups are harder to unwind than a marriage. If you make the wrong choice, you will be stuck with it longer than you would like.


Tell us about this story.

In May 2012, I was at a crossroads. I was just about to graduate from college, and I was faced with the challenge of taking a more traditional job (a guaranteed salary and benefits) or attempt to take my newborn startup, TouchPoints, to the next level. In the process of trying to decide, I reached out to successful entrepreneurs from my alma mater for advice and to learn about their stories. The feedback and mentorship I received was incredibly powerful and I wanted to share it with everyone who was interested in starting their own business or organization.

The publishing industry has become increasingly accessible, and because of the entrepreneurial spirit of this book, I decided that the best way to share what these mentors told me was in a book. INSIGHTS: Reflections from 101 of Yale’s Most Successful Entrepreneurs is exactly what the title says it is – a collection of the best advice shared by successful entrepreneurs of my alma mater.

What living person do you most admire? 

I’m going to sidestep the question and say the living person that I’d most like to have dinner with is Elon Musk.

What is your most prized possession? 

It has to be some piece of technology. I have things that are sentimental and meaningful, but what possession could I not do without? Let’s go with my iPhone. I can Facetime with loved ones, text friends living all over the world, run a business, take a library of books with me anywhere I go, and spend what little remaining free time I have on Instagram.

Which talent would you most like to have? 

To be a legitimate coder. I think everyone should have a basic understanding of a coding language. Rails and Python should be the new Spanish and French for high schoolers all across the country.

Who is your favorite fictional character of all time? 

James bond. He’s been alive for over 60 years, and his style is still setting trends. He’s smart, classy, optimistic, and tech savvy.

What’s your idea of perfect happiness? 

Happiness to me is giving the perfect gift to someone you care about.

If you could change one thing about yourself, what would it be? 

I wish I could function on less sleep. There are too many good books to read and too many places to see in a lifetime.


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