So… young singles who live with their parents make better entrepreneurs?

In order to increase your entrepreneurial success:

  1. Stay single (or get a sugar mama or a sugar daddy)
  2. Don’t contribute to the gene pool
  3. Live on your parents couch to avoid having a mortgage
  4. Stop celebrating your birthdays do you don’t ever turn 30.

I am kidding of course. However, I didn’t fabricate the above list entirely on my own. I just interpreted someone else’s take on entrepreneurial a tad bit differently. This is my first post of a series of posts about the Duke MBA EVCC’s recent Week-in-Cities trip to San Francisco.

Our first stop was at FlightCaster, which is an Internet start-up that uses advanced algorithm to predict the probability of flight delays hours before the airlines can. Jason Freedman, the Founder and CEO, had great insights to share on what it takes to be an entrepreneur. Before I share his views (mixed in with my own thoughts and humor), here’s a brief summary of FlightCaster.

According to Jason, FlightCaster raised $1.3 million in Series A financing back in November 2009. I can assure you, as an ex-consultant who once logged ~150,000 miles in one year while experiencing many frustrating flight delays, FlightCaster’s service is invaluable.

FlightCaster may not make much sense for the casual traveler, but it could save a lot of time for road warriors. Rather than finding out 30 minutes prior to scheduled departure that your flight has been delayed for 2 hours, wouldn’t it be more useful to know several hours in advance? That would give you plenty of time to make alternative travel arrangements and you wouldn’t have to fight with 200 other passengers for that last seen on another flight.

Jason received his MBA from Tuck, but I can forgive him for that since he did his undergrad at Duke.
Here are some traits of an entrepreneur according to Jason (Consider this an entrepreneurial aptitude test for yourself).

An entrepreneur is:

  1. Determined and is willing to fail. Start your first business as soon as possible. Failing could be a good thing if you learn from it so start your first company and fail. Get it out of your system. Then go start your successful venture.
  2. Good at hiring. Jason describes himself as B- person who surrounded himself with A+ people. Check your ego at the door. Find people who are smarter than you and hire them.
  3. Skilled at raising capital for his or her company. Raising money is similar to selling. Build a brand for yourself so you can sell yourself, your team, and your concept. This goes back to #2. You should be able to sell your vision to your team to keep them motivated.

He also offered some practical advice for those who are curious about entrepreneurship or are just starting down the Internet start-up path.

  1. Join the start-up conversation by reading: Hacker News, Tech Crunch,, Feld Thoughts,, and Both Sides of the Table.
  2. Become known by blogging and tweeting (and try to build a following of 1,000+)

On a more humorous note, he warned against the “drag factors” that can often hinder entrepreneurs (see the connection with my list above?). This is probably more relevant to MBAs than college students.

  1. School loans
  2. Spouse
  3. Kids
  4. Mortgage
  5. Over 30

Jason is not suggesting that one can’t be an entrepreneur if he or she has these so-called drag factors. It will just be more difficult to not give up when you have too many obstacles. I only have 1-2 so I think I am okay. 🙂

By: Jonathan Lee
Twitter: @hi5at5


2 responses to “So… young singles who live with their parents make better entrepreneurs?

  1. Hi Jonathan,While I admire what Jason has accomplished and any insight from his experiences, I would have to disagree with some of his advice. Experience and a personal life are not obstacles. Having a family does not mean that you lack commitment or are distracted. I couldn’t imagine going through life with that mindset. Yes, there are examples of successful, young entrepreneurs in the Silicon Valley, but there are even more young, inexperienced entrepreneurs who realize that they are in way over their heads and need help from more seasoned entrepreneurs. You can be a successful entrepreneur without sacrificing a life that includes a home, family, and aging. Andy Rachleff of Benchmark Capital, Scott Weiss of IronPort, Jeff Bezos of are a few examples, to name a few.What was Jason's advice about the importance of getting 1000+ Twitter followers? He has 125 followers.What was his opinion about the value of an MBA for entrepreneurship? There are many entrepreneurs out there without MBA's who would argue that the degree is worthless. If Jason didn't have an MBA, would he say the same?Like you said, I’m sure this would be an inspirational talk to someone who’s in his/her 20’s and missed the tech bubble (and its aftermath) 10 years ago. I totally would have bought this back then. I’m now more inspired by people who prove you can have it all.

  2. Liz,Thanks for your comment. I really hope I didn't misrepresent Jason. He was generous with his time and we really enjoyed meeting with him.I think Jason was being humorous with some of the things he said. What he was getting at is that, in general, having more responsibilities makes it difficult for you to take greater risks. For example, I know I can't start a company right after I complete my MBA because I have to put my wife through her PhD program. In other words, I can't afford to not get paid a certain level of income. I am tolerant of risks, but she's not.I see your point and agree with what you are saying. Jason was making a broad statement and urging people to go for it now rather than later when they have more mouths to feed or other financial obligations. He was simply saying that now is the time. 🙂

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