Why you probably didn’t get my Mass Challenge Endorsement

A year ago a truly amazing startup competition was created, Mass Challenge.  Basically its an opportunity for startup companies to compete for $1 Million dollars!  The $1M is split up between a handful of startups (16 last year), but the really crazy part is that they take no equity.  The competition is broken down into multiple rounds of judging, eliminating entrants at each checkpoint.  In my opinion the 100 startups who make it to the “Final Round” are the real winners.  These teams will get 3 months of:

  • Amazing free office space in Boston (right on the water)
  • Endless mentoring & feedback from tons of successful entrepreneurs
  • Tons of exposure and access to great connections

But what I really want to talk about is one specific aspect of Mass Challenge – “Endorsements”.  Endorsements are this awesome part of the competition that help make it more real.  Essentially there is a list of entrepreneurs who are heavily involved in the community and are open to volunteering/participating in the competition.    These entrepreneurs can chose to “endorse” a company competing in Mass Challenge.  An endorsement can lower a teams entry fee, but more importantly it shows the judges that they are influential and “getting after it”.  I love the idea of endorsements because I really believe that the entrepreneurs who are the most well connected, get out there the most, and truly engage the community are the ones most likely to succeed.

Now lets fast forward to present day….

Mass Challenge releases the list of endorsers, which i am part of.  In the coming weeks I receive well over 40 emails/tweets asking for my endorsement.  Admittedly I was a bit turned off by some peoples approach and wanted to outline where I think they went wrong.

MassChallenge #Fail

I cant tell you how many emails I got that started like this:

Hey Jonathan,

My name is _________ and I’m the co-founder of  __________.  We entered into MassChallenge this year and I had noticed your name on the list of endorsers.

Would you endorse us?  I have attached our pitch, and here is the link http:// masschallenge.com/endorse.

Thanks so much!

There are just so many things wrong with this email.

The fact that “I am on the list” is not even kind of sort of a reason for me to support your startup.

Can you imagine if someone cold called you and said “ Hey, I was looking in the White Pages and noticed that you had a male name.  Being a guy and all I figured you liked baseball, did you want to buy season tickets to the Red Sox?”

Now how about this….

“Hey, I work with the Red Sox season ticket office.  I had noticed from time to time you tweet about the Celtics, and it even looks like you might have season tickets there?  Either way, in my experience we tend to see a lot of overlap in people who like both sports teams!  Had you ever thought about season ticket to the Sox?”


If you had Google’d “Jonathan Kay Grasshopper” – you would find over 2 pages of interviews, blog posts, and random content all about me.  Did you try visiting about.me/jonathankay?  The point is, I am very public about who I am and the things I enjoy…if you took the time to learn about me and find some commonality or way to relate your startup to something you read….you would have had my endorsement without even a second thought.

More than my endorsement, you would have also had my support.

You need to be considerate of peoples time

I want to be involved in MassChallenge…its why I volunteered my time.  But at the end of the day, I have a full time job at a startup company and it can be very demanding.  The quicker you can get me to buy into your value add, the more likely (and willing) i will be to endorse you.  If I have to spend 5-10 minutes reading an executive summary every time someone emails me asking for an endorsement, it will most likely end up on the list of thing to do “when I have a minute”…which unfortunately is kind of a black hole.

Spend 5 minutes instead of 30 seconds.  Spamming doesn’t work anymore

Sure, if you create a basic email template (insert the appropriate name based on email address) and send it to everyone on the MC Endorsement list you can probably knock out 250 emails in an hour.  But how many responses do you get?  Does anyone really read about your company?  Do you create any contacts or mentors?  Isn’t that what its all about?


I challenge you instead, to spend 3-4 hours sending emails (you are an entrepreneur after all right? Sleep isn’t important).  Learn about the person you are reaching out to, make it personal, and show them you actually care.  I would bet that even though you only send 60-75 emails, you get nearly twice as many actual supporters.

I want to end with a quote that very much drives how I live my life and do my job:


“Traditional marketing has companies speak to many to reach one.  Today we speak to one to reach many.” – Andy Sernovitz



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9 Responses to Why you probably didn’t get my Mass Challenge Endorsement

  1. Yana says:

    people’s time*

    Anyway, you know how I feel about this sort of thing so I am obviously not your target audience, but wanted to support your blogging endeavors by commenting : )
    In fact, if course I am into anything that helps entrepreneurs succeed. I’m also into introducing myself in short and personalized emails. This kind of have-to-tailor-my-deck-to-investors-and-god-forbid-i-make-it-interesting pack mentality is one of the things that drive me insane about the start up world. Also the term “value add.”

    By the way, this is quotable: “you are an entrepreneur after all right? Sleep isn’t important”

  2. This is a great example of best practices. You have explained exactly what endorsements are all about!

  3. Elliot Nash says:

    Solid post man. Its kind of like natural selection of the startup community and weeding out crappy entrepreneurs.

    • jk1459 says:

      Thanks man. I love that by the way…”Natural Selection – Start up Style”. Thats pretty much how it works in the “real world” anyway…the companies who engage and pay attention the most tend to be those that have the best chance of succeeding.

  4. First, I’m envious of the Boston scene! What a great program that can benefit so many young companies.

    At the same time, that is quite an inconsiderate result! In my experience, every moment you spend meeting other entrepreneurs who are willing to give their time to support their community comes back so many times over. And it’s easy! It’s like making a friend. That’s a lot easier than building a real business, in my experience.

    At any rate, keep dropping science JK!

    • JonathanKay says:

      Thanks for the comment Jim…and don’t be envious, you are doing quite a kick ass job with the Charlotte community! I have to say though, I could not agree more with your Friend Analogy. I treat most of my business contacts like friends, and I find the relationships tend to be much more memorable.

  5. Punit Shah says:

    I’ve found the most effective pitches for an endorsement are by entrepreneurs who get an introduction. They are even better if they ask me a question based on my past experiences in startups. It shows the entrepreneur is doing their research, and looking to learn from the interaction rather than solely gain an endorsement which ultimately wont take them past judging at MC. Love the quote by the way!

  6. CMF says:

    As an entrepreneur in the MassChallenge this year, I totally agree! Why people would cold-spam for endorsements seems a total waste of time (yours and mine)! Each one of our diamond endorsements came through personal contact (or through a recommendation from a personal contact). http://tiny.cc/fu7m9z

    But what I really want to know is how you skipped right over to the end of the week (blog reply is dated MAY 4!!!) . . . and since I am an entrepreneur, can you reverse that trick, cuz really could use a few more days in the week (as well as some sleep)!

  7. Jonathan, we at MassChallenge whole-heartedly agree with your view on the MassChallenge endorsement process. Thank you for taking the time to explain the benefits this process was intended to provide to the entrepreneurs.

    We agree with your suggestion that entrepreneurs should spend the time to learn about the person they are reaching out to, with the goal of making a personal, relevant request. And we appreciate the help you are providing to the entrepreneur community.

    Regrettably, MassChallenge should have done a better job of explaining this ourselves. The result is that many of our entrants did not understand the process. We are looking at alternative ways to communicate the value of the endorsements in the future.

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