What I learned from my 3 years at Grasshopper

As of a few weeks ago (November 18th specifically), I no longer work at Grasshopper.  For those of you who know me, you know this is very much the end of an era / chapter in my life.  In fact, working at Grasshopper became a part of who I was.  I can’t tell you how many times I was referred to as “The Grasshopper Guy”, “Grasshopper Buzz”, or “Ambassador of Buzz”.

Over my 3 years working there I created what is now known as the Buzz Department.  I was responsible for landing over 550 press mentions, and a handful of very valuable partnerships.  During my time there, Grasshopper was getting over 30% of their signups via word of mouth.  Even more importantly, I would like to think I helped Grasshopper’s brand feel more human and approachable.

One thing is for certain, I learned more in the last three years than ever before in my life.  And yes, that means I learned more at Grasshopper than I did from my 4 year degree at Bentley College, a respected business school (sorry Dad).


In closing the door on this chapter of my life, I wanted to share a few lessons I learned about business with you:


Leadership is Crucial

The founders of Grasshopper (David & Siamak) had a life long impact on me.  They gave me a chance, and empowered me to succeed.  But what do I even mean by this?  I mean in my first 2 months of working there they sent me on a trip to San Francisco to pitch and launch Chargify, at the TechCrunch 50.  I mean when I got home from that trip I had a hand written note in my mailbox thanking me for busting my ass.
I saw David Hauser every morning, why take the time to write me a hand written note and mail it to my apartment?  It’s because he cares.  David and Siamak more than anything, care about the people that work for them.  When that happens, it makes your employees want to go to bat for you, fight for you, do anything they can to make your company succeed.

At Grasshopper it was always more about leading than managing – which is a really important distinction.  I was never told exactly what to do, but rather in which direction to run.  They let me discover my own path, and make my own mistakes.  They made me feel like I “owned” my job, and I worked that much harder as a result.


Do Not Underestimate Word of Mouth

For those that don’t know, word of mouth converts at 20% – Fact (Google it if you want)!  Most websites / marketing channels convert somewhere between 1-2% (if they are lucky).  Word of mouth also tends to have a 75% lower CPA (cost per acquisition) than other forms of marketing.
Wild right?

And most people just write it off as something that “happens”, and there is no reason or logic in trying to influence it.  Its not scalable and isn’t a good use of time.

I call Bullshit.

One of the most valuable things I learned at Grasshopper was the power of word of mouth.  If you find a fun, genuine, and unexpected way to do something kind for someone else, it will absolutely come back around.  At Grasshopper, I started doing things as simple as sending interesting people who tweeted about us $5 Starbucks gift cards.  I did not ask for anything in return, I just explained how appreciative I was of their support.  Do you know what happened over 85% of the time?  Those people tweeted more about us!  Those people then told their friends, family members, and colleagues about us!

It’s important to incentivize & influence good behavior (think Pavlov’s Training for entrepreneurs).


People who play hard, work even harder

From Memorial Day to Labor Day at Grasshopper the entire company took (paid) half day Fridays. That means for about 10 weeks in a row you got to go home at 12-12:30 on Friday.  Just take a minute to think how glorious that is…  The reason I bring this up is because I think its brilliant.  I truly believe that people who play hard, work even harder.  Regardless of if we had a half day on Friday or not, everyone was still responsible for getting the same amount of work done.  But, in this scenario we did it with a smile on our face.  That oil change we were dreading trying to find the time to get done, we easily did on Fridays now.  Half day Fridays made our week that much more awesome, and we worked harder (and happier) as a result.  Everyday our design team played an aggressive game of Wii Golf around 3 or 4 pm.  They probably played for a solid 45 minutes straight, and never felt like they had to be worried about time or that they were going to get in trouble. You better believe those were the same guys still in the office at 6, 6:30pm cranking away.


Trust your employees, give them freedom, and you will get rewarded with awesome passionate work.


Environment & Culture Matter

The more and more I am immersed in the startup scene the more I realize that success is almost exclusively based on the people and the execution.  A big part of that though is making sure you create an environment that allows people to succeed.

In fact I think Dropbox is one of the best examples of this.  They really live the “get out of the way” mentality.  The don’t tell people how or when to work, and their goal is to make their office a place people like to be.  They allow their employees to build their workstation however they want, with whatever tools they want, and there is absolutely no budget.

There is a great Slideshare all about this from their Founder/CEO Drew Houston here.

At Grasshopper, employees are given a problem, not a process.  This allows people to think for themselves, own the project, and get creative.  Not only does this make your employees enjoy their job more, but you actually end up with a much higher quality results as well.

If you are reading this thinking it wouldn’t work and that your employees wouldn’t excel in this environment…you probably have the wrong people working for you.


What’s Next For Me??

I am taking a shot at my dream.  I am in the process of creating my own company called Apptopia.  I have an office in Kendall Square, Cambridge (the heart of innovation), and I am working on an idea I believe with a partner I respect.  Regardless of if I succeed or fail in the venture, I can now say I tried.  I can now say I did everything I could to create something new, and build a company people wake up and get excited to work for.  For me, that is the dream.


So what is Apptopia?

Apptopia is a business-to-business marketplace designed to help facilitate / broker the sale of mobile apps.  Not in the sense that you buy on the App Store, but rather how you buy a domain on Sedo, a website on Flippa, or anything on Ebay.  Our goal is to connect developers who build awesome mobile apps with business minded people that want to purchase, support, grow, and ultimately monetize that app.  For the first time ever, Apptopia is providing app developers with a legitimate exit strategy.


I’m around and always pumped to have a coffee/beer and talk startups, marketing, mobile apps, etc.

Don’t ever hesitate to reach out:

@Jonathanckay and/or Jon (at) Apptopia (dot) com


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The Most Overlooked Lean Startup Principle

If you Google “Lean start up” you get over 11 million search results.  If you were to mention it at any Boston networking event you could instantly find someone who is reading a book about it, someone practicing it right now, and someone who just wants to talk about it.  In fact its become so over taught / talked about that now people are writing books about books that other people have written. (I know that sounded complicated, but seriously…its true)

I mean at this point everyone knows the buzz words right?

  • Fail Fast
  • Eric Reis
  • Steve Blank
  • Steve’s book (that started it all) Four Steps to the Epiphany
  • Customer development
  • Earlyvangelists
  • Listen to you customers
  • Launch early


Over the past year or two I’ve observed that there is one lean startup principle which is terribly difficult to implement and almost always overlooked.

Don’t Be Defensive

When you are starting up a company, creating something, you are putting it all on the line.  And I don’t necessarily mean financially.  I mean mentally and emotionally.  You are taking an idea that you have worked out inside your head and are opening it up to criticism and feedback from the entire world.  There will with out a doubt be some people who think you are stupid.  There will be people who you thought would support you, who won’t.

The stereotypical “Roller-coaster” example exists for a reason right?

And the crazy part is that with this whole movement around Customer Development, its even more necessary than ever to put yourself out there.  In fact, its your job.

There are 2 road blocks that most entrepreneurs will (unknowingly) encounter:

1. They will react defensively to feedback

Its only natural right?  I mean someone is criticizing “your baby”.  But by doing this you will not only not “hear” the important feedback your potential customer is giving you, but you will make the conversation more combative.  It will most likely make the person you are interviewing feel attacked and uncomfortable being completely honest (which is a huge missed opportunity for you).

2. They will look to try and confirm their hypothesis

This is a combination of humans inherently being bad listeners, and entrepreneurs wanting to succeed more than anything else in the world.  You need to find a way to be unbiased and open minded.  The best thing I can think of is to simply check yourself every 2-3 minutes – “What is this person really thinking, am I interpreting it correctly?  Are they really biting?”


I was at a great event last week in Charlotte, NC and watched 4 new startups present their ideas to an audience of 100 people and a panel of 4 very successful entrepreneurs.  After their presentations there was a really engaging Q & A which involved questions both from the panelists and the audience.  Three of the four founders, were consistently explaining themselves and rebutting concerns from the audience.  They kept starting sentences with “Well, I think…..”.

Not one of these 3 founders took the time to simply say “THANK YOU” to the people asking them thought provoking / critical questions.  The audience / panel was giving their real, honest feedback and helping these founders avoid potential obstacles and they never even said thank you?  They were too busy defending themselves.

Even worse than that, none of these guys were taking notes.  I mean I know you are on stage, but shit these people are taking the time to help make your business stronger and you aren’t even writing it down?  If I was up there all I would be doing is saying thank you, asking deeper clarifying questions in response, and writing everything down.


Just to clarify, the point of this post is not to teach you something, and certainly not to provide a lesson in psychology.  I was inspired to write this simply to raise awareness around a problem I believe is hurting entrepreneurs chances of succeeding.


I hope at the very least this post will make you think twice next time someone is giving you feedback.

Good luck out there.

**For those who really aren’t familiar with what customer development is all about, feel free to email me directly or leave a comment below and I will send you over some good links / material to get started**


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Why I Wont Pay For (or attend) FutureM

I would like to start by establishing a few facts:

  1. FutureM is a week long mashup of events in Boston designed to spark discussions around the “Future of Marketing”.  It attracts a diverse audience as event topics range from marketing, design, development, media, mobile, to simply general entrepreneurship.
  2. FutureM is Boston’s attempt at creating a South by South West (SXSW) like event / environment.
  3. This is FutureM’s 2nd year.
  4. I participated in FutureM last year both as an attendee and as an event organizer (I helped organize / spoke at 2 events, and attended 3-4)
  5. FutureM was free last year, and costs $100 this year.
  6. If I wanted to attend my company, Grasshopper, would absolutely no questions asked pay for my ticket.

Last year when I heard FutureM was coming together I immediately hopped on board, reached out to my contacts, and started getting involved.  I deeply (to my core) love Boston.  The energy and enthusiasm of our entrepreneur scene here is just spectacular,.  It motivates me almost every day and I would do anything to help make it even better.

Let me be clear about something before I continue this post, I truly believe in what (I think) FutureM is all about.  Its wildly important to constantly challenge your beliefs, try new things, and learn from other people.  Its why I so often try crazy shit at Grasshopper, and then share those successes or failures with the community.  And believe me, If i didn’t care I certainly wouldn’t be taking the time to write this post (as my free time is very rare).

Having said that, I want to share with you 3 reasons I will not pay (and hence not attend) FutureM this year:


Don’t Charge Before You Fix the Bugs

Last year (FutureM’s first year) I had a mediocre experience….lets say 6.8 out of 10.  Which by the way is completely okay, and even expected.  The first year, or first time you do anything it is bumpy, and you certainly make mistakes.  Entrepreneurs understand that more than anyone.  But that is also why the next experience is so important.  People expect you to rebound and learn from your mistakes.  If you don’t make the necessary improvements, you will lose your audiences attention forever.  Its the same in a startup right?  If you don’t listen to your beta users (your earlyvangelists) and fix the problems they encounter – you will not having paying customers and you will not succeed.

This is only FutureM’s 2nd crack at this.  They haven’t proven to me (their Beta user) that they have fixed the bugs, so why should I start paying them?  If they had held off on the trigger finger for a year or two, and proved that they listened and acted on peoples feedback, this might be an entirely different post.
They haven’t even given us an opportunity to have a positive experience.  I feel like my free-trial got cut short.


It Feels Very Corporate & Salesy

On their home page it says “FutureM is about them”.  I call bullshit.  This year it is starting to feel like its much more about MITX or bigger companies like Hubspot, than about us (the community).  If you look at the screen shot from the “Buy a Pass” page you will get an idea of what i’m talking about.

First, if you are an MITX member you get a discount.  What?  I don’t get this, are you trying to incentivize people to be an MITX member, or are you trying to rally the community around a great idea?  Its very unclear.  If you really wanted to say “Thank You” to your members, isn’t there a much more stealth / less public (salesy) way to go about doing it?  Say email them a discount code?  This almost seems like a smack in the face for non members.

But what really made me laugh out loud (yes i just typed “lol”), was this sales pitch on the bottom (follow the red arrow).  “If you need help determining if you are an MITX Member…” – yikes guys.  I mean, I am sure if you are paying them ($150-$4,000) every year you are definitely aware that you are a member.  It is just a blatant sales pitch, and well it makes me feel a bit dirty about the whole situation.

Does anyone have any idea the organization who is behind SXSW?  Didn’t think so.


What If I Just Want to Attend 1 or 2 Events?

One thing that can make FutureM difficult is that the events are all day long (starting at 8:30am), and scattered throughout Boston & Cambridge.  So for people with full time jobs (the target audience for this event) it can be really hard to find time during the day to travel to a handful of events.  It can also be difficult to get from event to event as there is not one central hub.  So my colleague and I for instance, could very easily justify making it out to a couple events.  But then it is $50 an event?!  On a normal Boston week there are more events than you can even comprehend being put on by cool startups for FREE.  So where is my motivation?  MITX advertises that you get access to 50+ events for your $100.  I would challenge that any human could physically make it to even close to that many events.  Its logistically impossible.  The reality is that most people want to dabble, and this pricing makes that difficult.

I was also surprised that there was no student pricing?  I mean we live in a city which is driven more by our universities than almost any other city in the country.  How can we not support them learning from a week like this?  $100 in college would have gotten me through an entire week of eating and drinking, I certainly would not have used it to buy a week long pass to a conference.


I would simply challenge MITX (or any organization charging money for that matter) to be more transparent and really explain the $100 cost.  I for one feel more comfortable with things when i understand the “why”.  In this instance, MITX is actually not throwing any of the events.  All of the events during FutureM are organized, funded, and executed by the companies who volunteer to get involved (like we did last year).  So where does the money go?  I thought these companies were stepping up, and volunteering their time so it could be free for the community.

Transparency goes a long way MITX, maybe I will see you next year….


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How to retain the best talent

I’ve been out of college for 3 or 4 years now and as my younger friends all graduate I’ve started to notice an interesting trend.  This idea of the “corporate ladder” is becoming less and less acceptable.  What am I referring to?

Jr. Analyst —> Financial Analyst 1—> Financial Analyst 2 —> Financial Analyst 3 —>                                         Finance Associate —> Finance Associate 2 —> Senior FA —> etc. etc. etc.

(I mean i was legitimately bored just typing that)

Accounting Intern —> Junior Accountant —> Staff Accountant —> Sr Accountant —>                                      Accounting Manager —> Controller —> etc. etc. etc.

Sorry. Sorry. I’m done now, but I really felt I had to prove a point there.

The first problem here is that when you graduate, regardless of how much you have to offer, there seems to be a clear path you have to follow.  More and more people want to be compensated based on the work they do, not the years they’ve been at your company (that might be the most important part of this post, and worth re-reading). Now don’t get me wrong, I understand there needs to be some structure, something for people to work towards.  That is very important.


What I am saying is that there needs to be way for “your best employees” to excel.  Now this might upset some of your other employees – “Why is she getting more responsibility (and money) than me?  I have been here for 5 years!?”.

I say thats fine.

Its much easier to replace someone like that than it is to find another “Erin Bury”, who is really getting after it and truly cares about your company.

Here is a real life situation that got me thinking about this in the first place:

(as you will notice the more you read my blog, I am a huge proponent of examples, scenarios, and hypothetical situations)


Example: Phil

I have a friend, lets call him “Phil”, damn is he smart.  This kid is definitely going to be on Jeopardy one of these days.  He reads a lot and is very good at finding the most efficient way to accomplish something, and then repeating it over and over again.  Needless to say he’s a kick ass accountant.  Lets say Phil’s company expects him to be in the office for about 40-45 hours a week.  Because he’s so good at what he does it really only takes him 60-70% (or approx. 27-28 hours) of his time each week to do the work given to him.  Based on how the system is designed there is absolutely no benefit to him doing any more, so he spends the rest of his week reading ESPN, getting involved in conversations on Reddit, and other time killing activities.

Now I get that nobody spends 60 minutes of every hour working, thats unrealistic.  But Phil could certainly be a more powerful force in his department, if the system allowed for it.  Instead he is limited by something as silly as his age (24).  I don’t need to start listing off all the people who have done amazing shit by the age of 24 do I? (but in case you were curious)


One other thing to watch out for:

People tend to feel like the only way to grow within your company is to take on a management responsibility.  This is something I actually went through myself at Grasshopper.  I needed more to chew on, and was looking for ways to make more money / increase my value.  So I tried to do what society taught me, take on a management role.  Luckily I am surrounded by smart people who care about me, and were able to point me in the right direction.  Here are a few problems with this common misconception:

  • Logically there can only be so many managers, and if everyone thinks that is the only way to grow, you will very quickly run into a simple mathematical problem
  • Managers are very important to the growth of an organization, and if you continue down this path you will find yourself with tons of managers that frankly aren’t very good leaders.  Employees who might not even be good with people, but just thought this was the logical next step.
  • You will end up making people who know they don’t want to manage feel like they are stuck in a rut and have no place to go.

*Note: I am not going to end this post with a meaningless question, hoping people will answer that question in the comments section.  Instead I am simply going to ask that if this is something you have experience with, or also feel strongly about, please share that passion with me below*

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Let Other People Spread Your Message

I want to quickly outline two scenarios for you.  Lets just assume for a minute you are looking to buy a MacBook Pro (because well, they’re freaking awesome right?)

Scenario #1

You are in the Apple Store, you just decided to make the leap to buy a 13” MacBook Pro (it’s probably the most you have ever spent on a computer).  They are wrapping up your new baby, and you feel a strange mix of excited, nervous, and maybe even a little nauseas (as you just spent $14-1500).  The person helping you, asks if you wanted to invest in the Apple Warranty (better known as Apple Care) for an additional $250.


You shake your head in disgust.  Why is this person who has clearly drank the “Apple Kool-Aid” trying to take MORE of my money?  I mean warranties are always bullshit, and I am sure this person makes a commission on each warranty they sell.

Scenario #2

You are on Apple.com, after 3 weeks of agonizing and doing research you finally decide to take the plunge and buy your new MacBook. You see the option to add “Apple Care”, and can’t figure out why you would ever want to spend MORE money?  But being the curious entrepreneur that you are, you google – “Is Apple Care worth it?”, as well as shoot a few of your geeky friends an email.


You read the first 3 results on Google and realize that they ALL say AppleCare is one of the most valuable warranties.  You are pretty much convinced but then one of your buddies responds to your email and in all CAPS says “Dude, you need to get AppleCare.  Your roommate could trip, spill a full beer all over your new laptop…and you would still get a replacement for free.  Enough said right?”  This is more than enough “social proof” for you, so you buy.

I lead off with this because its important to me that you buy into the idea that:

The most powerful way to sell your product/service is actually through other people.

Entrepreneurs trust other entrepreneurs; and frankly its hard to trust someone who is selling you something – no matter how genuine they are.

Not only will your brand message become more organic, but perspective customers will actually feel more comfortable giving you their money and in turn spreading your message to their community!

Here are 2 examples that really smack you in the face with how powerful other people can be:


Example #1 – How to get 3 Million Youtube Views

3 Million YouTube views in 3 months…not bad right?  Luc-Oliver, the man behind the video, really understood the power of getting other people involved.  Its human nature right, people will naturally want to spread and share content they are involved in!  Its the reason guest blog posts tend to always have the highest traffic, you are tapping into two networks (instead of one).

But how about 172 networks?

Luc-Oliver rallied together 172 enthusiastic college students and involved all of them in a ridiculously well done LibDub of “I Got a Feeling” by the Black Eyed Peas.

Each of these students sent the video to their average of 130 Facebook friends, with a pumped up message saying “OMG, you NEED to check out the crazy video I was just a part of!!!”  Those people in some way or another then spread the message to their average of 130 friends….

172 people x 130 friends x 130 friends = 2.9 MILLION VIEWS

(note: a year later this video has nearly 9 million views)


Example #2 – How a Love Letter got me to Tweet (and blog) about LessFilms

I mean seriously, when was the last time a company you are friends with sent you a video love letter?  Shit when was the last time anyone sent you a video love letter!?

Backstory: The guys from LessAccounting, put on an awesome conference every year called LessConf.  They are also launching a new product/service called LessFilms.

LessConf was 2 weeks ago and because Grasshopper (the company I work for) and LessAccounting have such a good relationship we like to help out by sponsoring beer & food at their pre-party!

Fast Forward to earlier this week.  I get the following email from the founders:

“Hey Jonathan

We really appreciate you guys sponsoring this year’s LessConf. It was an amazing time and it’s all thanks to Grasshopper.

We created a video… It’s our love letter to you.”


I mean I repeat…really?!?  Who does that?  Its so amazing (and yet so smart).  They took a clever, risky, and fun approach to say “thanks”.  And the best part of it all, is that this is really a HUGE advertisement for their new service LessFilms.  Not only did they make me feel like I had to tweet about it (because it was damn unique), but here I am blogging about it right now!

I bet you reading this post & seeing this video makes you want to work with them more than seeing a banner ad or hearing a radio spot?

The power of people & word of mouth my friends.


You guys have any examples where someone (or some brand) was so clever you just HAD to spread the word??

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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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