Shh! It’s A SECRET. No, Not Really.

Secrets of Starting Conversations:

My “Hush-Hush” Interview with Happy Grasshopper Co-Founder Dan Stewart

Happy Grasshopper makes email cool. Seriously. When I came to work here, email was the bane of my existence; I *loathed* checking it, hated dealing with it. But then I met Dan Stewart and I began to see the potential in email’s simplicity, the elegance in its ease. When I stopped looking at email as it had always been and thought about it in a more Grasshopperian (yes, that’s a word, as far as you know) way, I began to see what it could really do.

Recently, I sat down to talk with Dan (which is so strange, because he’s my boss and my friend), co-founder of Happy Grasshopper. During our chat, while we weren’t talking about iconic 80s movie characters (“Chet” from Weird Science is a perennial favorite of ours), the state of his hair post-St. Baldrick’s shave, inappropriateness, or the solid awesome of so many of the people with whom we get to work, he had a ton to say about our new product, Position-Me (something we’re pretty proud of ’round here), and how sales folk can hone (that is, to straighten its sharp edge) the way they market their businesses and inject their strategies with a lot more power, just by doing a few simple things with the email they’re already sending.

And if you’re not using email? We’ve gotta talk. It mightn’t be fancy, but it’s tried, it’s true, and it works. Shall we?

  1. KNOW YOUR GOAL.  “If you’re not selling something that can be purchased with a click”, Dan says, “stop following email marketing dogma and focus on establishing and strengthening relationships by starting conversations.”Translation: Can the sales pitches. No one wants to hear that stuff (at least not most of the time). People will like you a heck of a lot more if they don’t think you’re constantly trying to sell them your stuff.
  2. FOLLOW UP! This seems like a no-brainer, sure, but there are plenty of y’all who are spending big money on lead-generation, but who for whatever reason, simply aren’t following up. “That’s like setting money on fire and saying, ‘Oooh, pretty!’ It’s just giving business away”, he says. “If you get a new lead, you should be following up immediately–within a few minutes, ideally, and certainly no more than an hour.”Translation: Tomorrow is too late.
  3. STOP SELLING. This might seem counterintuitive since you’re a salesperson and all, but nobody likes to be sold. You probably don’t like it much yourself. But nearly everyone likes to make new friends. “If salespeople would just stop for two seconds and treat their leads and customers like friends, they’d deepen their relationships and get a ton more referrals,” Stewart says.
    Translation: See #1 above. But honestly. When you’re hanging out with your friends, do you spend all of your time telling them about what you do and how awesome you are at it? Of course not. If you did that, they’d all give you an atomic wedgie (or they’d really want to). Why would you treat your customers any differently?
  4. MAKE IT PERSONAL. “When following up with a new lead, make the message personal,” my silver-haired cohort laughed (because that’s what we do here). “Don’t make it look like marketing and don’t use templates. Write short messages and ask leading questions.”  This will greatly increase the number of replies you get.
    Translation: Don’t be a knob. Also? REPLIES! With all of the energy you’re putting into your drip email campaigns, are you getting any responses? I bet not. What if <GASP!> people actually read what you had to say and took the time to respond? Crazy talk, you say? Read on.
  5. LEVERAGE TECHNOLOGY. If you can’t respond to a new lead right away, set up a system–like Happy Grasshopper’s Position-Me–that can do it for you. “There are plenty of systems that can auto-respond to new leads as soon as they come in” Stewart says, “but only Position-Me can respond according to the time of day a lead comes in”. This means that a person who registers on your IDX at 2 am would get a different message than someone who registers at 10 am.
    Translation: Position-Me is cool. It’s smart. And it’s changing the way people think about email marketing.
  6. NO MORE TEMPLATES. “Real estate agents have been taught that their email design should mirror their website. That SEEMS like a good idea, you know, everything being all matchy-matchy, but it comes across as disingenuous, canned, and, let’s not kid ourselves, douchey.” He says, “The reason it doesn’t work is that we have all been conditioned to spot messages like these at 50 paces. Using a template subconsciously communicates ‘marketing’ and makes it safe not to read.”
    Translation: Sending shiny, templated emails that are filled with pre-packaged, milquetoast sales messages is tantamount to buying a ticket on the express train to Deleteville.
  7. KICK THE CAN. Stop using messages that are mass-produced, canned sales pitches. “First off,” Dan says, “think about the company you’ve bought your email service from. How many other people have bought the exact same messages? How many times do you think your contacts could get those messages from someone other than you? Do your best to send original content; it’ll be more meaningful to the person getting it. One of the things we’ve done at Happy Grasshopper is to make sure that the same email address never gets the same message more than once (our Celeste is kind of a genius like that). So, even if another person is using our service and sends one of our messages to your customer, they can’t send the same message as you.”
    Translation: How awesome is that? Like email addresses won’t ever get the same message twice. That’s pretty rad.
  8. SEND EMAIL THAT STARTS CONVERSATIONS. Seems reasonable, right? Dan says that the single best piece of advice he can give is to make sure the content you’re sharing via email is something that’ll actually engage the people you’re sending it to. “If it’s something interesting,” he says, “like a timely news story, or an engaging video–much like you would see shared on Facebook or social media–a response is much more likely.”
    Translation: Just be yourself. Talk to people like they’re actually, you know, PEOPLE. Your business will be so much the better for it. And hey! You’ll be off that douche wall, and that can only help the ball club. 

As it turns out, Happy Grasshopper offers some pretty neat products to help people do exactly the sorts of things Dan talked about with me. There’s our “classic” messaging service that helps people stay in touch with their contacts, and now Position-Me, which is an auto-responder that’s designed not to come across like an auto-responder and help web shoppers decide to work with you; and HG-Recruits, which is designed to be used by sales professionals trying to build their teams (both are pretty neato, if I do say so myself, and I do). Both services use patent-pending technology to deliver customized campaigns based on who you really are (and why would you want people to want anything else?) Want to learn more? We’ve gotcha covered at

Photo Credit: CarbonNYC via Compfight cc

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