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Why Happy Grasshopper CEO Dan Stewart Is So Chill

Editor in Chief Sarah Wheeler sat down with Dan Stewart, founder and CEO of Happy Grasshopper, to talk about the company’s tech strategy in creating content that resonates with consumers. Storytelling is key to the company’s success and Stewart’s own story explains how he stays cool in any market cycle. Turns out being stranded at sea in shark-infested waters puts everything else in perspective.

Sarah Wheeler: What differentiates your technology?

Dan Stewart: When you think of the technical landscape today, specifically for CRM, at the very core, everything does almost exactly the same thing: It segments contacts and it sends messaging. That’s not a significant technical challenge. The challenge is creating and delivering messaging that produces the desired result for the person sending the message. And that’s what we focus on.

Today we’re nurturing about 37 million contacts on behalf of our members. And we’ve built a reporting engine we affectionately call queen bee reporting. We leverage AI to crunch the numbers, because the datasets get so large so quickly. We leverage AI to make sure that our members are sending content that’s most likely to be well-received by the target audience and to produce the conversations that they need to have.

SW: How do you know what the “right” content is?

DS: Looking in the data, it really highlights some key things:

The No. 1 thing that determines the effectiveness of a message is the relationship between the sender and the recipient.

We all have people in our lives, it doesn’t matter what the subject line is, we’re going to pay attention to their message because it’s from them. Right? On the other hand, if your phone rings and it says potential spam, there’s almost no chance you’re going to answer it. So relevancy of that relationship is very important.

The second most important thing is the relevancy to the time that the message is sent. So the cycle of what’s happening in the world becomes extremely important for creating effective messaging. The way to start that conversation is to leverage what I call the formula for engagement — basically we have to raise their curiosity and leave it unresolved.

SW: What are some use cases of the formula for engagement?

DS: So first, as a brand, we create content for agents that’s designed to go to people they know, typically past clients and sphere. And this content is not typically about real estate. It’s about something interesting that’s happening today, that we can use as conversation starter.

The second type of content we send is lead conversion and nurturing content. The timing, the duration, the frequency — all of that gets influenced by the source of the lead and the time of day that the lead is captured.

The third category is the attraction and recruitment of more people to a brand. Whether it’s branch managers to a mortgage firm, LOs to the branch manager, real estate referral partners to the LOs — there needs to be a very clear understanding that the content strategy must be very appropriate to the goal.

SW: What really differentiates your tech?

DS: Happy Grasshopper is a true managed service so our tech is very important, and yet our core belief is that tech alone isn’t enough. Agents have a lot of technology today. But that doesn’t mean they’re using it as well as they could be.

I have three core beliefs that really underpin everything I do at Happy Grasshopper. The first is that whatever we want to achieve in business, it’s most easily achieved through relationship. The second is that relationships only really live in one place and that’s conversation. And the third is that conversations lead to closings. I’ve yet to meet an agent or an LO who will not earn more commission if they have more conversations.

SW: What past experience influences the way you think about tech today?

DS: Prior to Happy Grasshopper, I built and exited a CRM company. We built white label software for franchisors — we gave the brand exactly what they wanted. And then of course, they’d roll it out to their franchisees who would log in once and then almost never come back. Which was what kept me up at night at the time.

Post-exit, I had this realization that we did it in the wrong order: we really should have built from the bottom up. So very intentionally when I started Happy Grasshopper, we focused only on serving the end user. And then we added teams, and then we added brokerages. And now we’re at the true enterprise brand level. And we get lots of usage and engagement in our application, because we’ve built it in such a way that the end user actually gets value from it every time they use it.

SW: How is AI helping you with the actual content you create? Or is that created by humans?

DS: We do not use generative AI to create content for our members. We have a staff of real human writers, college-educated, with 401(k), medical, dental benefits — real, actual people who take the time to interview our members. And we ask our members to review the content that we wrote for them and confirm whether or not it sounds like them.

And then we leverage the AI to really scrub the data — we’re sending messaging to 37 million contacts, we really need help understanding what the results of all that data means. It’s not like we have just one reporting page where you could see what your open rate was on a particular email and make a good decision. We’ve used the API to parse the messaging for tone, for length. And we use that data in conjunction with the data reporting, to help our human writers understand why particular messages are more successful than other messages. And I’m really proud of the results we’ve been able to create for our members.

We have taken the time to really build this, and we’re at the precipice of massive scale. We’re about to grow tremendously. Because it’s, it’s time for the brands to really understand how we can help all of their agents find more transactions. And in a market that’s having fewer deals closed than in years past, relationships are what’s going to lead people through this.

What do we do in our lives in times of crisis? We turn to people we trust. Whatever’s happening in the market, it can always be used to start a valuable conversation and help the right-minded real estate professionals show up as people who provide massive value rather than just attempt to garner commissions.

SW: What’s the profile of your members?

DS: We have members today in about 40 different verticals. Over 90% of our membership is in real estate and mortgage and we create content for buyers agents, listing agents, team leaders, broker owners, regional management, national management. We’ve also written content for brands.

SW: How do you think about cybersecurity?

DS: At Happy Grasshopper we don’t retain mortgage information, financial information — no one uploads that into our system, because it’s not necessary for us to have that information on file. So just from a business case perspective, if we were ever breached, the sorts of things that would be taken, we would just be limited the contact information. And course, that would be a horrible thing. But I know that being diligent and then having a business use case where we’re not really hanging on to any sort of super-sensitive information is an advantage for us.

SW: What keeps you up at night?

DS: Almost nothing. I sleep incredibly well. I’ve lived a very weird life. I moved a lot. As a kid, I had 14 schools before I graduated. One of my formative experiences was when my father’s boss inherited a sailboat. And my dad volunteered to sail it from the Florida Keys up to Sarasota. And the boat sank — we spent the better part of two days thinking that the sharks were going to come in and eat us. I can tell you: there’s nothing that I’ve ever faced in business that scared me as much as that.

SW: What? I think we need more details!

DS: My dad was a West Point grad, a civil engineer. He was an experienced power boater — he was not an experienced sailor. And that didn’t bother him. He thought, ‘You know what, this would be a great family vacation, let’s go.’ And so we left Islamorada, sailing due east. And he sailed us right into the largest barrier reef in North America. It knocked a hole in the side of the boat and the boat went down really quickly. It leaned over on its side and we had this little hump of fiberglass just above the water that we clung to the rest of the day, waving our arms. And then the sun went down and the tide came up — that night was terrifying. [The family was in the water another day] As the sun came up on the second day, there was a Coast Guard cutter, and they came and got us off the reef.

So, how privileged are we to be alive at this particular moment? The poorest of us have access to things the richest people up to 100 years ago couldn’t even imagine. It’s an amazing time to be alive. And I feel really privileged to be part of that fuel that’s connecting people in the digital age.

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