blog CEO Interview: Why all Entrepreneurs Should Learn the Basics to Digital Marketing


When I founded my company, SquareFoot, in 2011, while still in business school, I had no idea that it would turn into something that would keep me busy full time for the next many years and that I would raise $29 million to grow it. It all originated with one phone call from a friend. A buddy from home had a business of his own and he was struggling to find office space that would suit him and his team. He thought of me because I had worked for a few years in commercial real estate before heading to graduate school.

Frustrations Often Drive Entrepreneurialism

After speaking with him, I realized that the reason he was out of luck, and so obviously frustrated, was that traditional brokerages don’t tend to work on smaller deals of his size. And that’s the conversation that changed everything for me, that propelled me when I graduated to dive in and start my own company that would cater specifically to growing companies like my friend’s and so many other startups.

It was easier said than done. Typically, the bigger brokerages would lean on past work and word of mouth marketing to promote themselves and the similar deals they’d done. I didn’t have those luxuries at my disposal then. I knew that lots of people needed the service I had envisioned, with the same level of customer service that I’d been trained to provide, but how was I going to find them, convince them I was the right broker for them, and to get them to stick with me over the many months it can take to find and then negotiate for the right office space?

Why Digital Marketing Knowledge is Crucial

Like all startup founders, I looked to reading on the internet to learn more about digital marketing. I didn’t have an expensive budget to invest in paid advertising or to plop down for a booth at industry events. I had to be more innovative, more resourceful. And that’s when I realized that if I’m Googling for answers, so must be all the other small business owners for their various needs and answers. So I read up about search engine optimization at the same time that we were building out our company website, in hopes that by combining those two pursuits we could create a superb user experience for digital searchers. This was all brand new to me, but I had a hunch I was onto something.

Important Business Lessons

We built then a first-of-its-kind online listings platform on our website to give greater transparency to the search that these business owners would be embarking on. The first rule of digital marketing, I discovered, was creating on behalf of the user a worthy and valuable digital presence. We didn’t set out to capture people with a curtain to hand off their names and numbers. Instead, the website would serve people well, giving them the ability to sift through listings the way they’d come to expect from residential sites like StreetEasy, Redfin, and Zillow. By giving people more access to listings themselves, I wasn’t hurting my business, rather I was building it. Once they found spaces they wanted to move into, they’d need a broker to work with, and I, or a member of my team, could execute those deals. It was truly a win-win. They got more information, and we got a series of high-intent leads.

Eight years later, I continue to learn more every day about my business and how to grow it. But one of the areas I enjoy most and continue to be challenged by is the digital marketing component. Commercial real estate is a traditional industry filled with brokers who operate the same way today as they did 25 years ago. As we’ve witnessed so much digital disruption in other areas of business, much of what was built (systems, hierarchies, operations) many decades ago remains the same. That, for entrepreneurial types like me, is a key indication that there’s an opportunity to change the status quo and go about things differently.

Finding the Voids

I advise young entrepreneurs these days to assess which areas of an industry are outdated and overlooked. Usually, there’s a better way to do things, even if it’s not yet the industry standard. In this day and age, most to all industries should be sourcing leads via organic search – especially in their company’s first years – when they can convert users who are finding poor results for what should be more available to them. To get there, though, you have to do more than launch your business and put out a press release introducing yourself to the world. You have to go searching for those wayward searchers and give them a destination to come to, embrace, and enjoy. It’s through that transparency and trust that they’ll eventually share with you their contact information to get started with you.

I’m building the same rapport online that I expect from my team offline. We want people, no matter who they are or what they seek, to come to us when they’re ready, to tell us what they need, and to allow us to guide them toward their goal. Digital marketing makes that process so much simpler, as they will type into Google what they need. You just have to be ready on the other end, from both a technical standpoint and from a customer service one, to welcome them and to give them what they’re looking for.

I would imagine that there are other industries beyond commercial real estate that are sitting in 2020 ready and poised for change. The next generation of entrepreneurs will invest in their companies and also in their marketing education to build something spectacular. Today’s clients await these results to emerge and arise.



Jonathan Wasserstrum, SquareFoot CEO, has worked for 12 years in commercial real estate and eight years with digital marketing.

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