DiscoverReal Estate MogulsNick DeGregorio with Zach Guysenir on Building Community That Drives Deals
Nick DeGregorio with Zach Guysenir on Building Community That Drives Deals

Nick DeGregorio with Zach Guysenir on Building Community That Drives Deals

Update: 2025-10-06
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Zach didn’t begin in commercial real estate. He spent six or seven years in auto portfolio finance, making a living but not finding his calling. A move into commercial title insurance put him closer to the industry he’d later help shape. Then a series of conversations with the team at Biznow changed everything.

The people drew him in. “Every single person was super dynamic, super sharp, super ambitious,” he said. After a call with the late CEO Will Friend—“the greatest salesman I’ve ever met”—Zach knew he had to join. He wasn’t sure if he’d be on stage or in the audience. He chose the stage and never looked back.


Today, Zach serves as Vice President of Sales across the Midwest for Bisnow, one of the most prominent commercial real estate events and media companies. He credits the work to a team-first mindset. “Nothing happens without the people I work with,” he said. That lens powers everything from editorial to events. The editorial engine keeps nearly 2 million subscribers across about 50 cities engaged. The events side hosts roughly 400 gatherings worldwide, with about 25 in Chicago alone. The aim is simple and hard at once: keep people informed and help them meet the right people to do their next deal.


Then came the pandemic. In-person events vanished overnight. The company refused to frame the moment as “if.” It became “how.” “We did almost a thousand webinars during that year and a half,” Zach said. Production shipped a webinar every week. Sales reframed campaigns. Coordination delivered at speed. They didn’t just preserve the business. They came back stronger, and they still use digital when a national niche topic needs it.


Zach’s take on sales is refreshingly direct. Relationships matter, but they are not the reason to buy. “I don’t ever want somebody to do business with me because of our relationship,” he said. The reason must be clear value. Trust is built by doing what you say you’ll do, delivering what you promised, and being accessible. Relationships accelerate timing, open doors, and create introductions, but they should not carry the full weight of the transaction.


Culture is not a poster on a wall in Zach’s world. It’s who gets hired, promoted, and retained. “We don’t hire jerks,” he said. Fun and winning sit at the core. He looks for people who care about outcomes, often former college athletes or others with a visible competitive edge. Hunger beats polish. Effort beats résumé. Everyone in the “dojo,” as they call their offices, must be an A player because every seat directly affects results.


The Midwest focus is no accident. Zach sees real momentum in Chicago and neighboring markets like Detroit, the Twin Cities, Kansas City, and Columbus. Talent density is rising. Clients are investing. The city’s fundamentals—from fresh water to a diverse industry base—support long-term growth. That thesis shapes where the team expands next and which asset classes they spotlight.


Work and life became sharper when his family grew. Early on, Zach was out four or five nights a week and logging 90-hour stretches. That wasn’t sustainable. Now he guards time with Alicia, their son Cam, and even Amy the cat. The shift worked because he trusts a strong Midwest team to execute at the same level—or better. Systems support the boundary. So does clear ownership.


If you lead sales or community, here are moves you can copy this week. First, audit your offer so value stands on its own. Your relationships should speed a yes, not create it. Second, build a simple introduction flywheel. Track who needs to meet whom and facilitate two quality intros per week. Third, adopt Zach’s “how, not if” stance on constraints. Write the obstacle at the top of a document, then list three workable paths around it within 30 minutes. Ship one.


Zach’s most durable lesson came young. After his parents divorced when he was 15, he watched them reenter dating and realized everyone, even smart adults, was learning in real time. The pressure to be perfect fell away. “We’re all just out here doing it for the first time,” he said. That insight fuels courage, iteration, and the patience to keep improving.


On career clarity, he urges young professionals to answer a basic question: what do you want? “You’re not going to get what you don’t ask for and what you don’t aim for,” he said. People will help, but only if you tell them where you’re headed.


The line that sums up his operating system is simple: “It’s not are we going to make this work. It’s how are we going to make it work.” Adopt that, and the room changes. Constraints become prompts. Teams get bolder. Deals move.


Close with action. Tighten your value. Protect your culture. Broker real introductions. Then pick one knot in your process and apply the “how” mindset until it loosens. Do that on repeat, and you won’t just grow your network. You’ll build a community that closes.

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Nick DeGregorio with Zach Guysenir on Building Community That Drives Deals

Nick DeGregorio with Zach Guysenir on Building Community That Drives Deals