Michael DeGiorgio Put Commercial Real Estate on the Screen - Without Taking the Broker Out of the Room

The useful version of Michael DeGiorgio's origin story begins over drinks. He was four years into Auction.com, one of the early employees in its commercial division, when a mentor asked what he would do if he went out on his own. DeGiorgio had an answer ready: put commercial real estate's leasing, transactions and data online in one intuitive place. The mentor became the first investor. About a month and a half later, DeGiorgio left his job to begin Crexi.

It sounds impulsive until you inspect the apprenticeship. At Auction.com he says he held ten roles, from brokering deals to calling auctions and overseeing teams. Crexi's own biography credits him with managing more than $1 billion in property sales. He had lived the transaction from enough angles to know where the elegant diagram broke down: commercial buildings do not behave like identical widgets, buyers care about terms as well as price, and brokers tend to resist software that dictates how they must work.

His response was less theatrical than the familiar startup promise to burn down an old industry. Crexi would bend. A broker could run an auction, set a call-for-offers date, negotiate privately or use only the pieces of software that made sense. The aim was to remove the half-day chores without removing the person whose judgment got the deal across the line.

“Time can kill deals.”Michael DeGiorgio

An outsider learns the room

DeGiorgio was born in New Jersey and spent much of his adolescence around Chicago. Growing up, he moved every two or three years. Each reset required him to read a new environment, make friends and assemble another sense of community. He later framed that disruption as training in adaptation. The language is revealing: not domination, but connection; not certainty, but the ability to get oriented quickly.

Sports supplied the durable social grammar. He has described a lifelong affection for teams, professional games and strong friendships. Northern Illinois University gave those instincts a commercial vocabulary. He studied marketing, graduating in 2010, and remembers classroom business meetings followed by immediate peer critiques. Cold calling in his first job felt less alien because he had already practiced being watched, assessed and improved in public.

He still refers to How to Win Friends and Influence People, assigned in one of those business classes. The title can sound like an antique device for polished handshakes. DeGiorgio's interpretation is more grounded. His parents taught him to treat people with respect, add value before expecting a return and look for the good in others. Those principles later met a market where information was guarded, relationships were essential and a property's oddities could defeat a rigid workflow.

The middleman becomes the customer

Marketplace founders are often encouraged to delete the intermediary. Crexi made the broker central. Brokers controlled listings, understood local markets and carried the relationships that turned interest into a closed transaction. DeGiorgio argued that even very capable software could not replace the person who knew the tenants, rents, contract terms and buyer behavior around a particular property.

So the product brief became practical: help a broker do more deals, reduce the support work surrounding each one and make activity visible. Confidentiality agreements could be handled online. Buyers could review offering memorandums. Sellers could see who viewed materials or requested access. The platform provided structure, while the broker retained discretion over who saw what and how the sale proceeded.

That choice also solved part of the marketplace's cold start. Give the supply side useful tools, and brokers have a reason to bring their own buyers into the product. Utility creates distribution. It is a lesson hidden in plain sight: a two-sided marketplace can begin by making one side's Tuesday markedly less annoying.

The team spent roughly nine months building the first version. Commercial brokers and owners cycled through the office to react to ideas. The early engineering group included people with experience from Burstly, the company behind TestFlight before its sale to Apple. DeGiorgio's fallback plan was almost comically sensible. If the industry refused the platform, the founders could transact on it themselves and operate more effectively than they had before.

The house gets crowded

Crexi began in a small Venice house. By 2016 it had announced a $4.3 million seed round and a platform combining a marketplace with transaction tools. Sales listings expanded into leasing, auctions, data and market intelligence. The team grew past 350 employees by 2023 and approached 500 in 2026. At its tenth anniversary, the company said it had supported more than $1 trillion in transactions and served millions of professionals.

Numbers of that size can flatten a good operating story into confetti. More interesting is what stayed constant. DeGiorgio kept returning to access. Commercial real estate offered routes to durable wealth, yet reliable information and opportunity had often traveled through closed networks. A searchable marketplace could widen the front door. Better activity data could make a sale less mysterious. Flexible software could welcome an industry into digital work without demanding that it abandon its instincts overnight.

Recognition followed. Northern Illinois University gave him its Outstanding Young Alumni Award in 2018 and its College of Business Innovation and Entrepreneurship Award in 2023. He returned as a visiting lecturer in entrepreneurship. GlobeSt named him among its 2022 CRE technology influencers. The Los Angeles Business Journal included him in its LA500 in 2024, 2025 and 2026. The circuit from student critique to guest lecture feels neat, although DeGiorgio's advice to students remains decidedly untidy: treat yourself like a business, put in the hours, keep working on yourself and ask other people what they know.

AI enters, trust stays

The new chapter has the unavoidable initials. In 2025, Crexi released Vault, a tool that extracts property information from offering memorandums and turns documents into structured records. The company said testing reduced a typical document task from about 30 minutes to roughly two. In 2026, it presented a broader suite covering document processing, data enrichment, market reports, listing creation and marketing documents.

DeGiorgio's pitch for AI sounds like his pitch for the first Crexi product with the nouns updated. Preparation work should shrink. Professionals should get back to relationships, judgment and closing. Data must be accurate enough to support decisions and transparent enough to earn confidence. He has written that trust is commercial real estate's currency, particularly as software begins producing more of the material people use to evaluate risk.

“True trust isn't blind faith, it's informed confidence.”Michael DeGiorgio

It is a restrained answer to an extravagant moment. The industry does not need a machine to cosplay as a broker. It needs documents read faster, records made usable, market signals organized and people left with enough time to call one another. The job of technology is to make the human layer more valuable, not merely less busy.

Progress, with a tee time

Outside the company story, DeGiorgio's disclosed tastes are pleasingly unoptimized. He likes golf and nearly anything involving sports. Asked for a favorite film, he split the decision between Gladiator and Meet the Parents, an emotional range that could cover most board meetings. Los Angeles earns points for food, weather, beaches, mountains and golf throughout the year. Traffic receives the predictable veto.

Travel sits near the top of his bucket list, especially Asia and the chance to observe how other cultures conduct business. The curiosity fits. His career has been built around entering a room with established customs, spotting which customs are useful and asking whether the rest can become a few clicks. He likes a line about comfort and progress being poor companions. Moving towns taught it first. Sales taught it again. Building Crexi made it an operating system.

A decade after that drink with a mentor, the company is larger, the tools contain more intelligence and the paperwork moves faster. The aspiration remains modest enough to be demanding: open access, preserve trust and let capable people spend less of their lives tending the machinery around a deal. There are flashier versions of the future. Few are as considerate of Tuesday afternoon.