Co-Founder & CEO of Sidekick - the AI assistant that real estate agents actually use.
28th Annual Webby Awards, 2024 Best AI Product & Service + Best AI Work & Productivity App
June 2024. Michael Martin called a meeting his team had probably sensed coming. Avenue 8 - the mobile-first brokerage he'd co-founded in 2020, the one that had done $600 million in California home sales in its first year, the one Craft Ventures and Threshold had bet $18 million on - was shutting down. Not because it failed. Because something better had been born inside it.
That something was Sidekick. The AI assistant Avenue 8 had built for its own agents. The tool that turned out to be the real product. Martin's assessment was characteristically blunt: "We wanted to go all in and we think we have a really unique opportunity and unique moment."
"In order to capture the moment, we wanted to put all our resources into it."- Michael Martin, June 2024, on shutting down Avenue 8's brokerage operations
This is how Michael Martin moves. Not with a safety net, but with a thesis. And his thesis is that real estate - one of the largest, most paper-heavy, most relationship-dependent industries on the planet - is sitting right at the edge of an AI inflection point. Sidekick is his bet that the agents who embrace that shift will eat everyone else's lunch.
It is, by any measure, a well-placed bet. By mid-2024, Sidekick had signed MLS partnerships with San Francisco, Miami, Greater Los Angeles, and New York - collectively covering more than 120,000 agents. The 28th Annual Webby Awards handed it not one but two trophies: Best AI Product & Service AND Best AI Work & Productivity App, across all industries. HousingWire named Martin a 2024 Tech Trendsetter. Cox Enterprises came in with additional funding.
None of this is the trajectory of a pivot that went sideways. This is a founder who correctly read a market in real time and had the nerve to act on what he saw.
Most real estate AI founders come from proptech or SaaS. Michael Martin came from Comparative Literature. At Dartmouth, he graduated with High Honors - the kind of training that teaches you to find meaning inside ambiguous systems. It turns out that's precisely what investment banking requires too.
After Dartmouth, Martin moved through Deutsche Bank and Apollo Global Management, working across leveraged buyouts and M&A deals involving Clear Channel Communications, Harrah's Entertainment, and Ceridian. These were not small transactions. These were decade-shaping capital structures.
But finance, as a career, has a ceiling for the builder type. By 2011, Martin had moved to Code and Theory, a digital creative agency in New York. Over eight years as Managing Partner, he helped scale the firm from 50 to more than 500 people. The company eventually exited to Stagwell Group on the Nasdaq. That is not a small outcome.
What the resume doesn't capture is what those years built: a particular understanding of how institutions change when technology gives them a new interface. Code and Theory's clients were organizations trying to translate their complexity into digital clarity. Martin spent a decade doing exactly that.
When Martin and his co-founders launched Avenue 8 in March 2020, they described it as a mobile-first tech-enabled brokerage. That was accurate, but incomplete. The real product was the technology stack underneath the brokerage.
"There's a rich ecosystem of APIs available today that simply didn't exist in 2012 or even 2015," Martin said at the time of the Series A. He was pointing at a structural shift: the infrastructure had caught up with the ambition. You could now build software that actually talked to the messy backend systems of real estate, including MLS databases.
Avenue 8's first year was, by conventional metrics, astonishing. $600 million in California home sales. 25% compounded monthly agent growth. 96% retention rate. These numbers don't happen by accident. The agents were staying because the tools worked.
In November 2023, Avenue 8 unveiled Sidekick publicly. The timing was intentional. The generative AI moment, turbocharged by GPT-4, had arrived. Martin had been watching it closely - and watching how poorly the existing tools translated to real estate's specific workflows.
Sidekick wasn't a ChatGPT wrapper. It was a purpose-built system that integrated directly with MLS data, understood real estate contracts and terminology, could generate CMAs from raw data, write listing descriptions from photos using computer vision, manage email and calendar tasks through conversational interface, and produce market reports on demand. "AI should not be limited to a chat interface," Martin wrote on Sidekick's Substack.
The market responded. San Francisco's Association of Realtors signed on in May 2024 - making Sidekick the first generative AI assistant to license MLS data from a major association. Within 90 days, Martin had added Miami (100,000+ agents), Greater Los Angeles (18,000+ members), and New York's OneKey MLS.
Then the Webbys. Not just one - two. Best AI Product & Service and Best AI Work & Productivity App. Across all industries, not just real estate. The judges were not looking at niche proptech. They were comparing Sidekick to everything.
The June 2024 decision to shut down the brokerage is the clearest window into how Martin thinks. Avenue 8 had agents in San Francisco, Santa Monica, Palm Springs, and New York. It had revenue. It had brand recognition in its markets. Shutting it down was not the obvious move.
But Martin had seen something: the brokerage was the hard part, and it wasn't the valuable part. The software was the valuable part. Every dollar spent running a real estate brokerage was a dollar not spent making Sidekick better. "Focusing on Sidekick allows us to channel all resources into enhancing this powerful tool," he said in the announcement. Cox Enterprises saw the same thing and came in with investment to back the pivot.
When the LA wildfires broke out in early 2025, Martin made another decision that said something about his instincts. He offered Sidekick free to every Los Angeles area agent through the end of the year. He called real estate agents "conduits of essential, life-saving information" during crises. It was not a calculated PR move. It was the act of someone who had spent years inside the industry and actually believed it.
We wanted to go all in and we think we have a really unique opportunity and unique moment.
AI should not be limited to a chat interface.
The cost of building powerful AI tools is getting cheaper - and that's an amazing thing for real estate agents.
Brokerages of the future will have a much more integrated suite of offerings and support for both agents and consumers.
There's a rich ecosystem of APIs available today that simply didn't exist in 2012 or even 2015.
As the AI capital of the world, San Francisco is the ideal place to launch Sidekick to sophisticated Realtors, at just the right time.
Most AI tools in real estate are glorified ChatGPT wrappers wearing a brokerage logo. Sidekick is something different: it integrates directly with MLS data, reads contracts and documents natively, and understands the specific vocabulary of real estate transactions.
At $25 a month - less than a tank of gas in San Francisco - it handles the cognitive overhead that burns out agents and slows down deals. CMA generation from live MLS data. Listing descriptions written from photographs using computer vision. Market reports assembled from raw data on demand. Email and calendar management via conversational interface.
The first MLS partnership was with SFAR in May 2024, making Sidekick the first generative AI assistant to license MLS data from any major association. By July, it had four MLS deals. By the time the Webby judges voted, the platform was live for more than 120,000 agents.
Martin hosts free live AI classes for real estate agents on Maven. He publishes Sidekick's thinking on Substack. The product philosophy is visible in both: real estate agents should not have to become AI experts. The tool should meet them where they are.
Won across all industries - not just real estate. Competing against every AI product launch of 2023-24.
Second Webby in the same ceremony. Two wins in the AI categories across all industries.
Named among the most innovative technology leaders reshaping the housing and mortgage industry.
Finalist for Company of the Year AND Most Innovative Use of AI at the annual Inman Innovator Awards.
Shared the stage with Adam Goldberg from OpenAI at Inman Connect New York. Session: "OpenAI and the Art of the Possible."
Sidekick became the first generative AI assistant to license MLS data from a major realtor association.