I’ve always been an entrepreneur at heart. Even before I knew what that word really meant, I was out there hustling - not because someone told me to, but because it was fun. Growing up the son of a real estate technologist and a cereal entrepreneur, and the grandson of “a man who could sell ice to a polar bear,” I was surrounded by problem-solvers and deal-makers. But to me, it wasn’t some grand entrepreneurial upbringing. It was just my normal.

From a young age, I was always scheming up ways to create value. In 5th grade, I had a Power Seller account on eBay - technically under my dad’s name - but it was mine in every way that counted. I’d spend hours taking photos, uploading listings, writing descriptions, and selling whatever I could find. One of my favorites was flipping an RC Cola machine I bought at a city auction for $5. After scrubbing it down and figuring out a workaround for the coin slot, I listed it with a full backstory about how perfect it’d be for a man cave or basement bar - I had no clue RC had such an occult following. A few days later, I was loading it into my dad’s truck and delivering it to a stranger in a gas station parking lot. I still remember my dad looking at me like, “Is this for real?” It was. And I was hooked.

That led to a candy racket in middle school - selling bonbons out of my locker for a quarter each, flipping a pizza oven from a friend’s garage, and selling collectible patches I hustled for while at the 100th year Boy Scout Jamborees.

In college, I shifted from flipping physical products to designing digital ones. I launched a freelance graphic design business and learned my first hard lesson about entrepreneurship: word-of-mouth doesn’t scale. That business fizzled out, and it stung. But it taught me something valuable - about resilience, about setting your own schedule, and about the type of person I was becoming.

 I’ve come to believe some of us are just wired differently. We’re the kind of people who spot problems and can’t help but point them out, followed by, “Here’s how we fix it.” That doesn’t always go over well in a traditional job.

Eventually, I landed inside the world of real estate tech - I would have never guessed it, but looking back, it seems so obvious with a father who had helped thousands of real estate agents build successful businesses, and created two successful real estate software businesses.

My first job was working in customer success - hearing firsthand the problems these agents had with the software, then in outbounding sales doing 100 cold-calls a day trying to screen for fit, and eventually marketing - at the time I didn't realize just how valuable each of these jobs was, but that company gave me the training grounds to build the skills I would need to eventually create my own real estate software company.

I loved solving problems. But I kept finding myself boxed in. Traditional leadership didn’t always know what to do with someone like me - an employee who acted like an owner, because our success to me felt predicated on each team member acting as one for each and every task they took on.

I’d get frustrated, and they would too. I wasn’t trying to cause trouble. I just knew we could do better, and with the hubris of a young entrepreneur - I thought working for a startup meant we all built with the speed and veracity of a team hellbent on building something great for the agents we served.

That’s when the entrepreneurial pull came back stronger than ever. In 2022, ChatGPT launched publicly, and it was like the whole world shifted. I jumped in fast, seeing it on social media and creating an account within the first few days - then a few months of personal use and study later started running workshops for real estate agents, teaching them how to use AI in their business.

They were excited, inspired - but overwhelmed. I remember looking out at a sea of ‘glazed eyes’ and realizing I had made a mistake. I’d shown them how to dig, but I never gave them the shovel. More hubris to work on.

That’s when the idea for SAM - the Systems Accelerator Manager - was born.

I didn’t want to build another CRM - at that time, I didn't think I wanted anything to do with CRM, I just knew agents needed a way to use AI - and not have to invest the months of training to be proficient, and I knew I had the ability to provide a software solution for this, agents could speak to in plain English - and it would get it.

At first, it was just me, coding late nights, turning CSS into JSON using ChatGPT because I am not a computer engineer, essentially duct-taping things together, trying to make something that could help the agents I cared about get the best out of AI. And it started to work. Agents could build resources to bring in leads, written in their writing style using a sample they provided, and work on the documents that defined their businesses infrastructure - something real estate school doesn't really cover.

But behind the scenes, I was running on empty. In the spring of 2024, I landed in the hospital after an infection in my gut triggered a near shutdown that I let go unchecked for almost four months - almost taking me out of the game… any game actually, completely.

I spent weeks rebuilding my strength - physically, mentally, emotionally. Most people didn’t know. I still showed up, still taught classes, still pushed SAM forward, and still showed up to workouts, despite significant weight and strength loss.

Then something shifted.

Summer 2024, my dad - Mark Stepp - suddenly became available. Mark’s a legend in real estate technology. He’s spent the last 35 years designing systems for some of the biggest names in the space, has coached tens-of-thousands of real estate agents to hundred+ transaction businesses, and has now (with SAM) built three successful real estate technology companies since the 1990s.

I told him, “I’ve built the bones. Now help me build your dream system.” And he did.

Together, we rebuilt SAM into what it was always meant to be: the first true AI-powered CRM for real estate. Not a digital filing cabinet, holding onto all your details, but a proactive assistant that actually did something with the data.

A system that didn’t require you to be tech-savvy, or know how to use AI to get the advantages of it, or require you to stitch together ten different tools, or hire a team of consultants, just to follow up with a lead.

I wanted to build the replacement for CRM. Something that uses the relationship building you engage in, as a super power. SAM can send personalized messages, and will build in minutes entire automations - just by describing what they need to accomplish.

For the first time, AI felt usable. It felt human. Not software you log into once a week and dread - but something that works alongside you, anticipates your needs, and helps you grow without sacrificing your sanity, or time with friends and family.

We soft-launched SAM 2.0 in the fall of 2024 with the contacts database - and fully launched the completed All-In-One AI-First Real Estate CRM January 1st, 2025 with the Properties, Listings, Transactions, and ‘Routines’ Workflow Automation Builder ready and working.

Since January we’ve helped hundreds of agents and teams get a clear look at the system with free trials, and have successfully onboarded dozens of agents and teams - cutting down on long days, helping them understand and easily build their business processes and systems into automations, and working to give them back time for the people and passions that matter most.

In April 2025, I had the honor of pitching SAM on stage at the Startup World Cup AI/ML Semi-Finals in St. Louis during TechSTL’s St Louis TechWeek.

A year earlier, I was on the same stage pitching the beginnings of an idea for SAM - still recovering from my hospital stay, nervous, unsure, barely hanging on and not even knowing what I would set off to build in the months to follow.

This time was different.

I stood there confident, clear, and alive with energy. And when I said the phrase, “In the next 12 - 24 months - we will completely remove the need to manually engage with a CRM from a desktop or a laptop at home.

All while you’re en route.” - you could feel the room shift.

That’s what we’re building. Not just software, but a new way to work. A new way to live. A future where real estate agents don’t have to choose between their business and their life. A future where technology works for people - not the other way around.

SAM is the platform. But the mission? That’s personal. Because I’ve lived the grind. I’ve seen the burnout. I’ve felt the frustration of knowing things could be better, if only someone would build it.

So, I did. And now I get the opportunity to work tirelessly each and every day to bring real estate agents and teams into the fold. To help them see the power and potential of tools like SAM - and to do the hardest part, getting to work using these tools to help themselves succeed in an industry that is difficult to get ahead in.

Progress is slow as we get word out but the coolest part? The story’s just getting started.

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