Ep 27: The Bottleneck Isn’t AI, It’s Your Business

With Zach out for the day, Stephanie takes the mic solo and brings on two people she’s building something big with: Steve Trang and Jordan Samuel Fleming. The occasion is REI Tech Unlocked, the first-ever real estate investing tech event, landing September 19 to 21. But the conversation is really about a frustration all three share, and the AI lesson most operators are getting wrong.

They dig into why they built an event with no pay-to-play booths and no Lambo mindset talks, the difference between siloed AI tools and a business actually redesigned around them, and why big technology is finally paying attention to real estate investors. Tactical, honest, and built for operators who want something they can use right now.

Key Takeaways

• Built out of frustration. The idea started four years ago on a boat in Jamaica: roughly 100,000 serious operators in the country and no honest place to evaluate the tech meant to serve them, just affiliate links and guru referrals. So the three built the event they always wanted to attend, where you sit down with the service providers your peers actually use and see exactly how the tools work inside a real business.
• The bottleneck isn’t the AI, it’s your business. As Jordan puts it, sticking a digital employee into an analog business kills the leverage. Run a thousand AI calls into a closing team built for twenty deals and you’ve created capacity that just gets dropped. The win comes from redesigning for integrated capacity, not bolting a tool onto a broken process.
• AI made productivity go up, so headcount went up too. Steve started the year an AI doomer bracing for lost jobs, and is now hiring more salespeople, customer success, and fulfillment. The productivity gains surfaced a new bottleneck: quality people. The whole business transforms, not just the one tool you plug in.
• Overwhelmed is fine. Staying the same is not. Even top AI researchers admit the pace is overwhelming, so it’s okay to feel behind. What’s not okay is for your business to look exactly the same six months from now.
• Get in the room. Meta, Salesforce and Slack, Twilio, and Collective Genius are all showing up, a sign big tech is finally taking this industry seriously. Attendees get 45 minutes one-on-one with any company (including the people who actually build the products), plus sessions on the 2026 sales team, the 2027 org chart, and trusted calling.

Left Main is more than just a CRM, it’s an end-to-end Real Estate Investment operations solution to run your company as an actual business with sales systems embedded.