As real estate entrepreneurs, we often feel the pressure to move fast. We’re reviewing comps, scanning dashboards, analyzing markets, and trying to make confident decisions. But having more data doesn’t automatically mean we’re making better decisions. And when you’re scaling, that gap becomes expensive.
In this conversation, I sit down with Kevin Shtofman, Global Head of Corporate Development at Cherre and an active investor himself. Kevin brings an institutional lens to real estate investing and breaks down where investors misunderstand data, how to think beyond surface-level reports, and why operational clarity matters just as much as market insight. We talk about AI as a thought partner, defining your metrics early, preparing for capital conversations, and how trust and structure shape long-term portfolio growth.
Scaling is not about reacting faster. It’s about building systems that create clarity. The more intentional you are about your definitions, your processes, and your decision-making frameworks, the less friction you carry as you grow. Structure reduces stress. Clean data reduces risk. And thoughtful leadership builds durable portfolios.
What part of your investing business would benefit most from clearer data or stronger systems?
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Connect with Kevin Shtofman: www.linkedin.com/in/kevinshtofman
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