Speaking Engagements
I speak about what it actually takes to win in hospitality real estate — as an operator with a live portfolio and skin in the game, not a guru with a funnel. If your audience wants real numbers, real failures, and real playbooks, we'll get along.
The Topics
Why the top 20% of short-term rental operators are thriving while the middle disappears — and what it takes to end up on the right side of the split.
How tired, dated properties become the best performers in their market. The real playbook — capital, brand, operations — behind assets like Hemingway Estates, grown from roughly $275K to a projected $450K+ in annual revenue.
Why operators who own equity and write checks alongside their investors outperform pure managers — and how to structure hospitality deals so everyone wins the same game.
How I run a multi-market portfolio in a fraction of the hours it should take — automation, AI-assisted operations, and the systems that let a business scale without scaling headcount.
Keynotes and breakout sessions for real estate and hospitality events.
Long-form interviews. I come prepared, and I don't do surface-level.
Masterminds, family office roundtables, and capital allocator sessions.
Workshops and closed-door sessions for teams and portfolios.
No pitch from the stage. No recycled guru content. Your audience leaves with things they can actually use.
That's the deal I make with every organizer. Bio, headshot, and talking points available on request.
Book Jonathan
Send me the event, the audience, and the date. I'll respond personally — usually within a few days. And if I'm not the right voice for your room, I'll tell you so, and point you toward someone who is.
Invite Me to Speak →Podcasts and media inquiries welcome through the same form.