Steven Caldwell

What is the biggest challenge you’ve encountered as a lender in 2026?

The September rate hike. Too early to tell how this will be digested after nearly two and a half years of easing. There are always challenges in realigning views on valuation and revisiting metric sensitivity, both of which are critical to loan structure and overall liquidity. In the near term, some deals are pausing to recalibrate to a higher cost of capital. We are actively moving forward toward closing most transactions, with some borrowers now considering floating over fixed rate debt, while others are re-evaluating leverage and buy-downs.

Has the can been kicked fully down the road when it comes to loan extensions, or is there more leg action to come? 

While rates are higher, asset fundamentals are generally strong, and capital is available in all corners of the market. Every situation is unique, but conventional wisdom says it’s time for many positions that have been kicked down the road to find a new home. If you’ve lived with a credit position much longer than you planned, and you wouldn’t make the same investment on today’s market terms, you take the alternative.

What’s your competitive edge in deals today, and who are you competing against most often (banks or non-banks)? 

Our advantage comes from three things: a team of bankers with genuine depth of expertise, better distribution capabilities than anyone on the Street, and an appetite to support clients with our balance sheet. That combination works because our CRE platform operates as one coverage effort across products, so clients’ financing requests get answered with the full range of creative solutions rather than whatever’s in front of them. We’re active simultaneously in CMBS, balance sheet, and agency lending, as well as investment banking, and given the dynamic nature of CRE investing and capital markets, that connectivity makes us the most relevant institution in our business. It shows in our performance — we’re leading roughly 75 percent of the SASB transactions on which we’re mandated, with about $45 billion of debt issued year-to-date, and the pipeline is just as strong.

Is AI indeed going to kill us all? 

I think we’re still a long way from the Terminator. AI is making us sharper, smarter about information, and more organized in how we use it. It’s not all upside, though: Some parts of the economy will have to adapt their skills and workflows as AI changes how the market works. Businesses will still need to develop future leaders, not just deploy better tools.

If you were marooned on a desert island, which three items would you bring, and what would be your key survival skill? 

A fire starter, a machete and a large container for rainwater. I really enjoy building things, so between shelter, traps for food, and living room furniture, I think I’d be living somewhat comfortably in no time. Maybe I’d even want to stay on the island?

Biggest headwind and tailwind to lending activity in 2027?

The biggest headwind for lending activity will be the “higher for longer” rate environment putting acquisition activity and opportunistic refis at risk of slowing.

There are real tailwinds, however.  Despite increased cost of capital, real estate fundamentals are stable and capital availability isn’t an issue for a wide range of credit profiles.

Lightning Round:

“Traitors” or “Alone”? “Alone” — surprisingly bingeable, especially when
I’m … alone.

If you’d attended Taylor Swift’s wedding, what gift would you have given the happy couple? Fan mail from my daughter. 

Super Bowl or World Cup? Super Bowl.

Orcas or yachts? Yachts, of course.  Would I be riding the orca?  That might be my worst nightmare.

If you could train AI to do one new thing, what would it be? What can’t it do right now? 

Best vacation you ever took? Skiing in Japan a couple of years ago! 

Conversions: “Keep `em comin’ ” or “Sooo 2020 (scoff)” Keep `em coming

Book reader or phone scroller/email checker before bed? I love books, but … the scroll is too good.

Fitness activity of choice? Weights, running, calisthenics. Highly focused on pull-ups lately. Watch out.

“Power” song you listen to when mentally preparing for a big event/deal/day? “Punch You in the Eye” by Phish.