“Are We There Yet?” A CRE Stand-up Special with JP Conklin

JP Conklin is funny. And not in an ironic sort of way.

This jack of all trades is dangerously quick on the draw with a one-liner, which is probably why his side gig as a podcaster has taken off the way it has (he doesn’t want you to listen to that either). While JP might not be a comedian in real life, he is a lot of other things, including: a founder (of Pensford and LoanBoss), a veteran, a father of five, and a private pilot. And while he might be chock full of jokes, he’s deadly serious about tech.

In our conversation, we discuss how to nail your first job interview, why ‘disruption’ is a four-letter word, and where the future of #CRE is headed (and why it’s taken so long to get here). So, to repeat what is surely a question he gets asked by his children constantly: “Are we there yet?!”

Listen to the full episode below, or continue reading for a quick skim of the highlights.

Learning to Fly 

There are many parallels to be drawn between flying a plane and navigating any sort of new or challenging situation – one obvious example being a fear of heights, to which JP says, “It’s not the heights you should be concerned about, it’s the pilot.”

But what comparisons can be made between being Pilot in Command and running a business? Here’s what JP had to say about it: 

“Running a business is so much more stressful. I don’t think I ever expected that I would have to expend so much energy on my team’s mental wellbeing. I come from a military background, then the trading floor – neither of which care much about your wellbeing – and over time I came to realize that from our younger crew, they just expect a different level of involvement from leadership in their emotional and mental wellbeing. At first I was extremely resistant to it, but over time I’ve come to appreciate that they’re just looking at things through a different lens. If I invest in them, they will reward us with commitment.” 

Rolling with the Changes 

One theme throughout our conversation with JP was a continuous return to leading with empathy. Nowhere is the generational gap felt more than in the office (as evidenced by the previous excerpt), but that doesn’t mean the clash isn’t bringing about positive change. 

When asked about how his previous experience has shaped him today, JP reflected on the cutthroat environment of working on a trading floor – and why putting people first is a winning strategy in the long run. 

“I think I was such a mess of a human being when I was at Wachovia. Some of that was the trading floor environment. It’s a very self centered, self absorbed mentality, where you’re just trying to protect yourself. Even though you might be teammates with someone, you’re competing with them. As I left and started my own businesses, It really forced me to explore the value in thinking of others and putting others first. Now it’s more about “how can we build up everyone around us and succeed as a team, instead of as an individual”?

Accidentally in [Tech]

JP isn’t afraid to admit that while he may not qualify as a true ‘techie’, he knows opportunity when he sees it. If you ask, he’ll tell you that he landed in the tech industry ‘by accident’, but his explanation quickly reveals he deserves far more credit than that. 

“I challenged the team to think about ways we could become a technology company. As we began exploring that, I started to realize the impact that tech was going to have on our industry, specifically. Our industry is so far behind the curve in so many ways…the tidal wave is coming. You’re either going to be on that or drowned out by it. I think what excited me was the ability to solve problems in a way that we could not do in Excel. My universe had been limited to Excel, email, copy/paste, Word, and “save as PDF”… but it could be so much more dynamic and that was a blast to explore. But I am also the world’s worst tech leader because I can barely log into Outlook. So that’s kind of been an ongoing joke here.” 

Appetite for…Disruption 

Words matter, and in our conversation we got into the differences between “enhancing” vs. “disrupting” and why tech companies in the CRE space may want to shy away from their use of the latter. 

“It’s progressing slowly, but part of the reason for that is because it was already doing really well. It wasn’t something that was totally broken and when I think about it, ‘disruption’ is best suited for something that’s working terribly or doesn’t exist at all. Very rarely would you describe something that’s making incremental improvements as ‘disruptive’. 

When I think about brokers specifically, they’re already amazing at their jobs. There is no reason to go ‘disrupt’ that. Instead, can we look at ways of enhancing and complementing that by giving them the tools to be better at their jobs?” 

JP’s take on the nuances of CRE is an important call out for the tech industry at large and asks us to be more thoughtful of why we’re creating new technology in the first place – for people. 

“[Brokers] play a vital role in the overall process and if they weren’t good at their jobs, borrowers could very quickly figure out how to call a bank. It’s not rocket science. It just tells me, think about how good they have to be at their job…and how much value they bring to a transaction that people pay them extra to insert themselves into that process. And if that’s the case, then it doesn’t feel right for disruption. Let’s give them the tools to be even better, but to just be the next tech company standing on a soapbox screaming ‘disruption’ at the top of our lungs just feels like a losing cause.” 

Listen to the full episode here.

Lindsay Curry | Head of Marketing