Career & personal journeys: Todd Stofflet & Jason Stevens, Walker ＆ Dunlop

Todd Stofflet and Jason Stevens, Managing Directors of Walker & Dunlop’s Chicago office, joined the company in December of 2020. Prior to joining W&D, the duo worked at a few different CRE firms and were even approached to start their own boutique firm, which they successfully developed. Todd and Jason have been business partners for eight years and have also been married for eleven. Read on to learn about Todd and Jason’s career and personal journeys, their approach to leadership, and advice for up-and-coming CRE professionals. 

At the beginning: The CRE journey

TODD: After graduating college, I was trying to figure out what I wanted to do in life. I opened the Wall Street Journal one morning and saw a Marcus & Millichap spread that highlighted all the fantastic million-dollar deals that they were doing. I thought to myself, “I want to do that.” So I picked up the phone, called the head of Marcus & Millichap in Chicago and asked if I could work for him. That’s how my career in commercial real estate began. 

JASON: I had a long history of strange and unusual jobs until I was about thirty years old. I put myself through college so I was doing whatever I could to support myself, including working as a morning show radio personality and in the automotive industry. I eventually got into residential real estate which is where I met Todd. In 2008 when the market collapsed and the bubble started bursting on home mortgages, I started shifting toward commercial real estate and began learning the business from Todd. 

Approach to mentorship and leadership

TODD: The only way you learn this industry is by doing. Until you’re involved in conversations, included in meetings, and understanding the nuances, it’s really hard to be successful. The best thing you can do to support young professionals in the industry is to bring them into the fold as soon as possible. 

Inclusivity is very important to us because we know what it feels like to be excluded. On our team, that’s not an option - we’re very transparent. In CRE, if you work for a partnership or team, having a married couple, let alone a gay, married couple as the leaders is extremely unusual. That’s a big reason for us to be as transparent and inclusive as possible. Team huddles and frequent communication ensures that everyone is on the same page, comfortable, and happy in their positions. That’s really important to us.

JASON: We like to keep our team in-the-know and explain the why behind our decisions. We’re not threatened by giving people more information. We are constantly evolving, and we want our team to not only be along for the ride, but also adapt and take on the journey with us.

Advice for getting involved in CRE (and overcoming potential barriers to entry)

TODD: My advice to younger people interested in getting into the industry is that the more you can be socially active, the better off you’ll be. Reaching out to people and expanding your network is imperative to success. It may seem daunting at first, especially when you don’t see yourself represented well in the existing workforce and leadership ranks. But I believe there is a huge change going on. There is so much more opportunity for women, gay people, and minorities than there ever was before. Leadership is starting to look different than it did ten years ago. 

JASON: Keep going even if you’re not having success right away. We’ll always take a coffee or lunch meeting with someone who reaches out to us, because we know it’s important to nurture the younger generation. Keep going until you find a person willing to do that. As Todd said, things are changing in the industry. The new normal may not quite be here, but it’s coming.

What advice would you give to your younger self?

TODD: I would’ve come out as gay earlier in my career. Looking back at how I represented myself differently for fear of rejection feels very fake to me now. That would be my advice to myself, however hard that would’ve been. 

JASON: I would have found my confidence a lot sooner. People think there’s a limit to the things you can do as a minority. I wish I had more confidence earlier to chase the things I wanted. The reason I finally got into real estate is that my Mom had been telling me for years to get into the industry. I had a fear of living on commission, being in charge of my own destiny, and not having a regular paycheck. After my mom passed away, it bolstered my confidence to branch out and take the risk.

Why did you join W&D?

TODD: I’ve been a part of most of the major CRE companies. The culture and leadership that we have at Walker & Dunlop was a major reason we joined. It’s definitely a place we feel respected, and we are excited to be representing W&D in the Midwest.

JASON: Bouncing around among the major CRE companies led us to figure out that Walker & Dunlop is our forever home. Not only do we have access to a strong debt platform and a high level of service to provide to our clients, but we also value the inclusive culture that it provides employees. 

Interested in working with Walker & Dunlop? Browse our open positions.

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