Desmond Fleming on the Importance of Founder Vision and Employee Impact

Desmond Fleming was drawn to Cadre through founder Ryan William’s vision to democratize real estate investing for as many people as possible. (That vision has also attracted backing from Goldman Sachs, Peter Thiel, Mark Cuban, and Vinod Khosla, and a 2019 valuation of about $800 million.) Cadre most recently launched a new $400 million real estate fund, The Cadre Direct Access Fund, to help individual investors, financial advisors, and institutions invest at more reasonable costs with good liquidity. And since we last spoke to him, Dez took the leap into VC as a new investor at FirstMark Capital, where he will focus on investing in fintech, real estate, and B2B software. 

In this Q&A, Dez talks about how to set employees up for success, the importance of finding wants and needs in customer profiles, and how tapping into your own network may be more beneficial than you thought. 

As an early hire, what were you looking for in company plans and founders?

Something I looked for was the ability to drive impact earlier on in my career—Cadre's afforded me that opportunity and I am incredibly appreciative of it. Also, from a founder perspective, I was looking for someone who was a leader with a clear vision. So much of early-stage entrepreneurship is building the right teams and working with people effectively, and Ryan is the type of person people rally around. At the end of the day, the people you're working with are going to be the drivers of the business, so you want to work with the best people possible, which Cadre has.

What do you think founders should know to help support early employees like you?

Founders should understand the impact of early-stage scaling. In my opinion, it's about setting your early stage employees up for success, which entails a variety of things. This can be staffing them with the right projects and/or giving them the right resources. In the startup world, everyone's moving at 100 miles an hour, so the worst thing a founder can do is point someone in the wrong direction or put in barriers that prevent people from moving at the right speed.

What are some of those resources that have been super helpful for you?

Every company is different, but it’s about finding the best processes that make your company work as smoothly as possible. At Cadre I met with Ryan about every three weeks, and I worked with our General Manager on a weekly basis to set priorities and uncover new opportunities. I believe the process is different for each company, but this system has worked for us. Having connectivity with senior management is important because it's allowed me to advocate for the right level of resources and receive direction from management while maintaining a level of agency over my work. I think the model we use creates a sweet spot for impactful work to get done.

What's your advice for real estate startups figuring out their ideal customer profile and/or product market fit?

Customer profiling is hard and will be different for everyone. It's about getting a strong understanding of who your early customers are and why they are resonating with your product. If you're building a plane and that plane is going from New York to Miami, you may think the reason why everyone's coming to the plane is because they've got a trip to Miami. But you could realize that the reason why they're coming to the plane is actually because you have the most comfortable seats.

That's a huge distinction and something to double down on, because it influences the value proposition for your business. Understanding the driver of someone's desire to adopt this new habit or try this new product or brand that you've built is pretty critical—and it's much easier said than done.

What advice do you have for other operators in New York City real estate?

What has been helpful to me, especially throughout the pandemic, is being deliberate about tapping into my network and checking in with people. I’ve realized that you never know the effect of what reaching out to someone may have or what opportunities may come from it. There's also an added benefit. I personally have been lucky to be exposed to a lot of cool, smart people here in the city. I don't think you should go into the mindset of meeting up with someone to reach a commercial objective. The best opportunities sometimes come from a mindset of spending time and investing in relationships and building a stronger connection.

A lot of times when you do that, the most amazing things will happen. I always encourage people, especially those who are earlier on in their career, to just be proactive about helping others and putting yourself out there, because you'll be surprised about the things that come back your way.

What real estate trend are you most excited about right now?

I'm excited about seeing how this post-COVID return to office shakes out. Personally, I like this hybrid model. I'm probably in the office maximum three times a week, or even two. I think that having more of that agency as an employee is great because it really makes you have a better work-life balance. I would love to see what the office landscape will look like a year from now, especially in a market like New York. In general, I believe people are going to optimize and figure out what works best.