Nick Sinatra

Have a purpose. Whether it’s a purpose for the day, the week, the quarter or your overall company mission—be purpose driven.


Nick Sinatra is a distinguished real estate professional who possesses a unique vision for his hometown, Buffalo, New York. From a young age, Nick could envision Buffalo being converted into a world-class city — all it needed was someone to believe in and access its untapped potential. Shortly after receiving his MBA from the University of Pennsylvania Wharton School, Nick Sinatra decided that he would be the one to help redevelop Buffalo. As such, he began purchasing and flipping properties after the most recent market crash. During that time, Nick realized that it was imperative for him to prioritize people over profits, and that guiding principle has stuck with him throughout his career. To glean further insight into the work Nick and his company, Sinatra & Company Real Estate, have achieved, be sure to visit his website.

Where did the idea for your company come from?

It has always been with me. I wrote a paper at Yale in an urban studies class which focused on how Buffalo could redevelop itself and be prosperous again. Then I was at business school in 2008 and the world came unglued. So, there was an opportunity to buy real estate at very attractive prices as markets in turmoil tend to overreact, but there were also few jobs out there in the real estate space for MBAs with little to no experience. As such, an idea turned into necessity. I went on pitch after pitch and ultimately there was a yes after 50 plus “NO’s.” Needless to say, fundraising requires determination and a thick skin. A $100,000 investment on a handshake has turned into millions more and was the foundation of what is now a half a billion-dollar real estate company — and growing.

What does your typical day look like and how do you make it productive?

As you can imagine, no day is typical. Exercise in the morning… sometimes. I’ve found that exercising regularly helps me maintain focus in general, but it’s hard to fit it in. It’s impossible after work — always something work related that keeps me occupied well into the night. By the time I leave work, it’s either too late or there is yet another social event I need to attend. It’s something I’m working on getting more regimented with.

Beyond that, I always start at Dunkin Donuts. I started drinking coffee while I was in college in New England and so there was a Dunkin Donuts on every corner. Now I have grown to like the coffee and lids. Everyone in western New York loves Tim Horton’s coffee but I cannot stand the cheap, flimsy lids. Then I spend my first hour answering emails, planning out my day before I jump into the fire of the day. Every few weeks I make a list of the most important things I have to accomplish, but the day never plays out the way I envision it. As most founders can relate to, things often change day to day. Running a company requires flexibility and constant adjustments to priorities.

I try to break up the days by area of focus: Each week, I’m involved in leasing/marketing, fundraising/investor relations, development/construction (all phases), cash management and general HR issues. I tend to be out socially three to four nights a week, too. Whether it’s a local charity event or a business dinner, I think being present in the community in which we invest is important.

We have properties in various different locations so traveling is common as well. So, the weeks can be jammed. But there is one rule in my household—no work on Sundays. My wife is adamant about it. She made me make it part of the vows!

How do you bring ideas to life?

Bring them to our team. We have a great team at Sinatra and Company. We would be nothing without our team. Real Estate is capital intensive–human capital as well as the greenbacks. It took us many years to build a great team and we are proud of our team’s capability—I think it is actually a barrier to entry for our industry. Technology and outsized amounts of capital cannot replace hands-on experience in the construction and property management space. It takes years to build competency in both fields and there is no replacement for it.

What’s one trend that excites you?

Opportunity Zone Development in our urban cores. This is something that comes out of the federal tax bill. And it wasn’t really well known until last year, but the potential is a game changer. Essentially what it does is as follows: it allows for investors to have a special tax treatment on their capital gains by investing in the opportunity zones which are typically in urban areas. These are mostly areas that otherwise haven’t seen investment and so it is meant to be an incentive for capital to move into these zones.

One of the unique aspects about the opportunity zone investments is that they are long term. They’re 10-year investments, so it’s a little bit like a marriage. An investor has to feel comfortable working with the development company that has a great track record and is a leader in that specific geographic area.

Sinatra and Company is uniquely positioned because we are already working on a number of developments that happen to be in Opportunity Zones. We have great projects that were underwritten prior to the Opportunity Zone program so they have strong development potential and now because of the tax treatment, they are really attractive. But the most exciting aspect of this program is the future development projects in neighborhoods that are now getting a second look from investors. This can be transformative for our urban cores. There’s been a great transformation across the country for investment in America’s cities which potentially could be deeper and broader.

What is one habit of yours that makes you more productive as an entrepreneur?

Hard Work. That has always been my edge. I will outwork the other guy. I am a grinder. Blue Collar work ethic with a top-notch education and a big heart. That’s what defines me.

What advice would you give your younger self?

Be focused and Buy more apartment buildings! When building an organization, I’ve found it’s more important to have people with strengths and background that enhance mine. By building a well-rounded team, we accomplish more and avoid the blind spots that occur when running hard. There are no rearview mirrors on a rocket ship!

Tell us something that’s true that almost nobody agrees with you on.

Pasta is soul food! It’s been a staple food for civilizations over thousands of years and now people are moving away from carbohydrates and gluten. I think it’s a fad. Pasta will win the day.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Have a purpose. Whether it’s a purpose for the day, the week, the quarter or your overall company mission—be purpose driven. Have a purpose and strive to make a positive difference. This works. It’s motivating to your team to get behind a purpose and it rallies stakeholders to your vision. It’s something that can be walked out daily or over extended periods.

What is one strategy that has helped you grow your business?

Accretive Outreach. I believe in building and fostering relationships. That has been a key strength for me personally, and by extension, the business. The key, however, is making the relationships symbiotic—meaning both sides need to bring something to the table. Many think networking is grabbing business cards and calling on someone when YOU NEED something. I believe to build strong, long-lasting relationships, it is important to be present and add value when YOU DON’T need something. Do a favor—pay it forward from the last time someone was able to help you. Or just do it because you can or because it’s the right thing to do. Then miraculously when you need something, people step up.

What is one piece of software or a web service that helps you be productive?

Real Estate has been a slow adapter to technology. The new trends in PropTech are exciting and I hope it helps make the industry more efficient and productive. We are looking into a new construction software app now. But the most exciting trend recently is crowdfunding—Crowd Street and Invest Real are two we are using now.

What is the one book that you recommend our community should read and why?

1776 by David McCullough. It’s a great snapshot of the miracle that is our country. Everyone needs to know the revolutionary history of this great country.

What is your favorite quote?

The Best is Yet to Come! — Frank Sinatra