Scorecard (August 2025)

  • Over the course of his career, Bob has sold 2,358 buildings in New York City.

  • Those transactions amount to more than $22.3 billion in sales volume, comparable to the lifetime output of entire brokerage firms.

  • He also co-founded Massey Knakal, which grew into New York’s leading mid-market brokerage before being sold to Cushman & Wakefield for $100 million in 2014

Career overview

  • BKREA – Chairman & CEO (2024–Present)

  • JLL – Head, NY Private Capital Group (2023–2024); Chairman, NY Investment Sales (2018–2023)

  • Cushman & Wakefield – Chairman, NY Investment Sales (2015–2018)

  • Massey Knakal – Chairman & Founding Partner (1988–2014)

  • Coldwell Banker – Managing Director (1984–1988)

Notes from our interview

  1. Passion keeps you in the game. Real estate is cyclical. If you don’t love it, the down times will force you out before the good times arrive.

  2. Discipline means doing the boring work. Success comes from repeating the right actions over and over, even when they feel dull.

  3. Expertise is about focus. You can’t be a jack of all trades. Pick one thing, become the best at it, and make your name on that slice of the market.

  4. Your niche must balance scale and depth. It needs to be small enough to master completely but large enough to make a good living.

  5. Make yourself known. Send emails, make calls, meet people, share value. The business is not about who you know, but who knows you.

  6. Brokers:

    1. Product specialization now beats geographic specialization in brokerage. With public data everywhere, owners care more about your track record with their asset type than your general market knowledge.

    2. Every deal you close should feed the next one. If you’re pitching an office building owner, three office sales last week help. Selling retail or multifamily doesn’t.

    3. Define your value proposition clearly. What do you do? How do you do it? And is it easy to understand?

  7. Developers & investors:

    1. Treat brokers and your support system well. Relationships and information flow to the people who are nice and easy to work with.

    2. Give specific feedback. Don’t just say “not interested”, explain why. The more precise you are, the more intelligently brokers can serve you.

Bob is one of those rare people who speaks with genuine clarity. What do I mean by that? He wrote a book called Selling Buildings that I’d recommend reading. Talking to Bob feels like reading that book, the words line up. His spoken and written voices have complete parity. That clarity made this memo easy to write, and hopefully easy to read.

Call him what you want, realtor, real estate agent, broker, property surveyor, or Immobilienmakler if you’re in Germany. Whatever the term, Bob’s work speaks for itself. He has developed a reputation as one of the most accomplished figures in brokerage, combining deep market knowledge with an unwavering commitment to his clients. His track record places him firmly among the very best in the industry. Here's why I'm willing to make that statement: New York City has the highest total transaction values of any city in the world.

Playing in a market of this scale is what allowed Bob to achieve what he has. To date, he has been personally responsible for the sale of 2,358 buildings (generally considered the highest total ever for a single broker in New York) and more than $22.3 billion in transactions as of August 2025. To put that in perspective, Bob’s individual career equates to every commercial real estate deal in London in 2019. There is a very real likelihood that Bob has sold more buildings than any other commercial broker globally.

Advice for brokers

A quick note before we dive in: In my previous memos, I used too many quotes and didn't synthesize enough. It made them tiresome to read. So I'm trying something new here, synthesizing Bob's thinking into something more digestible. But let me be clear: these are Bob's insights, not mine. I'm just the messenger.

According to Bob, the top brokers all have three characteristics:

  1. Expertise

  2. Passion for the business

  3. Being able to use discipline

Passion is important because you need to love the business. Real estate brokerage is cyclical. The market goes up and down. There will always be tough times in a real estate career. If you don't love it, the business will grind you up and you'll get out during the tough times and not be able to stick around for the good times.

You have to be able to use discipline. Because so much of what brokers do is not exciting, but provided you're doing fundamentally the correct things, you have to do those things over and over again before they start to work.

Expertise is arguably the most nuanced of the three characteristics but also the most important. How do you become the expert? You have to know your market. And in order to know your market, you have to be able to clearly define what your market is and what your value proposition is going to be.

  • What are you going to do?

  • How are you going to do it?

  • Is it easy to understand?

You cannot be a jack of all trades in the brokerage business. You cannot do a little of this and a little of that and be known as the expert. You have to do one thing, become known for it, and do it better than anybody else. If you really want to get to the top of the business, you have to do that. That's a lot easier in a very big, dense market than it is in a tertiary market where you may be forced to do multiple things in order to make a good living. The caveat of the expertise thesis is that the slice of the market you focus on has to be small enough so you can understand every single thing about it but has to be big enough that you can make a good living doing it.

Consider Jim Collins' book Good to Great, which Bob references in his argument. Jim identifies the big difference between good companies and great companies. The great company decides or identifies what they want to do or think they can do better than anybody in the world. Every decision they make is geared towards achieving that objective. Identify what it is you want to do and what you want to become known as the best in the world at, and then study the market and understand it better than anybody else.

Picking your market

In the section above it’s fair to say that Bob is clear about the requirement to pick a market big enough to make a good living. Bob’s thesis around expertise is very market linked. There are really only two variables that are considered. Geography and product specialization. In order to increase the size of your market you have two choices.

  1. You have the choice of increasing the geography in which you do that one thing or

  2. Do different things within the geography you're comfortable with.

You should only be pulling on one of those levers if you want to remain an expert.

But here's the key insight: when Bob started Massey Knakal in 1988, publicly available information was minimal. Being a local market expert who handled everything in one neighbourhood was a competitive advantage. Today, with abundant public data, product specialization beats geographic specialization.

That rationale follows from the view that brokers have two main assets. They have market information (market intelligence, market knowledge). And they have their time. A broker is going to spend an entire career getting more market knowledge and studying the market so that asset is built into the profession. But time can be created. You can create time by using time more efficiently and effectively. I know, I said I was moving away from quotes but this one so clearly articulates Bob’s thinking, there is no need to paraphrase:

If last week I sold an apartment building, a retail property and an office building, and this week I'm pitching another office building owner, that owner wants to hear everything about the office building I sold last week. They couldn't care less about the retail property and the apartment building I sold. So two thirds of my time last week closing deals was not accretive towards getting this week's assignment. Had I sold three office buildings last week and I'm pitching an office building this week, 100% of my time is accretive towards getting this week's assignment. So I think product specialization is much more important today.

I think you have to layer on a geographic expertise as well. I can't say I'm the office building guy for the United States of America. But say I'm in the office building guy for Manhattan south of Canal street or between 60th street and 14th street or in downtown Brooklyn or wherever it is, you have a focus by product type with a geographic parameter. I think that's the most compelling strategy today for specialization, which again leads to the differentiation, which leads to the competitive advantage. So this time around, although I've been a generalist my whole career, I am now focused completely on ground up development and redevelopment opportunities, primarily in Manhattan. And that's what I'm doing to redefine my value proposition so that I can effectively create time.

For everyone else

Now it’s worth restating, I am not a broker. So I figured while I had Bob on the call, I should request that he direct his clarity of thought to the wider industry. I summarize Bob’s advice into a single bullet point:

  • Treat people in your support system well

Bob has a saying, “In real estate you’re not in the real estate business, you’re in the information and relationship business.” In order to succeed in your quests to acquire information and relationships, you will ultimately benefit from being nice and making yourself easy to work with.

The rationale for treating brokers is exceedingly clear but a lot of people in our industry could do with a reminder. Those who treat brokers the best are the ones who are going to get that call when there’s a limited audience. Be nice to the broker because broker controls the information. You want access to the information, so why would you alienate the broker?

Beyond treating brokers well, it’s about making yourself easy to work with. This stream of consciousness from Bob hits the point home:

It frustrates me when a potential buyer says "not for me" when I offer them a deal. That doesn't help me at all. It's like if you say to me,

"Hey Bob, I'm hungry," and I respond, "Would you like a sandwich?"

 "No." "How about a slice of pizza?" "No, I'm not interested in pizza."

"What about a panini?" "No, not interested."

"Well, what do you want?"

"Oh, I don't want any of those because I'm gluten intolerant."

If you had told me that after the first offer, I wouldn't have wasted time suggesting the other options. The same principle applies in real estate.

When somebody calls me and says, "Bob, I'm not interested in that deal," I need to know why. Is it because you don't like the location? Too small? Too big? Maybe in that location, the highest and best use is condos, but you only want to build hotels.

The more specific feedback you give, the more intelligently the brokerage community can interact with you. Be very specific about why you're not interested, it helps everyone involved and ultimately comes back to benefit you.

The general conclusion is, give those who are providing you a service the kindness to feel comfortable working with you and connecting you to other professionals and give them the information they need to serve you best.

Make some noise

The last piece of advice, again directed at brokers but applicable to those throughout the industry is one that Bob has been advocating for a long time. Anyone and everyone in this business, from the day they start in real estate needs to focus on market presence or in my words, make some noise. So on that note:

  • Go make your calls

  • Send your emails.

  • Write some texts.

  • Send hard mail.

  • Try and meet as many people as you can and stay in touch

  • Have something of value to give and share it with somebody.

And remember as Bob always says: “It’s not about who you know, but who knows you.”