Miles Nadal is now a shoe collector and capital allocator

An update on Miles Nadal of Peerage Capital and Peerage Realty and previously, MDC Partners.
OPM 8 min read

I wanted to write about Miles Nadal because I get the impression he’s starting to be more public these days. Like he was speaking at Anthony “The Mooch” Scaramucci’s SALT conference earlier this month. I assumed I would need his collaboration to write something that adds value. Unfortunately, Miles did not want to collaborate. That was probably a stroke of luck, because it gives me a “freer hand to write”, if you catch my meaning. Despite having no access to him, I believe I have put together the most comprehensive psychographic profile of Miles Nadal ever written. Or of any businessman for that matter. It was pretty easy too. Here are his strengths and weaknesses:

Strength number 1: he’s a calculating communicator

Many self-made people strategically drop hints about their humble beginnings. The media loves this sort of narrative arc. But I have never heard anyone tell the tale with as much specificity or practice as Miles Nadal. It is vitally important that you know that he grew up in a 900 sq. ft, 2 bedroom, 1 bathroom apartment. His parents’ combined income was $10k. He got subsidized to go to summer camp at the Jewish Community Center (now, the Miles Nadal Jewish Community Center). Rather than getting a break from his parents, he actually employed them in what he calls a “reverse family enterprise.” I fall for such stories as much as the next guy, but alternative narratives would be just as valid. You could have wealthy but inattentive parents. Or your parents’ wealth could shoot down any natural incentive you might have. Anyways, Miles clarifies that the fact his family lived in wealthy Forest Hill is misleading as “they didn’t have the same financial security as their neighbours and his parents had to work hard to give their sons opportunities.” You might wonder: did Miles live in that 900 sq. ft. apartment continuously from age zero to 18? Was $10k his parents' average earnings or peak earnings? You ask too many questions. And make no mistake, the apartment was a rental. Bottom line, if the “Started from the bottom” rapper Drake, who was also raised in a Forest Hill rental, wasn’t himself Jewish, Miles Nadal would be the Jewish Drake.

Strength number 2: he’s versatile

Miles is totally with it. He has 10k followers on Twitter. He’s clearly a relentless learner and has his finger on the pulse. He has touched a lot of different areas of business (cheque printing, marketing, money management, real estate, etc.). Miles managed to turn a photography business he started in high school into a globally relevant advertising holding company, MDC Partners. ROI for shareholders very much depended on when you bought in and whether you were the CEO or not. His big bet now is an acquisitive luxury real estate brokerage platform called Peerage Realty. Peerage Realty made some of its most aggressive moves in the past few years, becoming a top 10 player in North America, so let’s see how it fares in the downturn.

Just as one example of how Miles really keeps up with trends: in 2019, he started collecting sneakers. 300 media outlets around the world reported on his first big purchase of a shoe collection. When Imelda Marcos loots her people and buys thousands of shoes, that’s considered crazy behaviour. But if a man spends seven figures on sneakers, he’s pioneering a new asset class. That’s plain old sexism!

Miles' muse.

Strength number 3: he’s a shameless copycat

Miles Nadal has said he’s a professional plagiarizer. Being a copycat is a positive in my book. I wrote a really long essay called The Second Mouse Plan about why it’s better to be a follower than a pioneer. (Because the early worm gets eaten, while the second mouse gets the cheese.) Quite often, Miles credits someone else as the inspiration for something he does. He decided to build a serious car collection after meeting Jay Leno. MDC going public via a reverse takeover, was inspired by Martin Sorrell taking over WPP, eventually the world’s number 1 advertising agency. Miles’ career has been mostly about acquisitions rather than starting things from scratch, which is also very second mouse. He is a big fan of Warren Buffett, the ultimate second mouse.

If I have one bit of scoop, it’s that I contend that Miles Nadal is semi-retired (just like Buffett says he is). Consider the governance of his major holding Sotheby’s International Realty Canada. That company has a CEO, Don Kottick. Sotheby’s is housed under Peerage Realty, which has its own CEO, Gavin Swartzman. Peerage Realty is a subsidiary of Peerage Capital, which has its own CEO, Trevor Maunder. So that’s three layers of CEOs before you get to Miles Nadal, who is Executive Chairman of Peerage Capital. Miles Nadal himself has said that he now mostly controls the chequebook - ie capital allocation.

Acquisitions are good as long as you acquire something of enduring value. MDC bought a lot of “hot” advertising agencies. When I review that history, their acquisitions often burned hot like popular nightclubs. Miles is now involved in businesses with much better economics. Real estate brokerage is a business blessed by Buffett. Berkshire’s HomeServices division is the blueprint for Miles’ Peerage Realty. Closer to home, Jay Hennick made a lot of money consolidating various Colliers regional brokerages around the world. Just like how Miles is now a serial acquirer of Sotheby's realty franchises. Incidentally, Miles is a partner with Jay Hennick and real estate investor Peter Cohen in a land assembly / development venture called Trolleybus Development. Miles is also involved in a self-storage venture, Vaultra Self-Storage. Land and storage space, what could be more down-to-Earth? Plus, Miles also claims that his famous appetite for leverage has come down.

Strength number 4: He’s trying to be even humbler than he already is

There’s no need to re-hash the ups and downs of Nadal’s business career, those have been well documented. In a 2019 article on his growing shoe collection, the New Yorker felt the need to mention that the SEC banned Miles from serving as an officer or director of a public company for 5 years. That ban, matched by our own very alert OSC, has lapsed as of May of this year. Somehow, Miles Nadal collaborated with the New Yorker, even though they chose to bring up the fact that he failed to disclose some perks he had as CEO, “including cosmetic surgery, jewelry, pet care, and yacht-related expenses, totalling more than eleven million dollars”. As a serious but easily manipulable journalist, I would have never dredged up those old details. His exit from the company he founded and led for 35 years was rather abrupt. Not unlike the end of the Marcos regime. On this episode, Miles has said: “I learned that you can never be too humble.” Wow! It’s humbling to think that the Michael Jordan of humility still sees room for improvement.

Let’s pause to play a game: Who said the following, Miles S. Nadal or Donald J. Trump:

I’m highly numerate, I understand deal making, I understand the capital markets very well, and I know how to create a sense of urgency to capitalize on opportunity in a controlled way to get things done that most people are not possibly as effective as I am at

Just like Trump, Miles Nadal has many things named after himself, but his proudest achievement is his two daughters, The Miles Nadal Daughter No. 1 and The Miles Nadal Daughter No. 2. To be fair, most of the naming was due to Miles Nadal’s philanthropic activities. He says he has given away $60m over the years and that he’d like to give away another $120m in his lifetime.

Strength number 5: he’s a master networker

You have achieved true anonymity on Bay Street if you have never received an invitation from Miles Nadal to connect on LinkedIn. He has LinkedIn friends at every level of Bay Street, from lowly analysts and up. At the peak of his career in advertising, there were few Canadian business people who were as relevant on the Manhattan scene as Miles Nadal. You will see pictures of Miles Nadal with everyone from Bill Gates to Ivanka Trump to Roger Federer to Bill Clinton to Puff Daddy. Last month, finance god Michael Milken visited Miles’ car museum. But forget these attention-whoring celebrities, Miles Nadal managed to get a photo with the highly reclusive founder of OPM Wire, NoBull Klev! It was at a book launch he hosted for Andrew Ross Sorkin. I can guarantee I wasn’t the one who asked for a photo, because I consider that an imposition and you know how I don’t like to bother people. This shows how Miles Nadal genuinely loves connecting with people at all levels. I hope this is a pathology he can one day overcome.

Miles Nadal appears not to be merely a transactional networker either. He seems to have had decades-long associations with team members, such as his very first assistant. Trevor Maunder and Stephen Pustil are two other longstanding associates with executive roles. About 20 years ago, MDC Partners bought a stake in a white hot advertising firm called Crispin Porter + Bogusky. This is the transaction that put MDC on the map. Crispin today is shadow of its former self. But just last week, Crispin co-founder Chuck Porter was at an ad shoot for Peerage Realty. I’ll be honest, my psychographic model would not have predicted such loyalty! And that’s because my psychographic model very much predicts that Miles is easily bored with everything.

Of course, strengths can also be weaknesses.

Weakness number 1: he wants to be loved

Why is it that some people are perfectly happy being hermits, while other people constantly want to socialize? Miles Nadal wants to be loved. He wants to be validated. He needs to be admired. Many of his social media posts are representative of the dominant current of that art form, "conspicuous living". In other words, lots of posts that are variations of “look at my fabulous life” (look at my expensive trip, look at this important person I know, look at my perfect family, look at my cottage life, etc.). Why? Of course, you might say that everyone wants to be loved and admired. It’s a question of degree. A more sophisticated diagnosis would be to say that Miles has a very high need for stimulation and that people are his stimulant of choice. But he also binges on deals, material possessions, etc. He has multiple residences so that he can frequently change his environment. I could go on, but I don’t want to get too personal because I fully expect that Miles and I are going to be pals. That’s because I am being less than 100% reverential, so he’ll obviously be desperate to win me over. I am prepared to meet him half-way by feigning an interest in cars.

Weakness number 2: none

Miles Nadal has no other weakness. You might think: how about the SEC thing, isn’t that an example of short-sighted greed? That’s not a separate weakness, everything can be traced back to a desire to be loved and admired. If a man buys a sports car in middle age, people wonder what’s he compensating for? Miles has at least 130 cars and 700 pairs of shoes in a garage/museum in Toronto he calls Dare to Dream. I don’t want to be too judgy, but come on, what’s going on, you know what I mean? My best guess is that it’s the peer group effect: people are not envious of King Charles, even though in absolute terms, he’s wealthier. People are envious of their neighbour with a slightly better car. Miles is a centimillionaire who hangs out with billionaires. This is just like when he was the relatively poor kid in wealthy Forest Hill. This explains everything. Disclaimer: I am not licensed to practice psychoanalysis.

What does all this whirlwind of activity, hobnobbing and dealmaking add up to? Is Miles Nadal worth $200m? $300m? Not $500m? It’s a key question I was going to ask him, but sadly, given Miles’ newfound aversion to publicity, we will never find out.

Finally and perhaps most importantly, if you still have any lingering doubts about the whole Forest Hill situation, please understand his mom worked for the rental company, so the rent was cheaper than it otherwise would have been. Drake’s mom, on the other hand, went into heavy debt to afford a Forest Hill rental. And that's why Miles Nadal will never be a truly great rapper.

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