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#takethewheel with Mr. Todd DeSimone

In our third installment of #takethewheel, we pass the torch to Mr. Todd DeSimone, a longtime friend and customer of Rivay and growing Porsche enthusiast.  When he's not helping to shape the New York City skyline in his role as general counsel to a construction management firm, you can find him on a back road somewhere north of the city stretching the legs of his flawless 1988 Porsche 911.  

Sit back as Mr. DeSimone dissects why he loves his job and what's next on his classic car wish list.

Tell us about the day job:

Todd DeSimone (TD): I am the Vice President and General Counsel of a large construction management company here in New York City. My daily activities run the gamut really, one day I am dealing with an HR issue and the next I am fighting with an adversary over how to interpret a contract provision. The majority of my time though is spent negotiating hundred million dollar construction contracts and working out business terms with my partners. I can honestly say, and for a lawyer this is really saying something, I absolutely love my job; it could not be more stressful but my colleagues are best in class at what they do and we are contributing to the New York City skyline in a really meaningful and important way.     

Go ahead and take a picture of your keychain…


Tell us what we’re looking at here?

TD: Beyond the pile of contracts and other work-related items, you see here the keychain and the key to my “daily driver,” a Range Rover HSE. The keychain is an old Tiffany’s keychain that I must have had for 20 years now; so at this point, I cannot get rid of it.  I think it may have been a gift from my mother when I graduated college or something. The Range Rover is a real pleasure to drive, it’s ludicrously large, but it somehow manages to handle like a sports sedan and it has these windows that are double the thickness of a normal automobile window which make it absolutely silent on the road, even driving at high speeds on the highway.    

What other vehicle(s) do you own?

TDRight now I have a really nice 1988 Porsche 911 all-original, the FUCHS rims, the whale tail, the whole bit. I am also working on getting a Defender 90 at some point in the indefinite future. There is just something about that truck I am drawn to and it’s just gotta happen. Copley Motorcars up in Massachusetts have some really nice examples with low mileage and I check their site monthly looking for just the right one. Pure happiness to me will be when my wife, daughter, dog and I can ride in the D90 with the top off on the way to Ladies Beach in Nantucket.    

What drew you to the 911?

TDIt was a serendipitous situation really. I was over at a family friend’s house in upstate Connecticut. This guy likes his toys right, he’s got all sorts of cars, bikes, water sports, etc. Anyway, I see peeking out of this old barn on his property the end of the whale tail of the Porsche. You have to understand, I was in my prime adolescent years when that car came out, I had a poster on my wall of this car when I was ten years old. So that was it, I was hooked. It was in perfect shape and he never drove it. I made a deal with him that day and drove it off his property.    

What do you love about driving it?

TDIt really takes me away from the everyday stress of life, even if for only an hour on a Saturday morning. Look, I have a stressful job, a family, a super jumbo mortgage (that’s what the mortgage company actually calls it by the way, if you can believe it), obligations and responsibilities all over the place.  But when I slide into the Porsche and find a back country Westchester road that deserves exploring, that’s my time, no stress, no worrying, sheer relaxation. And the cars in the 80s, they were not made like new cars where you barely know you are driving it; you truly connect with vintage cars when you drive them - the manual transmission, the exhaust, the RPM dials, you are really engaged and the car and you are working together to make a memorable experience.

Rivay take the wheel

Rivay take the wheel

Rivay take the wheel

Rivay take the wheel

What’s the one thing you dislike about driving it?

TDIt might sound strange but the same things I love about driving it - the inconveniences, bad stereo system, no cupholders, when you hit a pothole it feels like you just had a colonoscopy.

Have any other toys we should know about?

TDNot yet but working on it.

Have your eye on anything else?

TDOther than the Defender 90 that I mentioned, I really like the 1970’s Triumph TR-6’s. They probably live in the shop, maybe I am a glutton for punishment but they just have this very handsome, refined look to them. The idea of taking my wife out to dinner in one on a cool Fall evening is pretty exciting. I would also love a 1995 Range Rover Classic. It was the last year with that “safari” looking body and they had the nice update with the soft dashboard. A friend of mine in Rowayton, CT acquired a really nice condition one from someone in the Pacific Northwest, he put a 2” lift on it, black steel rims, a roof rack, Hella lights and factory brush guard.  Thing looks like it’s out of Jurassic Park or something. 

What’s the dream car?

TDTough call, lot of dreamy cars out there.  If I was going for broke, I would say a 1960’s SWB 275 GTB Ferrari.  The curves on those cars are just amazing, it looks like it was imagined by Tom Ford or something.  Perfection.

Car you most regret selling?

TDNothing yet.  

Rivay take the wheel

Rivay take the wheel

Rivay take the wheel

Rivay take the wheel

You have one hour to escape, what do you do?

TD: Throw on my running shoes and get on the wooded trail that backs up against my house.

Now you’ve got 2 weeks?

TDMany years ago a friend and I traveled from Dubrovnik, Croatia to the capital of city of Zagreb. Croatia has these really great (and surprisingly affordable) ferries that run all up the Adriatic Coast. You just hop on and off as you please and see these beautiful old beach towns that are just being re-discovered by Westerners again in the last 10 years. It’s like Italy in terms of people, food quality and cafe culture without the tourist groups and American menus you find on the Amalfi Coast.

Favorite trip not yet taken?

TDI would really like to explore South America - Buenos Aires, Patagonia, Punte Del Este.  

The hotel that feels most like home?

TDThe Franc Mayne Chateaux in Saint-Emilion, France. It’s in the Bordeaux region of French wine country. My wife and I spent some time there right before we got married and we still talk about it. The wine was outrageously good and the hotel rooms had all the modern conveniences you need even though you are staying in this centuries old chateaux. In the mornings they lay out this ridiculous buffet of all the meat and cheese you could ever eat with fresh eggs and veggies from the farm next door. Just a perfect place, really.    

You can teleport to any bar in the world right now - where to?

TDThere is this perfect little bar at the Summer house in Nantucket.  It’s right on the beach - solid drinks, great people and they allow dogs.  It’s just a very relaxed and upbeat atmosphere looking over a gorgeous beach. I have never not had a great time there wasting away a few hours with friends drinking and usually accompanied by my french bulldog.

What’s your drink?

TDIn the summer, Negronis; in the winter, dirty martinis.

What will we always find on your nightstand?

TDMy phone, books, magazines and some sort of toy that my daughter considerately left there for me.

The one item you are never without?

TDI try and be free from items/devices as much as possible, but for work I always need to be reachable, so my cell phone is always within reach.

Your favorite travel hack?

TDThree rules: (1) never spend more than three nights in Las Vegas; (2) London is always a good idea; and (3) leave the diet at home.

Where’s your hometown?

TDI grew up in Northern Westchester - Pound Ridge. Beautiful area, lots of horse farms and sleepy old towns that have been around since the 17th Century.  

Place we’re most likely to find you if we’re looking?

TDMy office in Midtown or a construction site.

Place we’d never find you?

TDChain restaurants.  An Applebee’s - my nightmare.

The road you drive to take your mind off things?

TD: Route 121 or 22 in Westchester County.  

What’s on the wrist?

TD:Rolex Datejust.

Canon or Nikon?

TD: I have a Canon but I usually get lazy and just use my iPhone.

Diesel or Gas?

TD: Gas

Rocks or neat?

TD: Negroni (rocks), Dirty Martini (neat), good bourbon or scotch (one ice cube)

Last google search?

TD: Best orchards to take your family in October

Biggest risk ever taken?

TD: Leaving my single life. Best decision ever.  

Rivay take the wheel