The Flatiron District

In 1996, Jerry Colonna and I decided to call our venture capital firm Flatiron Partners (it was code named Acme Ventures). We named it after the Flatiron Building and decided to locate in the neighborhood with the same name. We moved down there a bit later and I immediately was smitten with the neighborhood. I have made my office there ever since. It’s twenty years now.

The thing I immediately noticed about the Flatiron district upon moving there was that it was unlike midtown manhattan, where I had worked for the previous ten years. The Flatiron district was about half residential and half business. And the businesses ranged from small photo studios to fledgling internet companies to accounting firms and therapist offices. The building that USV is now located in was full of photo studios in 1996. I don’t think there is a single one left.

The other thing that I love about the neighborhood is that it stays open late. The streets are full of restaurants, cafes, and bars. I can leave my office at 11pm and wander into any one of the local spots and they are still humming. That was true when we arrived in 1996 and it remains true today.

Working in the Flatiron district is like working in a residential neighborhood. You have grocery stores, dry cleaners, bodegas, and preschools. When you walk the streets, you see strollers and couples holding hands.

I thought of the Flatiron district when I read this MIT Technology Review article about a follow up study to Jane Jacobs’ seminal work on the vitality ofΒ cities by some University of Toronto researchers. The new work is called The Death and Life of Great Italian Cities: A Mobile Phone Data Perspective. These University of Toronto researchers used mobile phone data supplied by our portfolio company Foursquare and a few other data sources to study the vitality of a number of Italian cities.

Jane Jacobs says that for cities to thrive they need four conditions:

The first is that city districts must serve more than two functions so that they attract people with different purposes at different times of the day and night. Second, city blocks must be small with dense intersections that give pedestrians many opportunities to interact.Β The third condition is that buildings must be diverse in terms of age and form to support a mix of low-rent and high-rent tenants. Finally, a district must have a sufficient density of people and buildings.

The Flatiron district is the perfect example of Jane’s four conditions. I bump into people I know and don’t but should literally every day on the streets of the Flatiron district. It’s a mixed use neighborhood and though it has been gentrified a lot in the past twenty years (rents have gone from $15/sf to $75/sf in some buildings over those twenty years), it remains as vital today as when we arrived. I’d like to see the Foursquare data on the Flatiron district. I suspect it would be off the charts on the Jane Jacobs score!


Comments (Archived):

  1. JimHirshfield

    Yes, great neighborhood. Have enjoyed working there over the years. Off to Toronto this afternoon for my first time ever. Looking forward to it.

    1. fredwilson

      great city. would score well on Jane’s conditions.

      1. JimHirshfield

        Yes. It was cited in the MIT Tech Review article you shared. Unfortunately, William’s not around to show me the city. He’s got books to write.

        1. JamesHRH

          Try Hopgoods Foodliner if you are on the west side of downtown at all.

        2. William Mougayar

          + just recovering from 42 hours with no power. dreadful life.

          1. Brandon G. Donnelly

            that’s what happens when you live out of the city πŸ˜‰

          2. William Mougayar


          3. JimHirshfield

            Canadian frontier life is haaarrrrd

      2. Brandon G. Donnelly

        she certainly had a hand in building (and not destroying) this city.

      3. kirklove

        Jane moved there later in life πŸ˜‰

    2. Brandon G. Donnelly

      welcome.where are you staying?

      1. JimHirshfield

        Thanks. Yorkville neighborhood

    3. William Mougayar

      you’re staying in a “busy” area. walk west, not east πŸ™‚

      1. Brandon G. Donnelly

        what is a “busy” area?

        1. JimHirshfield


          1. JamesHRH

            Yorkville is as high end as Toronto gets.

          2. JimHirshfield

            Excellent. I like a high end.

        2. William Mougayar


          1. Brandon G. Donnelly

            you’re right. better to walk west πŸ™‚

          2. Supratim Dasgupta

            Yorkville Manhattan?

  2. Mike Zamansky

    This post reminds me of Tom Shachtman’s “Around the Block: The Business of a Neighborhood” (…Where he looks at a single block in NYC – 17th to 18th street, 7th and 8th ave as a community.Worth a read if you can get your hands on it.

  3. Sebastien Latapie

    That is one of my biggest gripes about living in Boston – it does not stay open late! It’s lacking that vibrancy and energy you can find in so many neighborhoods of NYC.

    1. fredwilson

      Its been 33 years since i’ve lived in Boston but I imagine that the student neighborhoods around Kenmore Square, Kendall Square, Harvard Square, and Central Square are buzzing late at night

      1. Brandon G. Donnelly

        i was once in boston by myself and walking around at night looking for a place to go. i stopped someone on the street and asked him where i should go to grab a drink.his response: “new york”

        1. Daniel De Melis

          Downtown Boston is great. Honestly; I’ve been twice. Funny running into you in this blog :). I’ve learned to really enjoy it reading it!

      2. Sebastien Latapie

        I wish! I’m living right by Kendall – while not completely dead, its hard to find a busy bar / cafe anytime past 10:00 pm during the week. Hopefully its just the winter blues and people will be out and about once spring has sprung

    2. Ana Milicevic

      Boston is a little tougher since, up until a few years ago, it completely missed the young professional crowd — you were either in college or mid- to late in your career. It’s changed a lot in the last 15 years and oddly the areas around colleges aren’t what’s driving activity; since you’re on the Cambridge side pop over to Davis Sq (I liked Spoke) and Union Sq (Casa B is awesome). A bit more mixed housing there, a bit less of a clinical feel and more interesting life stuff all around.

      1. Sebastien Latapie

        Union square is definitely on my radar! So many great restaurants and bars opening up in that area (back bar is great).

  4. karen_e

    Her ideas are still very much in mind for working urban designers. For example, trying to make the brand-new cities in the Gulf region more pedestrian-friendly as they grow. How? Passive cooling by pushing the cool air created by air conditioners into the sidewalk areas, multiple small parks–sometimes separate ones for men and women. The designers I know might not agree with everything they come up with, but they’re trying to nudge the cities in a Jane Jacobs direction!

    1. Brandon G. Donnelly

      one of the biggest city building challenges, i think, is taking car oriented suburban environments and making them friendly to pedestrians. what’s a bit frustrating though is that these are “brand-new cities” that had an opportunity to do that from the outset πŸ™‚

      1. Ana Milicevic

        That’s a really interesting point – most if not all of the cities that are walkable, livable, etc owe it to their pre-car roots.

        1. Brandon G. Donnelly

          oh absolutely.urban form has always been impacted by mobility — from “streetcar suburbs” to today’s car oriented suburbs.but none were as disruptive as the car.

          1. Ana Milicevic

            I dream of a Manhattan w/o cars

          2. Drew Meyers

            I dream of everywhere without cars (I don’t have one in seattle)

      2. karen_e

        It is teeth-gnashing to say the least.

    2. Ana Milicevic

      If successful, that’ll drive such massive behavioral and cultural change.

    3. JLM

      .An interesting phenomenon to study and follow is the success of open air shopping centers in the South — as opposed to air conditioned enclosed malls.These properties with street level retail, offices and apartments above with structured parking garages behind them are like cities unto themselves.When they first began to be built, traditional mall developers scoffed at them but not anymore.The $7-12/SF advantage in operating expenses (no air conditioning, artificial lighting) and the vitality have made them the new thing.Great design, short blocks, public spaces, a fabulous tenant mix of goods, services, food. All the keys to success.JLMwww.themusingsofthebigredca…

      1. TeddyBeingTeddy

        Have you been to the one in downtown Charleston, the city market? fits this description to a T, but always a bit awkward because you’re buying shirts at the same place where they used to sell people.

        1. JLM

          .I have spent a lot of time in Charleston and I usually stay at the Planter’s Inn across from the “slave market.” (Best 7-layer coconut cake in the history of mankind at the Peninsula Grill at the PI).Not quite the same thing I’m talking about.When I am in Charleston, I often close my eyes and see if I can feel the angst that was created there. Supposedly the most haunted American city. I like ghost stuff.The Civil War was started in Charleston and it was the stupidest war in the history of some really stupid wars.It is hard to believe that all that stuff really happened.JLMwww.themusingsofthebigredca…

      2. Matt Kruza

        Are you saying they have a $7/12 operating advantage PER YEAR??? I would have guessed much closer to $2-4, which will big, is much different. Any data to back up the $7/12 operating difference per year? Not doubting, but just much larger than other calculations / anecdotes I have heard so curious!

        1. JLM

          .$7-12/SF — so a 10,000 SF tenant is paying approximately $100K more per year to be in an enclosed mall plus the attribution of their prorata share of the mall common area.The tradeoff is the supposed power of the tenant mix — fewer competitive products/retailers as the tenant mix is controlled by the landlord — and the amount of traffic based on siting. A shoe store at the entrance of Nordstrom which carries different lines of shoes than Nordstrom can have a very vibrant business, indeed.A mall is air conditioning/heating, lighting an enormous amount of space which one would not have in a shopping center.This has been going on for years. It is quite common knowledge.JLMwww.themusingsofthebigredca…

          1. Matt Kruza

            Hmm interesting. I get everything you said, just surprised by the rate, seemingly double or more cost for indoor. I know some people who have run many malls in the midwest, and I wonder if lower air conditioning cost here is the main difference? Either way appreciate your perpsective

  5. Brandon G. Donnelly

    fantastic post. i love seeing technology infiltrate other industries/disciplines. and in this case, we have classic jane jacobian theory meeting social apps. imagine now overlaying rents with these vitality scores. i bet you could make a really strong case for sound city building.

  6. natsturner

    We’re moving Flatiron Health there (to Eately’s building, 200 5th) next Monday! (yes, back to our namesake)

  7. TeddyBeingTeddy

    Fred how did you decide what neighborhood to live in. I suspect living in NYC you run the risk of your kids being like the kids from the movie Kids. Or you could live in the north shore of LI; no crime, end game lifestyle, but run the risk of entitlement. How do you apply the data to the optimal place to raise a family, assuming you had the option to do it anywhere in NY?

    1. fredwilson

      greenwich village. the home of jane jacobs.

      1. TeddyBeingTeddy

        Be honest, you just wanted to be close to Johns Pizza. I don’t blame you…

  8. William Mougayar

    My favorite cities list: Vancouver, Paris, London, Rome, Beirut.

    1. Supratim Dasgupta

      No New York ;-( sniff sniff! And also no Toronto?

      1. William Mougayar

        Nope !

        1. Daniel De Melis

          Why not Toronto?

          1. William Mougayar

            I like charm in a city or where I live. I’m outside of Toronto in the country & I love it. There are more horses, cows, trees, ponds and wild animals than people 1 sq mile around me.Toronto is a cold city, compared to NYC, Paris, Vancouver, London, Rome, Beirut.

          2. Daniel De Melis

            Fair enough. I think Toronto is warming up now.

    2. Matthew Zadrozny

      Could you explain the appeal of Vancouver?When I visited a few years ago — admittedly, in the dead of winter — I was unimpressed. Very brutalist, packed with American chains, no discernible civic culture. By contrast, Seattle struck me as very similar geographically, but with nice architecture and a strong grass roots vibe.

      1. William Mougayar

        I lived in both cities. Vancouver: water + mountains at proximity. It depends what part of Vancouver. Most liveable city for decades.

  9. kirklove

    Robert Hammond from the High Line is working on a Jane Jacobs documentary. I was able to see an early screening. Fascinating stuff. It’s really Jane vs Robert Moses. Astonishing contrasts. Glad she won a few of the battles and we don’t have super highways running through lower Manhattan.PS: “…. I can leave my office at 11pm and wander into any one of the local spots and they are still humming.” – except Coffee Shop of course ;p

    1. Ana Milicevic

      That sounds really cool. If you come across other early screening opportunities please send them my way – I’m super-interested in seeing that.

      1. Brandon G. Donnelly

        me too :)on a related note, i really like how bjarke ingels is positioning new york’s “dryline” as being the love child of jane jacobs *and* robert moses.

        1. Ana Milicevic

          Interestingly I find his philosophy to resonate more with me than his actual work (esthetically I’m more in the Renzo Piano and Santiago Calatrava camp). Initially I thought he was off his rocker to classify the Highline in such a way (but I had the benefit of seeing it over a very long period of time – from eyesore and star of ‘where to dump the body in Law & Order episodes’ to an actual urban space I’d enjoy using). Now that it’s been around for a while and I use it almost daily I hate that I’m changing my mind: it’s become more of a tourist thing to check off than a living, breathing part of the city. He was right.

          1. Ana Milicevic

            Oh, duh! I should read better :)My love/hate relationship w/ Highline still stands though. The Dryline conversation brings up another interesting point in design: what should cities be doing preemptively to protect against climate change? And at what scale?

          2. kirklove

            Ana,I’m working at the High Line now. I’d love to show you how we’re working to change the perception (which is valid in some respects) that the HL is just a tourist spot. Start here:

          3. Ana Milicevic

            Thanks – that’s an impressive list! Would love to learn more about what you’re working on – grab a Highline coffee?

          4. kirklove

            sure – hit me up kirklove (at)

          5. Kirsten Lambertsen

            Wow, that video was just super neat. Great share!

    2. fredwilson

      never ever gonna step foot in that place again.

      1. Vasudev Ram

        set foot, I think it is.

  10. pointsnfigures

    Quote from a review of the book: “According to the author, the mess we call cities today emerged from Utopian visionaries from Europe and America beginning in the 19th century. Figures such as Ebenezer Howard, Lewis Mumford, Le Corbusier, and Daniel Burnham all had a significantly dreadful impact on how urban areas are built and rebuilt. These men all envisioned the city as a dreadful place, full of overcrowding, crime, disease, and ugliness. Howard wished to destroy big cities completely in order to replace them with small towns, or “Garden Cities,” made up of small populations.”Totally find that interesting since Burnham planned Chicago. One of the things I like about Chicago is the open space. Yet, because of public transportation and ease of walking it’s pretty simple to navigate. It does have less energy or juice than NYC; but I think that has more to do with volume of people and weather. Post Chicago fire, Chicago city planners put a strict height limit on buildings out of fear with NYC didn’t. Hence, even though the skyscraper was invented here, the really big ones were built in Manhattan.

  11. Ana Milicevic

    I grew up in cities that were decidedly mixed use, walkable and buzzing at all times of the day and night (sometimes too buzzing!). Grocer on every corner, restaurants, coffee shops on every block, walk to public transpo, school within 20 mins walk – that kind of thing that maps perfectly to Jane’s conditions. Vividly remember the culture shock and feeling so out of place the first time I was in Los Angeles where you had to get in your car to then go and get a cup of coffee. I couldn’t then and largely still don’t understand that type of lifestyle (although I’ve since discovered parts of LA that agree with me).Flatiron is such a beautiful connector neighborhood. Reasonably easy to get to from anywhere else in the city, every subway line goes through it, and the streets are wide enough to effectively walk around the skyward-gazing tourists πŸ™‚

  12. Tom Labus

    It’s my favorite part of the city. The walk on 5th from 23rd to Washington Sqaure never gets old. I rarely go to Midtowm anymore. It’s like two different cities.

  13. bijan

    I love the Flatiron area. I don’t feel like it gets the credit it deserves compared to other parts of the city.The residential + business combo is the best. Makes life so much more interesting and part of the reason Lauren and I have getting out of the burbs high up on the master plan πŸ™‚

    1. Brandon G. Donnelly

      would you move into the city with the kids?

      1. bijan

        yes, but which city is still up for debate πŸ™‚

        1. Brandon G. Donnelly

          would love to hear about the thought process and the ultimate decision. i hope you blog about it πŸ˜€

    2. Paul Sanwald

      I think it’s slightly under the radar because you need to either live or work there to appreciate it. I didn’t spend much time in flatiron before we moved our offices there, but I really came to love it (especially stopping by eataly for fresh pasta to make for dinner on the way home from work).

  14. David Lee

    Great post, as always. Where do you think LA fits? My hunch is that the random interactions caused by geographic density is less important when we’re all connected via phone? Thus that bodes well for LA where density has been a weakness or I’d argue a strength (or not the weakness it once was)

    1. TeddyBeingTeddy

      LA is way too spread out. You can get from one end of NYC/Chicago/SF to the other in minutes with public transit, foot, etc. LA is a nightmare that way.

      1. David Lee

        Yeah historically you’re on point. LA is trying to fix this though!

        1. TeddyBeingTeddy

          I’m not sure LA will ever fix it. Folks there are so caught up in image, they wouldn’t be caught dead in public transit. They want to be seen pulling up to the Beverly Wilshire in a nice car. It’s just not conducive to what this article is saying, it’ll always be crazy spread out I think. But glad they’re trying at least…

          1. Andrew Yao

            I moved from a Flatiron only existence – lived at 15th and 5th, worked at 11 Madison Ave, to Santa Monica. I hate driving and I’m not really into fancy cars. You probably don’t need a car in Santa Monica or Venice, but the density of public transport stops doesn’t support the access to other parts of the city. I miss walking past all the Flatiron spots previously mentioned everyday.

    2. Brandon G. Donnelly

      we’ve been talking about technology eradicating the need for physical proximity for a long time. tech certainly connect us, but i’m not convinced that it makes urban density less valuable. in fact, some argue the opposite.

      1. David Lee

        Yeah you’re probably right. I’m in LA and would love this to be the counter example!

    3. fredwilson

      there is a reason that downtown LA has become so vibrant in the last five years. i think it will show LA the power of live/work communities where you can walk. Venice and to a lesser degree Santa Monica are already there

      1. David Lee

        True dat. There are shades of what’s happening there and Flatiron? I was in NY in late 1990s so I saw some of what you’re referring to and would love to see a similar resurgence in downtown

  15. jerrycolonna

    I still love working there. Despite having moved to Boulder, I just re-signed my lease for my office there.

    1. fredwilson

      wow. that’s commitment

      1. jerrycolonna

        Despite my love of Boulder, I remain a New Yorker. πŸ˜‰ Plus, that spot’s become a core presence for Reboot (we’ve four coaches working there). So, yep, another five-year lease.

        1. Supratim Dasgupta

          A New Yorker will always remain a new yorker.

          1. jerrycolonna

            always. πŸ˜‰

  16. iggyfanlo

    You’re a lucky man. I moved into a 2 bedroom condo with my brother on Labor Day 1983 in the Madison Green Bldg on 5th & 22nd opposite the FlatIron… but at that time, Madison Park was renowned as the worst drug den in Manhattan. Times have really changed… and all for the better

    1. fredwilson

      the gotham gal and i lived at 28th and madison from 1983 to 1985. the neighborhood was worse north of the park than south of the park. we had all the welfare hotels and hookers on our block

      1. iggyfanlo

        I was mugged twice in NYC in my 20 years there (83-03)… once at Union Sq North subway station and once on 23rd between 5th & 6th… that was always an eerie block to me… the hairs on the back of my neck always went up walking down that block… it was on the walk to a Knicks game

  17. MTLinville

    @fredwilson:disqus, I’d encourage you to check out @MarketUrbanism on Twitter from NY-focused, market-oriented urban design commentary if you haven’t seem them before. Lots of good stuff on how to ensure NY remains vital for people from all walks of life.

  18. Semil Shah

    Based on Jacob’s definition, I am not sure most of SF would qualify — but much of LA would.

  19. JLM

    .The single most important value for the development of any urban environment is safety.I recall with great clarity how Central Park became dangerous and then how it was made safe. It made a huge impact on the allure of NYC.The area around the Flatiron Building had a similar history and its vitality is, in no small measure, also a testament to its changed public safety environment.If you don’t have safety, you are reluctant to move about and the hours of darkness become the hours of no movement.JLMwww.themusingsofthebigredca…

    1. Tom Labus

      It’s a good point. I’ve never seen the city this vibrant with new construction all over but especially the West Side. The High Line has had such a positive impact and is always packed with walkers.

  20. Vasudev Ram

    Since relevant, I’ll put in my occasional mention of E. F. Schumacher and his book Small is Beautiful:…As I said on HN recently, he and Gandhi were doing this sort of stuff decades ago.

  21. Vasudev Ram

    Laurie Baker also did related stuff, in India. Use of traditional / natural materials and methods for building construction.

  22. Paul Sanwald

    Things I really love in flatiron:- Breakfast at city bakery. Their pastries are fantastic.- Buying fresh pasta from Eataly, which is very reasonably priced and easy to make into a work night dinner.- Lunch at Eisenberg’s, the best old school sandwich counter in NYC.- Sitting (or taking a meeting) in Madison square park on a nice day.- Seeing music at the Jazz Standard, one of the best jazz rooms in NYC- Academy records, which has a wonderful vinyl selection and particularly great jazz and classical selection. Such a great store.I worked in flatiron until recently and am really going to miss it.

  23. Doug Calahan

    If you guys get a chance, check out “Where We Want to Live” by Ryan Gravel (2016). I bought it because I live in Atlanta and Ryan’s vision of the Atlanta “beltline” is now completely transforming Atlanta as a city (in an incredible way). But his thoughtfulness on how cities can be reborn after the car era is wonderful to read.

    1. Sahil Patel

      @dougcalahan:disqus fellow ATL-ien here. Checking out the book right now. Lived in ATL for several years, moved away for a long time, and then came back in 2011 – very pleasant surprise to see its progress. The belt line connections around Krog Street Market and O4W water park are among my favorites.

  24. Wissam Otaky

    Hi everyone! First post for me.. Parallels with Jane Jacobs article are very compelling. Had forgotten your reference to them as I read Jacob’s article this morning, and couldn’t help but think ‘this fits perfectly with Fred’s description of the Flatiron district’! Will be paying more attention the next time I’m in town. Can also now see the counter-effects of that theory at work in certain areas back home in Dubai.

  25. Matthew Zadrozny

    I wish I shared your optimism about Flatiron / Manhattan.Around the corner, you’ve got Eisenberg’s and on the east side of Union Square there’s a nice mom-and-pop wine shop. But these are the exceptions. Walk down Broadway or across 14th and it’s mostly large chains. When it comes to grocery stories, I’ll take my economies of scale, and I’m grateful Fairway is no longer the only game in town. But I hate the Chipotles and Starbucks and their ilk, and more than anything, I loathe the takeover of street corners by banks, which could just as well put their ATMs in stores.Idiosyncrasy is what makes a city a city, NYC in particular. I think there are many forces at work here, among them the return of suburbanites to cities. I wish I had a solution, other than to scold friends for patronizing the chains.Your own Yancey Strickler had a nice piece on this some months back:… “Fuck the monoculture”, indeed.And I wrote up my thoughts on the topic of gentrification the other week on HN / here:…Thanks for posting on this topic.

  26. jason wright

    Flatline Partners, or was that yesterday’s post?

  27. Anshumani Ruddra

    Would be interesting to see if these findings apply not just to cities (a type of community), but to other communities as well – especially online ones.

  28. Greg Cohn

    I think using 4sq data to generate quality of life scores based on Jane Jacobs-style principles is a really cool idea. Much richer than the “walk scores” the realty sites use. People could also tailor it to their own needs (e.g. outdoor activities, family-friendly things are more important to some than to others).

  29. fredwilson

    Never. Hehe