Long Roadmaps

I’ve been thinking a lot about entrepreneurs with long roadmaps recently. I blogged about this four years ago. And while I captured some of what is special and important about long roadmaps in that post, I don’t think it really does this issue justice.

So I’m back for more on this one.

A big vision is critical for a big success. You have to know where you want to be in a decade or more. That’s where the long roadmap comes in.

But the mistake most entrepreneurs make is the try to ship most or all of their vision in their first product. And that’s a terrible idea.

The best companies start with a very narrow product that nails something pretty simple but powerful. And then they go from there.

This is true in both enterprise and consumer applications.

A long roadmap is comprised of many short and focused roadmaps, each leading to the next one.

It’s like you want to drive from NYC to LA. You start by driving to Philly. Then you drive to Pittsburgh. Then Cincinnati, then St Louis, then Kansas City, then Denver, then Salt Lake City, then Las Vegas, and finally you drive to LA. Each trip is its own thing and you plan it out carefully and then execute it with focus and energy, not thinking about where you want to end up beyond the next city.

Another good analogy is a basketball season. You want to win the NBA championship. But you get there one game at a time.

I was emailing with an entrepreneur last night who has a long roadmap. And we were discussing this very thing. He said he was very patient. And I replied that building a great company is a combination of patience and impatience in equal doses applied unevenly. Impatient short term, patient long term.

A long roadmap helps you be both.


Comments (Archived):

  1. awaldstein

    Patience is not overrated.Needs to be on both sides of course, entrepreneur and investor. The sign of a true partnership. A rarity in my experience.

  2. LIAD

    a seed stage entrepreneur asked a wise venture capitalist how to get directly to his ultimate destination.the VC thought about it, rubbed his chin and said, ‘sorry, you can’t get there from here”

    1. James Ferguson @kWIQly

      A traveller asked a local – how to get where he hoped to go.The local suggested he’d better start from somewhere else.But there is a lesson – if you cant see your way forward, change your point of view

  3. maxciociola

    Inspiring as usual Fred. Thanks

  4. Dave W Baldwin

    Maintaining the balance is challenging.

  5. jason wright

    in the four years since your first post has Foursquare’s roadmap held its course?surely people have to adapt their initial vision to an unpredictable changing landscape, or they might drive off a cliff.

    1. fredwilson

      yes, very much so

      1. Chris Grayson

        Yes, very much so, it has held its course? … Or yes, very much so, it has adapted to a changing landscape?

  6. iamronen

    when does a roadmap become to long?

    1. jason wright

      when the money runs out

    2. Richard

      When you can’t see around the bend after the first leg of the journey

  7. Richard

    Favebook; Sometimes road construction forces you to take a new route anyway.Apple: Sometimes the roads ahead are not yet pavedGoogle: Sometimes you end up the toll taker and have all the $ you need to build new roads.Twitter: Sometimes you have an awesome product built for race tracks that’s does ‘t drive that well on main st.

  8. aminTorres

    Your best posts are the ones were it feels you are talking about the reader.

    1. fredwilson

      that’s great feedback. i want to try to do more of that

  9. JimHirshfield

    Yup, take the long way home.

  10. pointsnfigures

    This is a great point. You don’t get to look like a champion bodybuilder by lifting the heaviest weights first. To take your basketball example granular, before you can shoot 3’s like Stephan Curry, you have to learn how to shoot a layup. Then short jumpers with the right form (product market fit), then get stronger and scale back.

    1. falicon

      You need to do the drills before you get the skills 😉

    2. Sam

      The Steph Curry story is apt. Once he decided as a high school player on his long roadmap (NBA), he had to completely re-tool his shooting stroke to succeed against higher level competition. He had a great coach in his former NBA pro dad (by analogy a startup’s key adviser or VC) who showed him how to do it. And it sucked at first, but he put in the work. Then he took a small college program to the Elite 8. Then he got to the NBA. Then he shook off a few injuries. Then he won the title as MVP.

      1. JamesHRH

        There is usually one path – Curry @ Duke gets 50% less playing time & likely never gets the belief that he can dominate at higher levels.Carrying Davidson is the foundation for his NBA MVP.

  11. Screendoor

    Fred is right, of course, about the need for measurable short term milestones along the path toward the long term goal. But I think too many investors shoehorn the milestones into a standard model. “I want shipping product by month X, revenue by month Y, cash flow positive by month Z . . . etc.” And the entrepreneurs, not surprisingly, run like crazy to meet these milestones, regardless of whether what’s best for their company fits the model. The best investors understand this, and have runway built into their expectations when it’s appropriate.

  12. James Ferguson @kWIQly

    We think of stages and laddersEach stage has to get you somewhere significantEach ladder makes a stage possibleEach step in a ladder has to be simple.If everest didnt have different “base camps” – it would be much tougher !Also stages allow acclimatisation and hence stability

    1. Donna Brewington White

      Great points, James.Although I am finally “reading” (or rather listening to) Sheryl Sandberg’s “Lean In” and she suggests the ladder has been replaced by a jungle gym. 🙂

      1. James Ferguson @kWIQly

        Thanks Donna,I see the benefit of the opportunistic and chaotic analogy for “progress in the jungle”,However when it comes to vision you want clarity and range. You better climb to the very top of a tree where you are and then look out over the aerial canopy before you start defining your vision.Otherwise to risk a mixed metaphor – you won’t see wood for the trees 😉

  13. Tom Labus

    You may need different drivers and cars for each section too and a great mechanic.

    1. laurie kalmanson

      car, driver, crew, yes

  14. Brandon Burns

    The “product roadmap as cross-country road trip” analogy is one that’ll likely stick with me for a long time. Great way to think about things.

    1. fredwilson


  15. Jess Bachman

    A big vision should relate to the product, not just the number of users. When you look into the future a decade you should be able to see more than just your current product “but with many more millions of users.” Vision is much more than just extrapolating.

    1. Robin S

      Or in our case with a completely new base technology, we look to other vertical markets to license our tech through a custom built application for their market. That way we avoid having to come up with new products-just a new ways to use the same technology.

  16. Dale Patterson

    You’re right. We all want to win that championship right away but can’t forget “the grind of the regular season”.

  17. Matt A. Myers

    Most VCs don’t seem to understand this — if your roadmap is too big, too broad then it’s seen as too risky. Especially here in Canada.”Why you’ll fail at raising money” – https://medium.com/@sandima

  18. vijayvenkatesh

    Fred, This is a great point. How do you feel about situations, esp. in enterprise, where the breadth of scope may be a differentiator, or where the market may have competition that has niche/point solutions already.

  19. Kelly Taylor

    I heard Phil Libin talk about the book “The Clock of the Long Now”. I read it last week sitting on a beach for vacation and it definitely helped me think about our team’s product roadmap a bit differently. Thinking about things beyond a 1-2 yr time horizon is certainly a good exercise for the Prod Mgr.

  20. Salt Shaker

    Doesn’t “Long Roadmaps” refute or contradict the premise of blurring lines between public and private markets? The former, generally, is not accepting, or at the very least considerably less patient.

    1. Joah Spearman

      I don’t agree with that. Airbnb is a great example of a private company with a very long roadmap that has taken in funds from late-stage investors. It took some very long-minded investors at Sequoia to bet on Airbnb early when a lot of VCs passed and give them true venture funds rather than product-market fit funds as @paulrobertcary:disqus points out in his comment below. Over time, we’ve seen Airbnb’s long-term roadmap unveil itself from staying on couches to apartments to castles in Europe and now to building a full-fledged hospitality brand that is forcing companies like Expedia (HomeAway, $3.9bn) and Marriott (Starwood, $12.2bn) to acquire and defend themselves.

      1. Salt Shaker

        Airbnb is currently still a private company, but nonetheless I think they’re more the exception than the rule. Public markets tend to be less patient.

        1. Joah Spearman

          Amazon, Netflix, Salesforce, etc.

          1. Salt Shaker

            Groupon, Twitter, Pandora, etc.

    2. JamesHRH

      No, you need to see far and big but deliver near and small.If you execute into a big vision, you traditionally evolved from private to public. Fred is just saying that, eventually, there will be a middle tier where public pools of $$$ participate in leaning into winners (and that come with some downside).

      1. Salt Shaker

        Of course, one needs to articulate and execute against both a short and long term vision. However, private markets allow companies more time to execute their vision, in part cause they’re long-term investors and also due to a lack of liquidity. Public markets generally are less patient and provide less rope. There are more constituents to answer to and manage. AMZN is an easy exception to cite, as was TWTR until it wasn’t.

  21. vijayvenkatesh

    Not sure what you guys think – but after years of corporate/startup agile/lean/scrum, seeing that without a strong founder vision and roadmap, for your own startup, it’s so easy to get led astray, simply iterating away. I think this is something the lean startup movement misses.

  22. George Johnson

    “patience and impatience in equal doses applied unevenly” Love that.

  23. falicon

    The only problem is that you end up in L.A. I say we flip it and end up in N.Y. instead (a way better destination). 😀

    1. pointsnfigures

      sometimes you plan the trip for LA to NY or vice versa, and you wind up in Seattle.

      1. JimHirshfield

        Circa 1492…Sometimes you head for Asia and end up in the Americas

        1. Daksh

          “Get Lost”!

    2. ShanaC


    3. Donna Brewington White

      Watch it, buddy.Although I would love to be in NYC right now — just for a while.

      1. falicon

        To be fair I haven’t been to the L.A. area in over 15 years (and when I went I actually did enjoy it) 😉

        1. Merrick

          Yeah, it’s changed as much as Manhattan over 15 years starting in the 80s… Downtown is a safe and bustling downtown district, even with some Times Squareification over in the LA Live/Staples Center area. Bimbos have gone by the way of hipsters, so Williamsburg is the new Beverly Hills in terms of stigma. Give it anotger try sometime. It’ll be in the upper 80s today…

  24. Sam

    The microscope and the telescope. Great leaders need both.

    1. William Mougayar

      Great analogy.

    2. JamesHRH

      Just as some poor managers are ‘good from far, but far from good’ (i.e., the less we see of you the better)……most poor entrepreneurs are good at far, but far from good.A person in real estate development told me: “everyone can tell me what it will look like 18 months from now, but 18 months from now is always 18 months away.’

    3. Hugh Lang

      Also from Guy Kawasaki, The Art of the Start

  25. LE

    Interesting makes me think of the Traveling Salesman Problem:https://simple.wikipedia.or…The Travelling Salesman Problem describes a salesman who must travel between N cities. The order in which he does so is something he does not care about, as long as he visits each one during his trip, and finishes where he was at first. Each city is connected to other close by cities, or nodes, by airplanes, or by road or railway. Each of those links between the cities has one or more weights (or the cost) attached. The cost describes how “difficult” it is to traverse this edge on the graph, and may be given, for example, by the cost of an airplane ticket or train ticket, or perhaps by the length of the edge, or time required to complete the traversal. The salesman wants to keep both the travel costs, as well as the distance he travels as low as possible.This is one of those things that each of us probably still uses our brains for. When going out and about for a day, and when having 6 places we need to stop at, try to plan the best route, time etc. given various variables (even which day to do this on or hold off on something and create a batch of stops). I am sure there is probably an app that is doing this now but personally I find it perfectly acceptable to simply rough it out in my head (and quite satisfying as well for some reason).

  26. LE

    There are many people who start businesses with no long term plan at all. They get their feet wet and it grows to something that they could have never imagined might happen. And in fact if they had a roadmap that might have dissuaded them from even trying in the first place [1]. I am not doubting that it works as a filter for certain investors of course. Just that it doesn’t apply in many cases that I have seen over the years (my bias). [2] Part of the reason is what I call “the thing that leads to the thing”. It’s often near impossible at the start to know what a particular action or event will lead to. As such it’s simply a matter of working hard everyday, making smart decisions, and taking advantage of any opportunities and serendipity that you find. If you want a roadmap and certainty choose a well defined career (say medicine) where if you essentially hit the books it’s pretty much guaranteed where you will end up at.[1] The mountain at an early stage would have seemed to impossible to climb.[2] One example, Danny Meyer’s Shake Shack. Another the HP starting in a garage

    1. PhilipSugar

      I think that if you want to try to build a huge business with venture capital he is right. You have to have that grand plan and steps because without it you won’t raise money.But you are right you can also say I am going on a journey, I’m going to do this and then see what I see, but this means you will probably be a cash flow business.Here is an alternative plan: https://signalvnoise.com/po

      1. LE

        It’s interesting to me that that post (I scanned it I don’t have the stomach to read the entire post) comes from DHH.Almost as if [1] he feels that he is missing something and needs to apologize or justify the fact that he obviously is a well known entity in the tech world, apparently highly intelligent, but hasn’t done a unicorn himself and has to prove that he is happy and that you can be happy as well. The same thing coming from someone else I wouldn’t feel the same way I have to add. Kind of like the equivalent (if I can stretch this) of a woman with a house husband talking about how it’s not so bad and he is a good father. When we all know that she is jealous of the woman who are married to the heavy hitters. Why? Because they always have to apologize. Nobody ever speaks like that if they are at the top of the heap only if they feel in their mind that others need an explanation.His points of course I agree with. The problem is that we all know that in order to be taken seriously the trappings of wealth and success are quite important.[1] This is a guy who considers himself a race car driver and apparently quite the risk taker he is also somewhat of an abrasive asshole.

    2. ShanaC

      There is more to a roadmap than first meets the eye. This is why self authoring is becoming a powerful therapy technique. They may be on the roadmap but not the way they thoughy

  27. Tom Limongello

    In consumer, specifically social, it seems the problem with *not* shipping something full featured is that investors want to see a product that can survive in a world where there is no free traffic, or a world in which fb, twitter, instagram etc. are effectively monetizing rather than just a playground for startup experimentation.

  28. JamesHRH

    Just talking to a colleague who has a very successful tech based startup. When they started, they told everyone in the space ‘we are just going to focus on X’, where X was the biggest pain point in the market.Lots of other solution providers warned him ‘I don’t think you can survive on X.’They now have 90%+ of the market on a platform that is a lot more than X.

  29. Pete Griffiths

    When your head is in the clouds it’s hard to keep your feet on the ground.

  30. Pedro Torres Picón

    Love this: “A long roadmap is comprised of many short and focused roadmaps, each leading to the next one.”I think it’s true in building companies, but it’s also true generally in life. I’ve lately been building the “long roadmap” for my own life and it’s helped me tremendously in thinking about short term decisions I’m making professionally, personally, etc.

    1. Drew Meyers

      Yup.. most people play the short game in life. Winners play the long game.

  31. sigmaalgebra

    > Another good analogy is a basketball season. You want to win the NBA championship. But you get there one game at a time.But to have a record good enough even to be in the playoffs, have to start the season with a team already ready to win the championship.Yes, IIRC, “to start, don’t build something a million people like a little and, instead, build something 100 people love”. Okay, but usually only 100 users/customers a significant business won’t build.Sure, hopefully the 100 will tell their friends and the project will go viral. But just what goes viral and why is not an exact science. My little differential equation for viral growth, posted often enough at AVC,y'(t) = k y(t) (b – y(t))however good it is in some cases, still doesn’t say enough about how or why virality.A lot of startups fail; so, one obvious reaction is to come to market with something darned good, yes, even if only for 100 users/customers.Entrepreneurs can be very concerned about the old comment, “You only get one chance to make a good first impression.”

  32. Chimpwithcans

    Great stuff. Curious what led you to re-visit this topic – in particular did it involve measurement of readers metrics from the original post?

  33. JaredMermey

    You’ve written about Poker being a great analogy for business and poker came up again on your DFS post so perhaps this is good timing.I’ve always likened entrepreneurship and company building to tournament poker. There are a series of pseudo-independent decisions one has to make and none will have 100% likelihood to succeed. To have a big success, you both have to put yourself in good positions and have a little bit of luck that things beyond your control (I.e, hands hold up v market factors persist) in order to get the big payoff. Patience is key in tourney poker as the long term thinking component might determine if you take a bigger risk or not (as opposed to cash games which you are not as likely to think so long term about since you can just buy back in).And, in both situations you can do everything right and still lose.

  34. george

    The problem with long roadmaps, so many things change by the time you reach your planned destination. I think what’s central to roadmap thinking – there’s a pretty consistent design process that evolves; you start off with your vision – what’s intended, then new things emerge along the way and by the end, you often realize something much different then what was originally planned. Sometimes, the real magic occurs in that emergent stage, and so I agree, there’s often a bigger benefit to planning and executing in strategic parts or development stages.

  35. howardlindzon

    a good reminder for me today to pass along as well. thx fred

  36. Daniel Clough

    I think you have to be very flexible with your roadmap once it gets further into the future.I like to think about roadmaps as short, mid and long-term.Short term being fixed and mostly being actively worked on.Mid term reasonably well planned out, but some bits can shift about and be a bit fuzzy. Particularly towards the end of the mid-term.Long term is very much fuzzy and often thoughts, types of strategy or fuzzy, big projects.Timescales again depends on your product and business.When I was running a subscription MMO, we would have short term as next 0-4M, mid term at 5-12 months and long term as 12+ months.We’d try and think about it in those phases so it was obvious how much flexibility and planning was necessary for projects in each phase.Having long roadmaps enables you to think through how everything relates to each other too.

  37. Robin S

    Nearly 24 years it took to get the official traction that would cement our success. No VC would have (and after meeting with every VC in the Valley did not) funded us. Thank goodness too. Some things take time to wait for the window of opportunity to open. The key is to stay alive until that time.

    1. Donna Brewington White

      Wow, that’s patience! Good for you.

      1. Robin S

        Thank you, Donna. I keep waiting for my Guinness award for most persistent start-up.

  38. Lawrence Brass

    Does a long term roadmap for infrastructure and a short(er) term roadmap for products built upon that (evolving) infrastructure make sense?

  39. Robin S

    On the way, we tried different applications. One was a working model for the Home Depot whereas our 5 gallon water bottle Kiosk knew and reported when a full bottle was removed and the customer would just have it added to their bill from the kiosk. It also had a shrink protection built in. Our kiosk worked. But incumbent supplier, Nestle’s kiosk did not work so Nestle did what they can do and went to the Home depot head office and threw a hissy fit and HD canceled our project. Nestle never did get their kiosk working. #shithappens

  40. sachmo

    This is a great post, thank you.

  41. ksaurabh

    Absolutely. There is a popular saying – Journey of miles begins with a single step. You finish that journey – by just putting one foot in front of other – not forgetting for a moment where you are headed..

  42. hypermark

    My axiom on this I call the 1.0/3.0 Paradox. It goes like this. Every company is born of a 3.0 vision of what they look like when their products, channels and markets are mature.In this narrative, they become as dominant as Facebook, Google, Apple or Amazon, with all of the pricing, partnering and market leverage that goes with securing a gorilla position.Unfortunately, you can only release a 1.0 product, and the market typically places little value on your 3.0 vision, focusing instead narrowly on their 1.0 needs.Bringing these truths into full view, history suggests that 1.0 is usually “good enough” to get to 2.0, and by 2.0, you are legacy, which is 100X difficult to dislodgeHence, the game is won or lost by focusing on solving 1.0 problems that bridge you to your 3.0 vision.

  43. Donna Brewington White

    I don’t think we can hear too much about this. Thanks for revisiting.I remember that post. Has so much more meaning now. Has it really been 4 years? *sigh*

  44. kellercl

    This makes me think about Seth Godin’s blog post, “The secret of the web (hint: it’s a virtue).”http://sethgodin.typepad.co…

  45. Kirk Willard

    Thanks for your insight Fred. As early stage companies approach investors how might they sell the long road (LA) without minimizing the importance of the initial leg (Phili) or vice versa? The long road can sound audacious before you reach Phili.”We’re going to LA” to change the world. To get to LA though, we first have to get to Phili and this is what it takes to get there. Once we get to Phili, we will need more capital to get to Pittsburgh. We’re raising enough money today to get to Chicago. We’ll assess progress relative to targets at each milestone.”I appreciate getting to learn from your blog. Thanks.

  46. awaldstein

    Patience requires funding.And if indeed this is a cultural change in the entrepreneurial space it flies in the face of the freneticism and formulaic approach to how we pitch our ideas.The gap between funders that practice this and the rest is pretty wide in my opinion.

  47. Jess Bachman

    Great comment. I just spent five minutes picturing Columbus as a startup founder.”Ferdinand, I’ve acquired more users… but.. I’m afraid they just aren’t the right demographic. I’m going to pivot South, send funds.”

  48. falicon

    Patience requires customers (which is where the funding eventually comes from; either directly or indirectly).Start with a small, focused target of actual customers…and collect more at each pit stop…you’ll probably have to upgrade to an RV or a tour bus along the route…but you’ll arrive very happy and in style 🙂

  49. Robin S

    And bootstrapping is one way to get it.

  50. awaldstein

    yes and no.your statement sounds like a bootstrap which trust me i know that model.it costs capital usually beyond cashflow to grow even in chunks.love this discussion cause its not abstract, it’s brass tacks shop talk.

  51. falicon

    Actually I think it applies in both bootstrapping and funding models.I simply believe you need to be collecting customers at every phase.But I do concede that many times these customers alone are not enough to help you make it to the next pit stop on the journey (and that’s where outside funding comes in).Still I believe it’s that “collection of customers” that really enables/allows for outside funding conversations and opportunities to *actually* occur.

  52. awaldstein

    wise man!

  53. Drew Meyers

    Both funder and founder…that’s bootstrappingIt’s a long road that I’m on right now 🙂

  54. Robin S

    Took us 22+ years to the tipping point. Worth every beg, barrow and steal. Everyone is getting their loans back with interest! #toughlove

  55. Lawrence Brass

    “Hi Ferdinand, its me again, sorry for the tone of my last letter. I know you are a bit pissed off because we still don’t find the silk and species as I promised you in the business plan. I am absolutely certain that it is only a matter of time. The good news is that I offered stock options to the natives, so they are searching for the silk worms and species like mad! Could not have been better. As I told you, this new route to the Indies is awesome business, we should discuss new terms for the B round when I get back to Castile. XOs for Isabella, will keep you posted.Chris.”

  56. awaldstein

    A whole other topic. One that I I’ve been through more than once.

  57. Chris Grayson

    Thank you for sharing the link, @willykaram:disqus. I use Swarm, and was a user of the old FourSquare, pre-split. I’m familiar with their backstory. I was curious as to Fred’s take on things, from an investor’s perspective, and specific to this blog post.

  58. Robin S

    me only once. and that’s all I will ever need, thankfully