There is a big difference between being right about something and being right about when something will happen.

Sadly, to profit from being right you either have to get the timing right or you have to hang in there until the timing is right. The latter can be incredibly painful and most investors don’t have the stomach for it.

This is particularly true of short positions. It is not enough to know that something is going to blow up. You have to know how, why, and when.

On long positions, like venture capital investments, you do have the ability to buy time but it requires a lot of conviction and patience and the carrying costs can negatively impact the returns.

Which is why the best venture capital investments are always the right idea at the right time by the right team.

I remember watching streaming video over a 14.4 modem in 1997. Ten years later YouTube nailed that opportunity. Right place. Right time.

A lot of venture capital investors ask “what can go right” instead of “what can go wrong” and that is exactly the right mindset in VC investing. But you also have to ask “when will it happen and why?”

#VC & Technology

Comments (Archived):

  1. awaldstein

    Don’t we all know this one!My most painful experience in this category was not being to early and folding but having a controlling board thinking it was too early to sell and then the market shifted. Still stings a decade later.

    1. PhilipSugar

      Being too early and right is the same as being wrong.The flip side is selling too late is the same as being too early.As Rothchid said: I have made all my money because I have sold too early.

      1. awaldstein

        Good line that I will Certainly reuse.

      2. Twain Twain

        Unless you’re creating the category. You and @lawrencebrass:disqus told me to hang in there … Guess what happened …”As banks and wealth firms start using machine learning for better customer insights, they will need to ‘train’ their models on historical data. That legacy data is likely to be dominated by male investors, and any biases in that data set will not only be reflected in the new AI models but may even be exaggerated by the training process. This will lead to the wrong answers when women start representing 50% or more of new business.“The solution will be to run separate machine learning training on female-only data sets. This will be harder than just using all data from men and women, and it could be slower. But the algorithms that result are almost guaranteed to offer better insights about female customers.”http://www.cityam.com/27822…Client AUM of financial products is projected to grow to US$101.7 TRILLION by 2020. The LANGUAGE of products affects purchase.Yet 90% of women surveyed said that advertisers don’t understand them.We know that the data sets and AI from Google, Stanford University, IBM Watson, Microsoft et al are “inherently biased” and don’t understand language:* https://motherboard.vice.co…Eric Schmidt himself said: “It can be ‘very difficult’ for Google’s search algorithm to understand truth.”* https://www.cnbc.com/2017/1…The only system designed to be representative of people and language in a bias-free way is … mine. The patent was filed in 2013 and has passed prior art.@fredwilson:disqus — Yes, incredibly painful for inventor-founders.Still, on LinkedIn, some very senior technologists at D-Wave, Singularity University, Bank of England have commended me for calling out the innovation stagnation in tech and offering a different system.Is my timing and mission spot on and did I do the right things? In Dec, NYC passed first bill on bias and discrimination in algorithms:https://www.fastcodesign.co…Commercial opportunity, technological differentiation, founder mission and environmental changes all align.

        1. PhilipSugar

          Ahhhhh, I should have been clearer. As an individual or as a very lean company, being early is great, puts you ahead of the game.You can have the patience if you are not burning money, you can follow your dream, and that is great.But if you are burning through money, especially VC money, then you don’t have that luxury.

          1. Twain Twain

            As former investor for UBS and a VC (for a year), I know it’s a dance. VCs don’t necessarily see innovation until it’s too late. Or it simply doesn’t fit a thesis created 3-5 years ago or with a funding cycle or there’s no expertise in that area to mentor the founders.On the other side, some founders are good. Some aren’t.We meet the right matches and fits … in time, :*).

  2. Dan T

    I don’t know how you guys do it in consumer spaces. Most of the super successful winners were flooded with competitors – survival of the fittest – seems like so many were obvious spaces: video, search, friending, mapping, ride-sharing, buying/selling stuff, simple payments, etc., Twitter is one that just that seemed to me to be out of nowhere, creating new form/method of communication that only made sense on the web.

  3. Grace Schroeder

    Exceedingly painful for investors. Founders go sniper, cray cray, or both.

  4. Ian Hathaway

    Among that trinity of right idea, right time, right team, would you place any order of importance or are they all equally important? Or, is the answer: “it depends”?

  5. Tom Labus

    Being right and early is stll wrong on the long side. I’ve learnt, after many poundings, to reassess and get back in if warranted. Extremely difficult to do this from the short side.

    1. JamesHRH

      Classis venture maxim: early is wrong.

    2. Girish Mehta

      About investing -1. Play the game you came to play.2. Play the game you know to play.and most importantly -3. When there is No game, Don’t play.A mistake on timing can often be because of breaking rule #3.#3 is also an asymmetric advantage an individual investor has over a large/institutional investor.

      1. Tom Labus

        Sidelines is a position.Greenlight Capital dumped MSFT in 13 when they had a great position. Who knows why.

      2. PhilipSugar

        Another great comment and you are right about individual investor.

    3. pointsnfigures

      Yes. Anyone long Kodak? Ha

      1. Tom Labus

        Amazing desparation

  6. JamesHRH

    After being in this space for 20 years, it seems the right adoption questions are:- what can go right?- what needs to be in place to make things go right?- who controls the things you cannot control?That helps you figure out the when and why.And, distribution is always the best question to ask, as it is the #1 thing that most startups cannot control. With the exception of category creating product experiences, distribution kills more good startups than anything else.How good does your product have to be for distribution to be a no brainer? I still remember the feeling of:- first Google search I ever did – first iPad I ever touchedSurprisingly, I do not remember:- the first email I sent;- the first iPhone I touched (power not as evident until iPad, even though we had been all in on Apple product since 2004)- nor do I remember the page I landed on after the first Google searchI do remember phoning my wife and telling her the iPad would be huge (only 7 years ago, seems like forever).

    1. falicon

      +100, assuming when you say ‘distribution’ you actually mean “user acquisition”.* Email hits you when you “get” your first useful email (not when you send it)…and most likely we (you and I at least) were there so early and young that we didn’t even know how to identify that it was transformative…but we did stick around for one reason or another ;-)** It’s not a no brainer, but it would be awesome if you remembered that first time you used drip…you know…by subscribing to my campaign at http://d.rip/falicon (sorry couldn’t help myself) 😛

      1. JamesHRH

        I mean, getting them & keeping them satisfied ( not happy, that is death ).Same for suppliers or partners, if you have them.When you turn a product into a solution, you find that most of what you add is distribution: horizontal, customer or supply facing services.

      2. Donna Brewington White

        Haha! Love how you are promoting the Drip campaign. You could give up your day job and become a marketer!Correction: You’re a developer, so make that your *night* job. Or *day and night* job?Also, second that this is a great investment!

    2. Donna Brewington White

      I remember finding a candidate online the first time and also sending a resume by email rather than fax. Job boards were full of early tech adopters and for a brief moment as good as the candidates I could direct recruit. (That lasted a hot minute.) Mind blowing!#showingmyage

    3. cavepainting

      Agree. Also, if there is only one question to ask, it is: why should someone care? If there is a convincing answer to the why, dx/dt as growth % will be incredibly high (where x represents some proxy of usage).Time is the ultimate primitive and differential. Thus success of anything is a function of when it begins, how it grows, when it is liquidated, and how it deals with varying levels of dx/dt over its lifecycle. Getting each of these decisions right is hard and luck plays a non trivial role for all stakeholders. Also needs a prepared mind and a keen understanding of how the underlying “job to be done” can be better accomplished with new tech.

  7. Pranay Srinivasan

    Being right and seeing all the industry trends around “what” people talk about, “how” they behave / react to change, “who” the changes will affect, and “when” do the big guns in the industry actually come to the party are GREAT – But if you cannot build a team and execute, its almost like being too early as well.

  8. curtissumpter

    You should do another post about this. It’d be cool to see some examples of decisions around timing, just a couple, maybe one where you nailed it and one where … ehhh …. not so much. This is super important but it’d be cool to see some more color around this.

    1. Vasudev Ram

      Fred has mentioned in the past some of the examples where they (USV) did not nail it, e.g. Mercado Libre for one, and IIRC, AirBnB too. They’ve also nailed it a lot of times, of course.

      1. curtissumpter

        But I’m talking about specific to timing and framed in that frame. But there may be past posts about that and I’d be interested in that.

        1. Vasudev Ram

          Got it. I don’t have links to posts of his where he said that, unfortunately. If he had a search facility on his blog, you could have used it. And it would be generally useful to all of us here. For a while I think Fred had a plugin of a search facility created by @falicon (Kevin Marshall) who is a community member here.That point about search reminds me again of what I’ve thought before: search is such a useful and needed feature that it should preferably be available on any software app or even document-oriented app, like a blog or whatever. And good search at that. There are some mainstream apps or sites whose search is not good (enough), IMO.Paul Buccheit (Gmail creator and later at YCombinator) had said the same about apps needing an undo feature, in a blog post, and I agree. Undo is as important as search.

          1. Lawrence Brass

            The email bankrutpcy day I took a look to my gmail account and I found 30 drafts or so. Some were things that were never sent. I thought if it was a good idea to have that type of things stored in a server somewhere.

      2. Sebastián Aldasoro

        I know Flatiron did invest in Mercado Libre, which provided excellent returns through their IPO.

        1. Vasudev Ram

          Didn’t know, interesting.

      3. LE

        Airbnb is a good example of ‘“what can go right” instead of “what can go wrong”’. In retrospect of course.I would never think that airbnb would become as large as it has either. Because it defies many things about human nature that have existed in the past. The thing is those assumptions have changed. So the truth is it’s impossible to predict this type of thing.Here is the exchange that Fred has blogged about between Paul Graham and himself re: airbnb and the emails they exchanged:http://www.paulgraham.com/ahttp://avc.com/2011/03/airbnb/Note that in none of the emails (or in Fred’s relaying about what the team said about the idea) is there any mention of why this would work given the way millennials think vs. older people (as only one example) and how that has changed the potential. The root of the old timers objections (from what I can tell reading and knowing about this) is not countered by anything that either Paul Graham said or what the airbnb’s pitch to USV was. And to me that was the core of the success. Sure older people use Airbnb. But it is really younger people as the core base or at least it was until it took off. Seat of the pants it seemed that the younger team members understood what was going on but the older ones didn’t (and weren’t told). And nobody talked about this and why it mattered.A few weeks ago we started to discuss getting a car when my stepson turns 16 next year. I am actually excited about this because for me getting a car when I was 16 was the biggest thing in my life at the time. I couldn’t wait I loved to just turn a customers car around on the driveway when I had my car waxing ‘business’. My stepson? Literally doesn’t care and has little excitement. All his transportation needs are taken care of and he leads a low stress and great happy life that doesn’t make him want to get ‘away from the house if mommy can’t drive him’. He will just play some video game and entertain himself. A car is something he will like but he is not dying for it in any way. That’s a change in thinking that is hard for an older person (like me anyway) to wrap their heads around. When we were growing up we didn’t have addictive entertainment that he does. And the TV was defacto ‘turn it off’.I turned my much younger millenial brother in law on to airbnb when it came out. After he got married to a really beautiful woman he would travel (and leave her at home) while the spare bedroom was rented out to a complete stranger. He had no fear of what would happen to her alone with strangers.

        1. Vasudev Ram

          Interesting analysis about the difference in the ways younger vs. older people think.I had seen that email exchange between Fred and Paul earlier, I think via Paul’s site, in one of his essays, probably the same one you linked to. Also I think Fred mentioned the exchange too, maybe in one of the posts where he talked about his AirBnB miss, as I said above.

        2. Susan Rubinsky

          The younger generation input here, is key.(FYI, my 21 year old son doesn’t have his license and could care less about it and about owning a car. He takes Metro North most of the time with his bike or sometimes he Ubers from the train if the destination is in the suburban hinterlands. He prefers cities.)(Also, I turned my 75 year old Mom on to Airbnb last year when we took a road trip to Nashville. We got to stay in several cool places including a stone cottage on a horse farm in VA and a historic house filled with antiques in Nashville. All for a cost that was less than the ubiquitous cookie cutter roadside hotel.)

          1. LE

            My mom (about 90) grew up in the 1930’s. They rented out rooms in their house at the time. She said she remembers her mom coming in and kicking her out so a stranger could occupy the room. I think it was a rooming or boarding house down the shore.That was the style back then.https://youtu.be/-o-7MmhqNf

          2. PhilipSugar

            Let me say this…..let’s not extrapolate our situations to everyone. Here where you don’t have Uber……My daughter got her permit 90 days before she turned 16. My son who is 13 knows and can drive a pickup truck on non public roads.I would drive a 1955 International Harvester low boy 5 ton dump truck on roads and difficult one lane trails when I was 14.So yes if you take Metro North, (and I have from Grand Central many times) or NJT from Penn Station the world is different, but understand the world is different in opposite ways as well.

          3. JamesHRH

            Green Acres is the place to be!Saw a tweet today that said;I saw The Post, in a Movie Theatre, inside a Mall. It was like a consumer turducken of dying industries.If that have been in a town of 5,000 people?

          4. PhilipSugar

            Here is the thing, I am not disagreeing the world is changing. Not one bit, but the coastal elite look at it through a lens that is just theirs.I do not.Who is wearing a Nantucket Conference (top 100 tech CEO’s conference) t-shirt under his Cabbala’s Hunting Jacket today?Who cracked three ribs out working this weekend with other working guys?Who’s day can start off in the Dubai office take https://www.qatarairways.com/ home and on the less than hour drive:Stop quick at WhartonHave Lunch in the Chateau region of Delaware: http://beta.latimes.com/tra…Mentor some kids in Murder Town USA: http://www.newsweek.com/201…Have a quick meal at a restaurant where only Chinese is spoken in a suburban 25k student campushttp://www.udel.edu/about/Pickup some stuff in the fasting growing suburb sprawl in the U.S.: https://en.wikipedia.org/wi…And end up in the most beautiful town on the Chesapeake Bay:https://theculturetrip.com/…I am not humble bragging and I could go on and on.But I am constantly amazed that the perspective of many people is limited to their own bubble. Hollywood is the perfect example. Mark Wahlberg is the perfect outlier.I am not talking politics here.I am talking commerce. Yes, some kids won’t own cars, yes people shop less at malls, yes movie theaters will struggle (although not near me for StarWars), yes AirBNB will compete with hotels.Yes all of enterprises better realize that the world is changing and they need to adjust, use their strengths and kick ass, not become bloated and adjust.But when I hear tech people (and I put my skills up against anybody here) smugly say: So and so is dead: It is not only hubris it viewed by others as arrogance (which is worse).

          5. JamesHRH

            You probably missed my post on the Chaos Age & the book The 500 Year Delta.You theme is the same.People are adopting the success model of ultra successful people, without the underlying philosophy that some of those people hold.The model is:- think about your agenda constantly- do everything possible to minimize risk to your agenda- do everything possible to maximize your personal energyThis is a culture of narcissism.People don’t think it is wrong to close themselves off from irritation, complication, inconvenience or the unusual.They think the opposite.

          6. Vasudev Ram

            >I would drive a 1955 International Harvester low boy 5 ton dump truck on roads and difficult one lane trails when I was 14.Ha ha, cool. I used to drive both a petrol and diesel jeep (Willys or Mahindra jeep, converted from petrol to diesel [1] after a few months) and ride a Bullet (Royal Enfield 350cc four-stroke bike) at 16+. Also a Yezdi 250cc Classic two-stroke bike. Was working on a dairy farm at the time, and used all these vehicles for that work (except the Bullet, which was for fun).[1] The diesel engine fitted in it was not an automotive engine, but an agricultural pump engine (65 BHP or so) – a common practice at the time, to save on fuel costs, since diesel was a lot cheaper than petrol in India then. It was not really designed for use in vehicles. Used to make the jeep vibrate a lot. But the engine had solid torque. I noticed that while driving it on a flat road for a stretch, and then up a long steep road (this was in Bhopal, M.P., India); it would go up that long steep slope at the _same_ speed as on the flat part – _without_ my pressing the accelerator or changing gears. That made me look up auto tech stuff in books and I learned what torque was, as well as other interesting and useful stuff.I also read about double-declutching [2], a gear-changing technique, and tried it out a few times, including while going around turns in the road. Nearly overturned the jeep once while doing that, due to the surge of power the technique gives, while going around the turn, and the jeep being light and a bit top-heavy. Stopped doing it after that.[2] https://en.wikipedia.org/wi

          7. PhilipSugar

            Ha!! Great stories…..yes Diesels have huge torque. My boat: 210HP 900ft pounds of torque. Pulls like an Ox.And I don’t know if you used the double-decultching reference because that International had a a non syncromesh transmission.Don’t know if you ever have taken one apart, (I have many) the syncro’s are small brass gears that adjust the speed of the engine down or up to the next gear. If you don’t have those you have to do that and have a deft foot on the gas no different than when starting off, or you would do what we called “grind’m and find’m” and if you got caught doing that back in my day the teaching method for that was a sharp crack to the back of the head. Reflecting that is how I was taught many things.That International had a straight six gas engine, a four speed transmission, with a high/low transfer case, no power steering, no power brakes, a suspension that was hard as a rock, and a bench seat with no belts. In those days you better have had strong forearms and legs because driving was a physical task.

          8. Vasudev Ram

            >My boat: 210HP 900ft pounds of torque. Pulls like an Ox.Cool!>And I don’t know if you used the double-decultching reference because that International had a a non syncromesh transmission.No, just mentioned it. But I’d seen vehicles like the International (tractors, not harvesters) on that farm.>Don’t know if you ever have taken one apart, (I have many) the syncro’s are small brass gears that adjust the speed of the engine down or up to the next gear. If you don’t have those you have to do that and have a deft foot on the gas no different than when starting off, or you would do what we called “grind’m and find’m” and if you got caught doing that back in my day the teaching method for that was a sharp crack to the back of the head. Reflecting that is how I was taught many things.Ha, I had a bit of a problem too with using the clutch, when first learning to drive. Got it in a bit though.>That International had a straight six gas engine, a four speed transmission, with a high/low transfer case, no power steering, no power brakes, a suspension that was hard as a rock, and a bench seat with no belts. In those days you better have had strong forearms and legs because driving was a physical task.Heavy stuff.

          9. PhilipSugar

            Actually more like this because it was a work truck not a show truck. They call them “low boys” because the sides aren’t very high but you can then shovel stuff off of them instead of dumping.http://car-from-uk.com/ebay/carpho

          10. Vasudev Ram

            Solid truck. Looks like some Bedford trucks, which used to be seen and used in India too until some years ago (could still be around, not checked recently).https://en.wikipedia.org/wi…See the blue and red Bedford S pic in that article, also below.https://upload.wikimedia.or

          11. PhilipSugar

            Yes. Very heavy to drive. But very tough

          12. PhilipSugar

            I love that truck.

          13. Vasudev Ram

            Me too, looks great, and rugged.

          14. Vasudev Ram

            >Don’t know if you ever have taken one apart, (I have many) the syncro’s are small brass gears that adjust the speed of the engine down or up to the next gear.No, I haven’t. But I used to tinker around learning about auto parts (more of bikes than cars or jeeps), hang around at auto mechanics’ shops, and learned and used to do minor repairs on bikes, and also fix punctures (i I got a kit for that – tyre levers, adhesive, etc.). Was heavily into tools as a kid/teen, both using them (different kinds) and making some (simple wooden ones), and that carried over later into my software work, where tool-making is one of my favorite things to do 🙂

          15. JamesHRH

            I can top that!I helped my 94 yo Mom get a Nexus card!I love hearing stories of young minded older folks.

          16. Susan Rubinsky

            me too!!!

  9. LE

    Ten years later YouTube nailed that opportunity. Right place. Right time.Interesting to note that YouTube sold for roughly $1.65 billion in 2006 but it was an all stock deal.https://venturebeat.com/200…At the time goog was trading for roughly $200. Today it’s at over $1000. It was reported that Sequoia’s investment was worth $495 million at the time so I wonder how much of it they kept (another timing decision?). If they hadn’t sold it it would be worth 2.5 billion today.https://finance.yahoo.com/q

    1. falicon

      meh – what’s a few billion here or there 😉

      1. Vasudev Ram

        Got half a billion in change? I got a nice little seaside resort in Utah for you.https://en.wikipedia.org/wi

    2. Vasudev Ram

      BTW (everyone, not just @LE), YouTube uses Python a lot (and so does Google). For YouTube’s use of Python, see:highscalability.com: 7 Years Of YouTube Scalability Lessons In 30 Minutes:http://highscalability.com/…Excerpt:[The key takeaway away of the talk for me was doing a lot with really simple tools. While many teams are moving on to more complex ecosystems, YouTube really does keep it simple. They program primarily in Python, use MySQL as their database, they’ve stuck with Apache, and even new features for such a massive site start as a very simple Python program….The number of videos has gone up 9 orders of magnitude and the number of developers has only gone up two orders of magnitude….1 million lines of Python code…Python – most of the lines of code for YouTube are still in Python. Everytime you watch a YouTube video you are executing a bunch of Python code….A lot of YouTube systems start as one Python file and become large ecosystems after many many years. All their prototype were written in Python and survived for a surprising amount of time….The dynamic nature of Python is a win here. No matter how bad your API is you can stub or modify or decorate your way out of a lot of problems….Focus on algorithms. In Python the effort to implement a good algorithm is low. There’s the bisect module, for example, where you can take a list, do something meaningful, and serialize it to disk and read it back again. There’s a penalty versus C, but it’s very easy….Measurement. In Python measurement is like reading tea leaves. There’s a lot of things in Python that are counter intuitive, like the cost of grabage colleciton (sic). Most of chunks of their apps spend their time serializing. Profiling serialization is very depending on what you are putting in. Serializing ints is very different than serializing big blobs….More about knowing what not to do. How dynamic you make things correlates to how expensive it is to run your Python app.]and the video linked from the above article:Scalability at YouTube:https://www.youtube.com/wat…”This talk covers scalability at YouTube. It’s given by one of the original engineers at YouTube, Mike Solomon. It’s a rare glimpse into the heart of YouTube which is one of the largest websites in the world”Plug: I have a lot of Python experience, and I teach Python programming courses online via the Internet. Anyone interested in Python training can contact me via my blog or site:https://vasudevram.github.ihttps://jugad2.blogspot.in/…Email is my firstname (then) lastname (without dot or dash etc.) at Google’s email service.

  10. kidmercury

    14.4?!?!? Lol by the time that video loaded YouTube probably sold to google

    1. Girish Mehta

      He might be off on the speed or the year. 28.8 was quite common in 1997…pretty sure I was on 28.8 by ’96. At Internet World in Dec ’96 in New York I remember hearing about the future 56Kbps speeds.56K launched later in 1998 and was expected to be the “technical ceiling” for speeds on DSL.The two “breakthru” technology contenders at that time after 56K were – ISDN and something called ATM (Asynchronous transfer mode). And cable modems thereafter.ISDN was this breakthrough that was going to deliver a whopping 128K !

      1. Michael Elling

        I left Wall Street in 1998 where 5000 people were sharing a DS-3 (45 mbs) at my company. I signed up for RCN cable with 1.5mbs down and ~100kbs up and had faster access to information than my former colleagues on their shared connection limiting them to download speeds of 100kbs. It was really cable that provided the locomotive for broadband and few saw it coming then.By 2003, when I raised $6m for The FeedRoom in a series D, broadband penetration was just approaching 40%. No one believed in a “short video clip” future back then. But 40% is the magic tipping point for most emergent technologies and the real winners and losers begin to become apparent.In The FeedRoom case everyone we talked to (70 institutions) said there was no future in a “free” ad-based model. So we raised the money based on licensing and subscription model. Remember, 2003 was the bottom of the valley of the nuclear winter for internet/telecom.

    2. DeerSpotter

      they had better compression formats then, the only reason they stopped with those formats is because: A) military standards not supposed to be public. B) some encryption used was not secure.

    3. Richard

      talk about (bad) timing, Twitter is soo fuckedhttps://www.projectveritas….

      1. kidmercury

        Well major social media outlets, especially twitter, have been caught censoring already, and removing the blue check mark of people in a seemingly haphazard way at best (though seems to be targeting kooks and conservatives). Not enough people care yet, but I think that may change in time, especially as blockchain technology will allow for new governance models of social networks.

  11. DJL

    How does an investor estimate timing? Doesn’t the market determine the “right time” for a technology? (and if you are not already there it is too late.)FB was the 15th social networkGoogle was (at least) the 10th search engineApple did not have the first “pad” device or streaming musicI am always amazed how some of these deals (who where clearly “me too” at the time) got funding. It seems to only happen after massive consumer traction.

    1. Susan Rubinsky

      The earlier companies primed the market so that when FB & Google landed they took off. (They also solved a lot of clunky problems that led to faster adoption).Apple is different because many other products primed the market, such as: transistor radio, Sony Walkman, Napster, etc. Apple united disparate solutions at the right time. Steve Jobs was visionary and saw this coming decades before anyone else and he made it happen by sheer force of will. Apple is (was) an outlier, though.At the end of the day, hindsight doesn’t matter though, except if you’re trying to utilize it to inform better insights moving forward.

  12. Girish Mehta

    https://www.youtube.com/wat……A time to be born, a time to die.A time to plant, a time to reap…Note to self: also…a time to watch Forrest Gump again…

    1. Lawrence Brass

      I love that movie. Can’t tell how many times I have watched it. I recall using a banner with the white muddy sneakers and the feather for a few years. Meant a lot to me at the time, still does. Thanks for the reminder. https://uploads.disquscdn.c

  13. David Albrecht

    Did you mean to summarize Michael Burry’s plot in “The Big Short”? Or was it just an accident? 😉

    1. pointsnfigures

      people forget, the organization on the opposite side of that trade did the settlements. That makes your bile and stomach acid flow even faster

  14. Vitomir Jevremovic

    With crypto speculation now there are two rights: the right time to sell coins and the right time when (if) the project succeeds.

  15. Brian Schuster

    I’ve noticed a lot of the recently with my friends in the industry. We all know what we’re looking at (a bubble), but the problem is that because we don’t know the when and why, it doesn’t really help us.Even knowing the why is not enough. I just re-watched “The Big Short” and saw the scene where the mortgage market was collapsing (getting the what and why right), but the price of the bonds kept increasing (no when).Great thoughts, as usual.

    1. falicon

      It’s not a bubble until it pops.

  16. TeddyBeingTeddy

    How much success would you attribute to good luck, and how much failure would you attribute to bad luck across your investments? % estimate

  17. Gayatri Sarkar

    Psychologically how do you tame your mind in such aspects when you have to wait? It is very gruesome.

  18. Salt Shaker

    The same logic and mindset applies when choosing to work for a startup. Just substitute the word “investor” with “employee.” Both generally are a long term play to the pay window, along with right time/place intangibles. Both are saddled w/ opportunity costs, though an employee generally has more flexibility and can exit at will. The same due diligence and questions need to be asked wrt product, vision, team, management, brand differentiation, positioning. Sure, a company can always execute better, but if it’s a parity product then buyer beware. Can’t tell you how often I hear about a company’s “proprietary algorithm,” especially in ad or fintech. Hard to vet and a leap of faith.

  19. Charlie Muir

    I’m sure he wasn’t the first to say it, but Mark Suster once said that being early is just as bad as being late.

  20. JaredMermey

    This post reminds me of when you ask someone why they will succeed OR how they will defend themselves and they just say, “because we are first to market” without any nuance or caveats.Being first can be good or bad. The cost of learning what you are building and how to position it to the market is way higher, requires way more capital and results in more dilution. (Per Fred,” you do have the ability to buy time but it requires a lot of conviction and patience and the carrying costs can negatively impact the returns.”)Often it is the person who learns from someone else who was first to market but is still before the landslide of competitors who succeeds as s/he learns from all the friction points the first person had.

  21. pointsnfigures

    Digital books in 1995 anyone? Or sometimes you have the timing right, the space right and you bet on the wrong jockey/horse.

  22. jason wright

    late getting here today. what did I miss?

    1. Lawrence Brass


      1. jason wright

        the Greeks, they knew so much and that we seem to have forgotten. we seem to spend so much of our time ‘discovering’ things already previously known.60% of Ether is Korean won. it’s very vulnerable to regulatory change from Seoul’s technocrats. This I already knew.

  23. Iampipeline

    Curious to know how investors to evaluate an idea is at the right time now?

  24. andrewparker

    This talk from Jawed Karim (third Youtube co-founder that left when Sequoia led the Srs A) is the best analysis I’ve ever seen of YT’s timing and the secondary technologies that emerged to make the YT opportunity possible. https://www.youtube.com/wat

    1. fredwilson


    2. Michael Elling

      In 2003 I was raising money for a short video clip platform, The FeedRoom, and no one was thinking about free ad-supported video. But payback came indirectly 3 years later. In 2004 I started helping Nextone, the #2 session border control (SBC) company behind Acme, to raise money. Acme went the enterprise and large carrier route and was initially more successful, but Nextone went the route of the small carriers looking to arb the big players. The lead investor I was pursuing, OneEquity, was dithering for over a year to put in money. In September 2006 when Youtube was acquired by Google, the CEO of Nextone told OneEquity that 50% of Youtube’s video transited through Nextone’s SBCs. Seeing Youtube’s $1.6bn valuation there was a $30m check in Nextone’s coffers in 30 days. Jawed should add the SBC (and global scale of CDNs) as an integral component to his list of enablers.

  25. Richard Carlow

    From the entrepreneur’s point of view it is better to play the game and seize the timing as opposed to trying to overtly influence or force that timing. That takes discipline and a whole lot of explaining/ selling to investors. It’s tough to make decisions for the long term, for the right reasons. But in the end, if you chase or force things, you die.One key and difficult decision is when to accept to institutional money, once you fuel up with that there is no waiting to light up the burn. And if you miss the window while burning through capital you can only wave goodbye. I wonder how many entrepreneurs go through the process only to turn down the money, not because they don’t need it, but because they know they are early.

  26. Thor Snilsberg

    We now start every engagement with a “pre mortem.” It gives everyone a chance to outline likely causes of failure. Timing of XYZ comes up every time.https://hbr.org/2007/09/per

  27. creative group

    CONTRIBUTORS:”Fair weather fans be damned”Smashing Knicks players!#NotknickswayThe Knicks appear on that same path of ruining a great opportunity to provide support to Kristaps Porziņģis.Anyone who really isn’t just a casual fan not pretending to be a knowledgeable sports supporter realizes besides the owner of the Cleveland Browns the New York Knicks have the worst owner in professional sports. The true silver spoon recipient. The coach, management and owner needs to go. Dolan can continue his pursuit of being a blues player. Wish him all the best on his way out after selling the Knicks.We say this with all seriousness.#FredwilsonsaveknicksFred Wilson has the wherewithal and can put a ownership group together that will allow Basketball people to restore the Knicks franchise. Dolan would sell to Fred.Captain Obvious!#UNEQUIVOCALLYUNAPOLOGETICALLYINDEPENDENT