The Grind vs The Pivot

Everyone knows what a pivot is. You launch something, it fails to get product market fit, so you change direction and launch something different. There are many examples of successful pivots. Flickr, Twitter, Slack, and Kik all came out of pivots.

But there is another approach to finding product market fit and I call it the “Grind.” The Grind is when you launch something, it fails to get product market fit, and you grind on it, week after week, month after month, year after year, until it does. Usually the entrepreneur who chooses The Grind is obsessed with the problem they are trying to solve and can’t let it go. This tenacity is often rewarded if everyone is patient enough.

A good example of a USV portfolio company that has executed The Grind is Brewster.

Brewster is a service that aims to do for contacts what Dropbox has done for files – keep them in sync and make them easily available on every device you use.

Brewster launched in July 2012 and I wrote about it here. While Brewster’s mission has not changed one bit, the way they have attacked it has changed a lot.

In the initial version, Brewster was a mobile app that could coexist or replace your native contacts app. It connected with all of your social networks and attempted to keep your address book up to date and also provide intelligence about your contacts. It turned out that most people didn’t really need or want a new address book, but they did want their contacts kept up to date and sync’d to whatever device they were on.

So slowly but surely Brewster evolved. But there was never a pivot. The service has evolved into a one that, today, largely works behind the scenes in the cloud to make sure the contacts you have on your phone and your desktop and tablet are the same, that they are in sync, and when another Brewster user you are connected to changes their contact information, your contacts are automatically updated. This evolution required the company to solve some difficult technical problems.

Brewster works in the background to power your contacts, providing auto-fill when writing emails in Gmail and access to all contacts from the dialer, text messaging, and email. It’ll also make finding your friends on social messaging apps, including Kik, WhatsApp, Snapchat, a more fun and easy experience.

Over this thanksgiving weekend, The Gotham Gal joined me in trying out the iPhone again. She got an iPhone 6+ and I helped her move all of her apps and activity from her Nexus 5 to her iPhone 6+. Moving her contacts was trivial with Brewster. Here’s how I did it:

1. login at, add google via accounts and sync contacts sections (you need to both add google and then sync with it).

2. on iphone, add google account (settings app > mail, contacts, calendar > add account > google) and make to turn on contacts sync

3. that’s it. brewster will use the google connection with iphone to send updated contacts to the iphone

The Gotham Gal has >10,000 contacts. I have almost 30,000. For anyone with large contact databases, Brewster is a valuable tool. It will alert you to when you have missing email addresses, phone numbers, and faces for your contacts. I use those features a lot to continuously improve my address book.

The Grind is about continuously improving your product using market feedback and gradual but sustained product evolution. In order to execute The Grind, you need to keep your burn rate low. Brewster has been at it for almost four years now and has always kept its headcount and expense structure under control so it had runway to evolve and improve their product.

If you tried out Brewster when it initially launched and it didn’t do it for you, I’d suggest you give it another try. It’s changed a lot but still is trying to achieve the same goals. And the overall goal of a service that keeps your contacts up to date and sync’d on all of your devices is more valuable today than ever.


Comments (Archived):

  1. Barry Nolan

    This Steve Jobs quote on problem solving jumps to mind. I’ve been grinding for three years. I’m acutely aware that there’s a thin line between obsession and delusion.

    1. Twain Twain

      THIS — except inverted and I’m a grinder. I like to see things through, even when no one else can see it yet and everyone tells me to pivot. I know all about pivoting; I was Captain of Sports in school and in hockey, netball and basketball we learnt that pivoting keeps up the momentum and flow of the ball.When I was in NYC, I met Jim Hirshfield and shared that, at one point people told me to pivot into another Disqus (seriously). I declined and stayed true to my vision.I understand the complexity of the problem I obsess about. After all, only a “mad” person wants to solve signal:noise of Natural Language across not just the whole of the Web but also create a system that can transcend the tech sector into economics, linguistics, Neuroscience, consumer psychology, Quantum Information, philosophy, rating systems (Likert’s 5-stars) etc.That’s the stuff people think needs 10,000 developers, 10 thousand neuroscientists, 10 thousand Quantum Physicists, 10 thousand philosophers and 10 thousand economists and 10 thousand management consultants etc.But there was something I’d learnt as a child that was SO SIMPLE, elegant and universal that I knew it could be my key to unlock the big bad complex problem.That simple knowhow was the pH scale. When I was 16, instead of going into a tech company to make use of my A in Comp Sci — as most of SV’s technologists seem to have done…….I went into the research labs of GlaxoSmithkline and then, for a few years after that, into the labs of the world’s second largest aroma chemicals company to focus on tastes and perceptions. This whilst studying for my maths degree where I continued to code systems and models……Reflux this with experiences in startups, banking and corporate strategy………And 1 person — instead of 10,000 times N people — can create a scale and system for calibrating every single word, image, brand, experience etc. in the world that:(1.) Even a 2 year old who knows what a rainbow is can use.(2.) The greatest minds who’ve frame-worked our systems’ approaches to data intelligence and Natural Language couldn’t, haven’t and didn’t imagine of making.* Alfred Binet who invented the intelligence test* Rensis Likert who invented the 5-star rating scale* Charles Osgood who invented semantic differentials* Noam Chomsky-Marvin Minsky who invented AI syntax for Natural Language* the W3C team who created the ontologies schema for emotions* Peter Norvig-Ray Kurzweil-Geoff Hinton of Google* Stanford-MIT-Harvard-Carnegie Mellon’s NLP approaches and all their lexical libraries* McKinsey, WPP, SurveyMonkey, IBM Watson etc.Not even Apple, :*).All because my Dad died and it triggered me to “Do and make something meaningful in my life.”Hacking together a simple childhood tool with complex adult knowhow is worthwhile and great fun.Grinding is good for the soul. Our parents teach us to “work hard” and “practice makes perfect” for a reason.It keeps us humble and hungry in earning our progress no matter how small.

      1. Matt A. Myers

        What I have found is you need to acknowledge what you will want or expect out of the grind. If it’s purely for discovery and sharing that discovery with others or if you want or need to earn a living from it or to gain a larger amount of resources from it to move into more complex problems, etc.. This may dictate how deep into the grind you go or simply how quickly you come to certain conclusions, results or the solution/answer outlined.I personally know how and why I am driven and it helps me by understanding my own story. I would hope everyone has this same understanding of why their life is going in a certain path or if they haven’t yet, to choose a path or way of living/being in the world and working/practicing towards that.

        1. Twain Twain

          Exactly, Matt.There are millions of brilliant academics who grind for 50 years (a lifetime) because they want to prove some obscure theory from hundreds of years ago. Their motivations aren’t about money — unless they’re going all out to win the Nobel or similar prize, and they might be rewarded with that in the twilight of their years (when they’re in their 80s as happened with Peter Higgs and the Higgs Boson particle).Meanwhile, there are founders who grind for 5 months and give up because they see their friends hacking something over a weekend that gets investor / corporate buy-in. The 5-monther somehow feels like they’ve failed by comparison when that “something” in their idea won’t emerge unless they grind better and some more.Each of us is here for a purpose.And the sooner we discover what that purpose is and what we’re passionate about, the sooner we can learn from the grind and the pivots and whatever the startup process and life throws at us!

          1. Matt A. Myers

            Fully agree about purpose. I wish there was better learning or guides on how to navigate the struggle and what those challenges mean for the path you could overtake and be successful on; fear has been the biggest obstacle for myself moving forward, though with tools like yoga I’ve been able to so far manage everything that I have needed to.

          2. Twain Twain

            Steve Jobs was imperfect and fallible like all of us. Nevertheless, he shared this about fear in his 2005 Stanford commencement speech:“Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life.Almost everything–all external expectations, all pride, all fear of embarrassment or failure–these things just fall away in the face of death, leaving only what is truly important.Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.No one wants to die. Even people who want to go to heaven don’t want to die to get there. And yet, death is the destination we all share. No one has ever escaped it, and that is how it should be, because death is very likely the single best invention of life. It’s life’s change agent. It clears out the old to make way for the new.”_____________________________After my Dad died, I thought deeply about my own mortality and fears.And those fears vanished into nothingness.

  2. LIAD

    the grind is where the real magic separates the doers from the makes you forces you to be teaches you schools you in restraintit hones your products forges you into a leader.

    1. andyswan

      I believe it is Rush Limbaugh who says something to the effect that you should relish every wall you have to climb over…because it makes it that less likely your competitors will ever get where you’re going.He has some brilliant non-political insights after 20 years of creating, growing and dominating a niche.My other favorite is “I have heard there’s a recession on, I am just choosing not to participate in it.”

      1. JamesHRH

        I am with you in that it is easy to respect what he and say a Bill O’Reilly have built.However, net net, those two guys siphon money out of the American political discourse, a lot like the way Wall St siphons money out of the American economy…..with creating any real value.Creator of the first American NeoCon Echo Chamber is not what I would want on my tombstone.

  3. William Mougayar

    Brewster reminds me a bit of Plaxo if it evolved. Is there a longer term vision that’s beyond cloud Contacts Management?

    1. awaldstein

      Moving contacts is one thing, keeping them uptodate a different but interesting problem.Next gen CRM for recruiters are tackling this problem, resyncing contact updates from LinkedIn and others to keep the data fresh.

    2. John Revay

      Yup, Just read this post now…and thought of Plaxo as Fred wrote about syncing. I remember reading about and using Plaxo many years ago – say 5-6yrs+ ago…It looks like they are still around.

  4. awaldstein

    I’m a grinder by nature.Need to state that to make this work, it requires tremendous perspicacity on both the builder and the investor side.Patience can be painful and it requires capital.

    1. David Semeria

      …and time Arnold – as you have proved to our company once a week, every week, for the past 3 years.

      1. awaldstein

        Thank you David.

      2. karen_e

        What is Arnold doing for your company, David? Curious because New York to Italy, dispersed team, right?

        1. David Semeria

          Arnold is the only adviser to the company. My reasoning was a bit like for programmers: one great one is worth 10 average ones. He provides us with very valuable guidance on product, marketing and communication.The geographical distance is not really a problem (because Arnold always pops in to see us when he’s in Europe). The time difference is more of an issue: it’s hard to take someone seriously when they Skype in their PJs :)Arnold is a gem.

  5. pointsnfigures

    Grinding is tough on investors (and founders). Know of a startup. Same product since inception, same problem they are solving. But, they are serving it up differently. Starting to have success. Funny thing is, they were so far ahead of the market that the rest of the world is finally catching up and understanding the value they bring.

    1. awaldstein

      Be interesting to look at how much of the team gets swapped out when the new direction gets executed on.I bet a lot.

  6. reece

    I love that Steve has grinded it out… especially knowing what he’s gone through to get the product where it is. admirable to say the least

  7. andyswan

    There’s something real about the 3-4 year mark. I don’t know if it’s because the market catches up to the forward-looking entrepreneur or because the entrepreneur figures out what the hell hey are doing. Maybe it’s because that’s where they give up and have nothing to lose for one more brilliant push. Who knows.But I have seen it, and experienced it, so many times that I know it’s real.I’m looking forward to the first pitch deck that shows “grind it out for 3 years of pain” instead of “launch version 2″…

    1. awaldstein

      You and I are one on this one Andy.

    2. Drew Meyers

      *raises hand*… in year 3

      1. markentingh

        end of year 3, things are looking brighter than ever 🙂

    3. Nick Grossman

      i like that idea a lot, and have felt it tooit takes a lot of patience to get there

    4. Frank Denbow

      I’m with you on this. I’m a grinder that just hit year 3. The main thing I realize is my knowledge of the industry, the problems people face, and the available options are all very solid, and that just comes from having time to talk to people and interact with potential customers. Less focus on external validation and more hard feedback and iteration.

      1. andyswan


        1. fredwilson

          Copycat 😉

          1. markslater

            We are grinding in year 3. We would not be here today if we had not had the benefit of brutal learnings early on. Our mission is in tact – how we are solving it has radically evolved…..We kept out burn low, went through period of self questioning for sure. But we found the wedge, and are much better equipped through our grind to attack it full-frontal and win. Which we are doing……And there is no substitute for a patient investor. We have a guy called Rich Levandov. (avalon ventures) – his experience, guidance and patience continue to be tremendous, and all signs are that he’ll be richly rewarded – if its anything to do with us – we wont stop till he is 😉

          2. PhilipSugar

            Agree completely and if I remember right, going from direct to small business to other companies that serve small business.Some would call this a pivot, but I agree it is learned through The Grind.

          3. JamesHRH

            Homage, no?

          4. fredwilson


    5. PhilipSugar

      Great comment to a great post. I too have seen it and experienced it many times. I believe it has to do with both you and the market realizing you are real.By that I mean in the first year, you don’t know what you don’t know and many people in the marketplace will rightfully think: they’ll be out of business in a year.By the time year 3-4 comes about you have customers, you’ve been improving what you do, and the market has seen you many times. They say you have to see an ad 9 times to remember it. I think its the same thing.

      1. andyswan

        I like that explanation… never thought of it that way. “These guys are legit” seems to be a real phenomenon…. I know I think that way.

        1. PhilipSugar

          For many businesses it looks like this:Day 1: Excitement, exuberanceDay 365: What the hell did I get myself intoDay 730: I don’t think I can take this anymoreDay 1,095: I think we are going to make it.Think about that it takes 1,000 days of working on a problem to really get it.Now this is assuming you have a great team, picked a good problem, were able not to die (run out of money).Everybody loves fantasizing about the rocket ship, and for a very few it happens, but for most its The Grind.

          1. Elia Freedman

            The story of my life.

          2. Matt A. Myers

            You have to build the rocket ship first before it can take off; adding some clever thing about Elon Musk and SpaceX would be a nice additional to this short comment of mine..

          3. JamesHRH

            Rockets usually don’t go to the moon on the first launch.The GOOG / FB arcs are the real anomalies.

          4. Ana Milicevic

            If we optimistically assume an average of 10 hours of work p/d then that 1,000 days gets us to the 10,000 hour rule. Having lived through a few 3-year milestones, I think that concept readily extends to companies as well.

          5. PhilipSugar

            Very good point. This is the second time, you have had a better extension to my point, than I originally had.

    6. Aaron Klein

      I always thought Fred calling me a “grinder” was the nicest thing he’d ever said about me. 🙂

      1. andyswan

        My 2nd wife was known as Jamie the Grinder but it didn’t turn out to be a good thing. Still better than 3rd wife AKA the POLAR VORTEX

        1. JamesHRH

          See Andy, you shouldn’t reset when you are a grinder…….typed w love partner 😉

        2. JimHirshfield

          How many marital pivots have you had?

        3. sachmo


      2. andyswan

        I think they call it twerking now

        1. Emily Merkle

          literal LOL

        2. Aaron Klein


        3. Scott Kennedy


      3. Paul Sanwald

        in poker, players who just play their game hour after hour, day after day, and never alter, are called “grinders”. it can be both used as a derogatory term as well as a compliment.if there’s one thing I know about myself, is that I am a grinder through and through.

    7. Matt A. Myers

      I’m in the grind and every day feel more and more reward, and more and more gratitude for those who are helping me.I’m between year 3 and 4 from the original conception of I Live Yoga and will be profitable, without funding, in 4-6 months. A lot of this last push I owe to the support and love and passion that my co-founder / girlfriend has for me and I Live Yoga.I was drowning before though have found a way to breath again, albeit I still feel sometimes like I am drowning, though it is now very temporary and I resurface quickly.

    8. pointsnfigures

      An old trader once told me if you can survive three years in the trading pit, you can survive. He was right. Too bad that’s not the case for the screen.

    9. JamesHRH

      Pain is the common denominator in the 3 types of ‘tough outs’: the grind, the pivot & the reset.I find that grinders are grinders, pivoters are pivoters ( Stewart Butterfield has to be in the Pivoters HOF ) & resetters are resetters ( Steve Jobs comes to mind ).Self awareness is key – don’t grind if you are a reset person, etc.

    10. panterosa,

      Andy, if the 3-4 year mark defines The Grind – I now know the term for not only the determination, but the expertise (of self and market) which defines a Grinder. I was told to pivot earlier, and ignored. Glad I did.

    11. mikenolan99

      It takes three years to become an overnight success…

      1. thomasknoll


    12. Ian McHenry

      Love it! Going through the grind right now and starting to reap the benefits with Beyond Pricing. Amazing how quickly some companies burn through cash before product market fit. Keep it lean, grind it out, then pour the fuel on when it starts to take off.

  8. Lucky

    Love the article. Fred do you think you think you can do an article on local discovery anytime soon? I am really interested to get your thoughts on that.

  9. Markus Lehtiniitty

    I think what Flickr, Twitter and Slack & others have done should be called restart, not pivot. Their teams totally abandoned the old and came up with something new which did not have much to do with the previous products.

    1. fredwilson

      I assumed that is what a pivot is. Is it something else ?

      1. Markus Lehtiniitty

        The way I see it is pivot is a fundamental change of business, yes, but not changing the whole idea and vision. Pivot could e.g. be doubling down on some part of the business that is working or targeting different market & customers.I’d call Burbn -> Instagram and The Point -> Groupon pivots as they were built on learnings from the first products. By contrast, the Twitter idea was not inspired by Odeo but was something new as its own.

        1. rimalovski

          Agreed! just seeing this after I made a similar comment above.

      2. Nik Bonaddio

        For me, I think about pivots in the literal, basketball sense. A pivot is when you’re committed to some action – ie: a foot down, dribble up – and you’re trying to find the optimal option given your commitment. It’s an incremental, satisficing operation.This is fundamentally different than a “destroy and rebuild” option where the new idea is completely different and shares no common technology or genetics with the old one; to keep the analogy going, we’ll call this a substitution or a turnover.

      3. scott krause

        Eric Ries wrote a good piece a few years back detailing pivots. His premise was that you stick to the original vision, but pivot on either the customer segment, customer problem, or solution.http://www.startuplessonsle…It sounds like Brewser, according to Ries’ definition, performed a solution pivot?

      4. kenberger

        Android (Andy Rubin’s company, sold to Google) was a pivot from serving the camera OS market to the mobile OS market.Groupon was a pivot from The Point: take some core principle or technology and adapt towards a new product and/or was a complete re-start. Even with a similar team and investor list, this differs from a pivot.

      5. LE

        When you get to the place that you are in life, you are in a position to actually be one of the people that gets to define a word like that.It’s kind of like me with negotiation strategy, or domains which I have been around long enough and know enough about that what I say is something that would be repeated as important enough to be taken as defining (along with other definitions).Any single person’s definition can be called into question of course by another expert. For example you know whenever there is a movie they hire consultants for things in the movie that the writer or director is not an expert on. And inevitably some person says “hey that’s not the way nurses do their job” or “hey that’s not what the police do” which is all based on how they were trained or what they observed personally. The important thing is that they’ve been around long enough to form a credible opinion.Bottom line: What you think a pivot is, is what a pivot is.

  10. Ben Kinnard

    30,000 contacts is impressive – no wonder people say VC’s are professional matchmakers

    1. karen_e

      We are all professional matchmakers at a certain point in our careers, aren’t we? Isn’t that what people mean when they say that it’s all about the Rolodex?

  11. Chimpwithcans

    Great post this. I will try out Brewster once I update my Nokia-from-the-90’s! In the Samsung Galazy days, I found that Google Plus Messed up my contacts properly – was this the motivation for the app?

    1. jason wright

      I got the Moto E last week. So cheap, and ‘good enough’.It will get the Lollipop update too – cheap is smart. Is expensive still dumb?

  12. rimalovski

    Look forward to re-trying Brewster as I was one of those who gave up on it a few years ago.That said, the way you define a pivot is one of the core misunderstandings of the lean startup.A pivot is not just changing the product. I would argue changing the product is simply that…changing the product, which for many startups is a restart. Restarts are expensive and painful. Steve Blank defined a pivot as when you change any of the underlying assumptions in your business model. A pivot may mean you changed your target customer segment, your channel, revenue model/pricing, partners, customer acquisition methods, etc.While may seem like semantics, i think it contributes to a misunderstanding and miscommunication between folks and creates a false sense of acceptance of what it means to be lean. While I admire persistence and listening to the market, I’d rather see teams learn as many of those lessons as possible and pivot before they complete and launch their product, rather than restart or change the product after they’ve built and launched it…as it is much more expensive and painful to do so that way. That’s the whole point of lean—to minimize the time and cost associated with such learnings before you complete and launch your product. Though you will still need to grind it out after that.

  13. OurielOhayon

    Fred i am still failing in finding value in that. All my contacts are in Google. When i have a new device i add my google account and get all my contacts in sync everywhere. i am not sure what brewster does in addition to that?

    1. karen_e

      Good question. Looking forward to the answer.

    2. LE

      all my contacts are in googleSo if you don’t have contacts in for example linkedin or Facebook then it doesn’t appear to have any value.

  14. Steven Lowell

    Amazing timing of this post…I have a meeting today about this. I hate to pivot, as a grinder, but I dont see any other options. Is a tough pivot a form of grinding?

  15. JimHirshfield

    I’ll give Brewster another try. I gave it a shot 3 years ago on a spare iPhone I had (there was no Android version back then…and it was pre-cloud for Brewster). I like this new approach better because although I use Google Contacts (already in the cloud), I have both personal and professional G accounts. Sync’ing both to my phone is currently a hassle (dupes or just too large a file). De-duping is a big pain when it comes to contacts (for me).

    1. karen_e

      I haven’t opened my new iPhone 6 box since it arrived a week ago because I’m dreading the contact management part of the process. Dupes, multiple accounts, etc. I guess today’s the day for Brewster for me as well.

      1. JimHirshfield

        So I guess you’re not the kind of person to stand in line for hours for the latest gadget?

        1. karen_e

          I did get my first Mac in 1986 … fanboy since very long time. But somewhere along the way gadget/life management got complicated, right? It has something to do with Google vs Apple vs Facebook, you know?

  16. JimHirshfield

    +300 bits because…it’s Tuesday. Carry on.

  17. Ana Milicevic

    I really liked the relationship management aspects of old Brewster – I haven’t used it in a few years since I went full Android. It would remind you when you’d exhibit an out-of-pattern behavior, for example not speak with someone you typically speak with weekly for more than a few weeks.They’re presenting at this evening’s NYTM.

  18. Sarang Lakare

    The steps you mention are pretty strange & it is not clear where Brewster comes into the picture. In Step 2, you are asking the iPhone to sync contacts from Google – that’s it. Why are step 1 and 3 needed? (Disclaimer: We are building InTouchApp, a competitive product that is the mobile-first Dropbox for contacts – simply install InTouchApp on the two phones & sync happens automatically – no settings – no websites to visit!, and I must mention, we are also in the Grind zone! We have been quietly building this product and growing our user-base steadily who simply love our product (rated 4.6 stars across all app stores – Android, iOS, Blackberry)

  19. PhilipSugar

    Fred Brilliant post, and excellent way to put it. “The Grind” this is what many “lifestyle” businesses do. They grind away at a problem and eventually are successful. The Grind is what nobody likes talking about or writing about, but as you say it is real.

    1. pointsnfigures

      +1 on lifestyle businesses. sometimes people forget they are entrepreneurs too.

      1. PhilipSugar

        I have come to embrace the term “lifestyle” business. It doesn’t mean you don’t work, don’t use technology, etc.It just means you fund it, you build it, and you reap the rewards during your life.There are many great start-ups that aren’t VC funded and that is fine.

      2. LE

        +1 on lifestyle businesses. sometimes people forget they are entrepreneurs too.That actually comes across as a put down. The “sometimes people forget” part. Who are these people? I grew up with, and have been around people that own these types of businesses. Many would run circles around most of the people that fund those other types of businesses that are not “lifestyle” business. They have to have skills in a wide variety of areas and like I say need to “be 85% up to speed” on everything.The truth is the phrase “lifestyle business” has somehow been used in the same way that “well but she’s smart” is used with women or “he earns a good living” is used with men who aren’t attractive. Like it’s some kind of community college degree vs. the Ivy League.In other words that somehow the greater calling is the foolish attempt to win the lottery so that you get some kind of notoriety in popular media and popular culture. It’s actually something that appeals to losers who will never go anywhere and couldn’t even run a business like that. So all they do is focus on the people that exist in the mind of the media as some kind of role model. The media by the way is overwhelmingly staffed by people who haven’t done jack squat other than write about other people. They are writers. That is their job. Those that can do (if they are in a position to that is I recognize there are definitely reasons that some people can’t “do” that have nothing to do with drive and motivation).they are entrepreneursI was actually in the entrepreneurial program at Wharton. (A total waste of time in my mind at the time but it might have changed). When I graduated my girlfriend’s mother seemed very disappointed with “entrepreneurship” as a profession if you want to call it that. This love affair with the entrepreneurship (in it’s current form) is actually fairly recent. It’s like comparing what people think of Brooklyn today to what people thought of Brooklyn in the late 70’s.

        1. pointsnfigures

          not meant as a put down, compliment. Govt officials usually forget about them when they make policy-and chase software entrepreneurs.

          1. LE

            This is a classic case where a group of people who have no common voice (PR or otherwise, there is no effective mouthpiece for such a widespread group) somehow get disadvantaged to the people who either have a voice or are a more attractive visual or narrative which the media likes because it gives them something to talk about.In a sense this is happening now with Police, minorities, and what happened in Ferguson. There is no effective voice (or protests) for the other side (the Police and those who support Darren Wilson and what he did that day) so it appears that the problem is way larger than it really is with this whole “hands up” absolute total ridiculous bull shit (I want to be very clear on that point by the way).

          2. PhilipSugar

            There are tons of software entrepreneurs that run “lifestyle” businesses.I would love for there to be another term, but I haven’t come up with it yet.So I live with the term and embrace it.

          3. Matt Zagaja

            I’m just wondering in trying to figure out where the line sits, if we look back at say McDonald’s or Coca-Cola, were they lifestyle businesses or start-ups before they IPO’d?

          4. PhilipSugar

            That’s the irrelevant part. They were just a start-up that became a business.Anybody that has a definition for a start-up other than starting up a business is a flaming asshole.You start up a business. It becomes what it becomes. One way to start it is with OPM: Other People’s Money. Another is to start it is with YM: Your Money.As you grow you can finance it with OPM. or YM which comes from your company.Some people take pride in using OPM, and think that is somehow better. That is called a VC business in high tech. Ok. Maybe we should call the other a YM business, but people generally call it a “lifestyle” business, because when you turn YM into more money it really does benefit your lifestyle.It doesn’t matter if its high tech, low tech or whatever. That is a separate issue and is getting blurred more everyday.I see “high tech” start-ups selling glasses, razor blades, mattresses, make-up, and salads.I think there is more money made in purely technology companies from people that used YM to finance versus VC money.Now in general you don’t publicly celebrate so much when you use YM to make lots of money because…….it is YM, which is none of anybody else’s business.When it is OPM, you celebrate because that is how you raise more of OPM. If you don’t give OPM more money, eventually you will stop getting OPM.Just is what it is.

          5. Guest

            Thanks for the post Fred. Reminds me of Angela Duckworth’s work related to “grit” and how it trumps talent.Angela’s 6 minute TED Talk:…Nat Geo Article on Angela:http://news.nationalgeograp…When the going gets though I guess the successful people actually stay right where they are.

          6. awaldstein

            As do I .And it honestly comes into play when you are raising funds and discussing multiples.

          7. JamesHRH

            Just had coffee with a guy who has perfected this – his third one nearly runs itself.

    2. Matt A. Myers

      Or they’re just too busy experiencing it and don’t have time to write about it. 🙂

      1. PhilipSugar

        Very true. I read your above comments and agree.

    3. Emily Merkle

      no one likes talking about it because it’s like reliving PTSD

    4. LE

      They grind away at a problem and eventually are successful.The “grind” with “lifestyle” businesses (as mentioned I hate that term) is because they don’t have a fuck wad of money to paper over and solve problems.Every dollar counts if they even have a dollar. If they someone dumped millions on them that they didn’t have to pay back they wouldn’t have to grind in order to get to the same (potential) place.That’s not to say that giving them money would be the answer or that they aren’t screw ups that would fail.Perhaps even the time that it takes them to grind w/o money allows them to go at a slow enough speed to figure things out.Maybe you could argue that money might actually cause failure (by providing to much comfort).But under the rubric of using money to not have to obsess over some small details (“should I buy this desk or that desk”) and all the minutia that a business owner has to deal with (that chip away at their time which is what is in short supply) money goes a long long way to solving many problems in getting a business to work. Money also buys expertise in areas that you don’t have which allows you to operate at a higher level than you can when self funded or when your own personal net worth is on the line. Nothing is absolute of course. All things equal money is a major advantage.

      1. PhilipSugar

        Come up with a better term than “lifestyle” and I’ll take it otherwise I’ll be retro and say I like it.The only way you don’t have to back the money is if you completely fail. That really isn’t a great outcome and it will be painful.Otherwise you pay it back, and pay it back in spades.Having too much money can also mean you pursue wrong ideas. Go down wrong paths, not face reality of poor market fit. And if you don’t completely fail you are going to pay for wasting that money.I will agree that it makes it easier for certain things, if you have no money for marketing, etc, but for example sometimes it is really helpful to learn the expertise instead of buying it.

        1. LE

          Come up with a better term than “lifestyle”I think the term “business” is sufficient without putting lifestyle in front of it. “Restaurateur” or “race car driver” stand on their own generally. (And definitely not “small”in front btw).Having too much money can also mean you pursue wrong ideas. Go down wrong paths, not face reality of poor market fit. And if you don’t completely fail you are going to pay for wasting that money.That’s similar to not wanting to be “to good looking”. The idea is not to let it get to your head (or your parents forgetting to ground you) not to hope to have a less than beautiful child. An attractive women can always tone it down an ugly one can’t step up the game.Sure adversity plays into things. Sure being to comfortable is an issue. But all in all I’d rather have money than have to start with no money at all no question about that (been there).Besides (and I’m not discounting what you are saying) discipline is discipline. People have started businesses on a shoe string and then when they became successful they spent like drunk sailors.When starting out people who know nothing are going to make plenty of mistakes and go down plenty of the wrong paths. Having enough money to be able to make those mistakes is important. And to clean up the mess that is created as a result of those mistakes as well.

        2. LE

          By the way one of the things I love about the internet is that young people read comments like ours and think there is a right or wrong answer when it’s actually all nuance for a particular situation. That’s what business is. It’s an “all depends”. It’s not “these are the steps you follow to become a doctor”.My ex wife wanted me to send my daughter some money to help her pay off some of her school loans and I said “no way let her get some extra work and having the loans will give her motivation to ask her boss for a raise”. Otoh I did help her with some of her apartment payment costs so she could live where she lives. It all depends on the circumstances. No set answer.

          1. PhilipSugar

            I agree it is all nuances. Yes having no money sucks. Would I want to do things again with no money? No. But doing a huge raise and having a giant burn rate comes with its own problems. I have watched many a competitor blow through money and have nothing left to show for it.

          2. LE

            I have watched many a competitor blow through money and have nothing left to show for it.All of life is making smart decisions and choices at a particular point in time it all comes down to that. Giving thought to what you decide to do.I worked for a really short period of time for two companies in Silicon Valley (Rasterops and Supermac). Was a great learning experience. It was all about pushing shitty stuff into “the channel”. They sometimes (don’t remember which company) would ship in December and take back product in January “to make our numbers”.Both ended up failing (Steve Blank was VP Marketing at Supermac when I was there). They both were really idiotic in how they spent money. And what they did. The low hanging fruit ended (as a result of decisions made by Apple) so they no longer could survive. (One actually failed after the “new building curse” as well).As an example I had an expense account and had no restraint at all on what I could spend. [1] They didn’t even give me guild lines when I asked they said “buy what you need”. It was totally weird to me being from business where I came from where you watched every penny. Now I could go to the office supply store and buy whatever I wanted to. And I did. I could park next to Javits instead of blocks away. I could expense everything. I remember my boss signing my expense report not even looking at it. Right in front of me. Like a rubber stamp. I thought he was an idiot for doing that.[1] However one day I get a call from accounting because they noticed I had a $4 movie on my hotel bill. That they flagged! I thought “wow how fucked up this company is” they are completely missing all the other shit that they shouldn’t be paying for.

  20. Emily Merkle

    I bet grinding feels like being put through the grinder.

  21. ErikSchwartz

    Two years is now a grind?

    1. Richard

      An associates degree in grinding

    2. LE

      My saying is that “business is about taking advantage of the low hanging fruit of opportunity”.Under this scenario “the grind” could mean “failure” or it could mean rather than pivot try to adjust your positioning and product and get “the wind in your sails” (that’s for you, the sailor).An somewhat related example is the first business I tried to start. It wanted to sell computer supplies by cold calling offices. I went out for about a week but quickly figured out that it would take forever to get enough customers cold calling (this was 1981 btw) to make any money. [1] It would be pointless to grind on and I realized that. Not low hanging fruit of opportunity. So I thought “I need to do a mail order catalog that’s the way to do this”. Mass reach. But I didn’t have enough money to do that so I decided to get into printing (which I did) so I could print the mail order catalog. (Among other reasons. Never did the catalog though.). The day before the printing company opened people already were knocking on the door. I had picked the right location apparently. That’s low hanging fruit. [2] I sold that business a long long time ago but it’s still operating in the location that I started it in.[1] People were nice that wasn’t the problem the issue was the potential orders were small as well as the overhead of getting enough people interested (as a single salesman) to get to scale (if you want to call it that). I could have kept at it for longer but realized the approach wasn’t right.[2] A perfect example of this is Shake Shack in Madison Square Park in NYC. Taking advantage of low hanging fruit. An exercise in execution of a sugar delivery system.

    3. fredwilson

      I think I said four in my post

    4. Mark Shust

      I’m now hitting the 7th year of a grind. Sometimes it takes a while, but a good idea should be stuck with if you truly believe in it.

  22. Matt Zagaja

    Contacts is an awful problem but I don’t think Brewster addresses my pain points:1. I want my iCloud and Google Contacts to sync with each other. Currently I can pull both buckets into my Apple device and some will be in one bucket and some in the other and I can browse them and based on something they’ll link up if you have the same person in both buckets. People in my Google bucket can’t have relationships with other people for the purpose of Siri. Google contacts also won’t store my iPhone custom text tones, vibrations, and ring tones, at least as far as I can tell.2. I have lots of extra data in my contact cards from various sync programs and solutions I’ve tried. Some people have their addresses like four times. Would be nice to clean this up.3. Duplicates are awful.4. There are a subset of privacy minded curmudgeons who have decided to flout social norms by using incorrect names in their social media profiles. For each one I have to manually go in and correct and link the name in my iCloud contacts. It’d be nice if it could figure this out automagically.5. In addition to the privacy minded curmudgeons there are also people who think that there is not any utility to putting a headshot in their social media profiles and instead will post pictures of their dog, children, sunsets, or text advocating for a political cause of their choice. It’d be great if the contact sync program could perform the same kind of image recognition google uses and prefer headshots if it is either choosing from among multiple social media profiles or if a headshot is replaced with a non-headshot it’ll not update the contact.When people just used Facebook correctly and Facebook was more open with its data streams, that was the golden age of contact sync. It was a de facto phone book that everyone updated. The situation has been going downhill ever since.

    1. karen_e

      This is well stated. Pain, pain, pain!

  23. Guest

    HUGE FAN of Brewster, great post.

    1. LE

      Can you give some examples of how you use those 61,957 contacts?

      1. Emily Merkle

        booty calls.

  24. Noam Lovinsky

    Brewster has become a lot more like the parts of Plaxo that everyone really enjoyed, but without all the spammyness.

  25. Chris Phenner

    HUGE FAN of Brewster, bless them.

  26. LE

    Brewster is a service that aims to do for contacts what Dropbox has done for files – keep them in sync and make them easily available on every device you use.Average person doesn’t have a need for that.I guess the key difference here is that dropbox (which I don’t use (but see the value in) since I have my own office rolled solution to that) deals with objects (files) you think are important. Brewster on the other hands main benefit (from a quick read of the website) appears to be that it incorporates all your contacts particularly linkedin and facebook. The problem is linkedin and facebook are filled with people that don’t matter, [1] that you don’t need and that you don’t even know that you have or have forgotten if and how you know them. I would also add that the average person is not “rolodex” based like Fred (a vc) with a big and important network of contacts that constantly need to be tapped and brought up in order to keep the machine humming and most importantly “make connections”. [2] Most people can keep the important contacts they need handy the way they are currently handling that.[1] How often do I need to contact my brother in law’s brother? And if I do I know I can find him somehow on Facebook. Or just ask my brother in law. Ditto for linkedin. It’s filled with a bunch of people that in general have reached out for some reason that I have nothing to deal with and probably never will. And as that list grows over time it becomes more “out of sight out of mind”.[2] Fred and Joanne are connectors. Most people are definitely not connectors. I’m a connector I just referred my cleaning lady to a rental tenant. I am going to refer a lawyer that I don’t even use (that I dealt with by way of a customer) to another customer that I am dealing with because he appears to have expertise in a area that would be helpful. A connector (see Gladwell) is a person that puts people together and goes out of their way to do so.

  27. Joah Spearman

    Great post! There’s the grind of fundraising and then there’s The Grind of building a company, and I’d love to see you talk about the grind of fundraising for entrepreneurs next. Airbnb, Pandora, even Jeff Bezos have some great stories, but I’m sure you’re familiar with others, Fred.

  28. Guest

    Great post! Then there’s another interesting post is when does the Grinder actually have to give up? The one thing about pivoters is they just keep pivoting till they implode or launch. Grinders……well they just keep grinding and may need an intervention.

  29. jonathan hegranes

    I’ve been grinding to use Brewster almost as long as they’ve been grinding to make it work.I just hope they would have communicated better on how their service evolved so that the UX and trust that my contacts are syncing was never broken.For example, don’t keep a 10-month old app in the store if it’s buggy, if you’re never going to update it, and you don’t need the app anymore anyway.

  30. Michael Liu

    “If you tried out Brewster when it initially launched and it didn’t do it for you, I’d suggest you give it another try”I’m curious as to how difficult it is to get someone to try your product again once they have tried it before and didn’t enjoy the experience. I’m sure that’s one reason why people don’t “grind” it out more: the cost of re-educating your users and re-marketing your product.

  31. Jerome Zanet

    Fred, I am not trying something again that has failed in the first place. The future improvements (or the grind, as you call it) on a product does only make it look good in the short term. I am no game to these gimmicks of grind no matter how hard you urge us to try.-J

    1. fredwilson

      Oh, ye of little faith. Fig. You who trust no one.

      1. Jerome Zanet

        In thy business, no trust or sex is entertained, holy sir !!

  32. Ben Young

    Couldn’t agree more, I’ve found businesses tend to grow in waves of 9 months, every 9 months it takes a significant step up. And secondarily to that is that it takes about 4 years to get anything meaningfully going. People forget it just takes time, time to understand the problems, solve them, get feedback, get a case study, add new features, test them, marketing, build a reputation, build credibility, grow word of mouth, tweak your business model, hire the right people, build the culture, take breaks, adjust to the market, learn, optimize and then scale it. A fast growing organization isn’t excellence in one or two, it’s being excellent at many at once.

  33. Geoff Lewis

    Fred – I’ve always considered a “pivot” to be a change in strategy without a change in vision. Do you think Twitter was actually a pivot, or in reality a “failure” of odeo followed by a re-start behind the twitter direction w/different vision? I lean toward the latter, and think this is actually more impressive than a pivot because the team overcame the failure and restarted from near scratch. Curious re: your view / how you discern “pivot” from “failure, then restart”, or if the distinction even matters

  34. Chris Phenner

    I think Brewster could provide something really useful (that it does not today).You know how folks (often VCs) love to write about ‘the proper way to do introductions,’ which means ‘ask first’ before doing a drive-by cc line intro?Brewster should facilitate proper introductions of this sort.Because: An intro is ‘the atomic level of a relationship.’No cheesy, HTML-formatted emails. Just a shorter, faster way to facilitate intros where all parties no that the introducer is taking proper steps to ‘ask first,’ and when consent is confirmed, Brewster can facilitate proper contact information sharing.Kinda like where Hashable messed up (by focusing on ‘intro volume,’ not quality).

  35. jason wright

    Nelson Mandela breaking rocks on Robben Island was the grind.He did it for 18 years, and he was never wrong.Calibrate.

  36. perseusprime

    Fred,I almost worry that people will use your lead to justify investments that actually don’t solve a pain point. You can create a product but never a market. I hope you will qualify this article at a later time to write more about when to pursue a grind v. a pivot.

  37. James

    Thanks for the post Fred. Reminds me of Angela Duckworth’s work related to “grit” and how it trumps talent. When the going gets though I guess the successful people actually stay right where they are.

  38. Jordan Thaeler

    I also think it’s solution dependent. For instance, in some cases enterprise sales cycles are 18 months, so it takes that long to get real validation. Of course no VC will fund you to sit in that cycle, but that’s what it takes.

  39. Derek Andersen


  40. Cynthia Schames

    It’s been a while since I have had a moment away from the grind 😉 to really read the comments past a quick skim–but I am so glad that I did today. I loved this post, @fredwilson:disqus and I love so many of the comments here as well. Fantastic. We just passed year 2 of incorporation, and while I have actually believed all along that we pivoted last November, as it turns out, the deeper I think about it, I realize that we didn’t. As you said about Brewster, we’re solving the exact same problem we set out to solve, but we’re doing it in a totally different way than we’d anticipated.

  41. thomasknoll

    I guess we finally figured what the “????” in step 2 of, “Step 1. _________. Step 2. ?????? Step 3. PROFIT” stands for.

  42. Ronin_Jim

    Analogy: Attempting to climb a mountain. On your first try you hit a sheer cliff face. Do you give up and try another mountain or do you attempt the same mountain from another face?Great post.

  43. Ronin_Jim

    Question for Fred (and anyone at Brewster) – the HTC native contacts app does something like this, but not very well. The main problem is linking contacts is often manual and a lot of messy metadata accumulates.Any thoughts on Brewster vs HTC’s contacts app?

  44. stevanpopo

    It is often said that entrepreneurs need to convey a real sense of obsession about a problem in order to get funding and furthermore they are passionate about that specific problem. Given this, do you have a preference for entrepreneurs who choose The Grind? Or does it depend how big the pivot may be?

  45. Olivier

    Yes Yes and Yes.On a side note, the most incredible part of Brewsters grind is that they haven’t fallen into the trap of startups grinding by pivoting the data, most often personally identifiable data, that they have access to. I read their privacy word for word and it has to be one of the more reassuring ones that I’ve ever read (Confirmed even further by our own internal Risk and Reputation scores). A testament to their commitment to grind.

  46. FlavioGomes

    I tend to gravite towards entrepreneurs that grind vs pivot. Not to say that pivoting can’t have a successful outcome, butI’m not as supportive of vision swapping. It feels as if it doesn’t have the same level of conviction. The energy from from an entreprenuer that never surrenders his vision just gives me a greater sense of confidence in the eventual success.One another thought is that you seem to suggest that the grind ends when there is product market fit. Of course thats a huge phase of development and usually the hardest thing an entrepreneur can undertake, but feel as if the grind continues in a different context as you narrow focus on building the company.

  47. Liat Mordechay Hertanu

    Great and important post. Important to know/have while choosing the “Grind” way, is 1) to have enough cash (you said they kept low burn rate) 2) product’s competitive advantage while grinding.

  48. Isaac Palka

    Love that you covered this topic. We’re only a few months in with Zenly, and our offering and service haven’t changed, but execution has improved and become more nuanced as we continue to learn more about our customers and the space. It’s easy to fall into the trap of pivoting your core concept too soon, and many other real estate tech startups in particular have done this. Nice to see a post on this topic through an example!

  49. UberOnTime

    Determination and focus on your product or service will give you the will to grind. I can’t imagine a world where people give up on something because they want it now. If we all look back, companies like Microsoft and Apple had leaders who were grinders to the end. We all have to understand one thing; there is always we new generation that will adapt, if you keep the grind. This is my believe and opinion to how things should be done, when the passion and motivation keeps burning!

  50. paramendra


  51. disqusplaya

    I came here to read about Grind vs. Pivot. Instead I got a pitch for an office automation app. Less of a pivot and more of a bait and switch. Le Sigh.

  52. lfschwartz

    FYI – I installed Brewster after reading about it in your post. All was going well until today when Brewster starting sending emails to all my contacts (over 10,000!). No response from support via email or twitter (because they have no phone number). I deactivated my account and am now doing triage with thousand of people who Brewster contacted on my behalf when I never authorized them to. Not impressed and will never use or recommend again.

  53. p7r

    Fred, I specifically signed up to Brewster because of this post, and it looks a great service, but I just had to send this into [email protected] which I am going to post here as a warning to others considering doing the same – I realise it’s a portfolio company of yours, but I think we all need to be aware of just how wrong a direction they’re taking:—-I am trying to count to 10 on this one, but I am EXTREMELY angry with Brewster right now.I signed up the other week after the hat tip in Fred Wilson’s blog, and thought it sounded like a great service.Then, last night, you emailed everybody in my address book. I know this because:a) My girlfriend asked me why I did not have her current contact details despite us living together for nearly 5 yearsb) Several people on Facebook have contacted me, worried that it’s a phishing scam and EXTREMELY annoyed I have shared their private info with a company who is prepared to just openly spam like thatc) My work’s JIRA ticketing system has had multiple tickets opened by emails for you asking for up-to-date contact infoDo not try and say I suggested this – I would not ask you to improve contact information for JIRA email addresses, my girlfriend or several of the people who have contacted me overnight.You have made me look inept, careless and unable to use technology, which as a CTO of a tech start-up is not something I can carry very well professionally. You have publicly embarrassed me within my peer group, my family and my industry and that is utterly unforgivable.Please immediately remove all of my data associated with [redacted], [redacted] and [redacted] AND ALL INFORMATION RELATING TO MY CONTACTSDo not contact them again. Do not contact me again. Do not store information about me again.And finally, I hope that you either radically change your stance towards sending out information to people I don’t want contacting, or you very quickly curl up in a ball and die. If you were based in the EU I would be contacting the ICO and seeking fines of at least £50k to be levied against you, and I think they would be very happy to levy said fines. You can’t survive like this in the rest of the World.Goodbye,Paul

  54. Sean Besser

    Brewster has A LOT more grinding to do before it gets it right.After reading this I decided to give them a try. I deeply regret that decision at the moment as now my contacts database is a complete mess. I have thousands of duplicate entries now, often with 3-4 per person. And how can there be no info at all on their site as to how to fix or undo this. Seriously? What a colossal fail!Also, I believe all of this duplicate data is clogging up my iCloud account as well. I had plenty of available space in it before using your service and now it is totally full.Thanks Brewster for making a problem worse…seems like there are other reasons you have to grind.

    1. Steve Greenwood

      hi sean, this is steve from brewster. happy to help here. email me directly at steve @ brewster dot com.

  55. JimHirshfield

    He did NOT mean that kind of grind.