Only Once - The Book

My friend and USV portfolio CEO Matt Blumberg has a popular blog called Only Once on which he posts about the challenges and joys of being a CEO (for the first time, thus the name).

Matt should be familiar to AVC regulars because I have written about him and his company Return Path many times and he has done several guest posts here as well.

For the past six months, Matt has been writing a book about the CEO job in a business that is scaling. I like the way he described the book in an email to me the other day:

The Lean Startup movement is great, but this book starts where most of those books end and takes you through the ‘so you have a product that works in-market – now what?’ questions

Matt has finished the book and now it is available for pre-order on Amazon (Kindle, Print). The book will ship on September 3rd. If you are looking for a how to guide on the CEO job of a rapidly scaling company, this book is probably for you.


Comments (Archived):

  1. JimHirshfield

    A book every startup founder can aspire to need.

    1. mattb2518

      Thanks, Jim. It was a labor of love – I’m excited to see it come out!

      1. JimHirshfield

        Must have been time consuming – taking you away from running the company and your personal life. How do you juggle?

        1. mattb2518

          Not sleeping helps. ☺Honestly if I had known how much time it was going to take, I’m not sure I would have done it. But this year I’d actually dropped two other “extracurriculars” so I did end up (barely) having enough time.

          1. fredwilson

            It almost seems like not knowing what you are getting into is the only way people can get into something. And probably explains why we see so many young entrepreneurs

          2. LE

            “not knowing what you are getting into”100% correct. (Interestingly this phenomenon doesn’t happen nearly as often with people getting married or into relationships a 2nd time.)”And probably explains why we see so many young entrepreneurs”Also if you have nothing you have nothing to loose. What would be the chance that you would take all that you have now and bet the ranch? Close to zero? Could you face your wife and your daughters?Once you have a wife, kids, family and obligations you have to be fairly certain you are right (or very risk tolerant) to take some of the risks you have to take even with a small type business. You have to carefully calculate the downside to every decision. Or you will end up like the donut factory guy I mentioned in yesterday’s post.

          3. fredwilson


          4. bryanweis

            Hey Fred, speaking of young entrepreneurs…I have been trying to get in touch with you for a while now regarding the University of Cincinnati’s Bearcat Launchpad program; a new student run business accelerator program for university students.I know you’re incredibly busy but it would be amazing to get an hour of face time with you on Skype to speak with our teams this upcoming school year.We’ve secured some other big name VC’s such as Brad Feld, Keith Rabois, Ben Ling, Mo Koyfman, and a bunch of others. We would love to have you join in on the fun. Let me know if this is something you might be interested in helping out with, it would be great to have you!Thanks,Bryan

          5. Donna Brewington White

            …and parents. The similarities are fascinating.

          6. ShanaC

            what were the things you dropped? Do you regret it?

      2. LE

        There is a cost to doing anything that takes time. I’m wondering how this might have conflicted with your day job so to speak? It the “traditional” business world you typically don’t have people writing books until they have a ton of time on their hands unless there is another agenda [1] (Sheryl Sandberg or someone trying to pump stock prices).[1] Agenda doesn’t mean “bad”. Fred’s might like helping and sharing but avc’s agenda is deal flow, vetting of ideas, and contacts to help with whatever he is doing.

      3. Richard

        This type of book is long overdue. Trying to piece together the story, forensically, via a stack of red herring magazines, wsj etc, is tough. I hope you can put the unedited version online for those who purchase. Editors may not like the weeds but newly minted CEOs will.

        1. mattb2518

          Editors didn’t do anything to it. It’s all me. I will note that it’s missing stuff. Every time I asked another CEO to read it, I got two new chapters out of the feedback. But at 48 chapters and about 375 pages, I called it. I’m eager for more feedback and can write more for v2.

          1. awaldstein

            48 chapters!How long did you work in this ?

          2. mattb2518

            About 6-7 months. Roughly 1/3 of the content I had already written on my blog, but the rest is original. Matt

          3. awaldstein

            Thanks MattWas curious about the blog content piece. Was approached recently to do something in the marketing are and was thinking about how much I had already produced on my blog.Congrats on this BTW. I’ve preordered.

          4. mattb2518

            Thanks for the Pre-order.When I started the project, I assumed I’d written about 80% of the content on my blog already. I was a little sad to discover it was only 20-25%.Matt

          5. Donna Brewington White

            I was thrilled to see how much you devoted to recruiting/hiring/building a team. If a CEO doesn’t get this right, they are toast. Once I saw the table of contents I thought September 5 can’t get here soon enough. I guess I’d get it sooner on Kindle but I want a tactile experience with this one.

          6. mattb2518

            I couldn’t agree more. Thanks so much for the early vote of confidence. Matt

    2. ShanaC

      the question is when do you know you need it?

      1. JimHirshfield

        If you don’t know, then you’re in trouble.

        1. Matt A. Myers

          Or you just haven’t thought through far enough ahead yet.

        2. ShanaC

          if you run an awkward stage company – do you need this book?

          1. JimHirshfield

            By “awkward stage company”, you, no doubt, mean a theatrical repertory company that makes audiences feel uncomfortable? ….yeah, that kind of company doesn’t need this book. 😉

      2. mattb2518

        The minute you actually have a company/business, not just a project/idea.

        1. Matt A. Myers

          I imagine by reading it it could / would help you realize when / if you’re there yet then, running a company.

        2. Donna Brewington White


        3. ShanaC

          ok, and when does that transition happen?

          1. mattb2518

            I’m not sure there’s a hard line, but if I had to pick one, it’s the minute you have your first real non-founder hire. Matt

  2. William Mougayar

    There’s nothing wrong with Lean to start up, but it won’t get you to Growing-up. Growing/Managing/Scaling are another ball game, especially after you start to nail the product/market fit.If you “lean” on Lean for too long, it can become a crutch that can cap your growth potential.Great that Matt will raise the awareness on what it takes to be a real Startup CEO. I’m totally on-board, and echoing his message, and even amplifying it further.

    1. awaldstein

      Managing for growth is what businesses do if they make it.I don’t really see this as a start-up topic but just the core of what we do.

      1. William Mougayar

        I would argue that you want to manage for success, not just growth.Does Growth lead to Success or does Success lead to Growth?

        1. awaldstein

          In abstract, of course your are correct. In reality though, this is a mostly a semantic argument albeit an interesting one.Businesses that predominantly capitalize their own growth don’t have the luxury of this distinction. This is only relevant in the world of big investments, big expected returns.

          1. William Mougayar

            Here’s where I’m leading. Take a fictional startup as an example. They have tremendous growth of users, product/fit and continued growth, but they haven’t yet been able to realize their business model and revenue potential.Is that success? Partial success? Acquisition target?

          2. awaldstein

            Understand.I’m just a simpleton.I think great companies and executives come to work every day and just build value.Nothing else really matters.But–I’ve already ordered Matt’s book and bookmarked your new site.

          3. Donna Brewington White

            “I’m just a simpleton.”You crack me up, Waldstein.

          4. awaldstein

            I’m working hard to avoid complexity that defocuses. It’s easy to abstract and obfuscate ideas.It’s fun to think about but it is not always tied to helpful decision making.Doing Office Hours a fair bit lately has really shown me how to take an hour and focus without going so broad that it evaporates and without going so narrow that it’s just a tactic,

          5. LE

            “It’s easy to abstract and obfuscate ideas.”It’s great to get to an age where you can call bullshit on what others are doing and know the game they are playing and why. When you know enough to be able to stand up with confidence and not fear being the fool at the table.That’s hard to do if you are in your twenties which is why young people have to be so careful. As you get older it gets much easier.One of the reasons of course people obfuscate is to keep people from questioning things because those people don’t want to feel stupid so they assume what someone else is saying must be right.

          6. awaldstein

            Great comment.Even though I blog a bit and advise a lot, I have a natural disdain for punditry and academics as they abstract to create language and are always steps removed.Learning how to be a good advisor and mentor has been a process for me. Especially as marketing happens in execution and you must be hands on acquainted with the tools available.What I find is that the smarter the client and the more inspired they are, the better the map between their inspiration and my experience. When ever you have to tell someone what to do, it invariably fails. Whenever you discover the way to channel their vision forward as a partnership, invariably the result is better.Taking notes is what you do in class. Mapping a plan is what you do together.

          7. LE

            Where do you hope to go with ? What’s the end game with that? (I’ve got my thoughts of course).

          8. William Mougayar

            I’m due to call you and talk about it. It could be 2 or 3 directions 🙂 but first baby steps have to be on solid ground before anything can happen!

          9. Donna Brewington White

            Well, if anything, the monetization prospects look good. Real good.

          10. Richard

            I toyed around with this. Havig back issues of red herring back to 1997, I found its easier to get info from ex CEO than current on these issues.

          11. William Mougayar

            Those were the day when Red Herring was really good. Do you remember Upside too?

          12. PhilipSugar

            Or lets take the opposite. They’ve figured out their business model and have cranked revenues. Growth is there but is “just” solid double digits but not triple.So what is that? I guess it depends on what you were looking for.

        2. LE

          “Does Growth lead to Success or does Success lead to Growth?”Each business situation is different I don’t thing this is a question that has an answer.Success is really just the end result of a sum of really good decisions made at each juncture given how you view the situation you are in based on what you know or can find out. Much goes into this whether you are willing to take advice or even have access to it etc. In the end you are the decider.

          1. William Mougayar

            I agree. But that question generates a good discussion, because the two states aren’t always mutually leading to one another.

    2. panterosa,

      Sounds like a book to add to the SUM shelf, for the reason you describe.Will there be any self analysis tools on SUM to help people read for what they might not know is coming up? A sort of questionnaire?

      1. William Mougayar

        It’s been there in the Amazon bookstore, under Essentials. Yes! http://startupmanagement.or…I’m a big fan of Matt’s book and his message, as well as all the books on Brad’s series. (mine will be coming-up after…shhh)I am experimenting with self-assessment tools. Have you seen the Test about Company Culture at the end of that post?http://startupmanagement.or

    3. LE

      “If you “lean” on Lean for too long, it can become a crutch that can cap your growth potential.”In the traditional small business world “lean” is called “cheap”.You find it in businesses that are unwilling to spend any money on anything and they are obsessed with shaving costs in any and all ways and keeping expenses down. They actually get a buzz from being cheap. Really. (They reverse the reward system as I say). I’m not talking about people who don’t have the money either. And instead of spending time on ways to make money they spend their time on ways to save money (of course a time and place for this goes w/o saying). Because it feels comfortable and natural to them and is constantly reinforcing.I’ve run into this so many times. No investment in anything that improves productivity and little investment in advertising in many cases. I built a whole business because I was willing to fork over big dollars for yellow page ads which competitors who had been around much longer and had a much better product weren’t willing to do. (And direct mail and outbound sales as well.)You have to spend money to make money there are no short cuts.Side story here about “small” and cheap. I went to a shoe repair place last week to get my laptop bag zipper replaced. It was a “Jack Georges” bag so it cost maybe $250 when new? The cobbler says to me “it doesn’t pay to fix to much trouble it would take a lot of work”. All along frowning and acting as if he doesn’t want the work. This was over the course of about 4 minutes let’s say. Finally I say “how much?”. He says (sheepishly) $45. At that point I had no confidence in him to actually fix it and he didn’t appear to want the work. Also he had made me feel so foolish for fixing that I just walked out. If he had said “sure I can fix that it will be $45” he would have had the sale. That in a nutshell is one of the reasons he is a 1 man shoe repair shop (the other reason is he’s an immigrant who didn’t learn english probably.) I can tell you though that almost certainly he’s cheap. He just couldn’t wrap his hands around the fact that someone might be willing and want to pay him $45 to repair a bag zipper. And I wasn’t interested in really having to think about this anymore but now I have to.

      1. Matt A. Myers

        Yeah — People confuse lean with not spending money all of the time.Some businesses simply take more money to get off of the ground, and doesn’t mean they’re more risky.In my mind ventures that require larger sums of capital early on are less risky (relative), because there’s less competition because of the heightened barrier to entry of needing more initial capital.

        1. LE

          Another thing with capital outlay is that the fact that you have to spend money, and commit resources, means that you have to give some thought to what you are doing before you do it.If you need warehouse space, office space, or retail space (to name just three things) it forces you to be committed to what you are doing. You can’t just go off “half cocked” and then see where things lead.The barrier to entry point you are making is good and very valid. It is relevant both in difficulty and in money.When ICANN was formed and people applied to compete as registrars (about 12 or 13 years ago) one barrier to entry was $100,000 that you had to post just to get in the game. (Has since been dropped but other fees remain obviously). Then came deposits at the registry level, application fees, servers, programming and all sorts of other things that were required to pass the various tests. Perhaps another 100k. I don’t remember the exact amounts but they were not trivial. That was actually good and kept many people out of the business. (You also couldn’t have a criminal record that kept one very qualified person out (they didn’t say that but it was pretty obvious that was the reason.)

          1. george

            That’s one way to look at it! Although, I’ve seen the lean methodology work favorably in some businesses – when it’s not focused on cost reduction but forcibly used to challenge conventional thinking.

          2. Matt A. Myers

            “The barrier to entry point you are making is good and very valid. It is relevant both in difficulty and in money.”Most recently comes to mind is Tesla Motors – which never would have existed without Elon Musk putting in his own large sum of money from his previous exits.Re: ICANN formation – $100k + $100k sounds extremely cheap to me. I guess you don’t know how popular the internet would be, so the risk would be higher, but still … I remember when I first had wanted to register a domain name for the MUD I was developing. It would have cost $130 annually at the time. 2000 domains sold and you’d make your money back. You are of course competing, so you have to know how to market or have a budget for it, etc..

      2. Donna Brewington White

        “In the traditional small business world ‘lean’ is called’cheap’.”Ha! You have a way of bringing things down to size.Where is YOUR book LE. It may be time.

        1. Matt A. Myers

          I think it would have to be a series of books..

          1. LE

            Thanks Matt – re: “series” in reply to Donna I said:”Probably better than a book from me is a book with all sorts of info from people like me. That someone else writes.”

        2. LE

          Well first thanks for that compliment!Probably better than a book from me is a book with all sorts of info from people like me. That someone else writes.There was a book in the 80s from Harvey Mackay called “Swim with the Sharks” which was a big hit. I remember thinking at the time that the things he was saying were more or less obvious but more importantly that there were all sorts of people like him that had similar experiences and good valuable information. Mackay turned this (from what I see now) into an entire career. So to answer your question I guess I’m not really interested in that type of fame or to have that type of career. (Notice how I assume that all this would work that it would sell, pretty ballsy huh..but I’m fairly certain I could find the appropriate hooks since I think so much about reverse engineering what others have done.)Here is some things I just turned up (haven’t read anything he has said literally since way back then but some of this looks interesting)……I stopped reading things like this a long long time ago. I decided that I would try to spend time doing rather than reading I think many people end up (like people who are perpetually in school) just learning and not doing. Nothing wrong with that but $$ are important (as you yourself have acknowledged).

    4. mattb2518

      Thanks, William. All these successful startups courtesy of Lean have to go somewhere!

      1. William Mougayar

        Yup, I’ve been saying “the air is more rarified” once you poke through the 25-employee barrier. Now what.

        1. mattb2518

          It keeps changing as you get bigger, too. Hurdles are 25, 100, 250 so far.

  3. Tom Labus

    Is he the only CEO Return Path has had?That’s some run!

    1. fredwilson


  4. Barry Nolan

    Pre-ordering on Amazon signals you forecast being post product/market fit come September. I better get the hurry on.

    1. mattb2518

      LOL. Thanks, Barry!

      1. Barry Nolan

        Ever think about adding customer messaging in app? Would love to talk with you. [email protected]

  5. Brandon Kessler

    Matt if you’re reading, the iBooks (iTunes library) version has it spelled “StartupCEO” — one word vs 2 words on Amazon, so a search for “Startup CEO” as two words on Apple doesn’t turn up. I found it by searching your name, and just pre-ordered. Link:…” target=”itunes_store”

    1. mattb2518

      Brandon – good catch. I sent to the publisher and asked him to fix ASAP.

  6. Aaron Klein

    Pre-ordered. Can’t wait to read it – a huge fan of Matt’s writing.

    1. mattb2518

      Thanks so much, Aaron!

  7. reece

    @e85b4feddedc2231d6c232bf7be8406c:disqus is super sharp. always love his postsauto pre-order

    1. mattb2518

      Thanks reece. Much appreciated.

      1. reece

        thank YOU for all the knowledge share!

  8. andyswan

    Ordering. It sounds really really good.Lean startup sounds so good in theory, but it runs directly counter to every successful operation I’ve been a leader of or a part of or invested in.Try going back to 2001 and telling Tom Sosnoff he needs to talk with retail traders to see if they want an option-spread trading platform before he starts thinkorswim. I dare ya, I doubledog dare ya.

    1. Nick Ambrose

      I think there are definitely different ways to do it, some of which depend vastly on the “phase” at which the company/product is at, and/or perception of the companyWhen Facebook just started out, people’s tolerance of bugs say may be more than when they are a multibillion $ public company — I know mine are since it’s still uniformly the worst-behaving app on my phone.For an example, at a previous company, we were essentially doing a form of “continuous/rapid” deployment far before its current popularity.At first customers loved it (and it build a great market). When you can take a (reasonably big) product and deliver new features within the week that your major customer asks for it (and this includes new FPGA images), then you get a lot of brownie($$) points.However, that soon turns into “We love that you can ship so fast but wow, you seem to have a lot of bugs in this ever-growing product … ever think of doing any testing??”Then eventually you start to build up that “legacy of features” that made it so easy to break into the market against your major competitors in the first place who couldn’t move anywhere near as fast, and you go public and its”Wow, you guys have tons of money and resources now … this is no longer a scrappy startup, we have a very low tolerance for bugs since your stuff is now critical to our operations …..”and then you suddenly discover it takes a month to get out a patch because you have 13 hardware platforms to test is across on 4 different kinds of embedded environments and no-one paid down the last 6 years of technical debt so every time you touch something there’s a good chance to break something ….Of course, there are ways to avoid and prevent some of those pitfalls, but I think if your product scope grows, then it can get pretty hard to maintain that lean behavior.

    2. Aaron Klein

      So true. You cannot poll test your way to a great product any more than you can to the White House.(Mitt figured that out last year.)

  9. Mac

    Thanks, Matt. As a ‘Startup’ founder, just wrapping up a long pre-formative stage, your blog has been an invaluable and inspiring guide. Great timing! Looking forward to it’s debut.

    1. mattb2518

      Sounds like perfect timing. Hope it does the job for you!

  10. Daniel Clough

    going to pre-order soon and can’t wait to read. Love Matt’s blog.

    1. mattb2518

      Thanks so much, Daniel! Hope all is well in the UK.

  11. Pete Griffiths

    Matt – can you post a table of contents? I can’t find any meaningful information on Amazon. Thanks.

      1. Guest

        Thanks Matt.

      2. Pete Griffiths

        Matt – I take my hat off to you. Part II is absolutely critical information that lean doesn’t even begin to address. It’s ironic that people talk about teams but say virtually nothing about how to create and manage one and what if means to create and manage a company culture consistent with one’s mission, rather than have a culture emerge willy nilly. This is critical stuff.My first company went from 3 people to 150 if 4 or 5 years with no capital and by far the most challenging aspect was organizational. You move from a handful to a boutique to a company in very short order and it is a non-trivial task to maintain message and quality.This material is invaluable.

  12. baba12

    Wonder how much of the Lean startup philosophy is really VC’s trying to squeeze out as much as they can for a bigger return. What is interesting is a lot of the heavy lifting for startups today had been done by others in the 1990’s. Most of the VC’s that got burned then are not really there anymore or managed to survive because the burns while being bad were not so deep as to kill the life out of the VC’s.Today the emphasis is on lean startups while beneficial to some folks overall is not benefitting society. There are fewer VC’s today that will invest in the heavy lifting needed to address the bigger/greater challenges.I am sure Mr.Wilson (Fred) has read Jaron Lanier’s new book “Who owns the future” and also may have read Eric Drexler’s book “Radical Abundance” startups can’t deliver the promise of Atomic Precision Manufacturing (APM).I am not sure how lean startups will be formed around such new manufacturing platforms.I am guessing that USV and Mr.Wilson (Fred) would not agree with the gist of what Jaron Lanier talks about in his book.Is the mantra of “Lean Startups” really beneficial to entrepreneurs trying to solve the big problems in technology and bio medical sciences.

    1. fredwilson

      You are guessing correctly

    2. Dave W Baldwin

      Thanks for heads up on Drexler’s “Radical Abundance”. On page 28 is this:”Scientists study physical things, then describe them; engineers describe physical things, then build them.”Regarding new manufacturing platform, it is a matter of those with $$ being enlightened and focus on the more commercial need. We are not going to get to that platform waiting for gov. money and so on… that has already been proved.

    3. Jeffrey Hartmann

      I actually think this assessment of VC’s in general is quite flawed. My personal opinion is that the future is built incrementally and we stand on the shoulders of giants. What I am doing would not be possible without the blood, sweat, and tears of those before me. VC’s provide the opportunity to push the whole game forward. Maybe every single company taken by itself is not world changing, when taken as a body of work and the process learned from building so many companies by the community, they have transformed our lives.I for one also firmly believe that you don’t really want to face a ‘demon’ of a problem head on, especially at first. Much better to sneak up on it and surprise it. Many startups have huge visions on what they want to accomplish, but they need to build sustainable businesses that give them the resources to make the big changes and do the hard development. Look at what Google is doing now in the realm of driverless cars, totally wouldn’t get funding if they tried that first. Now they can do it as a ‘hobby’. Don’t be so quick to discount how much the world has changed from those startups addressing ‘lesser’ challenges.Atomic Precision Manufacturing might very well end up coming out of companies like the newly acquired Makerbot and companies like Shapeways eventually. It is definitely way too early to tell on that one. Being a lean startup doesn’t mean you can’t take big bets on a game changing technology. It just means you have to really balance that along with the other things you have to do, and you have to have a very good idea of market and potential if you are going to invest large quantities of scarce resources into some bit of research or development.

      1. baba12

        Well said but I doubt today’s VC’s have the capacity to invest in an Amazon that took nine years in all six after the IPO to turn a profit. Today I am doubtful a VC would be willing to wait that long to get a return that they are happy with, granted the costs that Amazon incurred back in the 90’s are not what they would be today.Many VC’s and bond managers were scathing about the burn rate of Amazon but I am doubtful that in todays environment a Amazon and Bezos could survive and stay in the game.”Those who play safe, live to fight another day.Those who play safe never get to the battle” I wonder if the VC’s of today are playing it too safe?

  13. Donna Brewington White

    @mattblumberg:disqus Congratulations and thank you! I am thrilled to see this book arrive on the scene. .Much needed — and I am sure a labor of love! Emphasis on labor which is why the sacrifice is so appreciated. Not only will this be valuable to startup CEOs but also to those of us who empathize with, respect, admire, support and cheer them on. I believe reading this book will help me to be a better supporter in helping them build their teams.Although watching from the sidelines sometimes makes me antsy to get in the ring! This book will either feed the fire, or douse the flame with a blast of reality.

  14. Donna Brewington White

    You need a new tag. :”Fred Wilson presents…”

  15. george

    Great focal topic – knowing when and how to scale. It’s the turning point to commercializing your product but also the critical point with shifting business dimensions; more outside-in behavioral thinking.

  16. William Mougayar

    Hey Matt, let’s email on this. I can share my early experimentations learning with assessment tools, and I’m due to review your book anyways 🙂

  17. mattb2518

    Sure. I’m offline a lot of today, but let’s get started – matt at myblumberg dot com