What books do you recomend for bootstrapping?

I’ve read @patio11 book Sell More Software so far and wanted to see what other books or learning resources you guys can recommend for things like conversion optimization and content strategy.


I just finished Start Small, Stay Small by Rob Walling, and Starting and Sustaining by Garrett Dimon. Got a ton of value out of both of them. They lean more toward the process of coming up with app ideas and building/running an app vs. conversion and content strategy, but you’ll find some good advice on that too.

Haven’t read Sell More Software yet, but it’s on my list!


I have read Lean Analytics and got ton of value about what metric to measure on each phase of our startups.

+1 for Start Small, Stay Small and Starting and Sustaining. I think both are my top recommendations for getting into the type of business I run. (Sell More Software is more interesting after you’re already selling a bit.)

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Thank you I’m going to have to pick up Starting and Sustaining.

I hadn’t heard of Starting and Sustaining before - I’ll have to check it out. Thanks!

  • Jack

It seems to me that in order to be a successful entrepreneur, you can’t just sprinkle entrepreneurly qualities onto yourself just as you are, at least that was the case with me, who started off so unfit for entrepreneurship. I think it’s more a matter of changing your shape to fit through an entrepreneur-shaped hole (others may have a different experience). So here are some of the business and business-related books I’ve read, some of which go down to a more fundamental level than a book that’s just about business, but which I think are entirely relevant due to the fact that life is one interconnected whole. Strong recommendations in bold.

Personal Development

  • How to Win Friends and Influence People by Dale Carnegie
  • The 7 Habits of Highly Effective People by Stephen R. Covey

Time Management

  • Getting Things Done by David Allen
  • First Things First by Stephen R. Covey, et al

General Business

  • The Lean Startup by Eric Ries
  • Micro-ISV by Bob Walsh
  • Built to Last by Jim Collins
  • Good to Great by Jim Collins
  • How to Swim with the Sharks Without Being Eaten Alive by Harvey Mackay
  • Founders at Work by Jessica Livingston


  • Your Money or Your Life by Vicki Robin and Joe Dominguez
  • Total Money Makeover by Dave Ramsey


  • The Little Red Book of Selling by Jeffrey Gitomer
  • The Ultimate Sales Machine by Chet Holmes
  • How to Sell Anything to Anybody by Joe Girard
  • Dig Your Well Before You’re Thirsty by Harvey Mackay
  • The Little Black Book of Connections by Jeffrey Gitomer


  • Online Marketing by Matt Bailey
  • The Art of SEO by (a bunch of people)
  • Guerrilla Marketing by Jay Conrad Levinson

And if I were to live life over again, I would start with these in this order:

  1. How to Win Friends and Influence People
  2. The 7 Habits
  3. Your Money or Your Life
  4. Micro-ISV
  5. The Lean Startup
  6. The Art of SEO
  7. The Little Red Book of Selling

I re-read 1 & 2 regularly because the lessons are so useful.


I highly recommend Start Small, Stay Small.

The problem with most business books is that they are awfully “fluffy”. You could describe the main concept in a few pages, so the rest of the book just pads that out, because it’s tough to sell a brief book. In my opinion, most of what Jim Collins writes, just to pick on a popular one, falls into this category. I also found Lean Startup to be a great introduction to the concept of lean startups for someone who has never heard of it, but otherwise not terribly useful if you already read something like Rob’s book.

I hadn’t heard o Starting and Sustaining. Too bad it’s not available on Amazon; that’s kind of annoying.

A really good point that I’ve heard from several people is: you’re going to learn more by doing stuff than reading another book unless it’s a really, really good one.

I agree Start Small, Stay Small has a lot of good information, but personally I found it a bit of a slog due to the writing style. If you have the time, listening to all the episodes of Startups for the Rest of Us is a more pleasant way to get the information.

I really liked Starting & Sustaining. Getting Real by 37signals is good too, and I didn’t notice it being mentioned.

I also liked Pricing with Confidence a lot, even though it’s not related to bootstrapping. But you need to price your product. And sell it… CopyHackers have great books for that.

I didn’t like Lean Analytics much, but I’ve been reading a lot of blogs about metrics and I’m critical about that topic, so there wasn’t much new there. But Ash Maurya’s Running Lean was ok, if you are interested in lean startups.


Excellent list! Here’s what I’d add:

  • The E-Myth Revisited - Worth it for the Entrepreneur - Technician - Manager model of thinking about business.
  • The Personal MBA - A technical guy summarises all the business books. Zero fluff, packed with value.
  • Million Dollar Consulting - Gets you in the mindset of delivering value to your clients. Useful even if you’re not going to be a consultant.
  • Never Eat Alone - A guide to networking.
  • Secrets of Power Negotiating - Think of this as your course in Defense Against the Dark Arts when sitting at any negotiating table. Useful for any sort of business that you’re doing.
  • Authority (Nathan Barry) - Wickedly useful guide to self-publishing and building a following.
  • (Sneakily added this later) Senecas Letters - Not really a business book, but the practice of vividly imagining your absolute worst case scenario was highly applicable when I made the jumps from full-time => freelance => business owner.
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The E-Myth one is good: it really fits into Dan and Ian’s talk, for those who were at MicroConf, about having an operating manual for your company. Peldi mentioned having a similar set of guidelines as well.

The idea, at heart, is to take everything you do and write it down so that someone else could do it. For many kinds of businesses, this allows you to hand things off to other people in the company, meaning that the business is something that runs on its own, rather than revolving all around you. “Work on the business, not for the business”. Amongst other things, this also makes the business something you could sell one day because it is valuable even without your involvement.

Seth Godin’s The Bootstrapper’s Bible (PDF: http://www.sethgodin.com/sg/docs/bootstrap.pdf). It’s not focused on software but it’s a great book and it’s free.

I’m listening to Rework by 37signals. It’s pretty amazing. I was a little dubious at first because it is a firehose of business thoughts. But the longer it’s gone on the more I’m enjoying it. I can tell this is something I’m going to be listening to many times.

What real, actionable advice did you take away from it? Anything you put into practice?

I haven’t read it, but looking at it, and having read their previous book, it makes my cynic-sense tingle: is it just a bunch of platitudes from the 37 signals guys?

Start Small, Stay Small was an excellent book. I bought it thanks to recommendations in this thread. It just changed my approach completely. I was writing code and not doing any market validation. I used Google Keyword search tool to find the potential market size, and found it was ridiculously small. Like 60 searches per month.

Anyways. I have to rethink a lot now.

I put mini book reviews at http://successfulsoftware.net/reading-list/ .

Personally I hated the e-myth book. An idea that could have been expressed in one paragraph spun out into a really tedious and patronising book.


Well, in truth there is not much new. If you listen to the different bootsrapped podcasts and have talked to entrepreneurs, and read other books, you’ll have gotten most of what’s in Rework.

However, what I’m getting out of it is that it’s a fantastic review of MANY different topics. From when to go full time, to when to hire, to start marketing before you start writing code, how much attention to pay to your competitors and customer, etc. etc. etc.

Again, not a lot new, but I find myself being happen for the little reminders along the way. You’d have to listen to hundreds of hours of podcasts to glean the same info, and you still should, but this is a quick reminder.

I searched for the table of contents and found this deal that should give you an idea of what all is in there and how brought (yet shallow) to topics are: http://www.mindmeister.com/49405294/rework-table-of-contents

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Andy, I would estimate that something like 80% of books in the “business book” category are a concept that could be described in something between 1 to 10 pages, with the rest being fluff.
The problem for authors is that no one will buy a 10 page book even if the concept is brilliant. The problem for those of us reading is that once in a while the fluffy book contains an interesting or novel concept. I know this well because one of my earlier, failed ideas, was a business book summary web site.

I would put the E-Myth book in that category of having one good idea with a bunch of padding. For many people running a small business, they get bogged down in “being” the business, rather than working “on” the business. It’s helpful to check that assumption and work towards a day when you could step back from the day to day running of the business by defining exactly who does what, how.

Perhaps that’s not possible for everyone, everywhere, but it’s a very important concept to keep in mind. The same thing is repeated in this book, which is even fluffier than the E-Myth book:


But fluff or not, I think to me that idea is part of the intrinsic appeal of the right kind of ‘micropreneur’ business: I don’t care if what I do is not a million dollar business as long as it mostly ticks along on its own once I’ve got it running. Most of us can earn pretty well by trading our time for money, but I think we’re here because we want to break out of that.

Your reading list is very good, by the way - most of the books there that I’ve read are ones that are not easy to summarize, because they contain a lot of real content!

Startups for the Rest of Us Episode 228 | 9 Must-Read Books for Founders

Of the ones I am reading/have read:

Traction - I’m still going through this, but am finding it a useful overview of methods of getting attention for a product with which I was not familiar.

A Guide to the Good Life - While this was interesting, it was incredibly dry and tough to get through, even as an audiobook. Perhaps find a summary online?

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