Ask HN: What books helped you in your entrepreneurship journey?

303 points by Gooblebrai ↗ HN
Leaving aside the fact that nothing can beat actual experience. What books helped you in your entrepreneurship journey?

114 comments

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Start Small, Stay Small by Rob Walling

Company of One by Paul Jarvis

Start Small, Stay Small is one of the least fluffy books I've ever read, with tons of practical advice. It's unfortunately a bit dated, but I heard he's working on a new one.
I assume you're not interested in hearing the obvious ones (zero to one, lean startup, etc., etc.) so I'll recommend two.

At the early stages when you're defining your strategy? "Good strategy/bad strategy" by Richard P. Rumelt. "Strategy" is thrown around a whole lot in business, often by somebody who is talking about a goal, as opposed to how to reach it. This book can get a little repetitive but the overarching teachings are valuable and will serve you well throughout your entrepreneurship journey.

After the startup phase (growth/acquisition)? I recommend "The messy middle" by Scott Belsky.

The messy middle was fantastic. Only reason I didn't list it in my comment below was that I read it recently and I'm 11 years in.

Highly recommend the book.

I read The Messy Middle and thought like the chapter titles were phenomenal, but felt everything in the actual chapters was fluff. Maybe I'll give it another try!
Steve Blank's blog (not a book, I know) + The Startup Owners Manual also by Steve Blank.

Lean Product Playbook by Dan Olsen.

The two helped me understand what it meant to 'get out of the building'.

7 Powers + Good Strategy Bad Strategy helped me think long term about the business model and evolution of the company.

‘The Millionaire Fastlane’ by MJ DeMarco. Laughable title aside, the content is life changing.
I joined their forums about 10 years ago and asked a question about a business idea. Basically I was asking about starting a gold/silver business directory thing based on some business described in the book. I was trying to understand some basics of what was being said. My post was not well received and MJ himself came in to tell me what an idiot I was.

I don't think I asked any more questions, and I left the PDF in the ash heap of my reading pile.

The Divine Comedy and The Prince. Not joking.
I was going to suggest Moby Dick…also not joking!
While I briefly ran a 'start up' with a friend (we weren't what most people here would consider a start up), we used the book 'Business Model Generation' almost weekly as we adjusted our business and pitched for new work.

I still go back to that when kicking off a new project.

Mr Nice by Howard Marks

Yes, he was a criminal, with great entrepreneur spirit.

- Awareness by Anthony DeMello

- The Courage to Be Disliked by Ichiro Kishimi

- The Virtue of Selfishness by Ayn Rand

- Only the Paranoid Survive by Andy Grove

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More stuff here: http://www.ryanglover.net/library/ (not flagged specific to entrepreneurship but all have had an influence in one way or another).

The Virtue of Selfishness by Ayn Rand

I love seeing this on your list. Firstly because it's a great book, and secondly just because Rand is so under-appreciated in general. Especially here on HN where her name seems to be all but verboten for some strange reason.

Thanks for echoing that one, I agree. I think a lot of the dismissal of her is due to second and third-hand knowledge of what she talks about (i.e., they hate the caricature of her, not her or her ideas).
Atlas shrugged, Minto Pyramid Principle, Nail it then Scale it
- The Mom Test

- 4 Steps to the Epiphany

- The Personal MBA (Josh Kaufman)

- Lean Analytics

- Good Strategy Bad Strategy

I've read a tall stack of business books, and in all honesty, I think only one of them was of any real value to me. It also has the benefits of being short and an easy read.

"The Incredible Secret Money Machine II" by Don Lancaster

“The Mom Test” by Rob Fitzpatrick - How to talk to customers & learn if your business is a good idea when everyone is lying to you.

https://a.co/d/8KzUk8b

It ended up saving us a lot of time.

I can't recommend this book enough. Even if you have a lot of experience with early stage customer development, you'll learn things from The Mom Test
I absolutely recommend it.
I also think this is a must-read for would-be entrepreneurs. Probably nine times out of ten when someone tells me about their startup idea looking for advice I point them to this book first because they haven't done the basic validation yet and want to jump right into building something that no one actually wants.
Traction by Weinberg. Understanding the distribution of your product, how to think about it and how much resources to devote to it was a missing piece for me as a technical founder. I easily fall into the fallacy of "build it and they will come" even when I don't think I do.
Traction, by Weinberg.

It goes over the various sales channels. How you get customers should really be the #1 priority for your startup.

Building stuff is easy. Getting customers is hard. And "if you build it they will come" doesn't really work most of the time IRL.

The E-Myth - creating systems and processes

The Personal MBA - crash course MBA

Founders At Work - understanding how different startups survived

Buy Back Your Time - management and delegation

The Charisma Myth - to help w/ charm for sales

SPIN Selling - this + The Charisma Myth more than doubled our sales conversion rate

These books were the most crucial for me

+1 for mentioning Neil Rackham's (1988) classic "Spin Selling".

Got it recommended from a friend after his exit (and after buying a French mansion from his share of the proceeds) when I asked him what he can recommend on understanding sales, in particular sales of (complex) technology. It's indeed a marvel for people new to selling.

I second E-Myth and Founders at Work. And let me add Crossing the Chasm, which totally shaped my understanding of who buys what when.
Wow completely forgot about crossing the chasm, good call
I came here to make sure Crossing the Chasm was on the list.
The Four Steps to the Epiphany - Steve Blank

The Discipline of Market Leaders - Fred Wiersema and Michael Treacy

It's Not the Big that Eat the Small...It's the Fast that Eat the Slow - Jason Jennings

Mastering The Complex Sale - Jeff Thull

How To Measure Anything - Douglas Hubbard

Looking back my too three are:

Hooked by Nir Eyal Viral Loop by Adam L. Penenberg Shoe Dog by Phil Knight

Rejection Proof: How I Beat Fear and Became Invincible Through 100 Days of Rejection by Jia Jiang

Highly enjoyable read! This book really captures the entrepreneurial experience of interviewing for insights while focusing on the fear of rejection, which is a major problem that isn't typically found in most other books on entrepreneurship.