A Startup Education in 50 Books and Podcasts

And How to Consume It All in a Year or Less


Inefficient. :)

About a year ago I started working on a startup in my spare time and needed to learn as much as I could about the process.

I’ve figured out that the consumption of audio content is critical for productive, efficient learning. I mean, at least for me, but I’m willing to bet that this is a pretty general principle. It’s just so efficient. The real value of audio for learning didn’t really become clear to me until I became a dad, which, incidentally, takes some time. There’s nothing like parenthood as a forcing function for productivity. I have to do my part to help keep our household running well, to spend quality time with my kids and take time to enjoy being a part of their lives. And, as Brad Feld writes in Startup Life, you need to pay attention to the needs of your important relationships, and dedicate time to them, or they will suffer, and so will you and your startup.

I regularly consume 1–3 hours of audio content per day, often more. I do this while involved with regular tasks like making breakfast, cleaning the house, working out at the gym, grocery shopping, traveling to and from the gym and grocery shopping, etc. Some days afford even more audio time, like weekend home projects that let me really get into an audio book for 8 or 12 hours. I’ll usually listen to a podcast for a while after settling into bed, too.

Since I’m often doing something else while listening, I sometimes have to tune out for a bit to focus but most of these things you can do while still giving attention to processing what you’re listening to. But, if the podcast or audio book is particularly important, I make sure to listen to it again. I’ve listened to some of my favorite audio books and podcasts three or more times through now.

Audio is a time generating super tool that can increase the available time you have for learning by an order of magnitude or more. Give it a try. It has allowed me to listen to thousands of hours of audiobooks and podcasts over the past 12 months.

Books about business, management and startups

  • The Hard Thing About Hard Things by Ben Horowitz — This is one of my faves, I’ve listened to it twice. Great stories from Ben’s time at Netscape, Loudcloud and Opsware, and patterns and lessons he’s learned starting Andreeson Horowitz. His style is different and interesting, I dig the intercalary rap quotes. One highlight for me that I keep going back to is his excellent chapter Good Product Manager, Bad Product Manager.
  • Do More Faster: Tech Stars Lessons to Accelerate Your Startup by David Cohen and Brad Feld — Tech Stars founders Brad Feld and David Cohen give a glimpse into their accelerator as they teach lessons they’ve learned over their careers to fledgling startups organized into seven themes: Idea and Vision, People, Execution, Product, Fundraising, Legal and Structure, and Work and Life Balance.
  • The Launch Pad: Inside Y Combinator, Silicon Valley’s Most Exclusive School for Startups by Randall Stross — Takes the reader on a fun ride through one YC batch from application process to demo day. Loaded with enlightening conversations between YC partners and companies.
  • The Founder’s Dilemmas by Noam Wasserman — A thorough examination at the many important decisions entrepreneurs face when starting a company.
  • Good to Great: Why Some Companies Make the Leap… and Others Don’t by Jim Collins — The Jim Collins books seem to make most booklists of successful business people, and for good reason. They are impeccably researched and he expertly distills the best practices based on his research.
  • Great by Choice by Jim Collins and Morten Hansen — The followup to Good to Great published ten years later gives more data-driven best practices for thriving in the uncertainty and incredibly fast pace of today’s business world.
  • Whats Mine is Yours by Roo Rogers and Rachel Botsman — I read this one because SpareChair is a part of the collaborative consumption movement. Online marketplaces and communities are making it easier for us to share our stuff and time.
  • Start Something that Matters by Blake Mycoskie — Think about real value to the world, that will result in a good business and something that matters.
  • Startup CEO: A Field Guide to Scaling up Your Business by Matt Blumberg — Most startups CEOs are first timers. Blumberg was at ReturnPath and here provides the often painful lessons learned so you can learn from his mistakes.
  • Venture Deals: Be Smarter That Your Lawyer and Venture Capitalist by Brad Feld and Jason Mendelson — Must read before you start the fundraising process. Feld and Mendelson provide critical knowledge about the legal aspects of incorporation, structure, equity, control and what to expect in a funding negotiation.
  • Crucial Conversations: Tools for Talking When Stakes are High by Kerry Patterson — Just about every conversation you have in the early days of your startup could be considered crucial given the outsized impact they will have on your success. I’m a believer in the ideas of this book to help you have conversations that are more productive and enriching.
  • Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur by Brad Feld and Amy Batchelor — A crucial read about the oft eye-rolled work-life balance. Here’s the thing: achieving a sustainable balance between your work and the rest of your life is critical for your health and that of your business. And, if you’re smart and deliberate about it, you can combine really hard, productive work with a healthy amount of time for the rest of your life. Plus, I really believe that instilling a healthy work-life balance as a core cultural value will give you business an advantage over the long run.

Books about leadership

  • Leaders Eat Last: Why Some Teams Pull Together and Others Don’t by Simon Sinek — Great leadership is critical to building a successful company and it’s not easy. Leadership is about fostering an environment where your team feels valued, fulfiled and inspired.
  • Start With Why by Simon Sinek — When communicating to inspire, you need to learn to start with your purpose, not what problem you solve or how you solve it.
  • Drive: The Surprising Truth About What Motivates Us by Daniel Pink — Guess what? Human motivation is more complicated than carrot-and-stick approaches assume. This struck me as obvious, but many businesses still approach motivation this way. It’s broken. Pink posits that autonomy, master and purpose are what really motivate us.
  • The Alliance: Managing Talent in the Networked Age by Reid Hoffman, Ben Casnocha,Chris Yeh — The way we work is changing and so must the way we manage.

Books about obstacles and overcoming them

  • David and Goliath by Malcom Gladwell — The first book in the lesson titled “Obstacles are actually opportunities.” Also makes the case that bigger is often not better. Well written, of course.
  • The Obstacle is the Way by Ryan Holiday — Part two in the series “Obstacles are actually opportunities.” Also really enjoyed learning more about Marcus Aurelias.
  • The Dip by Seth Godin — The number one reason startups fail? The founders give up. This short book helps you recognize the many dips you are going to face throughout this journey from the signs that you really should call it, wind things up gracefully and move on to the next thing.

Books about the future

  • Abundance: Why the Future is Better Than You Think by Peter Diamandis and Steven Kotler — You probably know someone who is basically pessimistic about the future. I mean there are a lot of seemingly rational reasons to be. Prescribe them this book and The Rational Optimist, below. Great book about how exponential technologies and innovative leaders are building a future where the basic needs of humanity will be readily available to all.
  • Bold: How to Go Big, Make Bank and Change the World by Peter Diamandis and Steven Kotler — The followup to Abundance focuses more on the incredible number and diversity of business opportunities available at this incredible time in history enabled by exponential technology.
  • The Third Industrial Revolution and The Zero Marginal Cost Society by Jeremy Rifkin — We’re in the midst of another industrial revolution and this one, based on exponential and sustainable technology, is leading inexorably to products and services that have zero marginal cost. The consequences are profound.
  • The Rational Optimist by Matt Ridley — The reason-based case for being optimistic about the future. Critical to adjust mindset to be able to fight through the hard work that is starting a business. Hope that you’re contributing to improving an already improving world is great fuel.
  • The Circle by Dave Eggers — It’s also good for founders to get a healthy dose of skepticism, and this book, which, incidentally, is the only fiction on this list, warns us to contemplate privacy very seriously in this rapidly changing age.

Books about growth and marketing

Books about the future of work

Books about particular companies and people

I’ve found out I’m a sucker for a good founding story. Here’s some books that will take you inside the founding moments of some of the most successful startups and impart some wisdom along the way.

Podcasts about business and startups

  • a16z — The Andreessen Horowitz podcast, high quality conversations on a wide variety of topics.
  • This Week in Startups — Jason Calacanis interviews founders and talks startup news.
  • Product People — Interview with people who make products.
  • How to Start a Startup — Sam Altman’s Fall 2014 Stanford class is packed with great advice from some of the startup scene’s biggest names.
  • Product Hunt — Ryan Hoover and Eric Torenberg talk products with their startup scene guests.
  • The Reboot Podcast — A unique and very useful podcast that delves into the emotional and soulful aspects of starting a business.
  • VentureBeat’s What to Think — A relatively lighthearted newsy tech podcast.
  • Marketplace — Perhaps my favorite source of business news.
  • Planet Money — Great way to learn about business and economics.
  • Freakonomics — Great stories about the unexpected aspects of economics.

So, what else should I listen to? Tweet me.