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Reboot’s 8 Most Recommended Practical-Tactical Books for Startup Leaders

How to build a healthy company and culture, fundraise, hire a team — and manage people, your finances, your board of directors, and yourself — consciously, skillfully, and successfully.

The bookshelf at the Reboot office is brimming with books on the nuts and bolts of running a company, as much as it’s full of good reads on psychology and the wisdom traditions.

There is a set of classic titles that we recommend often for new CEOs, seasoned founders, and anyone struggling with aspects of running their business from finance, hiring, fundraising, managing their board effectively, why vulnerability is important, how to think about organizational health, and all of the myriad other things that a founder needs to keep an eye on in a scaling business.

There are even a few titles on there for those new to startup life and what that means for the significant other in your life, as well as how to manage your own psychology and not get lost in the fire.

Below are Reboot’s topmost recommended books for startup leaders. If we had a lending library, these reads wouldn’t be sitting on our shelves for long before we passed them along to the hands of another leader.

  1. Startup CEO: A Field Guide to Scaling Up Your Business by Matt Blumberg
    A cogent and concise description of the most important parts of being a first-time CEO. If there was ever a playbook in how to do the job, this is it.
  2. Startup Boards: Getting the Most Out of Your Board of Directors by Brad Feld and Mahendra Ramsinghani
    As with all the books in the Startup Revolution series, this book is a handbook for making boards work. As Jerry notes in the forward, “Good boards don’t guarantee a company’s success but a bad board can guarantee its failure.” Read this and build a good board.
  3. Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist by Brad Feld and Jason Mendelson
    One of the biggest sources of pain and agita for any founder is fundraising. Moreover, most founders are at a clear disadvantage when it comes to negotiating with their investors (potential and otherwise). This is a succinct guide to one of the most needlessly arcane and painful aspects of building a venture-backed company.
  4. Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams by Matt Blumberg
    Like Startup CEO, this is a cogent, concise (despite its heft), and useful description for nearly every senior leadership position a first-time CEO can imagine. Buy it, keep it on your desk, and refer to it often.
  5. Why Startups Fail: A New Roadmap for Entrepreneurial Success by Tom Eisenmann
    Understanding why startups fail is probably the best way to strengthen the chances of your startup’s success. Eisenmann is more than a teacher and researcher; he’s been an active investor, and therefore witness, to dozens of successes and failures. This is a classic opportunity to learn from others’ mistakes.
  6. Powerful: Building a Culture of Freedom and Responsibility by Patty McCord
    Few people understand culture like Patty. Having been a witness to the creation of Netflix’s powerful and supportive culture, and having shaped it herself, Patty’s work is a tremendous guide for building cultures that go beyond right and wrong and right into the land of cultures that work.
  7. Ask Your Developer: How to Harness the Power of Software Developers and Win in the 21st Century by Jeff Lawson
    Jeff is the definitive Founder-CEO. His take, which is that other CEOs should ask their developers, breaks through the clutter of management theories and different leadership styles. His admonition to seek out the view of your developers is really a call to get as close as possible to both the product and then the customer.
  8. Reboot: Leadership and the Art of Growing Up by Jerry Colonna
    Reboot Co-founder and CEO Jerry Colonna reveals why radical self-inquiry is critical to professional success and healthy relationships in all realms of life. When it comes to surviving the startup life, taking care of your whole self is as essential to the rest of the work you do building your company. Better humans make better leaders, and better leaders create more humane work environments.



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Allison Schultz

Allison Schultz


Co-founder and coach @RebootHQ. Lifting up the wisdom of the equines for leaders of today so we can return to our truest self.