The Holy Trinity of Startup Books
A funny thing happens when you start a company. People share book recommendations. It happens more than I might have expected, concentrated in a genre that I didn’t know existed: organization, leadership and productivity.
I’ve read my fair share of this “startup founder” canon, and three books have stood out above the rest. They’re mostly helpful, occasionally cathartic, and sometimes transcend practicality altogether—veering into the arcane, like framing a clear email inbox as 'a mind like water' or extolling Advaita Vedanta’s view on ego dissolution.
For anyone trying to build something from nothing, these books offer a welcome reprieve from the steady chorus of self-doubt. That’s why I find myself recommending them to those gearing up for, or already deep in, the climb.
I’m not claiming to have reached the summit, but for those navigating the trail, here’s what I call the “holy trinity” of leadership, organization, and productivity books.
Getting Things Done: by David Allen
Getting Things Done (GTD) is the organization bible. The book inspired a base of devoted followers who gather for annual workshops, conferences, and a GTD subreddit with nearly 50k members which, according to Reddit, is a top 3% subreddit by size.
The system uses a basic flow chart logic. Capture everything on paper, decide if it's actionable (trash, reference, incubate, or define the next action), organize tasks into appropriate lists (next actions, projects, waiting for, calendar, someday/maybe). Review often.
This method should be taught in high schools as core vocational training. It doesn’t care about the latest technology or workflow hack. It works with paper and pencil, or your email inbox. Andreas Klinger adapted this system brilliantly to Gmail in 2013, and no modern inbox tool (Superhuman, etc.) has matched it since. I’ve made Klinger’s inbox zero mandatory at 3i, because it's the best way to ensure the team adopts the GTD method.
I’ll note: it’s not for everyone. I once tried putting my writer friend on to the GTD method. Unconditioned for desk work, he thought it was total madness. Like the weekend runner attempting a marathon, cold. Don’t take this method lightly.
GTD was recommended by my investor, advisor and friend Miles Lasater over lunch in New Haven in 2021, in the formation days of 3i. It’s been a necessary tool to stay organized through the extraordinary communication volume of a 600 member investment network. For those who don’t know Miles, he is an entrepreneur, venture capitalist and great dude. He’s got more gems in his weekly, three-point newsletter that you can follow here.
The 15 Commitments of Conscious Leadership
If Getting Things Done is for productivity, 15 Commitments is for “leadership” which – whether you care about the word or not – is something you are forced to reckon with as a CEO.
The core learning of the book is to stay above “the line”. Be open, curious, responsible, and growth oriented. Acting below the line is defensive, reactive, and blame-focused. Use “the line” as a litmus test for your behaviors, and adjust accordingly. Revisit the line as often as you can.
While this book has plenty of bullet-point-business-practicalism — like stay above the line, eliminate gossip, be the resolution, speak candidly, make clear contracts – it makes one of the boldest forays into spirituality I’ve ever seen for a book of its type. It extends concepts of leadership into ideas of self, being, and presence.
Take, for example, its teaching on the shift from “to me” → “by me” → “through me” → “as me”. The shift from “To Me” to “By Me” is a move from victimhood to responsibility. Makes a certain sense. But “Through Me” and “As Me” go further, reframing leadership as something beyond personal willpower, where you surrender total control. The authors warn lay readers that “through me” and “as me” are life pursuits, and not to be taken lightly. I like their ambition. Kind of silly for a book on management, though.
I revisit and recommend this book often. I constantly think about the line, and whether I’m above it or below it. 15 Commitments was recommended by Jeff Levere, an executive coach I met through one of my business partners Josh Gordon. Jeff is a Stanford GSB private equity guy who dedicated his life to coaching entrepreneurs.
The Great CEO Within
By Matt Mochary and Alex MacCaw
For practical playbooks on business operation, read The Great CEO Within. Matt Mochary is perhaps the best known CEO coach in Silicon Valley. He’s the in-house specialist at Sequoia, and has coached many of the greats, like CEOs of Coinbase, Opendoor, and Clearbit. I met Matt when he was raising his venture fund, Fortius, which was introduced by a 3i member.
Matt’s book, the Great CEO Within, is like an operating system for running a startup. This one is much more tactical. It contains specific, playbook level detail on how to run your day, week, month, quarter and year. How to give feedback, run meetings, set goals, manage a board, negotiate contracts, and communicate a vision.
I’ve adopted much of Matt’s methodology, like weekly all
Hands and management meetings, and have failed terribly at implementing some of Matt’s advice, like a botched conflict resolution session between two employees that I confidently led after reading his paragraph on the matter, only to make the disagreement significantly worse. A good reminder that these books are written by pros.
The book is written plainly, and I’ve re-read it many times. Like a good TV show, I notice different things every pass, based on the stage we’re at, or the recent challenge we face.
I do love these books, and this genre. They remind me to view leadership as an acquired skill, not a born trait. They hold different meanings through different phases of the startup journey. Please pass along other recommendations you might have. I’d love to grow the list over time.