Books I Like
How does a book get on this list?
I recently moved and have several boxes of books I like to read. The true test is to see if the book made the recent move, if so, it’s reached a special place. This list of books moved from “fun read” to "reference" status - ones I have consulted over the past 25+ years. The list below is a few of those books that go back to my graduate school days.
Business Model Generation by Alexander Osterwalder and Yves Pigneur
NOTE: The OG of startup books -- I have the original version over 20 years old!
This book introduces the Business Model Canvas—a visual framework for defining and refining how a business creates, delivers, and captures value. It helps founders explore different customer segments, revenue models, and channel strategies before committing resources. The book encourages lean experimentation and rapid iteration, making it ideal for pre-seed and seed-stage startups. Investors can assess whether a founder truly understands their business model and go-to-market strategy. It’s a shared language for structuring and testing startup ideas quickly and clearly.
Why Read it?
It’s the OG that started the lean revolution!
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Crossing the Chasm by Geoffrey A. Moore
Moore’s classic explains why so many promising startups fail to gain mainstream traction after early success with visionary users. His “chasm” concept teaches founders to target a focused niche and establish credibility before broad scaling. The book’s insights on positioning, market segmentation, and messaging are critical for SaaS and enterprise startups. Investors use this framework to spot GTM (go-to-market) risk and evaluate whether a team is ready for expansion. It’s an indispensable roadmap for growing from product-market fit to real market leadership.
Why Read it?
Timeless framework on GTM and market risk.
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The Goal by Eliyahu M. Goldratt
The Goal introduces the Theory of Constraints (TOC), a powerful method for identifying and improving bottlenecks in any system. Though set in a manufacturing context, its lessons translate directly to product development, operations, and growth-stage challenges in startups. Founders will gain insight into how to drive throughput and avoid optimizing the wrong things. Investors can use TOC to assess operational discipline and identify scaling risks. It’s a timeless framework for improving flow, focus, and leadership alignment in high-growth environments.
Why Read it?
Constraint theory is everywhere and shapes most of decisions. What to work on next and why….
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Seed Deals by David Willbrand
Seed Deals demystifies early-stage startup financing, providing a founder- and angel-friendly walkthrough of term sheets, SAFEs, convertible notes, and equity. David’s informal, clear style makes legal and financial concepts accessible without dumbing them down. Founders will learn how to protect their long-term interests while fundraising effectively. Investors will better understand how to structure deals that align incentives and minimize friction. It’s a practical field manual for anyone involved in seed-stage startup funding.
Why Read it?
Dymistifies raising money. Entrepreneurs need an education, and David is here to help!
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Managing Corporate Lifecycles by Ichak Adizes
This book outlines the predictable stages organizations pass through as they grow, each with its own leadership and operational challenges. Founders will learn when and how to shift their management style as complexity increases. Adizes’ model helps anticipate when to professionalize, restructure, or refocus without stalling innovation. Investors can use this lifecycle lens to diagnose organizational growing pains and support transitions more effectively. It’s especially useful for scaling companies facing internal misalignment or leadership friction.
Why Read it?
Not enough is known or discussed about the organizational and cultural challenges of startups. The Founder’s Trap is real!
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Anything from Brett Queener – Operator, Investor, Advisor
Brett Queener’s content—spanning interviews, essays, and conference talks—is a goldmine for early-stage SaaS founders. His deep expertise in founder-led sales, GTM repeatability, and Ideal Customer Profiles (ICPs) makes him a go-to resource on scaling revenue. Queener focuses on executing with discipline, avoiding premature hires, and validating sales math early. Investors trust his frameworks for evaluating GTM strategy and team readiness. He’s a rare blend of operator empathy and strategic clarity.
Why Read it?
Clear-headed thinker and realist about tech.
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The Fifth Discipline Fieldbook by Peter Senge
This book offers practical tools for building adaptive, learning-focused organizations grounded in systems thinking. Founders will find actionable techniques for team learning, shared vision, and addressing unspoken mental models. It’s modular and accessible—ideal for tackling specific cultural or communication challenges as companies scale. Investors can use it to evaluate leadership maturity and organizational resilience. The Fieldbook promotes smarter, more self-aware companies that learn and improve faster than the competition.
Why Read it?
I am a systems guy and a closet OD person – love this framework, super OG!
