23 Books for 2026 - The Best Reading Advice from Fintech Leaders
23 book recommendations from some of the world's best tech and fintech founders, CEOs, and investors.
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Over the course of 2025, several of my guests have recommended excellent books. The result is this collection: 23 books read by some of the world’s most innovative founders, business leaders, and investors.
Spanning categories from Business Building to Philosophy, these recommendations reveal how today’s leaders draw insights from different fields. While business books dominate with works like “The Outsiders” and “The Hard Thing About Hard Things,” the inclusion of titles like Thich Nhat Hanh’s “No Death, No Fear” and Karen Pryor’s “Reaching the Animal Mind” offer intimate glimpses into how great leaders seek wisdom beyond their industry.
Whether you’re building a company, investing in startups, or simply passionate about making better decisions in complex environments, this collection offers unique perspectives from those who have successfully navigated similar challenges.
I’ve included the Amazon links for every book… which ones will you read in 2026?
Key Takeaways
Most recommended: “Shoe Dog,” “The Outsiders,” “How to Make a Few Billion Dollars,” and “The Hard Thing About Hard Things” lead with multiple recommendations.
Books as tools: Leaders actively re-read many of these books during specific challenges rather than reading only once.
Diverse sources: Recommendations span from business classics to leadership philosophy and even animal behavior science.
Essential Business Building Books
“Shoe Dog” by Phil Knight (3 recommendations)
Recommended by: Howard Lindzon (StockTwits Founder), Anre Williams (Amex Bank CEO), and Savneet Singh (PAR Technology CEO)
Howard calls it “great for business” while Anre connected deeply with it as a former athlete: “A book that stayed with me... I thought I knew about the company because I started using it when they were not well known.” It captures the long-term entrepreneurial journey and resonates with founders who are in it for the long haul. This book was also one of the most recommended books of my 2024 guests.
“The Outsiders” by William Thorndike (2 recommendations)
Recommended by: Savneet Singh (PAR Technology CEO) and Art Levy (Brex)
Savneet gives this to most CEOs of larger companies because “it’s an incredible way to remember what your most important job is.” Art values it for its perspective on M&A as “just a capital allocation method, just like buying back shares.” Essential reading for leaders thinking about capital allocation and long-term value creation.
“How to Make a Few Billion Dollars” by Brad Jacobs
Recommended by: Savneet Singh (PAR Technology CEO) and Art Levy (Brex)
Savneet says “it kind of hit me as far as an operator and understanding the weeds.” Art also values this for its practical operational insights from a serial acquirer who has built multiple billion-dollar companies through disciplined M&A.
“The Hard Thing About Hard Things” by Ben Horowitz (2 recommendations)
Recommended by: Nico Simko (Clair CEO) and Art Levy (Brex)
Nico’s endorsement is powerful: “By far, if anybody’s interested in the startup journey, I would really recommend reading this... 99.9% of the time, I’m dealing with problems or issues or questions that no one else was able to solve. You need to be comfortable in discomfort.” It functions almost like a crisis management manual. This book was also one of the most recommended books of my 2024 guests.
“Gambling Man” by Lionel Barber
Discussed by: Lionel Barber (Author & Former FT Editor)
I had the privilege of sitting down with Lionel Barber in New York, to discuss his definitive biography of Masayoshi Son and SoftBank. Lionel walked an hour through freezing temperatures to meet me (he’s an avid outdoorsman). The book offers an unprecedented look into one of tech’s most audacious risk-takers and the empire he built.
“Never Split the Difference” by Chris Voss
Recommended by: Art Levy (Brex)
Art’s number one book recommendation: “An amazing negotiating book. It’s all about how negotiation has to be a win-win. It’s a repeated game. It’s extremely tactical and helpful. It’s literally on my desk here because whenever I’m going into a tense negotiation, I flip to a page to try to remember.”
“Amp It Up” by Frank Slootman
Recommended by: Eynat Guez (Papaya CEO)
She said: “I currently read Amp It Up, which is a great book of Frank, and that was the CEO of ServiceNow and Snowflake until recently. And sometimes, when you understand that, you know they were not always great company. They eventually kind of needed to build them to be, to be great companies.”
“Know What Matters” by Ron Shaich
Recommended by: Savneet Singh (PAR Technology CEO)
“Ron’s involved with PAR, investor at PAR, former CEO of Panera, founder of Panera. I thought it’s a great book. It’s almost a manual of how to run a great company.” A practical guide from one of the most successful restaurant entrepreneurs.
“Reminiscences of a Stock Operator” by Edwin Lefèvre
Recommended by: Howard Lindzon (StockTwits Founder)
Howard calls it “probably the only investment book you need to read... it’s hard to beat the market over time. It’s great stories that are timeless fear and greed.” A century-old classic that remains essential.
“Who” by Geoff Smart & Randy Street
Recommended by: René Lacerte (Bill CEO)
René uses the scorecard approach from this book: “A scorecard is a better way to actually define what you want than a job description. Job descriptions tend to be about skills, and scorecards tend to be about outcomes.” Essential reading for anyone building a team.
“Self Made Boss” by Jackie Reses & Lauren Weinberg
Written by: Jackie Reses (Lead Bank CEO)
It was fun to interview Jackie again this year - it was our third podcast together. A few years ago, she co-authored this essential guide offering tools and guidance for micro entrepreneurs. Jackie brings decades of experience from Square, Alibaba, and now Lead Bank to help small business owners succeed.
“Death by Meeting” by Patrick Lencioni
Recommended by: Steve Stagner (Crete CEO)
Part of Steve’s Lencioni collection. “I can’t get enough of Lencioni. He’s just amazing.” A practical guide to making meetings actually productive.
Leadership & Team Building
“Extreme Ownership” by Jocko Willink & Leif Babin
Recommended by: Steve Stagner (Crete CEO)
Steve calls it “a very good foundational book” and pairs it with The Founder’s Mentality to “nail down just the basics of leadership.” Essential for leaders building accountability cultures.
“The Founder’s Mentality” by Chris Zook & James Allen
Recommended by: Steve Stagner (Crete CEO)
Paired with Extreme Ownership, Steve says “those two books really nail down just the basics of leadership.” A guide to maintaining startup energy as companies scale.
“The Five Dysfunctions of a Team” by Patrick Lencioni
Recommended by: Steve Stagner (Crete CEO)
Steve is a big Patrick Lencioni fan: “I can’t get enough of Lencioni. He’s just amazing.” He maintains a suggested reading list that includes multiple Lencioni titles including Death by Meeting.
“The Score Takes Care of Itself” by Bill Walsh
Recommended by: John Waldmann (Homebase CEO)
John gives his entire team a book every year. This one stands out “from an operational discipline standpoint, what it takes to build a great team... a constant reminder for everybody who is managing a team.”
“Unreasonable Hospitality” by Will Guidara
Recommended by: John Waldmann (Homebase CEO)
“A constant reminder for what it means to be in service, which is one of our core values as a company.” John gave this to his entire Homebase team.
“Disney’s Land” by Richard Snow
Recommended by: John Waldmann (Homebase CEO)
“The creation of Disneyland, incredible story about how the attention to detail and the focus on quality and experience leads to something far bigger.” Given to his team as they build magical experiences for local businesses.
Psychology & Behavior
“Sapiens” by Yuval Noah Harari
Recommended by: Ryan Graciano (Credit Karma Co-Founder)
“I can always recommend Sapiens to people... gives you some insight into how big groups think.” A sweeping history that helps leaders understand human behavior at scale.
“Reaching the Animal Mind” by Karen Pryor
Recommended by: Ryan Graciano (Credit Karma Co-Founder)
An unexpected recommendation from a fintech founder: “Such a good primer into how behavior really works across species... the more you learn about the mechanics of animal behavior, the more you start to recognize in yourself.” Ryan adds: “By trying to learn about dogs, you actually learn a lot about yourself.”
“The Magic of Believing” by Claude M. Bristol
Recommended by: Yoshi Yokokawa (Alpaca CEO)
“That book really allowed me to think about - imagine something actually doable. If you think about it, it’s actually doable. If you cannot even plan it, you won’t even do it.” Yoshi credits this mindset for achieving his green card and building Alpaca.
Philosophy & Perspective
“No Death, No Fear” by Thich Nhat Hanh
Recommended by: René Lacerte (Bill CEO)
The most personal recommendation: “When my dad was dying, I was reading it, and it really helped me understand and appreciate the circle of life... it really helps you have an appreciation that we do not understand death, so there’s no reason to be afraid.” René gifts this to people who have lost someone meaningful.
“Open” by Andre Agassi
Recommended by: Howard Lindzon (StockTwits Founder)
“About just the torment of being number one in sports and everything that came with it is pretty cool, like, be careful what you wish for.” A cautionary tale about the price of success.
Great curated list—several of these, like The Outsiders and How to Make a Few Billion Dollars, dive into capital allocation and operational rigor that directly applies to trade credit, working capital, and liquidity decisions. TCLM often explores that same financial operations layer for B2B leaders. Might be a useful complement to your reading list.
(It’s free)- https://tradecredit.substack.com/
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