From Bootstrapping to Buyout: A Decade of Audiobooks That Tracked My CEO Journey
Audiobooks are my default soundtrack: driving, tractor time, kids’ hockey practice, runs, and whatever chore is next. I mostly stick to non‑fiction, and I started wondering whether my listening habits shifted as my job evolved from scrappy founder to CEO of a scaling tech company. To test it, I paired my Audible history with headcount estimates from People Data Labs and used a model to surface the trends. One note up front: the themes and yearly overviews were written by an AI model (GPT-OSS:120b) so none of my biases from classified or proprietary work bleeds into the analysis or writeup.
Yearly Reading Trends
2012-2015: 1 - ~8 employees
These were bootstrapping years where I was both an individual contributor as well as a manager. I used my driving time to catch up on phone calls and hadn’t yet gotten hooked on audio books.
2016: ~24 employees, 53 audiobooks
Intelligence & Espionage: Many titles focus on CIA, NSA, covert operations, and intelligence analysis, showing a strong interest in secret-statecraft.
Leadership & Personal Effectiveness: Numerous self‑help and leadership books indicate a focus on improving personal and organizational performance.
Geopolitics & China: Several works examine China’s rise, strategy, and global impact, reflecting a preoccupation with Asian power dynamics.
Cybersecurity & Digital Threats: Titles about hackers, cyber war, and digital manipulation show a concern for technology‑driven security issues.
Business & Finance: A cluster of books on entrepreneurship, investing, and Wall Street narratives points to a strong business interest.
Military History & Strategy: Many titles recount historic wars, generals, and strategic doctrines, indicating a fascination with conflict and its lessons.
Overview: The 2016 list reveals a reader drawn to power structures—whether covert intelligence, geopolitical shifts, or corporate leadership—while also seeking historical context and practical self‑improvement.
2017: ~29 employees, 117 audiobooks
Espionage & Intelligence: A large portion of titles focus on spies, CIA, KGB, and covert operations, indicating a strong interest in secret‑service narratives.
Military History & Warfare: Numerous books cover battles, military strategy, and elite forces, showing a fascination with war and its tactics.
Leadership & Management: Many titles offer advice on leading people, organizations, or nations, reflecting a desire for personal and professional development.
Geopolitics & Global Power Shifts: Titles examine China, Russia, North Korea, and the rise/fall of nations, indicating a focus on world‑order dynamics.
Technology, Cybersecurity & Future Forecasts: Books on hacking, DARPA, cyber‑weapons, and predictive science reveal curiosity about tech’s impact on security and society.
Economics, Business & Market Forces: Several titles explore finance, private equity, and economic influence, pointing to an interest in how money shapes power.
Overview: The 2017 list shows a reader drawn to power—whether hidden in espionage, overt in military campaigns, or exercised through leadership, geopolitics, technology, and finance—seeking both historical depth and forward‑looking insight.
2018: ~47 employees, 179 audiobooks
Geopolitics & Great Power Competition: Many titles focus on China, US strategy, and global power shifts, indicating a strong interest in international power dynamics.
Leadership & Management: Numerous books address leadership principles, organizational health, and personal effectiveness, showing a focus on improving leadership skills.
Military History & Strategy: A large subset of titles recount wars, battles, and strategic doctrines, reflecting fascination with military past and theory.
Technology & Future Trends: Books on AI, superintelligence, data, and emerging tech dominate, indicating curiosity about technological impact on society.
Economics & Business Innovation: Titles covering economics, market forces, and startup ecosystems show a drive to understand and participate in modern business.
Overview: The 2018 list reveals a reader deeply engaged with global power shifts, leadership mastery, and the forces reshaping society—military history, cutting‑edge technology, and economic innovation dominate.
2019: ~58 employees, 180 audiobooks
Geopolitics & War: A large portion of titles focus on conflicts, intelligence operations, and strategic history across centuries and regions.
Cybersecurity & Digital Threats: Many books examine hacking, cyberwarfare, and the impact of technology on security and society.
Leadership & Management: Numerous titles offer advice on leading teams, business strategy, and organizational effectiveness.
Economic & Financial History: Several books explore the evolution of finance, capitalism, and the influence of major economic figures.
Biographies & Personal Memoirs: The list includes many life stories of political, military, and business leaders, offering personal perspectives on history.
Self‑Improvement & Purpose: Several titles provide practical guides to finding meaning, negotiating, and personal growth.
Overview: The 2019 list reveals a reader fascinated by power dynamics—whether on battlefields, in cyberspace, or corporate boardrooms—while also seeking personal insight and historical context through biographies and self‑help guides.
2020: ~76 employees, 111 audiobooks
Leadership & Management: Numerous titles focus on how leaders think, act, and build culture in business and government.
War & Military History: A large portion of the list examines battles, strategies, and personal accounts from past conflicts.
Politics & Power: Many books explore political figures, statecraft, and the mechanics of governance.
Pandemic & Health: COVID‑19 and broader health topics appear repeatedly, reflecting the year’s global crisis.
Technology & Innovation: Several titles discuss breakthroughs, digital transformation, and the future of tech industries.
Economics & Finance: Books on economic theory, markets, and financial history dominate a notable segment of the list.
Overview: The 2020 reading list reveals a voracious appetite for understanding power—whether in boardrooms, battlefields, or governments—while also grappling with the unprecedented pandemic, the role of technology, and the forces shaping economies worldwide.
2021: ~77 employees, 187 audiobooks
Leadership & Management: Numerous titles focus on leading people, organizations, or personal growth, indicating a strong interest in leadership principles.
Geopolitics & History: Many books examine wars, empires, and international power struggles, showing a fascination with global historical dynamics.
Technology & Innovation: A large subset covers cutting‑edge tech, AI, space, and the impact of new inventions on society.
Finance & Business Strategy: Frequent titles on startups, venture capital, financial crises, and corporate governance point to a focus on business economics.
Security & Intelligence: Several works explore espionage, cyber‑warfare, and defense, reflecting interest in modern security challenges.
Personal Memoir & Storytelling: A notable number of titles are memoirs or narrative accounts of individual experiences across varied fields.
Overview: The 2021 list reveals a reader drawn to leadership lessons, deep dives into geopolitical history, and the forces reshaping society through technology and finance, while also valuing real‑world narratives of adventure, espionage, and personal transformation.
2022: ~103 employees, 171 audiobooks
Great Power Geopolitics: Numerous titles focus on China, the United States, and global strategic competition, reflecting a strong interest in international power dynamics.
Leadership & Management: Many books address how to lead, build teams, and improve organizational culture, indicating a focus on professional growth.
Military History & Strategy: A large subset of titles recount wars, battles, and strategic doctrines, showing a fascination with historical and contemporary warfare.
Personal Development & Well‑Being: Several books offer self‑improvement advice, from stress management to habit formation, pointing to a personal growth agenda.
Economics, Finance & Business Innovation: Titles explore markets, entrepreneurship, and economic history, indicating a keen interest in financial systems and business strategy.
Science, Technology & Future Trends: Books on quantum theory, biotech, and emerging tech suggest curiosity about scientific breakthroughs and their societal impact.
Overview: The 2022 list reveals a reader deeply engaged with global power shifts, especially U.S.–China rivalry, while also pursuing leadership mastery, historical warfare, personal growth, and the economic and technological forces shaping the future.
2023: ~143 employees, 130 audiobooks
Great Power Geopolitics: Numerous titles focus on China, Russia, Iran, and US strategic competition, indicating a strong interest in global power dynamics.
Leadership & Management: Many books address leadership principles, corporate culture, and executive performance, showing a focus on professional growth.
Personal Development & Resilience: Titles about mindset, trauma, peak performance, and happiness suggest a drive toward self‑improvement and mental health.
Historical & Military History: A large portion of the list covers wars, biographies of military figures, and empire histories, reflecting a fascination with the past.
Economics & Finance: Books on money, markets, and economic theory appear repeatedly, indicating interest in financial literacy and macro‑economics.
Technology, AI & Space: Several titles explore emerging tech, artificial intelligence, and space strategy, pointing to curiosity about future tech frontiers.
Overview: The 2023 list blends a deep dive into global power shifts with a strong appetite for leadership, personal resilience, and historical context, while also tracking financial savvy and emerging technologies, revealing a reader who balances macro‑strategic curiosity with personal and professional growth.
2024: ~176 employees, 63 audiobooks, started M&A process
War & Geopolitics: A large share of titles examine historic and contemporary conflicts, strategy, and global power shifts.
Leadership & Management: Many books focus on leading people, organizations, or nations in challenging contexts.
Personal Growth & Well‑Being: Numerous titles address self‑improvement, health, aging, and mental resilience.
Economics & Finance: Several books explore monetary policy, inflation, wealth, and investment strategies.
Innovation & Entrepreneurship: A cluster of titles discuss startup tactics, venture capital, and creative problem‑solving.
China & Asian Power Dynamics: Multiple works specifically analyze China’s rise, policy, and societal trends.
Overview: The 2024 list reveals a reader fascinated by power—whether on battlefields, boardrooms, or personal life—while also probing economic systems, innovative entrepreneurship, and the shifting influence of China in global affairs.
2025: ~172 employees, 46 audiobooks, company acquired
Military History & Strategy: Numerous titles focus on wars, battles, and military leaders, indicating a strong interest in historical conflict and strategic thinking.
Business & Entrepreneurship: Many books examine companies, founders, and growth tactics, showing a focus on corporate success and startup culture.
Economic Theory & Finance: Titles on capitalism, market crashes, and investment suggest a keen interest in macro‑economic forces.
Innovation & Technology: Several works explore disruptive tech, scaling, and the impact of new inventions, reflecting curiosity about the future of tech.
Geopolitics & Power: Books on diplomatic history, global leaders, and national cycles reveal an interest in how power is exercised worldwide.
Personal Development & Leadership: Titles about meaning, measurement of life, and leadership lessons indicate a desire for self‑improvement and effective leadership.
Overview: The 2025 list blends deep dives into war and strategy with a strong appetite for business acumen, economic insight, and tech disruption, while also seeking personal growth and understanding of global power dynamics.
2026: on sabbatical, 14 books read as of 2/21/2026
Technology & AI: Several titles explore future tech, networks, and AI’s impact on society.
Historical Biography: Many books focus on the lives of influential historical figures.
Geopolitics & Global Power: Titles address strategic competition, world order, and military influence.
Economics & Personal Finance: One title directly tackles money management, reflecting interest in financial wellbeing.
Science & Physics: A dedicated physics primer signals curiosity about fundamental scientific concepts.
Regional & Cultural History: Books on India, Tibet, and Chinese internet show a focus on diverse cultural narratives.
Overview: The 2026 list blends cutting‑edge tech curiosity with deep dives into historical figures and global power dynamics, while also touching on personal finance, fundamental science, and diverse cultural histories, suggesting a reader eager to understand both the forces shaping the future and the legacies of the past.
Theme Shifts Across Years
Big picture: From 2016 to 2026 the reader consistently pursues power structures—political, military, corporate—and couples that with personal growth, while technology and global competition grow from background to central focus.
Persistent Themes
Leadership & Management (2016‑2026): Appears every year as a core interest in personal effectiveness and organizational influence.
Geopolitics & Global Power (2016‑2026): Consistently tied to great‑power competition, China, and war, reflecting a macro‑strategic curiosity.
Military History & War (2016‑2025): Repeatedly resurfaces, showing a fascination with conflict as a lens on power.
Economics & Finance (2016‑2026): Featured each year, indicating a steady need to understand markets and financial systems.
Technology & Innovation (2017‑2026): Evolves from cybersecurity to AI and space, marking an enduring interest in future‑shaping tools.
Phase Shifts
2016-2019: From broad power themes to a blend of cyber threats and personal self‑help. Dominant themes: Intelligence & Espionage, Cybersecurity, Self‑Improvement Note: Reader balances external power with internal development.
2020-2022: Pandemic urgency pushes health and politics to the fore while great‑power geopolitics intensify. Dominant themes: Pandemic & Health, Politics & Power, Great Power Geopolitics Note: Global crisis reshapes the power lens.
2023-2026: Technology, AI, and science dominate, and personal resilience becomes a key focus. Dominant themes: Technology & AI, Personal Development & Resilience, Science & Physics Note: Future‑oriented curiosity overtakes earlier espionage focus.
Inflection Points
2020: Sudden inclusion of Pandemic & Health and heightened political power themes. Likely driver: COVID‑19 global disruption and its impact on societies.
2023: Rise of AI, space, and personal resilience themes, while classic espionage fades. Likely driver: Rapid AI breakthroughs and post‑pandemic focus on mental fortitude.
Rising themes: Technology & AI, Science & Physics, Personal Development & Resilience, Innovation & Entrepreneurship, Regional & Cultural History
Declining themes: Espionage & Intelligence, Classics & Narrative Fiction, Pandemic & Health, Security & Intelligence
Stable themes: Leadership & Management, Geopolitics & Global Power, Economics & Finance