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How Cameron Built 3 Different $100M Companies

Dec 1, 2025

Guest

Cameron Herold

Cameron Herold, a serial entrepreneur and former COO of 1-800-GOT-JUNK, shares his journey of building three $100M companies. He talks about how he transformed his learning differences into strengths, the importance of culture and hiring athletes to motivate teams, and the critical need for psychological safety in leadership. Cameron also dives into the reality of nearly bankrupting a company due to cash mismanagement and offers insights on investing and balancing work-life through his digital nomad lifestyle.

01:55:40

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ADVICE

Build Business For Freedom

Design your company around the lifestyle you want and reverse-engineer systems to protect that freedom.
Build teams, processes, and locations so you can run the business while living where you choose.

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ANECDOTE

Coat Hanger Hustle At Age Seven

At seven Cameron cold-called dry cleaners to negotiate payments for recycled coat hangers and lied to his mom while collecting them.
That first hustle taught him negotiation, tenacity, and cold-calling fundamentals.

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ADVICE

Reverse-Engineer Revenue Metrics

Reverse-engineer your financial goals into exact activities and metrics required each week.
Break revenue goals into job counts, estimates, conversion rates, and marketing actions and coach to those numbers.

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Cameron's Nomadic Lifestyle and Why He Chose Entrepreneurship

01:45 • 3min

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Early Hustles: Coat Hangers to Campus Franchises

04:30 • 6min

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Learning Differences and Choosing Business Over School

11:00 • 4min

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Scaling College Pro Painters: Systems and Recruitment

14:59 • 7min

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Making Painting Sexy: Culture and Pay-for-Performance

22:22 • 2min

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From Painting to Auto Body: Boyd/Gerber Growth Lessons

24:45 • 7min

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Private Currency and Barter Economy (ITEX)

31:35 • 9min

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Joining 1-800-GOT-JUNK: From Consultant to COO

41:03 • 3min

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Delegation, Reverse Engineering Goals, and Leadership Rigor

43:42 • 5min

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How to Brief Teams and Hit Targets

The Cash Crisis: Near Bankruptcy at $60–80M

55:48 • 6min

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Building Psychological Safety and Entrepreneurial Reality

01:02:14 • 10min

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Branding, PR, and Media Wins

01:11:49 • 3min

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Hiring and Developing Talent: A-Players Are Free

01:15:10 • 11min

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Invest In Your Leaders: Time, Priority, Delegation

01:26:37 • 13min

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COO Alliance and Second-in-Command Community

01:39:30 • 1min

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Becoming a Digital Nomad: Lessons from Travel

01:40:40 • 5min

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Wealth, Investing, and Pulling Chips Off the Table

01:45:14 • 5min

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Legacy, Kids, and What Matters Most

01:49:55 • 2min

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Current Struggles: Marriage and Personal Work

• Mentioned in 3 episodes

The Second in Command

Cameron Herold

#380

• Mentioned in 60 episodes

Autobiography of a Yogi

Paramahansa Yogananda

This book is a detailed account of Paramahansa Yogananda's life, from his childhood in India to his spiritual quest and eventual establishment of the Self-Realization Fellowship in the United States. It includes his encounters with various spiritual figures, his experiences with Kriya Yoga, and his mission to spread the teachings of yoga and meditation to the Western world. The book also delves into the prophesied writing of his autobiography and its significance in spreading the message of yoga globally.

#2660

• Mentioned in 14 episodes

Vivid Vision

Cameron Herold

#88

• Mentioned in 154 episodes

Outliers

The Story of Success

Malcolm Gladwell

In 'Outliers: The Story of Success', Malcolm Gladwell examines the often-overlooked factors that contribute to high levels of success. He argues that success is not solely the result of individual talent or hard work, but rather is influenced by a complex web of advantages and inheritances, including cultural background, family, generation, and luck. The book delves into various examples, such as the success of Bill Gates, the Beatles, and Canadian ice hockey players, to illustrate how these factors play a crucial role. Gladwell also discusses the '10,000-hour rule' and the impact of cultural legacies on behavior and success. The book is divided into two parts: 'Opportunity' and 'Legacy', each exploring different aspects of how success is achieved and maintained.

#81

• Mentioned in 171 episodes

Traction

Get a Grip on Your Business

Gino Wickman

In Traction, Gino Wickman provides a systematic approach to achieving business success through the Entrepreneurial Operating System (EOS). The book focuses on six key components: Vision, People, Data, Issues, Process, and Traction. It helps business leaders clarify their vision, align their leadership team, solve common business problems, and foster healthy communication and discipline within the organization. The EOS system is designed to help businesses overcome frustrations such as lack of control, people issues, insufficient profit, hitting the ceiling, and feeling stuck. The book offers practical tools, real-world examples, and actionable strategies to drive sustainable growth and improve business operations.

#216

• Mentioned in 90 episodes

The E-myth

why most businesses don't work and what to do about it

Michael E. Gerber

The E-Myth Revisited by Michael E. Gerber dispels the myths about starting your own business, highlighting that most small business owners are not true entrepreneurs but rather technicians skilled in their trade. Gerber introduces the concept of the 'E-Myth' and explains that business owners must embody three key roles: the Entrepreneur (the visionary), the Manager (the organizer), and the Technician (the doer). The book emphasizes the distinction between working 'on' your business and working 'in' your business, and provides practical advice on building systems and processes to ensure a business can run independently of its owner.

#23820

• Mentioned in 2 episodes

Free PR

Cameron Herold

#537

• Mentioned in 47 episodes

Endurance

Shackleton's Incredible Voyage

Alfred Lansing

This book details the almost two-year struggle for survival of the 28-man crew of the Endurance, which was beset and eventually crushed by ice floes in the Weddell Sea during the Imperial Trans-Antarctic Expedition of 1914-1917. The crew drifted on ice floes, salvaged lifeboats, and eventually reached Elephant Island. Shackleton then led a perilous journey to South Georgia Island to secure rescue, culminating in one of the most remarkable survival stories in history. Lansing's narrative is based on extensive research, including interviews with surviving crew members and access to their diaries and personal accounts.

What does it take to build not one… but three different $100M companies? In this episode of the Disruptors Podcast, Steve Trang sits down with Cameron Herold, the former COO of 1-800-GOT-JUNK and the business strategist behind some of the fastest-scaling companies in North America. Cameron unpacks how he turned his unique brain ADHD, bipolar traits, and dyscalculia into a competitive advantage that helped him grow iconic brands, scale teams across continents, and build systems that work at $1M or $100M.

Follow Cameron Herold https://www.youtube.com/@CameronHerold

https://www.facebook.com/cameronherold/

https://cameronherold.com/

Cameron's TED TALK https://www.ted.com/speakers/cameron_herold

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