How entrepreneurial identity, peer communities, and servant leadership drive long-term success

Executive overview

Most business leaders optimise for performance but neglect the communities, soft skills, and human care that actually compound over time. Cameron Herold grew up in an entrepreneurial household where freedom mattered more than money, built a career as a second-in-command, and now runs global peer networks for COOs and operations leaders.

The through-line: success comes from being in the right rooms, giving before taking, and caring about people as humans first.

The fastest path forward is rarely self-reliance — it's finding who already knows the way.

Growing up entrepreneurial

• Herold had 16 ventures by age 18 and 12 employees by age 20.
• The family framing: entrepreneurship was about controlling time, not accumulating money.
• School was hostile — 17 of 18 ADD markers made memorisation impossible; he learned to find shortcuts instead.
• That shortcut mindset became a professional advantage: pattern-match to what works, skip what doesn't.

The COO role defined

• The COO's job is to be the yin and yang to the CEO — strong where the CEO is weak.
• The role is not fixed; it maps to whatever the CEO cannot or will not do.
• Example: at 1-800-GOT-JUNK, Herold ran sales, marketing, ops, PR — but not IT or finance.
• COO Alliance was created because second-in-commands had no peer group of their own.

Why peer communities compound

• Herold has invested over $500,000 in mastermind communities across 15 years and estimates 10X returns.
• Communities attended: Entrepreneurs' Organization, Genius Network, Strategic Coach, Baby Bathwater, Mastermind Talks, TED (11 years).
• The model: attend diverse groups across geographies so ideas "have sex" and produce unexpected combinations.
• The "no time" objection fails — COO Alliance is 1.7% of a 40-hour work week; McKay Forums are 8 days out of 220.
• If you don't have time to join, that's precisely why you must: the business is running you.

Give first, take second

• Communities fail when everyone shows up to extract; they compound when members lead with generosity.
• The competitive advantage most leaders lack: genuinely asking "how can I help someone today?"
• The shift from "be the smartest person" to "know who the smart people are" (cf. Sullivan & Hardy, Who Not How).

Leading with human care

• At 1-800-GOT-JUNK, caring about employees' dreams, fears, and insecurities drove the company to rank #2 in Canada as a workplace.
• Exercise: have each person write one personal struggle on a Post-it, crumple and redistribute — everyone realises everyone is struggling.
• If leaders care about people more than their output, people will care about the business more than they otherwise would.

Three things that drove personal growth

1. Immersion in mastermind communities — the single biggest lever.
2. Deliberate work on soft skills: situational leadership, delegation, conflict management, communication.
3. Leadership and Self-Deception — reframing criticism as useful signal rather than threat.