Second in Command: The Chief Behind the Chief with Cameron Herold

Ever wonder what happens when the COO who scaled a company to $100 million realizes he was the problem?
In this episode, Cameron sits down with Mike Wood, COO of Jarrett Companies, who joined a $2 million Nashville construction firm and helped grow it into seven companies doing over $100 million.
They get into the machinery behind that growth: meetings from 6 to 9 a.m., five days a week, a double check on everybody in the building, and profit sharing that turns leaders into owners. Then it goes deeper. Mike opens up about learning to read at 25, the misery that followed his biggest turnaround, and the million-dollar flood where taking full ownership changed his entire team.
If the noise in your head is louder than the problems on your desk, this conversation is your way out. Listen now.

Sponsored by:
STS Capital – A global M&A advisory firm helping entrepreneurs achieve maximum value when selling their business, with a focus on strategic buyers and life-changing exits.
Learn more: https://stscapital.com

Timestamped Highlights
05:30 - Two million to one hundred million: why Mike had to keep replacing himself, over and over
07:38 - Meetings from 6 to 9 a.m., five days a week: the double check habit that ended repeat mistakes
13:16 - The six out of ten rule: why waiting two months on a problem employee costs you everything
15:51 - How to create safety before a hard conversation, so people can actually hear you
18:41 - The science of angry leadership: cortisol, the default mode network, and why exploding makes you dumber
23:26 - More money, happy family, great job, and the most miserable he had ever been: the fish tank moment
24:30 - Learning to read at 25: how a rare form of dyslexia wrote the negative script in Mike's head
30:28 - "This flood is my fault": the $1 million claim that became a masterclass in taking ownership
34:32 - What owners do when nobody is watching, and why every person in the building needs a double check
42:10 - Inside Learn to Love Being You: removing identities, forgiveness, and rewriting the stories that haunt us
About the Guest
Mike Wood is the COO of Jarrett Companies, a Nashville-based commercial construction group spanning site work, paving, concrete, fire protection, and mechanical services. Since joining as an estimator and project manager, he has helped grow the business from $2 million to more than $100 million in revenue across seven companies, including a fire protection company later sold to a private equity firm. Mike is also the founder of Learn to Love Being You, a 10-week program that helps people quiet anxiety and self-doubt through the same inner work that transformed his own leadership.

🔗 LinkedIn | Website

Mentioned Resources
Jason Jarrett, CEO of Jarrett Companies
Learn to Love Being You
Extreme Ownership by Jocko Willink and Leif Babin
The E-Myth Revisited by Michael Gerber
Smartsheet
1-800-GOT-JUNK?

Important Links
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World's Leading Community for Seconds in Command
Get Cameron's book: Second in Command: Unleash the Power of Your COO Book
Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi

The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

Sponsored by:
STS Capital – A global M&A advisory firm helping entrepreneurs achieve maximum value when selling their business, with a focus on strategic buyers and life-changing exits.
Learn more: https://stscapital.com

What if the smartest move you can make is to disrupt your own company before a competitor does?
In this episode, Lindsay Smith sits down with John Durocher, the self-described accidental COO of Calix. John never set out to run operations. He came up through consulting and customer success, never managed a supply chain or an IT org, and that is exactly why his CEO wanted him in the seat. His mandate: question everything.
John and Lindsay get into how to lead change when everyone is comfortable, build a leadership team that actually trusts each other, give feedback in the moment rather than at review season, and use AI to take drudgery off people rather than cut headcount. He also shares the directive that shaped his role: go build the company that would beat us.
For any second-in-command driving transformation without breaking their people, this is a playbook. Listen now.

This episode is brought to you by our Silver Sponsor, Next Level Growth.
They help COOs and leadership teams build Elite Organizations through a proven, customizable framework built around the Five Obsessions of Elite Organizations.
If you and your leadership team are ready to operate at the next level, take the Elite Organizations Assessment and receive a free 20-page customized report based on your answers, plus a complimentary one-hour coaching session with a Next Level Growth Partner and Business Guide to begin implementing tools that will help you build an even more elite business.
Complete the assessment here to get started - nextlevelgrowth.com/cooassessment

Timestamped Highlights
[00:01:32] The accidental COO: how a late-night phone call rewrote John’s career
[00:08:46] Why the people who succeeded longest have the hardest time changing
[00:10:05] Disrupt yourself, or wait to be disrupted... the directive that built his role
[00:10:59] When your CEO used to work for you: inside an unusually honest relationship
[00:16:11] Why John never waits for a formal review to give hard feedback
[00:18:22] The courageous conversation with his boss that became a breakthrough
[00:21:03] The team reset that exposes how little colleagues really know each other
[00:27:26] Seeing the seams: the bird’s eye view nobody else in the company has
[00:29:28] “Staple yourself to the order form” and other ways to fix the customer experience
[00:33:46] Fast isn’t always good... what moving too quickly does to an organization
[00:36:08] Stop telling your boss why it won’t work. Do this instead.
[00:37:25] The COO’s job is to slow down the CEO, not slam on the brakes
[00:42:43] Does remote work actually work? John’s rebuttal to the water-cooler myth
[00:46:41] What’s next for Calix: AI agents and the smart apartment

About the Guest
John Durocher is the Chief Operations Officer at Calix, where he leads operations across the company, from customer success and commercial operations to supply chain and IT. He joined Calix in 2023 as Chief Customer Officer and stepped into the COO role about a year ago. Before Calix, John spent 17 years at Salesforce leading customer success, where he watched the company grow from $250M to $30B in revenue. He began his career in consulting, including time at Accenture and Arthur Andersen, and describes himself as an accidental COO who treats the job like one long consulting project.
🔗 LinkedIn | Website
Mentioned Resources
Salesforce
Accenture
Michael Weening - President and CEO of Calix

About the Co-Host
Lindsay Smith is an experience-driven growth strategist and former Chief Strategy Officer who scaled a new region without a traditional sales team or bloated marketing budget by turning relationships, culture, and execution into revenue. She is the author of No One Needs Another Company Mug. Stop Branding. Start Experiencing and helps leadership teams use experience as a competitive growth lever.
🔗 Connect with Lindsay on LinkedIn
Important Links
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take Cameron’s leadership course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi

The Second in Command Podcast is an original production hosted by Cameron Herold and co-hosted by Lindsay Smith. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

This episode is brought to you by our Silver Sponsor, Next Level Growth.
They help COOs and leadership teams build Elite Organizations through a proven, customizable framework built around the Five Obsessions of Elite Organizations.
If you and your leadership team are ready to operate at the next level, take the Elite Organizations Assessment and receive a free 20-page customized report based on your answers, plus a complimentary one-hour coaching session with a Next Level Growth Partner and Business Guide to begin implementing tools that will help you build an even more elite business.
Complete the assessment here to get started - nextlevelgrowth.com/cooassessment

What is a COO actually for, and why do so many CEOs never figure it out?
In this solo episode, Cameron Herold tackles a question most CEOs never answer clearly: What is the point of a COO? Working through Chapter 2 of his book Second in Command, he makes the case that there is no single template. The right COO is the one who fits the CEO.
Cameron breaks down the traits that set strong seconds-in-command apart. Inward versus outward-facing roles. Translating between departments without being the expert. Finding shortcuts and building systems, the worst employee on the worst day can still run. He shares hard-won lessons from his years as COO of 1-800-GOT-JUNK, including the blowup that spread bad energy through the company for a month.
Get the fit wrong, and you get a swamped firefighter. Get it right, and you get real leverage. Listen now.
Timestamped Highlights
[00:36] – Why there’s no single template for a great COO, only fit
[02:16] – Inward or outward facing: which COO does your CEO actually need
[04:52] – The role a COO almost always plays, even when nobody sees them
[06:05] – Why being a chameleon beats being the smartest expert in the room
[08:29] – Empowerment over rescue: the parenting rule that reframes the job
[10:36] – The department feud Cameron refereed without taking over the work
[11:29] – The burned-out Starbucks sign that exposes a leadership question
[13:07] – The currency bet that saved $100,000 a year for every penny
[14:13] – The Buffalo snowstorm test for whether a system truly works
[15:20] – Strategy or tactics: the Sun Tzu line every COO should sit with
[19:07] – The blowup that spread bad energy through the company for a month
[19:50] – Why the best COO might be 27, not 57

Mentioned Resources
Free PR by Cameron Herold and Adrian Salamunovic
The E-Myth by Michael Gerber
Good to Great by Jim Collins
The Art of War by Sun Tzu
Shopify (Harley Finkelstein, Tobias Lütke)
1-800-GOT-JUNK and O2E Brands (Erik Church)
Apple (Steve Jobs)
Tesla (Elon Musk)
Ben & Jerry’s (Ben Cohen and Jerry Greenfield)
Starbucks (Greg Johnson)
Dell (Michael Dell)
Meta (Facebook) (Sheryl Sandberg)

Important Links
Connect with Cameron: Website | LinkedIn
Claim your FREE copy: Second in Command: Unleash the Power of Your COO Book
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command, Unleash the Power of Your COO Book
Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi

The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

What if walking away from the CEO seat was the smartest career move you could make in AI right now?
Cameron Herold sits down with Alex Triplett, COO of you.com, the company quietly powering web search for AI agents behind brands like Salesforce, Anthropic, and Harvey. Alex turned down the chance to be a CEO to take the second-in-command seat at a fast-moving AI startup, and he explains exactly why.
They get into the operator work most leaders avoid: walking into a 135-person company, making a brutal focus call, and rebuilding the team around a single mission. Alex breaks down his first 90 days, the listening tour that validated his biggest decision, how he sells to enterprise without getting strung along, and the system that keeps him out of the minutiae.
Skip this one, and you risk what most new executives do: the right idea at the wrong time, and broken trust. Listen now for the unfiltered COO playbook on focus and timing.

Sponsored by
Genius Network - An exclusive community for highly successful entrepreneurs, connecting you with top-tier leaders, strategic insights, and powerful relationships to help you grow your business faster and smarter.
Learn more: https://www.geniusnetwork.com/

Timestamped Highlights
10:16 – “Google for AI agents,” explained: the invisible layer your favorite LLM cannot work without
13:18 – You might be using you.com right now without knowing it. Here is where it hides in the AI stack
15:08 – How to tell a real enterprise deal from a buyer who is just keeping you busy
19:56 – The COO superpower hiding in plain sight, and why it gets you a seat at the C-suite table
23:08 – Chief of staff or glorified executive assistant? The title too many companies get wrong
25:24 – Three companies, one founder: how Richard runs you.com while raising $650M for a frontier lab
33:34 – 135 people on day one: the focus call that cut the team to 110, then built it back stronger
38:01 – One mission, one North Star, and the moment focus “just exploded” the company
39:23 – The first 90 days that make or break a COO: the listening tour that validated everything
47:23 – Why this COO leaves messages unread on purpose, and what it taught him about good decisions
50:09 – The one-sentence piece of advice he would give his 22-year-old self
About the Guest
Alex Triplett is the Chief Operating Officer of you.com, the leading web search API for AI agents, serving customers like Salesforce, Anthropic, and Harvey. An investor turned operator, Alex spent the first decade of his career in private equity before moving to the operating side. He served as Global Head of Corporate Development at ION Group, where he helped grow the business from $150 million to $3 billion in revenue, and later as CFO and COO of Appfire. He also chairs the board of the travel app Pangea and holds a degree from the McIntire School of Commerce at the University of Virginia.

🔗 LinkedIn | Website
Mentioned Resources
Pangea
Harvey
Salesforce (Agentforce)
Anthropic (Claude)
OpenAI
Google Gemini
Perplexity
xAI (Grok)
ServiceNow
Lovable
Replit
Genspark
AngelList
Shopify

Important Links
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi

The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.

Sponsored by
Genius Network - An exclusive community for highly successful entrepreneurs, connecting you with top-tier leaders, strategic insights, and powerful relationships to help you grow your business faster and smarter.
Learn more: https://www.geniusnetwork.com/

What if the most misunderstood role in business is also the one deciding whether your company scales?
In this solo episode, Cameron Herold, founder of the COO Alliance and author of Second in Command, tackles the question every growth-minded CEO eventually faces: what exactly is a COO? Drawing on Bennett and Miles’ research and his own years as second in command at 1-800-GOT-JUNK?, Cameron explains why no two COOs on the planet have the same job, and why the search for a great one starts with the CEO’s own strengths and gaps.
He walks through the seven types of COO: Executor, Change Agent, Mentor, Other Half, Partner, Heir Apparent, and MVP, with stories from Shopify, Oracle, Dell, and Facebook, plus the common roles a COO plays as adult in the room, integrator, and moderator.
Get this hire wrong, and the person meant to fix the chaos only adds to it. Listen now.
Timestamped Highlights
[00:00] – The question-asking habit that separates growing companies from stuck ones
[00:52] – Why most CMOs are interchangeable, but no two COOs share the same job
[01:40] – The only non-negotiable requirement for any COO
[02:31] – The research that uncovered the seven main categories of COO
[04:30] – When a change agent should come from outside the company
[05:34] – Why changing a company’s culture is like dealing with teenagers
[07:30] – The mentor move that shaped Facebook’s earliest years
[08:30] – The marriage test every CEO-COO pairing has to pass
[13:18] – The leadership meeting comment that earned Cameron the COO title
[18:57] – The homeowner and contractor rule for splitting the what from the how
[23:20] – Why the CEO, not the COO, should be the tiebreaker

Mentioned Resources
Riding Shotgun: The Role of the COO by Nate Bennett and Stephen A. Miles
Second in Command: The Misunderstood Role of the Chief Operating Officer by Nate Bennett and Stephen A. Miles (Harvard Business Review)
Double Double by Cameron Herold
High Growth Handbook by Elad Gil
Rocket Fuel by Gino Wickman and Mark C. Winters
Traction: Get a Grip on Your Business by Gino Wickman

Important Links
Connect with Cameron: Website | LinkedIn
Explore the COO Alliance - The World’s Leading Community for Seconds in Command
Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
Claim your FREE* copy: Second in Command: Unleash the Power of Your COO Book
Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
Chat or video call with AI Cameron via Delphi

*Valid only for CEOs or COO/Second in Command based in the US or Canada at companies wih $2M + revenue.
The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.