In this Fan Favorite episode of the Second in Command Podcast, Cameron Herold speaks with Anna Collins, President and COO of Bulletproof, the globally recognized brand behind Bulletproof Coffee, supplements, and biohacking products designed to help people perform better, think faster, and live healthier lives. She is also a Board Member of Ladies Who Launch.

Before joining Bulletproof, Anna led multi-billion-dollar businesses at Amazon, Microsoft, and CVS Health, bringing a data-driven, operational mindset to every stage of growth. In this conversation, she reveals how she helped Bulletproof evolve from a niche “biohacker” brand into a household name—streamlining operations, tightening focus, and scaling omnichannel distribution without losing its visionary edge.

Anna also shares her leadership principles, from managing a founder with 100 ideas a day to running metrics-driven weekly business reviews that keep innovation grounded in reality. Her insights bridge the gap between entrepreneurial chaos and corporate discipline, showing how great COOs turn vision into execution.

[00:00:00] – Cameron introduces this episode as one of the most downloaded in show history.

[00:01:14] – Anna’s career journey: from Microsoft and Amazon to joining Bulletproof.

[00:03:52] – Why she left Amazon Prime for a mission-driven brand.

[00:05:36] – What convinced her Bulletproof wasn’t just a fad—but a real performance enhancer.

[00:06:23] – Partnering with Dave Asprey: defining roles between visionary and operator.

[00:07:18] – The challenge of narrowing focus when everything looks like a good idea.

[00:08:54] – Bringing Amazon’s frameworks—tenets, principles, and data mechanisms—into Bulletproof.

[00:10:07] – How structure helped Dave trust the team and delegate.

[00:10:26] – Shutting down international markets and cutting SKUs to simplify growth.

[00:11:59] – Expanding into Amazon marketplace and corporate distribution channels.

[00:13:28] – Convincing the founder to “grow beyond the core biohacker.”

[00:17:00] – Managing an idea-rich founder without stifling creativity.

[00:18:37] – Anna’s leadership philosophy: define reality, create possibility, say thank you.

[00:21:00] – Rebuilding Bulletproof’s vision, mission, and values for clarity and culture.

[00:24:20] – Weekly Business Reviews: the data-driven rhythm behind execution.

[00:30:32] – How Anna divides her focus across key stakeholders—customers, team, and growth.

[00:36:35] – Simplifying the Bulletproof brand for mainstream accessibility.

[00:38:00] – Where she struggles as a leader—and the balance between speed and empathy.

[00:42:33] – The advice she’d give her 21-year-old self: don’t take it all so seriously.

About the Guest

Anna Collins is the President and COO of Bulletproof overseeing strategy, operations, and omnichannel growth for the globally recognized biohacking brand. Previously, she led billion-dollar initiatives at Amazon, where she managed global Prime membership programs, and at Microsoft, where she built the search advertising business from concept to $1.6B in revenue. She is also a Board Member of Ladies Who Launch.

A Harvard MBA and transformational leader, Anna specializes in building scalable systems that bridge creative vision with operational discipline. At Bulletproof, she’s helped expand the company from its core biohacker audience to a broader wellness market—making human optimization accessible to everyone.

🔗 LinkedIn

• Bulletproof

In this episode of the Second in Command Podcast, guest host Sivana Brewer sits down with Daniel Quinonez, Chief Operating Officer of the Plumbing-Heating-Cooling Contractors Association (PHCC) — one of the oldest trade associations in the United States, founded nearly 140 years ago.

Daniel shares how this long-standing organization is transforming to meet the modern era while honoring its heritage. From training apprentices who go on to run multimillion-dollar companies, to integrating AI and new tech tools into the trades, the PHCC is proving that innovation and tradition can coexist.

He also opens up about leadership lessons from his own journey, from mopping floors at his father’s bar to leading a national $30M organization, and how his personal mantra, “Be nice,” has shaped his management style, his culture, and his success.

If you lead a legacy business, manage a growing team, or want to understand how blue-collar industries are embracing technology, this episode offers both inspiration and strategy.

[00:01:00] – The PHCC’s 140-year history and why plumbing is a pillar of public health.

[00:02:40] – How the industry came together to standardize clean water systems in the 1920s.

[00:03:44] – What PHCC offers its members today: education, licensing, and community.

[00:05:08] – From one truck to $10M: stories of self-made contractors in the trades.

[00:06:14] – Why nearly every successful owner started as a hands-on apprentice.

[00:08:00] – How AI is transforming the trades and why it’s an ally, not a threat.

[00:09:34] – Changing perceptions: convincing parents that the trades are a smart career path.

[00:10:39] – The rise of entrepreneurship and financial freedom in plumbing and HVAC.

[00:11:42] – Daniel’s own career path from government and lobbying to COO.

[00:13:57] – Becoming the first COO in PHCC’s 140-year history.

[00:15:25] – Helping a century-old organization modernize its operations and systems.

[00:17:03] – Growing membership and education as PHCC’s two strategic pillars.

[00:18:55] – The PHCC Online Academy: 15,000 students and counting.

[00:21:00] – The challenge of evolving legacy culture and systems in long-standing institutions.

[00:22:30] – Why more contractors are creating COO roles for succession planning.

[00:25:17] – Family businesses, private equity, and the changing face of ownership.

[00:27:56] – Daniel’s leadership mantra: “Be nice.”

[00:33:38] – Balancing kindness with accountability and setting measurable goals.

[00:35:00] – Building buy-in and bringing staff along during organizational change.

[00:39:00] – Teaching business finance and leadership to new COOs in the trades.

[00:43:36] – Daniel’s excitement for PHCC Connect 2024 and the next generation of apprentices.

• PHCC – Plumbing-Heating-Cooling Contractors Association
• PHCC Academy – Online education and apprenticeship training
• Quality Service Contractors (PHCC Program) – Business coaching for contractors
• Federated Insurance – PHCC partner for business succession planning
• SkillsUSA & WorldSkills Competitions – Annual events supporting young tradespeople

Daniel Quinonez is...

In this powerful episode of the Second in Command Podcast, co-host Sivana Brewer sits down with Brittany Dunn, COO and co-founder of Safe House Project, a national nonprofit dedicated to eradicating human trafficking in the United States.

Brittany shares the remarkable story of how she and her co-founder built Safe House Project from an idea into a nationwide movement, launching a full organization in just 90 days while balancing motherhood, military life, and a mission to save lives.

She discusses how her background in international business and M&A shaped her operational mindset, and how she’s using corporate systems to solve one of the world’s most complex humanitarian challenges. From developing Simply Report, a tech platform helping identify trafficking cases, to fostering a trauma-informed team culture, Brittany offers a masterclass in leadership under pressure, emotional resilience, and purpose-driven innovation.

[00:01:00] – Brittany shares the mission behind Safe House Project and how it began.

[00:02:15] – Only 100 safe house beds existed for 300,000 trafficked kids—why resources were so scarce.

[00:04:26] – How two military spouses built a national nonprofit in 90 days.

[00:06:01] – Why they launched nationally instead of locally (and how it changed everything).

[00:08:00] – A day in the life: policy, survivor support, sting operations, and leadership.

[00:10:20] – The corporate skills that transferred and the ones that didn’t.

[00:12:17] – Balancing strategy with empathy: why people aren’t “projects.”

[00:13:01] – Hiring survivors to co-create programs that work in real life.

[00:15:27] – The emotional weight of leading in trauma-informed work.

[00:17:14] – Launching Simply Report, a new tech platform for anonymous trafficking tips.

[00:19:00] – The behavioral algorithm behind Simply Report and how it works.

[00:21:17] – The power of partnerships and why Brittany took every call early on.

[00:22:41] – Preventing burnout: clarity, communication, and individualized care.

[00:25:37] – Inside her relationship with her co-founder and how they model healthy conflict.

[00:29:23] – Building a culture of trust, ownership, and open dialogue (“Cuss and Discuss”).

[00:34:05] – How Safe House Project hires intentionally and why cultural fit matters most.

[00:36:10] – The art of letting go: why firing fast protects mission and morale.

[00:37:30] – A recent setback and how the team turned disappointment into innovation.

[00:40:18] – Choosing integrity over comfort: giving back salaries during COVID to keep promises.

[00:42:01] – Daily rhythms that keep Brittany grounded in hard seasons.

[00:43:23] – The next big challenge: state-level adoption of Simply Report.

[00:44:13] – A hopeful look ahead: documentary, podcast, and shifting public awareness.

• Safe House Project
• Simply Report App (iOS & Android) – Anonymous reporting tool for human...

In this episode of the Second in Command Podcast, co-host Sivana Brewer chats with Will Smith, COO and Managing Partner of Lone Star Pups, a multi-location Dogtopia franchise with 15 stores across San Antonio and Denver.

Will shares how he’s scaled his team from zero to 140 employees in just a few years by leading with servant leadership, radical transparency, and a simple but powerful formula: Time + Trust = Influence.

From teaching his staff about personal finance to running anonymous team surveys and writing heartfelt newsletters himself, Will breaks down how he creates a workplace where people feel seen, supported, and connected to the company’s mission. He also dives into financial literacy and why understanding money, personally and professionally, is the missing link for many leaders.

Whether you’re managing a large service team or growing a people-first brand, this episode is packed with actionable leadership and financial principles that can transform both your team and your bottom line.

[00:04:15] – How Lone Star Pups began as a post-COVID passion project.

[00:05:47] – The story behind Will’s partnership with his CEO, Devin.

[00:07:43] – Building trust by adding value—not ego—to leadership.

[00:09:19] – Why Will left a 30-year hospitality career to run a dog business.

[00:11:00] – Making decisions that impact 140 people every day.

[00:12:00] – Servant leadership in action: clearing plates, fixing walls, setting culture.

[00:13:34] – How Time + Trust = Influence became the company’s core formula.

[00:16:10] – What Will learned from his first company-wide employee survey.

[00:17:00] – How monthly newsletters create connection and clarity.

[00:19:10] – The truth about communication—why “no one ever over-communicated.”

[00:25:20] – The meaning behind Watering Your Bamboo and why patience drives growth.

[00:27:26] – How Will learned financial discipline from his grandfather.

[00:29:00] – Teaching personal finance to staff—and why it improves retention.

[00:31:36] – “Canary Metrics”: a system to track the financial health of each location.

[00:33:49] – Why every manager must learn to write their own P&L variances.

[00:35:00] – The link between personal spending habits and leadership performance.

[00:40:35] – Helping the next generation reclaim their time, focus, and financial control.

[00:41:15] – What’s next: growth, teaching, and giving back.

• Lone Star Pups, LLC
• Dogtopia
• Watering Your Bamboo by Greg Bell
• The 80-10-10 Rule – Will’s personal finance framework (80% bills, 10% savings, 10% giving)
• The Speed of Trust by Stephen M.R. Covey

In this episode of the Second in Command Podcast, Cameron Herold sits down with Ebert Grobler, COO and co-founder of Ruby Digital, one of South Africa’s top-ranked digital agencies now expanding across the globe.

Ebert, who is a COO Alliance member, shares how his company has achieved near-perfect team retention and why their internal mantra—“Grow People, Grow Global, Grow Profit”—has fueled both performance and culture. From developing a system called The Ruby Way to empowering every team member to operate like an entrepreneur, Ebert breaks down how Ruby Digital builds sustainable high performance without burnout.

He also explains how they’ve turned retention, trust, and human connection into a competitive advantage in a saturated market and why premium service is still one of the rarest differentiators in the U.S. marketing landscape.

[00:01:45] – Why Ruby Digital is expanding from South Africa into the U.S.

[00:05:25] – The surprising gap in the U.S. market: quality and retention.

[00:08:12] – How Ruby Digital achieves 95–100% staff retention.

[00:10:20] – Creating “The Ruby Way”: an operating system built on trust.

[00:12:45] – Letting employees act like entrepreneurs without the risk.

[00:16:00] – “Step Up”: the six-month advancement model that keeps people growing.

[00:18:30] – Guardrails against burnout: scorecards, balance wheels, and wellbeing KPIs.

[00:22:40] – Why culture drives premium client delivery.

[00:25:05] – How Ebert measures success: Grow People → Grow Global → Grow Profit.

[00:27:15] – Ruby’s philosophy: manage risk, not just marketing.

[00:30:10] – B2B growth: focusing on long-term relationships, not quick wins.

[00:33:25] – The “SMC client” model—serving sophisticated, mature companies.

[00:36:10] – How much companies should invest in marketing (and why most don’t).

[00:41:10] – Ruby’s 15% marketing reinvestment and in-house client mindset.

[00:45:30] – Turning unused leads into referral revenue.

[00:48:10] – The biggest lesson from failure: trust is earned, not given.

• Smart Marketing 2.0 Podcast – Co-hosted by Ebert Grobler
• Scaling Up by Verne Harnish
• Good to Great by Jim Collins

Ebert Grobler is the COO and co-founder of Ruby Digital, a global performance marketing agency headquartered in South Africa with hubs in the U.K. and U.S. A former communication-science student turned “human-systems engineer,” Ebert is known for creating organizational models that blend business growth with human sustainability. Under his leadership, Ruby Digital has been recognized as one of the Top 20 Companies to Work For in South Africa by the U.K. Sunday Times and continues to redefine what it means to run a people-first, performance-driven company.

🔗 LinkedIn |

In this episode of the Second in Command Podcast, guest co-host Sivana Brewer (Fractional COO for Remote Teams and former COO at Closers.io) sits down with Cory Raggi, COO of 1RDG The Financial Center, to talk about leading with empathy, navigating change, and building trust in teams both large and small.

Cory shares her journey from leading HR at a 15,000-person company to stepping into her first COO role at a fast-growing 80-person firm. She opens up about how she learned to adapt, communicate, and stay grounded in high-pressure situations and the three core practices that help her regulate stress and lead with clarity.

From learning to “roll on the edge” between people and performance to replacing stress with self-awareness, this conversation is packed with real-world leadership lessons for operators who want to grow without burning out.

[00:02:00] – How Cory went from HR leader to unexpected COO.

[00:03:00] – Redefining what a COO really does (and doesn’t do).

[00:06:26] – “Right people, right seats”: her mantra for solving every problem.

[00:08:12] – Building trust with the CEO and learning to push back.

[00:10:21] – Deprogramming corporate habits in a smaller company.

[00:13:07] – Leading teams without being the technical expert.

[00:17:13] – Building fast trust through humility and honest communication.

[00:19:25] – The mirror test: checking your own leadership energy first.

[00:22:00] – Balancing people and business why great leaders “roll on the rim.”

[00:23:40] – Running effective meetings that actually serve their purpose.

[00:28:16] – Leadership breakdowns most middle managers make.

[00:33:13] – How Cory learned to stay calm and centered under pressure.

[00:36:49] – The one-next-right-thing method for managing stress.

[00:42:00] – The isolation of being a COO—and how to find your support system.

[00:47:16] – What’s next for Cory personally and professionally?

Cory Raggi, SHRM-SCP is the Chief Operating Officer of 1RDG The Financial Center, a company providing integrated accounting, payroll, benefits, and wealth management solutions for business owners. With a background in HR and organizational leadership, Cory blends people-first management with operational structure, helping teams stay aligned, communicative, and focused through growth.

🔗 LinkedIn | Website | Podcast | Linktree

• The Speed of Trust by Stephen M.R. Covey
• Crucial Conversations by Patterson, Grenny, McMillan & Switzler
• Meetings Suck by Cameron Herold
• Emotional...

In this Fan Favorite episode of the Second in Command Podcast, Cameron Herold sits down with Sarah Jones Simmer, former COO of Bumble, to explore how the company scaled from an empowering dating app into a billion-dollar global social platform redefining connection and kindness online.

Sarah shares her journey from investment management to leading one of the fastest-growing social networking brands in the world. She opens up about working alongside visionary founder Whitney Wolfe Herd, expanding into markets like India, building culture-first teams, and reimagining leadership through empathy and purpose.

From balancing motherhood and executive leadership to driving global expansion and shaping company culture, Sarah’s story offers an inspiring look at what it means to lead with both strength and softness.

About the Guest

Sarah Jones Simmer is a seasoned business leader and former Chief Operating Officer of Bumble, where she helped scale the brand to over 50 million users worldwide. With a background in investment and strategy consulting, Sarah has built her career around mission-driven leadership, global expansion, and empowering women in business.

🔗 LinkedIn | Website

• Serena Williams x Bumble Super Bowl Campaign
• Adam Grant – Organizational Psychologist and Author
• Kolbe Profile (KOLBE A)
• TEDWomen Conference

• 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

Note: This Fan Favorite episode is a recast of one of our most impactful interviews, still packed with insights for second-in-command leaders. Whether it’s your first listen or a revisit, there’s timeless value inside.

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.

In this episode of the Second in Command Podcast, Cameron Herold speaks with Brent Hagan, Chief Supply Chain Officer at Lob, a direct mail automation platform delivering billions of personalized mail pieces every year.

Brent shares how he helped a 12-year-old startup kick off its “second act” by transforming complex logistics into scalable systems powered by technology and disciplined leadership. He opens up about developing next-generation leaders, learning to balance autonomy with accountability, and why the best operators focus less on “doing” and more on developing people who can think for themselves.

From saying yes to opportunity to mastering feedback and context-switching, Brent breaks down how to lead through clarity, consistency, and reflection - and why great COOs act as both a shock absorber and a multiplier for the entire organization.

• Lob
• USPS (United States Postal Service)
• Amazon Discover Insights Program
• Wharton Executive Education
• Purdue University
• Invest In Your Leaders Online Course
• 
  

Brent Hagan is the Chief Supply Chain Officer at Lob, overseeing logistics, vendor partnerships, and operational excellence for one of the fastest-growing direct mail automation companies in the U.S. A former Amazon leader and Wharton executive education graduate, Brent specializes in scaling operational systems, building resilient teams, and turning feedback into a strategic advantage.

🔗 LinkedIn | Website

• 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