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

In today's episode of the Second in Command podcast, Cameron reveals a fresh approach to team building and annual planning that goes beyond stale meeting rooms and rigid agendas. You'll discover a game-changing strategy that combines the camaraderie of cooking, the serenity of nature, and the power of collaborative goal-setting. Learn how swapping hotel conference rooms for an Airbnb retreat can transform your leadership team’s dynamic, fostering deeper connections through shared experiences. You'll also find out how timing and intentional preparation can set your organization up for a strong year ahead.Through real-life success stories, actionable insights, and frameworks like EOS, this conversation dives into the importance of vivid vision, setting clear three-year goals, and crafting actionable one-year plans. From establishing quarterly accountability to aligning staffing and budgeting with long-term objectives, this episode equips leaders with practical steps to energize their teams and maximize results. Whether you're planning your next annual retreat or seeking innovative ways to strengthen your organization, this discussion is your roadmap to success.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!In This Episode You'll Learn:How simple activities like grocery shopping and cooking together can strengthen team bonds, create a family-like dynamic, and elevate your annual planning retreats. (1:04)Why hosting your planning sessions in an Airbnb instead of a hotel can foster creativity, relaxation, and stronger connections among team members, setting the stage for more effective collaboration. (2:58)The critical deadlines for locking in goals, budgets, and staffing plans to ensure a smooth transition into the new year. (5:06) How quarterly planning sessions can align your team’s priorities, leverage frameworks like EOS, and establish accountability with clear goals and review processes for every business area. (8:21)And much more...Resources:Connect with Cameron: Website | LinkedInGet Cameron’s latest book "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

Alicia Ramirez-Ingalls, Strategy and Operations Lead at Neat, shares her journey from a key role at Zoom to driving innovation in video communications. She dives into overcoming self-doubt and cultivating a 'fail fast' mindset, essential for learning and growth. Alicia emphasizes the importance of trust, open communication, and providing a safe space for experimentation in teams. With insights on enhancing productivity and embracing new challenges, she highlights how curiosity and structured processes can attract talent and foster collaborative environments.

In today's episode of the Second in Command podcast, Cameron is joined by Rob Follows, Chairman and Founder of STS Capital Partners.During the conversation, Rob and Cameron discuss the intricacies of selling businesses and navigating the complex world of mergers and acquisitions. They explore the challenges faced by entrepreneurs and business owners when it comes to maximizing the value of their companies and understanding the true impact of strategic advice.You'll discover the often-overlooked factors that can influence the final deal, including the role of private equity firms and traditional investment banks, and why these entities may not always align with the goals of family-owned or entrepreneurial businesses. Rob also emphasizes the importance of being strategic, cautious, and well-prepared throughout the process.From climbing the world’s tallest peaks to speaking about life planning and business value maximization, this episode provides both practical business advice and inspiring life lessons for entrepreneurs aiming for greatness.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:The importance of maximizing value when selling a business, especially for strategic buyers. How the 'Rembrandts in the attic' analogy explains the hidden value that strategic buyers see in a company.The challenges of working with smaller companies and the need for a certain level of business maturity.Common misconceptions about the mergers and acquisitions (M&A) process and the importance of aligning interests.The need for entrepreneurs to have a clear understanding of their required and preferred outcomes.And much more...Resources:Connect with Rob: Website | LinkedInConnect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of the Second in Command podcast, Cameron is joined by Alon Peleg, a seasoned Israeli leader and COO of aiOla, a cutting-edge conversational AI lab.During the conversation, Cameron and Alon explore the strategic decisions behind building a high-performance company culture and scaling effectively within a competitive industry. Alon shares insights on creating an environment that empowers employees to thrive while aligning with a larger vision, emphasizing the importance of hiring the right talent, especially in leadership and technical roles.You'll gain insights into navigating the complex and often lengthy process of selling to large enterprises. Alon highlights the key tactics for successfully penetrating these organizations, including understanding internal processes, building strong relationships, and focusing on continuous engagement. Hear about the importance of establishing champions within the customer base, ensuring that product evaluations are not taken lightly, and handling the delicate balance of pushing for growth while staying true to the company's focus.This episode offers advice about being bold, embracing risks, and continuously challenging oneself in both career and life, adding a final layer of inspiration to the broader themes of growth, resilience, and the pursuit of new horizons.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:Why the voice will be the main user interface in the future, as well as aiOla's ability to provide accurate and quick conversational capabilities.How aiOla's digital forms can replace paper-based processes, capturing data more efficiently and accurately.The value of understanding the customer's processes and the need for a champion within the customer organization to facilitate adoption.Alon's experience in hiring a new management team, including a CTO and a director of marketing, to scale the company.And much more...Resources:Connect with Alon: Website | LinkedInConnect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of the Second in Command podcast, Cameron discusses the intricate journey of transitioning from a hands-on business operator to a strategic owner. Discover the mindset and practical steps required for a CEO to step back from daily operations without losing the essence of their leadership. You'll learn the importance of clear communication, robust planning, and maintaining alignment within the team.Cameron offers actionable strategies for empowering a leadership team, including mentorship programs, setting up peer learning networks, and refining systems to inspect outcomes without micromanaging. He emphasizes the balance between delegation and abdication, ensuring the CEO retains strategic oversight while allowing the team to grow and succeed autonomously.Whether you’re a business leader looking to step back or an entrepreneur building sustainable systems, this episode provides a wealth of ideas to shape a thriving, self-reliant organization.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!In This Episode You'll Learn:How to prepare your team and organization for a long-term leadership transition, including leveraging strategic planning frameworks like EOS. (16:37)The importance of crafting a vivid vision to ensure continuity and alignment during and after a leadership shift. (19:02)Strategies to empower your leadership team through mentoring programs, peer learning networks, and structured support systems. (21:45)The difference between effective delegation and abdication, and how to inspect outcomes without micromanaging your team. (23:10)And much more...Resources:Connect with Cameron: Website | LinkedInGet Cameron’s latest book "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of The Second in Command podcast, Cameron is joined by Ryan Casey, Chief Operating Officer for The Lifestyle Investor.Ryan shares insights from an unexpected career journey that began in a surprising industry and led to expertise in sales, systems, and personal development. The conversation explores the power of structured approaches to relationship-building, professional growth, and leadership, highlighting how early experiences shaped a mindset focused on efficiency and strategic thinking.You'll learn about Ryan's pivotal career transitions, from managing multiple businesses to stepping into a leadership role within a rapidly growing organization. The conversation explores the challenges of scaling a founder-driven company, striking a balance between maintaining core values and building systems that allow for sustainable expansion.Whether you're an entrepreneur, a sales professional, or someone looking to optimize your approach to success, this episode is packed with thought-provoking lessons and actionable strategies.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:Ryan's experience with Orangetheory, including the challenges of marketing and generating leads during the COVID-19 pandemic. The benefits of having a founder-led company and the challenges of transitioning from a passion project to a business. The various asset classes the Lifestyle Investor covers, including private equity, credit funds, real estate, etc.Ryan's approach to marketing and learning, including joining coaching programs and masterminds to stay ahead of industry trends.And much more...Resources:Connect with Ryan: Website | LinkedInConversation with Griff Long, COO, Orangetheory FitnessConnect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of the Second in Command podcast, Cameron takes you on an exploration of a highly exclusive global network designed for those who are second-in-command within their organizations. The vision behind this community is clear: creating a space where professionals in leadership positions can connect, collaborate, and learn from one another. With monthly events, both virtual and in-person, members get the chance to engage deeply with peers across industries, share challenges and insights, and ultimately, enhance both their personal growth and business performance. You'll discover a dynamic environment where world-class content, real-world expertise, and a culture of accountability and support are at the forefront. Through various interactive formats, from member-led workshops to expert talks, this network fosters a unique atmosphere that encourages vulnerability, continuous learning, and strategic decision-making.This episode emphasizes the importance of developing a strong partnership between the COO and CEO, fostering trust, and ensuring a unified vision for the future.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!In This Episode You'll Learn:Why the arrival of a new COO is a significant event, with ripples affecting employees, suppliers, and the CEO's role. (1:20)The benefits of a well-executed onboarding process, building trust and understanding, and ensuring the COO can take over projects effectively. (8:20)Why COO coaching needs to focus on their strengths and areas for improvement, with CEOs coaching the areas where the COO shows skill. (17:23)The COO Alliance hosts monthly online events and two in-person events annually, including member presentations and deep discussions, with a focus on growth. (23:36)And much more...Resources:Connect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of The Second in Command podcast, co-host Sivana Brewer is joined by Ashley John Heather, Co-Founder, President, and COO of Lumati, a wellness firm that blends evidence-based science with natural solutions.During the conversation, Ashley shares a personal and professional journey marked by rapid growth, continuous adaptation, and a deep commitment to making an impact. As Lumati's work gains traction on a national level, he reflects on the challenges of scaling a mission-driven organization while balancing personal development.Beyond business, Sivana and Ashley explore the personal side of success—what it means to carve out space for reflection, mentorship, and a well-rounded life. Ashley acknowledges the relentless pace of building something new and the effort required to reach the next level.This episode offers some thoughts on the importance of awareness, whether in business, health, or personal growth, and how small decisions can have a lasting impact.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:The $4 trillion healthcare industry and why a growing number of people are seeking alternatives to traditional Western medicine.Ashley's transition into health after his brother's brain injury and his frustration with the healthcare system's focus on chronic conditions.The importance of conflict and disagreements as opportunities for better decision-making and growth.The difficulty of balancing the needs of existing team members with the need to bring in new talent.And much more...Resources:Connect with Ashley: Website | LinkedInConnect with Cameron: Website | LinkedInGet Cameron’s latest book – "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of the Second in Command podcast, Cameron explores a pivotal leadership decision that can transform the way businesses operate, grow, and scale. Every visionary leader reaches a point where their plate is too full, their time too stretched, and their focus divided. But the key to overcoming this challenge isn't just about delegation—it's about finding the right person to step in and elevate the entire organization. You'll discover a powerful framework that helps leaders assess their strengths, pinpoint their most valuable contributions, and identify the gaps that need to be filled to create a thriving, well-balanced team.  However, bringing in the right support isn't as simple as hiring another executive. It requires deep self-awareness, a clear understanding of what drives energy and productivity, and a willingness to relinquish control in areas that may not align with a leader’s true strengths. Cameron reveals a proven system for breaking down tasks, uncovering unique abilities, and strategically redistributing responsibilities to unlock greater efficiency and momentum.This episode shows why having a trusted partner in the business—someone who balances vision with execution and provides both challenge and support—can be a game-changer.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!In This Episode You'll Learn:The importance of self-reflection for CEOs to understand their skills and needs before hiring a COO. Insights from Jim Morrisroe, CEO of 15Five, on the importance of having a reliable and supportive COO. Why a COO should be the CEO's built-in support network, handling disruptions and providing stability. Why finding the right COO can amplify and ignite the CEO's potential, leading to rapid growth and productivity.And much more...Resources:Connect with Cameron: Website | LinkedInGet Cameron’s latest book "Second in Command: Unleash the Power of Your COO"Get Cameron’s online course – Invest In Your Leaders

In today's episode of The Second in Command podcast, Cameron is joined by Alex Dogliotti, Ph.D, Chief Human Resources Officer and Chief Operations Officer for Mindvalley.During the conversation, Alex shares insights into a groundbreaking shift reshaping the way organizations operate. He discusses how a passion-driven initiative within the company led to a powerful internal transformation, fundamentally altering workflows and redefining traditional roles.You'll hear about the challenges and opportunities that come with stepping into a leadership role during a time of significant transition. Alex reflects on the delicate balance of honoring past decisions while driving forward change, emphasizing the importance of assembling the right team.This episode serves as a testament to the power of trust, adaptability, and saying “yes” to challenges that lead to unexpected and rewarding paths.If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:Mindvalley's transition from an educational platform to an AI-driven data company focused on personal transformation.The role of WhatsApp in company communications and the need for strategies to manage information overload.The importance of financial and product roadmaps in making decisions. Mindvalley's approach to AI training, including partnerships with LinkedIn Learning and AI authors.And much more...Resources:Connect with Alex: Website | LinkedInConnect with Cameron: Website | LinkedInGet Cameron’s latest book "Second in Command: Unleash the Power of your COO"Get Cameron’s online course – Invest In Your Leaders