Between Two COO's with Michael Koenig

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(00:12) Advice for CEOs and COOs

This chapter welcomes Cameron Harold, the founder of COO Alliance and author of "The Second In Command," as we celebrate the release of his new book and examine its content, which serves as a guide for both CEOs and COOs. We explore Cameron's transition from COO to CEO, the mindset shifts that accompanied this change, and his insights into the balance between work and life. Cameron shares his experiences and lessons learned from running a business at a young age, including the importance of delegating, saying no, and focusing on the most critical tasks. The discussion also touches on how the book has already impacted the COO Alliance and the value it provides in understanding the CEO-COO dynamic.

(12:37) Promoting From Within vs. Hiring Externally

This chapter we explore the importance of creating a culture of continuous improvement within companies, akin to the mindset of elite athletes or performers. I share an anecdote about Patrick Roy to illustrate the resilience and determination that we aim to instill in our teams. We discuss strategies for fostering a safe environment where feedback is welcomed and viewed as a tool for growth, emphasizing that it's the systems, not individuals, that often need adjustment. We also touch on the sentimental value of sports heroes, as I recount a personal encounter with my childhood idol, Ken Dryden. Finally, I address the considerations involved in deciding whether to promote from within or hire externally for leadership roles, factoring in the individual's ability to complement the CEO's skills, their leadership qualities, and the strategic implications of such decisions, especially in companies with specialized knowledge or intellectual property.

(17:24) Flexibility in Organizational Structure With AI

This chapter examines the importance of flexibility in business operations and leadership. We explore the concept of a "bobbin' weave culture" where being too rigid can be detrimental, and the benefits of flowing like water, taking the path of least resistance towards the company's vivid vision. I discuss the necessity for leaders to align with core values and purposes, akin to a bobsled track, to guide the organization's journey. Additionally, we look at the challenges of introducing flexibility into rigid structures, using the example of Gerber Auto Collision's approach to acquisitions and the philosophy of "selling, not telling" to integrate new teams. The chapter also highlights the power of positive reinforcement and personal praise in leadership, drawing lessons from Howard Behar's practice of handwritten thank you notes at Starbucks, emphasizing the value of gratitude and recognition in driving employee success and satisfaction.

(24:55) Exploring AI Tools and Admired COOs

This chapter, we explore the significance of AI in the modern workplace, highlighting how our employees and CO Alliance members are encouraged to experiment with AI tools for one to two hours each week. We discuss the vast array of available AI applications, far beyond the widely mentioned ChatGPT, and the benefits of sharing experiences with these tools among teams to build momentum and enhance productivity. Examples include the transformative effects of AI on podcast production, such as using Descript to edit speech or Podium Stage for content creation. Additionally, we touch upon the importance of adaptability, illustrated by historical shifts in technology within NASA, and wrap up with admiration for influential COOs like Cheryl Sandberg and Matt Rawlings, noting how they exemplify effective leadership and innovation.

(30:39) Leadership Lessons and Insights

This chapter explores the contrasting leadership styles and trajectories of two COOs of 1-800-Got-Junk, with a focus on the impact of Eric Church's internal-facing, process- and people-centered approach as he grew the company from $70 million to $450 million, in stark contrast to my own media-facing, brand-building style during a different company growth phase. We also discuss the critical lesson of listening to team members, exemplified by a near-bankruptcy experience, and share a personal strategy for becoming a better listener by physically sitting on one's hands to encourage attentiveness. Finally, we examine the importance of asking systemic rather than symptomatic questions within leadership, illustrated by an anecdote involving Starbucks and the significance of maintaining operational systems for company-wide consistency.

(37:02) Catch Up and Discuss Book Promotion

This chapter celebrates the successful collaboration between CEOs...

Join us as Greg Strickland, COO of Productboard, and I explore the power of embracing new opportunities and the crucial balance between business outcomes and personal advancement. Greg shares his journey of growth through accepting challenges that push boundaries, and we reflect on the times when a strategic 'no' can pave the way for others' development and align with company goals. Listen in for an insightful discussion on the mentorship gap in early-stage companies and the trial-and-error learning that COOs like Greg navigate in the startup landscape.

As the startup ecosystem continues to evolve, we dissect the influence of continuous learning on company culture, inspired by industry pioneers. I open up about the enriching experience of partnering with product and engineering-driven founders and how passion plays a decisive role in a startup's trajectory. We consider how startups like Productboard are innovating in operations and product management with the use of AI, highlighting the agility required to manage rapid change and the ethical considerations of handling customer data.

In our conversation, we delve into the challenges of scaling up to the enterprise market and the importance of building a culture that can gracefully manage internal friction points. I share my approach to fostering empathy and collaboration across departments, revealing personal anecdotes and strategies for aligning diverse perspectives within a company. Tune in for a rich discussion full of practical insights, memorable moments, and tips for nurturing a successful startup environment. Follow Productboard on LinkedIn and check out their blog for more engaging content that can help steer your company towards growth and innovation.

(00:06) Saying Yes to New Opportunities

(08:14) Startups' Impact on Learning Culture

(17:25) AI for Operations and Product Management

(31:34) Navigating Enterprise Market Challenges and Feedback

(37:07) Friction and Empathy in Customer Relations

(45:25) Developing Empathy and Cross-Departmental Collaboration

Links

Greg Strickland on LinkedIn: https://www.linkedin.com/in/gregstrickland/

Episode Link: https://www.betweentwocoos.com/productboard-coo-greg-strickland

Matt Blumberg: https://startupceo.com/

The Hard Things About Hard Things by Ben Horowitz: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205

Amp It Up by Frank Slootman: https://www.amazon.com/Amp-Unlocking-Hypergrowth-Expectations-Intensity/dp/1119836115/

Radical Candor by Kim Scott: https://www.amazon.com/Radical-Candor-Revised-Kick-Ass-Humanity/dp/1250235375

Michael Koenig on LinkedIn: https://www.linkedin.com/in/michael-koenig514/

(05:11 - 05:38) Memory and the Evolving Digital Age

(06:56 - 08:05) Tech and Memory Retrieval

(11:40 - 12:51) Chat GPT and Data Privacy Integration

(17:34 - 18:44) Leveraging AI for Company Augmentation

(22:34 - 23:47) AI for Efficiency and Exceptional Hiring

(30:31 - 31:01) Pivoting to Capture Meeting Data

(38:38 - 39:00) COO and Chief of Staff Collaboration

(43:27 - 44:27) Using Cultural Values as a Guide

(47:10 - 48:20) Accountability and Candor in Successful Teams

(55:58 - 57:01) Impressions of AI Summarization

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(00:11) Augmenting Human Memory With AI

This chapter of Between Two COOs features a conversation with Dan Sroker, co-founder and CEO of Rewind, a personalized AI tool that augments human memory. Host Michael Kanag explores the inspiration behind Rewind and how it can give users a "superpower" by making all their digital interactions searchable and AI-able. They also discuss the importance of memory and how technology can enhance our natural capabilities. The conversation touches on the potential impact of relying on AI for memory recall and draws parallels to the evolution of phone numbers. Overall, this chapter explores the fascinating intersection of technology and human memory.

(12:51) The Future of AI in Operations

This chapter explores the potential impact of AI on future operations. Our guest, who has experience in scaling a company using AI, discusses how AI can be a powerful tool for leveraging human capabilities and increasing productivity. We also touch on the importance of privacy and security in AI, highlighting how companies that do not embrace it may struggle to compete in the future. The conversation concludes with a discussion on the role of AI in remote work and the potential for smaller teams to achieve more with the help of technology.

(18:44) Enhancing Productivity With Artificial Intelligence

This chapter explores the impact of AI on workplace productivity and efficiency. We discuss the release of GPT-4 and its potential to speed up tasks and increase productivity. Privacy challenges and the importance of employee awareness are also addressed. We examine how AI can bridge the gap between ambiguity and tasks, using Rewind's email summarization feature as an example. The significance of hiring exceptional senior staff and maintaining focus to achieve more with less is emphasized. Lastly, we touch on the potential impact of AI on the job market for recent graduates.

(27:19) The Impact of STEM on Technology

This chapter emphasizes the significance of STEM education in fostering creativity and problem-solving skills through technology. Our guest shares their personal journey with robotics, which led to the creation of innovative products like Optimize-A and Mac. The discussion also highlights the role of M1 and M2 chips in their company's pivot and how it enables local data privacy. Ultimately, we are reminded of the transformative potential of technology and the importance of adapting and maximizing its benefits.

(38:29) COOs and Chiefs of Staff

This chapter explores the dynamics of having a COO and chief of staff simultaneously, and how this partnership can benefit a company. We discuss the importance of screening for a good COO and chief of staff, as well as their role in creating a positive work environment. The former CEO shares his experience of achieving the number one spot for best place to work and the role of psychological safety in creating a fantastic workplace. Overall, this chapter provides valuable insights into the importance of a strong partnership between a CEO and their COO and chief of staff, and how it can contribute to the success of a company.

(42:23) Cultural Values in a Company

This chapter emphasizes the importance of defining and living up to company values. The host, who has experience at Google and now runs his own company, shares insights on creating a strong company culture by clearly defining values and behaviors that align with them. He highlights the need for these values to be a living document, constantly evolving and being used as a basis for performance management. The conversation also touches on the potential pitfalls of using values as a marketing tactic rather than a genuine reflection of the company's beliefs. Overall, this chapter highlights the role of company values in creating a positive and successful work environment.

(45:58) Psychological Safety in Leadership Importance

This chapter explores the importance of psychological safety in creating a successful and cohesive team. We discuss the guest's experience with psychological safety in their previous company and how they are implementing it in their current venture. We emphasize the need for a shared language and vernacular around psychological safety to create a sense of safety within a team. The guest also shares t...

(01:20 - 02:44) The Travel Experience Market's Growth

(04:36 - 06:03) Peer to Peer Tour Guide Platform

(07:27 - 09:26) Learning and Customer Obsession Importance

(12:35 - 13:56) Creativity and Execution in Strategy

(16:11 - 17:06) Identifying Core Values for Company Culture

(21:48 - 23:03) Accelerating Digitization and the QR Code

(36:32 - 37:43) Investment Strategy and Flywheel Approach

(39:48 - 40:47) International Tensions and Investment Impacts

(43:17 - 44:43) Applying AGI and AI to Operations

(00:11) The Travel Experience Industry Journey

This chapter welcomes Tao, COO of GetYourGuide, to share insights into the burgeoning travel experience industry. I explore how GetYourGuide, a company that started in a dorm room, grew into a $2 billion enterprise, selling over 80 million tickets to travelers seeking unique experiences, such as private tours of the Vatican Museum. We look at the travel experience market as an untapped online frontier, previously dominated by offline transactions and now worth $300 billion. Tao recounts the founding story of GetYourGuide, from its original concept as a peer-to-peer platform for tour guides to pivoting towards professional activity operators, marking the beginning of its success. We also touch upon the company's recent $194 million funding round and discuss the increasing trend of travelers preferring experiences over material possessions.

(13:56) Adapting Culture and Surviving Crisis

This chapter begins by exploring the integration of culture with changing strategies, emphasizing the importance of a consistent culture that supports shifts without causing disruption. I discuss the development of authentic core values by sharing a story of initial failure and eventual success through a reflective process with the leadership team, highlighting the key role of core values in determining who fits within a company. The conversation then pivots to the impact of COVID-19, recounting the immediate challenges and strategic decisions made in response to the pandemic, including the choice not to lay off staff and to continue investing in the future. The chapter concludes with an optimistic outlook, noting a strong recovery and promising prospects for the years following the initial crisis.

(21:10) Travel Industry

This chapter focuses on how businesses adapted during the pandemic, particularly addressing the balance between long-term planning and immediate operational needs. We touch on innovative measures like salary sacrifices for stock options and government-subsidized work hour reductions. We highlight the insights gained from having co-founders with molecular biology backgrounds, which helped us stay ahead in understanding the virus's impact on the travel industry. Additionally, we discuss the acceleration of digitization due to the pandemic, using the QR code's newfound ubiquity as a prime example. This digital shift significantly impacted operations, especially for our partnerships with historical attractions and museums, which had to quickly adapt to digital ticketing and queue management. Lastly, we examine the surge in travel as restrictions lifted, debunking the idea that the spike was merely 'revenge tourism' and noting the persistent trend towards domestic tourism.

(31:53) Board Members, Funding, Global Network Effects

This chapter focuses on the strategy behind assembling a board of directors for a private company, highlighting the importance of selecting members who bring expertise and accountability. We explore the company's recent Series F funding round, which includes a mix of cash and a revolving credit facility, designed to provide financial flexibility. The significance of raising funds during a period when many tech companies struggle is discussed, emphasizing the company's steady growth and prudent financial practices that have led to a successful up-round without resorting to complex financial instruments. I share insights into the deployment of the raised capital, underlining the company's investment into a technology-driven flywheel model, which encompasses building customer audience, enhancing the product, and acquiring a diverse inventory to support their mission of expansion, particularly in the U.S. market.

(40:48) Travel and AGI Building Connections

This chapter begins with reflections on the value of a connected world and the peace dividend concept, emphasizing how less military spending can boost investment in other sectors like technology and education. I examine the impact of decoupling on trade efficiency and express hope for the role of travel in fostering empathy and cultural understanding. I share insights on the potential of AGI and chat GPT to transform operations in various fields, including machine learning, translation, customer service, and personalized recommendations. I highlight the impressive capabilities of ...

Kettle COO, Nathaniel Manning, talks about balancing risk in a changing climate, structure without bureaucracy, evolution by design, good decision making, the social contract of insurance, and sitting on a monastery cushion for 3 months. He also talks about old guard vs new guard, building the plane while it's flying, making the implicit explicit, and evolution by design.

Nathaniel has a long career of founding and leading companies including Fellow Robots, BRCK, the largest provider of public wifi in Africa, and Ushahidi the world’s largest open-source platform for crisis response. Along the way, he worked on furthering clean energy as part of the Clinton Climate Initiative at the Clinton Foundation, and Nathaniel was part of the Obama Administration's first class of Presidential Innovation Fellow where he was special advisor on open data at USAID, the world's premier international development agency, where he went on to become the Chief Data Officer.

With that kind of track record, it’s safe to say that Nathaniel puts his money where his mouth is when it comes to creating technological solutions to some of the world’s biggest problems.

Nathaniel on LinkedIn: https://www.linkedin.com/in/nathanielmanning/

Kettle: https://ourkettle.com/

Episode Website: https://betweentwocoos.com/kettle-coo-nathaniel-manning

Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514