Max de Groen is a managing director at Bain Capital Private Equity (one of the world's leading PE firms with over $130 billion of assets under management), where he focuses on investments in infrastructure, cybersecurity, and application software as well as internet and digital media. This means is is well positioned to help us understand more about the future of technology enabled businesses.  Max joined Bain Capital Private Equity  in 2010. Prior to joining Bain Capital Private Equity, Max was at The Boston Consulting Group, where he consulted in the technology, financial services, and healthcare practice areas. He also serves on the board of directors of Nutanix, and Rocket Software and has also previously been involved in Bain Capital’s investments in BMC Software, Symantec, and NortonLifeLock among others. Our discussion dives into Max's views on: Due Diligence and Technology Debt (and how to evaluate it prior to an investment) Where we are in the trend towards cloud computing (in many ways the trend has just begun) The reason Bain Capital invested in Nutanix and the future of hyper converged infrastructure and hybrid cloud Hot technology sectors Bain Capital is considering investments in What sets Bain Capital apart from other investment sources (the pioneered a concept called  value-added investment, they partner with management teams to help build and grow great firms) Lessons learned from investing in firms like Symantec Related Resources: Bain Capital PE A CTO’s Perspective on Technology Debt in M&A

Security, Risk Management and Intelligence professionals all know of Jim Clapper. He had a long and distinguished career in the US Air Force, which included leadership spanning the Vietnam era all the way to the end of the Cold War. By the time he retired he was a three star General, leading the Director of the Defense Intelligence Agency. After retirement he would later return to government service as head of the National Imagery and Mapping Agency just three days after 9/11. In 2007 he was named the Pentagon’s top intelligence official (USDI), serving as an appointee in both the Bush and Obama administrations before President Obama appointed him DNI.  He is author of the book “Facts and Fears: Hard truths from a life in intelligence.” In this OODAcast we sought to extract lessons from General Clapper's career relevant to intelligence professionals in and out of government. We get behind the scenes looks at the sometimes frustrating situations he was placed in early in his career and lessons that flowed from frustrations, including anecdotes that drive home the reality of what intelligence is supposed to be. Intelligence professionals in and out of government will hear first hand the dangerous temptations put on intelligence professionals to do what is easy and why the easy path can lead to irrelevance. Ever heard of a "self-licking ice cream cone?" We explore the caution of that phrase, which is a warning to not just produce intelligence for intelligence sake. Intelligence must be produced for a purpose and disseminated to those who need it. We also examine the tendency of some in the intelligence community to want to be historians, focused on exploring what happened instead of what will happen next. Reputation of military intelligence cultures are also examined. We examine cyber intelligence, and the perception of some that the intelligence community is falling into the trap of just being historians there. But we also dive into what can be done to change this situation including changes in legislation and funding and prioritization. Whether you are in commercial business intelligence or the government intelligence community there are lessons for you from the successful Osama Bin Laden raid of 2 May 2011 and we examine some of them in this OODAcast. If you are in the commercial sector and do not run your own operational military units you may be wondering what these lessons are. As you will find in the video, the success was based on being proactive about intelligence. Making assessments, seeking information, validating or refuting hypotheses, making new assessments and continually hunting for the right data. This success focused approach is required in any successful intelligence effort. We ask for insights and tips on how to provide intelligence to incredibly busy decision makers. Cut away the fluff, he says, know what two or three points to make, make them, and stop. This can be hard, it is almost always easiest to drone on. But investing in making points succinctly and clearly are key. General Clapper's management and leadership style reflects a belief that people should be treated with respect, and in most professional situations you should assume you are interacting with people that are competent and are set on doing the right thing, unless you get information that indicates otherwise. This approach comes with some risks but has helped bring out the best in teams he has led. We talk about this and many other leadership lessons including an example where his mother demonstrated to him an enduring lesson about bravery and an ability to take action at the moment needed to do the right thing. This happened in 1952 at Chitose Air Force base in Japan, and young Jim Clapper was at the Officer's club with his parents. Watching how his mother proactively worked to demonstrate that all races are welcome at her table left a mark on him he explains well in this discussion. This story is the kind of thing they make movies about, and is well worth hearing and reflecting on today. We also talk about operational intelligence, and get an excellent briefing from General Clapper on the dynamics in the geopolitical situation with China and Russia. Additional Resources in and references on Intelligence: A Practitioner’s View of Corporate Intelligence: Organizations in competitive environments should continually look for ways to gain advantage over their competitors. The ability of a business to learn and translate that learning into action, at speeds faster than others, is one of the most important competitive advantages you can have. This fact of business life is why the model of success in Air to Air combat articulated by former Air Force fighter pilot John Boyd, the Observe – Orient – Decide – Act (OODA) decision loop, is so relevant in business decision-making today. Useful Standards For Corporate Intelligence: Discusses standards in intelligence, a topic that can improve the quality of all corporate intelligence efforts and do so while reducing ambiguity in the information used to drive decisions and enhancing the ability of corporations to defend their most critical information. Optimizing Corporate Intelligence: Actionable recommendation on ways to optimize a corporate intelligence effort. It is based on a career serving large scale analytical efforts in the US Intelligence Community and in applying principles of intelligence in corporate America. An Executive’s Guide To Cognitive Bias in Decision Making: Cognitive Bias and the errors in judgement they produce are seen in every aspect of human decision-making, including in the business world. Companies that have a better understanding of these cognitive biases can optimize decision making at all levels of the organization, leading to better performance in the market. Companies that ignore the impact these biases have on corporate decision-making put themselves at unnecessary risk. Global Risks and Geopolitical Sensemaking: A collection of critical resources for any organization seeking to track, and mitigate risks due to international geopolitics events and actions.

R “Ray” Wang is the Founder, Chairman and Principal Analyst of Silicon Valley based Constellation Research Inc., a research and advisory firm which studies disruptive business and exponential technology trends. You very likely have heard of Ray before. He is active on social media (follow him here). He is also frequently interviewed in media outlets such as the Wall Street Journal, Fox Business News, CNBC, Yahoo Finance, Cheddar, CGTN, Tech Crunch, ZDNet, Forbes, and Fortune. Ray is the co-host and co-founder of the widely watched DisrupTV, a weekly enterprise tech and leadership webcast that averages 50,000 views per episode. He’s also the author of the popular business strategy and technology blog “A Software Insider’s Point of View”. Since 2005, Ray has delivered hundreds of live and virtual keynotes around the world that are inspiring and legendary. Wang has spoken at almost every major tech related conference, including Salesforce’s Dreamforce, Adobe Summit, IBM Think, HR Tech Conference, Microsoft’s Conferences, Google Next, and the sessions at Davos for various clients. Ray is a great leader, evidenced by the people he has attracted to his firm. I know many of his team and can say for a fact that they are people who can do just about anything they want (which means they are in a position to pick their boss). Ray is also an entrepreneur, and in this OODAcast provides context anyone thinking of starting out on their own should consider. One of many anecdotes he provided was an insightful recap of a conversation he had with his then boss at Forrester Research, George Forrester Colony, which made it clear to Ray that he faced a choice. He could work at a place that wanted to motivate him to be as average as possible or he could go out on his own and create his future himself. Ray is one of the most prolific writers and thinkers in this space, which includes bestselling books. His 2015 "Disrupting Digital Business" provided insights into ways businesses could create authentic, trustable experiences for clients and optimal experiences for employees in an age where the economy focuses less on products and services and more on experiences and outcomes. We also ask Ray for early context on his latest book, "Everybody Wants to Rule The World", which brings new lessons on surviving and thriving in a world of digital giants like Amazon, Google and Facebook. The book may help you steer your business to success in an age where many will be crushed by the powerful forces unleashed by large firms like these. Why read this book? Because if you don't, you may well be crushed. Imagine the incredibly tech savvy Dominos Pizza, who really should be lauded for their embracing new technologies and disrupting the pizza business through technology. But now are in total danger of being crushed by an amazing, but previously unforseen model, which enables firms by companies that don't have stores, that don't sell pizzas, and don't have their own drivers, but that can deliver. The food aggregators, like postmates , Doordash etc, don't have to invest the capital to make pizza in order to make money from the transaction. This is just one of many examples, Ray also tells us how to crush LG and Samsung, for example, using the new approaches to platform based dynamics. We ask Ray for his insights on many other tech topics, including quantum computing, quantum security (he says it is like running a bulldozer over a thatch hut), Bitcoin and Cryptocurrencies. Additional Resources: Constellation Research Ray Wang on LinkedIn Everybody Wants to Rule The World Disrupting Digital Business  

Lisa J. Porter has successfully lead some of the world's largest and most critical technology efforts. Her career started with a focus on academic rigor in pursuit of some of the toughest degrees, a B.S. in Nuclear Engineering from MIT and a PhD in Applied Physics from Stanford. She would later lecture at MIT and then became a researcher for DARPA related projects, eventually becoming a DARPA program manager. Dr. Porter would later lead NASA's Aeronautics Portfolio, would become the first Director of the Intelligence Community's IARPA, became President at Teledyne Scientific and an EVP at In-Q-Tel, and then was named to be the Deputy Under Secretary of Defense for Research and Engineering, an office which is essentially the CTO for the entire Department of Defense. She now co-leads a consultancy she formed with Michael Griffin (LogiQ).  In this OODAcast we explore Lisa's approach to leadership in the technology domain. Some themes from the discussion: Her comments throughout point to an ability to focus and decide what she would pursue with a determination to accomplish her goals. For example, early on she had a determination to dig into topics associated with solutions around future energy needs and pursued her undergraduate in nuclear engineering. She later acted on a determination to support national security. Like many others she faced a changing moment when the attacks of 9/11 happened. We review how Tony Tether looked her in the eye and convinced her to make the right choice and knew it was time to change. Through her career she was continually placed in situations where she needed to adapt and overcome and in every case rose to the occasion. She recounted several situations in her early career where she learned from role models, including previous generations of great technology leaders like George Heilmeier (famous for Heilmeier's Rules, which are pasted below), and Tony Tether. We discussed how some technologists are fantastic individual contributors but are not so good at leadership, and learn lessons on how we can all get better in our individual leadership abilities. We saw example after example of ways leaders are able to seek out others to learn from including learning how to do things differently. Technology leaders Lisa looked up to frequently had to take courageous stances because they knew they needed to and this theme of courage is one that applies to leaders across multiple domains of course, but in this case we dive in to examples Heilmeier and others gave Lisa. How to push for quality and setting standards and being willing to understand that some people might not like what you are doing and may not like you at all. This means it is never going to be easy to take on the role of leader. Strategies for avoiding mediocrity and pursuing excellence through application of leadership principles. Lessons in creating new organizations in government and the knife fights that come with that (and need for courage, clarity and transparency and drive to bring new capabilities into existence). The virtuous role of In-Q-Tel and the phenomenal job being done by Chris Darby and his team ( There is a secret to success discussed here that will almost certainly apply to any other organization that wants to perform at this level). Advice for CEOs on how to bring capabilities to the attention of government. How can leaders of large organizations generate positive change (using the example of DoD's need to pursue new strategy and actions around 5G). The one true job of a leader. Her view on securing systems "I have never seen a secure system, nor have you or anyone else." She underscored how the approach now known as zero trust is one she strongly endorses because it flows from the approaches used by the savvy for years, including the approach of the intelligence community operators who had to learn to operate in domains of no trust (see, for example, the Moscow Rules of Cybersecurity). Her view, yes raise defenses, but know that trust is a vulnerability and employe the zero trust philosophy. What is she reading? Marcus Aurelius and his meditations, which she most strongly recommends for its context and its inspiration. And Sapiens by Harari.   Heilmeier's Rules: Lisa discussed the courage she saw in leaders like George Heilmeier, including the courage to stand up to large interests that will try to push there parochial interests through decision-makers, at times trying to do so by throwing their weight around or bully or seek to claim some ultimate wisdom. One of the way Heilmeier dealt with that was to force all who came to DARPA with a new idea or request to answer a set of very simple to understand questions which are still in use today. These simple questions, now called Heilmeier's catechism or Heilmeier's rules, were not always simple to answer, especially if an idea was not firmly rooted. They are: What are you trying to do? Articulate your objectives using absolutely no jargon. How is it done today, and what are the limits of current practice? What is new in your approach and why do you think it will be successful? Who cares? If you are successful, what difference will it make? What are the risks? How much will it cost? How long will it take? What are the mid-term and final “exams” to check for success?

Nate Fick's career has been eclectic, but with a common element of demonstrating superior leadership abilities in a diverse array of successful opportunities. Nate is currently a General Manager at Elastic, having joined the firm with their acquisition of Endgame where he served as CEO. Graduating from Dartmouth, Nate took an unconventional path of joining the military and serving as a USMC officer leading some of the first U.S. troop deployments into Afghanistan and Iraq after the September 11th terrorist attacks. His service in the military is chronicled in his New York Times best selling book One Bullet Away. The book was also a Washington Post "Best Book of the Year," and one of the Military Times' "Best Military Books of the Decade." Nate also served as the head of the esteemed national security focused non-profit think tank, the Center for a New American Security and has had a ten year tenure as an operating partner at Bessemer Venture Partners. In this OODAcast, Nate shares His observations on leadership in a variety of roles Where the emerging threat landscape is going How we should focus on increasing the yield of our cybersecurity initiatives with new technologies and approaches Why he wrote his best-selling book What philosophy allowed him to adapt to change as a soldier that carried forward into his business career Podcast Version:   Additional Reading: Nate's book One Bullet Away Meditations by Marcus Aurelius Drive: The Surprising Truth About What Motivates Us by Daniel H. Pink Turning the Map in Cyber Elastic Security

Lieutenant General Robert Ashley, USA (ret) was the 21st Director of the Defense Intelligence Agency (DIA). He retired in November 2020 after over 36 years of active-duty service as an intelligence officer. He had previously served as the Army’s lead for all intelligence (the Army Deputy Chief of Staff, G-2), where he was the senior advisor to the Secretary of the Army and Army Chief of Staff for all aspects of intelligence, counterintelligence and security.  During his long career he commanded organizations charged with gaining insights into adversary intentions and making them actionable for decision-makers. This included work overseas including six combat tours in Iraq and Afghanistan as a squadron, brigade commander, and Deputy Chief of Staff for Intelligence (J-2). Other tours included assignments leading intelligence for the Army Joint Special Operations Command; United States Central Command; and for all US forces in Afghanistan. He also led Army intelligence training and education. This OODAcast focuses on lessons for leaders of any organization, commercial, government or military. Some of the more enjoyable and interesting lessons come from being in the room with other great leaders. Imagine being in daily sessions with great's like General Mattis. Consider the lesson you would take away when you see General Mattis leveraging mentors. Time after time we see great, well read decision-makers continually seeking inputs from others, even when they have reached the pinnacle of leadership echelons.  Ashely's personal approach certainly has involved mentors and he mentions many, but his methods included learning of decision-making methods from any source. He called this approach being a "student of the human condition." The military's methods of continuing to grow and mature senior leaders is also discussed. These professional methods clearly pay off and could benefit any large commercial organization as well. General Ashley is well versed in mental models and decision-making and he references many. The OODA Loop of course, but the intelligence cycle, military COA development and others are also referenced. He also provides, in hindsight, an opinion on the most important decision he made as Director of DIA, something that may well be far more important than knowing what mental models to apply to what situation. One of the early critical thinking methods the military instilled in Ashley was a deep respect for history and a need to continue to examine lessons from the past that can be applied to today. His early exposure to this critical method of learning is directly related to the constant learning through reading that many in today's officer corps embody. Some of the books that has captured his attention lately include: The Gray Eminence: Fox Conner and the Art of Mentorship. This story of Fox Conner captures the incredible influence this individual had through mentoring others to great leadership. Some who credited him with their success include George Marshall, Ike Eisenhower and George Patton. First Principles: What America's Founders Learned From the Greeks and Romans and How That Shaped Our Country. By Pulitzer Prize winning author Thomas Ricks, this book underscores the importance of knowing which lessons from history are most relevant. The Return of Great Power Rivalry: Democracy versus Autocracy From The Ancient World To The U.S. and China. Some great historical context on why Democracies are better.  

Ellen McCarthy is a highly accomplished and distinguished executive whose career started as a junior analyst and ended up reaching to the very highest echelons of the US intelligence community. In this OODAcast we explore lessons learned from her journey, capturing insights that can inform actions for those at any stage of a career. Ellen’s career began at the office of Naval Intelligence. She then moved to Norfolk and the Atlantic Intelligence Center (where we first met). She moved back to DC and would later lead all intelligence activities for the US Coast Guard as their director of intelligence, then joined DoD’s office of the undersecretary of defense for intelligence working strategy and human capital management. Later she led the non profit public private partnership INSA (the intelligence and national security alliance), helping make that organization what it is today. She returned to government service as chief operating officer of the National Geospatial Intelligence Agency (NGA), then later led the firm Noblis as its president. Ellen was then appointed the Assistant Secretary of State for Intelligence and Research (INR), where she lead an organization famed for the highest quality of analysis in the US IC. We examine her leadership style, which was informed by exposure to several types of leaders early on in her career. Over time she developed a knack for creating visions that could help others form up on a unified purpose. She also thrived in the domain of executive action, which could come in incredibly handy when appointed to the number three position at the National Geospatial Intelligence Agency (NGA). We discuss examples of her decision-making and tools any of us can put in place to optimize our perspectives. This includes the strong recommendation to know history. In her case she benefited from a deep dive into the history of one of the great transformational leaders of the intelligence community, Wild Bill Donovan, creator and leader of the Office of Special Services (OSS), a forerunner of the organization she would later lead, the Department of State Bureau of Intelligence and Research.

Robert Wallace spent a 33 year career with the Central Intelligence Agency and is widely known for the very well done books he and co-author Keith Melton have produced on the history, culture and tradecraft of intelligence (including the SpyCraft book which was turned into a Netflix series and the Spy Sites series of books documenting the intelligence history of Washington DC, New York and Philadelphia). This OODAcast examines Robert's career from the beginning, resulting in interesting stories and insights into his leadership and management style relevant to any leader in business or government today. His professional life began as he received an MA in Political Science from Kansas University in 1968 and then received a draft notice which resulted in his two years of service in the US Army, including service in Vietnam's Mekong Delta leading long-range reconnaissance patrol teams. In the CIA his initial assignments were as a field case officer. He rose through the ranks at the agency and was Chief of Station in three locations where he directed the full range of CIA activities. Upon returning to headquarters he worked on budgets for the agency and defended spending in front of congressional oversight committees. In 1995 Robert became deputy director of the Office of Technical Service (OTS) and in 1998 was appointed its director. The OTS is the organization most analogous to the "Q" branch in James Bond movies, responsible for creating spy devices and capabilities necessary to conduct clandestine operations with safety and security. You will find Robert's observations on both leadership and management at the CIA not only interesting but directly transferable and applicable to leading any large organization. And his insights into the value of intelligence for the nation and the value of information for companies is also brought to light. Robert's book collaboration with Keith Melton began with the 2008 book Spycraft, soon followed by The Official CIA Manual of Deception and Trickery.  Their Spy Sites trilogy captures the history of American espionage from the Revolutionary War to today. Additional Resources: Spy Sites Philadelphia Spy Sites New York Spy Sites Washington DC Every Time I Get Stabbed In The Back My Fingerprints Are On The Knife Cyber Crisis: Protecting Your Business from Real Threats in the Virtual World The Splendid and the Vile

Blake Bartlett is the CEO of Janes, the well known and trusted provider of open source defense intelligence. In this OODAcast we examine lessons learned from Blake's career and path from a young student with a desire for a career in sports to success in the domain of sales. Blake believes sales is a perfect area for someone who has harnessed their passion for sports and winning and the ability to connect with people.  From there he grew to leadership of several highly regarded market intelligence organizations culminating in his current role as the CEO Janes, the first and arguably most highly successful provider of open source analysis for defense intelligence.  Blake's insights into success with sales is relevant across multiple domains of products and services, and has clearly served him well throughout his entire career. And his ability to connect with people and form trust based relationships has also clearly helped him as he needed to connect with customers, employees and stakeholders of Janes when he tool the helm in 2014. Janes is a widely known brand with a rich history. The firm began in 1989 when Fred T. Jane began selling encyclopedic insights and sketches of ships in the now iconic "Janes Fighting Ships". From that beginning Janes evolved into a major media publisher, then with the rise of the Internet age evolved into online services and now has evolved more into a provider of verifiable, trusted and accurate open source intelligence across defence equipment, military capabilities, security and defence budgets, markets and forecasts. Blake walks us through his assessment of the strengths of Janes when he assumed his leadership position including the trust and strength of the brand, but also spells out clearly how he recognized the need for change. The way one of his customers put it was that Janes was in danger of becoming the "Blackberry of the information industry " where data and information was the best but the hardest to find.  This motivated a push to make Janes information more findable, digestible and actionable by users and resulted in the Janes of today. In the discussion we examine some of Janes more interesting capabilities including new applications available now to any analyst seeking insights in to defense capabilities and operations of nations around the world. Janes now provides streams of data to organizations that want to integrate these insights into their own systems but also provides advanced applications that enable analysts to interoperate directly with data and analysis. Their content includes: - More than 40,000 profiles of military equipment (air, land and sea) in production and use around the globe - Inventories for more than 190 countries, ORBATs for 17,700 military units and 8,900 bases - Structured, consistent database of events related to terrorism, risk and security - Defence budgets for 105 countries and procurement programmes across military aircraft, combat vehicles and military ships - Market assessments, opportunities across 19 markets and data on over 7,000 defence industry organisations - Security assessments and analysis of CBRN response capabilities, production and proliferation Janes also provides training and education on the art and tradecraft of open source intelligence and services and support to organizations seeking to operationalize Janes capabilities to optimize decision-making. For more see: Janes.com

Michele Wucker is specialist in risk management and crisis anticipation and is author of the book "The Gray Rhino: How to Recognize and Act on the Obvious Dangers We Ignore". While we've all become familiar with Taleb's concept of Black Swans, we must equally become intimately aquatinted with Wucker's Gray Rhinos as they provide more obvious opportunities for actually anticipating and managing risk. During this interview, Michele takes us through the concept of Gray Rhinos with real-world historical examples, discussion of future Gray Rhinos, and strategies for engaging in real actions to identify, respond to, and mitigate future Gray Rhinos in business, society, and global affairs. The concept of a Gray Rhino is hugely important and has become embedded in how we evaluate risks at OODA with our customers. More about Michele Applying three decades of global experience in media, finance, and non-profit management and content creation, I help decision makers take a fresh look at and improve their strategies for confronting obvious but under-addressed business and policy challenges. My next book is YOU ARE WHAT YOU RISK: The New Art and Science of Navigating an Uncertain World (Pegasus Books, April 2021). YOU ARE WHAT YOU RISK is a sequel of sorts to THE GRAY RHINO: How to Recognize and Act on the Obvious Dangers We Ignore (St Martin's Press 2016), an international bestseller with translations published in Hungary, Korea, China, Taiwan, Norway, and forthcoming in Brazil. It has been highly influential in Chinese financial risk policy. I also am the author of LOCKOUT: Why America Keeps Getting Immigration Wrong When Our Prosperity Depends on Getting It Right (Public Affairs, 2006) and WHY THE COCKS FIGHT: Dominicans, Haitians, and the Struggle for Hispaniola (FSG/Hill & Wang, 1999), a social and political history of the Dominican Republic’s turbulent relationship with Haiti and the United States. Specialties: risk management, crisis anticipation, global finance, global economic trends, global risk, debt crisis, global immigration trends, economic impact of immigration, citizenship regimes, China, Latin America, Dominican Republic, Haiti, Europe, emerging markets, leadership, women. More Information: Michele's Full Bio The Gray Rhino: How to Recognize and Act on the Obvious Dangers We Ignore You Are What You Risk: The New Art and Science of Navigating an Uncertain World Michele on Twitter