OODAcast

Kevin DeSanto is an investment banker delivering advice and execution assistance to high growth businesses preparing for M&A and financial transactions. His company, KippsDeSanto, has developed a reputation for trusted execution support for companies in government contracting, aerospace, defense and cybersecurity. He leads teams that advise senior management, boards of directors and shareholders.

The art and science of this type of investment banking can only be perfected by experience and Kevin has just that. In this OODAcast we tapped into his experience to bring out lessons relevant to any CEO seeking to build future value and prepare for future events. This includes getting Kevin's insights into the best way to prepare for due diligence assessments.

For more see:

KippsDeSanto

Kevin DeSanto on LinkedIn

Bradley Rotter is a visionary investor who has pioneered investments in many new alternative investments classes including having been an early backer of hedge funds in 1982 while speculating on the Chicago Mercantile Exchange. He was also an early investor in Bitcoin and other cryptocurrency ecosystems and at a dinner with OODA CEO Matt Devost in 2012 predicted Bitcoin would exceed the price of gold.

Bradley moved to San Francisco in mid 80's to be close to the technology fountainhead of the Bay Area. In 1995 he was famously quoted saying "this internet thing is going to be big" and this vision guided his investments in several successful technology companies.

Bradley has made numerous VC and PE investments, with a particular focus on internet and technology and spanning from hedge funds to satellites.

This wide ranging conversation hits on multiple high tech topics including quantum computing, crypto currencies and the data analytics.

Additional Reading:

Quantum Computing Sensemaking

Is Quantum Computing Ushering in an Era of No More Secrets?

Andrew (Andy) Lustig is a partner at the high tech law firm Cooley, where he focuses on private equity investments, mergers and acquisitions and the general corporate representation of high-growth technology companies in both the commercial and government marketplace. His practice includes a wide range of industry sectors including information technology, national security, cybersecurity, data analytics, software and telecommunications. He also represents a number of leading venture capital and private equity firms.

Cooley is widely known for their work with high growth tech and life sciences companies, and Andy brings his deep experience in a wide range of issues to this discussion. He discusses his views on things CEOs can do to prepare for growth, including things to do to prepare for due diligence. He also discusses the a CEO focused networking activity he helps lead called Mission Link (CEOs looking for more insights on this should contact Bob at OODA LLC and we will get you more information).

Andy is well versed in technology and its mission impact. We discussed state of the art tech including capabilities in the domains of cybersecurity, communications, space, IT, quantum computing and IoT.

For more see:

Andy Lustig on LinkedIn

Cooley

OODA Due Diligence Services

Paul Pagnato migrated from a career as a scientist looking for life in outer space to one of the top financial advisors in the U.S. with a keen eye for tracking innovation, exponential change, and other emerging global issues. He is also the author of the recent book, The Transparency Wave, which highlights the essential role that transparency plays in future innovation and entrepreneurial success.

Paul A. Pagnato is Co-Chairman Cresset, Founder PagnatoKarp, a top family office and private wealth management firm with over $9.5 billion assets under management.¹ Paul is a top advisor with more than 27 years of industry leadership, ranked #1 in Virginia on Forbes Top Wealth Advisors and #2 in Virginia on Barron’s Top 1,200 Financial Advisors lists. PagnatoKarp is Best Multi-Family Office ($2.5B to $5B AUM/AUA) by Family Wealth Report Awards and a Virginia Business Best Place to Work.

Paul is also founder of the TrueFiduciary® Institute, a non-profit with a Massive Transformational Purpose of positively impacting one million lives through digital education and True Fiduciary® standards of exponential transparency, targeting the well-being of students, individuals and advisors.

Paul has been advising clients for more than 27 years, specializing in CEO Founders, entrepreneurs and UHNW families. Paul spent 19 years with Merrill Lynch, where he founded the Washington, D.C. Private Banking & Investment office. He began his career as a microbiologist with NASA and McDonnell Douglas working collaboratively to search for life in outer space.

In this OODAcast we tapped into Paul's extensive background to seek insights relevant to decision-makers building high growth companies. We also dive into his newest book, The Transparency Wave, where he examines how in a time of exponential growth across multiple sectors, those who fear transparency are doomed to remain in the past. Paul provides example after example of how exponential growth is here now and how transparency provides significant advantage to any organization in this new domain.

For more see:

The Transparency Wave

Pagnato Karp

Bill Crowell is a senior executive with extensive experience in government (rose to the level of Deputy Director of the National Security Agency) and in industry. He has been a CEO of leading companies like Cylink, taking them through growth to acquisition. He has been a director of multiple public and private companies with a track record of steering firms to profitability and successful exits. He continues to serve on corporate boards while also helping steer successful operations at one of the most famed Venture Capital firms in the nation, Alsop-Louie.

Bill has been a boss, mentor, friend and advisor to both Bob Gourley and Matt Devost through the years, and has long been a valuable member of our OODA Network. In this video we ask Bill for insights of use to firms seeking to evaluate a business prior to acquisition, specifically seeking to do a better technology due diligence assessment.

Bill provides insights on due diligence relevant to startup firms seeking VC investment, growth firms seeking funding to accelerate market penetration, and established firms seeking a private equity backed transaction.

For more on these topics see:

• Bill Crowell on LinkedIn
• Alsop-Louie Partners
• OODA Due Diligence Consulting
• Lessons Learned From a Decade of Technology Due Diligence Consulting

Mark Weatherford is an icon in the cybersecurity field. He is widely known as a mission focused leader who builds teams and gets hard things done. His career included success in the US Navy as a cryptologist, leadership and management in a major defense integrator, CISO for two states (Colorado and California), CISO of the nation's regulatory organization for our power grid (the NERC), head of security efforts for the newly formed DHS, and operational CISO roles and advisory board positions for several US corporations.

Our OODAcast with Mark focused on his insights for the cybersecurity community, including views on how to stay informed in dynamic environments, how to approach the position of CISO, how to optimize your career planning, and how to work with corporate boards as a CISO. He also provides advice for board members on interacting with their CISO and security team.

Mark has written on CISO leadership, including two posts for OODA members at:

• 10 Rules For Cybersecurity Salespeople
• Embracing a Future of Technical and Political Churn

Other Resources:

• Mark Weatherford on LinkedIn
• Covid-19 Sensemaking
• Mitigating Risks To America’s Cognitive Infrastructure
• 10 Red Teaming Lessons Learned Over 20 Years
• The Five Modes of HACKthink

Brad Meltzer is the #1 New York Times bestselling author of The Culper Ring Trilogy (The Inner Circle, The Fifth Assassin, The President's Shadow), The Escape Artist, The Book of Lies and many other thrillers loved by millions for their realism and well researched fact based themes and drama filled plots. He is also widely known for his non-fiction history including The First Conspiracy, a work based on extensive research that reads like a thriller while giving the foundational stories of the nation's espionage and counterintelligence services. His most recent non-fiction book examines a plot to kill Abraham Lincoln while he was on his way to his inauguration. This one too reads like a thriller, exposing us to the realities of an era when the nation was divided by polarizing political factions.

We Interviewed Brad with an eye towards lessons for business leaders and operational decision-makers today. Brad reveals insights from his research into the characters of leaders like George Washington, Abraham Lincoln and a wide range of heroes in his "Ordinary People Change The World" series and provides us with recommendations that we can all take onboard. He does so with an enthusiasm that is infectious, ending the discussion with insights that may help us all as we map our way towards a brighter, more prosperous and just future.

There is hardly a person more suited to speak with the OODA team on OODA Loops that former Air Force pilot John Robb. John has worked successfully in a variety of domains to include the special operations community, as an industry analyst, successful start-up founder, and national security expert.

John Robb has distinguished himself with a career of critical analysis on a variety of security, technology, and cultural issues throughout his career to include his popular book "Brave New War" and his current Global Guerrillas content community and the GG Report.

In this interview we discuss:

• John's career trajectory that took him from the Special Forces community to becoming the first Internet analyst at Forrester Research to start-up founder and executive to being a highly sought after red teamer and consultant for the DOD, JCS, CIA, NSA, and a host of other organizations.
• Useful frameworks for looking at the world to enable executive decision making.
• Decision-making in the age of Covid-19.
• Emerging threats and technologies.
• How Orientation is the most difficult component of the OODA Loop.
• How science fiction can inform our perspective on the present and near future.

Other Resources: John's Full Bio

Global Guerrillas Report

Brave New War Book

Covid-19 Sensemaking

Mitigating Risks To America’s Cognitive Infrastructure

10 Red Teaming Lessons Learned Over 20 Years

The Five Modes of HACKthink

The leadership team at OODA have had the pleasure of working with and learning from Bobbie Stempfley since her leadership of the Department of Defense Computer Emergency Response Team (DoD CERT) after she established it in the late 1990's. This OODAcast captures insights from Bobbie that can inform the action of leadership of corporate and government leaders alike.

She has had a broad influence on the cybersecurity community, including rising to senior executive position in the DoD and then later helping DHS as they established themselves as a new Department. She also lead Cybersecurity activities at MITRE.  Through it all she has been a mentor to 1,000's and a thought leader known for anticipating and mitigating risks. Now as director of the Carnegie Mellon University Software Engineering Institute's CERT Division (since 2017) she leads a highly respected team of researchers examining some of the nation's biggest challenges in cybersecurity, including insider threats, the security of Artificial Intelligence, and ways to measure the impact of cybersecurity solutions.

Topics we discuss with Bobbie included:

• Her foundational story
• Views on the current situation including actions we should take to reduce cyber risks right now
• The situation regarding the security of artificial intelligence solutions
• Advice for cybersecurity professionals seeking to stay current.
• Research we should be aware of at CMU
• Advice for the youth of today

Related Resources:

• SEI CERT
• Bobbie Stempfley on LinkedIn
• An Executive’s Guide to Cognitive Bias in Decision Making: How we think is critically important.
• A Decision-Makers’s Guide to Artificial Intelligence: A plain english overview with the insights you need to drive corporate decisions
• The Executive’s Guide to Quantum Computing: What business decision-makers need to know now about quantum superiority
• The Executive’s Guide to the Revolution in Biology: An overview of key thrusts of the transformation underway in biology and offers seven topics business leaders should consider when updating business strategy to optimize opportunity because of these changes.
• OODA COVID-19 Sense-making: A dynamic resource for OODA Network members looking for Coronavirus/COVID-19 information to drive their decision-making process. We’ll update it with new links as we encounter them. This is not meant to be a comprehensive list, but rather a compilation of the most useful resources.
• The 2020 OODA Cybersecurity Watch List: list can serve multiple stakeholders. Investors can find firms that have demonstrated good product-market fit and are good candidates for follow-on funding. CISOs can find companies that have demonstrated real disruptive technology potential and at least enough traction to prove they are worth considering.
• OODAcast on YouTube: OODA's YouTube Channel

Marc Ambinder is a journalist, researcher, historian, author of bestselling books and a teacher/mentor to many. We invited him on the OODAcast to help our community as we continue to look for insights that can drive operational decisions.

From Marc's bio:

For 20 years, Marc Ambinder has told true and complex stories about the world, revealed some of its deeper secrets, and has taught thousands of others how to do the same.

He has managed teams of reporters, consultants and students, and has co-created several innovative digital news products. As a reporter, Ambinder held positions at the zenith of journalism (ABC News, CBS News, the Atlantic). He has collaborated with industry (Disney/ABC, Facebook, Palantir) and has made excursions into academia (Penn, USC). An SME on national security, American politics, elections and government, corporate communications, digital and cybersecurity and nuclear policy, he is at present the counter-disinformation lead for USC’s Election Cybersecurity initiative.

This discussion covered many topics of high interest including Marc's books:

• The Brink: President Reagan and the Nuclear War Scare of 1983
• The Command: Deep Inside the President's Secret Army
• Deep State: Inside the government secrecy industry

We also tapped into Marc's close tracking of the dynamics around the current pandemic as well as his work in helping to improve the security of the nation's elections to gather insights on what the future may hold.

Related Resources:

• Marc Ambinder on LinkedIn
• Marc Ambinder on Twitter
• Tighten Your OODA Loop on Covid-19
• How the Coronavirus will impact your mid to long range strategic planning
• Mitigating Risks To America’s Cognitive Infrastructure
• OODA’s Special Reporting on the Federal Technology Market.
• The Top 10 Security, Technology, and Business Books
• OODAcast on YouTube: OODA’s YouTube Channel