Skip to main content
Success Story Podcast

Mike Baker – Ex-CIA Operative, Chairman & CEO at Portman Square Group | Lessons From The CIA

By September 24, 2023October 1st, 2023No Comments

Like The Show? Leave A Rating:

Join Our Free Slack Community To Up-Skill Yourself:

About The Guest

Mike Baker is a former CIA covert field operations officer with a distinguished 17-year career specializing in counterterrorism, counternarcotics, and counterinsurgency operations. His expertise took him around the globe, where he engaged in, organized, and supervised operations across Asia, the Middle East, Africa, Europe, the former Soviet Union, and other undisclosed locations.

In addition to his CIA career, Mike Baker is known for his role as the host of “BLACK FILES DECLASSIFIED,” a television series where he investigates top-secret military projects, unveiling hidden aspects of military technology and operations. His experiences and insights have not only contributed significantly to global security but have also provided a rare glimpse into the world of espionage and military innovation, making him a respected figure in the field of intelligence and security.

Talking Points

  • 00:00 — Intro
  • 02:14 — Mike Baker’s Origin Story
  • 06:04 — Secrets of CIA Training
  • 08:13 — The Ideal CIA Operative
  • 12:31 — Covert Lifestyle: Inside the CIA
  • 13:45 — Exit Strategies from the CIA
  • 17:15 — From Spy to Private Eye
  • 20:32 — Insights from Mike’s Time at the CIA
  • 30:16 — Sponsor: My First Million Podcast
  • 33:35 — Crafting Business Triumphs
  • 38:13 — Mastering ‘Get Off the X’
  • 40:40 — CEO’s Guide: Deciding in Uncertainty
  • 42:32 — Modern Business Threatscape
  • 46:07 — Wisdom for Entrepreneurs
  • 52:03 — Security Pioneering Strategies
  • 53:59 — Mike’s Major Mishap
  • 55:26 — Unveiling Mike’s Book & Socials
  • 56:54 — Defining Success with Mike Baker

Show Links

Podcast & Newsletter Sponsors

Watch on YouTube

Show Summary: Insights from a Former CIA Officer on Applying Spy Skills to Business

In today’s episode, I’m excited to dive into my conversation with Michael Baker. Michael is a former CIA covert operations officer who led missions across the globe for nearly 20 years.

Since leaving the agency, he has taken the lessons and tradecraft from his clandestine past and applied them to the world of business.

Michael is the founder of an intelligence and investigations firm called Prortman Square Group. He’s also the author of a new book called Company Rules: Everything I Know About Business I Learned from the CIA.

His journey is absolutely fascinating, going from tracking terrorists and weapons smugglers to building a successful company from the ground up. Even if you don’t plan on joining the CIA anytime soon, there are so many valuable insights from Michael’s experience that apply to entrepreneurs, executives and anyone leading a team.

Let’s get into it!

From CIA Officer to Entrepreneur

Michael never expected he’d join the CIA. As a kid, his dream was to become an astronaut or police officer. It wasn’t some lifelong ambition to enter the world of espionage.

He first got on the CIA’s radar through an on-campus recruiting session. The long interview process began, with lots of back and forth over an extended period of time.

He finally had his last in-person interview with a senior CIA officer. This was the moment of truth, that would determine if he made it into the clandestine service.

Michael still remembers sitting across the desk from this intimidating figure, who rifled through his file and noted that he had the absolute lowest GPA of anyone ever recruited for CIA operations.

For a moment, Michael was speechless, wondering if this was the end of the road. But he gathered his courage and responded, “Well I guess that makes me a winner.”

The officer stared at him a bit longer, then finally stood up, shook his hand, and said welcome aboard.

It was a seminal moment for Michael’s career, validating that he had more to offer than what was on paper. His academic record didn’t tell the whole story.

That surge of confidence carried him into the CIA, where he was given huge responsibility at a young age. It also later gave him the assurance he needed to leave and start his own business.

Learning the CIA Playbook

Once Michael was accepted into the Clandestine Service, the extensive training began. This started with weeks of classes on the structure, purpose and mission of the CIA.

He says this immersion into defining the agency’s objectives was critical preparation before heading out into the real world. It’s essential to understand exactly who you are working for and why, before executing covert operations.

This lesson around clearly defining the mission has served Michael incredibly well in business. Whether it’s communicating goals for the overall company or a specific project, he takes the time to ensure everyone understands the “why” behind their work.

Once the mission is locked down, Michael empowers the team to operate independently and execute. He purposefully hired people smarter than himself who know their jobs inside and out. From there, he gets out of their way and avoids micromanaging, trusting they will accomplish the mission.

As Michael explains,

“You got to hire people smarter than yourself — get people hear that all the time it’s kind of a trade saying. For me it’s easy because I can provide lots of people smarter than me so.”

Another key discipline Michael learned was understanding your operating environment. CIA officers would never head into a foreign country without learning the landscape, threats, culture and risks.

For businesses, this means deeply understanding your market, competitors, regulations, political climate and other external factors. You must look ahead to anticipate how the environment will evolve in the coming years. Changes happen fast, and you’ll be left behind if you don’t forecast and adapt.

Managing Risk Appetite

A huge part of intelligence work is assessing risk and making decisions under uncertainty. Michael says the CIA can actually swing between being hyper risk tolerant to extremely risk averse. Mistakes, bad publicity or politics can cause sudden shifts.

Companies tend to follow similar cycles between aggressive and conservative. The key is understanding your own risk appetite, and just as importantly, your stakeholders’ tolerance.

Whether its shareholders, investors, board members or customers, you need alignment on risk philosophy. This informs what decisions get made with imperfect or incomplete information.

Michael believes empowering teams to take smart risks is critical for seizing opportunities and staying competitive. The alternative is stagnation and gradual irrelevance.

Of course, teams can’t just “wing it” when making risky choices. They need to operate within clear guardrails and constantly communicate with leadership. Find the sweet spot between analysis paralysis and reckless gambling.

Getting Off The X

One metaphor Michael uses is “getting off the X.” In the CIA, the “X” refers to an ambush site. No matter how good your intelligence is, sometimes operations take a bad turn, and you end up in the kill zone. Extensive training kicks in so you can react quickly and escape.

While business mistakes usually don’t involve actual gunfire, the concept translates directly. Making rapid decisions with imperfect data is crucial. If you wait for perfect information, the situation will pass you by.

This is one of the toughest lessons for leaders and teams. We’re hardwired to avoid risk and have certainty before moving forward. But the world moves faster than analysis can keep up. Be wary of over-strategizing.

Michael had to learn on the job how to brief his team on the mission, set some guidelines, and empower them to take action. Of course, there’s a fine line between reasonable risk and chaos. Find the sweet spot to avoid paralysis but not fly blind.

The Threats Within

Given Michael’s experience in security and investigations, I wanted to tap into his expertise on threats that all companies face today.

One of the biggest dangers he sees comes from within. This “insider threat” can take many forms – leaked IP, embezzlement, fraud, or even espionage.

Michael has seen firsthand foreign agents infiltrate companies to steal research, technology, and competitive intelligence. It’s not just theoretical.

To mitigate this risk, companies must take information and personnel security deadly seriously. Security leaders should have direct access to executives, rather than be siloed.

Look for warning signs like suspicious behavior, policy violations, disgruntled employees, etc. And take common sense security measures like compartmentalized data access, need to know rules, and stringent onboarding.

The other major threat Michael highlighted was cybersecurity. Attacks are becoming more advanced and targeted. No company is immune.

It takes savvy internal security teams, continuously updated safeguards, regular penetration testing, and help from law enforcement to manage cyber risks. Falling behind on technology or best practices leaves you extremely vulnerable.

Conducting Due Diligence

One area Michael specializes in today is conducting due diligence for corporate clients before major transactions, investments, mergers and acquisitions.

He says you’d be shocked at how many companies cut corners here or rely on gut feel, only to get burned down the line. Done right, due diligence is invaluable.

As Michael cautions,

“Due diligence isn’t sexy it’s not exciting but it’s also not a heavy lift it’s not costly but yet we see time and time again we see companies that are like hey you know we don’t want to spend you know some small amount to do due diligence properly thoroughly.”

Dig deep into the officers and directors. Look for red flags in their personal, professional, and financial backgrounds. Check for undisclosed conflicts of interest. Verify credentials and performance claims.

Develop a 360 degree view before transacting or investing significant capital. Novices think it’s just checking boxes, but great due diligence uncovers subtle risks through exhaustive research. It requires tenacity and perceptive questioning.

Michael admits due diligence seems boring and costly on the surface. But compared to the liability of not doing it, it’s a smart investment that reduces exposure. One horror story can provide enough motivation.

Thinking Like A Spy

Something I found fascinating is that Michael never intended to write a “spy memoir” or capitalize too heavily on his CIA years. He wanted to move on to the next challenge of entrepreneurship.

However, he realized over time that certain principles and tradecraft from his intelligence career proved incredibly effective in the business world. These were lessons he picked up intuitively, not from any management textbook.

The idea for the book Company Rules was born out of a desire to codify and share these techniques with other entrepreneurs and leaders. Consider it a masterclass in applying spy skills to organizations.

While parts are specific to CIA operations, most of the concepts translate directly. Things like:

  • Focusing on mission clarity
  • Red teaming your own plans
  • Non-linear thinking to avoid rigid mindsets
  • Counterintelligence techniques
  • Interrogation and negotiation methods
  • Security best practices

I barely scratched the surface here. Whether or not you ever join the CIA, I highly recommend checking out Michael’s book for a crash course in thinking like a spy to gain competitive advantage.

Staying Small and Tailored

Given his unconventional background, I was curious how Michael structured his investigative company once transitioning to entrepreneurship.

He explained that a key advantage has been staying small. Rather than rapid expansion, he focused on specialized service and tailored solutions. This earned trust from big clients, despite the large competitor firms.

As Michael puts it,

“I think that that actually has worked in our favor to stay relatively small and sort of provide this this tailored approach to every client we deal with.”

This personalized approach is only possible because of his obsessive focus on customer service and delivering results.

He never rests on past successes.

Continuously Learning

Towards the end of our conversation, I asked Michael for his best advice to others looking to pivot from one demanding career into something totally new.

His response underscored the importance of lifelong learning, growth and finding new challenges. Too often, people get stuck relying on past accomplishments and neglect to build new skills.

In Michael’s words,

“You have to be able to find that next challenge that keeps you moving forward or that or that provides that next opportunity to grow and if you don’t then that’s when you know that’s when trouble can set in.”

He could have comfortably retired early and lived off his CIA career. But the thirst for new knowledge and entrepreneurship called him. That’s allowed him to take his unique expertise into a very different realm and find success.

No matter how impressive your background, don’t let it define you forever. There are always new things to master and contributions to make.

Key Takeaways

Michael’s journey makes for an incredible story. Here are my key takeaways from our conversation:

  • Clearly define the mission – on both a macro and micro level
  • Take time to understand your operating environment
  • Empower talented people and avoid micromanaging
  • Instill an appropriate risk appetite within your team
  • Make rapid decisions amidst uncertainty
  • Insider and cyber threats are growing – take them seriously
  • Due diligence provides invaluable risk reduction
  • Look for lessons from other fields like intelligence that translate
  • Stay small and specialized to provide tailored solutions
  • Never stop learning and taking on new challenges
  • Family first

That’s a wrap on my conversation with Michael! His unique career path and blend of spy skills with business strategy makes for an intriguing story. I’d love to hear your key takeaways.

What stuck out to you most from Michael’s experience? Do you see any parallels to your own work? How might you apply some of these lessons around risk-taking, decision making, or security?

Let me know what you thought of the episode and share your favorite parts on on Twitter. I love connecting with you all there.

Until next time,


What is the Success Story Podcast?

On this podcast, you’ll find interviews, Q&A, keynote presentations & conversations on sales, marketing, business, startups, and entrepreneurship.

The podcast is hosted by entrepreneur, business executive, author, educator & speaker, Scott D. Clary.

Scott will discuss some of the lessons he’s learned over his own career, as well as have candid interviews with execs, celebrities, notable figures, and politicians. All who have achieved success through both wins and losses, to learn more about their life, their ideas, and insights.

He sits down with leaders and mentors and unpacks their stories to help pass those lessons on to others through both experiences and tactical strategies for business professionals, entrepreneurs, and everyone in between.


Host of the Success Story Podcast:









More posts by

Leave a Reply

Skip to content