I talk about digital writing & personal progress

Here's a quick rundown of how I've spent my last 5 years:

1. Studied math and played football at Princeton. I graduated in 2018 with a degree in financial engineering and played center for the Tigers. In college, I was a 280-pound offensive lineman, so for the last 5 years, I've had to completely rewrite my personal operating system on the health & fitness front. I currently weigh 185 pounds and have learned a lot along the way!

2. Graduated and immediately started working for BlackRock in New York City. I worked as a junior hedge fund trader for 4 years, focusing on global macro markets. This was my dream job and the only corporate job I've ever had. In fact, it's the only job *interview* I've ever had (since I interned there as a junior in college).

3. Realized working for someone else was not going to be the long-term path for me. 12 months into working on Wall Street, I saw someone in their mid-40s ask their boss for permission to go to their son's Little League game. At that moment I realized I wasn't cut out to take directions or instructions from other people for very long.

4. Started to write on my old blog, then on Twitter. Rather than quit immediately, I started to passively explore other opportunities by writing online, starting out on my old blog (which no one knew existed), then transitioning to Twitter in July of 2020.

5. Changed my trajectory with a 30-day writing challenge, which led me to start Ship 30 for 30. In September 2020 I was ready to give up writing entirely. But I gave it one more shot, this time moving from a weekly blog post to a daily Twitter thread. The challenge was a huge success. It took me 9 months to reach 100 followers and 1 month to go from 100 to 2,000. And that personal writing challenge turned into the foundation of Ship 30 for 30, which started as nothing but a Slack accountability group to help people publish consistently.

6. Scaled Ship 30 while working remotely for all of 2021. I built and scaled Ship 30 with Nicolas Cole to over 2,000 students in 2021—all while continuing to work full-time (remotely) for BlackRock. But towards the end of 2021, Ship 30 hit an inflection point and it no longer made financial sense for me to continue working on Wall Street.

7. Left BlackRock in March of 2022 to write and build on my own. After weeks of weighing the pros and cons and trying to project my path forward, I made the decision to leave BlackRock and chart my own path. 15 months into making that decision and I'm confident it's the best one I've ever made.

Dickie Bush 🚢

I used to have one severe addiction:

Planning.

My brain loved the cheap dopamine of gathering:

• Books to read
• Tasks to complete
• And videos to watch

But when it came to taking action, the euphoric rush faded.

What ended my addiction?

This story of two men learning to fish:

The first fisherman heads straight to the marina to buy the best fishing boat money can buy.

He specs out a custom, carbon fiber rod.

And he spends time reading up on everything there is to know about fishing:

• Casting techniques
• Baiting techniques
• Reeling techniques

You name it, he's bought the book on it.

And of course, he's watching the fishing channel every night for hours, learning from the best of the best.

A few months later, he finally feels ready to fish.

The next day, he heads out on the lake in his new boat with his fancy rod and wealth of fishing "experience" built up over the last few months.

But six hours in, nothing. Not even a nibble.

What happened?

Turns out, the second fisherman had already sucked the lake dry.

On day one, the second fisherman grabbed a shitty rod, sliced up a hot dog, and went out to the lake.

• The first day, nothing
• Second day, nothing
• Third day, nothing
• One week, nothing

But on the eighth day? His first nibble.

And every day after, he honed his technique.

He found a baiting technique that worked a bit better. Or a new spot with a few more fish.

And after three weeks of iteration, he found the winning combination.

Before long, he was hauling in hundreds of fish every day. To keep up with his daily haul, he hired a small team to help him. And from there, he opened a restaurant with fat margins to sell his fresh fish.

And after that, he opened a fishing school to teach others his craft.

He did all of this while the first fisherman sat around gathering gear.

Sure, the first fisherman felt productive. He was "learning" after all, right?

But there was one difference: feedback.

Every day the second fisherman had an idea of something that might work better. And he went right to the market to validate his assumption. If it worked, his strategy improved. And if it failed, he learned something new.

The moral of this story?

Get to action as quickly as possible.

When you find yourself gathering gear, grab a shitty rod and start fishing.

Bad way to learn copywriting:

1. Bookmark dozens of posts
2. Read all the books
3. Apply none of them

Instead, just read The Adweek Copywriting Handbook by Joseph Sugarman.

It taught me more about copywriting than dozens of books combined.

And you can steal Sugarman's 7-step process to write high-converting copy (that helped me generate $15,000,000):

—
📌 Copywriting helped me build a 7-figure writing business.

(While working 12-hour days at my Wall Street job)

But I made my first $10,000 on the internet as a ghostwriter.

And right now, becoming a LinkedIn Ghostwriter is the easiest way to land high-paying clients.

Want to know how to land LinkedIn writing clients in 2025?

Here's a free, 5-day email course on how to get started: https://lnkd.in/eCFfC5cX

7 Steps To Write High-Converting Copy (From Joe Sugarman)

At 24, a stranger on the internet paid me $5,000.

The crazy part?

I thought they'd sent it by mistake!

But I'd actually just stumbled across an insanely lucrative business anyone can start:

Ghostwriting.

Everyone should have writing clients who pay $5,000+ for a project.

(This is ultimately how I quit my job on Wall Street so I could travel and work from anywhere in the world.)

But most people are stuck figuring out:

• What service to sell
• Which clients to target
• How to charge premium rates

So, last month, Nicolas Cole 🚢👻 and I put together the Writer Positioning Playbook to help you:

• Escape the freelancer rat race
• Confidently charge high-ticket prices
• Land ideal clients who value your expertise

Inside, you'll find:

• The 1 simple shift to 10x your rates overnight
• A 3-step framework to upgrade your Positioning
• An AI prompt to find 5 high-paying clients for YOUR specific background

Plus, you'll see real examples from a $3M ghostwriting agency.

Want access?

Comment "playbook" and I'll send it across (for free).

And if we're not connected, send me a connection request with the word "playbook" and I'll DM it to you.

How To Land $5,000 Writing Clients

A daily habit I wish I'd started earlier in my 20s:

(It's not investing)

Writing & publishing online every single day.

In the beginning, I tried everything:

• Every app
• Every "simple hack"
• Every piece of writing advice

And I still struggled to build a daily writing habit.

But then I studied the routines of legendary writers.

And their secrets have helped me write every day for 5+ years.
 
These are the 10 tiny habits that make writing every day effortless:

—
📌 Writing online completely changed my life:

• Helped me quit my corporate job
• Made my first $10,000 online as a ghostwriter
• Built my $19,000,000 digital writing business

And it also taught me ONE thing for certain:

The easiest way to make money online is to become a ghostwriter.

Want to land high-paying ghostwriting clients?

I wrote a FREE 5-step blueprint with everything you need to make money ghostwriting on LinkedIn.

Click here to get (free!) instant access: https://lnkd.in/eQW3B7Y4

10 Tiny Habits To Make Writing Every Day Effortless 

This French teacher had one goal in mind:

To 4x her income.

Why?

Because Laura B. wanted to fund the work she's most passionate about—teaching her students how to become fluent in French.

So she took the plunge and joined our Premium Ghostwriting Academy.

And as a ghostwriter, she scaled quickly.

She sold:

• 5 Email Courses
• 8 Consulting Packages
• Dozens of Thought Leadership Packs

And now she's using this extra income to build her tutoring business.

Laura's example goes to show that anyone can become a ghostwriter and use this in-demand (and lucrative) service to either:

1. Create a new income stream
2. Or scale their existing income

Because executives, founders, and creators around the world are realizing how much they need a personal brand to scale their businesses.

And the salaries I've seen them pay are wild:

• Content Strategist at OpenAI ($319K - $393K/yr)

• Thought Leadership & Narrative Manager at Google ($211K - $297K/yr)

• Head of CEO Content at PayPal ($137.5K - $236K/yr)

And the best place to start right now is LinkedIn.

Want to start making money as a LinkedIn Ghostwriter?

I put together a free, 5-day email course to help you land high-paying writing clients.

Click "Visit my website" at the top of this post to get instant access.

Lester Chng

Cyber CEOs Brand Strategist. I build your brand as you build your business. | Senior Cybersecurity Advisor | Author | Naval Officer | CISSP | 🇨🇦🇸🇬 |

You head a leading cybersecurity firm.
But your online presence doesn't reflect it.

In fact, being invisible is damaging. 

You understand the power of thought leadership.
You know LinkedIn shapes deal flow and adds credibility in the industry.
You just don’t have the cycles (or the copy) to share your expertise and experience.

You have stories worth telling.

The insights from being in the trenches.
The deep conversations with your ace teams.
The hard discussions with your clients. 

Don’t let this wisdom go to waste.

That’s where I come in.

--------------------------------------------------------------------------------------------

How we work together.

Profile & Positioning
=> Rebuild your LinkedIn profile so visitors see industry authority, not “another vendor.”

Content engine
=> Ghostwritten posts that leverage your insights and expertise into engaging LinkedIn posts. 

Outreach campaign
=> Targeted DM campaigns and audience-building strategies that build your authority and land you on podcasts and conference stages.

--------------------------------------------------------------------------------------------

You focus on growing your firm and protecting your clients.
And we will ensure the industry, clients, prospects, and investors can’t ignore it.

Let’s build the personal brand that commands the cybersecurity conversation and drives business.


Worked with global client portfolio 
- MSPs
- MSSPs
- Agentic AI SOC
- AI-powered GRC 
- Operational Resilience 

Senior Advisor, Financial Crimes Unit Exercises. BMO Fusion Centre

Execution of Financial Crimes Unit Exercise and Drill Program
• Design and execution of exercises and drills to operationalize the Financial Crimes Unit Fusion Centre
• Scenario creation and exercise execution for Information Security, Enterprise Fraud Management, Physical Security, and Global Crisis and Continuity Management teams 
• Providing effective challenge of incident response readiness through exercise observation
• Execution of enterprise-wide Purple Team Exercise


Cybersecurity Exercises: Purple Team, Ransomware, DDoS, Malware, Data Corruption, Data Breach, 3rd Party Incidents
Fraud Exercises: ATOs, Attack on Payment systems, Business Email Compromise, PII Breach
Physical Security Exercise: Active Assailant, Civil Unrest, Bomb Threats
Crisis Exercises: Disaster Recovery, Business Continuity, Operational Resilience, Fire Incidents, Natural Disasters, Utilities Disruption

Write books, speak at TEDx, full time cyber pro, mum.

Sometimes I wonder how she expands time.

I interviewed my friend Zinet Kemal, M.S.c, who is an immigrant, mother of four, author, TEDx speaker & Cybersecurity professional. She is passionate about educating and empowering children on online safety and cybersecurity careers.

Empowering the Next Generation

Q5: What inspired you to write children’s books about online safety?

As a mom of 4 and cybersecurity practitioner, I saw a gap in how we teach kids to navigate the digital world safely. I wanted to start that conversation early in a fun, relatable way.

Q6: For newcomers in cyber, what’s your top tip for building skills and visibility?

Learn by doing. Share what you learn. Even small wins and lessons can inspire others and help you grow your voice and network in the community.

Women in Cyber & Representation

Q7: What barriers still hold women back in cybersecurity today?

Representation and confidence. When you don’t see people like you in the room, it’s easy to doubt you belong but you absolutely do. Lack of respect and enough true support from allies.

Q8: What would a more inclusive cyber industry look like to you?

A more inclusive cyber industry is one where everyone feels seen, heard, and valued. It is where representation drives innovation and thriving, not just participation and surviving.
_____________________________

If you enjoyed this interview series, please follow Zinet. She frequently shares about her cybersecurity journey and is a gem to the industry.


P.S What is a barrier that still exists in the job market?

Another reason to be active on LinkedIn and you won’t like this. 

People are too busy to notice you. 

- social media doom scroll
- Netflix and chilling 
- project deadlines
- kids schedule 
- home stuff  
- life events 

And there you are, typing away on your keyboard, working your bum off. Spending all your hours and energy delivering the best work that you can. 

But you forgot to spend time on yrself. 

Time to learn more. 
Time to recuperate. 
Time to invest in you. 

Use LinkedIn to share just abit more of
- what you do
- what you think
- what you are like 

You work hard enough to be noticed. 

Don’t let all that go to waste because you are afraid of what yr colleagues and friends think. 

Let them live with their insecurities. 

You have a career + reputation to build.

No alternative text description for this image

You are all busy. I don't expect you to read my history, so here is a little about me.

𝗕𝗼𝗿𝗻 𝗮𝗻𝗱 𝗿𝗮𝗶𝘀𝗲𝗱 𝗶𝗻 𝗦𝗶𝗻𝗴𝗮𝗽𝗼𝗿𝗲.

Never the model student.
Made a career choice at 19.
To serve in the Navy and see the world.

𝗖𝗮𝗿𝗲𝗲𝗿 𝗶𝗻 𝘁𝗵𝗲 𝗡𝗮𝘃𝘆

Daily lessons of leadership, critical thinking.
Ran the wargaming and simulation centre.
Left in 2017 after rejecting a promotion and the opportunity to command a ship.

𝗢'𝗖𝗮𝗻𝗮𝗱𝗮

Moved to Canada w no corporate exp
Struggled for years to climb a ladder
Fortunate to move into cybersecurity

𝗖𝘆𝗯𝗲𝗿𝘀𝗲𝗰𝘂𝗿𝗶𝘁𝘆

Currently in my 3rd role in cyber.
1. Project Management
2. Senior advisor - security exercises
3. Senior advisor - security exercises

𝗖𝘂𝗿𝗿𝗲𝗻𝘁 𝗲𝗻𝗱𝗲𝗮𝘃𝗼𝗿𝘀

Full-time at Rogers Cybersecure Catalyst, Toronto Metropolitan University. 
Best place I have worked in Canada.

Need cybersecurity tabletop exercises, cyber range training, cyber advisory services?

Give me a shout.

𝗖𝗼𝗻𝗰𝘂𝗿𝗿𝗲𝗻𝘁 𝗮𝗰𝘁𝗶𝘃𝗶𝘁𝗶𝗲𝘀

Book author
The Essential Cybersecurity Ex Playbook.
I still refer to it when I design exercises. 
Get it if you are tasked to run exercises.

Ghostwriter for Cyber CEOs and Founders
Your LinkedIn Account is a goldmine.
Build your thought leadership and authority.
I write your LinkedIn posts for you.

P.S What did you not know abt me?

How to create a content calendar in 10 mins and never worry abt what to post. 
 
Follow this process and save time. 
 
I never worry about what to post about. 
Not because I have a constant stream of inspiration and the words flow naturally. 
 
Writing and posting on LinkedIn has become part of my professional portfolio and I constructed a simple system. 
 
1. Decide what your objectives are 
- to establish thought leadership 
- to build stronger professional relations 
- to bring awareness to brand and product 
 
=> The clearer this is, the easier it gets. 
 
2. Decide how frequent you post 
- minimum twice a week 
- thrice is good 
- seven if able 
 
=> Schedule your time to write. 
 
3. Decide what are your content pillars 
- keep it no more than 2-3 
- for me it is ghostwriting 
- and cyber exercises 
 
=> What you want to be known for? 
 
4. Decide the various themes 
- posts that builds awareness 
- posts that builds authority 
- posts that builds trust 
 
=> How do u get ppl to like, trust, know u? 
 
5. Decide the theme for the day 
- Mon = Awareness 
- Wed = Authority 
- Fri = Trust 
 
=> Saves your time thinking of the theme 
 
6. Mind-map and research abt topics 
- Content should be planned 
- Mind-map your experience 
- Answer yr client qns 
 
=> If it is not planned, u will struggle  
 
7. Keep it simple and you will follow 
- create a simple system 
- don't complicate it 
 
=> It takes some prep but well worth it 
 
I planned out my content calendar and stick to it for at least 6 months. 
 
Struggling with posting consistently? 
Chances are you are winging it. 
 
Do you also leave yr business to chance? 
Didn't think so. 
 
It's time to take action. 
Get in touch. Start being intentional.

Getting into Cyber feels like winning the lottery.

Here’s how to increase your odds.

I interviewed my friend Zinet Kemal, who is an immigrant, mother of four, author, TEDx speaker & Cybersecurity professional. She is passionate about educating and empowering children on online safety and cybersecurity careers.

Journey & Motivation

Q1: You started in law before moving into cybersecurity. What inspired that switch?

I wanted a career where I could make a tangible impact and continuously learn. Cybersecurity offered that blend of purpose, challenge, and growth that instantly drew me in.

Q2: Hands-on experiences like competitions helped launch your career — what advice would you give to others trying to break into cyber?

Don’t wait to feel “ready.” Jump in, join competitions, try extra curricular stuff and learn by doing. Real-world practice builds confidence faster than any certification alone.

Cloud Security Expertise

Q3: What’s one common mistake organizations make when moving to the cloud?

Rushing migration without embedding security from the start. Security shouldn’t be an afterthought. It should guide every design and decision.

Q4: How do you balance speed and security in fast-paced cloud environments?

By automating what you can and baking security into the pipeline. That way, teams can move fast and stay secure without friction.
_____________________________

If you enjoyed this interview series, please follow Zinet. She frequently shares about her cybersecurity journey and is a gem to the industry.


P.S Have you seen her award list!

“I’ll take a break from writing/posting”. 

That’s what I told myself as I returned from my vacation. 

“It will be easy to get back into it”. 

Just like my exercise routine, my writing and networking rhythm were severly derailed. 

Even though my systems and tools were in place, I need to reconvince myself of the intend of being active on this platform. 

And it really does fall back to the why. 

Once that is reaffirmed, then the other pieces of the how kicks back in. 

Here’s back to sharing:
- how organizations should use cyber exercises to improve their readiness and resilience 
- how cyber CEOs should use LinkedIn to drive brand awareness 

P.S who thinks the LinkedIn feed is darn boring these days. Let’s start sharpening our storytelling skills.

Cyber CEOs are missing one of the biggest opportunities on LinkedIn.

Your founder story.

Not the pitch.
Not the product.
The reason you started.

Here is why it matters.

1. It builds trust faster than yr website.

People want to know the conviction behind your company. Your story answers the core question every buyer has: why should I trust you.

2. It humanizes your brand.

Cybersecurity is technical and crowded. Your story cuts through the noise and shows the person behind the mission.

3. It creates instant differentiation.

Competitors can copy language, pricing, and positioning. They cannot copy your journey.

4. It strengthens every future conversation.

When people understand your why, your product demonstrations, sales calls, and partnerships become warmer and easier.

Your founder story is not optional.
It is a strategic asset.

If you do not tell it, your audience will never hear it. And don’t wait for permission to share too. 

No one is gonna give you that.

Data is absolutely vital for effective healthcare.

But how do we manage the risk and liability?

Managing data and addressing privacy issues are major risk areas for many healthcare organizations. Add AI to that picture and it can be messy very quickly.

I interviewed my friend Patrick Lo, the CEO of Privacy Horizon, who helps his clients make sense of the ever-changing landscape of privacy and the impact of AI.

The Evolution of Privacy in the Health Sector

Q1: You’ve worked across both government and private healthcare environments. How has the concept of “privacy by design” evolved in the health sector over the past decade?

In the last ten years, privacy by design has evolved from a compliance trend to a core design principle integrated into digital health innovations and an operational imperative. It’s now focused on instilling trust and resilience in systems rather than merely fulfilling regulatory requirements.


Q2: What are some persistent privacy misconceptions you still encounter among healthcare organizations today?

A common misconception is that privacy is the same as security or that having a lawyer create an agreement and terms of use ensures protection and compliance. Effective privacy management requires ongoing governance that aligns people, processes, and technologies to foster accountability and manage data throughout its lifecycle.
_____________________________

If you enjoyed this interview series, please follow Patrick. He is a healthcare privacy expert and has helped organizations build privacy and security programs.


P.S. What other privacy mistakes do you see healthcare organizations make?

Privacy mgmt shouldn't be an afterthought.

Yet many choose to only address it later.

That is a risk startups should address early in their journey, especially if they handle sensitive information. Add AI to that picture and it can be messy very quickly.

I interviewed my friend Patrick Lo, the CEO of Privacy Horizon, who helps his clients make sense of the ever-changing landscape of privacy and the impact of AI.

Operationalizing Privacy — From Compliance to Trust


Q3: Many healthcare startups treat privacy as a barrier to speed. How do you help founders operationalize privacy without slowing innovation?

I encourage them to view privacy as an enabler rather than an impediment. We help clients establish strong privacy foundations and clear growth plans. We offer Virtual Privacy Officer service to help them navigate privacy-related challenges and implement best practices, allowing them to concentrate on their core business. Embracing privacy can not only benefit their bottom line but also set them apart from the competition. Effective privacy management builds customer trust and differentiates them from competitors.


Q4: What frameworks or approaches have proven most effective in embedding privacy into day-to-day clinical or product operations?

The NIST Privacy Framework, ISO 27701, and the CSA Model Code for the Protection of Personal Information provide a solid foundation, but achieving success often requires creating and executing a well-organized privacy management program. This program should encompass an accountability framework, functional tools such as privacy impact assessments (PIAs) and risk registers, and training that ensures everyone is responsible for privacy, not just the compliance team.
_____________________________

If you enjoyed this interview series, please follow Patrick. He is a healthcare privacy expert and has helped organizations build privacy and security programs.


P.S What other privacy frameworks would you recommend?

It seems like privacy is a premium these days.

And it can be sidelined if we don’t preserve it.

AI models feed on data. And yet so many organizations have headed straight for the AI gravy train without due consideration for the impact on data management and privacy. 

I interviewed my friend Patrick Lo, the CEO of Privacy Horizon, who helps his clients make sense of the ever-changing landscape of privacy and the impact of AI.

The Future of Privacy Leadership

Q7: What qualities will define the next generation of privacy leaders in healthcare?

Future privacy leaders will combine a strong understanding of technology, turning intricate risks related to AI, data, and cybersecurity into transparent, human-focused governance approaches that build trust among stakeholders.

Q8: If you could change one thing about how organizations approach privacy today, what would it be and why?

I would change the perspective from viewing “privacy as compliance” to seeing “privacy as strategy.” Privacy doesn’t have to be a boat anchor. Privacy is about common sense. Privacy is nothing more than good information management and good customer service. When organizations integrate privacy with trust, innovation, and brand value, compliance occurs naturally and a culture of accountability becomes self-sustaining.

_____________________________

If you enjoyed this interview series, please follow Patrick. He is a healthcare privacy expert and has helped organizations build privacy and security programs.


P.S Is privacy a top concern when implementing AI?

Have you tried asking ChatGPT abt yourself?

Try it. I hope you don’t find sensitive information.

AI models feed on data. And yet so many organizations have headed straight for the AI gravy train without due consideration for the impact on data management and privacy. 

I interviewed my friend Patrick Lo, the CEO of Privacy Horizon, who helps his clients make sense of the ever-changing landscape of privacy and the impact of AI.

The Intersection of Privacy and AI

Q5: As AI becomes more embedded in diagnostics and digital health tools, where do you see the biggest privacy blind spots emerging?

Many organizations that adopt AI often overlook the importance of a solid AI Governance Framework. This oversight can lead to unsupervised AI being used within the organization, allowing users to leverage AI solutions without proper guidance. Such a lack of direction often leads to unintended disclosures of sensitive information. Additionally, a significant blind spot exists where many organizations are unaware of what personal or health data their AI models are accessing, retaining, or inferring. 


Q6: How is Privacy Horizon adapting its services — for instance, with AI-PIAs or automated privacy assessments — to address these new challenges?

We’ve expanded our service model to include AI Privacy Impact Assessments, AI Governance Frameworks, AI Training, and readiness tools aligned with the EU AI Act and ISO 42001. These help healthcare organizations assess AI systems’ risks, ensure transparency, and demonstrate trustworthy AI adoption.
_____________________________

If you enjoyed this interview series, please follow Patrick. He is a healthcare privacy expert and has helped organizations build privacy and security programs.


P.S What worries you about AI and privacy?

10 planning considerations for a live red team exercise.

A live Red Team exercise can transform your organization’s cyber readiness.

Or it can blow up in your face.

Most companies underestimate the planning required. 
Live exercises introduce operational risk, reputational exposure, and real technical consequences if poorly scoped.

Here are 10 planning considerations. 

⸻

1. Define crystal-clear objectives before touching the scenario.

A Red Team exercise easily derails without a defined purpose.
•	Are you testing detection?
•	Decision-making?
•	Business response?

Knowing the objective helps guide the red team and enables alignment.  

⸻

2. Assess organizational maturity honestly before selecting tactics.

Live exercises should match capability.
Teams still struggling with escalation protocols shouldn’t jump straight to advanced APT emulation.
Ensure your IRP, SOC workflows, and communication playbooks are mature enough to withstand live pressure.

⸻

3. Secure executive sponsorship and socialization early.

Leadership must know what they’re approving. This includes scope, risks, expected disruptions, and reporting cadence.

⸻

4. Establish strict scope, boundaries, and rules of engagement.

A Red Team must know exactly what is allowed.
Examples:
•	No production data exfiltration.
•	No destructive actions.
•	Limited hours for intrusion.
•	Clear ‘stop game’ conditions.

Defined ROE protects your systems, your people, and your reputation.

⸻

5. Map out all critical systems, dependencies, and crown jewels.

You can’t test everything.
Choose what matters most:
•	Mission-critical applications
•	Identity systems
•	Cloud environments
•	OT/ICS (very rare)

Have a clear reason why this is the target. 

⸻

6. Involve key third-party vendors before game day.

Many Red Team exercises collapse due to vendor bottlenecks.

Notify them early. 

Their tools, logging, and escalation capabilities determine how realistic and valuable the exercise becomes.

⸻

7. Prepare the SOC and security teams without revealing the scenario.

Let them know the exercise window and who to clarify with if there are doubts. 

A Red Team exercise shouldn’t overly hamper operations. Yes there will be increased load for short periods of time. 

⸻

8. Decide the battle rhythm for decision-making and communication.

Synchronisation avoids chaos and ensures realism in response flow.

Also include exercise control meetings to keep teams updated. 

⸻

9. Create a safety plan.

Live operations = live risk.

A safety plan ensures the Red Team can push boundaries without endangering the business.

⸻

10. Design a mature debrief, learning review, and AAR process.

The biggest ROI comes after the exercise.

A rigorous debrief is where transformation happens.

⸻

Conclusion

A live Red Team exercise is a meticulously planned, high-stakes enterprise learning event.

Plan it properly, and you elevate your team’s resilience.
Rush it, and you erode trust in security

taplio

The Battle

Dickie Bush 🚢

Lester Chng

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taplio

The Battle

Dickie Bush 🚢

Lester Chng

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Dickie Bush 🚢's LinkedIn Performance

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Performance ScoreDickie Bush 🚢's LinkedIn Performance