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.

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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.

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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

I lost my voice on many occasions.  
 
But LinkedIn helped me find it again. 
 
I lost my voice when I left the Navy. 
12 years in service.  
It remains a part of me. 
Naval terms. Military speak.  
Barking orders and receiving them. 
 
And then I left the Navy.  
 
I lost my voice when I left the country. 
34 years in the land. 
I will always belong there. 
Singlish, slang, and all I knew. 
Culture, habits, being a local. 
 
And then I left the country. 
 
I lost my voice when I began abroad. 
8 years since I landed. 
I wonder if I'll ever belong. 
New nuances, new circumstances. 
 
And then I began again. 
 
I lost my voice when I lost my job. 
I will never forget the letter. 
"Changing business requirements" 
I told myself this will never be a chore. 
 
And then I found my voice. 
 
You may find this platform a bore. 
"I need a job" 
"I am excited to...." 
"🚀🚀🚀🚀🤖🤖🤖🤖" 
"Are you interested in buying.." 
 
But it has allowed me to find my voice. 
 
Cause one day, I may lose it again. 
 
Have you lost your voice before?
What steps are u taking to mitigate?

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Running naval wargames and designing cyber exercises at a bank are more similar than people expect.

It did help that the big boss at the bank was a former naval aviator. 

He knew with a fusion centre structure of managing security incidents across cyber, fraud, physical security, and crisis management, the teams needed a robust training program to drive operational excellence and achieve full operating capabilities. 

That was the first task. 

Get back to basics. 
Sort out the procedures. 
Drill the response teams. 

Do you run drills for your teams?

Or assume they will respond to your expectations?

You know Canada is on the up when Dad sends you a TikTok (no i dont have an account) about the upcoming increase in defence spending.

What about Canada do you appreciate?

I like the cold...... what about you?

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bootcamp

Sign up here:
https://catalystcorporatetraining.classe365.com/form/view/AutoBootCamp?_gl=1*9rfqtg*_ga*MTQ4NTczNDM0MC4xNjk4MjQxODM1*_ga_YYXBQS6S5Q*MTcwNzgzMzEyNi4xODEuMS4xNzA3ODMzMTYwLjI2LjAuMA

Building a cyber company is not for everyone.

Do you even have the commitment to do so?

I interviewed Eldon Sprickerhoff to get his insights for the next generation of founders. He is an Entrepreneur-in-Residence and a mentor at Rogers Cybersecure Catalyst, Toronto Metropolitan University. 


𝗧𝗵𝗲 𝗰𝘂𝗿𝗿𝗲𝗻𝘁 𝗰𝗵𝗮𝗽𝘁𝗲𝗿. 𝗦𝘁𝗶𝗹𝗹 “𝗖𝗼𝗺𝗺𝗶𝘁𝘁𝗲𝗱”

𝘘: 𝘞𝘩𝘢𝘵 𝘵𝘩𝘦𝘮𝘦𝘴 𝘰𝘳 𝘤𝘩𝘢𝘭𝘭𝘦𝘯𝘨𝘦𝘴 𝘬𝘦𝘱𝘵 𝘴𝘩𝘰𝘸𝘪𝘯𝘨 𝘶𝘱 𝘪𝘯 𝘤𝘰𝘯𝘷𝘦𝘳𝘴𝘢𝘵𝘪𝘰𝘯𝘴 𝘸𝘪𝘵𝘩 𝘧𝘰𝘶𝘯𝘥𝘦𝘳𝘴 𝘵𝘩𝘢𝘵 𝘶𝘭𝘵𝘪𝘮𝘢𝘵𝘦𝘭𝘺 𝘭𝘦𝘥 𝘺𝘰𝘶 𝘵𝘰 𝘸𝘳𝘪𝘵𝘦 𝘊𝘰𝘮𝘮𝘪𝘵𝘵𝘦𝘥 𝘢𝘯𝘥 𝘤𝘳𝘦𝘢𝘵𝘦 𝘵𝘩𝘦 𝘮𝘢𝘴𝘵𝘦𝘳𝘤𝘭𝘢𝘴𝘴?


I kept seeing the same patterns: some passionate and brilliant technical founders hitting predictable walls - raising capital without understanding dilution consequences, scaling teams without proper foundations, pursuing growth without sustainable unit economics, or worse: flailing in the market with a product/offering that didn’t have an obvious value or importance.

What frustrated me was that these weren't unsolvable problems. They were challenges we had faced and eventually figured out, often painfully. I realized this knowledge could help others avoid the same expensive mistakes.

The recurring theme was the gap between technical excellence and business fundamentals. Founders could build incredible technology but struggled with identifying their true “ideal client profile”, minimally viable offering, go-to-market strategy, fundraising dynamics, or organizational design. "Committed" became my way of sharing survival strategies that weren't readily available elsewhere.


𝘘: 𝘞𝘩𝘢𝘵 𝘢𝘳𝘦 𝘺𝘰𝘶 𝘮𝘰𝘴𝘵 𝘪𝘯𝘵𝘦𝘳𝘦𝘴𝘵𝘦𝘥 𝘪𝘯 𝘸𝘰𝘳𝘬𝘪𝘯𝘨 𝘰𝘯 𝘰𝘳 𝘤𝘰𝘯𝘵𝘳𝘪𝘣𝘶𝘵𝘪𝘯𝘨 𝘵𝘰 𝘳𝘪𝘨𝘩𝘵 𝘯𝘰𝘸, 𝘢𝘯𝘥 𝘩𝘰𝘸 𝘥𝘰𝘦𝘴 𝘵𝘩𝘦 𝘮𝘢𝘴𝘵𝘦𝘳𝘤𝘭𝘢𝘴𝘴 𝘧𝘪𝘵 𝘪𝘯𝘵𝘰 𝘵𝘩𝘢𝘵 𝘧𝘰𝘤𝘶𝘴?

Right now, I'm focused on helping the next generation of cybersecurity founders build enduring companies. Through my consulting and advisory roles, I'm seeing exceptional technical talent that needs guidance on the business side.

The masterclass is a way to scale that impact. I can only mentor a handful of founders directly, but the principles I learned building eSentire are broadly applicable. I want to help founders avoid the mistakes that nearly killed our company early on and accelerate their path to product-market fit and sustainable growth.

What excites me most is seeing founders take these lessons and apply them in ways I never imagined - solving problems that didn't exist when we started eSentire. The cybersecurity landscape keeps evolving, and I want to help the best founders navigate it successfully.


If you enjoyed this interview series, please follow Eldon and get his book at https://lnkd.in/gS2HNAnY


P.S. Have you read Committed? 
Get it already.

Dear LinkedIn,
Here is what it is like using the app. 

Suggested

Suggested

Suggested

Sponsored

Suggested

Sponsored 

Suggested

Sponsored


What’s up with this feed?

Did you even consider the experience?

Pls bring my connections’ posts. 

Sincerely,
Everyone.

LinkedIn

It is RSAC in a couple of weeks. 
Yet your meeting calendar is scarily empty.

Your VP Marketing has been urging you to post more on LinkedIn during the lead-up to RSAC.

But is has been crazy busy with client demos, contract negotiations, partner agreements, manpower turnover, investor updates, fund-raising, and just LIFE.

The start of the year flew by and you didn't realize RSAC is just around the corner. The conference that costs a pretty penny but you don't feel like you have good momentum going into the event.

Your last LinkedIn post was a report of a company announcement 3 weeks ago. Your DMs are all full of spam. And you ignored your VP Marketing's email to post more.

But where do you start? What do you post about?

I have 2 resources for you.
1. The Cybersecurity CEO’s Personal Brand Blueprint
2. 5 LinkedIn Posts Templates for Cyber CEOs

You have 1 week to catch up.

Don't waste another year at RSAC.

DM or comment "RSAC" and I'll send you both.

When I first moved to Canada, I remember reading about their Navy and Air Force capabilities (don’t ask me why I didn’t bother abt the Army). 

12 Halifax frigates. Ageing, 1990s
4 Victoria subs. Second hand. 
6 OPVs. Still coming online. 
12 Patrol crafts. 

F18s - started from 1982….


And to defend coast to coast….
to the True North

Was an impossible task. 

This Defence budget and Strategy is long overdue and may be the silver lining in this rocky new world. 

We are all pulling in the same direction. 

Rogers Cybersecure Catalyst, Toronto Metropolitan University will offer every company in every Catalyst program strategic insights to help them explore and pursue opportunities in Canada’s growing defence sector.

Stay connected and pull together.

Rogers Cybersecure Catalyst, Toronto Metropolitan University

The reason your posts fall flat? 
They read like press releases.

Most posts I see on LinkedIn read like they were written by a corporate communications team.

They’re clean. Safe. 
Approved by six people.
And boring as hell. 

Here are a few lessons that I gained after writing >1000+ posts. 
⸻

Lesson 1: Write as you would speak. 
You don’t need big words or long sentences.
Short. Direct. Clear.
If you wouldn’t say it in a conversation, don’t write it in a post.

⸻

Lesson 2: Share what it means, not just what happened.
Describe what you learned from it.
What changed for you? 
For your clients?
That’s the part people care about.

⸻

Lesson 3: Write to one person.
Think of someone specific — a client, a peer, a younger version of yourself.
Write as if you’re speaking to them.
That’s what makes people stop scrolling.

⸻

LinkedIn isn’t a press room.
It’s a coffee chat. 

Incorporate these lessons and the posts will start landing.

Whose posts do you enjoy reading?

Sick of tabletop exercises?

Here are other training tools to use. 

Picture this. 
You designed and planned for your tabletop exercise for months. 

The date is decided and you sent out the calendar hold. 

“Urghh”. The synchronized groans echo across the office space. 


Johnny Smarty Pants: “I bet it’s an AI or ransomware scenario again”. 

Jimmy Old Timer: “Time to dust off the old playbook”. 


How do you think the exercise will go?
Probably the same as the last 5..

Even MSPs know that this is a problem. 
“Our clients are bored of TTXs”.


Here’s how to shake things up. 

1. Use short drills instead
2. Execute unalerted exercises
3. Ask delegates to be the primary 
4. Allocate budget for a simulation ex

You can and should incorporate some variety and creativity in your training. 

Otherwise it’s a bloody snooze fest. 

Everyone know it and just goes through the motion at your tabletop. 

Depressing stuff. 

P.S any other bright training ideas?

4 types of people in tabletop exercises.

And how to deal with them.

It is every facilitator's nightmare. You spend hours designing and scheduling a tabletop exercise and you practice and envision every conversation, pushback, scenario.

Yet you still feel unprepared because you don't fully know who the audience is, what they are like, and whether they will chew you up and spit you out.

Here are the 4 archetypes and how to manage these characters.

1. The Know-it-all

If we all conduct a blind survey in the room and ask everyone to close their eyes and point to the person who "Knows-it-all", they will all point to the same person.

How to tell who this person is?

Don't worry. When the exercise reaches the first discussion point, this person will start talking about Step A to Z on what he or his team will do. He knows his plans, critical processes, who to call, what to ask, what to investigate, how long it takes, priorities etc

How do you handle the "Know-it-all"?

This is a good thing.
Don't discourage the sharing. Instead leverage what the person is sharing and post some of the things he raised to other teams.

Example:
Know-it-all: For this particular incident, we will triage and send out the initial report within 30 mins

You: That is excellent. Operations team (or any other team that should receive the report), is the information within the initial report sufficient or what other types of info will help your team's processes?

Know-it-alls are good for keeping the flow of the exercise. Leverage them well.

2. The Forever-Skeptic (FS for short)

Signs of the FS.
- This will never happen
- We have implemented tools for this
- This inject is not applicable for our env

I know. 
You may find yourself sweating at this point. But don't worry, leverage your exercise design partner to help expand on the inject to make it relevant.

OR if all else fails. 
This is one trick that works.

Ask the FS straight up. 
"Is there a similar inject or scenario where in your experience and expertise, you know will triggers an event/incident that needs your team's response?"

1. This strokes FS's ego.
2. You have trapped FS. He can't say there is no such scenario.
3. Smile and pivot from FS's suggestion.
4. Rem to tie it back to the overall scenario.

3. The Conversation Hogger

Signs of the Hogger
- This is a no brainer. If you record the whole, the hogger probably took up 70% of the air time.

It is likely that the hogger has gone too far down a rabbit hole. 

Acknowledge the hogger's contribution and bring others in the convo.

4. The silent ones

No sound. No inputs. No involvement.
Ask them directly what they think or they would do. 
Do it with every inject.

What other characters are there and how do you deal w them?

LinkedIn  isn’t rocket science. 
10 things you can do today that will take less than 1 min. 

Forget the polished profile. 
Funnel content tactics. 
Funky AI graphics. 

Keep it simple. 

Do one of these (or all) and make LinkedIn work for you. 

1. Send a DM to refer someone
2. Send a DM to encourage someone
3. Comment on a stranger’s post
4. Reconnect w an ex colleague
5. Congratulate an achievement
6. Say hi to a stranger in your field
7. Say hi to a stranger not in your field
8. Ask for insights from an expert
9. Ask someone for that referral
10. Ask someone if they need help

Try it out. 
Let me know how many you hit today.

P.S when was the last time you did any of the above?

Running the Naval Wargaming & Simulation Centre provided a strong foundation for running cyber exercises.

Here was what a typical week looked like.

• detailing injects
• designing exercise scenarios
• preparing exercise with instructors
• running exercises for warfare teams
• keeping up to date with naval tactics
• tracking and assessing performances
• planning out future exercise schedules
• conducting pre and post-exercise briefs
• discussing the ship's exercise objectives
• ensuring teams are up to date on Red Team tactics

Now you can understand the transferable skills in Cybersecurity exercises.

It’s 2026 and it’s still a VUCA world. 

Volatilite
Uncertain
Complex
Ambiguous 

No wonder there is a continued demand for crisis mgmt professionals. 

VUCA was introduced in 90s to describe the post Cold War period. 
Still as relevant today. 


In fact, things may escalate. 

BANI is added to the frame with pandemics, AI, and whatever’s next. 

Brittle
Anxious
Nonlinear 
Incomprehensible


Stay safe out there. 

P.S Just saw the missile attack on the base in Bahrain where I was stationed back in the day.

Building a product isn’t the hardest part for cyber founders. 

It’s building trust. 

- Enterprise buyers make a decision about a founder before they ever get on a call. 

- Investors decide whether to respond to your email based on what they find when they search your name. 

-Partners size you up against competitors who’ve been showing up publicly for years.

You can have the best product in the market and still lose the deal to someone with an inferior solution and a stronger presence.

Trust is built before the conversation starts and your presence on LinkedIn shouldn’t be overlooked.  

What does your LinkedIn say about you to someone who’s never heard of your company?

Imagine exercising the exact scenario a couple of weeks before an incident. 

This is how some teams would have managed the lead up to this weekend. 

The sharpest teams would have tracked the escalation and highlighted the threat scenarios weeks ago. This can only happen if your threat intel teams covers beyond just cyber. 

The risk teams would be pulled in and have a quick reassessment. This can only happen if your intel and risk teams know how to work together. 

The exercise and security teams collaborate to rapidly design and develop exercise scenarios. This can only happen if leaders carve out time. 

The leadership team prepare briefs to the executive leadership and board. This can only happen if there is trust. 

Can you predict when something kicks off? Nope but you can certainly prep for it in advance. 

And when you run the exact scenario weeks before it actually happens. 

Imagine the credibility your team gains. This doesn’t happen by chance but by an intricate and established machinery. 

P.S 
how are you actively managing risks?

If the message is still unclear, do this. 
- review last few major incidents 
- identify the most relevant scenarios
- refresh or recirculate response plans
- stand up a quick incident drill 
- plan for a near term exercise 
- run the exercise and note lessons
- update leadership on readiness


Write a quick doc on this process. 
That is your response playbook. 
Don’t fumble the next crisis.

Cybersecurity marketing truth:

Conference booth: $40,000 for 72 hours of exposure
LinkedIn: $0 for year-round client acquisition

Let me explain why this matters:

The math simply doesn't add up anymore.

That $40K RSAC booth gets you:
- A week of fighting for attention
- Hundreds of scanned badges (most whom will never respond)
- A team of exhausted sales reps
- Maybe 2-3 qualified opportunities if you're lucky

Meanwhile, the most successful cybersecurity leaders I work with are building personal brands on LinkedIn that generate:
- Continuous inbound leads
- Speaking invitations
- Media opportunities
- Partnerships
- Investor interest
- And yes, actual customers

The key difference? 
Trade shows are transactional. 
LinkedIn is relational.

Here's what a strategic LinkedIn approach for cybersecurity leaders looks like:

𝟭. 𝗙𝗼𝗰𝘂𝘀 𝗼𝗻 𝗮 𝘀𝗽𝗲𝗰𝗶𝗳𝗶𝗰 𝘀𝗲𝗰𝘂𝗿𝗶𝘁𝘆 𝗱𝗼𝗺𝗮𝗶𝗻
Don't try to be everything to everyone. Are you an identity expert? Cloud security specialist? OT security veteran? Pick your lane and own it.

𝟮. 𝗦𝗵𝗮𝗿𝗲 𝘆𝗼𝘂𝗿 𝗼𝗽𝗲𝗿𝗮𝘁𝗶𝗼𝗻𝗮𝗹 𝗸𝗻𝗼𝘄𝗹𝗲𝗱𝗴𝗲
CISOs don't need another vendor telling them breaches are bad. They need practical insights from someone who's been in the trenches.

𝟯. 𝗛𝘂𝗺𝗮𝗻𝗶𝘇𝗲 𝘀𝗲𝗰𝘂𝗿𝗶𝘁𝘆 𝗰𝗵𝗮𝗹𝗹𝗲𝗻𝗴𝗲𝘀
Most security content feels like it was written by robots for robots. Talk about the human elements - the stress, the politics, the wins.

𝟰. 𝗗𝗼𝗰𝘂𝗺𝗲𝗻𝘁 𝘆𝗼𝘂𝗿 𝗷𝗼𝘂𝗿𝗻𝗲𝘆
Building or selling security solutions is hard. Share your progress, setbacks, and lessons. Vulnerability builds trust.

𝟱. 𝗘𝗻𝗴𝗮𝗴𝗲 𝗰𝗼𝗻𝘀𝗶𝘀𝘁𝗲𝗻𝘁𝗹𝘆
This isn't about posting once a month. It's about showing up regularly to add value to industry conversations.

The cybersecurity industry has a trust problem. Your LinkedIn presence helps solve that by building relationships before the sales pitch.

Is a LinkedIn-first approach right for every security company? No.

But if you're spending $200K+ annually on trade shows without a personal brand strategy, you're leaving opportunities on the table.

What's your experience with cybersecurity marketing? Is LinkedIn working for you or is the trade show circuit still your primary channel?


P.S who has the best pre-RSAC game?

It’s RSAC week and if you are the Head of Marketing and your CEO only makes 1 "I’m going to RSAC" post. 

U know u have missed an opportunity. 

An opportunity to raise awareness. 
An opportunity to warm up leads. 
An opportunity to stand out. 

Now all you can do is pray that the thousands that walk by your booth will be pulled in by the free tshirt. 

And spend 45 seconds giving yr marketing reps a slight nod every once in a while, with a sheepish smile. 
And a thank you. Before scurrying away with their prize in hand. 

You’ll never hear from them again. 

Hated reading that?

While it may be slightly late to "build authority", at least try to raise awareness for your organization with a last minute 5-post sequence.

Drop me a DM, I'll send you:
1. The Cybersecurity CEO’s Personal Brand Blueprint
2. 5 LinkedIn Posts Templates for Cyber CEOs


Stay safe.

Here is what Cyber CEOs should post on LinkedIn. Save this for ideas.  

Most Cyber CEOs only repost their company's content.
Or share updates about the latest hacks. Or they post random AI blogs.

But here's the thing:

- Those posts are generic.
- They don't stand out.
- They don't show leadership.

You are the leader. Lead by example.

Share customer success stories.
Talk about business lessons. 
Have a contrarian viewpoint. 

This is how you can stand out:

→ Highlight customer success stories.
Share real examples of how your company helped clients.
It builds trust and showcases your value.

→ Discuss lessons learned.
Talk about your experiences and what you’ve learned.
It shows you are growing and learning.

→ Voice strong opinions.
Take a stand on industry issues.
It positions you as a thought leader.

By doing this, you'll not just be another CEO. You'll position as aa leader who leads by example.

Make those posts count. 

Here are 26 types to choose from.

Type 1: Authority Posts
Examples:
Deep dive into project implementation
Demonstration of expertise
Client transformation
Knowledge sharing
Client testimonial
Opinions
Insights
Trends

Type 2: Personal Posts
Vision for company
Vision for products
Lessons learned
Founder stories
Team culture
Challenges
Leadership
Resilience
Wins

Type 3: Trust Posts
Highlight value proposition
Talk about problems solved
Demonstrate solutions
Customer pain points
Decision making 
Social proof
Principles
Results
Values

5 things Cyber CEOs do on LinkedIn that harms their brand and rep. 

Before you dismiss it as trivial, your prospects, clients, partners have and will take a glance at your profile. 

How will you show up in their snapshot assessment? Can you risk of they form an early impression?

1. Empty Profile

This may be acceptable in 2010. 
It will raise more questions than answers and you don’t want that. 

2. Unprofessional Pic and Banner

If you don’t accept a shoddy website, why would you accept an unpolished profile?

3. Boring copy across page 

From your headline to your about section and even your outdated experience page. 

If it screams a lack of attention and effort, doesn’t really move the needle forward does it?

4. Effortless content

Repost, repost, repost, repost

And you wonder why this platform sucks. 


5. Full on AI Bonanza

We have all seen it. 
Posts with more fluff than insights. 
Comments that don’t make sense. 
Spam DMs that lead to being reported. 

This is a straight road to being banned.  



When was the last time you audited your profile and campaign?

P.S what else are folks doing wrong here?

I spent years simulating attacks and training naval warfare teams. 

Wargaming and simulation to hone tactical nuance, command and control, and making decisions under pressure.  

These played out in a simulation centre so that when the teams are out at sea, they have the confidence and clarity in execution. 

It is not so much different to readiness in cyber incident response. 

I started building and running tabletop exercises and cyber range simulations for banks, regulators, manufacturers, ministries. 

Same discipline, different domain. 

Subject teams to pressure and guide how they handle it. 

What I kept noticing had nothing to do with firewalls or detection tools. It was about who could communicate clearly when the pressure builds. 

Who could look at a chaotic situation and build a clear picture of what was happening, what it meant, and what needed to happen next.

The technical teams usually understood the problem. The ones who succeeded were the ones who could explain it to everyone else in the room.

What are some horror stories you have seen during incident response and exercises?

Former GE Capital Executive | I help founders and executives see what their financials aren’t telling them.

I spent 25 years inside the machine.

GE Capital. GE Vernova. NBCUniversal. Unilever. Structured finance, capital markets, project finance across Latin America. I was the CFO who sat across from banks, governments, and Fortune 500 boards and made the numbers make sense. I closed an $800 million power plant deal. I managed capital market teams and hundred-million-dollar sales budgets. I built financial models that moved real money in real markets.

I was good at it. For a long time, that was enough.

Then it wasn't.

I stayed almost eight years past the moment I knew I was done. Eight years of golden handcuffs, institutional momentum, and not having a single person in my corner who could help me think through what leaving actually looked like -- financially, strategically, personally.

When I finally left, I made mistakes. I jumped into a startup that looked great on paper and had no financial foundation underneath it. I learned the hard way that passion without financial intelligence is just expensive optimism. Then I spent hundreds of thousands of dollars learning the things corporate never taught me -- how to sell, how to communicate with conviction, how to walk into a room and make people feel what I knew to be true about their business.

That education nearly broke me. And it turned me into something rare: a former Fortune 500 CFO who can read your financials like a surgeon reads an MRI and sit across from you like a partner who actually gives a damn.

That's what I do now.

I work with a small number of founders and executives -- people who've already built something substantial and want a strategic partner with real financial depth. Not a coach. Not a consultant recycling frameworks. Not a bookkeeper calling themselves a fractional CFO. Someone who's been in the rooms, closed the deals, read the balance sheets, and came out the other side with a clear point of view about what actually matters.

If you're a founder past $1M who can feel that the way you got here won't get you to the next level, I can show you exactly where the growth is hiding and where the model breaks.

If you're an executive who knows you're meant for something bigger than the title on your business card, I've been where you are. I made the leap. I can help you think through yours.

I don't work with everyone. I'm selective about who I take on because the work only works when both sides are all in.

One conversation is all it takes to know if we're the right fit.

Cruz Gamboa

Most founders don’t go bankrupt overnight.

They bleed slowly.
From numbers they refused to look at.

Revenue looks good.
Growth feels exciting.
Ego feels validated.

But:

➡️ Cash flow is tight
➡️ Margins are thin
➡️ One client controls everything
➡️ Burn rate is “we’ll figure it out”

That’s how businesses die.

Not from lack of ambition.
From lack of financial discipline.

Here’s the cheat sheet I wish every founder read earlier.

Ignore red flags early → pay the price later.

If you want to find your biggest 1% opportunities,
check out scalingcfo.io

Free assessment.

If this helped, save it.

Your P&L Is Hiding the Real Problem.

Most founders check 3 things:

Revenue.
Profit.
Growth rate.

Then they relax.

That’s the mistake.

Because your P&L is a scoreboard.

Not a diagnosis.

And scoreboards don’t tell you why you’re winning,
or why you’re about to lose.

Here’s what it’s not showing you 👇

If revenue is growing but cash is tight…

You don’t have a profit problem.
You have a cash flow problem.

If sales are strong but margins are shrinking…

You don’t have a demand problem.
You have a pricing or delivery problem.

If profit exists but stress keeps increasing…

You don’t have a money problem.
You have an operational problem.

Most businesses don’t collapse overnight.

They erode slowly:

➡️ Slightly rising CAC
➡️ Slightly lower margins
➡️ Slightly higher payroll
➡️ Slightly longer collections

Small leaks.

Compounded monthly.

And because the P&L still “looks fine,”
no one panics.

Until they should have.

Here’s what real operators track:

✓ Gross margin trends
✓ Cash runway (in months) 
✓ Revenue per employee
✓ CAC payback period
✓ Churn rate

Those numbers tell you where the fire is starting.

Revenue is vanity.
Profit is sanity.
Cash flow is survival.

Read your P&L.

But interrogate it harder.

Because the businesses that scale aren’t the ones with the best revenue.

They’re the ones who catch problems before they show up on the bottom line.

Your financial reports are perfect.

Clean P&L.
Accurate balance sheet.
Cash flow that ties out.

Yet decisions still feel slow, reactive, or unclear.

That’s because reports don’t create leverage.
Interpretation does.

Most founders read numbers like history.
High-performing operators read them like instructions.

Every metric should force a decision:
→ double down
→ fix fast
→ kill it

If nothing changes after reviewing your numbers,
you didn’t review them, you admired them.

This cheat sheet breaks down:

➡️ The questions that actually matter
➡️ The metrics that lie
➡️ And how to spot 1% changes that unlock outsized results

Save this before your next finance review.

cruzgamboadrive

patagonia-solar-llc

This guy bought one random car dealership.
Turned it into a $5B empire.

No fancy startup.
No venture capital.

Just one smart business move.

Terry Taylor started like most people in the auto industry:

Working inside dealerships.

Climbing the ladder.

But he realized something important:

No matter how hard you work…
You’re still building someone else’s business.

So in 1982, he bought his first dealership in Daytona Beach.

Most people would stop there.

He didn’t.

But the real genius wasn’t buying more dealerships.

It was how he structured them.

Instead of hiring managers, he:

• Gave them 20–25% equity
• Helped finance their buy-in
• Let them run the store

Now managers weren’t employees.

They were owners.

And owners think differently.

They protect profits.
They grow the business.
They care about reputation.

So scaling became easy.

1 dealership → 10 → 50 → 120+ dealerships

Today the network does $5B+ in revenue.

Simple lesson:

People work harder for ownership than salaries.

Build partners.
Not employees

If you want to find your biggest 1% opportunities,
check out scalingcfo.io

Free assessment.

If this helped, save it.

Terry Taylor

He spent 31 years running Trader Joe’s.
Mastered pricing. Supply chains. Consumer psychology.
But one thing bothered him more than anything else: food waste.

Every year, the U.S. throws away 120 billion pounds of perfectly good food.
Not unsafe. Just didn’t fit profit models.

Millions of families struggle to afford groceries.
Most CEOs see this as “business as usual.”
Doug saw it as broken design.

After retiring, he didn’t join a board. He didn’t consult.
He asked a different question:

💡 What if food waste became the foundation, not a byproduct?
What if access mattered more than margin?

✅ Daily Table is born.
✅ Grocery store built on surplus food.
✅ Affordable meals. Nutritious produce. Dignity first.
✅ No charity branding. No eligibility checks.
✅ Nonprofit by design. Every surplus reinvested in lowering prices.

Critics say it can’t scale. Doug agrees.
It wasn’t meant to dominate. It was meant to fix a failure everyone ignored.

From grocery CEO → noticing waste everywhere → building a store that feeds people, not profits.

If you want to rethink how systems work, look at incentives, not supply.
This is the anti-profit grocery model.

Daily Table

He was a waiter at Red Lobster.

He had $40.

Most people would complain. He built a $6B brand.

Here’s how:

✅ Saw a problem: kids in his neighborhood paying too much for hats.

✅ Took action: taught himself to sew, made hats at home.

✅ Scaled smart: sold locally → hip-hop stars wore FUBU → national attention.

✅ Got creative: turned his living room into a factory, raised money when banks said NO.

✅ Played the long game: built FUBU → became Shark Tank investor → mentors hundreds of startups.

Most people chase attention.
He chased problems that matter.

Critics said it wouldn’t work. He did it anyway.

You don’t need permission. You don’t need hype.
You need clarity, hustle, and persistence.

From $40 → living room hustle → global empire → Shark Tank.
That’s how legends are built

If you want to find your biggest 1% opportunities, check out scalingcfo.io

Free assessment.
If this helped, save it.

Daymond John

Most people think billion-dollar companies start with experts.

Crumbl Cookies started with two tech guys who had never baked a cookie.

In 2017, they noticed something simple:
Cookies were America’s favorite dessert, but the category hadn’t evolved.
So they focused on a few key moves:

▶ Perfected one cookie first
▶ Kept the menu simple (1 classic + 4 rotating flavors)
▶ Turned weekly flavor drops into social media events

That simple strategy turned a 900 sq ft store and $10K into

✅ 800+ locations
✅ 1M cookies sold daily
✅ $1B+ valuation

They didn’t win by doing more.
They won by focusing on the few decisions that drive everything.

That’s true in finance too.

If you want to find your biggest 1% opportunities, go to scalingcfo.io
Take the free assessments and see exactly where to focus first.

Crumbl Cookies

Some people launch snacks.
Some create global empires from leftovers.

Arch West did the second.

➡️ 1960s. Disneyland.

Casa de Fritos. Tons of stale tortillas. Wasted daily.
A small vendor saw opportunity.
“Cut them into triangles. Fry them. Add some seasoning.”

No PR. No hype. No flashy launch.

Just execution.
Just obsession.
Just seeing value where others saw trash.

1966 → Plain Doritos, national launch.
1972 → Nacho Cheese.
From leftover tortillas → multibillion-dollar snack empire.

Scaling lesson:

Opportunities are everywhere. Most ignore them.
Those who see the leverage, execute relentlessly, and scale turn accidents into legends.

Some people chase attention.
Some quietly turn scraps into billions.

#scalingup #ceo #founder #businesslessons

Doritos

$30,000 → $7 BILLION.
No hype. No fluff. Just strategy.

Dennis Washington was 30, broke, and borrowing $30k from a Caterpillar dealer.

He bought one bulldozer and started doing construction in Montana.

Within 5 years? He was the largest contractor in the state.

But he didn’t stop there.

He asked a simple question:
"Where is everyone running from?"

Then he built a formula:

✅ Buy failing businesses that everyone else ignores.
✅ Fix the basics cut costs, improve management, unlock cash flow.
✅ Use the profits to buy the next one.
✅ Repeat.

First test: a worthless copper mine.
Bought for $15M → $100M profits in 3 years.

Next: a struggling global construction firm, merged it → Washington Group International → sold for $2.6B.

Now? Real estate, aviation, railroads, marine services… a $7B empire all from turning broken things into cash.

Most people run from broken businesses. Dennis Washington built a $7B empire fixing them.

If you want to find your biggest 1% opportunities, check out scalingcfo.io

Free assessment.
If this helped, save it.

Dennis Washington

He had nothing.
No friends. Barely spoke English. ADHD made school unbearable.

At 16, he dropped out. Taught himself to code. Became obsessed with modifying video games.

At 22, he moved to Canada. New country. No network. Just a laptop and a love for snowboarding.

Started an online snowboard store → it failed.

But the software he built to run it? People wanted it.

💡 Lightbulb moment: Forget snowboards. Sell the software.

✅ Shopify is born.
✅ Made e-commerce simple.
✅ Millions of stores. 175 countries. Even Amazon switched.

From high school dropout → coding every week → building the internet’s mall worth $147B.

If you want to find your biggest 1% opportunities, check out scalingcfo.io
Free assessment.
If this helped, save it.

TOBIAS LÜTKE

Most “profitable” companies are one bad month away from dying.

Here’s why.

Profit is an opinion.
Cash is oxygen.

You can look profitable on paper and still miss payroll.
I’ve seen businesses doing 7 figures collapse because one client paid late.

Revenue doesn’t matter if:

• It’s delayed
• It’s unpredictable
• It’s already spent in your head

Growth makes this worse.

You hire early.
Lock in fixed costs.
Sign long-term tools.
Upgrade lifestyle.

Now your burn is permanent…
…but your income isn’t.

That’s the trap.

Another hard truth:
If the founder steps away and sales stop, you don’t have a business.
You have a high-stress job with employees.

Margins won’t save you.
Busy won’t save you.
Brand won’t save you.

Only cash flow will.

Simple rules that keep companies alive:

• Collect faster than you spend
• Keep fixed costs boring
• Build 3–6 months of runway
• Systems before scaling
• Liquidity before vanity growth

The strongest businesses aren’t the loudest.

They’re the ones that can survive a bad month without panicking.

That’s real leverage.

Peter Steinberger could have built “cool” software.

He didn’t.

He built useful software.

PDFs were everywhere. Developers were stuck with messy workflows. Peter asked:

What if developers had tools that just worked? That solved real problems, not just looked good on a portfolio?

✅ PSPDFKit → powers PDF apps across mobile & web.
✅ Open-source projects → simplify workflows, save engineers hours.
✅ OpenClaw → personal AI agent that actually helps you code.

Most people chase attention. Peter chases problems.

Critics say niche tools won’t scale. Peter doesn’t care.
He’s not in it for hype. He’s in it for impact.

From engineer → spotting friction everywhere → building tools that make developers’ lives better.

If you want to build something meaningful, solve real problems.
The market rewards results, not ideas.

If you want to find your biggest 1% opportunities, check out scalingcfo.io

Free assessment.
If this helped, save it.

Peter Steinberger

LVMH is worth $292.9 billion.

You're worth $10M and stressed about payroll.

Same industry. Completely different money game. Here's why.

I've sat inside dozens of $5M–$50M businesses as a fractional CFO.

The pattern never changes.

Founders confuse 3 separate problems:

❌ "We have a cash flow problem."

No. You have a timing problem. Revenue is fine. Your money is just in the wrong place at the wrong time. That's fixable in 90 days.

❌ "We have a scaling problem."

No. You tried to grow before your operations could hold the weight. Every single time. Growth didn't break you, the lack of systems did.

❌ "We have a fundraising problem."

No. Investors don't fund vision. They fund numbers that prove the vision is real. You don't have a pitch problem. You have a financial story problem.

Now look at the billion-dollar brands:

Inditex built Zara to $193B by selling inventory before the bill came due.

Hermès built $235B by turning scarcity into a balance sheet strategy.

Fast Retailing scaled Uniqlo globally because they built finance infrastructure first.

None of that is luck.
All of it is decisions, financial decisions dressed up as brand decisions.

The difference between them and you isn't capital.

It's that they stopped running on gut feel and built a machine that tells them exactly where every dollar is going, and why.

You don't need a $500K CFO on payroll.

You need 10 hours a month of the right financial brain in the room.

That's the actual arbitrage most $5M–$50M founders are sleeping on.

If your finances are running you instead of the other way around,

Comment "CFO" below and I'll show you exactly where to start.

Most founders don’t fail overnight.

They bleed slowly.
From decisions they ignored.
From processes they never set.
From metrics they refused to measure.

Revenue looks fine. Growth feels exciting. Ego feels validated.

But underneath:

➡️ Decisions get delayed → chaos spreads
➡️ Processes depend on you → hero culture burns out
➡️ Metrics are “nice to have” → guesswork rules
➡️ Accountability is optional → everyone points fingers

That’s how scaling dies.

Not from lack of ambition.
From lack of rules.

If you want to find your biggest 1% opportunities, check out scalingcfo.io

Free assessment.
If this helped, save it.
#scalingup #founders #ceo

Most people saw a ping pong table.

Max Koehler saw a business.

In 2019, he noticed something strange:

Table tennis is one of the most played sports in the world,
but in U.S. cities there were very few places to play regularly.

Most founders would open a traditional club.

Max built PingPod instead.

Small glass studios.
Open 24/7.
Booked entirely through an app.
No staff. No front desk.

But the real genius?

A camera above every table.

Every rally gets recorded.
One tap → instant replay → share on social.

Players created the content.
The content created the marketing.

Clips went viral.
Bookings exploded.

Today PingPod is valued around $40–60M.

All from one simple observation.

The best founders don’t just build products.
They build systems that grow themselves. 🚀

If you want to find your biggest 1% opportunities, go to
scalingcfo.io

Take the free assessments and see exactly where to focus first.

#scalingup #founders #CEO

Max Koehler

The trillion-dollar scoreboard isn’t just impressive.

It’s a warning. ⚠️

AI is no longer a feature.
It’s infrastructure.

Distribution beats product.
Platforms compress margins.
Specialisation scales faster than breadth.

And the giants NVIDIA, Microsoft, Alphabet, Amazon, Meta, Apple aren’t just companies anymore.

They’re rails.

If you’re a $1M–$10M founder, here’s the real play:

➡️ Build on top of giants, don’t compete with them.
➡️ Own your audience, don’t rent it.
➡️ Go narrow, dominate a micro-niche.
➡️ Push recurring revenue.
➡️ Move faster than anyone with a board meeting.

The economy is consolidating at the top.

But execution speed is still decentralised.

That’s your edge.

If you're building between $1–$10M and want to scale intelligently, not just aggressively

Come to the workshop → https://lnkd.in/efBiFQRg

I keep having the same conversation.

Founder calls me. Revenue is up -- sometimes way up. 

But they're taking home less than when the business was half the size. 

They hired the consultants. They wrote the plan. They pushed harder on sales. And somehow the business keeps snapping back to the same number like a rubber band.

After sitting across from enough of these founders, I started seeing the pattern. It comes down to three things nobody wants to talk about -- and none of them have anything to do with selling more.

I broke it all down in this week's newsletter.
#scalingup #founders #growth #CEO

I talk to a lot of founders. Like, a LOT. And something keeps coming up that I can't ignore anymore. Almost every conversation -- doesn't matter what 

Open article: The 3 things nobody tells you about getting stuck by Cruz Gamboa • 5 min read

The 3 things nobody tells you about getting stuck

99% of founders do this backwards.

They try to scale a business
that no one has proven they want.

Then they try to sell a business
that only works because they exist.

Here’s the real order:

1. Start
Don’t build the product.
Sell it first.

If no one pays, it’s not a business.
It’s a fantasy.

2. Scale
Do less. Better.
One offer. One audience. One channel.

Systemize everything.
If it needs you to survive, it’s not scalable.

3. Sell
Buyers don’t pay for hype.
They pay for predictable cash flow.

Clean books.
Recurring revenue.
Low founder dependency.

Start with proof.
Scale with systems.
Exit with leverage.

That’s how you build something that prints money, not something that prints stress.

If you want to find your biggest 1% opportunities,
check out scalingcfo.io

Free assessment.

If this helped, save it.

Most founders don’t have a growth problem.
They have a focus problem.

Their dashboards are full.
Their results are not.

Tracking more KPIs doesn’t make you smarter.

It just gives you more ways to avoid the hard decision.

Here’s how serious founders think about metrics:

If a number doesn’t change what you do this week,
it doesn’t belong on your dashboard.

That’s why the only startup metrics that actually matter answer 4 questions:

1. Is demand growing?
2. Are customers staying?
3. Are they paying more over time?
4. Are we running out of cash before we figure it out?

Everything else is noise.

The best operators I’ve seen track 5–7 metrics max.
They review them weekly.
And they tie each metric to a clear action.

Everyone tracks KPIs.
Very few track the right ones.

If you want to find your biggest 1% opportunities,
check out scalingcfo.io.

Free assessment.

If this helped, save it.

Samsung wasn’t always a tech giant.

It was a tiny grocery store in 1938.

Lee Byung-Chull had $0. Just noodles, dried fish, and ambition.

Most people would stay small. He built a $720B empire.

Here’s how:

✅ Saw a need. Korea needed industry after the war.

✅ Took action. Trading → textiles → heavy industry.

✅ Bet on the future. Electronics in 1969. First black-and-white TV. Then semiconductors. Then global domination.

✅ Built a culture. Quality over quantity. Meritocracy. Vision.

✅ Played the long game. Critics doubted. Scandals happened. Growth didn’t stop.

From noodles → TVs → semiconductors → Galaxy phones → global tech leader.

Most people chase attention. Samsung chased leverage.

Legends aren’t born. They’re built.

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Cruz Gamboa

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The Battle

Lester Chng

Cruz Gamboa

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