Mark MacLeod

Limitless.ceo

Limitless is an exclusive community of VC and PE-backed CEOs who want
to scale themselves and their companies without limits.

Founder

I coach startup CEOs to grow themselves and their business all the way to a massive exit

SurePath Capital Partners

SurePath Capital Partners is the premier strategic financial advisor to the global SMB Software market. With offices in Toronto and San Francisco, we aim to be the #1 advisor in this space globally and the one call CEOs and board make when they need to make a deal happen.

FreshBooks

I led finance and corporate development at FreshBooks - the #1 cloud accounting specialist for small business owners. Since 2004, over 5 million people have used FreshBooks to track time, organize expenses and invoice clients online and in the cloud.

Accomplishments:
- Closed $30M institutional funding round + other unpublished transactions
- Led the process to find a partner to backstop a new product line
- Sourced and closed other key revenue-generating partnerships

CFO + Chief Corporate Development Officer

Real Ventures

Venture Partner

Parter at Real Ventures where I focus on SaaS, freemium, e-commerce and digital media seed investments

Director, Fabric Technologies
Director, Context.io (sold to Return Path)
Director, Frank and Oak
Observer, Rewardli Inc.
Investor, Thinknear.com (sold to Telenav)
Investor, Localmind.com (sold to Airbnb)
Investor, Massive Damage Inc.
Director, Sweet IQ (sold to Reachlocal)
Observer, Unbounce.com
Investor, Engagio (sold to Influitive)
Investor, Origin.al Internet Company

General Partner

Tungle Corporation

CFO for Tungle - a great solution for meeting coordination.

Raised a $5M "A" round. Served as CFO through the successful sale of the company to RIM.

SaaS, E-commerce, Marketplace companies

Interim CFO, Shopify
Advisor, Well.ca
Advisor, Cakemail 
Advisor, Dok Dok Inc 
Advisor, Raymark
Advisor, Sitezoogle 
Interim CFO, Status.net Inc.

Advisor & CFO

Mobivox

Led finance, operations, legal, HR, strategic planning functions for this mobile communications startup. Raised an $10M B round led by Flybridge. Raised an additional $1M in China. Made major improvements to execution, ops, key metrics, etc.

Terrascale Technologies Inc.

Led finance, operations, customer support, IT and manufacturing for this venture-backed networked storage vendor. Negotiated the sale of Terrascale to Rackable Systems (NASDAQ: RACK) in a deal returning 10x on invested capital.

VP, Finance

Hexago

Prepared this 15 person IP networking startup for commercialization & ‘B’ round funding. Responsibilities included financing, all back office operations, investor + board relations and negotiation of all  agreements. Towards the end of my term, I was given increasing responsibility for OEM sales and strategic relationships.

I help startup CEOs go from $5M in revenue to a massive exit

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. 

I was a General Partner in Real Ventures, one of Canada's largest and most active seed stage funds. My investments there include the fund's largest cash on cash and highest IRR returns to date. 

Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

The thing I loved most about these roles was the one on one coaching and advisory conversations I had with CEOs. 

Since 2020 I have been coaching, investing in and advising CEOs + helping them execute game-changing deals.

I am a semi-active angel investor with a portfolio of 22 investments, 2 highly positive exits and counting.

In my spare time, I am a passionate CrossFit athlete and electronic music producer/ DJ. I also run Deep Down Music, a record label.

I coach, advise and invest in the CEOs of high growth technology companies & help them execute game-changing deals.

The Tokyo Test.

Before I hire anyone or partner with a VC, I ask myself one question:

Would I be excited to sit beside this person on a 14-hour flight to Tokyo?

If the answer is no, I pass.

Life is too short to work with people you don't actually like.

Skills matter. Chemistry matters more.

Use the Tokyo Test.

Helping VC-backed CEOs scale themselves and their companies without limits. | Host of The Startup CEO Show podcast

The most senior person in the room uses the fewest words.

Junior: 10 slides to explain the problem
Mid-level: 5 slides with bullet points
Senior: "We have a cash flow issue. Here are three options."

Brevity isn't about being short. It's about being clear.

It means you've done the hard work of:
- Cutting through the noise
- Identifying what actually matters
- Removing your own confusion first

If you can't explain it simply, you don't understand it yet.

Watch how the best CEOs communicate:
- They get to the point
- They don't hedge with qualifiers
- They don't need jargon to sound smart

The CEO who says "Revenue is down, we need to cut 15% of headcount by Friday" is more senior than the one who sends a 2000-word memo about "organizational optimization initiatives."

You earn seniority when you stop needing extra words to feel credible.

Complexity is easy. Clarity is hard.

If you want to level up, start cutting.

Subscribe to my newsletter and get a 22 page presentation on the secrets of Limitless CEOs https://lnkd.in/gWqQBd-n

Bryn Jones grew PartnerStack for 4 straight years at 100% growth.

Most founders dream of that problem.

He told me it nearly broke him.

His insight: "Growth solves everything. Except it solves everything by letting you ignore problems.

You can only pave over so many cracks before the whole thing collapses.

The wildest part? Fixing those problems after Tech Winter hit was the most fulfilling work of his career. More than the hypergrowth years.

If you missed my podcast with Bryn, here is the interview. We cover:
Also in this conversation:
✅  How being on Canada's national swim team prepared him for 10 years as a CEO
✅  Why most partnerships fail despite their potential
✅  The one question that determines if a partnership will work
✅  Why he ignored his instinct and what happened next

Read it here:

Open article: PartnerStack's CEO Bryn Jones on 10 Years of Building B2B Partnership Networks and Why Growth Nearly Broke Him - Mark MacLeod by markmacleod.me

PartnerStack's CEO Bryn Jones on 10 Years of Building B2B Partnership Networks and Why Growth Nearly Broke Him - Mark MacLeod

Work hard. Play hard. Sleep hard.

This is my mantra.

Work hard: Anything worth doing is never easy. You need to push.

Play hard: Play makes life worth living. Most CEOs think this is a post-exit luxury. I disagree. For me, "play" is music and yoga. Non-negotiables.

Sleep hard: Another thing many CEOs skip. To show up as your best self and crush without burning out, you need to sleep like it's your job.

You are a mental athlete. Athletes sleep like it's their job.

Nobody is thinking about you.

Seriously.

Your competitor? Too busy with their own problems.

Your team? Thinking about their own issues.

Your board? Looking at the numbers, not judging you as a person.

The brutal truth: You're not the main character in anyone's story but your own.

So why are you making decisions based on what "they" might think?

❌ Holding back on that bold strategy
❌ Overthinking that honest conversation
❌  Not sharing your real challenges

Your anxiety about perception is burning energy that you need for  building.

The CEOs who scale fastest realize that only results matter. Not optics. Not opinions. 

Make the call. Say the thing. Take the risk.

They're all too busy worrying about what YOU think of them.

If your direct reports drain you, you have the wrong people.

Or you're doing their job for them.

I see this constantly with the CEOs.

❌  They finish a day of back-to-back 1-on-1s and they're exhausted.

❌  They spend more time fixing their team's work than doing their own.

❌  They dread certain meetings because they know it'll be them solving problems again. Or a certain team member just saps them of energy.

Here's what should happen instead:

✅  Your direct reports should energize you.

✅  You should leave your 1-on-1s thinking "damn, I'm glad they're on this team."

✅  You should feel excited about what they're building, not anxious about cleaning up their mess.

✅ You should get ideas from them, not just give them.

If that's not happening, there are only two reasons:

1. You hired wrong
2. You're not letting go

Hiring wrong is fixable. Make the change.

Not letting go is also fixable, but it requires you to change.

Stop jumping in to save the day. Stop being the one with all the answers.

Build systems. Train properly. Then trust.

Sometimes you need to watch things break to learn where the system needs fixing.

You can't scale a company where everything runs through you.

And you definitely can't sustain it.

Your team should multiply your energy, not divide it.

If they're not doing that, something needs to change. 

P.S.
This was my all star team at SurePath Capital. Each and every team member gave me enery and leverage.

This is the story of how a tax law professor built a $30M ARR company while still teaching classes.
 
Benjamin Alarie is the CEO of Blue J Legal AND a professor at U of Toronto law school.
 
He saw AI coming for the legal profession in 2011. Had a choice: watch it happen or build the future himself.
 
The kicker? He's not a software engineer. His co-founder moved from Australia because of a childhood friendship.
 
They started in 2015. Spent 7 years building with supervised machine learning. Then LLMs hit. They pivoted hard in 2023.
 
Now: 300%+ YoY growth. 10 new logos daily. Approaching $30M ARR.
 
The lesson isn't about AI or tax law.
 
It's about recognizing when your deep domain expertise intersects with massive technological shifts.
 
Ben knew tax research was painful because he'd lived it for thousands of hours. He could see exactly what needed to exist.
 
Most professors would write another paper. He built a company.
 
We talked about:
✅ Managing investors while maintaining an academic career
✅ Enterprise sales when your TAM is basically the Big 4
✅ Why LLMs changed everything
✅ The $500B tax compliance market nobody thinks about
 
Link in comments.

The new CEO flex: Your sleep score.

Remember when pulling all-nighters was a badge of honour?

That doesn't scale. It just makes it harder for you to build your company.

Elite performers know: sleep is performance.

8 hours. 90% sleep score. REM cycles optimized.

That's the real flex.

You're a mental athlete running a company worth millions.

Sleep like your business depends on it.

Because it does.

No small plans.

It takes the same effort to hit "achievable" targets as it does for "crazy" targets.

Same meetings. Same strategic planning. Same team-building.

The only difference? Your ambition.

Most CEOs set targets they know they can hit. Safe. Predictable. Boring. They do this so they can tell their investors they are "on plan".

As you get ready for 2026, consider setting seemingly impossible targets.

Google was famous for this with it's moonshot thinking.

Hitting 60% of a moonshot target may be much better than hitting 100% of an achievable target.

Early stage VC: "We make 30 bets a year. Let's take a shot."

Growth stage VC: "We make 3 bets a year. Prove everything."

This is the shift founders don't see coming.

Seed investors are building a portfolio. If 1 in 10 works, they win. They can afford leaps of faith.

Growth investors are making concentrated bets. If 1 in 3 fails, their fund is cooked. They can't afford to be wrong.

So they need:
✅  Three years of consistent revenue growth
✅  Proof of unit economics
✅  Evidence of repeatability
✅  Clear path to exit

They're not being difficult. They're being rational.

Your Series A took 20 conversations.
Your Series C will take 200.

The math is simple:
- Early stage: high volume, high failure tolerance
- Late stage: low volume, low failure tolerance

Build your pipeline accordingly.

If you're raising growth stage capital with a seed stage pipeline strategy, you're going to run out of runway before you find your lead. Growth investors want to track you for a long time before they invest. No FOMO decisions.

Don't get bitter. Get realistic. 

Subscribe to my newsletter and get a 22 page presentation on the secrets of Limitless CEOs https://lnkd.in/gWqQBd-n

P.S.
here's a random photo of me at the Calgary Stampede back when I was a VC. Cowboy hats are underrated

You can't see the system when you're inside it.

Your best thinking happens when you step out of the environment that created your current thinking.

Today I am joining Adrian Salamunovic to kick off the first Limitless Unconference in Tulum.

A group of ambitious humans are arriving. All builders. All on the go.

The goal is to reset. Take a breath. Take stock of what’s working and not. In our companies and our lives.

To engage in healing breath work and movement. To gain clarity and set our commitments and dreams for 2026.

I use retreats as a way to recharge, reset and recommit every year. My goal is to have one big retreat per year and 3 small ones.

This gives me perspective and direction. I slow down to speed up.

CEOs who build for the long term don't just work hard. They build in time to step back. Quarterly. Monthly. However often you need it.

Because perspective isn't found in the grind.

It's found when you finally stop grinding.

When you lose your health, you realize nothing else matters.

So many CEOs that come to me for coaching are killing themselves and can't keep up.

In this video Robbie Bent co-founder and CEO of Othership gets real about his journey. See comments for the full conversation.

P.S.
If you want to build a market-leading company without sacrificing your health, come join us at Limitless (see my featured post for the link)

Open video: ✂️ The CEO role will kill you on youtube.com

Want to 10x your company? Start by 10x'ing your capacity.

You can't scale what you haven't built in yourself first.

I see CEOs obsessing over growth hacks, fundraising strategies, and hiring plans.

But they ignore the most important variable: themselves.

Your energy. Your focus. Your ability to handle stress. Your decision-making under pressure.

Most founders hit a ceiling not because their market is too small or their product is wrong.

They hit a ceiling because they've maxed out their personal operating system.

The tree grows tall because its roots go deep.

Your company will only rise as high as your foundation is solid.

This means: sleep, exercise, mental health, relationships, nervous system regulation.

The boring stuff that everyone skips.

The biggest outcomes are founder-led. Always have been.

Zuck. Bezos. Jobs. Musk.

They didn't just build companies. They built themselves into people capable of leading those companies.

Stay grounded while you build.

Invest in your foundation as aggressively as you invest in your business.

That's how you become limitless.

Here's why meditation feels scary (at first)

The moment you sit down, the noise starts. Not around you—inside you.

You suddenly notice how busy your mind is. Thoughts. Loops. Worries. Stories.
It’s a lot.

But here’s the truth: that chaos was already there. You’ve just been working so hard to think clearly through it. This is why you're so exhausted. Why you can't think clearly.

Imagine how much energy you’d reclaim if your mind was actually clear.

Meditation shows you the mess then helps you clean it up.

Yes, it’s uncomfortable at first.

But on the other side? Clarity. Presence. Power.

Sit anyway.

The peace you’re seeking is already within you.
✨

Evan Nierman

Red Banyan

Red Banyan is a strategic communications firm specializing in public relations, crisis management and marketing.  Red Banyan Group combines creative thinking, steady judgment shaped by experience and a relentless commitment to achieving results for its clients.  Red Banyan offers a wide array of services, including: media relations, crisis management, marketing, corporate communications, litigation support, social and digital media, copywriting and editing and media training.

Founder and CEO

Entrepreneurs'​ Organization

Entrepreneurs Organization (EO) Member 

Green Bullion Financial Services

Director of Public Relations

Saylor Company

Principal

AIPAC

Editorial Director and Executive Editor of Near East Report

Communications Associate and Managing Editor of Near East Report

Communications Assistant

Founder & CEO, Red Banyan PR | Author of Top-Rated Newsletter on Communications Best Practices

My team and I are focusing on STRATEGY and RESULTS. I lead an international PR and crisis management firm that exists to press the truth.  We empower clients to achieve business goals using strategic communications. We specialize in crisis management, high-stakes PR, and complex assignments requiring creative thinking, steady judgment shaped by experience and a relentless commitment to exceeding expectations.

Red Banyan Group is a strategic communications firm specializing in public relations, crisis management and marketing.  Red Banyan Group combines creative thinking, steady judgment shaped by experience and a relentless commitment to achieving results for its clients.  Red Banyan offers a wide array of services, including: media relations, crisis management, marketing, corporate communications, litigation support, social and digital media, copywriting and editing and media training.

Titles change. Companies reorganize. Projects end.
But your mission is what stays.

I see this every day in crisis PR.

People who attach themselves to roles, personalities, or status lose direction the moment pressure rises.

People who attach themselves to a mission stay steady even when the narrative falls apart.

In high-pressure situations the difference is striking:

a.) Leaders who cling to titles look for protection.
b.) Leaders who cling to purpose create solutions.

When a leader centers their compass on a goal instead of ego, the team immediately knows how to respond under pressure.

This shapes reputation from the inside long before the outside world sees it.

If you want stability in difficult moments, start here:

Anchor yourself to values, not positions.

Positions shift. Integrity remains.

Focus on mission, not personalities.

Preferences crack under pressure. 

Mission keeps direction.

Build a culture where purpose leads and titles follow.

This creates a team that holds together even when the silence gets uncomfortable.

In crisis PR, purpose is the most reliable navigation tool.

Reputation begins at the point where you choose to attach yourself.

Follow Evan Nierman for insights on crisis PR, leadership under pressure, and reputation management.

A reality check for any leader: 
Your crisis plan is only as strong as the person who goes first.

Most teams assume a crisis will activate responsibility automatically.

They think the plan will guide everyone.

They expect people to step in at the right moment.

But crises do not work that way.

The real breakdown happens when every person waits for a signal that never comes.

Hesitation does more damage than the crisis itself.

A crisis-ready team runs on four behaviors:

1. Awareness → People notice early signs instead of assuming “it will pass.”
Awareness stops problems before they spread.

2. Initiative → Someone steps forward even if it is not part of their role.
Initiative prevents escalation.

3. Communication → Information moves quickly and clearly.
No gaps, no guessing, no confusion.

4. Follow-through → What starts gets finished.
No loose ends for the public to fill with their own narrative.

Without these behaviors, plans stay on paper and the crisis gains control.

With them, the team acts with clarity and the situation stabilizes before it spirals.

Follow for weekly insights on crisis leadership and responsible communication.

In every crisis, the same problem appears:
everyone waits for someone else.

Most crises don’t escalate because of external pressure.

They escalate because of internal silence.

In organizations without a clear chain of responsibility, the same pattern emerges: everyone assumes it’s “someone else’s job.”

And while that pause drags on, the internet becomes the spokesperson.

A vacuum in a crisis never stays empty.

If you don’t fill it, the narrative will.

Leadership in a crisis isn’t delegation.

Leadership means the first sentence, the first move, and the first signal come from you not from the chaos around you.

The most dangerous phrase in crisis PR is: “I assumed.”

When a crisis hits, it must be unmistakably clear who speaks, who leads, and who owns the response because while the team hesitates, the reputation burns.

Follow for weekly insights on crisis PR and reputation management.

Reputation is what people believe about you. 
Character is who you are when no one is watching.

You can shape reputation.

You choose your message, control the narrative, and manage how you appear in public.

Character is different.

It is built in the unseen moments.

In choices that cost you something.

In how you treat people who cannot offer you anything in return.

Here is the truth many leaders learn late:

Reputation without character looks strong until pressure hits. 

Then it collapses.

Reputation is external. 

Character is internal.

When they do not align, that gap becomes the crisis.

You can polish reputation.

You cannot fake character.

People may believe the image for a while.

But character shows itself over time in patterns and consistency.

Character is what survives the crisis.

If it is real, you rebuild.

If it is not, everything falls apart.

Leaders who last are not the ones with the best PR.

They are the ones whose private behavior matches their public words.

Reputation may open the door.

Character is what keeps you in the room.

Follow Evan Nierman for weekly insights on leadership, integrity and what endures.

The way you treat people when no one’s watching
says more about your leadership than any title ever could.

I’ve seen this in boardrooms, startups, and crisis situations.

The leaders who earn trust under pressure are the ones who lead with respect, not authority.

Reputation doesn’t begin with public perception.

It begins in private moments how you speak to assistants, interns, or colleagues when stress peaks.

Those quiet interactions shape culture. 

And culture shapes how your organization responds when challenges appear.

If you want lasting trust, start here:

1.) Respect without hierarchy.
People notice how you treat those who can’t advance your career. Respect creates loyalty that outlasts titles.

2.) Listen before reacting.
When pressure rises, the instinct is to speak first. Listening shows discipline — and builds confidence in your judgment.

3.)Treat every role as essential.
No crisis is solved alone. When people feel valued, they take ownership — and that’s where real resilience begins.

Leading with title earns compliance.

Leading with respect earns commitment.

Reputation is built on how people feel in your presence, not on your résumé.

Follow for weekly insights on leadership, crisis PR, and reputation management.

A client once told me: "I don't want to apologize. I want to win."
That's when I knew we had a problem.

He was furious.

The media was running a story he believed was unfair.

The facts, in his view, were being twisted.

And his instinct was to fight back. Publicly. Loudly.

To "set the record straight."

To win.

I understood the impulse.

When you're being criticized—fairly or not—the natural reaction is to defend yourself.

To prove you're right.

To make everyone see your side.

But here's what I told him:
"You can win the argument and lose everything else."

Because in a crisis, winning isn't about being right.

It's about being trusted.

And trust doesn't come from fighting.

It comes from how you show up when things go wrong.

Here's what happens when ego drives crisis response:

You focus on being right instead of being heard. 

People don't care about your ten-point rebuttal. 

They care whether you understand their concern.

You turn critics into enemies. 

When you fight back, you escalate. 

And escalation rarely ends in your favor.

You lose the people in the middle. 

The ones who were willing to listen? 

They stop listening when you start swinging.

The conversation I had with that client wasn't easy.

But eventually, he understood:

The goal isn't to win.
It's to resolve.

To move through the crisis with your reputation intact.

To show humility when humility is called for—and strength when strength is needed.

We didn't issue a combative statement.

We acknowledged the concern. 

Clarified the facts calmly. 

Focused on what we were doing moving forward.

No victory lap. No "gotcha" moment.

Just accountability and action.

The story faded.

The relationship with his stakeholders held.

And he learned something more valuable than winning an argument:
In crisis, ego is a liability.

Strategy is what saves you.

Follow for weekly insights on strategy and leadership under pressure.

The verdict doesn't matter if you've already lost in the court of public opinion. Litigation PR has changed.

It used to be simple: Don't comment on pending litigation. 

Let the lawyers handle it. 

Stay quiet until the judge rules.

That strategy doesn't work anymore.

Because while your legal team is preparing motions, the other side is shaping the narrative on social media, cable news, and in the press.

And by the time the case settles or goes to trial, public perception is already locked in.

Here's what's different now:

The court of public opinion moves faster than the courtroom.

A lawsuit gets filed. 

Within hours, it's trending.

You can't wait 18 months for discovery to tell your side of the story.

The damage is happening now.

Silence reads as guilt.

"No comment" used to be safe.

Now it looks like evasion.

If you're not telling your story, someone else will and their version will stick.

Juries Google.

Even when judges instruct them not to, jurors search for information.

What they find online influences how they interpret the evidence in court.
Settlements don't erase headlines.

You can settle the case. 

You can't settle the reputation damage.

If the narrative is "they did something wrong and paid to make it go away," that story lives forever.

What effective litigation PR looks like today:

1. Legal and PR working together from day one. Not as adversaries. As partners with a shared goal: protect the client.

2. Proactive messaging that tells your side without compromising the case. You can communicate strategically while respecting legal boundaries.

3. Stakeholder management beyond the courtroom. Employees. Investors. Customers. They're making decisions now based on what they see—not waiting for a verdict.

4. Digital reputation management. Ensuring your narrative isn't buried by the opposition's spin.

The goal isn't to win the PR battle and lose the legal one.

It's to protect your reputation while you fight the case—so when it's over, you still have a business to run.

Litigation PR isn't optional anymore.

It's essential.

Because even if you win in court, losing in public can cost you everything.

Follow for weekly insights on litigation communications and reputation protection.

If you're delivering bad news over email, you've already lost the relationship.
I see it all the time.

The termination notice sent at 5 PM on a Friday.

The policy change buried in a mass email.

The apology that reads like it was drafted by legal and approved by no one with a pulse.

Leaders hide behind screens when things get hard.

And it always backfires.

Because bad news delivered without presence feels like cowardice.

And cowardice destroys trust faster than the bad news itself.

Here's why email fails in crisis:

1.) It removes accountability. You can't see the person's reaction. 

You can't answer their questions. 

You can't adjust based on how they're receiving it.

You just send it—and hope it lands okay.

2.) It feels transactional. Email says: "This is a task I needed to complete."

A conversation says: "This matters enough for me to show up."

3.) Tone gets lost. What you meant as direct reads as cold. 

What you meant as professional reads as detached.

And in a crisis, tone is everything.

4.) It invites misinterpretation. People fill in the gaps. 

They read between the lines. They assume the worst.

Because when you're not there to clarify, they're left to imagine your intent.

The hard conversations—the ones that matter most—deserve your presence.

Not your inbox.

That means:

→ A phone call when you can't be there in person.
→ A video meeting when you need to see their face.
→ A real conversation—not a one-way broadcast.

Yes, it's uncomfortable.

Yes, it takes more time.

Yes, it's harder than hitting "send."

But leadership isn't about efficiency.

It's about integrity.

And integrity shows up.

Even when—especially when—the news is bad.

Follow for weekly insights on communication, presence, and leadership.

Five words that never work in a crisis:
"It was just a joke."

I’ve heard this defense after an offensive tweet, a tone-deaf comment, or a video that “wasn’t meant seriously.”

Every time, it makes things worse.

Intent doesn't matter. Impact does.

You may have meant it as humor, but if it landed as hurtful or dismissive, that is what counts.

Explaining your intent doesn't erase the impact. 

It only sounds like avoiding accountability.

Humor doesn't land the same for everyone.

What is funny to you may be insulting to someone else.

Sarcasm gets lost. Tone gets misread.

And you do not get to control how people receive it.

"Just joking" sounds like minimizing.

People hear:

"You're overreacting."
"You're too sensitive."
"I'm not responsible."

That never ends well.

The internet doesn't care about your intentions.

A joke that fails in a room is awkward.

A joke that fails online is permanent.

Screenshots keep the words, not the tone.

What to do instead:

Own the impact.

"I meant it as humor, but I see how it landed, and I'm sorry."

Skip the justification.

Don't explain why they shouldn't be offended. 

Acknowledge that they are.

Know your audience.

Not every joke fits every context.

The best communicators understand this:

You don’t decide how your words are received.

You only decide whether you'll stand by them or own the mistake.

Follow for weekly insights on communication, accountability, and reputation.

Microsoft just bought a 27% stake in OpenAI.
On paper, it's a business deal. In reality,

it's a power shift that changes everything about who controls the future of AI.

And most people aren't paying attention.

Here's what just happened:

OpenAI—the company that gave us ChatGPT—was structured as a nonprofit with a mission: develop AI that benefits humanity, not shareholders.

Now it's becoming a public benefit corporation.

With Microsoft holding significant equity.

Translation: the guardrails just got weaker.

And the profit motive just got stronger.

This isn't just a tech story.

It's a reputation and accountability story.

Because when innovation moves faster than regulation, trust becomes the only thing holding the system together.

And trust is fragile.

Here's what this deal reveals:

Power and accountability are diverging.

Microsoft gains influence. OpenAI gains capital.

But who's accountable when something goes wrong?

When AI makes a harmful decision, who answers for it—the nonprofit mission or the corporate investor?

The structure just got more complicated. And complexity is where accountability dies.

The narrative is shifting before the public realizes it.

Most people still think of OpenAI as the "good guys" in AI development.

Independent. Mission-driven. Different from Big Tech.

But this deal quietly erodes that distinction.

And once the public catches on, the backlash will be swift.

Innovation is outpacing oversight.

AI development is moving at a pace regulators can't match.

New models. New capabilities. New risks.

And the companies building it are writing their own rules—because no one else can keep up.

That's a reputation time bomb.

Three lessons for communicators navigating the AI era:

1.) Transparency isn't optional anymore.
The days of "move fast and explain later" are over.

If your company is pushing boundaries in AI, you need to communicate what you're doing, why, and who's accountable—before someone else defines it for you.

2.) Mission statements won't protect you.

Saying you're committed to safety and ethics doesn't mean anything if your structure prioritizes profit.

The public is learning to look past the messaging and examine the incentives.

3.) One misstep reshapes trust overnight.

AI mistakes don't just hurt your brand. They reshape public perception of the entire industry.

When trust is the only thing preventing regulation or backlash, you can't afford to get it wrong.

This deal is a signal.

The AI race is accelerating.

And the companies that win won't just be the most innovative.

They'll be the ones who figured out how to build trust while everyone else was just building technology.

Follow for weekly insights on crisis management in the age of rapid innovation.

The video went viral within hours.



Erratic driving. Swerving across lanes. 

Tailgating. Confused explanations.

Britney Spears is struggling and the people who should be protecting her brand either can't reach her, or aren't there.

This is what happens when crisis management fails before the cameras start rolling.

Her family, once accused of micromanaging under conservatorship, is now reportedly uninvolved. She's entirely on her own.

That absence is a brand liability playing out in real time.

For public figures, a functioning support system is essential reputation management. Without close advisors and a competent crisis team, minor incidents escalate into viral PR disasters.

What every crisis team should learn:

1. Act before the cameras roll.

Warning signs were there—erratic posts, fractured relationships, behavioral shifts insiders likely noticed months ago.

Waiting until damage goes viral is a fatal mistake.

2. Build a network, not an audience.

Fans aren't advisors. Real stability comes from legal, emotional, and strategic professionals who can say "no."

If no one in the inner circle has that role, the inner circle is the problem.

3. Control the narrative—or be controlled by it.

Her Instagram follow-up was confusing, rambling, unsupervised. It made things worse.

Messaging needs to be intentional. Not every thought belongs online.

4. Understand the cost of visibility.

Britney Spears is a brand with cultural equity, legacy value, and commercial interest.

When celebrities become unstable in public, they jeopardize the long-term viability of their brand.

5. Have a comeback plan before the crisis hits.

Image rehabilitation must begin in calm moments, not after public collapse.

The Reality:

Once the video goes viral, you're not managing a crisis.

You're managing the aftermath of one that's been building for months.

When public figures lack a clear PR strategy, one misstep becomes an irreversible spiral.

Public life offers rewards, but also risk.

When the spotlight turns toxic, survival depends on having the right people, the right plan, and the ability to act fast.

Because if you don't manage your reputation, someone else will.

Follow for weekly insights on crisis intervention and reputation protection.

The House passing the Epstein files bill 427 to 1 is not the headline.
The real headline is what happens next.

Many people assume the release will simply reveal names and fuel public outrage.

They think the narrative will unfold on its own, driven by the documents alone.

It won’t.

The truth is that the decisive moments will unfold in the first 24 to 48 hours.
 
That is when teams move, stories shift and reputations are either protected or permanently damaged.

Here is the pattern that crisis professionals recognize immediately:

• rapid distancing from implicated networks
• controlled statements designed to anchor early perception
• coordinated messaging to shape how the public interprets new information
• quiet legal positioning before narratives harden

With preparation, reputations can be stabilized.
 
Without it, the public forms conclusions that become nearly impossible to reverse.

For a fuller breakdown of what the next phase will look like, see my crisis communications analysis on CBS LA:

https://lnkd.in/eNcjD88i

Excited to be a guest speaker at Broward College today. Sponsored by Kappa Delta Pi, the international honor society in education, this event highlights the importance of kindness in our lives and the impact each of us can make. #guestspeaker #browardcollege #education #kindnessmatters #leadership

Red Banyan has once again been named an Inc. Magazine Power Partner—recognized back-to-back as one of the top B2B firms in public relations. PROUD of the work we do, the IMPACT we create, and the TEAM that makes it happen. Grateful to the leaders who count on us when the stakes are highest. Recognition like this is earned by showing up, staying sharp, and delivering when it matters most.
#IncPowerPartners #RedBanyan #Leadership #CrisisPR #ReputationMatters

Open article: Red Banyan Named 2025 Inc. Power Partner | Red Banyan by redbanyan.com

Red Banyan Named 2025 Inc. Power Partner | Red Banyan

Even the most successful entrepreneurs have blind spots. 
I wrote this piece for Entrepreneurs'​ Organization's Inc. Magazine channel after seeing how often leaders overlook issues that quietly grow beneath the surface—especially when things are going well. Big takeaway? Success doesn’t erase your weaknesses. It often hides them. Staying aware is what separates leaders who grow from leaders who stall. 
Read the full article here:
https://lnkd.in/ei3ysW-x
#Leadership #Entrepreneurship #Growth #ReputationMatters

Open article: 5 Blind Spots That Sneak Up on Successful Entrepreneurs by inc.com

5 Blind Spots That Sneak Up on Successful Entrepreneurs

It’s not every day your work helps put a client in the dictionary. 
But that’s exactly what Red Banyan did.

Through focused media relations and strategic advocacy, our client’s insights were quoted by Merriam-Webster and cemented into the official definition of “radicalism.” A defining voice on a defining issue—with national impact.
This kind of influence doesn’t happen by chance. It’s the result of precision, consistency, and the right message delivered at the right time.

This is the power of strategic communications.
This is the power of Red Banyan.

See the dictionary citation: https://lnkd.in/eFzcmDE7
#StrategicComms #MediaRelations #ThoughtLeadership #CrisisPR #ReputationMatters #Authority

Glen Powell understands that reputation is the most valuable asset. He is smart and strategic about his every move, and it's paving the way to new levels of superstardom. My take in the Us Weekly cover story.#celebrity #publicrelatons #strategy

Open article: How Glen Powell Balances His Career, Dating and Life in Texas (Excl) by usmagazine.com

How Glen Powell Balances His Career, Dating and Life in Texas (Excl)

When a crisis occurs, customers shouldn’t be left to solve it themselves. 
As I shared with Business Insider, hospitality companies earn goodwill by removing the burden, not adding to it. Relocation, refunds, and clear guidance aren’t perks. They’re the basics. Read the full story:

Open article: Hilton's CEO says problem-solving keeps guests coming back by businessinsider.com

Hilton's CEO says problem-solving keeps guests coming back

Leadership means staying grounded when everything around you is uncertain.

I recently contributed this piece to EO on how today’s leaders can build resilience that actually lasts. Especially when times are turbulent, the habits you form before the crisis often define how you lead through it.
Grateful for the chance to share these ideas with the EO community—and would love to hear what’s worked for you. Read the full article here:
https://lnkd.in/eU_n8UCG
#Leadership #Resilience #Entrepreneurs #CrisisPR #StrategicComms

Open article: Developing Resilient Leadership Habits for Uncertain Times by eonetwork.org

Developing Resilient Leadership Habits for Uncertain Times

Learning about diplomacy, debate and ideally compromise, collaboration and problem-solving. Critically important business and life skills. Proud of my daughter Noa Nierman for participating in Model U.N. as a diplomat from Jordan!

Student at Marjory Stoneman Douglas | Teen Leader |

The past two days, I’ve been honored to participate in BULLSMUN 2025 as a delegate for the Hashemite Kingdom of Jordan. This is a Model UN conference for high school students where we use parliamentary procedure, give speeches, and collaborate to solve current global diplomatic issues. I participated in the FAO (Food and Agriculture Organization) committee, where the bloc I led developed a logistical and fair economic and legal framework addressing climate change and managing the effects of global hunger. I was honored to be named Outstanding Delegate by the committee chair, as well as my school being named best large delegate with the most amount of wins! Grateful for this opportunity to collaborate with other students, practice my public speaking, and craft detailed resolutions to real life issues. I am also excited to announce that I have officially joined the MSD Model Un club officer team as the social media manager. Looking forward to the next conference already!

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The Battle

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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);}Mark MacLeod's LinkedIn Performance

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