Mark MacLeod

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.

Founder

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

The best CEOs I've worked with all have one thing in common: They're blunt.

Not rude. Not cruel. Not careless with their words.

Blunt.

They say what needs to be said in the room where it needs to be said.

They don't soften feedback until it loses its meaning.

They don't wait three months to have the conversation everyone knows is overdue.

They don't hide behind politeness when clarity is what the team actually needs.

Most founders confuse being nice with being kind.

Nice avoids the truth to protect feelings.

Kind delivers the truth because the stakes are too high not to.

Your team doesn't need you to be comfortable.

They need you to be clear.

Bluntness with respect is one of the highest-leverage leadership skills you can develop.

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

Helping ambitious CEOs & founders scale world-changing companies without sacrificing their health, happiness, purpose, or humanity

No alternative text description for this image

I don't think I will ever fully retire.

Retirement is a concept built for a world that no longer exists.

It assumed you'd grind for 40 years, then stop.

Trade your health for money, then try to buy it back.

But what if you could work forever?

Not because you have to. Because you want to.

Because building still lights you up at 60, 70, 80.

That changes the entire equation.

You can't run this game like a sprint.

The founders who burned out at 45 didn't fail because they lacked talent. They failed because they built a pace they couldn't sustain.

We're going to live longer than any generation before us. The question isn't when you stop.

It's how you build a life and a body and a mind that lets you keep going as long as you choose.

That means sleep isn't optional. Recovery isn't weakness. Energy isn't something you sacrifice for the next milestone.

It's the asset that makes every future milestone possible.

Retirement is what happens when you run out of energy.

Sustainability is what happens when you never do.

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

I am leaning into my weirdness, and it feels good.

I have never been a stereotypical CPA. When I was in undergrad, I designed my life around raves. Classes were Tuesday - Thursday. This enabled me to go dancing all night Saturday and recover. 

While I love to serve, I hate having a boss. So, while my peers went the “Big 4” route, I joined a small firm serving founders. I have only ever been or worked with founders. 

I have always leaned into what I love. I love to write. When I look back, all of my most important relationships came from my writing. Tobi from Shopify. Mike from FreshBooks. The guys starting Real Ventures. All came in part because they read my thoughts.

Then there’s yoga. Starting casually in my late 20s, yoga has evolved to become the foundation of my life.

The stretches offered in most North American yoga studios are a tiny fraction of what yoga is. In fact, the word “asana” (that’s what these postures are called) is barely mentioned in the Yoga Sutras.

Yoga is a complete system for living your life. My goal is to live every minute in accordance with yogic practices and values.

I discovered kundalini yoga in 2012. I got serious about it in 2019. And I teach it now.

Kundalini focuses on building and directing energy. We all have dormant energy at the base of our spine. Through these practices (called “kriyas”), we activate and direct that energy. 

Studies have shown that this practice turns on dormant parts of your brain. It unlocks our potential.

All of this mix of yoga, breathwork, meditation, and human optimization has co-mingled with my startup experience to create Limitless. 

My mission is simple: to redefine how founders build companies by putting their energy, health, and inner alignment first. So they can scale without limits and lead from a higher state.

Change your life so you can change the world!

Hard to think of something more motivating to work on!

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

undefined undefined

Certified Personal & Business Performance Coach

Chartered Professional Accountant (CPA)

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

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

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

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.

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

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

General Partner

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.

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

Advisor & CFO

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.

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

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.

Strategic consulting assignments: 
•	Advised on the sale of two software companies and the purchase of an education services company
•	Led the successful restructuring of an insolvent retailer. The company is now thriving and expanding
•	Enabled the restructuring & strategic refocus of a new media company that resulted in a 3x growth in revenues and 5x growth in profit & cash flow

President

Was responsible for Finance, Alliances and Corporate Development functions. Raised $19M in equity over 2 rounds + oversaw growth to over 100 people. Established many key partner relationships

Director, Finance + Corporate Development

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

Marie Chevrier Schwartz spent 10 years building Sampler. Raised venture capital. Grew it to real scale. Then the business went bankrupt.

Most founders go dark when that happens. Marie did the opposite. She went on social media and told everyone.

The thing she said that stuck with me most: The day she accepted it was over, she felt relief. Not defeat. Relief.

Because she finally separated who she was from what she built.

That's the hardest thing in entrepreneurship. Not the fundraising. Not the product. Not the market timing.

It's realizing you are not your company.

Marie was late in her pregnancy when she learned the business wouldn't survive. She had a newborn when it officially ended. And instead of shutting down, she used that moment to rebuild her identity entirely.

She's went on to runTechTO, Canada's largest tech community, serving 60,000 founders. Different chapter. Same energy. More clarity.

If you missed the podcast, the full conversation is on my blog → link in the comments.

Most founder interviews are about fundraising, growth hacks, and exits.
This one was different.

I sat down with Tonya Papanikolov, founder of Rainbo, one of the leading functional mushroom brands. She's a holistic nutritionist, a Kundalini yoga teacher, and someone who built her company from a meditation download, not a pitch deck.

What struck me most was how she thinks about success.

Not revenue targets. Not market share.
Alignment. 

Is what she's building aligned with her deeper purpose? And when the answer is yes, everything else follows.

She also said something that stopped me: when she feels the urge to escape and retreat from the work, that's usually a sign she's avoiding the next level of growth, not that she needs rest.

That's a distinction most founders never make.

We talked about building a CPG brand from scratch, getting into Whole Foods, running a company with her husband, and why her morning practice is the most important thing she does for the business.

If you missed the podcast, the full conversation is on my blog

Botkeeper raised $90M+ and just shut down after 11 years. It's a cautionary tale we all can learn from.

Raising capital is not a sign of success. It just means someone gave you a shot.

We celebrate fundraising like it's the finish line. It's not. It's the starting gun.

And sometimes it's the thing that kills you.

More capital means more pressure, higher burn, bigger expectations, and less room to figure things out.

Botkeeper never nailed product-market fit with accountants. But they kept raising anyway. I don't blame them. But this happens a lot with VCs overfunding.

$90M later, the outcome was the same as if they'd run out of money at $5M.
Except that more people got hurt.

The founders I work with who build lasting companies treat capital as fuel for what's already working. Not a substitute for what isn't working.

The true test of your values isn't when you fire a low performer.
Everyone can do that.

It's when you exit a high performer who violates them.

The person who is hitting their numbers. The one the board loves. The one your team depends on.

But they're toxic. They undermine trust. They treat people like collateral damage.

And you know it.

Most CEOs tolerate it because the results are too good to lose.

That's not pragmatism. That's a signal to your entire company that values are negotiable when the numbers are right.

The moment you exit that person, two things happen.

First, it hurts. Revenue might dip. There's a gap.

Second, your culture becomes real. Every person on your team now knows the values aren't a poster on the wall. They're the operating system.

And that's worth more than any one performer.

Harry Stebbings says fundraising has changed.

According to Harry, SaaS founders growing 2-3x have two choices:

Use AI to accelerate to 8-10x growth. Or cut burn and never raise again.

The reality is more nuanced.

The real question isn't "which path." It's "how do I build OPTIONALITY so I can choose either, on my terms?"

Optionality has never been more important than it is now.

Optionality means:

✅ Your can get to cashflow break-even in runway if you are not there already.

✅ Your growth rate & unit economics let you raise if and when you want to.

✅You are known to your most natural buyers and can enter into a warm, qualified exit process at any time.

And a personal consideration here: 

✅ As founder, your energy and clarity let you make that strategic call from strength, not panic.

The founders who win in this market aren't picking door 1 or door 2.

They're building a company, and a version of themselves, that can walk through whichever door makes sense, whenever it makes sense.

That's not simple. But it's the real game.

Founder @ 20VC

The biggest risk of AI isn't losing your job. It's never being able to stop working.

The people burning out fastest right now aren't the ones resisting AI.
They're the ones who embrace it most.

A new Harvard Business Review study followed a tech company for eight months and found that when people genuinely adopted AI, they didn't work less. They just did more. 

To-do lists expanded to fill every hour that AI freed up, then kept going. 

Work bled into lunches and late evenings. Not because anyone was pressured. Because the tools made it more doable.

This is the trap nobody's talking about.

AI doesn't create boundaries. It removes them.

And without boundaries, more capacity just becomes more work.

This is why health, energy, and inner clarity aren't nice-to-haves in the AI era.
They're survival tools.

The founders who thrive through this won't be the ones who squeezed the most out of every AI tool.

They'll be the ones who knew when to stop. Who protected their sleep. Who built recovery into their operating system. Who had the self-awareness to say 
"I can do more," and the discipline to say "but I won't."

Being able to call it a day and feel good about what you accomplished will become a superpower (it always was..).

AI is the most powerful accelerant founders have ever had.

Without boundaries, it accelerates burnout just as fast as growth.

Your job as CEO isn't to do more. It's to remove friction.

Friction is everywhere. It's the slow approval process. The unclear ownership. The meeting that should be an email. The hire you haven't made. The conversation you've been avoiding.

It's not one big thing. It's a hundred small things quietly dragging your company down.

Most founders tolerate them. They work around them. They get used to the drag.

Limitless CEOs have a different habit.

They remove one piece of friction every single day.

It sounds small. But compounded over a quarter, that's 90 obstacles gone.
Over a year, you've fundamentally changed how your company operates.

Not through a big reorg. Not through a new strategy deck.

Through the daily discipline of making things a little easier for your team to win.

That's the real job.

Find and remove one piece of friction every day.

AI made you faster. It didn't make you better at stopping.

Every CEO I speak with has the same problem right now: the tools keep getting better, but the days keep getting fuller.

So I teach them a simple boundary protocol: Block one hour a day that is completely analog.

No screens. No Slack. No AI. No input at all.

Walk. Breathe. Sit. Think. Or do nothing.

This isn't a wellness hack. It's an operating decision.

Because the quality of your leadership is determined in the space between inputs. Not during them.

The founders who protect that space make sharper calls, see further ahead, and last longer than the ones running at full capacity every waking hour.

Your brain needs time offline to process what it's taken in. Without that, you're not thinking. You're just reacting faster.

AI gives you speed. Analog time gives you clarity.

You need both. Most founders only have one.

I asked a CEO client to rate his happiness. He said 6 out of 10.
I asked what would make it a 10.

His answer wasn't more revenue. Wasn't a bigger team. Wasn't closing a round.
It was spending more time on things that create energy.

He already knew the answer. Most founders do.

The gap between a 6 and a 10 isn't more success.

It's less of what drains you and more of what fills you up.

The hard part isn't knowing this. It's giving yourself permission to act on it.

Energy isn't a reward for building something great. It's the requirement.

Design your role, company and life around energy and you become limitless!

Every startup's 2026 budget is already wrong.

Not because someone made a mistake.

Because AI is changing the cost structure faster than anyone can model.

Roles you planned to hire for in Q3 might not be needed by then.

Tools that cost six figures are being replaced by agents that cost hundreds.

Runway is quietly extending at companies that are paying attention.

And the ones that aren't are still hiring against a plan that was outdated the week it was approved.

This is the new reality for founders:

You can't forecast spend the way you used to.

The old was was full of certainty. Full of proven formulas. 

The founders who adapt fastest aren't the ones with the best financial models.

They're the ones willing to revisit assumptions every month, rather than every quarter or every year.

Rigid budgets were already dangerous. In the AI era, they're fiction.

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

Most founders optimize their GTM funnel. Almost none optimize the machine that runs it all.

I recently sat down with Greg Newlands, a fitness coach who works with founders.

Full disclosure: Greg is my coach and also works with several of our Limitless founders.

One thing he said stuck with me:

"If I'm not sleeping well, not exercising, not rested, I just don't perform the same in life or in business."

That's not a wellness quote. That's an operating reality.

Greg trains entrepreneurs the way athletes get trained: 
Strategic breaks throughout the day. 
Resistance training as a non-negotiable. 
Tracking four daily KPIs for energy and performance.

The part that hit hardest: he burned out multiple times before he stopped treating rest as the enemy of progress.

Sound familiar?

This is one of the most tactical conversations I've had on health as a founder strategy.

Full episode on my blog → link in comments.

From your biggest → the best shape of your life | Helping ambitious, driven men rebuild their body & confidence after letting things slip

Jack Dorsey, founder of Twitter and Block, just gave us a lesson in making hard decisions.

Often, when faced with decisions like layoffs, the temptation is to do the minimum necessary. To avoid as much pain as possible. 

Jack did the opposite. He leaned into the pain. He cut 40% of Block's workforce. Over 4,000 people. In one move.

Not because the business is struggling. Gross profit grew 24% last year.

He did it because he saw where AI is heading and decided to get there first. He leaned in.

Dorsey said it clearly: “Repeated rounds of cuts destroy morale, focus, and trust.” He'd rather take one hard, clear action than manage a slow bleed toward the same outcome.

You can disagree with the decision. But the leadership principle is worth studying.

The hardest decisions aren't hard because you don't know what to do. They're hard because you don't want to feel the pain of doing it. They're hard because you resist.

So you delay. You half-measure. You spread the pain out over months, hoping it hurts less.

It doesn't. It just hurts longer.

Whether it's a layoff, a co-founder conversation, or a pivot you've been avoiding, the cost of the slow path is almost always higher than the cost of the decisive one.

Suffering = pain * resistance. If you don’t resist what you need to do, you will not suffer. 

It’s no surprise that Jack took this approach, given his spiritual practice. Jack does long Vipassana retreats. Anyone who has done these will know that they are painful but always worth it.

The way out (of whatever issue you are struggling with) is through. Lean into the discomfort. Make the bold call.

A founder built an AI system that scans everything. It was making him worse at his job.

AI lets you measure everything now. Every Gong call. Every Slack thread. Every data query. Every customer conversation.

One founder I spoke with built an AI system that scans a thousand times more data than his team could manually. Every day, he is briefed on literally everything in his company.

Impressive. Also dangerous.

Because the ability to do everything is not a reason to do everything.

When I dug in, his real bottleneck was one thing. So we cut one of three product initiatives entirely. Narrowed focus to the one thing blocking growth.

More data didn't solve it. Less did.

Here's what I see happening everywhere right now:

AI gives founders superhuman capacity to monitor, measure, and manage.

But capacity without focus is just sophisticated distraction.

The founders who win won't be the ones who do the most with AI.

They'll be the ones disciplined enough to do less.

The mind is a wonderful servant but a terrible master.

For most founders, the mind is running the show.

It wakes you up at 3 am with worst-case scenarios.

It replays the board meeting you can't change.

It tells you that every competitor is ahead of you.

It convinces you that rest is laziness.

The founders I work with at Limitless are learning to think with more intention.

They choose what to focus on rather than letting their minds choose for them.

That's what meditation is. That's what journaling is. That's what a morning practice is.

Not escaping the mind. Training it to work for you, not against you.

You are a mental athlete. You need to train your mind the way athletes train their bodies.

Your mind built your company. Don't let it destroy you in the process.

Every founder has a financial dashboard. Almost none have a biological one.

At Limitless, we think about CEO performance across three dimensions:

Physical → sleep quality, HRV, recovery.

Mental → deep work hours, focus time.

Financial → MRR, pipeline velocity, growth.

(We also go deep on spiritual, but let's park that for now...).

Here's what most founders miss:
These aren't three separate dashboards. They're one system.

✅ Your HRV predicts your decision quality.

✅ Your sleep predicts your deep work capacity.

✅ Your deep work predicts your revenue.

The financial metrics are the output. The biological ones are the input.

Fix the inputs. The outputs follow.

Every playbook you relied on is being rewritten right now.

AI is disrupting how we build, hire, sell, and lead.

The best practices that got you here? Most of them no longer apply.

This is terrifying if you need external certainty to make decisions.
It's freeing if you don't.

When the map is gone, the founder who wins is the one who can navigate without it.

That means first principles over borrowed frameworks. Grounded decisions over reactive ones. Intuition over consensus.

Your own race over someone else's example.

The answers aren't in the latest AI playbook or the hottest thread on X.

They're inside the founder who is clear enough, calm enough, and honest enough to hear them.

This is the era where inner work becomes a competitive advantage.

I meditate every morning before I open my laptop.

Not just because I'm spiritual. Because it makes me a better decision-maker.

When your mind is full of noise, every decision feels urgent. Everything looks like a fire. You react instead of respond.

When your mind is clear, you see what actually matters. You hear the signal through the noise. You trust yourself enough to act without needing five people to validate the call.

The best CEOs I work with are the clearest.

That clarity comes from creating space between the input and the response.

That's all meditation is. Not woo-woo. Not escape.

A daily practice of training your mind to be still so it can be sharp when it matters.

You are a mental athlete. You need to train your mind the way athletes train their bodies.

Ten minutes a day. No app required. Just you and silence. Pay attention to your breath. As distractions arise, keep coming back to the breath. That's it.

It's the highest-ROI habit no one puts on their calendar.

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

CEO, Highland & Haskill Creek • Founder of Classy (acq. by GoFundMe) • Founder of nonprofit, Save Farmland

Every week I tackle management, operations & startup topics that are helping 250,000+ people. Sign up free: www.scotchisholm.com

I also run a leadership accelerator that helps founders develop into top CEOs. Apply here: https://joinhighland.com/apply/

My backstory: 

🚀 Founder of Classy, SaaS for nonprofits raising billions per year

🎗️ Acquired by GoFundMe in ‘22 to create largest giving platform in the world

🌲 Investor in dozens of startups out of family fund, Tall Timbers Holding Co, (Ripple, FanDuel, Hubble, Casetext, etc.)

🏔️ Founder of Highland, leadership accelerator & community for founders

🏡 Co-founder of Haskill Creek, modernized & healthier version of a Walgreens or CVS 

⚽️ Co-owner of Albion Soccer Club, top youth soccer club in country

🧑🏼‍🌾 Founder of Save Farmland, a nonprofit protecting local farmland & food 

⚙️ Industrial engineer & lean six sigma nerd, UMass Amherst grad 

❤️ Board experience: Nature Conservancy, Abundant Montana, Team Rubicon, Street Soccer USA, Montana Pediatric Cancer Foundation

It's been a wild ride. If you're interested in any of the above, please visit my website and reach out to me there. 

www.scotchisholm.com

Scot Chisholm

Here's how to create an unstoppable strategy in 3 simple steps:

First, what is a strategy? Most leaders get this wrong. Strategy is not vision. Strategy is not goals. It's the bridge between the two. Strategy is your unique approach to achieve vision. It shapes your annual goals and daily execution. Vision leads to strategy, which leads to goals.

To create an unstoppable strategy, you need three things:

- Unique approach
- Measurable impact
- Target market

I call this "strategic AIM." A stupidly simple, crystal clear description of strategy that anyone can understand.

1. Approach
What's our unique approach to accomplishing the company's 3 to 5 year vision? Why will people choose us? How are we 10x better than the competition? What are 3 to 5 core bets, multi year initiatives, that we will pursue? Your unique approach creates differentiation at all levels.

2. Impact
What does success look like when we achieve our 3 to 5 year vision? How do we measure it and track along the way? Customer impact, financial impact, shareholder impact. Get crystal clear on what success looks like from day 1.

3. Market
Most leaders target anyone that will buy from them. This is the wrong approach. Instead define exactly who your target market is. Think of it like an archery target. Primary is the inner ring, secondary is the 2nd ring, tertiary is the 3rd ring. Dominate the first before prioritizing the second.

Your strategic AIM informs how you set pricing, packaging, and messaging. It also makes annual goal setting a lot easier. What are the company's top three annual priorities that advance our strategic AIM? Pay special attention to your multi year core bets. These help shape annual goals.

Revisit your strategic AIM at least annually. As your vision evolves, your strategic AIM should evolve. They're joined at the hip. You should always have a company wide strategic AIM, but you could also have one for different products or markets as you get bigger.

If you're a founder or operator and you enjoy my content, you should check out Highland Academy: https://lnkd.in/eAVA5ekz

Operator & Investor • Founder of Classy (acq. by GoFundMe) • Building Highland, Just, Haskill Creek

How to create an unstoppable strategy in 3 simple steps:

In 2017 I was called to my lead investor’s office in La Jolla. 

I had no idea what the meeting was about. 

They wanted me out as CEO after nearly ten years running the company. 

I had missed two quarters and lost their confidence. 

That was enough. 

But they weren’t wrong, I wasn’t yet a great CEO. 

While they tried to push me out, I studied the role like a maniac. 

Determined to be better than anyone that could replace me. 

Ultimately, it worked and the company 5x’d in valuation. 

Now I teach everything I learned through Highland Academy. 

If you’re a founder working to become a great CEO, this is for you.

I'll drop a link in the comments if you want to apply.

Or shoot me a dm.

Don't screw up your annual company kick-off!

Most CEOs don't realize how high-stakes their company kick-off really is. They waste the moment. Why? 

Because they don’t realize how high-stakes it is. They think B- work is ok. Check the box. Get back to the “real work”. I mean, you do have lots of shit going on. Carving out a half-day for a company kick off can feel like a waste of time.

I've been on both sides of this. As a founder, I learned the hard way that the leaders who put their heads down and "get back to work" in January are making one of the costliest mistakes of the year. The annual kick-off isn't a distraction from the real work. It IS the real work.

Andy Grove called this "managerial leverage" in High Output Management. The idea is simple: what you put in is nothing compared to what you get out. A few hours of intentional effort in January can shape the behavior of your entire company for months, if not years. Skip it and you put your team at an information disadvantage you'll be fighting all year long.

The truth is, your kick-off is the highest-leverage meeting of the entire year.
Get it right and your team has the clarity to do their best work all year long. Get it wrong, and you're playing catch-up on culture and alignment for months.

I've worked with hundreds of CEOs on this. The ones who treat their kick-off like the Super Bowl moment it is? They never say die. They show up prepared, energetic, and locked in, and their teams follow suit. The ones who phone it in? They spend the rest of the year wondering why nothing is sticking.

I wrote a guide to follow in a recent newsletter. It includes the one thing your team needs from their leader going into the new year: Purpose, Direction & Progress.

link in the comments to go in depth on this topic 👍

How to speak like the top CEOs on the planet:

Most people communicate: 
- nervousness
- indecision
- selfishness

When they should be conveying: 
- conviction
- thoughtfulness
- partnership

Not all CEOs get it either, but the best certainly do. 

Here’s how 👇 

1/ Keep it clear & simple: Avoid jargon. Use plain English. Be yourself. Don’t over-share or talk in circles. Focus on nailing one main point but never exceed three. Don’t assume understanding. Ask the person if they get it.

2/ Speak with energy: Show enthusiasm & belief in what you say. Avoid fidgeting or whispering. Makes you look nervous. Stay solution-oriented. Don’t be a negative Nancy. You’ll demotivate everyone. Use storytelling to inspire & provide tangible examples.

3/ Talk like a partner: Say “we,” not “I”. Stay relatable to every level of the organization. Create a sense of shared ownership. Ask people: “What do you think?” Take people’s feedback seriously. Even if you make the final call.

4/ Communicate the ‘why’: Tie things back to mission & vision. Always explain reasoning behind major decisions. Help people understand company's progress. Create a sense of urgency when you fall behind. Say “because” more to force yourself to provide context to the team.

5/ Control your emotions: Never let feelings override the message. Stay composed under pressure. Don’t over-share and freak everyone out. But don’t sugarcoat things either. Be realistic & communicate a plan.

6/ Ask the right questions: Don’t pretend to have every answer. Find solutions through thoughtful questions. The best CEOs see themselves as detectives. Practice ‘5 whys’ asking why five times to find root causes.

7/ Guide, don’t dictate: Be a facilitator, not a dictator. Orchestrate debate & discussion. Pre-plan exercises that get people collaborating. Keep the room on track and constructive. Shape the discussion, don’t dominate it.


📌 ps if you want me to teach you how to do this at your company, check out Highland Academy: https://lnkd.in/eAVA5ekz

📌 📌 pps. if you enjoy my content, you'll love my free newsletter. Subscribe here: https://lnkd.in/e6ak5dbP

Helping leaders of all shapes and sizes grow their teams and themselves. 

Every week I tackle management, operations & startup topics that are helping 200,000+ people become better leaders.

Scot’s Newsletter

Highland is a leadership accelerator & community for early-stage founders (seed, series A/B) to develop into world-class CEOs. If you're a founder/CEO, hit me up!

Founder & Chief Professor

A family office with wholly owned businesses, private investments, and property. Ripple, Hubble, FanDuel, CaseText and more.

Managing Director & Founder

After the merger of Classy and GoFundMe, I’ve taken on a strategic advisory role to the CEO & executive team. I remain a large shareholder in GoFundMe and a big believer in our joint vision.

Strategic Advisor, GoFundMe

Haskill Creek is a new type of self-care store. Imagine a healthier & modernized version of a Walgreens or CVS. Family owned business.

Co-Founder

Albion Soccer Club is one of the top youth soccer franchises in the United States with over 10,000 players and hundreds of teams across the country.

Co-Owner

Skills: Agriculture · Food Systems · Board of Directors

Board Member

Save Farmland is a nonprofit organization with a mission to protect and promote small farms in Flathead Valley, Montana, and beyond.

Founder & Chairman

Skills: Nonprofit Technology · Start-ups · Management · Product Management · SaaS · Leadership · Fundraising · Entrepreneurship · Startups · Product Development · Social Entrepreneurship · Software as a Service (SaaS) Founder & Strategic Advisor (Acq. by GoFundMe, 2022)

Founder & Strategic Advisor (Acq. by GoFundMe, 2022)

Classy is a SaaS giving platform that powers the fundraising of over 10,000 nonprofit organizations. Classy is a certified B-Corp, has a team of 300+ people and has raised over $5 billion for social good since 2011. CEO & Founder

CEO & Founder

In Classy’s earliest days, we hosted large scale fundraising events with the goal of connecting millennials with local nonprofits in the San Diego area. CEO & Founder (pre tech company)

CEO & Founder (pre tech company)

Since 1951, The Nature Conservancy has worked to protect the lands and waters on which all life depends. Grounded in science, TNC supports innovation, leadership, and communication for conservation success throughout the world.

Leadership Council Advisory Board

Street Soccer USA is a nonprofit who's mission is to improve health, education, and employment outcomes for the most disadvantaged Americans by using sports to transfer the skills necessary so that they can achieve these outcomes for themselves.

National Board of Directors

Team Rubicon unites the skills and experiences of military veterans with medical professionals to deploy vanguard teams that bridge the gap in disaster response.

For more than 100 years, military, government, and business leaders have turned to Booz Allen Hamilton to solve their most complex problems. As a consulting firm with experts in analytics, digital, engineering, and cyber, Booz Allen helps organizations transform.

Senior Consultant

Operator & Investor • Founder of Classy (acq. by GoFundMe) • Building Highland • Avoid most advice, including my own.

This is where companies quietly fall apart:

Most founders inherit the CEO title before they have any idea what it actually requires. 

You start the company, you get the title. 

No one sits you down and explains what the job is supposed to look like. 

You have to be intentional about learning the role. 

It’s not the same as being a founder. 

Two very different things.

***
Learn what the role of a CEO actually looks like in my recent article (link in comments)

EOS and OKRs broke at scale. 

Here’s what replaced them.

I spent over a decade building Classy from a scrappy idea into a $100M+ company that processed billions in donations before we sold to GoFundMe.

As we scaled, one problem kept surfacing:
No operating system held up past ~$5M in revenue.

We tried OKRs. The product team loved them. But across the company they became too complex. Too many objectives, too many key results, quarterly resets, confusing grading. The system meant to create focus became a recurring distraction.

We looked at EOS. It was cleaner, but too prescriptive. And I didn’t agree with the idea that the founder should hand off operations to a “professional operator.” 

My belief is simple: The CEO must own the operating system.

There was also a deeper issue.

Classy was an impact company. Our mission wasn’t a slogan on a wall. It was the reason people showed up. We needed an operating system that connected purpose all the way down to daily execution, and not just tactical documentation.

So I built one.

It’s called the Northstar OS.

📌ps. If you want to dive into the Northstar OS framework, check out this article I wrote that breaks it down: https://lnkd.in/eDeRw6D2

pps. Sign up for my free newsletter here: https://lnkd.in/gXCsenmP

"Don't worry, you're gonna do great."

I was frozen in the green room at TEDx San Diego. My body felt like 1,000 pounds. I've only been a founder for a couple of years. Why am I giving a TED talk? People are going to laugh me out of this theatre.

An old man in the corner spoke up. That nudge got my legs working again.

I gave my talk. Came back dripping sweat.

"See, I told you you'd do great. You should be proud."

Then he walked on stage to give his own talk.

⁂

Years later, an advisor sent me a book that changed everything about how I manage people.

The One Minute Manager.

I googled the author. Ken Blanchard.

His face stared back at me.

The old man from my TED talk.

Here was one of the most successful business writers of all time, about to give one of his best talks ever, and he was focused on me.

That night I wrote Ken a thank you. He responded with equal grace.

⁂

The book became required reading for every manager at my company. Here are the 3 lessons that changed how I manage people forever:

1/ Great leadership is a side-by-side relationship. Not top-down. It's a partnership. When the organization wins, the people should win. Get this right and your people start managing themselves.

2/ Catch people doing something right. Positive recognition isn't soft, it's smart. People repeat what's recognized.

3/ Correct the behavior, not the person. Address mistakes quickly and specifically. End with reaffirmation. Every 1×1 becomes an opportunity to help people stay on track.

That night, Ken was demonstrating everything he'd later teach me through his book.

True leadership is the smallest acts of support, delivered at the right moment.

Full story + breakdown here: https://lnkd.in/eXTwa8eH

taplio

The Battle

Mark MacLeod

Scot Chisholm

Followers

Posts

Engagements

Likes

Performance ScoreMark MacLeod's LinkedIn Performance

Performance ScoreScot Chisholm's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Mark MacLeod

Scot Chisholm

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);}Mark MacLeod's LinkedIn Performance

Performance ScoreScot Chisholm's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreMark MacLeod's LinkedIn Performance