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.

Just posted my interview with Vitaly Pecherskiy , CEO of StackAdapt.

The company went from 170 to 1,600 employees in 5 years. Crossed $500M in revenue. Bootstrapped early, then raised from tier-one growth investors.

Three takeaways:

✅ Own your destiny: When VCs passed early on, they built product and got it in customers' hands fast. That forced self-reliance became their operating DNA.

✅ Don't raise too early: Many founders overestimate TAM, raise too much capital, then can't grow into the valuation. By the time they exit, their shares are worthless. Vitaly delayed raising until traction proved the market was real.

✅ Product > Marketing: When asked about the state of advertising, Vitaly flipped it: "Great marketing is easier when you have a great product." Marketing teams should sit closer to product and influence its direction.

The full conversation covers scaling culture across 20 countries, transitioning to CEO after 9 years as co-founder, and building a $500M+ business without the typical VC playbook.

Link in comments and you can find it where ever you catch your podcasts.

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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

CEO and Co-founder at StackAdapt

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

I'm giving up the one thing that's been holding me back.

For years, I've had a love/hate relationship with alcohol.

I LOVE champagne. I love the ritual. I love wine. I have studied it. 

But I know it's bad for me.

For years in my journal, I've noted how alcohol lowers my vibration. It holds me back.

I've decided to take a pause. One year. Nothing.

I'm sharing this for accountability. This will be hard.

I'm making a public promise to myself. I know it's the right thing.

As I help CEOs become limitless, I need to remove the thing that creates limits for me.

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If you think HR is just about hiring and firing, you haven't met Christine Song 

I just published my conversation with Christine, a multi-time Chief People Officer who's built strategic HR functions across corporate and startup worlds.

She breaks down what most founders get wrong about people:

→ Why HR needs to earn its seat at the table (not demand it)
→ How to speak truth to power, even if it costs you your job
→ Why investing in high performers beats fixing underperformers
→ The trap of hubristic hiring ("fat and happy" vs. high-performance)
→ How to build systems that scale people, not just product

Christine doesn't sugarcoat it. She's the leader who tells the CEO what they need to hear, not what they want to hear.

She recently launched 5 to 9 Society, an invite-only network for elite operators. The kind of confidential, backdoor conversations that actually move business forward.

Everything in your business comes down to people.

If you're not treating people strategy as seriously as product or revenue, you're limiting your ceiling. See comments for the interview link.

Most CEOs make a fatal mistake when fundraising: They don't go for the NO. 

When I was a VC, I invested in 4% of the deals I saw. Imagine the deal flow of a partner in a top tier fund. You have to assume they are going to pass. Not because your company is bad. Just basic probability.

Too many CEOs waste so much time. They think a first pitch means interest. It doesn't! Even a 2nd meeting doesn't necessarily mean they are interested.

Andrew D'Souza, founder and CEO of Boardy (the company that I assume every single founder in N. America now knows...) recently shared his series A deck. It's not going to win any design awards, but it has a slide that I love:

Reasons NOT to invest.

Andrew calls it out. In fact, he begins the deck by stating what you need to believe in order to have conviction. Then later on he shares all the reasons not to invest.

I LOVE this. At FreshBooks, when we raised a growth round we had an entire presentation on the reasons not to invest. Of course, it was a bit of propaganda. We highlighted the reasons and then offered mitigating diligence. 
Still, we put the issues out there.

You need to do this when you raise. Don't hide them hoping they won't be found. You're just wasting time.

Go for the NO. Filter down rapidly to the investors who LOVE what you are doing.

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Founder of Boardy • Founder of Clearco (Clearbanc)

❌ "I'm a technical founder."

❌  "I'm not a sales guy."

❌  "I'm an introvert."

The moment you say these things, you've just built your own ceiling.

Every label is a limitation.

Your company needs you to evolve. Fast.

The role you played at $1M ARR won't work at $10M.

The leader you were with 10 people won't cut it with 100.

Stop defining yourself by what you were.

Start asking: Who do I need to become?

You have no limits except the ones you impose on yourself.

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Most CEOs set annual goals for their "Sunday self." The one who's rested, worked out, meditated, and firing on all cylinders.

But here's the truth: That's not the person running your business 90% of the time.

Real life is full of random Tuesdays. You wake up tired. An employee quits. Your kid is home sick. The deal you were counting on falls through.

This is your real baseline.

If you design your targets around your absolute best days, you're making it impossible to win. Because peak performance is rare. Consistency is what actually moves the needle.

Set goals for the version of you that shows up on a regular Tuesday in March, not the unicorn version that appears once in a while.

That's the person who gets you to December.

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The secret of my success has been following the same practice as Steve Jobs.

At his funeral, every guest received this book: Autobiography of a yogi. This is the story of Yogananda, the yogi who bought kriya yoga to the west.

The word “kriya” means “complete action”. Kriyas are yoga movements combined with breath work and breath locks. They are designed to create, move and stabilize energy. 

I discovered kundalini yoga, a form of kriya yoga, in 2012. I got serious about it in 2019. I now teach it. Kundalini yoga is the foundation of my life. Every day begins with practice. I see yoga not as the time on the yoga mat, but how I live my life. 

Kundalini is an energy practice. We all have dormant energy at the base of our spine. Through these kriyas we access this energy.

Studies have shown that this practice can turn on dormant parts of our brain. 

Why do I share this?

Despite being 2% of our body’s weight, our brain uses 20% of our energy. That’s for the average person. Imagine how much harder a founder’s brain works?

Energy is the key to your life. Energy is key to all of your dreams for your company.

It takes energy to create something from nothing. It takes to energy to create then keep up with massive growth.

If you want to turn your vision into reality, design your role, company and life around energy maximization. Kundalini yoga is how I did this. It has changed my life. 

Find the path that works for you. Make energy your top priority.

You wouldn't lead your company drunk.

So why are you leading it sleep-deprived?

After 17 hours awake, your brain performs like you're at 0.05% BAC.

That's legally impaired in most places.

Yet many CEOs run on six hours of sleep or less.

Sleep impairment is costly:

- 3x more likely to get sick
- 50% slower reaction times
- Triple the risk of diabetes
- 3.5x higher risk of hypertension

And these are the visible costs. The invisible cost is something you deal with non-stop. Chronic stress. Inability to think clearly. Lack of energy. Complete absence of joy.

Sleep deprivation doesn't just hurt you. It hurts your company. It hurts your family.

Worse decisions. More conflict. Weaker creativity. Higher burnout on your team.

You're not being hardcore. You're being inefficient.

What's the solution?

Treat sleep like your most important meeting. Non-negotiable. Seven hours minimum. Track it and improve it like any key metric in your company. This metric is the one that moves your company metrics.

Your brain compounds decisions daily. Sleep is how you clear the cache.

Limitless CEO knows: recovery isn't weakness. It's strategy.

Protect your sleep. Scale your capacity.

P.S.
Here's a random photo of my dog. If you need sleep lessons, she is the one to speak with...

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The best B2B brands are stealing from B2C playbooks.

My latest podcast guest proves it.

Reza Khadjavi (CEO of Motion) helps advertisers cut through the noise by combining science with creative that actually stops the scroll.

His journey includes:
✅  Disrupting his own agency to build Motion
✅  Navigating multiple AI waves and disrupting himself  again in the process
✅  Cracking the code on what makes creative work in today's noisy ad market

His biggest insight? B2B companies need way more consumer DNA in their marketing.

Most B2B brands are still playing it safe. Meanwhile, the ones winning attention are treating their audience like... humans.

See comments for episode link.

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CEO at Motion

You're not just a leader. You're a mental athlete, whether you realize it or not. 

Let's look at real athletes for a second.

They train obsessively. They perfect every move. They review their game tape. They have coaches, routines, and recovery days.

Their goal? Show up on game day at their absolute best.

But CEOs? You're expected to compete all day, every day. You never get "practice." You rarely hit pause.

That's a problem.

Here's where athletes have it right:

✅They don't just compete. They rest and review. 

✅ They don't go all out, all the time. They peak, then recover.

✅ they get real coaching and invest in support systems.

Want to level up in 2026?

Start treating yourself like a true mental athlete.

1. Prioritize physical fitness. Sleep, exercise and nutrition aren't "nice to haves" , they're high-performance tools.

2. Make rest strategic. You're paid to make decisions. Your mind needs clarity, not constant grind.

3. Review your performance. End each day with three questions: What went well? What didn't? What did I learn? Simple, powerful.

4. Get support. Every top athlete has coaches. CEOs need them too. Don't do it alone.

Personally, I use what I call my BOS (Business Operating System). It's a running chat, where I do my daily review, track patterns, and adjust my game.

If you've raised venture capital, the pressure to perform is real. Expectations are sky high.

So manage yourself like an elite athlete. Practice. Rest. Get support.

You'll be shocked at the difference this will make next year.

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The founder burnout myth nobody wants to admit:

If you're grinding 80-hour weeks, burnout isn't a risk. It's a certainty.

We love stories of founders at Meta, Stripe, Airbnb. We hear about their non-stop hustle, so we copy them. But there's a catch most people miss.

Those teams didn't just work hard, they started winning. And once you're winning, everything shifts.

Momentum changes how you feel. When your company becomes the market leader, the market pulls you forward. You wake up energized. You see results. The work fuels you. Your company has escaped gravity. Everything gets easier. 

But until then? You're just burning fuel to escape gravity. That's where most startups get stuck. The grind is unavoidable at first, but endless grind with no lift-off drains you, fast.

If you're still working endless hours and nothing feels lighter, you're not lazy. You're running out of energy because you haven't "escaped gravity" yet. And you can't brute-force your way through forever.

Here's the real dirty secret: The difference between burnout and breakthrough is simple. Progress.

Naval Ravikant said it best: "Startups die when founders run out of energy."

If you're not feeling the pull, stop pretending hustle is enough. Diagnose and work the problem. Be brutally honest. 

Ask yourself: "knowing everything I know about this company would I start it today"?

This question ignores sunk costs. It doesn't matter how long you have been at it. If the answer to this question is no, it's time for change.

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Most founders I meet are obsessed with the gaps.

What's broken. What's missing. What needs to be fixed.

They've trained themselves to scan for problems. It's how they got here.

But it's also stealing their joy.

You can't appreciate what's working when you're in constant high alert.

You miss the privilege of building something from nothing.
You miss the team that showed up and crushed it this quarter.
You miss the customer who just renewed because your product changed their business.

You're cutting yourself off from energy that actually fuels performance.

The irony? The CEOs who pause to appreciate what's working solve problems faster.

They're not stuck in anxiety. They're thinking clearly. Making better calls.

Gratitude isn't soft. It's strategic. It is an endless source of energy.

When you're grateful for the privilege of solving hard problems, you show up differently.

You stop chasing perfection and start creating momentum.

The gap will always be there. That's the nature of growth.

But so is everything you've already built.

Both are true. You get to choose which one you focus on.

The founders who last don't just optimize for performance.

They optimize for what makes the journey worth it.

Joy and gratitude are strategic.

Joy and gratitude will make your life better.

Joy and gratitude are self-fulfilling. The more you focus on them, the more you get of them.

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Last week I asked a CEO to declare schedule bankruptcy.

Blow up your calendar. Start from zero.

His days were back to back. No time to think. No time to execute. Just reacting.

"But these are all important meetings." Sure. But what are you optimizing for?

Your calendar should solve for two things:
1. Energy
2. Impact

Not accessibility. Not being helpful. Not keeping everyone happy.

Energy and impact.

So he is rebuilding from scratch.

What stays:
- Activities that leverage his unique superpowers
- Activities that give him energy
- Deep work blocks for his top strategic priorities

What goes:
- Status update meetings (send a doc)
- "Quick syncs" (usually not quick)
- FYI meetings (you don't need to be there)
- Networking coffees with no clear outcome

What gets blocked:
- Deep work blocks (energy)
- Exercise (energy)
- White space (both)

I can't wait to see the impact this has on his energy and the momentum of his business.

Most CEOs are calendar broke and don't know it.

You're spending time you don't have on things that don't matter.

Schedule bankruptcy isn't radical. It's necessary.

Your calendar is your strategy. Make it solve for what actually moves the business forward.

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Nobody on their deathbed wishes they worked more.

Yet here we all are, looking for ways to squeeze more hours into our weeks. 

There's a disconnect here. Something that we will likely regret in the end. 

The fix isn't working more. It's wasting less. So much of our time is wasted. Fix that and we don't need to search for more hours.

Stop tolerating:
- Chronic stress, fatigue and brain fog. You are not meant to live this way
- Meetings with no agenda
- Toxic team members
- Leaders who can't keep up with the company
- Projects that don't move the needle
- Interruptions disguised as "collaboration"

Start protecting:
- Your morning for deep work
- Your energy for what matters
- Your boundaries from urgency addiction

The limitless CEO doesn't outwork everyone. They outthink them. 

Limitless CEOs focus on physical, mental and spiritual health first. This gives them more energy, focus and inspiration. They direct that at unlocking the growth in their companies (and themselves). Creating a virtuous cycle.

Your company needs your creativity and energy, not your exhaustion.

Build the habits that expand what's possible without burning out.

That's the unlock. This is what we are doing Limitless.ceo

Limitless.ceo

Founders: stop pricing your deals for perfection.

Jason M. Lemkin just broke down the Brex acquisition: a $5.15B exit that's being called a "failure" because it's below their $12.3B peak valuation.

Think about that. A $5B exit. In 8 years. Called a failure.

This is what happens when you raise at valuations that require top 0.1% outcomes. You lose optionality. Jason calls these deals "hubristic". That nails it.

The problem isn't the capital. It's the expectations.

When you raise at $12B, a $5B exit isn't a win; it's a disappointment. The mercenaries who joined for paper gains leave. The narrative becomes "what went wrong" instead of "look what we built."

And it's happening again. Worse this time.

AI startups raising $2B seeds at $12B valuations. Before shipping products. Multiple funding rounds in one year. 3-4x markups in months.

Each round narrows your definition of success.

You're not just raising capital. You're setting the bar for what "winning" means to your team, your investors, and your ego.

A $3B exit sounds amazing—until you raised at $10B.

The founders who maintain optionality:
- Keep expectations grounded in reality
- Attract missionaries, not mercenaries 
- Preserve multiple paths to success
- Don't need perfection to win

I have raised over $1B in venture capital over the years. I never once went for the highest valuation. I always solved for the most aligned investor and the deal that would enable me to sleep at night.

Price for success, not perfection. Keep your options open.

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Here's how to get ahead of 99% of other founders:

Build a daily learning loop.

End each day with 4 questions:

1. What did I do well today?
2. What could I have done better?
3. What did I learn?
4. What adjustments do I need to make tomorrow?

Five minutes. That's it.

Most founders never do this. They just keep going. Same patterns. Same blind spots. Same results. 

The ones who scale themselves faster than their companies? They extract the lesson before moving on.

They notice when a decision worked, and why.
They catch patterns in what's not working before it becomes a crisis.
They adjust in real time rather than when something breaks (most often it is the founder that breaks).

The best founders go through compound learning.

Each day builds on the last. You get sharper. Faster. More deliberate.

Start tonight. Four questions. Five minutes.

That's the difference between grinding and growing.

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We read a lot about the big outliers. The multi-billion $ market leaders. That's interesting but not relevant. That's not your world. And it's not my world. 

It's far more relevant to hear stories from founders who are closer to our reality.

Blair Livingston founder of Street Context is a story teller like no other. I was enthralled listening to his journey. I wanted to be sitting by a campfire.

There is so much actionable and inspirational goodness in the episode. 

Check out "The Startup CEO Show" where ever you catch your podcasts.

Episode link in the comments.

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Tinkering at Contextual Markets

Darrell Heaps took Q4 public. Then took it private with PE. 

18 years leading one company through every stage of growth.

Most founders don't make it past Series B. Darrell stayed in the CEO seat through IPO, private equity, and exit.

He was on the podcast last year. If you missed it, here's what he learned:

✅ Going public isn't the finish line. It's a new set of constraints. Quarterly pressure. Public scrutiny. Different growth expectations.

✅ PE brings capital and operational rigor. But you trade some control for expertise and resources.

✅ Leadership evolves. What got you to $10M won't get you to $100M. You have to grow faster than the business or you become the ceiling.

Darrell stayed focused on customer value through every transition. Product-market fit at scale. Revenue growth is the unlock.

Not chasing trends. Not optimizing for the fundraise. Building something durable.

If you're a B2B SaaS founder thinking about what comes after Series B, this interview is worth your time.

Link in comments.

The real reason you can't sleep? You're trying to finish the workday in your head after hours.

Most CEOs lie in bed replaying conversations, solving problems, planning tomorrow. That's not insomnia. That's unfinished business.

When I was at FreshBooks, this happened to me all the time. I called them "freshmares" (FreshBooks nightmares).

Your brain doesn't care that it's 11pm. If you didn't close the loops, it will close them for you.

Spend 10 minutes at the end of your work day:
- Do a quick review: what went well today? What did not? What did I learn?
- Write down what's unresolved
- Capture tomorrow's priorities
- Acknowledge what you completed

Ideally this work day should end hours before you want to sleep.

You need a simple closing ritual to signal to your body that you are done. 

Even though I work from home, I change my clothes when my work day is done. I get outside if it's nice out. I change my context completely.

Your brain needs permission to stop working.

Give it that before you ask it to sleep.

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Most CEOs are running on fumes by 2 pm.

Burnt out. Scattered. Making decisions that matter with zero energy left.

I used to be the same. Until I rebuilt my day around energy, not efficiency.

Here's what changed:

No meetings before noon:

Mornings are for deep work. Writing. Podcast recording. Program design. This is when my brain works best. I protect it ruthlessly.

I work out before lunch:

This resets me. I'm not grinding through the afternoon. I'm starting fresh with full energy for my clients.

I batch my coaching calls:

All client work happens in the afternoon. I'm in flow state. Full focus. No context switching between a coaching call and a budget review.

I stop when the work is done:

Not when I'm exhausted. When my priorities are complete. Then I actually rest.

Sleep is non-negotiable:

Same bedtime every night. Wind-down ritual. Today's performance started with last night's sleep.

This isn't about discipline. It's about design.

Your calendar either protects your energy or destroys it.

Most CEOs let their calendar happen to them. Then wonder why they're making million-dollar decisions at 6 pm when they're mentally done.

You can't scale a company faster than you can scale yourself.

Start with energy. Everything else follows.

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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

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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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Performance ScoreMark MacLeod's LinkedIn Performance