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

𝗧𝗿𝗮𝗻𝘀𝗳𝗼𝗿𝗺𝗮𝘁𝗶𝘃𝗲 𝗚𝗿𝗼𝘄𝘁𝗵 𝗖𝗼𝗮𝗰𝗵𝗶𝗻𝗴 𝗳𝗼𝗿 𝗙𝗶𝗿𝘀𝘁-𝗧𝗶𝗺𝗲 𝗙𝗼𝘂𝗻𝗱𝗲𝗿𝘀
It’s not just about scaling your business.
It’s also about scaling you.
From Fortune 500 companies to fast-growing startups, I’ve coached leaders at every stage. Today, my mission is focused: helping first-time founders scale themselves as fast as they scale their companies.
 
𝗠𝘆 𝗙𝗼𝗰𝘂𝘀
Your startup can only grow as fast as you do. As a first-time founder, you’re under pressure from investors, your team, and your family—all while learning on the fly skills that others spend decades mastering. Whether you’re raising capital, hiring your first team, or pushing toward product-market fit, I help you close the gap between where you are and where your company needs you to be.
 
𝗪𝗵𝘆 𝗠𝘆 𝗔𝗽𝗽𝗿𝗼𝗮𝗰𝗵 𝗪𝗼𝗿𝗸𝘀
I bring 20+ years of coaching 10,000+ leaders, founder experience, and cutting-edge insights from neuroscience and behavioral psychology. The result: a proven path to accelerate both personal and company growth. My frameworks help you:
• Transform self-doubt into clarity and influence
• Build and inspire high-performing, durable teams
• Raise capital while staying true to your vision
• Create sustainable success without burnout
• Leverage your existing strengths while closing critical skill gaps
• Grow yourself as fast as your company 
 
𝗪𝗵𝗼 𝗜 𝗦𝗲𝗿𝘃𝗲
My one-on-one clients are founders who:
• Want tailored, responsive coaching that meets them where they are
• Care deeply about building strong teams and cultures
• Aim to create both impact and enterprise value
• Refuse to accept that success means sacrificing their families, health, or lives outside the company
• Are willing to grow personally and professionally to become the leader their company needs 
 
𝗥𝗲𝗮𝗹 𝗜𝗺𝗽𝗮𝗰𝘁
From doubling revenue to unlocking fundraising rounds to transforming team dynamics, my clients consistently achieve breakthrough results—while building lives they actually want to live.
 
𝗪𝗮𝗻𝘁 𝘁𝗼 𝗖𝗼𝗻𝗻𝗲𝗰𝘁?
Visit www.andrewpoles.com/contact or DM me here.

Andrew Poles

This is one of those leadership truths that sounds simple and may take years to embody. Early on, being the hero feels like care, competence, and responsibility. Over time, it quietly becomes a ceiling. 
The real work is shifting from proving your value to building others’ capacity and confidence. 
When people grow stronger around you, leadership stops being exhausting and starts being expansive.

Coaching first-time founders to grow themselves and their companies | 3x Founder | 22+ years coaching partners like NASA, Dell, Schwab + 10,000 people worldwide

Your success, my mission | CEO @ Polished Carbon | Former CIO $4B company | DEIB ally | Sharing 25 years of hard-won wisdom on people-first leadership + emotional intelligence + self-mastery

Leadership isn't about being the hero.

It's about creating heroes.

You don't earn your team's respect by showing off
your superpowers.

You earn it by helping them discover their own.

Because true leadership is seeing potential
in someone before they see it in themselves.

Then showing them how to unlock it.

It's not about:
➟ Being the smartest in the room
➟ Solving all the problems
➟ Having every answer

It's about:
➟ Asking the right questions
➟ Drawing out hidden talents
➟ Building confidence in others

Your legacy isn't measured by your achievements.

It's measured by the people who grew
stronger under your guidance.

Remember:

Great leaders don't create followers.
They create more leaders.

That's the privilege of leadership.
That's the responsibility.
That's the gift.

Your superpower isn't what you can do.

It's what you help others become.

♻️ Agree? Repost to share with your network.
🔖 Follow Justin Wright for more on leadership.

You and me against the problem - never you against me, or me against you.

That is a key shift that allows for productive disagreement between cofounders.

How many times do we find ourselves at odds over some issue or decision with someone with whom we share decision making or execution responsibility, and then quickly, the disagreement over the issue becomes a break in the relationship inside of which we're attempting to work out the issue? 

What I find works is to practice - it's always you and me against the challenge. Never one of us against the other. 

In marriages. In co-founder dynamics. In Board meetings. On teams.

You & Me. 

Check out the full interview. Link in the comments.

It was great to be interviewed on The Secrets of the High-Demand Coach podcast with Scott Ritzheimer. 

We dove deeply into the issues of co-founder tension, how to run a business when you disagree, covering situations where one co-founder has more legal control than the other as well as situations where control is shared and decisions must be agreed upon. 

Having seen several co-founder relationships blow up unnecessarily over challenges of disagreement, I know how challenging this topic can be to navigate. 

I’d really love if you gave this episode a listen.

Open article: Podcast Template with Scott Ritzheimer – Ep. 0–duplicate-1 by scalearchitects.com

Podcast Template with Scott Ritzheimer – Ep. 0–duplicate-1

Who knew we could learn so much from trees about how to build powerful companies?

In this interview with Scott Ritzheimer of the Start, Scale and Succeed Podcast, we explore the intricacies of co-founder dynamics and how to successfully navigate some of their thornier aspects.

Part of our discussion centered on what I feel is a hidden secret to greasing the gears of performance - human connection.

Do you tend to the quality of your connections with the people you partner with and lead? 

If not, you might want to reconsider. 

For the full interview, see link in the comments below.

Most founders I work with are running on a fuel they never question: chronic dissatisfaction.

It drives results–but it also quietly burns you.

This article introduces a different fuel for elite performance–one that keeps your edge without costing you your health, relationships, or joy. 

If you’ve ever felt afraid to slow down or feel “good enough,” this is for you.

Most leaders I work with are driven by a deep, often unspoken fear: If I let myself feel satisfied, I’ll lose my edge. We’ll stop pushing. There will 

Open article: And Why “Satisfaction” Isn’t the Answer Either by Andrew Poles • 4 min read

And Why “Satisfaction” Isn’t the Answer Either

The holidays are supposed to feel whole.
But for a lot of leaders, they don’t.

Old tensions with teammates.
Unspoken resentment with a cofounder.
Judgment you’re still holding against yourself for a decision that didn’t work.

This issue isn’t about being “nice.”
It’s about forgiveness as a leadership skill–and why it might be the thing that restores trust, clarity, and momentum in your company heading into the new year.

If relationships at work feel heavier than they should this holiday season, this is for you.

The word holiday comes from holy day. And before “holy” was a religious word, it meant something simpler—and deeper: set apart, venerated, whole, unbr

Open article: The thing that actually nourishes collaboration gets buried under performance, pressure, and expectations. by Andrew Poles • 4 min read

The thing that actually nourishes collaboration gets buried under performance, pressure, and expectations.

This proverb keeps coming back to me.
Not because it dismisses sorrow - but because it draws a clean line between *experiencing* it and *living inside* it.
We don’t get to control the thoughts or emotions that pass through on a hard day.
We DO get to choose whether we let them take up residence and start shaping our identity, our decisions, or our future.
That small pause - one breath, one reset - is often the difference between wisdom and rumination.
And over time, those pauses compound.

NYT Bestselling Author | Entrepreneur | Investor

This proverb lives rent-free in my head.

(read it once and you'll see why):

"You cannot prevent the birds of sorrow from flying over your head, but you can prevent them from building nests in your hair." - Chinese Proverb

If you attach yourself to the sorrow, continue to think all of the negative thoughts it brought about, repeat the patterns of your past, dwell in the pain, and bemoan your bad luck, you allow the nest to be built.

If you pause, breathe, give yourself a moment to reset, and choose a balanced response, you send the birds flying off into the distance.

The choice is yours…

—

♻ Repost to remind someone: don’t let sorrow build a nest.
🔔 Follow Sahil Bloom for more life wisdom like this.

—

📌 Want 50 simple rules for living calmer and clearer?

Download my Most Powerful Life Hacks PDF (free) and join 800,000+ who get my newsletter: https://lnkd.in/edxXi82t

This is a solid reminder that momentum doesn’t come from hype - it comes from clarity. 
Looking back honestly isn’t about judgment; it’s about separating what actually worked from what just kept you busy. 
The quality of 2026 will be shaped less by new goals and more by how cleanly you integrate the lessons from 2025. Reflection done this way becomes a strategic advantage, not a sentimental exercise.

Founder at Bloomful | Helping founders and execs build a credible LinkedIn presence | Keynote Speaker, Medical Doctor, Ex-BCG

Your strongest 2026 starts with a brutally honest look at 2025.

Growth always demands reflection.

Future successes depends on the questions you ask today.

7 powerful questions to supercharge your 2026:

1. Where did you show resilience this year?
↳ When did you prove your strength or resilience?
↳ Use resilience to tackle bigger challenges in 2026.

2. Who supported your growth this year?
↳ Who made a real difference to your growth?
↳ Invest in meaningful relationships to fuel success.

3. What fears held you back this year?
↳ What stopped you from acting on what mattered?
↳ Stop avoiding fears; face them head-on instead.

4. Where did you excel & create impact?
↳ What moments made you feel proud of your work?
↳ Lean into strengths to have bigger impact in 2026.

5. What brought you the most joy this year?
↳ What moments or people made you happiest?
↳ Prioritise what lights you up to build a fulfilling '26.

6. What would you do differently in 2026?
↳ What choices would you approach differently?
↳ Turn the lessons into a smart strategy for next year.

7. What vision will guide you into 2026?
↳ What inspires you when you imagine life in a year?
↳ Let a clear, bold vision drive your decision making.

As the year wraps up, taking time to reflect
Helps set the stage for a successful 2026.

What’s your top tip for reflecting on the year?
Let me know in the comments below👇

📌 If you like this content, you might like my free newsletter—sign up here: https://lnkd.in/ekfMRpWJ

♻️ Repost to help others plan their best year yet.
➕ Follow Dr. Dupe Burgess for more.

7 Powerful Questions To Supercharge Your 2026

What's the answer to unequal co-founder, or decision maker, authority?

What do you do when one co-founder will have the ability to overrule the decision in nearly every case? Is that a workable situation?

That depends, but the work of determining if this can be a workable agreement mostly falls on the co-founder or decision maker who is ceding authority to their partner.

It can work if the right work gets done IN ADVANCE.

Otherwise, I've seen this situation broil, and turn into co-founder resentments that can cost you the company.

For a full discussion on how to navigate co-founder tension, see the full interview with Scott Ritzheimer on his podcast Start, Scale and Succeed. 

Link in comments below.

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Andrew Poles

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