After working with over 50 business owners as their Fractional CFO, I noticed how some consistently broke through their growth ceilings, while others remained stuck. 

The difference? The ability to understand and ACT on the numbers.

The biggest shocker here is that most businesses still rely on a basic P&L and some messy sheets to track their performance and plan ahead. We're putting a stop to that. With our best-in-class financial models and forecasts, we don't just put our clients back in control, we provid the direct actions to take to run your business without the constant guesswork

Joey Wit

I spent 48 hours at Eddie Maalouf's Agency Founders event.

The value from this will undoubtedly make our clients 7+ figures this year.

Day 1 summary from an Agency CFO POV:

1. Exponential Business Models

Agencies are a pain to scale the traditional way.
(trying to get to 100+ clients at $3K/mo).

What really stood out was how each speaker had their own angle that gave them way higher lead flow, prices or scalability.

None were just selling "email marketing for ecom brands" in isolation.

Examples:
• Jad Al Fakhani was fascinating as he pretty much captured the entire ecom ecosystem in his country. Drivings leads for his agency through his ecom course, and then turning the agency clients into deal flow for his investment company. All combined = 10x better than any in isolation.

• Jem Bourouh had my favourite business model. Instead of building all sorts of funnels, he leverages existing clients (and Ws he gets them) to get more large clients. Turning each client into more clients.

• Manick Bhan was further ahead in the AI Agent wave than any other agency I've seen. Their execution speed and ability to ride this wave are a flywheel in itself.

Takeaway: you must think bigger than your actual service. Find what unfair advantage you have and build that into your model.

2. Headaches per Dollar

I liked this one from Dee Deng 🥊 a lot.

I've always found that as the founder your Hourly Rate is more important than your Profit Margin.

But I like Headaches per Dollar even more. Three ways to focus on this:

1. Data over Opinions: don't waste hours on opinionated discussions. Get the data to back it up or move on.
2. Log Your Decisions: every time you make a big decision/pivot, write it + the reasons for it down. Every couple weeks, review this to see how it turned out. Learn from your W's and L's.
3. From Mina Elias: get a "life manager". This was like Buy Back Your Time on crack. Paying someone $5K+/mo to remove all friction = high ROI.
Got so much more in my notes on this. Will likely make a much longer post on this in the future.

3. Incremental Improvements over Big Pivots

This idea came from Alisha Conlin-Hurd 🧬 her talk on Funnels/Pages.

So much of this was on testing and iteration... creatives styles, hooks, offers etc.

I've seen so many agencies (including myself) jump from offer to offer, or change marketing strategies every couple of weeks.

But nothing will work if you don't test enough.

This was hands down the best event I've been to in the agency space.

I'll share my notes from Day 2 later this week.

And ofcourse follow all people mentioned here. All super high value.

Joey de Wit

Founder of AgenCFO - ROI-obsessed CFO services for agencies and eCom | 50+ clients served | Building own portfolio along the way | Ironman prep 7’26

Three years ago I left banking to start AgenCFO.

Been a wild ride since.

• Worked with over 50 clients (manage $55M+ in revenue now)
• Lived in 10+ countries and settled in Dubai
• Completed 2 Marathons, training for Iron Man

Tested, failed and succeeded with many different offers and strategies over the last couple of years.

But now it finally feels like we truly figured our shit out.

The path is extremely clear:

Scale AgenCFO to 50 active clients → Move into acquisitions (for ourselves & clients) → Grow with the upside we create

I don't want a high-volume "reporting" business. I want a business where we make our clients so much money and add so much value that they can't live without us.

We know how to get there. I just need two more finance pros to make this happen.

If you're either a solo CFO and want to be part of a team again (and never have to do sales again).

Or if you're stuck in a boring finance job and want to actually make an impact and have freedom.

Then send me a DM. I want to speak with you.

Your finance degree got you:

• A mediocre salary & 5% raise per year
• Two weeks' vacation
• Creating budgets no one uses

It could get you:
• Location freedom
• Clients who actually listen
• A cut of the growth you create

Different path. Way better life.

Rarely have I seen an agency "grow into profitability".

If you are at 10% net profit, don't expect to magically get to 25%+ at scale.

It's a sign your pricing, comp, delivery or model is off.

You must know exactly what it is, or you'll stay stuck at 10%.

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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

Scot Chisholm

Getting pushed out of my own company taught me what a CEO actually does...

In 2017, I got called to my lead investor's office in La Jolla.

I waited 30 minutes in the conference room. Then the head of the firm walked in.

"The partners aren't happy with Classy's performance. We think it's time for some change." Two missed quarters. That's all it took.

I had built the company to tens of millions through brute force. But something had gone wrong. Growth slowed. I had become the limiting factor.

I hated them for it. But they weren't wrong.

I was more builder than scaler. More brick layer than architect. It took 24 months to buy them out and get us back on track. Some of the darkest times of my life, but also the deepest reflections.

That experience lit a fire under me to understand the CEO role better than anyone they could bring in to replace me. Not to become the next Jobs or Bezos. But to answer basic questions no one could give me:

What should I be doing all day? What should I focus on? What does a CEO actually do? So I obsessed over studying the best CEOs in the world. What separates the ones who scale from the ones who plateau?

I found that every great CEO masters 7 core responsibilities. I now call them the CEO-7.

I wrote a complete breakdown in yesterday's newsletter. 

If you wanna check it out, I'll drop it in the comments.

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

How defining “great” changed our culture (and decision-making):

A new hire asked me a simple question after onboarding:

“What does great look like here?”

I didn’t have a clean answer.

Not because we lacked ambition, but because we’d never clearly defined it.

Mission, vision, and values weren’t enough.

What we were missing was our perspective on excellence.

That gap pushed us to document our company standards. The non-negotiables that guide decisions when things get messy, fast, or ambiguous. Inspired by how Patagonia articulated its philosophies, we created standards that outlived leadership changes and scaled with the company. 

Here's how I defined them 👇 

***
ps. If you want to read my in-depth article I wrote on this exact topic, I'll drop the link in the comments.

How to define what great looks like:

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

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 👍

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

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