Hey readers,

Thanks to everyone who voted! The top-voted topic was pricing, but it was a close call. This worked well, so I’ll include polls periodically :)

Today, in 10 minutes or less, you’ll learn:

• 💰6 pricing strategies I learned on my path to earning 2x-5x my hourly rate

• 💎 How to pick the right pricing tier before you design your service

• 🧮 Two proven pricing formulas (plus when to use each one)

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💰️ How I'd choose the right pricing model (starting over)

In the last 2 years, I’ve earned between 2x-5x my hourly rate through consulting work.

But I made lots of mistakes along the way - especially when just starting out!

From undercharging and leaving thousands of dollars on the table to struggling with creating a right-sized package.

The biggest mistake? I think it’s starting with the service I wanted to deliver, then hunted for clients willing to pay for it.

Today, I’ve flipped my entire approach.

Instead of starting with my service, I start with the PRICE:

• The category I want to play in

• The pricing tier (high, mid, low-end) of the category to start with

• Expected value of competitive offers in this pricing tier

THEN I work backwards to my value prop and offer design.

And that’s just the tip of the iceberg.

In this newsletter, I'll walk you through the 6 pricing strategies I'd use if I were starting my portfolio career over today.

Let’s dive in:

1/ Pick your pricing tier 💰️ 

Choose your category and pricing tier first.

Take men’s haircuts as an example.

Here’s the pricing tiers you might find:

If I were starting a barbershop, the first thing I’d do is pick a tier.

The reality is you get very different clients and expectations for each tier, which necessitate different solutions.

If I want to command a high-tier price, then I better be ready to offer personalized styling and luxury comforts because that’s the expectation that clients have at this tier.

Your pricing tier influences things like client definition, value, and solution complexity.

2/ Work backwards to your offer 🔄

Now design your service to exceed the expectations of that pricing tier.

Ask yourself:

• What is the “table stakes” experience for this pricing tier?

• How can I deliver 10x ROI on this pricing tier?

When working with a Series B fintech startup on enterprise activation, I identified significant bottlenecks in their client onboarding flow. Making improvements could dramatically accelerate time-to-value and reduce enterprise churn—delivering ROI that made my 5-figure engagement a no-brainer.

3/ Define building blocks of your offer packaging 🧱

Now I would define the 3 offer components to fit the pricing tier:

• Value: the specific problem you’re solving for the client

• Method: How you’re delivering that value (e.g. workshop, project-based, fractional, advising, etc.)

• Interface: How clients experience your service (online/remote, in-person, etc.)

IMO be specific and firm with the value, but flexible on the method and interface.

I had a call with a startup founder, who wasn’t sure if he needed a fractional CPO, advisor, consultant, etc. He just knew he didn’t want to make mistakes shipping the wrong thing or being a bottleneck for product development. We started with these problems and then guided him to the right method (it was advisory in this case).

4/ Choose your pricing formula ⚙️ 

Here are two approaches I would use, depending on the situation:

Time-based pricing:
Best for less defined scope or fields accustomed to hourly rates, e.g. software development.

Start with your desired annual revenue, then work backwards to your hourly rate:

• Annual revenue: $50,000

• Come up with a time constraint: 500 hours per year

• Estimate billable hours (60% of hours): 300 hours per year

• Calculate hourly rate: $166

• Add taxes (e.g. 7.65% for US self employment): ~$179

Outcome-based pricing:
Best for structured projects and retainers tied to client results. If you help them generate $100k annually, charging $10k is a no-brainer.

Here’s how I run the numbers:

• Scope a project and estimate the number of hours: 50 hours

• Take your hourly rate x hours, then add 40% to account for scope creep and other surprises: (50 x $179) x 1.4 = $12,530

Chase Damiano (Founder of an operations agency) and Mark Mullinix (Fractional Head of Growth) both preferred value-based pricing over quoting hourly rates. To anchor on the outcome, Chase might say something like:

Few other thoughts:

• IMO there’s nothing wrong with selling your time, especially when you enjoy the work! I’m tired of the social media blasting the message “selling your time is society’s biggest con” (yes that’s a real headline). If you enjoy doing something and you get paid for it, that’s a positive thing.

• Define a tangible client outcome even if it’s a retainer. Aman Manik (Product Consultant) prefers project-based pricing vs retainer-based pricing because the value is clearer to clients. Aligning on client outcomes will help your client measure if the engagement was a success or not. Hint: This will be crucial during renewals!

• You’ll likely shift your pricing over time. Sergio Pereira (Fractional CTO) shifted from hourly rates to monthly retainers as his engagements got longer (6-18 months instead of 1-3 months) and relationships deepened.

5/ Break everything into milestones 🎯

I’ve seen large numbers stall sales discussions. If you’re doing something in operations you might breakup the work into 2 chunks:

• Month 1: CRM system audit and plan ($10k)

• Month 2-5: Implementation ($40k)

Each milestone corresponds to a specific deliverable. This makes the overall project feel more digestible.

Sophie Syed (Fractional Customer Ops), shared how she performed a paid audit first of Hubspot systems, delivering clearly scoped problems and a high-level action plan to fix them. Then the client could decide whether or not Sophie is the one to actually implement this (vs an internal team or other vendor).

6/ Consider pricing vs terms ⚖️ 

I forget where I heard this, but in any negotiation, you can negotiate either pricing or terms.

In fractional/consulting work, I view the latter being more important than the former to help you solve cashflow and flexibility.

Consider:

• Payment due dates: net 7, net 30, net 60

• Payment schedules: 100% upfront, 50% upfront 50% upon completion, 100% upon completion

• Working hours: 2 hours/workday, 10 hours/week flex days

In my experience:

• My engagements have spanned between net 7 to net 30 terms. I would NOT go any higher than that.

• I’ve done a split of 100% upfront and 100% upon completion. Most companies with mature finance processes tend to pay upon completion, while startups may be more flexible. Hint: Don’t reject the client because they don’t pay upfront!

In Summary

When I started my portfolio career, figuring out pricing was confusing. It’s so much more variable than negotiating salary for a full-time role.

Here are the pricing strategies I’d use if starting over:

• Start with pricing tier, not services

• Work backwards to exceed tier expectations

• Use 3 building blocks for offer packaging

• Choose the right pricing formula

• Break large projects into digestible milestones

• Negotiate terms, not just price

Hope that helps you win right-sized deals that you’re proud of!

Thanks for reading! What did you think of this piece? Reply and let me know your thoughts.

💎 Last Week’s Gems

🏖️ BI: Death of the Digital Nomad. A recent analysis from Indeed found that job seekers' interest in foreign roles declined steeply between 2024 and 2025. Fascinating data!

🏹 Guide to Positioning with Multiple Products and Personas by April Dunford, OG positioning expert. While it’s meant for companies, I think a lot applies to portfolio careers, fractionals, and entrepreneurs.

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Community Spotlight: Chris Laxton

Chris is a Fractional CFO for early-stage startups & co-founder of Foundational, a fractional C-suite services and headhunting firm. Previously, he worked in finance for corporates like Deloitte. He’s based in Singapore.

How would you describe what you do to someone outside of your industry?
I work with founders of early-stage companies to help them understand their finances better and use them to grow better.

What triggered your interest in exploring the portfolio path?
I've always been drawn to working with earlier-stage companies and found that working as a Fractional CFO is the best way to do that. I've always been someone who enjoys pushing myself and learning, and so working with multiple companies at different stages allows me to learn much more than working at a single company at a time.

What’s your current portfolio career mix?

1. Fractional CFO work

2. Running Foundational and managing other Fractionals

What advice would you give to someone starting a portfolio career?
Make sure that you're comfortable with pitching yourself in 30 seconds or less. Understand where you can bring the most value and set boundaries to ensure you can focus on that work.

What’s a fun fact about you?
I play sports or exercise on average 5 times a week—I love all sports and exercise. I've found it's the best way to keep me sane and destress.

What's one piece of media that impressed you lately?
📰 Secret CFO newsletter

How can people connect with you?
LinkedIn

P.S. Did you enjoy this spotlight? Hit reply and let me know—or suggest another amazing portfolio pather we should feature next!

💌 Reader Notes