🔑 How to Run Portfolio Career Experiments (Like a PM)

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Today, in 5 minutes or less, you’ll learn:

• 🧪 Why treating your portfolio career as a series of small experiments beats the "go big or go home" mindset
• 💡 2 real-world case studies from my life (including exact revenue numbers)
• 🎯 A practical 6-step framework to test new (portfolio) career paths without risking it all

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🧪 How to Run Portfolio Career Experiments (Like a PM)

“Go big or go home.”

Which path do you choose?

Society loves catchphrases like this that glorify the all-or-nothing leap into the unknown. Take a huge risk… or crawl back under your comfortable weighted blanket.

But there’s a third way.

Treat your portfolio career as a series of small experiments.

In my 11-year product career, I've run hundreds of experiments on websites, mobile apps, software, emails and more.

Hypothesis-driven testing has grown into one of my favorite tools of the proverbial product toolkit.

But not only this, applying this tool to my career changed my life.

Whether you’re building a portfolio or FT career, I believe anyone can leverage this tool. And doing so can feel empowering.

Instead of asking, "But what if I make the wrong choice?"

You’re flipping the question, “What hypothesis should I validate to increase confidence in my next move?”

Instead of obsessing over achieving a huge outcome…

… you give yourself permission to take many tiny actions that accumulate over time into massive results.

In this newsletter, I’m going to deep dive into how I leveraged experiments in my portfolio career, the 6-step experiment framework, and how you can implement them in your own life.

Alright - let’s get this party started by first showing you how my IRL examples:

📰 Case Study #1: Monetizing My Newsletter

In 2023, I launched Money Abroad, a newsletter on expat money, as a small experiment.

Over the next 6 months, we organically grew subscribers 43% MoM:

My Google Doc Growth Tracker

While this growth didn’t mean I had a viable business yet, it was a positive signal.

The content seemed like it had some market pull.

As a next step, I knew readers liked the content, but I didn’t know if they’d be willing to spend money on related products/services.

And so I put this to a test by running a monetization experiment:

Question

I asked myself the question:

“What value would readers be willing to spend money on (that I also enjoy delivering)?”

Hypothesis

Then I tested multiple hypotheses over the next 6 months:

• Personalized expat tax service
• Tailored expat coaching
• Simple expat stock investing workshop
• Step-by-step remote side hustle cohort
• Easy-to-use expat personal finance tool affiliates

For example:

“If I offer a personalized, pain-free expat tax service, then readers will be willing to spend money on it and I will enjoy delivering the service.”

Variant

While not a pure A/B test, each offer became its own variant that I could test sequentially as offerings for my newsletter subscribers and Linkedin audience.

Success Metric

I used revenue generated and let’s call it a “binary enjoyment score” as my primary indicators.

For example, with the expat tax service, I calculated revenue as my cut from my tax partner after the tax season is over.

Or with the remote side hustle cohort, revenue generated from the beta program enrollments.

Results and Learnings

So how’d it go? In the end, the following happened over the next 6 months:

‍

Here is what I learned:

1. Expat coaching and remote side hustle cohort demonstrated the most market pull. The latter sold out beta seats in ~48 hours.
2. For coaching, I realized I didn’t like coaching on cross-country job search or relocation. Too many confounding variables + few people are serious about relocation.
3. I also balked on complex financial topics—turning down $1,000’s more from a potential client ready to go because I didn’t feel comfortable with guiding people on expat taxes, business structuring, etc.
4. Expat tax service + personal finance tool affiliates were enjoyable to work on, but difficult to get conversions. For the latter, we had 45 tax service inquiries, but only 4 paid clients (9% conversion rate).

Next Steps

As a result, I decided to double down on my cohort program.

Over the next 12 months, I funneled my limited resources towards testing and expanding the cohort program, which evolved into Part-Time Consulting Launchpad.

Now we’re running the 4th cohort (opening for enrollment tomorrow)!

Here’s another example:

🤝 Case Study #2: Testing My Service-Client Fit

As a long-time product builder for software/internet industries, I started getting inbound inquiries for interim product leader and advising opportunities.

At the same time, I saw friends like David Fallarme step into interim and advising roles, and speak to their potential.

That’s when I decided to experiment with offering my services in startup networking conversations and events.

Question

This time I was curious to learn about which clients I’d be the best match for:

“What client profile would find value and be willing to spend for my product advisory?”

Hypothesis

I roughly thought fintech and SaaS startups would be a good fit given my background:

“If I verbally discuss my offer with founders, investors, and connectors at networking sessions, then fintech/SaaS startups founders would be most interested in my product advisory.“

Success Metrics

I measured success through my number of leads and client engagements.

Variants

Here I was really testing two different versions of a pitch:

1. For fintech startups
2. For SaaS startups

Results and Learnings

Over the next few months, I discovered a surprising result:

The majority of my client engagements turned out to be with fintech Series A/B founders—which made sense given my background.

However, I also started a couple of engagements with corporate fintech leaders. For example, the innovation department of a national bank in charge of 0-to-1 and new products. I discovered that their teams’ challenges felt like deja vu with what I’ve faced the past.

This opened up my eyes to where else my experiences may be valued and transferrable.

Next Steps

While my bread and butter are still growth-stage startups, I’m going to test if I can attract more corporate engagements.

This might look like exploring new GTM channels and testing tailored positioning for serving corporates. And it’ll give me the chance to gain more confidence in if I enjoy this line of work.

Now that I’ve uncovered two experiments in my own life, let me break down the career experiment framework itself:

🔄 6 Steps of a Portfolio Career Experiment

You’ve already seen these steps in the above examples, but here is how I define them:

‍

Makes sense?

Now that we’ve walked through the 6-step process, here’s how you can implement experiments in your own life:

✅ Get Started in 30 Days

Ready to run your first portfolio career experiment? Here's what to do:

Reply with:

1. One hypothesis you want to test in the next 30 days
2. How you'll measure success
3. Your timeline

I read every response and love helping people design their experiments.

P.S. Want to start testing your portfolio career hypothesis soon? Sign up for my Part-Time Consulting Launchpad waitlist (enrollment opens tomorrow!)

P.P.S. Know someone stuck at a career crossroads? Forward them this email.

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