🐧 Q&A on Building a Portfolio Career

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

• 🗺️ My journey from burned-out tech worker to semi-retired portfolio careerist
• 🤑 How to earn 2.5x-5x your hourly rate through your part-time work
• 🦺 1-2 Rule for safely transitioning to a portfolio career
• 🎢 Why loneliness and income volatility are hidden costs of solopreneurship

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💼 Q&A on Building Portfolio Careers

Growing up in a hard-working immigrant family in Michigan, I saw my parents struggle with financial insecurity.

This experience lit a fire in my belly to pursue what I thought was the pinnacle of success:

A high-paying tech job in Silicon Valley.

I achieved my version of the Silicon Valley dream:

• Working as a product manager for companies like Dropbox
• Tripling my income in 5 years
• Enjoying perks like free meals made by Michelin Star chefs

But despite this outward success, I felt empty and burned out.

The turning point came after Dropbox's IPO. While I was heavily recruited by top companies, I realized I was chasing others' dreams, not my own.

After doing some inner work (harder than it sounds!), that’s when I decided to align my life with my top values like freedom, curiosity, and adventure.

I quit my job to travel to 20 countries, worked for a fintech unicorn in Singapore, and built a portfolio career that has allowed me to:

• Earn 2.5x-5x my hourly rate from part-time consulting
• Launch the online education business I’ve wanted
• Be semi-retired by covering my expenses
• Learn Spanish in Mexico City
• Spend 6 months in Vietnam

In short, I “work to live” instead of “live to work.”

But my journey taught me that working and living on your own terms comes from pursuing your own definition of success.

I’m excited about helping others build their own portfolio career, so they can also align their life with their values like I did.

Recently, I received a few questions from readers about solopreneurship and portfolio careers. In this newsletter, I will share my answers to the most popular questions.

‍

Q: What inspired you to try a portfolio career? What else did you consider, and why did you ultimately go with a portfolio career?

There were 2 factors related to my decision to start a portfolio career:

Career goals and personal finance.

Factor 1: Career Goals

As I wrote in this piece on quitting my 9-to-5 job, I had been dragging my heels on this decision for a while.

Since I started working in the internet industry, my goal was always to pick up the skills and knowledge to build a portfolio of my own profitable businesses.

For ~10 years, I worked for growth-stage startups and a public company.

As a marketer, product manager, and product leader.

By 2023, I felt like I had checked off what I set out to learn in my tech career.

It felt like a natural next step to leverage my skills, knowledge, network, and capital into ownership.

Hence, going from professional to business owner.

Factor 2: Personal Finance

After a decade of working, I had an asset at 33 that I didn’t have at 23:

Financial security.

More specifically, I had achieved my semi-retirement number.

I spent the last decade sufficiently funding my investing accounts.

Assuming a 5% real interest rate compounded over the next 3 decades (until I’m 63), they would cover my traditional retirement spending:

This level of financial security freed me up to take more risk and pursue work I enjoy.

And the work I currently enjoy is:

• Building the online education business I’ve talked about doing for forever
• Writing, teaching, and helping others on money and portfolio careers
• Advising fintech founders & execs on building great products

Other Potential Pathways

I considered a few other options to achieve greater ownership:

1. Start a VC-backed company
2. Join as a startup executive
3. Invest in startups or SMBs
4. Buy and operate a profitable business
5. Invest in real estate

Each option comes with its own trade-offs:

1. Start a VC-backed company → I work with some VC partners I respect and don’t have anything against taking VC money. I just don’t think it’s a good fit for the type of businesses that I’m interested in building (online education, business services).
2. Join as a startup executive → This is one of the best risk-adjusted paths for achieving positive monetary outcomes in the startup world. However, the level of ownership wasn’t sufficiently high enough for me. Plus, this is an extra full-time commitment.
3. Invest in startups or SMBs → This is possible to do as a part-time income stream, but it’s very hard to do well unless if you’re deeply involved in the startup or SMB worlds. I experimented with angel investing, but didn’t find it fulfilling and typically it doesn’t generate consistent cashflow. So I’ve paused this.
4. Buy and operate a profitable business → This starts very full-time, but can transition into part-time work once stabilized. It also has good cashflow potential. This is applicable for a subset of businesses I’m interested in (e.g. business back-office services). I’m still exploring this pathway.
5. Invest in real estate → This is possible to do as a part-time income stream. As of now, I’m not interested in actively investing in real estate due to the sweat equity involved. I do passively invest in real estate (REITs, private funds).

In summary:

I have tabled (1), (2), and (3), while I’m still exploring (4) and (5).

But the beauty of a portfolio career is that I can choose to incorporate these income streams into my cashflow-generating portfolio.

‍

Q: What have been the best, worst, and most surprising parts of a portfolio career?

I’ll start with the worst parts for me:

• Loneliness. As a solopreneur, I work with a couple great contractors, but sometimes I miss having a full-time team - getting feedback, planning together, etc. To fill the gap, I started joining masterminds and support groups with other solopreneurs. My goal is to eventually hire and build a team.
• Volatile income. Portfolio careers built off of consulting are not for the faint of heart. It’s not uncommon to go from earning way more than you did in your FT work one month to $0 the next month. And vica versa.
• Selling yourself is hard. You are the product you’re selling. You are the product you’re marketing and promoting in the market. This didn’t come naturally for me. But I now view brand-building, promotion, and sales as a key part of the portfolio career game.

Now here’s the best parts:

• Unlocks my “work to live” lifestyle. I have optimized for keeping an uncluttered calendar, minimal meetings, working remotely, choosing clients I like, and doing the type of work I enjoy. It’s not perfect, but for the first time in my life, I have time freedom without sacrificing my finances.
• I make good money, while having fun. I feel like I’ve figured out the right balance. My portfolio career has 3 income sources:
  1. High-leverage work like consulting and advising - 2.5x-5x my hourly rate
  2. High-joy work like writing and teaching, which despite making less money, feels incredibly rewarding when I do
  3. Passive income like investment income & royalties
• Working on my own terms. I don’t feel like taking a meeting? I don’t take it. I don’t want feel like writing this morning? I do it tomorrow. On the flip side, my client talks about how I positively impacted them? I feel on cloud nine because it’s entirely my creation.

Finally, the surprising bits:

• It takes longer than you think. I hate to say it, but I naively thought it’d take much less time to achieve what I did with my newsletter and cohort. But I now know just how much work goes into building an online education business—especially in today’s competitive marketplace.
• Your positioning will evolve—a lot. When I started Money Abroad, I focused on money for expats. Now, this has shifted to designing your own money path by building a portfolio career. When I started consulting, I worked with any Series A/B startup. Now, I have doubled down on fintechs.

‍

Q: What advice do you have for someone who’s considering a portfolio career?

Follow a margin of safety and the 1-2 Rule before quitting your 9-to-5.

Quitting your job too early is a common mistake.

Before you quit, plan your finances strategically.

Here’s my 1-2 Rule:

• 1 year of living expenses saved
• 2x of your monthly expenses covered from your business income

Build a margin of safety by:

• Growing your side hustle while working your 9-to-5 job
• Leveraging geoarbitrage to reduce costs
• Saving up a cash buffer

Prioritize cashflow-generating work like consulting and services before investing in content and products.

I talk to many aspiring solopreneurs who want to create content and build products.

Instead, I suggest nailing your cashflow machine first.

Consulting and services are typically how I have seen people accomplish this.

After you build up a nest egg, then you can use that to invest in content creation, product development, or other longer-term initiatives.

Otherwise, since you’re bootstrapping, you risk running out of money before you generate sufficient cashflow from your longer-term efforts.

Save yourself the anxiety or stress of worrying about runway.

Build the cashflow machine first.

Start broad, then niche down.

Linkedin influencers will tell you to niche down, down, down.

This assumes you fully understand your market.

In my consulting and coaching, I didn’t know about the market initially. So I benefited from starting out broad to test different hypotheses and learn about the market before narrowing my focus.

For example, I started off working with any Series A/B startup.

But over time, I discovered that fintech companies are where I add the most value and the ones most interested in my services.

‍

Q: Which projects have been most revenue-generating for you? What have you learned about making money with a portfolio career?

Here’s my income sources by % of revenue (roughly):

• 80% Consulting and Advising
• 15% Courses
• 5% Sponsorships and Affiliates

Clearly, my consulting still generates the bulk of my revenue.

What I have learned about making money with a portfolio career:

1. Build your cashflow machine first. Consulting helped me establish consistent source of income. The reality is that I wouldn’t be able to do Money Abroad without it.
2. Content and digital products take at least 6 months to monetize—even longer to scale. I didn’t receive my first sponsorships and affiliate revenue until ~6 months and ~3k subs into the newsletter. I didn’t start monetizing the course until ~11 months into the newsletter. This jives with what I’ve heard from other solopreneurs and portfolio careerists.
3. You need to create value AND scarcity. You quickly learn that your niche is highly competitive. Yes, it’s important to provide value to your clients, but competitors can also provide value. It’s just as important to deliver value ONLY you can deliver. This scarcity helps to drive economic demand.

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Q: What’s next for you professionally? How does a portfolio career fit into those goals?

My long-term goal is to build a thriving portfolio of:

• Actively managed cash-flowing businesses
• Passively managed investment income

My portfolio career helps me to reach this goal.

It gives me flexibility to ramp up and down income streams based on my career goals, financial situation, and lifestyle needs.

For example, over time I want to decrease the reliance on consulting as a % of revenue. Last year, I set a goal to achieve 50% revenue from non-consulting sources. I still have a ways to go to reach this target.

🌐 Beyond your borders

🏡 Mortgage rates dip, giving U.S. homebuyers over $200,000 in additional spending power in some U.S. cities (CNBC)

🔎 Solving the Mystery of an Investment That’s Too Good to Be True (WSJ)

🧑‍💻 Tech Jobs Have Dried Up—and Aren’t Coming Back Soon (WSJ)

🧠 Social snippets

Taking a break from socials this week due to traveling and prepping our cohort kick-off.

For daily insights, follow me on Linkedin or Threads.

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