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

• ⚒️ 5 side hustles that I’ve launched to generate over $100,000

• 🧠 4 lessons I learned from my side hustle successes and failures

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🛣️ My $100k Side Hustle Journey

A few weeks ago, I was invited to speak by the Berkeley Club of Singapore.

I shared my journey to making over $100,000 from my side hustles taking 10 hours/week.

I uncovered my successes and failures.

In this newsletter, I’m going to recap my side hustles and 4 lessons I learned building them.

Side Hustle #1: Tea e-commerce + tea tasting service

Full-time:

In 2013, I started my tech career in San Francisco. I turned down a Google offer to join a startup doing marketing. Later, my manager gave me the opportunity to internal transfer from marketing to product management.

I joined Dropbox as a growth product manager to learn from the best in the industry, helping grow the business through its IPO.

On the side:

My friend and I started a tea e-commerce, selling sampler tea boxes for people to try new loose leaf teas. We took 6 months to ship our first product. (Don’t do this.)

Vitamins vs painkillers:

We quickly learned that demand wasn’t there. Outside of a handful of repeat customers buying the boxes as a gift for friends. So we shelved this product after selling ~50 units. Tea sampler box was a vitamin.

Then, I tested hosting local tea tasting events. This service generated more buzz than I expected.

I unintentionally uncovered a pain where San Francisco tech professionals felt bored and lonely. They had disposable income but desperately lacked social, novel things to do. Tea tasting was a painkiller.

Side Hustle #2: Career coaching

Full-time:

In January 2019, I quit my full-time job to take a travel sabbatical.

For the first four months, I enjoyed work-free travel. I volunteered on tea farms, took surf lessons, and joined a Mandarin intensive program.

Then, I missed working. So I decided to experiment with a side hustle I had considered for years: career coaching.

On the side:

Back in San Francisco, I did a strengths exercise and discovered several of my peers thought of me as a coach.

Meanwhile I was also very curious about careers. In my 20’s I loved to discuss nerdy career books like Startup of You or So Good They Can’t Ignore You. And so I combined my strengths and curiosities.

In June, I joined Hireclub, a coaching marketplace platform. I took my first intro calls from Osaka, Japan. I recall feeling nervous and made tons of mistakes (more on this later). But despite this, I felt myself growing. So I kept going.

In July, I got my first paid client. Then a second. And third. Initially, the money wasn’t lucrative. But I got hooked on the magic of making money online on my own schedule.

While traveling to 10+ countries, I grew to over 30+ 5-star reviews and moved off the platform to start a private practice. This enabled me to customize my offer and charge higher prices (more on this later).

This was my first experiment with carving out an independent portfolio career.

Side Hustle #3-#5: Consulting, advising, affiliates

Full-time:

In March 2020, I moved to Singapore and joined Xendit. I wanted to challenge myself to grow my tech career internationally.

For a full-time product role, I looked for:

• leadership/management role

• build 0-to-1 products

• work in emerging markets

I’m grateful that I found this with Xendit. During my time there, I helped grow the payments platform in Indonesia and Philippines from $4B to over $15B TPV.

In 2023, I left and started my entrepreneurial journey.

Ever since college, I wanted to learn to build online businesses, so that I could eventually build my own. This was what drove my decision to move to San Francisco.

That’s why once I felt like I had enough financial runway, I decided it was now or never. And I pulled the trigger. (I’ll write more about this decision in a future edition.)

I started Money Abroad, which has evolved from a content to course business.

On the side:

Before and during working at Xendit, I built my private practice for career coaching.

I redesigned my coaching offer, which increased perceived value and commanded higher price. Then, as I helped clients achieve more results, I started getting more inbound referrals.

While I built Money Abroad, I paused career coaching and launched more complementary side income streams:

• Product Consulting for B2B startup clients

• Advising a few startup founders on PLG growth and product

• Affiliates for various financial software and services

Along this journey, I learned multiple lessons on building successful side hustles:

Lesson #1: Start broad, then go narrower than you think

Think you’ve got a niche? Think again. Narrow it. Then narrow it down again.

Let’s take my career coaching:

• My offers started out very broad. I did career discovery, promotions, mock interviews, negotiation, you name it. I did it. Obviously, I felt overwhelmed. But I also learned what I liked and was good at.

• Then I narrowed down to job search. I got more clients, but this was still too general. Differentiation was hard.

• After interviewing my clients, I discovered they shared common traits like making a career transition in the tech industry, living in a US major city, and first or second-gen immigrants.

• Armed with fresh insights, I designed a 3-month program that helped clients (mainly, career pivoters) win their tech dream job. I also refined my positioning to potential clients on my website and discovery calls, which helped me increase my close rate and pricing.

Hence, I started broad, then went increasingly more narrow as I learned what I liked, was good at, and clients demanded.

Each time I thought I had narrowed enough, I could still narrow a bit further.

Next, on why offer experimentation is crucial:

Lesson #2: Experiment constantly with your offer design

Earlier, I mentioned my Tech Dream Job program. This was a structured offer, taking clients through the end-to-end job search process.

Through this program, I ended up help people make transitions like going from non-tech to tech, agency to in-house, startup to FAANG, and even moms getting back into the workforce.

But it didn’t start this way.

I started out with hourly calls and did not have a cohesive offer.

Then along my journey, I tested offers like:

• 30-minute and 60-minute calls

• Monthly subscription with X calls

• 3-month package (Tech Dream Job program)

In the end, what I liked best was long-term packages designed around a clear benefit.

Why?

• Attracted serious, long-term minded clients who I enjoyed working with

• Pricing was rarely an issue for potential clients

• More time for deeper strategic work

• Less need for constant lead gen

I shudder to think about what if I stuck only to hourly calls.

Testing constantly led to improving my packaging, pricing, and positioning over time.

Now let’s talk about the #1 question I get: “how do I get clients?”

Lesson #3: 50% Rule - Half of side hustlers get their 1st client from referrals or network

I discovered the 50% Rule through my own lived experience and other side hustlers.

My first 4 product consulting clients:

• Client #1: Referral from a VC friend

• Client #2: Referral from a colleague

• Client #3: Direct network; founder friend expressed interest

• Client #4: Inbound; founder contacted me via personal website

As you can see, 3/4 came from referrals or my immediate network.

After reviewing over 20 side hustle case studies, my team and I discovered that ~50% of them got their 1st client from referrals or immediate network.

While this isn’t a statistically significant sample size (yet), this rule is actionable.

The point is to first tap your network for potential clients and promoters to your potential clients.

Finally, you’ll exhaust your network at some point.

Then, it’s time to invest in building relationships with strangers:

Lesson #4: Cultivate your leads through content, speaking, and lead magnets

In my service-based side hustles, I’ve connected with potential clients through 3 sources:

• Content - Writing Linkedin content, blog posts (and even this newsletter) to capture attention and generate interest in my offers.

• Speaking - Doing talks for startups led to prospects for consulting and angel investing that I otherwise wouldn’t have had.

• Lead Magnets - Sharing free resources (e.g. a Career Positioning Exercise) led to building my email list and eventually discovery calls.

These are sources that anyone can leverage to reach potential clients for free. Moreover, you can differentiate yourself through them.

In conclusion

My side hustles:

1. Tea e-commerce + tea tasting

2. Tech career coaching

3. Product consulting

4. Startup advising

5. Affiliates

My lessons:

1. Start broad, then go narrower than you think.

2. Experiment constantly with your offer design.

3. 50% of side hustlers get their first client through referrals or network.

4. Cultivate your leads through content, speaking, and lead magnets.

🌐 Beyond your borders

🤔 Do What You Love and the Money Will Follow...IF: (link)

🏎️ The $645,099 business pivot (link)

📈 How Does Inflation Impact Retirement? (link)

🛍️ What purchases have the least diminishing marginal returns? (link)

📆 How I can help

That’s all for today!

Whenever you’re ready, here’s how I can help you:

For daily insights, follow me on Linkedin and X (@dexteryz)