🐧 Building a tech portfolio career | Aki Taha

INSIDE: What is a Portfolio Career, APAC vs US Careers, Doubling Down vs Diversifying
November 5, 2023

Traditional careers are dead.

Aki has led talent teams in the US, SG and all over the world for companies like Netflix, Uber, and Google.

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

  • 🛣️ How Aki Went from Silicon Valley Talent Director to Building Teams in APAC to Launching TalentStories
  • ⚖️ Key Difference Between Successful Careers in APAC vs US
  • 💼 What is a Portfolio Career, When Aki Chooses to Double Down in His Career vs Diversify His Bets
  • 👨‍👩‍👧 How to Balance Careers as a High-Achieving Couple

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💼 Building a Tech Portfolio Career | Aki Taha

Aki Taha led recruiting in Asia at Netflix, Uber, and Google. Worked for Dropbox and Greylock Partners in the US. He’s passionate about injecting business savvy into talent people, and people-savvy into business leaders.

He’s a long-suffering NY Met fan and Arsenal supporter, born in Nigeria 🇳🇬 , raised in New York 🗽, lived and worked in Palestine 🇵🇸, Guatemala 🇬🇹 and China 🇨🇳, and has called Singapore 🇸🇬 home for the past 10 years.

In 2021, he left Netflix to start TalentStories, a talent content, advisory and learning company.

🛣️ Tell us about your career journey from Silicon Valley Talent Director to building talent teams in Singapore to launching TalentStories.

Early on, I was (literally!) all over the map!

I dabbled in different roles, industries and countries, and within 3 years of graduating college I’d interned and worked in marketing, HR, finance, operations and recruiting roles:

  • At a big bank in NY
  • At a car company in Beijing
  • At a software startup software in Austin, Texas
  • At a medical non-profit in Guatemala City
  • At a recruiting agency in San Francisco

The experimentation eventually led me to hone in on the People function.

To go deep on recruiting and talent, and on tech as an industry. It led to roles at Google in the US and China, to working at Dropbox and a venture capital firm in Silicon Valley. And to moving to Singapore 10 years ago, where I worked first for Uber and then for Netflix, getting to set up their earliest teams in the region.

Finally, two years ago I started my own company, TalentStories: I now write a weekly newsletter that explores the changing world of work, and how we respond and adapt to it, and I consult and advise organizations that need to build and lead world-class teams.

🇸🇬 You’ve led hiring teams for well-known tech companies like Netflix, Uber, and Google in APAC and the US. What have been the similarities and differences you’ve observed between successful careers in APAC vs the US?

I’ll caveat that I’ve mostly worked for US-based companies in APAC, but the ingredients for career success in the US and Asia share a ton in common.

The people I’ve seen thrive in both regions—regardless of where they’re from, where they’re based, or the type of org they work for—tend to be:

  • Deeply driven
  • Adept at building networks internally, and externally
  • Willing and able to take healthy risks
  • Often have a diversity of experience, broadly-defined

One thing I learned to index on in APAC (less relevant in the US):

Experience living, working or studying in places other than the one you were originally from.

Having hired in Asia for Google, Uber and Netflix, that trait consistently led to great hires at each of those companies, despite their different cultures and business models.

That’s not to say we didn’t hire amazing talent who had only lived in one country!

But time and again, people who had experienced different places, cultures and contexts, who had been forced into the discomfort of a new place and forced to adapt, did well at the companies I worked at.

💼 You’ve built a portfolio career. Explain what is a portfolio career, pros and cons, and why you decided to pursue this path?

A portfolio career embraces the reality of modern careers as open-ended, complex, and unpredictable pursuits.

It recognizes that we will be making many, many bets over the course of our careers, so it prizes awareness and intent as key levers for making increasingly smart, compounding bets that are more likely to lead to outsized career success.

The moment you begin to appreciate that our careers are creative, open-ended “hit making” businesses, all the investment concepts kick right in:

  • How do I build a “thesis” -- i.e. a belief or an awareness of what I will be good at, and enjoy doing?
  • What career capital can I acquire that compounds to outsized effect? (Network, reputation, technical and/or soft skills, etc.)
  • How and when do I bet “big”, or double down via a job or career move?
  • When do I need to toss in the cards (i.e. move on) from a career move or investment?
  • How do I manage risk over time, or at any given moment of time in my career?

💪 How would you answer the question: when do I bet “big”, or double down via a job or career move?

Generally, doubling down and concentrating is wise during a boom, because your time becomes more “pricy”.

By the same logic, it often makes sense to diversify and explore in a downturn, because your time is relatively “cheap.” You also have more plausible deniability during a downturn: it’s easier to “defend” tangential career moves and the learning they lead to.

Outside of paying attention to the macrocycle, signs you should double down include things like the company you are working for is growing really fast, you are able to deploy your career capital (expertise, skills, relationships, reputation, etc.) in a really high impact way — which almost always also means you are enjoying the work you are doing.

Conversely, when growth is slower, your impact is lower, and/or you are enjoying the work less, there are now diminishing returns to your effort, so it could well be a sign that you should explore something new. The cost of doing so is lower, and the upside of working on something you will enjoy more, of building new relationships, new skills, etc — is now higher.

  • My years at Google are an example of this doubling down. Early on Google’s growth was off the charts, and I was working on something I was good at, and enjoyed: recruiting. The returns compounded accordingly (brand, impact, skills, reputation).
  • Then, when my impact and learning as a recruiter began to plateau, and when the 2008-2009 financial crisis hit, I wound up diverging or diversifying — I moved into a new role, as an HR Business Partner at Google. It was a low-risk chance to pick up new skills, new relationships, work on new problems.

📕 5-minute journal exercise

For the journaling fans, Aki’s questions make good writing prompts:

• Are you doubling down or diversifying in your career? Why?
• When does it make sense to move on from what I’m actively pursuing?
• How do I manage risk with what I’m actively pursuing?

👨‍👩‍👧 Many readers are interested in portfolio careers due to their ability to balance with family. As a married couple with kids, how do you and your partner make career decisions together?

I think of it as escalating levels of awareness:

Your early adulthood years are about you:

  • What do you want?
  • What do you want to work on?
  • Where do you want to live?
  • Who do you want to be with?

Then, if you meet a partner with whom you want to build a life with, you embark again on the same questions, but this time as a couple:

  • What do we want?
  • What do we want to work on?
  • Where do we want to be?

As with your own career and life, the goal is awareness. But this time it’s couple-level awareness.

In practice this means learning to communicate, trade off, compromise and sacrifice for one another.

TalentStories meet-up in Singapore

Another goal is intent: 

Knowing you’re making certain life and career decisions together, having considered the options together -- and making your bets together. Then learning from the outcomes of those bets together, to be able to bet better and smarter the next time around.

Of course, this goes beyond just the jobs you each hold over time; it extends to decisions around the country or city you bet on together; to the type of schooling you might choose for your kids, etc.

My wife and I discussed for years whether or when she might take some time off. And for as many years, she continued on in her roles. But we were having the conversation together. Then, at some point, the timing became “right”, and she decided to take that break.

Fast forward, and she ultimately decided to go back to work. When she did, we discussed that it might be feasible for me to start a company at some point in future. A year later, I decided to take that plunge.

The idea is that it’s impossible to know in the abstract when these moves will make sense.

But by having the conversations together, understanding the tradeoffs and downsides and benefits of different decisions, and achieving some form of collective awareness, you’re more likely to be able to make a healthy decision together, when the opportunity arises.

You’re more likely to recognize the timing as “good” — or at least, as good as it’s going to be. :)

The same goes for an individual. The risk is the unexamined life, or career; it is allowing ourselves to bounce, Pachinko-like, from one job or life decision to the next, without intent or awareness.

😨 What are mistakes you’ve made in building a portfolio career?

Not knowing I was actually in a portfolio career was my biggest mistake. Continuing to think about my career in a linear way, even when all the evidence was in front of me, from the moment I graduated: this is going to be a messy, bumpy ride!

Had I had this kind of framework and awareness, I still would have screwed up over the course of my career.

And to be clear: the goal here is not to not screw up!

On the contrary, it’s to screw up, but to do it with awareness, and to learn from those screw-ups.

Concretely then, more mistakes:

  • I should have paid more attention to skills and experiences that compound (examples: I should have focused on writing way, way earlier on in my journey. I should be doing more online networking in this phase/during this relatively online career bet I’m making, etc)
  • I should have better appreciated the experiences I had neglected as simply “random”, or even as failures.
  • I should have more readily “folded my cards” and cut my losses, in jobs or roles where I was not learning or growing.
  • I should have taken on more risk, more often, and earlier on.
  • I should have appreciated better the long, long time horizon I’m on.

🫶 What counterintuitive or non-obvious advice would you give to people looking to build a portfolio career?

It wouldn’t just be advice to people looking to build a portfolio career. It’s advice to anyone with a career, and it’s fundamentally counterintuitive, because of how linearly we continue to approach how we build them:

ALL of us are building a portfolio career, whether or not we’re doing something openly “creative”.

Whether or not we have side hustles, or multiple hustles.

The rare exception might be someone like a doctor, who in the US and many other parts of the world, goes through a highly prescribed, linear, step-by-step process to become a doctor.

For the rest of us: our careers are defined by uncertainty, and this will become even more so the case going forward. We can choose to ignore this, and navigate our careers linearly. Or we can embrace the randomness inherent to navigating our careers -- and learn how to bet. 🙌🏻

🏠️ Where can we go to learn more about you?

🌐 Beyond your borders

🎧️ Contrarian Money and Writing Advice: As a writer on money topics, I loved this podcast episode with Morgan Housel on the Tim Ferriss show. 16:24 marks one of my favorite segments, where Morgan shares the critical insight that led to his “Rich and Anonymous” post (link)

🇸🇬 Middle-income earners in Singapore outpaced others in salary growth (link)

🏠️ 10 money traps to avoid when investing in property (link)

🇺🇸 Why Americans are leaving to become digital nomads in Mexico (link)

🗺️ X marks the spot

Hamptons doing an anonymous net worth survey amongst our members.

One question we asked: what level of wealth are entrepreneurs most satisfied?
 
According to early data: $5-$10 million net worth.
 
We say most satisfied because so far, there's no level where people stop… twitter.com/i/web/status/1…

— Sam Parr (@thesamparr)
Oct 30, 2023

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Dexter Zhuang

Dexter is the founder of Money Abroad, a website and newsletter on building wealth for global professionals. Over the last 10 years, he's been a product leader, product manager, consultant and coach at companies like Dropbox, Xendit, and growth-stage startups across the US, Asia Pacific, and Latin America. His work has been featured in global publications like Business Insider, CBS, US News & World Report, and Tech in Asia. He graduated from Dartmouth College.

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