From Startup Product Leader to Part-Time Portfolio Career
Creating time and space to travel and work on new endeavors
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Dexter is representative of a new wave of professionals who are building portfolio careers. He has an Ivy pedigree and worked at some top companies like Dropbox, but has now decided to take a different path. Part-time work has given him the freedom to travel and explore new ideas and projects that are often too tiring to do after a typical 9-5+.
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For 9+ years, he has been building and growing internet products across Silicon Valley and Southeast Asia. Along the way, he worked with top companies like Dropbox and Xendit, led a 70-person product org, and helped build two $50M+ ARR businesses. He ran a tech career coaching service for 3 years and mentored startups for 500 Startups, Iterative VC, and First Round Capital.
He is also the creator of Money Abroad, which publishes content on how to build wealth living abroad for 20,000+ overseas professionals across Asia Pacific & the Americas.
What’s your experience with part-time work?
In 2019, I left my tech job in San Francisco to travel the world for a year.
Up until that point, I had worked in several growth and product management roles for fast-growing companies over 6 years. While on-the-job, I learned that I enjoyed mentoring and coaching my teammates. I even received positive feedback from my mentees when I wore that hat. During that time, I had an insightful career coach who helped me navigate tricky aspects of career transitions.
On my sabbatical, I wanted to try part-time work. I naturally gravitated towards the idea of experimenting with career coaching. I wanted to test applying the frameworks and exercises I created in my job to coaching client sessions. I started out coaching on a platform called Hire Club. Later, I spun up my own private practice to gain more control over the experience.
Fortunately, I felt proud to demonstrate results for clients.
In the first 5 months, I coached 30+ clients including many that landed their FAANG or tech startup dream job, won my clients ~$100k in salary raises, garnered 27+ 5-star reviews, and got featured in various outlets like Business Insider and CBS.
I enjoyed this work, but I paused 80% of my service after starting my new product leadership role at Xendit in Singapore. Given its intensity, I wanted to focus the bulk time and energy on being present for my team.
Fast forward to 2023, I had left Xendit to experiment with new projects.
For example, Money Abroad (https://www.moneyabroad.co), a weekly newsletter on how to build wealth living abroad for overseas professionals. After living abroad for a half-decade, I grew tired of how complex personal finance gets for expats like myself and yet how few money resources are available to people with <$10M net worth (minimum for wealth managers). So I started writing online about this topic.
While I work on my own projects, I wanted to try a new part-time role: advising companies. I advise founders & executives typically on a critical pain point related to product management, growth, or scaling their organization.
I’m still testing out engagement models, but currently the structure is lightweight. I meet with the leaders on a bi-monthly or monthly basis to help them get unblocked and gain clarity on how to move forward. So that they can accelerate their progress towards product & business goals.
Most of my lead flow has been inbound through my website/LinkedIn and founders in my network after verbally sharing I was open to advising engagements.
Why is working part-time important to you?
Part-time work is ideal because it allows me to leverage my industry experience & skills to help companies without needing to work 40-60 hours/week. And earn income while doing so.
This setup allows me to carve out more time to work on my projects. While I tried to make progress on my projects during a full-time role, the reality was that product leadership is all-consuming. 90% of the days, I had no energy left at the end of the day to be creative and execute towards the next milestone.
I take the roles that I work on very seriously, but I make sure to not let work control my life. Working in a part-time fashion helps me do this.
Part-time work also allows for nomadic travel. When I was a part-time career coach, my flexible schedule made it easier to create designated time to explore the city.
What does your compensation look like?
When I ran my 5-figure career coaching service, I saw coaches charge rates ranging from $100/hour all the way up to $1000+/hour. Most new coaches start off on marketplaces and platforms, but these typically take a cut as commission (10-30% take rate). Hence, it makes sense to eventually setup your own private practice once you build up your reputation and can attract demand.
For my advising service, I am still very much exploring the right compensation model. Currently, I am primarily offering a monthly subscription for my clients. Each month, I offer a certain number of 60-minute sessions and in-between text/email support.
What are the tradeoffs to working part-time vs one traditional full-time job for you?
While part-time work has the benefit of flexibility, I feel that traditional full-time work has more opportunities to build deeper relationships with more people across the company. One of the best parts of work is getting to know amazing people. It’s a bit harder to do this with advising engagements, where you work with mainly the founders and leaders. You can feel a bit more disconnected from people on-the-ground and in other departments.
What advice do you have for someone who wants to work part-time like you?
I would suggest reflecting on your goals — and getting crystal clear. Part-time work is great for certain things (flexibility), but it’s not for others (work relationships). Given there are real trade-offs, be honest with yourself on what you want to get out of your career journey. Then work backwards from your goals and see if part-time work is a fit.
Any tools or services you'd recommend for people who want to go part-time?
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