Take asymmetric bets — my favorite career advice ✨
What's a decision where, no matter the outcome, you will always come out a winner?
My mentor who's scaling his healthcare startup looped in one of the heirs of the largest pharmacy in the Philippines so that, even if the startup "failed", he would've shared the learnings with someone influential enough to run with it at scale.
No matter the outcome, he would have created a dent in the Philippine healthcare landscape. (Btw, his company is 250+ people, +$XM strong. Far from failure.)
Trick is: You control the creation & decision of asymmetric bets. The upsides can be in the form of social impact, immense learning, a strong network, or plainly having a fun time. Whatever measure of success is right for you.
When odds are against you, construing asymmetric bets hedges your chances against those odds (and helps with your sanity!)
My bet 🚀
This past week I took a BIG leap towards my asymmetric bet.
Some personal news:
I quit my job. 💼
I’m starting a company. 👩💻
I joined a fellowship (that’s giving us $400k + structure to pick ideas, validate and raise a round.) 🤯
I quit my job
On 2/19, I officially lost my @linkedin.com email. #nostalgic
Just before LinkedIn, I went from near deportation to getting an awesome job through messaging a certain hiring manager who said she was “hiring” on her profile.
That hiring manager fortunately brought me on her team. Throughout my time, I felt empowered to fulfill such strong missions as part of 1) the Online Jobs team, growing the number of hirers finding quality candidates; 2) Women [in] Product, improving the number of women hires at LinkedIn and; 3) the Filip[in]os community!
My LinkedIn journey happily culminates with the successful launch of Open to #Hiring, enabling more job seekers to find amazing jobs the same way I did. Funny how things come full circle! I’m excited for its future growth and trust that, with or without me, the team will bring it to even further heights.
I wouldn’t be a tenth of the leader I am today without the people and immense growth at LinkedIn. It will always have a special place in my heart. 💙
I’m starting a company
When I told folks about my next play, many said “I’m not surprised, that’s so you!” Thanks for the validation, friends!
Truth be told - I’d been contemplating this decision for a couple months now. What pushed me off the edge? The stars aligned:
⭐ Problem space. I’m compelled around a problem space I want to explore & go deeper in (passion economy). Caveat: pivots are abound in startup land so while we explore this space, who knows where we end up, but excited for the journey either way.
⭐ Personal. I accumulated enough personal runway to allow me to jump in!
⭐ Reframed risk. I reached a point where it felt more like a risk not taking this “risk” than it was waiting.
⭐ Growth. I’m hungry to quicken my cycles of learning. What better way to learn?
As for the company itself, I’ll share more down the line. What I will tell you is we’re getting a little help from some friends…
I joined a founder fellowship
I’m a Fellowship Power User. I was part of Kleiner Perkins Product Fellowship (how I know my co-founder!), On Deck Founders (soon: OD Performative Speaking), Dorm Room Fund Female Founder Track, Horizons School of Tech, KayaCo, Violet Society. Huge community person (not even mentioning the bunch of communities I’ve created & led!)
Most recently, Amy and I got accepted to the South Park Commons Founder Fellowship! I’m grateful for the SPC team for taking a bet on us.
SPC announced the South Park Commons Founder Fellowship program in December 2020. Fellows receive $400K upfront in exchange for 7% of their company (3.2x the YCombinator deal, for the same equity stake). Teams will take 6–18 months to pick ideas, validate them and raise an institutional seed round. We’re the inaugural class of 16 fellows, across 10 companies!
The story behind this was a pleasant surprise.
I was perusing Twitter one day and saw the announcement.
I shared it with my co-founder and said “Meh, looks cool, but we should focus on building. Applying to programs can wait.”
A couple days later, one of the friends we were living with in Salt Lake mentioned he was applying to a fellowship program (the same one) and nudged us to apply.
So we applied. We got rejected the first time. Then got news that there was more room and, voila, a pleasantly surprising acceptance!
Regardless of this fellowship, Amy and I would have still built our startup together. But, wow, how grateful I am that we have the support of this awesome group.
Wait, where’s the asymmetry?
A couple things that make the move asymmetric in my 👁️:
The learning. One of my reasons for jumping into this journey was to quicken my cycles of learning. The startup nature vs. large corp immediately enables that. I’m also trying to be intentional about what I want to learn. Top of mind: picking markets, fundraising, sales, hiring, managing teams. I’m adept at the R&D/product-building aspects of running a company so want to be intentional about areas I haven’t yet dabbled in. I started a “Nuggets of Lessons” doc to compound my learnings in all areas. I’m up to 30+ entries already and it’s only been 2 days! On top of that, I’ll continue #LearningInPublic through this newsletter. Thanks for keeping me accountable!
People serendipity. Just from launching my side project PassionEconomy.xyz, I’ve already befriended many spectacular others, incl. writers of this gaming newsletter, awesome operators at Reddit & Teachable, founders of cool startups and Li Jin herself! Imagine who else I can attract to my orbit through working hard on a startup in the space.
Impact on an exciting problem space. The problem space I’m most excited about is the passion economy & broadly future of work. Looking to ride the wave of growth & contribute to the broader movement. Over time, similar to my mentor, I’ll think more about how I can manufacture even stronger asymmetry.
Impact on lives of future founders. My true north is impacting emerging markets in Southeast Asia (like my home, the Philippines) through tech. I’ve accumulated learning capital as an operator in a startup & in a large company. Now’s my chance to do it as a founder &, in the future, pour those learnings back to founders in communities I care about.
I’m HYPED but that hype is mixed with some anxiety, of course. It’s a big step. But luckily my natural and manufactured asymmetries keep me sane.
Thanks for joining me on the journey, friend!
Nudges of the week 👀
A good one: Erik Torenberg’s take on Asymmetric Bets
Making the leap,