In this episode of Be Anomalous, Solai joins me for an honest conversation about unconventional careers, angel investing, identity, calculated risk, and what it means to trust your own path, even when it doesn’t make sense to everyone else.
Solai is an investor, advisor, board member, writer, speaker, teacher, and founder. She has built what she describes as a portfolio career, bringing together her experience across investing, startups, governance, and entrepreneurship.
But her path to becoming an investor was anything but conventional.
Solai began her career as an actuary, working in financial risk and analysis before spending years in the corporate world. Eventually, curiosity led her to take a different path.
She joined a startup. That experience changed the way she thought about work, growth, and what was possible.
She went from working inside a large corporation with clearly defined roles and systems to working in a company with just a handful of people—where everyone had to build, experiment, and figure things out as they went.
Her curiosity about the startup ecosystem eventually led her to angel investing.
Instead of using money she had set aside for an MBA, Solai began investing in early-stage companies, using the process to learn.
She calls it her own version of a “practical MBA.”
Over time, she developed her approach to investing, learning not only how to evaluate businesses but how to observe founders, understand execution, and recognize the difference between what someone says they will do and what they actually build.
As an Australian of South Asian heritage, Solai has also spent much of her career in rooms where she was one of the few people who looked like her.
Earlier in her career, she often felt the pressure to prove herself.
Over time, that changed.
She learned that being dismissed or underestimated often says more about the other person than it does about you, and that confidence doesn’t always come from proving yourself to the world.
Sometimes, it comes from investing in yourself and becoming more comfortable with who you already are.
But this conversation goes far beyond investing.
We talk about:
Why Solai chose to leave a structured corporate career for the uncertainty of a startup
How working as an operator shaped the way she thinks as an investor
Why she used money saved for an MBA to begin angel investing
What she calls her “practical MBA”
How to think about risk before making your first investment
Why early-stage investing isn’t about getting your money back quickly
What Solai looks for when evaluating founders
Why execution matters more than simply having a great idea
How investors can unconsciously gravitate toward founders who are similar to them
The importance of transparency and mutual respect between founders and investors
The power imbalance that can exist when founders raise capital
What founders need to understand about equity, dilution, and fundraising
Why having a rigid exit strategy too early can be a distraction
How founders can learn to delegate and let go as their companies grow
What it means to build a portfolio career
Navigating spaces where you’re one of the few people who look like you
Why investing in yourself can be the best investment you make
How confidence can become more internal over time
What Solai is learning about the next generation of founders
How AI is helping founders move faster—and where it can go wrong
Why curiosity has been the common thread throughout her unconventional career
Solai’s story is a powerful reminder that you don’t need to have your entire life mapped out before taking the next step.
Some of the most meaningful opportunities in her career came simply from following her curiosity.
🎧 Listen to the episode
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Favorite Quote
“Leap and the net will appear.”
Favorite Books
The Life-Changing Magic of Tidying Up by Marie Kondo
Quit by Annie Duke
In This Episode
(00:00) Meet Solai and her unconventional portfolio career
(01:00) Growing up between New Zealand, Australia, and South Asian identity
(03:30) Why Solai became an actuary
(05:30) From corporate life to the startup world
(09:00) What working as a startup operator teaches you about growth
(12:30) How curiosity led Solai into angel investing
(15:30) Creating a “practical MBA” through investing
(18:30) What first-time angel investors need to understand about risk
(22:00) How Solai evaluates founders and what she looks for
(25:00) Being an outsider in rooms where you don’t look like everyone else
(29:00) Why confidence has to become an internal process
(33:00) Power dynamics between founders and investors
(36:00) Equity, dilution, and the realities of raising capital
(40:00) Why founders need to think long-term
(43:00) Learning when to delegate and let go as a founder
(46:00) Building Chai and Capital and exploring the India–Australia tech ecosystem
(50:00) What Solai is learning from the next generation
(53:00) AI, agents, and the danger of AI slop
(56:00) The unconventional career moves that shaped Solai’s journey
(58:00) Solai’s favorite quote and the lessons behind knowing when to leap
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