That Time I Lost Everything and Started Over
How sleeping on five different floors after my startup failed taught me resilience, the value of friendship, and what true stability means.
In late 2014, I slept on my friend's floor in San Francisco's Bayview neighborhood, broke and directionless. Just twelve months earlier, I'd been an investment banker. Now my startup had failed, my savings were gone, and I couldn't afford rent. The previous seven years, while in the USA, I'd maintained financial discipline—never wealthy but never in debt. As I lay there, I couldn't shake the memory of my mother crying when I told her about the startup failure.
Until then, I managed money well. I paid off my $11,000 UC Berkeley debt within six months of starting at investment banking, never carrying significant debt afterward—typical immigrant resourcefulness. I'd worked nine jobs prior to this, put myself through school, and was plotting my career path when two realizations hit: the entrepreneurship bug bit me, and investment banking wasn't my calling.
I quit my prestigious job at Qatalyst to build Nibbol, an online booking platform for veterinarians. I brought in three co-founders—one from my CCSF days where we'd started a group together, plus two engineering friends. We had ambitious plans beyond just bookings, but too many decision-makers doomed us. The startup collapsed, taking all my savings with it.
When I told my mother about the failure, she burst into tears. Strangely, I felt calm. I recognized this as my lowest point since my early immigration days, but understood life's natural cycles of success and failure—a philosophy I later tattooed in Kanji on my arm. Our startup lifestyle had matched our finances: four of us sleeping on mattresses in a single room in SF's Outer Sunset.
After my startup failed, I crashed on my Berkeley friend Ryan's couch. We'd been friends since our UC Berkeley days. I wasn't homeless long—another founder I barely knew offered me his Palo Alto floor and a job when I desperately needed income. Five weeks in, I quit when I realized the role required bullying immigrant workers.
I moved to a floor in Los Altos, hosted by a new friend from that brief job. Two weeks later, I relocated to a friend's place in SF's Bayview while hunting for proper employment. I debated between sales and product management careers, but chronic imposter syndrome and a good offer from MuleSoft pushed me toward sales.
During those Bayview weeks, I met a mutual friend who became my girlfriend and offered me free housing. In total, I slept in five different places during this period—one in Berkeley, one in Palo Alto, one in Los Altos, and two in San Francisco.
MuleSoft transformed me. In just one year there, I rebuilt my savings and regained my confidence. I formed friendships that remain my strongest to this day. I left shortly before MuleSoft went public and was acquired by Salesforce. My next move was to MemSQL (now SingleStore), which became the stepping stone that led me to NEAR, where I worked before becoming an angel. I've written about my current role elsewhere on this blog.
My couch surfing experience taught me four critical lessons.
First, don't build startups on personal savings alone. Watching your bank account approach zero adds crushing stress to an already difficult journey. I'm not claiming losing investors' money is morally better—managing others' capital carries its own burden—but external funding would have kept me off friends' floors.
Second, friendships matter enormously. Some friends who helped me had been in my life for years; others stepped up during this mini crisis. Their support proved invaluable.
Third, perspective is essential. Life has natural ups and downs. Many circumstances lie beyond our control, and sometimes you need to "abide," as The Big Lebowski would say.
Finally, develop a sense of control amid chaos. Knowing I could find a job gave me confidence even while living on a floor. True stability doesn't exist—though many chase it. What matters is your ability to influence some aspects of your life during its most chaotic moments. This creates the foundation from which you can climb out of even the deepest holes.
Looking back at this period 10 years later, I'm grateful for this experience. Not just because it taught me valuable lessons, but because it shaped how I approach challenges today. When I started at NEAR, or during various tough moments in crypto winters, these lessons proved invaluable. The knowledge that I could pick myself up even from sleeping on floors gave me a kind of confidence that's hard to get any other way.
The funny thing is, most "stable" things in life - jobs, relationships, markets - aren't really stable at all. True stability comes from within: knowing that whatever happens, you can figure it out. You can rebuild. You can find your way back up. Even if that means crashing on a friend's floor for a while.
To those going through similar tough times: remember that this too shall pass. Build your support network before you need it, keep your perspective when things get rough, and most importantly - trust in your ability to regain some degree of control, even when everything feels chaotic. That's the real safety net.