when @zangimmortal and I met, i felt similar to this moment. after years of building my company, we faced a downturn— and had to part ways with some people, including a few who took it personally and flamed me for months on end. I retreated. I didn’t want to do events or show my face anywhere. My health went to shit and stayed there; i was a nervous wreck, whereas before i was a confident (but naiive) twentysomething. I just wanted to hide away, leave the industry, maybe go back to my hometown in Ohio where no one cared about tech but where at least the avg person was a fundamentally decent human. @mint0themax stepped up and offered to take what had been my role up until that point, that of the “external founder” — BD, events, partnerships, the works. And she got better at it, eventually way better than me. I focused instead on improving our product itself. I pared down the team further, then rebuilt. I tweaked our pricing. Got our FinOps in order with the incredible @NateElliott. Made our portfolio & sales content better. I treated everything we did at Airfoil like a design problem in and of itself, from the cadence of meetings and design reviews to the project management templates we use. I was making progress fast. I began to regain my self-worth. But wounds from the past didn’t heal. Every BD event, every trip to win over customers, I would still be triggered by things from the past. and with Min getting us great partnerships outside, I found every excuse I could to just stay put, stay comfortable, stay inside. My life had some stability again, but truthfully the old phil was not really back. @zangimmortal and I were about 1.5 yrs into being together at that point and we began searching for stability in Singapore. and we began to find it— an apartment in the East in a neighborhood we loved, a cadence of weekend hangouts with crypto friends, hosting teatimes and gatherings. but that stability was a mirage. we didn’t realize it, but we were confusing stability with routine. we were floating in the water, letting the current pull us, believing we were swimming. not going anywhere. coming back to SF, that realization hit me in the face and I couldn’t ignore it. I’d genuinely accomplished a lot in the past few years — built and retained team of 30+, kept us above $5M ARR for multiple years, learned how to sell to companies in Singapore, South Korea, Malaysia, and Vietnam (way different than working with US companies)… valuable things, but I’d switched from a period of personal growth to a period of maintenance without realizing it, similar to Zang’s story below. I was never a backpacker, I’ve never been to Laos, but I still uprooted myself, moved 5,000 miles from my home country to a place I knew nothing about, and built a business there. I said yes when my friend back in 2015 offered me her couch in SF to crash on if I wanted to try my luck building my startup in the bay. I said yes when another startup offered me to join their founding team when it was clear my first startup wasn’t working, and join @spc as a result. I said yes when my cofounder wanted me to move to Toronto to build our first design office in Canada, and I said yes when we needed to build our engineering office in Singapore. I got to Singapore, felt more rooted there, and gradually stopped saying yes. Building a new business is a risk-taking endeavor. To do it, you have to be ready for that risk. Most businesses fail, most outcomes are worse than just working for a great employer. This shit is glamorized but 80-100 hour weeks for years on end is brutal and pushes you to your absolute limit, in exchange for paying yourself whatever’s left after your teammates eat first. So if you’re taking that risk, you have to go all in. Otherwise it’s not worth it. You have to keep learning. You have to avoid stagnation at all costs. You have to keep saying yes. Let the journey take you where it will. That’s what you signed up for.

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