I didn’t start wondering about how to pay the bills when I started bootstrapping a startup. I started having it in childhood, while observing my parents struggle with paying the bills.
They were not poor or uneducated, but we lived in a country where criminal-level inflation and lack of production had turned a wealthy nation into a kleptocracy of corrupt morals. I couldn’t even deal with the sandwich vendor at my school when I was seven without having my money stolen.
So I spent the first three decades of my life chasing money. I started from the bottom and ended up working at the best companies in the tech world, at the highest tiers of salary that I could imagine. But something wasn’t right. Looking at my peers signing 30 year mortgages, I couldn’t come to terms with chaining myself to the desk and throwing the next three decades away to be able to pay the bills. I felt like instead of money, someone was now out to steal my time away.
So I jumped off the cliff and spent all my savings on a startup. It was going to work, I knew it. And that exact egotistical attitude caused us to make some bold but bad decisions. My cofounder who had come up with the idea arrived from his house across the bay one day to tell me he could no longer face the bills coming in. He was a father and the sacrifices were affecting his children. He walked away. I saw no remedy. The startup failed.
Without money and back at step zero, it felt like I had been asked to hold my breath for 120 seconds to get out of a life sentence, only to discover that I had to hold it for another ten minutes. My face was going blue. The silent failure devastated me. It knocked the lights out and put me in a dark place. I started writing to let the frustrations out and organize my escape plan. The first pages of my book, (which turned out to be chapters 5 and 6), ended up being written then.
I started meeting a few potential cofounders for the second startup. The startups would churn so fast due to the terror they’d feel once they noticed their own financial free-falls that I went through one cofounder and startup concept a week. Out of pity, my wife asked me to focus on writing instead of engineering for a while. I asked, “But what do we do with the bills?” She said, “I make enough for the minimum essentials. We’ll figure out the rest.” We used some of our emergency funds to get out of Silicon Valley for a while and smell the roses. It’s important to realize in retrospect that the love from one’s family is the first “angel” investment one receives.
I hit a lucrative contract during the time I was spinning my wheels writing. The contract paid more than a full time job. But it was short term: long enough to breathe for four months. Before the term was over, they asked me to become a full-time employee. I insisted on keeping things the same, but they wanted to own my time. So I said goodbye. Shortly afterwards, due to having the freedom to look, I met the cofounder with whom I started the second startup. We were going to pay the bills for schools–corporate sponsored school fundraising.
It’s important to call out that pivot. Your first startup fails because you’re solving for an egotistical need (paying your bills). The surviving startup pivots toward sympathy (paying bills for others).
San Francisco rents started rising at the pace of 10% a year while my wife worked outside the city (lower pay grades) and I was still building from scratch without funding or pay. We moved in with friends. But shortly after, their incomes improved, so we developed a conflict of interest. My wife and I projected our cashflow to be exactly zero with a much lower rent outside the city. We geared up to move. During these times (in the third year of zero income for me) I’d speak every week on the phone with my father about the startup. I’d always insist on the difference we were making, and he’d always press on how I was going to pay the bills. I cried alone many times before the move, because as a child, I had to move often; I had somehow brought about the same circumstances for my future children.
One week before the movers arrived, we had packed up everything. All I had was an exercise ball, in an empty office room of our three-bedroom, mostly vacated shared apartment. It faced the Sequoia retirement community on Geary street in San Francisco from its Eichler-architected floor to ceiling windows. The retirement community stared me in the face every time I thought about my poor father being trapped with rising bills in retirement age. That same fate was coming for me.
I was looking at my reflection in the window, sitting on my meditation ball, staring back at me like my dad when he had to move us. Then I started rolling with the ball and was thrown straight into the window. It shattered like 17 daggers, with the quality of 1960s untempered glass. All I could think while I was rolling into what could be my guillotine execution was damn it, that’s going to cost a few thousand dollars I don’t even have.
A few hours went by. The spider crack in the glass window has taken away my reflection. It was as if I had gone through a mirror of mid-life transformation. I called a glass company to quote me a price. $600? I wrote a check. That was that.
I texted my wife to say I had broken the glass before it got fixed. I expected her to say, “Well, time to look for a job.” But instead she asked, “Are you okay? Do I need to come home?”
I spent the remaining days until the move writing the first half of my book. Why? I’m not quite sure. I believe I’m writing a letter to the past, to let [my former self] know it’s okay. Not having money is okay. Moving to a cheaper place is okay. It’s all going to turn out okay.
My wife didn’t expect me to go back to a job, but the jobs started coming to me. Their offers were extravagantly high, because I experienced this transformation that was basically I already died going into the window glass. This is someone else. He doesn’t need your money. In one such instance, a job offer turned into a negotiation with the higher management team at a billion-dollar market cap company. Every “no” I threw out there would increase the job offer by another $25K. They went up four times. But all I could think was if you monopolize my time, how will those schools who are my target customers pay their bills? I turned down the highest paying job offers of my life to get paid nothing.
One time I ran into a friend who asked, “How long have you been doing this startup?” I said two and a half years. “Oh, not for that long then,” he said. I wanted to kill him. People don’t understand the concept of time in a startup. If you can hold your breath for two minutes, talk to me then.
But interestingly, a founder also doesn’t understand that same time scale. The friend was right. It really hadn’t been that long. Time frames during which I’d go insane and exclaim, “We’re not ever going to find funding!” were only 20 days long. For a founder, that’s eternity, because the landlord will be knocking again. For an employee, that’s a few coffee breaks. And it was in that spirit that I had a revelation when I finally wrote the check for the broken window that essentially put me in red ink:
If this startup kills me, I’ll still do it, because others are suffering more without it.
Every angel investor that we had talked to and gotten nowhere with suddenly started following up with us. Why? I suspect they didn’t think we’d live this long, or perhaps all their other prospects actually died. It started with one angel, who referred me to another, who referred me to a friend, who referred me to another founder who had recently sold his company, who referred us to his mentor, who ended up committing to give us 10% of the funds we were planning to raise. That chain would not have worked if we were still on the timescale of desperation. When we decided even if this kills us we’ll make it work, the perception of time went away. And we might finally be at step 1.
I’m meeting this 6th-degree angel next week, but I don’t expect his check. I expect for the meeting to be short, because one way or another, I’m heading back to my laptop to work on the product.
Sympathy for the humanity you’re working for: that’s the currency of a founder. The prison of ego is a life sentence. The only way out is to hold your breath long enough.
This was a brief summary of the first half of my upcoming book about early stage startups, “The Currency of a Founder”. You can keep up with the coming chapters at my book page: The Currency of a Founder (book), by Amin Ariana.
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