Confessions of a startup founder's wife

One morning this past spring, I was working at my desk when Biz, a fellow tech reporter with a bloodhound's nose for news, texted me a screenshot of my husband's Twitter bio.

Something was missing. Kyle had deleted the name of his startup.

"What happened to Playbyte????" Biz wrote.

Confused, I wrote back, "Wait that's so weird. I'll talk to him."

Kyle and I both work from home, and I wanted to confront him then and there. But talking about my husband's battle-scarred startup always had the potential to turn into a fight. And if his reason for scrubbing Playbyte's name was that he was winding it down, well, that would be an even longer conversation. 

That night, as he plugged in his Apple Watch, iPhone, and Steam Deck on his side of the bed, I sidled up to him and asked what the story was. 

Kyle shrugged it off. Playbyte, which had started as a kind of TikTok for games (which I loved) and then pivoted to software for indie game developers (meh, he could do better), was about to pivot again. For weeks, Kyle told me, he and Playbyte's two employees — all who were left after he laid off several others during the tech downturn — had been working on a new tool, one that would let anyone build a web app by describing it to a chatbot. I knew that part, though barely because Kyle had been sharing less and less about the company with me. 

Then he said he didn't relate to the name Playbyte anymore.

My cheeks flushed. I wanted to scream. Kyle had put 3 ½ years of his life — of our life — into building his startup, and now he had wiped it from public view in a few keystrokes. That, I told him, sent a message to his 20,000 Twitter followers that he had given up. What he was really doing was siphoning off code from the old project to start a new one. Had he considered the knock-on effects on his ability to attract new investors or talent? (After eight years of reporting on startups and venture capital, I'm sad to say, I reflexively use phrases like "knock-on effects" with my husband in bed.)

Kyle knit his brow and explained why he didn't need more money or engineers. I changed the subject to what we should put on before bed. We watched "The Mandalorian" in stewing silence.

By the time I rolled over and turned off the light, I was feeling a pang of remorse. I wished I had told Kyle that I would understand if he wanted to quit. I'd reassure him that he hadn't failed. I had the words ready, but I couldn't bring myself to say them. I still wanted to present as the kind of wife who had unlimited confidence in her husband's ability to turn things around.

In my reporting on the world of company building, I've grown familiar with the myriad ways startups end — with acquisition jackpots or bankruptcies, with trading debuts or lawsuits, with Champagne or jail. "The myth of a successful journey is that it starts with an idea, followed by a ton of hardship, and then a gradual and linear rise to the finish line," the founder and investor Scott Belsky writes in his book "The Messy Middle." It's taken living with a founder to fully dispel that myth for me. "In reality, the middle is extraordinarily volatile — a continuous sequence of ups and downs, flush with uncertainty and struggle," Belsky adds. That's as apt a description of Kyle's startup as it is of our relationship. And in our case, the startup's middle has surely been made messier by the fact that the startup's founder is married to a startup reporter.

Lately, I've been fixated on a nagging question: Would my marriage be happier if my husband's startup failed?

Four years ago, when Kyle began talking over dinners and dog walks about becoming a founder, I secretly hoped he'd change his mind. I'd written hundreds of stories about the life he was signing up for: 80-hour work weeks, high stress, low salaries. Not the ideal lifestyle to adopt, right as we were planning to start a family. I told Biz and Jillian, also a tech reporter, over breakfast in San Francisco's Mission District that I thought this was a bad idea. They asked whether we had savings to fall back on.

Nine in 10 startups fail. Yet, at the time, it didn't occur to me that my husband's might. During the 10 years I'd known Kyle, things always had a way of working out for him. When he was 20, he dropped out of the University of California, Berkeley, to write for TechCrunch. Before long, he had parlayed a sit-down interview with the renowned investor Chris Dixon into a dealmaking role at Andreessen Horowitz. In 2019, while working at a drone startup, he caught the entrepreneurial bug.

My worst fear about his startup wasn't that he'd fail. My worst fear was that I'd never see him, and we'd grow apart as he became a staggering success. Late nights of toiling over code would lead to private jets and alcohol-fueled company retreats, and I'd be left behind, reading about his corporate conquests under someone else's byline. Earlier that year, Jeff Bezos and MacKenzie Scott had filed for divorce amid a tabloid scandal that included love nests and racy texts with a news anchor. I wondered whether someday our children would spend every other weekend at Kyle's Pacific Heights mansion with his own "alive girl."

But I didn't tell him any of this. Like my mother, and her mother before her, I am ruthlessly nonconfrontational. When I was growing up, my dad lovingly referred to our "Schulze talk" — the thing you say when you're upset, instead of what you really mean. Becoming a reporter and learning to ask hard questions of founders and investors helped immensely, but being hard on the aspiring founder I slept next to was another thing. I worried that if I didn't support his career, my husband might love me less.

As Kyle was conceiving his startup, I found out I was pregnant. For that, I did confront him. I told him I'd feel more comfortable with him becoming a solopreneur if we moved from San Francisco, where rents were catastrophically high at the time, to New York, where we would be closer to family when the baby arrived. He agreed to my condition, even though it meant he'd be a continent away from the investors and talent he needed to court.

Kyle, who learned to program in fifth grade so he could mod his favorite video games, dreamed up an app for creating and sharing simple games in a scrolling feed. I thought it was fantastic, and well-timed: TikTok was just then taking off in America. Together, we picked out a name by covering our living room walls with sticky notes filled with words and phrases. He settled on Playbyte, a nod to both the app's bite-size games and our tug-of-war-loving pit bull, Nubs.

I put the Post-its in a shoebox of keepsakes, along with handwritten love notes and ticket stubs from our travels, at the back of our closet. Back then, I imagined I would get the Playbyte Post-it framed and give it to Kyle on the day he took the company public, generating a windfall for our family that would pay for our daughter's tuition and so much more.

Lately, though, the Post-its feel like just another relic of our relationship, ones we'll dig out decades from now and laugh over. "Remember when you tried doing a startup?" I'll say.

The most shocking thing I've learned about startups is how boring they are. Day to day, almost nothing happens. There's a call with an investor, a coding sprint, and a team stand-up. So much for "move fast and break things." In my house, it was more "futz endlessly with a Figma file and chat with employees on Discord all day."

Being a startup reporter married to a startup founder isn't without its perks. We can talk about our days without having to explain a million little things. When I get tripped up on jargon such as "transformer" or "smart contracts" or anything Marc Andreessen blogs, Kyle is my Google Translate for tech speak. He rolls deep in juicy news tips, which I'm frustratingly unable to use. And he sets his own hours. When I have to work late, he can easily cover parenting duties.

At times, though, it was strange to experience the way my professional and personal lives had blurred. One drizzly morning last spring, as the tech sector entered year two of a global correction marked by mass layoffs and a dearth of venture-capital funding, I was reporting a story about a looming "mass extinction event" for startups. In our living room, my husband had gathered the team for an off-site. By then, they had already killed the first two iterations of the startup and had begun work on the chatbot app builder. They spoke hunched over laptops on the couch, surrounded by paper coffee cups and twisting charger cables.

"This isn't going to be the thing that determines if we become a billion-dollar company or go out of business," I overheard an engineer say matter-of-factly.

The next night, when Kyle and I were out to dinner with the team, I admitted how bizarre it had been for me to eavesdrop on the challenges they faced at the same time I was interviewing people in the tech industry about the Darwinian moment that startups were facing. To my surprise, Kyle had a confession of his own. He'd been listening in on my interviews, and overhearing talk of things such as "startup mortality rates" didn't exactly give him hope. 

I'm not sure Kyle has found as many perks to being a startup founder married to a startup reporter. Perhaps more than any other job, entrepreneurs are encouraged to fake it till they make it, to either bountiful or cataclysmic results. "Startups only exist because their founders are willing to suspend the disbelief of the probable and instead consider what is possible," Eric Paley, an early Uber investor, once wrote. Steve Jobs' infamous "reality-distortion field" let him convince himself and nearly everyone around him of practically anything. Kyle's reality-distortion field seemed strong, and it's often been at war with my journalistic service weapon, a bullshit radar gun.

I knew too much about what could go wrong, like a first lady who doubled as a reporter in the White House press corps. I often assumed the worst because I'd reported dozens of stories about the worst. When one of his favorite employees quit to start his own company — just two months before Playbyte debuted in the App Store — it put both of us in a tailspin of doubt. Had the employee left, we wondered, because he lost confidence in Kyle's idea?

As Playbyte struggled to gain users and investors, I worried less about being the relentlessly positive cheerleader. I began plying Kyle with unsolicited reviews of his pitch deck and interrogating his every move. Did the team really need those logo fleece blankets? When the company had layoffs in spring 2022, had he done everything possible to minimize the impact on his employees? I thought I knew better than he did — after all, I'd just spoken to a dozen talent partners at venture-capital firms for an article, "11 ways companies can ease the burden on laid-off employees." That night, we sat on the bed, bickering over how long the company should extend healthcare benefits. I wanted him to stretch coverage longer. He wanted to be comforted.

Kyle began to bristle at my feedback. Knotted with anxiety, he started withholding details and sought my input less and less. He was trying to find the idea that clicked and found no joy in discussing those that blew up on the launchpad.

Like other founders I've met, Kyle's mood is moored to the health of the business. When he's excited about a development, he oozes confidence and throws himself into the company, often working past dinner. I rarely mind caring for our toddler solo on those nights. Better a happy partner, I figure, than a cranky coparent. Because when a bug creeps into the software, or an investor ignores his email, Kyle can be hard to be around. He snaps at coffee spills and bad drivers and grunts loud enough at his computer to jolt our dog awake. I know things are tense when I hear the dumbbells clanging from his office in the middle of the day. He feels the upsets so intensely because he believes every one reflects on his acumen.

Over the years, I've come to believe that Kyle would cut off his own arm, "127 Hours" style, before putting an end to his startup. After the layoffs, when I asked if he had considered winding down the company and returning some of the funding to his investors, he immediately launched into a pitch on how well the beta test was going. I'm convinced he's going to keep building until he's spent the startup's last dollar.

I often write about founders having blow-through-walls resilience. The Clubhouse founders Rohan Seth and Paul Davison had at least nine failed apps between them before hatching the breakout app of the pandemic. Steve Huffman led the turnaround of Reddit after a firestorm of user revolts and hate speech. I wrote about them in nearly glowing terms. But the same determination I so admired in them I found unnerving in Kyle. I was exhausted, my patience eroding with each new round of hiring and firing, capital raising, and pivoting.

I told my therapist, my friends, and my boss, whose husband had started and sold his own startup, how I wished my husband would get a "normal job." They encouraged me to tell him how I felt. But that would require me to confront my fear of confrontation. 

More than once, I tried to "Inception" Kyle by talking up other companies I thought he'd enjoy working for. He could join a venture firm in Boston, say, and make a six-figure salary, plus a share of the fund's profits. I knew that shutting down his startup would deal a disastrous blow to his confidence. But it would be temporary. In a new role, he could resume a healthy relationship with work. The weight of failure would fall across the entire organization, not on his shoulders alone. He could feel good about himself again.

I could breathe easier, too. The money would certainly help. But more than wealth, I want things to be less fraught at home. I want to talk about Kyle's work, and mine, without tiptoeing around a minefield. I want him to be free of the torment the startup puts him through. I want to release myself of the guilt I feel for tearing us away from the Bay Area, where he would have had an easier time getting funded. I want peace of mind.

One afternoon in September, I watched Kyle leave his office and face-plant onto the bed. I went over and placed a hand on his back. He looked up at me, tears forming. 

"Do you want to talk about it?" I asked.

He told me that in a few hours he had to call an investor and share the news: The app-building chatbot was over.

I tried to assure Kyle that his investor had calls like that all the time, especially this year, as founders twisted themselves into pretzels trying to get funded. Just because everything hasn't clicked into place yet, I told him, doesn't mean it won't eventually. After all, YouTube launched as a dating service, and Instagram started off as Burbn.

For once, I thought, I had found the right thing to say — but I must not have been very convincing. Kyle sank back into the pillow and sighed, and I went back to work.

Now Kyle's startup has pivoted a third time. Instead of creating software to help amateurs and indie developers make video games, he and his team plan to use what they've learned to create their own game. The idea is a first-person shooter and an homage to a game, set in a ruinous Russian war zone, that became a pandemic smash hit.

I'm skeptical. In my years of reporting on startups, I've never heard of a pivot like that. Game studios don't exactly scream venture-backed business. Many are bootstrapped or funded by an incumbent studio searching for the next big hit. In the past few years, venture investment in gaming has swelled, but it's still a precarious time for startups that need to raise capital.

The truth is, I don't know if Kyle's startup will make it.

But in the throes of the pivot, Kyle and I faced our most harrowing experience yet. On Labor Day, we were role-playing characters from "Legend of Zelda" with our 3-year-old when Nubs bounded into the kitchen. He jumped on me and kissed me hard before padding over to Kyle. That's when our daughter came up behind Nubs, startling him, and he bit her on the face, slicing her eyebrow and cheek.

She turned out to be OK. But that night in bed, after she had fallen asleep, Kyle and I wept, cradling Nubs in our arms as we had every night for six years. We agreed to call the vet in the morning to discuss euthanasia. Nubs, Playbyte's namesake, was Kyle's best friend. If we went through with it, I asked, did he think he could handle being with me at the vet to put Nubs down?

I wasn't sure how he would respond. This was a man for whom things had always fallen easily, happily into place. But in that moment, as he faced the death of a loved one, I saw that something had changed within him. He now understood peril, having chosen a path rife with it. He had told employees he cared for that he was letting them go. He had gone to investors, tail between his legs, to confess that a new round of funding had fallen through. He had weathered incessant grillings from his reporter-wife, who was not always as supportive as she wished to be and whose own anxiety had often contributed to his. The loneliness and the self-doubt, the sleepless nights and the cold sweats, all the stress and the sorrow of launching and tending to a startup, had shown him something.

"I can do hard things," he told me. He would go with me to say goodbye. 

For a flickering moment, between sobs, I was bursting with pride.

Melia Russell is a senior correspondent at Insider.