My Startup Failed Six Years Ago. I’ve Been Hiding from My Shame Ever Since.
Millions of people listened to my Y Combinator-backed startup’s story. This is what happened after everything fell apart.
Two summers ago, I attended a friend’s birthday party, a small gathering of around a dozen people on a roof in Crown Heights. I found myself talking to an assistant producer of a big podcast, who was a few years younger than me. She was friendly and interesting and I was doing my best to friend-court her.
And then she asked the question I dreaded most.
“What do you do?”
I swallowed and did my best to maintain a cool, calm expression. “I tutor. And write.”
“Oh,” she said. She turned and waved to a guy across the roof. “Excuse me — I have to go say hi to my friend.”
She walked away, and my heart sank.
I was no longer interesting enough for people to talk to at parties.
The Peak
Seven years ago, my life couldn’t have looked more different. My cofounder Emma and I used to host monthly parties for our startup, Dating Ring. We wore ironic tiaras, our eyes glazed over from free drinks, as people lined up to talk to us.
It was 2014, the height of startup heyday. Dating Ring had just gone through Y Combinator, the prestigious accelerator whose graduates include Airbnb, DoorDash, and Dropbox.
Our lives were playing out like a movie. A huge photo of Emma and me was featured in the NYTimes Style section, above a write-up of our company. We were fielding daily calls from reporters and producers. Exes came back from the dead, asking to grab drinks. People who had never spoken to me in high school were blowing up my phone. Investors were cold-emailing us. Revenue was going up and to the right.
When I stepped on stage at Demo Day to pitch our company to hundreds of investors, I had never felt so confident.
And then everything fell apart.
The Downward Spiral
When the dust settled after Demo Day, I knew we were in trouble. Investor meetings were more likely to involve sexist remarks than checks. Our biggest contribution — $100,000 — was revoked after our CTO left the company.
I’d heard that almost all dating companies failed. But I was confident that it was because they had almost all been started by men who knew little about love.
I’d thought what we needed were passionate founders who cared about making dating better. But I didn’t understand the industry — or startups — well enough. What we really needed? Millions of organic users. And a mobile app.
When I couldn’t fundraise enough money to champion either of those goals, I did my best to cut costs, to figure out how to maintain Dating Ring as a lifestyle business. Emma and I loved working together and with our team. We wanted to make it work.
We tried countless strategies — changing up our services and pricing model, creating a new website, testing every viral user acquisition strategy in YC’s playbook.
I spent late nights at our WeWork office, running the numbers over and over, making sure that we would always make payroll for our employees.
When the math started to look impossible, I knew someone had to go. I was out of ideas, depressed, and burnt out. I decided that someone would be me.
The Crash
I had been so consumed by my work that I had never stopped to picture what might come next. Or that there would be a next.
The past seven years of my life had been spent working — including weekends and holidays. I had started my first business back in college and then had gone right from that company to Dating Ring, without a day off in between.
But I went into the job search confident, optimistic that the YC brand and the connections I had made would open doors.
One of the first places I reached out to was a growth innovation firm that had hired me the year before and paid $1,000 for an hour of my time.
I spent a week before the interview organizing research and practicing my presentation: a strategy for a struggling media company.
Everyone was all smiles when I entered the fund’s glass-enclosed office on Madison Avenue and shook hands with the partners.
But when I finished my presentation, the team began rapid-firing questions at me, in a jargon I couldn’t understand.
increase the profitability ratio analyze the national inflation rate perform a SWOT analysis globalization churn efficacy core competencies disambiguate the ecosystem
I was in a dream, underwater, unable to move my mouth.
The interview was scheduled for two hours. But thirty minutes in, the founding partner picked up her phone. “Oh — really? Right now? Okay.” She hung up, ending the least convincing fake phone call performance I’d ever witnessed.
“We’re going to have to cut this short,” she told me.
I nodded and walked out. My mind raced on the Q train home as the wheels screeched on the tracks.
When I got home, I walked right past my boyfriend, crawled into bed, and slept for fourteen hours.
I didn’t tell anyone about that experience for two years.
The Pivot
The cold reality was becoming clear to me. I was 26 years old. I’d never had a ‘real’ job in my life.
I was the worst kind of fraud.
I had been celebrated as a gifted young founder. But now I was convinced I had never actually been intelligent. I was just hard-working and — up until then — good at faking my way through life.
I felt like I had spent the past few years lying to everyone. By showcasing all of the press I’d been in on my social media. By participating in the podcast season that had drawn millions of listeners. By taking investors’ money.
All of those congratulatory emails and messages I’d gotten now kept me up at night. What would everyone think when they found out my startup was a massive failure? And that I couldn’t even get a ‘real’ job?
So I focused all of my energy on doing whatever I could to ‘succeed’ in other areas in my life. I ran races. I became a top tutor. I saved money. I got a nice apartment. I wrote a young adult book. I got a literary agent.
Friends and family called what I was doing “a break”. They waited for me to pick up and start again.
But it wasn’t a break. This was my life.
Another Shot
Until the middle of 2020, when the father of a former student reached out. He was funding a new online tutoring venture — and he wanted to hire me to spend six months starting it.
I had spent months begging investors to back my dating company. Now I had an investor begging me to start a company. It was a dream come true for any entrepreneur.
I told him no.
What happened when the company was all set up and I was out of work once again? All of my hard work setting up my nice, comfortable life would be for nothing. I wouldn’t be able to afford my apartment. I’d have to apply for jobs. Again.
I couldn’t stomach the notion.
But the investor wouldn’t take no for an answer. Finally, I relented and agreed to a few hours a week.
A few hours a week quickly turned into twenty and then forty and then sixty. I tried to continue tutoring and writing at night and on the weekends so that I could immediately escape back to my safe haven when the six months were over.
Two weeks in and I realized I was unable to balance all three. More importantly — I didn’t want to. When I woke up in the morning and until I went to bed at night, all I wanted to do was talk to my team and work on the company. I was trying out tons of new technology and realizing how much easier it had gotten to run startups without engineers (thanks Zapier). I had found my way back to myself.
There was nothing wrong with the work life I’d had. I loved writing, but committing to it full-time was too lonely.
I wanted to be working with others, I wanted to be creating something, I wanted to constantly be thinking about how to fix problems.
The Solution
I’d gone about applying for jobs all wrong after my startup had failed. My wounds were still too fresh, my self-confidence too shaken. I’d been too ashamed to turn to the best network one could ask for — Y Combinator.
Because I was that silly Dating Ring girl who ran around in pleather shorts offering people shots of Fireball. Because my company didn’t even have an app. Because then, I’d had the chance to foster relationships with people who now ran billion-dollar companies, but I’d squandered it, convinced that my own gamble would pay off.
And because, as one of the few female founders in a male-dominated industry, I felt like I was letting female founders down everywhere. At the time, Dating Ring was only the second all-female founded company ever. Out of 693 companies. Even now, female-led YC companies make up only 3% of YC’s total portfolio valuation.
But I was done with excuses. Six years of shame had already prevented me from doing the work I loved most. Giving it my best shot meant I couldn’t ignore my access to the world’s best startup network.
I pulled up Bookface. (Yes, that is actually the name of YC’s internal social network…) I entered in my username and password.
Your username or password is incorrect.
I tried another.
Your username or password is incorrect.
My account had been blocked, I was sure of it.
I tried one last username. The site loaded. I was in.
Quickly, I wrote up a post, asking if there were any other founders who had moved into non-founder roles and would be open to chatting. I hit submit before I could second guess myself.
Then I sat in my bed and waited. I thought about what other founders from my batch would think. How they would pity me and shake their heads. How this might even hurt my chances at getting hired at current YC companies.
Minutes after, I glanced at my email. Two founders had booked a time to chat.
The New Normal
My body began to shake. I burst into tears.
My shame told me that I’d run out of favors. Lots of people had been open to talking in 2015, but I was six years too late to the game.
But that’s not how empathy works. It doesn’t run out. It’s not some finite amount of sand sifting toward the bottom of an hourglass.
The next day, my forum post had been included in the daily digest. Two calls turned into ten, which then turned into thirty. It turned out that I was far from alone in my struggles. So many other founders were also feeling lost — or had felt that way in the past. And not just founders who had ‘failed’ but also many who had had traditional success — companies that had been acquired or had achieved the mystical ‘unicorn’ status (a valuation of over a billion dollars). And even a few founders who wanted to tell me about job opportunities at their companies.
That shame I had hidden for so long was coming to the surface — and it was being washed away.
A New Lens On The Past
One of those founders who booked a call was Dan, the founder of a successful edtech company whom I’d loosely known and mostly lost touch with. I spent the beginning of our Zoom call apologizing for being a bad friend and self-obsessed founder.
He gave me a funny look. “That’s not my memory of you at all,” he said. “Do you remember that time I bought a Dating Ring gift certificate for my cofounder’s birthday?”
I nodded, although I had only a vague recollection of the email.
“The website didn’t work when I tried to buy it. You apologized profusely and then sent me the best personalized gift certificate email ever, complete with photos of your three-legged cat. I reread that email every year. I read it at my cofounder’s wedding.”
When I think back on my time in YC, I think — bad, narcissistic, clueless founder who didn’t answer half of her emails and never made time for friends.
There’s truth to some of that. But the shame literally blocks out the other parts — the great conversations I had, the friendships, the funny emails, the nights spent up til dawn chatting with my cofounder, dreaming about changing dating and the world for better, about having a chance at mattering, of being some of the first female leaders in a predominantly male space. I had just read Lean In. I was endlessly optimistic, naive, hungry.
Shame clouds our memories, rewrites history. It took me six years to reclaim mine.
Some Advice
If I could tell my 26-year-old “failed” self a few things, they would be this:
1. Startup failures are far more common than they appear. The more founders I spoke with, the more I realized my story was shared by so many others. The hidden shame, the fear of being found out. Because we hadn’t just had startups that had failed. Y Combinator had made us believe we had shots at creating billion-dollar companies — and that we’d blown those shots. At the end of the day, our companies were worth nothing. Many of us had lost hundreds of thousands, if not millions, of dollars.
Even though these stories are so common, they’re not the ones that crowd our newsfeeds. It seems like every week there’s a new Coinbase, a new YC company valued at billions of dollars.
But the news makes these successes appear much more common than they actually are. In reality, closer to 90% of startups fail. We just don’t hear about the failures nearly as often, and we fall victim to survivorship bias.
2. People only want you to fail if they themselves are unhappy. I wish I hadn’t been so concerned about what people thought about me after my startup failed. It’s easy to say that no one scrolls through social media, judging how others are doing. Unfortunately, I do think some people — even some friends — were excited for me to fail, at least in part. A bit relieved when people like me who posted ‘annoying’ Facebook updates and ‘peaked early’ fell flat on their faces. They are looking for that failure to validate their own life decisions because they wish they had the bravery to chase after their own dreams. Others’ failure makes them feel safer in their own life choices.
But no one who is truly content has time to waste on that kind of schadenfreude-scrolling. Once I started distancing myself from those people, people who are constantly putting value on others — always remarking on someone’s job status or weight or apartment size — I began to breathe a little easier. Brain space freed up. Space I could use to instead contemplate how to lead a life fueled by challenges and curiosity and mental well-being, rather than a life that would hold weight to a very small circle of status-obsessed people.
3. I was being unnecessarily harsh on my past self. I wasn’t some stupid girl running around offering people drinks. I was simply using the tools I had and doing what I thought was best. I was running a dating company. We had no money, we were bootstrapping, and what we needed most were more users.
You know who else ran around crashing sororities and frats and convincing drunk people to sign up for her dating app? Whitney Wolfe. The founder of Bumble, a dating company that recently IPO’d. I’m no Whitney Wolfe. Not even close. But the difference between massive failure and becoming one of the world’s youngest billionaires doesn’t always look that different at the beginning.
I had been doing the best I could with the limited life experience I had. And at twenty-three, I made a ton of mistakes. Often, I was a bad boss and a bad friend. I didn’t answer every email I got. I squandered many potential connections.
Yes, I may have been too focused on my own company’s success. But as my many calls with founders clarified — so was mostly everyone else. It was a three-month startup accelerator, a once-in-a-lifetime opportunity. Can we really blame ourselves for not being the Mother Teresa of startup founders, for not taking calls and helping people in addition to working 80 hour weeks as our companies barely got by?
Getting another chance at a startup this year proved that I’m not the same person I was at twenty-three. I have a much better understanding of the internal, rather than external, parts of work that bring me real joy — having good relationships with my coworkers, being so wired into a problem that I forget to eat all day, developing a new tool that saves someone time.
I know now that I wasn’t some terrible person that everyone hated. In reality, most people either didn’t remember me or never knew me to begin with.
4. Fundraising took a huge psychological toll on me. It’s still hard to know how to write about that time. I have been quick to compartmentalize it, to say that what happened was ‘shitty’ but that regardless, our company would have failed. I’m also aware that despite the sexism I faced, my white-cis identity means I had a more privileged experience than many others.
But I can’t discount how traumatic those experiences were. It’s impossible to quantify trauma and the long-term role it plays in the decisions we make. What could have been, if I had not experienced the requests for late-night meetings at hotels, the condescension, the lack of respect. Those weeks made a permanent impact on my self-worth and personal narrative.
Had I not felt so alone during that time, I might have been more open to reaching out to others, finding a new job, or even figuring how to pivot the company. Instead, I bowed out. Decided that kind of treatment wasn’t worth the fight. And because of that, I lost six years of meaningful work.
5. I’m learning to tell my own story. One key piece of advice a fellow founder gave me was: Don’t think back on that time as a failure — see it instead as growth.
When I think back on those years, I have so much to be grateful for. Dating Ring truly was the most action-packed learning experience of my life — giving me a crash course in user experience, operations, recruitment, product, operations, and growth marketing. I got to see the inner workings of an amazing podcast. And take part in Y Combinator, one of the most awe-inspiring and generous networks. I got to work with the most amazing people, including my cofounder Emma, who is still a close friend, and our head of operations, Shearly, who joined my team this year as well. Shearly agreeing to work with me again was so restorative, a reminder that the narrative I’d told myself about my past was not shared by others who had been there alongside me.
Dating Ring gave me the incredible opportunity to talk to thousands of users, to hear the personal stories of so many different people. Since then, many couples have gotten married and had kids. Which is a pretty cool legacy to leave. Looking back, I can’t imagine a better job for someone who had just graduated with a degree in love — even if it didn’t work out in the end. And to add a bow on top — through Y Combinator, I even met my fiancé.
6. And finally: Don’t let shame hold you back from doing what you love. I thought that applying to jobs meant rewriting my entire past and chalking it up to wasted time. I now know that couldn’t be further from the truth.
I’m done hiding now. I’m Lauren, my startup failed, and I am now looking for jobs in operations and product.
Nice to meet you.
By Lauren Kay
