Looking back, it might have been a disaster if I’d gotten into Y Combinator with my first application.
That’s probably not what you’d expect a tech founder to say, but it’s true—even if I couldn’t see it at the time. For years, I pounded on the front door of the world’s leading startup accelerator and they wouldn’t let me in.
But if Y Combinator hadn’t rejected me on my first attempt—or my third, or my sixth—I wouldn’t have been ready for everything they threw at me when I did get accepted. And I don’t know if I’d be the entrepreneur I am today.
Here’s everything valuable I learned from my five-year odyssey, including what it took to get in on the seventh try.
Why Y? How Getting Into Y Combinator Can Change Everything
Y Combinator is the gold standard of startup accelerators. The concept is simple: startups apply and, if selected, are put into Y Combinator’s version of startup hyperdrive. Initial funding, mentorship, support, help with networking—the works.
Legendary tech behemoths have emerged from YC: Airbnb, Coinbase, DoorDash, Dropbox, Instacart, Twitch, Reddit, and Stripe all went through the YC accelerator program. It’s the startup Ivy League. Who wouldn’t want in?
Unfortunately, I didn’t know how much had stacked against me when I arrived in Silicon Valley.
First, I was young. I was in my early twenties, which isn’t necessarily unusual for startup founders, but I was the clueless kind of young. I didn’t have any tech background, experience, or skills—just a wild dream of making it into YC someday, somehow.
I was also an outsider. As a European immigrant new to the U.S., I didn’t know anyone. I didn’t have a network of tech insiders I could ask for mentorship or a foot in the door. Hell, I didn’t even speak English very well. I would need to build everything from the ground up—not just my startup, but my entire life.
I thought if I could just get into Y Combinator, none of that would matter. I would emerge from the startup accelerator program as a full-fledged tech titan, no different than my Silicon Valley heroes.
An Ambitious Idea isn’t Enough
Early in our careers, founders often romanticize the idea of the startup. We have the Hollywood version of the tech founder story playing in our heads 24/7. And the only thing standing between us and a future where Joseph Gordon-Levitt plays us in a movie is: money.
My thought was simple: “If I raise money, I’m successful.” I thought that if I ever landed a million dollars in funding—that’s it. I would have made it. It would take me years to learn that raising money isn’t the goal. It’s a means to an end and it’s pointless if you don’t actually have a business.
And I didn’t have a business. I had an idea for a business—one that I was convinced would change the world!
My first idea was an online education platform called Supercool School. It was in 2007, during the Web 2.0 boom, so user-generated content was on the rise, and online education seemed like an obvious opportunity. Change education, change the world. That’s an idea worth investing in, right?
I even thought my idea was more important than other startups that were hitting the scene at the time. “Airbnb? Just a website to rent your couch to cheap travelers? That’s nothing! My idea is going to revolutionize education!” Ah, the hubris of a young entrepreneur.
Still, I thought if my idea was ambitious enough, maybe Y Combinator would let me in.
But what I received wasn’t an all-access pass to the Silicon Valley dream. Instead, it was a humbling, generic rejection letter from YC.
Clearly, I needed more than just a big idea.
Stop Playing Entrepreneur Instead of Doing the Hard Work
Looking back on it now, I know my problem was that I was playing the idea of entrepreneurship. I was content to daydream about my future success and talk about it to anyone who would listen. It’s not that my idea wasn’t good enough, it’s that I was simply pre-successful.
I was good at getting people excited about my grand ideas and future plans—friends, family, strangers in bars. That kind of optimism and ambition can be a strength, but it can also become a distraction that prevents you from doing the hard, gritty work of building a business.
I was drawn to the distractions and ended up focusing on the wrong priorities—picking out a logo, branding, polishing slide decks, etc. I was practically planning future company retreats for a company that didn’t exist yet!
As an entrepreneur, you need to learn the difference between “being busy” and moving the needle. You can waste entire days tackling the lowest-risk, lowest-consequence activities. If you do it long enough, you can convince yourself you’re “grinding” and “paying your dues.”
But that busy work doesn’t actually move the needle. It’s simply roleplaying the idea of entrepreneurship.
As I kept spinning on my hamster wheel of work that went nowhere, the rejections from Y Combinator kept piling up. Every six months, I would apply, and every six months, I’d get that same generic rejection letter.
Rejections from YC sting. It’s a “no” from the people whose validation you want most in the world. But you can’t let yourself avoid this sting by avoiding the hard work. Instead, have a heart-to-heart with yourself and ask the critical questions:
- What if what I’m working on isn’t going to move the needle? Ask yourself: “Is this the best use of my time?” If you’re focused on branding the business rather than building the business, the answer is probably no. Make it a regular habit to gut-check yourself so you’re not always pursuing vanity work.
- Am I doing busy work that feels productive, but won’t impress anybody at Y Combinator? Ideas alone don’t impress serious tech heavyweights. Get a business plan, recruit people who can build something, solicit feedback and iterate on it. Prove that you’re always moving forward, not sitting around waiting for funding.
- What is the most viable idea I have for a startup? Be honest. Does your idea lean on the prospect of being a “game-changer” too much? Or does the idea solve a practical, real-world problem? If you look at the list of Y Combinator success stories, you’ll see platforms that didn’t look like they would change the world. But because they offered practical consumer solutions at scale, they did. Your idea needs to work on a practical level first.
These lessons took me a long time to learn. I had been treating YC like a lottery: If I kept buying a ticket, maybe I’d win.
But I had to try a completely different approach if I expected a different outcome.
The Proximity Rule: Keep Meeting New People Until You Find the Right People
No one likes to hear the advice, “It’s all about who you know.” But there’s some truth to it.
I learned that in order to level up my progress, I needed to spend less time with other daydreamers. I needed to find out what really created startup success. Call it the “proximity rule.” If you put yourself near people with successful habits, eventually, you’re going to cultivate success for yourself.
In my early applications for Y Combinator, I spent a lot of time cultivating relationships with people who were well-intentioned and enthusiastic…but ultimately, many of these people were just as clueless as I was.
If you’re already an outsider like I was, you have to expand your circle of influence.
Success tends to leave breadcrumbs. Rather than focusing on networking with other “wantrepreneurs” who are in the same boat, you should get outside your comfort zone. Eventually, you’ll find people with genuinely helpful experience.
While you shouldn’t exclude anyone simply because they’re not as successful as you’d like, you should be proactive about meeting people with different backgrounds and perspectives. Every new person you meet is an opportunity to find the right people for you.
It’s the same approach Jeff Bezos took early in his career when he wanted to start dating. He started attending ballroom dance classes. He wasn’t particularly interested in ballroom dancing—he just wanted to increase the chances he’d meet someone.
After a few years immersed in Silicon Valley, I gained traction by meeting more tech people, attending more events, and building a network of talented people who could teach me things I didn’t know.
The lesson is simple: don’t just dream about success. Go out and meet it.
For me, I was lucky enough to meet Anthony Nemitz and Tom Steinacher, two talented young developers who I immediately recognized as being special. I knew I wanted to work with them one day, even if I wasn’t sure how yet.
Focus on Pulling the Levers that Matter
I’ll fast forward to the death of my first startup, Supercool School (R.I.P.).
I tried six times to get into Y Combinator with that idea. All I had to show for it was six rejections.
After years of banging my head against the wall trying to make it work, I was finally honest with myself and admitted defeat. As soon as I let go of my first idea, I felt like a weight had been lifted. I was free to return to the drawing board, wipe it clean, and start over. Immediately, I had a new idea I was excited about.
For my next startup, I partnered with Anthony and Tom, the two talented developers I had met in the Bay. The result was SwipeGood: a charitable giving app that lets users round up their transactions to effortlessly donate to the charity of their choice.
With this new idea, I didn’t waste time with all the bullshit that had slowed me down before. I had made enough painful mistakes to know which were the right levers to pull to make real progress.
Those levers were:
- An idea that worked: SwipeGood wasn’t going to change the world, but it did provide a practical solution to a charitable giving problem.
- A strong team: With Anthony and Tom aboard, I had talent ready to build an early version of the app. A strong team takes idle daydreams and turns them into practical solutions.
- Rapid prototyping: You can’t expect to impress Y Combinator with just an idea. Rapid prototyping will teach you the most important lessons quickly: what works, what doesn’t work, and what it’s going to take for your product to succeed.
- Real user feedback: With a prototype in place, you can take your product to users. What are the blind spots you can’t see? User feedback will shore up your weaknesses by the time you apply.
Will all of these levers pulled, I had something my first idea had been lacking: momentum. By the time I applied to YC with SwipeGood, the rapid iteration and working proof of concept meant I was finally a serious contender.
My Acceptance Into Y Combinator
I decided that on my seventh attempt, I wouldn’t treat my YC application like a lottery ticket. I would be more strategic.
I met with founders who had gone through YC and I pitched them our idea for SwipeGood, asking for their expert feedback. I got mixed reactions—some founders thought the idea sucked, and others were more encouraging.
One founder was excited enough about SwipeGood that he emailed his recommendation to Y Combinator co-founder Paul Graham directly. Two hours later, Paul emailed us back with an invite to the program.
On the one hand, it blows my mind that once I finally had a viable startup idea, it only took two hours to get accepted into YC.
On the other hand, I knew that it really took five years for me to learn all the things, make all the mistakes, and meet all the people it took to become the kind of entrepreneur who could get into YC. It was an overnight success five years in the making.
The YC experience was completely transformative. Within two weeks, we successfully raised $1.2 million in funding.
What else did we get from our YC experience?
- Mentoring from founders like Paul Graham, who taught us how to build a company the right way
- An environment that forced us to move much faster and generate more traction with rapid iteration
- Prioritizing the right things and high-impact work
- Identifying which metrics to focus on and how to make those numbers grow week over week
- Exposure to a community of the other creative, talented founders
- Raising money much more quickly (and successfully) than if we’d done it alone
All the lessons I learned in YC became the foundation for the company I run today, Close, a B2B SaaS company with $30 million in ARR.
How to Use My Y Combinator Experience to Become a Better Entrepreneur
If you’re a young entrepreneur filled with big dreams and few ideas about how to make them a reality, here’s what I’d tell you:
- YC is not a lottery. You can’t just keep buying tickets and expecting to get in. You have to do constant work outside of YC. Focus on growing yourself into the kind of founder who would get into YC. Meet new people. Do hard things. Iterate new products and prototypes rather than polishing slide decks. Seek out real user feedback.
- All roads leading to YC are different. My journey to YC was slow, largely because I didn’t know what I was doing. Maybe if I’d been born in Silicon Valley or gone to Stanford or knew how to code, it would have been a lot smoother. Your road, too, will be completely different—you’ll have different advantages, disadvantages, and lessons to learn. And anyone who tells you they know the “one surefire way” to get into YC is probably full of shit.
- Embrace rejection. Rejection can teach you more than success. If you do big things, you’ll invite more rejection into your life. That’s just part of the trade-off. Learn to take it in stride. “No” is just a word with two letters. Get comfortable with it.
Are you a B2B SaaS founder trying to scale your business from the ground up? Check out the rest of this series, The 0 to $30 Million Blueprint, where I share more of my lessons and advice from over a decade of scaling a B2B SaaS company.
