YC Startup School pushed me to think bigger without leaving my own track

Two comments from YC Startup School stayed with me.

Boris Cherny said, “Maybe don’t listen to the LinkedIn influencers.”

Alexandr Wang said, “Top advice: ignore LinkedIn.”

My takeaway was simple:

More Twitter/X and less on LinkedIn.

That is a strange way to begin an article on LinkedIn, but it is true.

One reason I have been able to follow AI developments closely and adopt new tools quickly is Twitter/X.

It is probably the social platform I have used the longest and most consistently. People often share what they are trying before it becomes polished content.

Twitter/X helps me notice new tools and ideas early. I find out whether they are useful by applying them to problems I already have.

But the more personal takeaway from the trip was confidence.

I hope this story encourages someone with a less conventional background to build something of their own.

Returning to San Francisco with something of my own

Last year, I applied to attend YC Startup School and was not selected.

I still travelled to the Bay Area for the first time, attended the surrounding events, and found my way into the community.

That trip made me realize something uncomfortable.

I had years of experience as a product person and many pages of ideas, but I did not yet have something I could point to and proudly say:

I made this.

One year later, I returned to San Francisco with Joe Speaking.

Joe Speaking began as a tool to solve my own English-speaking problem. I was its first user, and it helped me achieve the language score I needed. Since then, it has grown to over 1,700 fully organic users and more than 130 paying users.

It also became my first iOS app.

At Startup School, I met people from top universities, research labs, and major technology companies. Many were younger than me and had credentials that looked far more impressive on paper.

A year earlier, that might have made me question whether I belonged.

This time, I felt proud of myself.

I no longer needed a famous university, company, title, or investor to explain who I was. I had put something real into the world, and people were using it.

Building became my credential.

Startup School did not give me that confidence. It helped me recognize that I had already earned it.

While I was drafting this article, Paul Graham posted this:

Confidence comes from evidence

Over the past year, I went from being a product person to someone who could turn a personal problem into a product and ship it.

I learned to build, debug, distribute, support, and improve it.

Even while travelling around San Francisco, I remotely shipped one iOS release, three web releases, acted on feedback from three users, and burned through roughly 4.4 billion tokens.

That pace still feels slightly unreal to me.

Boris Cherny’s session helped me understand why some people become much more effective with tools such as Claude Code.

There is no single secret prompt. His advice was to approach the model empirically: give it difficult work, give it ways to verify its output, observe where it struggles, and adjust the prompt, context, tools, or workflow.

That closely describes how I learned.

I did not get better at using AI by collecting prompt templates. I got better by testing the tools against problems I actually needed to solve. The results told me whether my approach worked.

AI did not remove my responsibility. I still had to decide what to build, understand users, judge the output, and make tradeoffs.

AI amplified my agency.

At the same time, this trip reminded me that one person is not enough for everything.

Tools helped me do more on my own. The people I met changed what I thought was possible. They also brought the judgment, trust, and perspective that tools cannot provide.

I was still a little strange at Startup School

Many conversations naturally centred on enormous markets, rapid growth, fundraising, and the newest technology trends. That energy is part of what makes Startup School valuable, but my own path has been different.

Joe Speaking was a product, an experiment, and a way for me to learn. I built it because I genuinely needed it, not because the problem was fashionable or easy to pitch. I even put my own name in it.

AI gives me unusual freedom to follow that instinct. I can now explore an idea, build it, distribute it, and support users on my own. Moving faster, however, makes the choice of direction more important. AI cannot tell me what I should care about.

Peter Steinberger’s presentation was one of the sessions that encouraged me most. It reminded me that following your curiosity and building something you personally want can be a valid path, even when it does not fit a conventional startup template.

After his session, I spoke briefly with a YC partner. I shared my background, why I had built Joe Speaking, and what I wanted to explore next.

Joe Speaking has become useful to a group of users and grown further than I expected. But I do not want to force it into a story designed for YC or fundraising before I understand what the larger company should become.

I may apply to YC later, when the product, opportunity, and ambition genuinely fit. For now, I felt comfortable saying:

Not yet.

After Peter’s presentation, I posted this on X:

That may be the best summary of my trip.

It is not anti-ambition. It is a refusal to perform ambition for other people. Building for myself means starting from a problem I understand deeply, listening to users, and seeing how far it can go before I claim it is something bigger.

Maybe feeling a little out of place was part of finally finding my own track.

Staying on my own track does not mean thinking small

Authenticity can also become an excuse.

“I am staying on my own track” should not mean “I am afraid to think bigger.”

Startup School challenged me here.

Alexandr Wang framed the current moment as a once-in-a-civilization opportunity. The question I carried away was:

What kind of world do I want my work to help create?

I am good at identifying a concrete problem and building a practical solution. I am still learning how to connect those solutions to a much larger vision.

Sam Altman argued that coding agents have raised the ceiling of what a small team can attempt. They can help a small team pursue work that previously felt out of reach, not just complete familiar work faster.

Blake Scholl’s story made that ambition tangible in the physical world. He came from software rather than aerospace, yet built toward an economically viable supersonic airliner. His story reminded me that better technology does not automatically create a better future. Someone still has to build the products that move it forward.

I have long been interested in products that bridge the physical and digital worlds. I do not yet know what form that will take, but Startup School pushed me to look beyond the product immediately in front of me.

Later, at a fireside conversation with Vinod Khosla, the message became even more direct: dream bigger, take more risks, and accept the possibility of failure.

For me, that means taking my own path further than I initially thought possible rather than copying someone else’s company or definition of success.

“How hard can it be?”

Jensen Huang’s session gave me another way to think about confidence.

NVIDIA did not begin with the correct technical approach. Jensen explained that when the team finally confronted that reality, they bought textbooks, learned what they needed to learn, and rebuilt.

His lesson was simple: great founders do not already know everything. They are willing to face reality and learn.

He described an attitude he still brings to unfamiliar problems:

“How hard can it be?”

The honest answer is usually: much harder than you initially think.

But imagining all the suffering in advance can create enough anxiety to stop you from beginning.

Instead, begin. Learn what today requires. Then work toward tomorrow.

Jensen described resilience as something practised every day, not only during one dramatic crisis.

That message felt personal.

Last year, I did not know how to build the product I now operate. This year, users occasionally wake me up with support messages.

Those are new problems, but they are problems I am grateful to have.

Resilience does not mean repeating the same idea forever or pretending that everything is working. It means facing reality, learning quickly, changing your approach, and continuing.

Not knowing something is not a permanent identity.

You can learn your way there.

When online connections become real meetings

The talks were inspiring, but many of the most meaningful moments happened between the sessions.

At a Google DeepMind after-party, I met Logan Kilpatrick and showed him what I had built with Gemini Live. Being able to give feedback directly to someone behind a product I had followed and used felt completely different from submitting a form or writing a post.

I first met Nolan Lwin at Founders, Inc. We met again at Startup School, and later at a coffee shop he recommended.

At that coffee shop, almost everyone around me seemed to be working on a YC application, except me.

When I returned from the restroom, someone stopped me. To my surprise, it was Mark Nakatani. We had tried to meet during Startup School and missed each other, only to run into one another there later.

I also finally met Nelson Lee in person after knowing him through X for years.

There were thoughtful conversations, new friendships, after-parties, and even builder hotpot.

Some of these meetings may have felt ordinary to the other person. To me, they carried years of context.

When you have followed someone’s work, used something they built, or interacted online for a long time, meeting in person changes the relationship.

A profile picture became a person, and posts became a conversation. I could finally discuss a product with someone who had helped create it.

Online platforms helped me find these people. Meeting them in person added the attention, spontaneity, and shared memories that online interactions could not.

AI can help me research someone, understand their work, or prepare a thoughtful question. It cannot manufacture the excitement of finally meeting them or the moment when someone recognizes me in a coffee shop.

I am grateful for the people I finally met and for the new friendships that began during this trip.

Try to be useful

Sam Altman also discussed how valuable networks often grow from genuine curiosity and helping people rather than treating every conversation as a transaction.

That matched my experience.

I did not enter every room with a specific target. I shared what I was building, listened to other people’s stories, asked questions, and allowed unexpected conversations to happen.

This is also how I want to think about my personal brand.

To me, a personal brand is the memory people build from what you repeatedly do, not just a polished profile or job title.

Sometimes helping means sharing what you know or making an introduction. Other times, it means offering useful feedback or simply caring about what someone is trying to build.

Writing this article is one way I can do that.

I am still early, and I have not figured everything out. But perhaps sharing the honest version of my journey can help someone else begin sooner, feel less intimidated, or trust their own path a little more.

I want what I publish to make me more useful and more real, not more performative.

What San Francisco and Ottawa each give me

On my way to San Francisco, I saw this post. It captured exactly how I felt:

When you are in San Francisco, especially at a YC event, ambitious ideas feel normal.

Conversations begin with agents, models, infrastructure, distribution, and products that were impossible only a short time ago. Startup thinking seems to spill into ordinary places.

That density is powerful, but it is still a bubble.

Outside it, many people have not meaningfully used an AI agent. Many businesses are only beginning to understand what current tools can do.

For me, the ideal rhythm may be to visit San Francisco periodically, absorb the ambition and meet people, then return to communities where the problems and level of AI adoption are different.

I sometimes imagine what would have happened if I had moved directly to the Bay Area instead of living in Ottawa.

I might have become more connected or built faster. I might also have optimized too quickly for the conversations around me.

Ottawa gave me distance. It gave me time to explore freely and gradually develop my own direction.

That distance limited my access, but it also gave me room to become different.

San Francisco shows me what is possible. Ottawa reminds me how many people have not benefited from it yet.

I also met many Canadians during the trip, and a surprising number came from Waterloo.

That left me thinking about Canada’s talent ecosystem. Canada is excellent at educating talented people and attracting ambitious immigrants, but how can it create more places where ambitious builders repeatedly encounter one another? How can it give them stronger reasons to take risks and remain long enough to build the next generation of communities?

I do not have a complete policy answer.

But as an immigrant building in Canada, I hope the country can become more than a place that develops or attracts talent before exporting it. This is also part of my own Canadian builder story, which I wrote about here:

What I am taking home

Last year, I travelled to the Bay Area with ideas and uncertainty. This year, I returned with a product, real users, more confidence, and new friends from around the world.

Startup School felt like a reward for the work of the previous year. It also reminded me that personal achievement does not need to follow someone else’s template.

You do not need to chase every trend or shape yourself for investors and algorithms. Start with something you genuinely care about, keep learning, help others, and build something you are proud to share.

I still do not know exactly what I will build next or who I will be when I return to San Francisco.

But I know how I want to continue:

Be real.

Be yourself.

Help others genuinely.

Think bigger.

Stay on your own track.

Thank you, Y Combinator, for bringing so many ambitious, thoughtful, and generous people together.

(Built entirely by Opus 5 from my own photos and recordings. Thanks to Boris!)