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Leaving the Structure Behind

May 1, 2026 · What makes a life better?

Over the last year, I started my founder journey by trying to solve a problem I had felt firsthand at Bain: watching smart people spend too much time on manual workflows that should have been automated.

It started with an unexpected high. We got into YC the first time we applied — before writing a single line of code. For a moment, it felt like the startup script was working. Two months later, I left YC mid-batch after a co-founder split.

After leaving, I had to decide whether I still wanted to keep building. I was now on my own, but I already had customer calls lined up, so I kept going. I kept taking discovery calls, listening to users, and following the pain points that kept coming up. That eventually led me to PowerPoint automation tools, which I continued building and ultimately sold.

Along the way, I learned more than I expected — about what it means to operate as a founder, how to sell and earn trust, how to keep doing the hard work when the path is uncertain, and how to stay open to failure without letting it define the outcome.

#1 Learning: People matter more than almost everything. But choosing the right people is only half the lesson — the other half is learning how to communicate before misalignment turns into something bigger

When we started, I thought a strong founding team meant smart people with complementary skills. That is part of it, but it is not enough. In a startup, you are not just choosing someone’s skill set. You are choosing their judgment under pressure, their sense of urgency, their communication style, their empathy, and their ability to make other people feel safe taking risks with them.

Some of our misalignment showed up first in small operational moments. At the time, I treated those moments as isolated frustrations. Looking back, they were early signals that we had different instincts around urgency, risk, ownership, and how decisions should get made under pressure. The bigger issue was not any single title or task. It was that we had not fully aligned on roles, responsibilities, decision-making, and what each person needed to feel ownership and trust in the team.

At the time, there were also real external constraints — including immigration-related ones — that made every decision feel more urgent. I felt like I had limited room to slow things down, push for clarity, or walk away cleanly, so I told myself it was better to keep moving. Looking back, I should have paid more attention to the discomfort I was feeling. When your gut keeps telling you something is not right, it is usually pointing to something real, even if you cannot fully articulate it yet.

I had raised some concerns, but we had not truly resolved them. By the time those concerns came up again, they landed much harder than they might have if we had kept the conversation open from the beginning. From my side, the concerns had never fully gone away. From the other side, they may have felt sudden, personal, or unfair. My concerns were real, but I could have communicated them with more care, more context, and much earlier.

That experience taught me that unresolved concerns do not disappear just because the team keeps operating. Silence can look like alignment from the outside, but inside, it often turns into resentment. I also learned that directness and care are not opposites. Being direct early — and staying in the conversation until there is real resolution — is often the kinder thing to do.

A better version of me would have said earlier: “I’m feeling some misalignment around roles, responsibilities, decision-making, and how we’re operating as a team. I don’t think this is fully resolved yet, and I want us to talk about it before it turns into resentment.”

Cofounder communication is not a nice-to-have. It is one of the most important operating systems of the company.

#2 Learning: Not all validation is equal: accelerators, VC money, and praise validate the narrative; customers using, returning, waiting, and paying validate the business

After the split, I left the original company structure, and with that, I also left YC. There was no funding, no accelerator badge, and no longer the founding team I had started with.

What I did still have were customer conversations lined up.

That forced a very clarifying question: without YC, without funding, and without the original team, was there still something real here?

Getting into YC had made the company feel real from the outside. But after leaving, the only thing that mattered was whether customers still had the problem, whether they were still willing to talk, and whether I could build something useful enough for them to care.

In a few days, I had to pull the logistics together, keep the conversations going, and prepare demos with very little structure around me. It was a tough period, but in some ways it clarified my own motivation. There was not much external momentum left to hide behind. What remained was simpler: I still cared about the problem, I still had customers willing to talk, and I still wanted to see if I could build something useful.

There were long hours and a lot of uncertainty, but I managed to keep the thing alive. And that phase taught me a different kind of validation.

Prestige, funding, and compliments can validate the story. But customers giving you their time, trusting you with their workflow, waiting for a solution, and eventually paying for it — that validates the problem. I learned that the strongest validation is not when people like your idea. It is when they make room for it in their actual work.

#3 Trust is the real strategy: Genuineness builds trust, and trust is what makes people want to work with you

I first learned this during my days at Bain. The strongest client relationships were not built by overpromising or pretending to have every answer. They were built by being honest, thoughtful, and useful enough that clients wanted to keep working with you.

At a big company, a certain amount of trust comes with the logo. When I was at Bain, the brand entered the room before I did. Clients might not know me personally yet, but they already had a reason to believe the work would be high quality.

As a founder, that changed. My previous experience helped me get some conversations, and the relationships I had built still mattered. But once I was no longer operating under a big company’s name, trust was no longer automatic. I had to earn it directly.

That is easier said than done. Early customers know your product is imperfect. They know you are still figuring things out. So the question is not just whether the product works. It is whether they trust you to understand their problem, be honest about limitations, move quickly, and keep showing up.

That is why genuineness mattered so much. Nothing worked better than being honest, specific, and useful: showing up in person when possible, listening carefully, acknowledging what the product could and could not do, customizing around real needs, and following through quickly.

I learned that early sales is not about performing confidence. It is about earning trust one conversation, one demo, and one follow-up at a time.

This also shaped how I thought about outreach. I was skeptical of generic AI-generated messages from the beginning because consulting had taught me that trust is built through specificity and context. When you are early, the goal is not to sound polished at scale. It is to make the customer feel like you actually understand their world.

Lesson #4: Patience is the foundation of resilience: it helps you stay clear-headed when feedback is slow, ambiguous, or not what you wanted

Patience is extremely important when feedback is no longer instant.

In a big company, feedback is built into the system. At Bain, I valued that culture a lot. You get feedback from managers, teams, clients, staffing, reviews, and performance cycles. You know where you stand, what to improve, and often what the next step should be.

When you are building your own thing, that structure disappears. There is no manager telling you whether you are doing well. There is no performance review that turns ambiguity into a clear development plan. There is no guaranteed next step.

That also means there is no one else deciding what matters most. One of the hardest parts of being a founder was learning how to prioritize when everything felt urgent: customer calls, demos, product decisions, logistics, sales, follow-ups, and my own doubts. In a big company, priorities are often shaped by the system around you. When you are building alone, prioritization becomes your job. You have to decide what is actually important, what is merely noisy, and what can wait.

A lot of the time, you are operating in uncertainty. You try something, and it does not work the way you hoped. You talk to customers, and the signal is mixed. You build a demo, and the reaction is unclear. You think you are close, and then something changes. That is where patience becomes important. Not passive patience, but the kind that lets you stay calm long enough to think from first principles. What is actually true? What did the customer actually mean? What problem keeps showing up? What assumption failed? What is the next useful experiment?

The hardest part is that customer feedback is rarely straightforward. This also reminded me of change management: most people do not want to change how they work unless the new solution is much better, or the old way has become too painful to tolerate. And even when they say no, the reason they give is not always the real reason. There can be a million stated reasons — budget, timing, workflow, priorities — but underneath, the real question is often whether the pain is urgent enough to change behavior.

Patience gave me enough space to separate surface-level feedback from deeper signal. It helped me avoid reacting emotionally to every setback and instead ask what the market was actually telling me.

Lesson #5 - Balance being a dreamer with being realistic

I did not land on PowerPoint automation1 immediately.

In fact, I had understood the pain from the beginning. Coming from consulting, I knew how painful slide creation and manual workflow cleanup could be. I also knew it was a hard problem to solve well, so early on I tried to explore adjacent ideas instead.

But after leaving YC and continuing customer conversations on my own, the same pain kept resurfacing. People were still spending too much time on manual slide work, and the problem was concrete enough that they could describe it immediately. Eventually, I realized I was being pulled back to the problem I had avoided because it was hard. So I decided to go back to the hard problem.

That became another lesson for me: hard problems are not always the wrong problems. Sometimes they are hard because they are real. The important question is not whether a problem is difficult, but whether the pain is persistent enough, specific enough, and valuable enough to be worth solving.

For PowerPoint automation, I also had to learn what the right version of the solution looked like. The answer was not always “generate slides with AI.” In many professional workflows, consistency matters more than novelty. People care about control, formatting, brand standards, repeatability, and knowing exactly what they are going to get. For those use cases, template-based automation can be more valuable than fully generative output.

Building it showed me there was real value. People found the product genuinely useful. It solved a painful workflow problem and saved them time in a way they could immediately understand. But usefulness and upside are not always the same thing. The market, the timing, the competition, the workflow complexity, and my own appetite for spending the next several years on this particular problem all weighed on the decision.

That was part of why selling felt right. It allowed the product to continue existing for people who found it useful, while giving me space to move toward problems that felt closer to the kind of impact I wanted to work on next. To me, that is the balance founders have to hold: dream enough to take on hard problems, but stay realistic enough — about the market, the business model, and yourself — to know when to pivot, sell, or move on.

A new chapter

I would not call this past year wildly successful by the usual startup measures. There was no massive outcome, no clean arc, and no headline moment.

But it changed how I think. It taught me more than almost any year I can remember — about people, trust, patience, customer pull, and my own judgment under pressure.

Some of these lessons were things I had read about before, but I never fully understood them until I earned them through the messy parts: the high of getting into YC, the pain of leaving, the uncertainty of continuing alone, the discipline of listening to customers, and the humility of knowing when to move on.

I will carry these lessons with me. I am writing them down because I hope they are useful to someone else, too.

Now, on to the next chapter.

here are the links to the things I built:

If you are working on similar problems, exploring workflow automation, or just curious about the building process, I’d love to chat!

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