5 Brutal Lessons My First Startup Taught Me — And How I’m Building Smarter This Time

Starting a business is thrilling — until it’s not. My first startup left me with scars, wisdom, and a lot of journal entries. Here are the 5 brutal but beautiful lessons I learned the hard way — and how I’m applying them as I build my new venture, a self-dating app that’s rewriting the rules of connection.

🧨 Let’s Just Say… Startup #1 Didn’t Go as Planned

I did what a lot of first-time founders do: I jumped in full of ambition, high on vision, and ready to grind until it worked.

Spoiler: It didn’t.

The app flopped. The team fell apart. I burned out. And honestly? I questioned whether I was cut out for any of it.

But here's the twist: that so-called failure? It gave me everything I needed to build this new startup — a self-dating app — with clarity, emotional maturity, and actual self-respect.

These are the 5 brutal lessons my first startup handed me — and how I’m using them as armor and fuel this time around.

💣 Lesson 1: "More" Doesn’t Mean Better — It Just Means Burnout

At my first startup, I wore the hustle like a badge of honor. I worked 14-hour days, skipped sleep, skipped meals, and kept pushing. I dreaded every email, every phone call, every meeting. I even responded to emails while on vacations.

But you know what I wasn't doing?Thinking clearly. Testing thoughtfully. Taking care of myself. Don't get me wrong, startup world is not for the faint of heart but if you run on empty tank, then you won't run far.

What I’m Doing Differently Now:

• Fewer features, deeper purpose

• Weekly pause points for product decisions

• A non-negotiable solo ritual every Friday (aka “self-date night”) to stay sane

I no longer worship at the altar of productivity. I build slow and smart.

🔍 Lesson 2: Build for the Problem, Not the Hype

I got swept up in the hype. Everyone was building X for Y. VC-backed. Buzzword-filled. And I did the same — until I realized I was building a solution in search of a problem.

It was tech-first, not human-first. We didn’t truly understand our users. We didn’t care enough to.

What I’m Doing Differently Now:

• Deep user interviews before line one of code

• Designing around emotions, not just features

• Building with people, not just for them

This time, the mission is real. The people I am building for are me, and you, and every person craving a healthier relationship with themselves.

💔 Lesson 3: Emotional Avoidance Will Destroy a Team

I didn’t talk about feelings. I didn’t ask my co-founder how they were really doing. We didn’t check in — just checked off tasks.

That emotional silence? It bred resentment. Confusion. Misalignment. Eventually, it broke us.

What I’m Doing Differently Now:

• Emotional check-ins baked into meetings

• Building a team culture rooted in emotional honesty

• Working with people who believe in relational leadership, not just results

I’m not afraid to say “I’m overwhelmed” or “I don’t know” anymore. That’s not weakness — it’s data.

🧩 Lesson 4: Product-Market Fit ≠ Founder-Life Fit

We had some small traction. I had users. But I was miserable. I didn’t believe in the mission anymore, and the work drained me.

I stayed in it way too long because I thought success meant suffering.

Turns out, if you build something that doesn’t align with your values or lifestyle, it’ll wreck you — even if it “works.”

What I’m Doing Differently Now:

• Gut checks before roadmap decisions

• Designing a company culture that prioritizes wholeness

• Asking myself regularly: “Is this feeding me or just feeding the algorithm?”

This time, I’m building something that heals me, too. Because if it’s not sustainable for me, it’s not sustainable for anyone.

🤯 Lesson 5: You Can’t Build Connection From Disconnection

At my last startup, I was lonely. I wasn’t taking care of myself emotionally. And I was trying to build community and connection from that place of disconnection.

Sound familiar?

It’s no wonder the product didn’t land — I wasn’t even connected to myself.

What I’m Doing Differently Now:

• Self-dating as a non-negotiable practice

• Building in public to stay grounded and real

• Focusing the product around intentional, inner connection — not just dopamine hits

The irony? The best way to build a “connection” app is to first build a deeper relationship with yourself. That’s the entire ethos of this new app.

✨ Final Reflections (Because We Don’t Do "Conclusions" Here)

If you’re reading this and in the middle of a messy startup story — trust me, I’ve been there.

I’ve been the burned-out founder on the bathroom floor.The one googling “how to pivot gracefully” at 3am.The one wondering if I should just get a normal job and quit this whole thing.

But I didn’t quit. I recalibrated.

And now? I’m building something that feels true. Something that might just change the way we see love, starting from within.

So if your first (or second) startup broke you a little — good. Let it break you open. Let it teach you. Let it give you the blueprint for your next glow-up.

💬 FAQ

Q: Should I start another startup after failing one?Only if you’re doing it for the right reasons — not ego, not revenge, but alignment. And only if you’re willing to do it differently this time.

Q: How do I know if my new idea is really worth building?Talk to real people. Ask yourself if you’d build it even if it made no money. And test tiny before going big.

Q: How do I avoid burnout this time?Start by honoring your energy, building slower, saying no more often, and checking in with yourself — not just your metrics.

🛠️ Up Next in This Series:

• “How I Validate Startup Ideas Without Writing a Line of Code”

• “What Founder Therapy Taught Me About Product Design”

• “Emotional UX: Designing Apps That Make People Feel Safe, Not Addicted”