What My First Failed Startup Taught Me — and How I Finally Got It Right 20 Years Later
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Opinions expressed by Entrepreneur contributors are their own.

They say timing is everything — and that’s a lesson I’ve learned the hard way.

Today, I’m creating a startup I wholeheartedly believe in. However, the reality is that this journey didn’t just start last year. It began over 20 years ago with a significant idea, unfortunate timing, and some hard but necessary lessons that have shaped everything I’m doing today.

How it started

In 2007, motivated by platforms like Craigslist and LinkedIn, I aimed to launch a new type of online platform. I had a solid idea but lacked the technical expertise to execute it independently. Therefore, I teamed up with a close friend who could provide that expertise.

Initially, we were enthusiastic. However, as time passed, issues arose — our visions didn’t align, our strategies diverged, and financial strain increased. Ultimately, we had to part ways.

It was disappointing, even devastating. But I never stopped believing in the core idea. Instead, I paused to reflect on what went wrong, what I’d learned, and what I needed to do differently next time.

That reflection helped shape both who I am and how I operate today.

What I learned (the first time around)

  • Learning never stops: Your best insights often come from others. Lean into your network — mentors, peers, even critics. Learning from others and sharing your own experience creates a powerful loop of growth.
  • Be willing to adapt: Even with a great idea, you have to stay flexible. Whether you’re launching or scaling, being able to pivot when needed isn’t a weakness — it’s a survival skill.

Getting it right the second time

  • Start with clarity: A shared vision is critical. Before launching, make sure you and your co-founder(s) are aligned on goals, roles, and long-term expectations. Misalignment early on will cost you later.
  • Be honest with yourself and your team: Ask the hard questions up front: Why are we doing this? What problem are we solving? Who are we solving it for? If your answers don’t match, it’s time to regroup.
  • Culture matters as much as code: Yes, you need technical talent. But you also need people who share your values, collaborate well, and grow with the company. Don’t underestimate cultural fit — it makes or breaks teams.

If you build it, will they come?

This time around, I approached things differently. I didn’t just assume the idea was good — I tested it. I asked:

Are we solving a real problem?

Does the market need this now?

What’s our unique value proposition (UVP)?

Why would anyone choose us?

Customer-first thinking became the foundation. Instead of building what we thought was valuable, we built what the market actually needed — and made sure our solution stayed relevant.

Getting tactical: what every founder needs to consider

  • Do your homework: Understand your industry, track trends, study user behavior and know your competition.
  • Create a strategy: Write a business plan. Forecast your finances. Know your funding options.
  • Formalize the business: Register your company, get your EIN, licenses, permits, and build your legal foundation properly.
  • Build the right team: Use your network to find people who align with your mission and culture.
  • Sell the vision: Know your customer, refine your message and create a product or service they actually want.

Final thoughts

Be both sales-driven and market-aware. Know your audience — where they get information, what problems they face, what resonates with them. Your customer acquisition strategy should be informed by real data, not just instinct.

And most importantly, keep an open mind. Inspiration can come from anywhere — a conversation, a failure, a new connection. The more you listen, the more likely you are to spot those game-changing ideas.

Building something meaningful takes time. For me, it took over 20 years. But every setback, misstep and restart has made this journey — and this version of the startup — infinitely more grounded and more real.

Ready to break through your revenue ceiling? Join us at Level Up, a conference for ambitious business leaders to unlock new growth opportunities.

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