What My First Failed Startup Taught Me — and How I Finally Got It Right 20 Years Later

Entrepreneur

10-07-2025

Launching a startup two decades after a failed first attempt brought clarity, humility, and a deeper understanding of what it really takes to build a sustainable business.
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They say timing is everything — and that's a lesson I've learned the hard way.
Today, I'm building a startup I truly believe in. But the truth is, this journey didn't start last year. It began more than 20 years ago — with a big idea, the wrong timing and some painful but necessary lessons that would shape everything I'm doing now.
How it started
In 2007, inspired by platforms like Craigslist and LinkedIn, I set out to bring a new kind of online platform to life. I had a strong concept, but not the technical skills to build it alone. So I partnered with a close friend who could fill that gap.
At first, we were excited. But over time, cracks formed — our visions didn't align, our strategies drifted, and financial pressure mounted. Eventually, we had to walk away.
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.
Related: When My Startup Failed, I Was Hopeless and Left in Tears. Here Are the Lessons That Helped Me Restart and Launch Three Successful Companies.
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.
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.
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.
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: U nderstand your industry, track trends, study user behavior and know your competition.
nderstand 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.
Write a business plan. Forecast your finances. Know your funding options. Formalize the business: R egister your company, get your EIN, licenses, permits, and build your legal foundation properly.
egister 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.
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.
Related: 10 Lessons I Learned From Failing My First Acquisition
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.
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