7 Lessons from My First 3 Years Running a Startup

There’s never a perfect time to start a company. But three years into building Reboxed, I’ve learned that the lessons that matter most aren’t in the pitch decks or spreadsheets — they’re the ones you earn the hard way.

Here are seven that might help you in your own journey.

1. Find a problem you’d fight for

Startups are too hard to fake. If you don’t care deeply about the problem, you’ll quit when things get messy. For me, it was e-waste — the fastest-growing waste stream on the planet. Once I connected my personal mission to my work, everything clicked.

📖 Related read: Start with Why — Simon Sinek
💭 Takeaway: If you wouldn’t fight for it when it’s hard, it’s not the right problem.

2. Surround yourself with people smarter than you

Your network really is your net worth. Reboxed wouldn’t exist without mentors who knew the industry inside out. One cold LinkedIn message led us to Pete Petrondas (ex-Envirophone) — he became our first mentor, then our lead investor.

📖 Related read: Tribes — Seth Godin
💭 Takeaway: Collaboration > competition. Ask for help earlier than you think.

3. Build your story in chapters

Amazon started as a bookstore. Every giant began small. Break your story into phases — Chapter A (now), Chapter B (3–5 years), Chapter C (the big vision). Investors and partners buy into a story they can believe in today, not just in some distant future.

📖 Related read: Crossing the Chasm — Geoffrey Moore
💭 Takeaway: Simplicity is genius. If a child can’t understand your story, it’s too complex.

4. Pitching is selling — and rejection is the price of admission

In three years, I’ve raised millions — and been told “no” hundreds of times. Every “no” gave me sharper edges. A pitch deck is never finished; it evolves with you.

📖 Related read: The Mom Test — Rob Fitzpatrick
💭 Takeaway: Don’t take rejection personally. Take it as data.

5. Burnout is real — resilience beats hustle

54% of founders report burnout. I’ve been there. Hustle can take you far, but resilience keeps you in the game. Protect your mornings, set boundaries, and make space to recover.

📖 Related read: The Messy Middle — Scott Belsky
💭 Takeaway: Play the long game. Energy is your most important asset.

6. Legals, ops, and finance matter more than you think

You can’t scale a mountain without a sherpa. Early on, SeedLegals helped us navigate contracts, cap tables, and term sheets. It’s not glamorous, but if your foundations aren’t solid, the house will fall.

💭 Takeaway: Get the boring stuff right early. It buys you freedom later.

7. Your network is your multiplier

Some investors took 12 months to back us. Others joined after one coffee. Either way, it was our relationships that got Reboxed off the ground. Investors don’t just bring money; they bring introductions, doors, and energy.

📖 Related read: Give and Take — Adam Grant
💭 Takeaway: Choose investors like teammates, not just cheque-writers.

Final Thought

Three years in, I’ve learned this: success isn’t about avoiding mistakes, it’s about surviving them. Every founder’s playbook is written in sweat, setbacks, and small wins.

As Theodore Roosevelt said back in 1910:

“The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood… who strives valiantly.”

If you’re building something that matters — welcome to the arena.