It took me 3 years. I quit 4 times. I bootstrapped everything. Finally, I saved enough to hire a team earlier this year. And just this weekend our app entered the app store.

The Dream

Three years ago, I had a vision — a vision to create an app that would help fix our broken information ecosystem. I was sick of the junk Social media (including Reddit) and mainstream media was feeding me.

The idea was brilliant, at least in my head. But as many of you know, the journey from a dream to reality is often fraught with challenges.

I’m proud to have finally released the app this week. It’s missing a ton, but damn it feels good.

Check it out at cicero.ly

Financial Constraints

Bootstrapping a startup is like sailing a ship through a storm with limited supplies. You’re the captain, the crew, and the repairman, all rolled into one. I had to save every penny, cut corners where I could, and even took up freelance gigs to fund my startup. There were times when I had to choose between paying for server costs or groceries. I chose the former, surviving on ramen and sheer willpower.

Lesson 1: Prioritize Your Resources

When bootstrapping, every dollar counts. Make a budget and stick to it. Identify what’s essential for your startup’s growth and allocate resources accordingly.

Emotional Toll

I quit four times. Yes, you read that right. Four times I threw in the towel, convinced that Cicero was a pipe dream. The emotional toll was unbearable. The stress, the isolation, and the constant fear of failure weighed heavily on me.

Lesson 2: Take Care of Your Mental Health

Entrepreneurship is a marathon, not a sprint. It’s crucial to take breaks, seek emotional support, and perhaps most importantly, know when to step back and reassess.

Skill Gaps

I’m not a coder. My expertise lies in marketing and product development. The technical challenges seemed insurmountable. I had to learn enough to be dangerous, to understand what was feasible and what wasn’t.

Lesson 3: Be a Jack of All Trades, Master of Some

In a startup, especially when you’re bootstrapping, you can’t afford to be just a specialist. You need a broad skill set to navigate through various challenges. However, know where your strengths lie and capitalize on them.

The Turning Point

Earlier this year, after scrimping and saving, I finally had enough to hire a small but talented team. It was a game-changer. The burden was no longer solely on my shoulders. We were a unit, working in tandem towards a common goal.

Lesson 4: Teamwork Makes the Dream Work

The right team can make or break your startup. Choose people who complement your skills and share your vision.

The Milestone

Just this weekend, Cicero made its debut on the app store. The feeling was surreal. Three years of blood, sweat, and tears had culminated in this moment. But this is just the beginning.

Lesson 5: Celebrate the Small Wins but Keep Your Eye on the Prize

Every milestone, no matter how small, is a step towards your ultimate goal. Celebrate them, but don’t lose sight of the bigger picture.

Final Thoughts

Creating Cicero was an odyssey, a rollercoaster of highs and lows. But every struggle, every setback, was a lesson in disguise. To all aspiring entrepreneurs out there, remember this: the road to success is paved with failures. Embrace them, learn from them, and most importantly, never give up.

Here’s to the next chapter of Cicero. Cheers

P.S. I made a more practical guide that I posted here two years ago while working on my startup: https://www.reddit.com/r/Entrepreneur/comments/q7by8n/the_ultimate_no_bs_guide_for_startups_with_dozens/