Falling Short, But Never Stopping—What I Learned from My Startup and a Billion-Dollar Founder
Two years. That’s how long I poured everything into my startup, trying to make it work as a bootstrapped endeavor. And now, looking back, I can admit it—I fell short.
Not because the idea lacked value. Not because I wasn’t willing to put in the work. But because I tried to do it alone for too long. I wanted to prove I could bootstrap my way to success, but in hindsight, I see that I should have engaged the right networks, found aligned people and capital sooner, and built the foundation with the right support instead of before it.
Ironically, those people were out there all along—I just found them a little too late.
The Reality of 2024 & 2025—And Why There’s No Shame in Starting Over
I know I’m not alone in this. The private and public sector cutbacks in 2024 and now 2025 have forced many talented people to reset. Some of us are seeing opportunities vanish overnight. Some of us are back to the drawing board, questioning if all the effort was worth it.
If you’re in that place—let me tell you: there is no shame in taking a job below your experience level if that’s what it takes to keep hope alive.
I’ve done it before. I’ve worked minimum-wage jobs in tough times, and if I have to, I’ll do it again. I don’t see it as failure—I see it as endurance.
And endurance teaches you things.
What I Gained From Falling Short
The past two years didn’t give me a billion-dollar exit—but they gave me empathy, experience, and a sharper skill set than ever before.
The cover letters, executive summaries, pitch decks, MVPs, and resumes I create today? They exceed the quality of anything I’ve ever received from paid professionals, recruiters, or agencies. The way I position myself for opportunities now? Stronger than ever. That doesn’t guarantee I’ll land my next role today, but it means I’ve never been more prepared.
And through all of this, I remain grateful. Not because I ignore the difficulty—but because I’ve learned to take both success and failure in stride. I’m not a Buddhist, but I might as well be one without the label. Or maybe I’m more of an übermenschian—choosing to face reality as it is, not as I wish it to be, and being grateful for another day to play one more time.
What a Billion-Dollar Founder Taught Me About Pushing Through
I am reminded of Jamie Kern Lima, founder of IT Cosmetics.
She maxed out credit cards, pitched investors for years, and faced constant rejection. She was told she wasn’t the right fit for the beauty industry. Retailers dismissed her. QVC rejected her multiple times.
Then, when she finally got a chance to sell on QVC, she made a bold move—she went on live TV and demonstrated her makeup on her own rosacea-prone skin, instead of using models with perfect skin. It sold out in minutes.
In 2016, L'Oréal acquired IT Cosmetics for $1.2 billion.
I Came Close. And Next Time, I’m Getting There.
Like Jamie, I took the bootstrap path—betting on myself. This time, it didn’t hit. But I got the lessons that will make the next time different.
So, where does that leave me?
I am open to opportunities—but I refuse to beg. Not because of pride, but because begging disrupts the natural flow of life. Instead, I will work, rebuild, and refine my vision for a better tomorrow.
And the next time?
I won’t just come close—I’ll get there.