I dropped out of high school to start my first small business
Published on September 25, 2025 · Duration 01:22:47
Welcome back, fellow Bootstrap for Cash listeners! In a special anniversary episode that turns the mic on one of our very own, Giorgio Azzinnaro, co-host Iván Peña, with the help of friend Mauro Foresti, dives deep into Giorgio’s wild ride from struggling in the education system to launching his first small business. If you’ve ever felt like the traditional path wasn’t for you, prepare to be inspired – and probably get a good chuckle along the way!
The Early Days: Skipping Grades and Sailing Through Life (Literally)
From the get-go, it was clear Giorgio wasn’t your average kid. He skipped first grade, devoured encyclopedias, and developed a knack for problem-solving. But it’s his passion for sailing that truly defines him. More than just a hobby, sailing taught him the importance of preparation, collaboration, and always being one step ahead, even when “shit hits the fan.” As Mauro humorously points out, Giorgio’s constant pursuit of challenges might just make him a masochist!
The Great Escape: Dropping Out and Finding Freedom in Edinburgh
Feeling uninspired and unchallenged by high school, a 16-year-old Giorgio made a bold move: he dropped out. Armed with a random fact about Scotland’s free education for EU citizens and a fierce desire to learn, he packed his bags for Edinburgh. There, he freelanced to pay rent, landed a software engineering job with no resume (just pure skill!), and even challenged his college curriculum – a true testament to his self-driven spirit. It’s a story of resilience, self-made success, and what it really means to build a business from the ground up, proving that sometimes, the best lessons are learned outside the classroom.
From Medical Software to Market Mishaps: The Entrepreneurial Rollercoaster
Giorgio’s journey into entrepreneurship began with a burning hatred for bad software and a desire to solve real problems. Alongside friends, he built “Skeeter,” an innovative mobile and smartwatch app designed to streamline paperwork for doctors. Despite enthusiastic doctor feedback and a paid trial, the venture faced an uphill battle against hospital bureaucracy and, of course, the uninvited guest: COVID-19. It was a learning curve, revealing the critical importance of sales and the right kind of funding.
Later, another startup, “yeekatee,” taught him a crucial lesson: securing funding doesn’t automatically equal success. The real challenge lies in solving genuine problems, building cool tech for its own sake is not enough.
Bootstrap for Cash: The Present, The Future, and The YouTube Challenge
Now, Giorgio and Iván are navigating the choppy waters of “Bootstrap for Cash” and Sealambda, their indie venture. The name “Bootstrap for Cash” itself is a clever pun, highlighting their self-funded journey, while Sealambda comes from a serendipitous drawing of a “sea lion in the shape of a Lambda.”
The episode also delves into the exhilarating (and often terrifying) reality of bootstrapping a company without a regular salary. Giorgio views this “struggle” not as a burden, but as a crucial constraint that fosters focus and creativity. It’s about operating within limits, proving effectiveness, and then dreaming bigger.
And speaking of challenges, there’s a hilarious on-air bet! Mauro and Iván have dared Giorgio to launch his long-planned YouTube channel by October 7, 2025. Fail, and he owes them an expensive steak dinner in Zurich – hotels included! So, you know what to do, folks, keep an eye on Giorgio’s YouTube!
This episode is a candid, engaging, and genuinely funny look into the mind of an unconventional entrepreneur. Giorgio’s unwavering belief in problem-solving, human connection, and continuous experimentation makes for an incredibly inspiring listen.
Don’t Miss Out!
If you’re interested in stories of resilience, self-made success, and what it really means to build a business from the ground up, this episode is for you. Tune in to hear more about Giorgio’s journey, laugh along with their sardonic humor, and get motivated to tackle your own entrepreneurial challenges. And if you enjoy our content, don’t forget to leave us a review – it really helps us grow and keep bringing you inspiring conversations!
