A conversation with Daniel Giacopelli
Ten years ago, I dropped Daniel Giacopelli an e-mail.
I had just begun my entrepreneurial adventure as the co-founder of Sofia Capri, while he was the host of a radio show that I was a huge fan of, ‘The Entrepreneurs’ by Monocle. I thought, why not pitch our sandals brand for the show?
Little did I know then that my e-mail would not just land me on Episode 209. It would also connect me to someone whose work would prove to be instrumental in expanding my vision on all things entrepreneurship — and that is no exaggeration.
A New York native who’s now based in London, Giacopelli originally moved across the pond to pursue a degree in International Relations. He was fascinated by the relationships between nations and their people, and by how their interactions could be shaped to serve the greater good. As fate would have it, however, it was not a diplomatic job listing that he would stumble upon when he graduated. Instead, it was an advert for a position at Monocle’s soon-to-be-launched radio station. Resonating with its international vibe, he applied, and the rest, as they say, is history.
Daniel Giacopelli
He was hired to work on what would become one of Monocle’s most popular shows, ‘The Entrepreneurs’, and quickly became the show’s host, interviewing the founders of newly launched brands that he would discover in all corners of the world. It was something he did for seven years, and did so well because he wasn’t just showcasing startups. He was asking all of the right questions that would give practical answers; tried-and-tested advice that would ring true universally. His conversations would get into the nitty-gritty of the day-to-day, enlightening small business owners globally, no matter if it was a coffee-shop owner in Hong Kong or a swimwear designer in Mallorca. Even if you weren’t a business owner, by the end of each episode, you couldn’t help but come away feeling inspired.
When he became the editor of Courier, he brought this same energy to its pages. By that point, I was no longer a sandals entrepreneur, but I was still leading emerging businesses — a family startup in hospitality and my own. I remember scribbling notes along the sides of its pages and tuning in to its podcast that shared much in common with the spirit of ‘The Entrepreneurs’. Courier was more than just a media brand. It was a goldmine of resourceful information for the budding business owner. Business aside, the stories that Giacopelli chose to spotlight were just incredibly interesting and relevant.
In retrospect, I can see how his early beginnings in the diplomatic sphere helped make him so good at what he does: he asks all of the ight questions — questions that help bring constructive, creative solutions to the table.
Today, he works on editorial and thought leadership projects at Mailchimp and, most interestingly, is the founder of For Starters — a movement dedicated to small business owners that today is a newsletter, but tomorrow…well, just wait and see. I decided to turn the microphone around and ask Giacopelli a few questions to find out more about the person whose words I had been listening to and reading over all these years. Enjoy — and make sure you sign up to his newsletter. I’m certain it will become one of your favourite weekly reads.
When we first met back in 2015, startup culture was a thing, but it was nowhere near as prevalent as it is today. Why do you think startups have become so ubiquitous these days and grown so exponentially?
Startups have been around for decades, but when I started hosting Monocle’s ‘The Entrepreneurs’ podcast back in 2011, it was definitely the dawn of the direct-to-consumer era – when companies like Warby Parker, Bonobos and Glossier were forming and taking off. It was also when the likes of Airbnb and WeWork were gaining popularity. There have been so many ups and downs in the market since then. A lot of startup formation in recent years was driven by so-called ‘easy money’, when VCs were throwing money around like in a casino. But for most founders, those boom times are over (unless you were in crypto a few years ago or in AI right now).
The newsletter I’ve recently launched, For Starters, is targeting a different type of business owner altogether. Rather than being yet another resource for tech startups, it’s focused on a huge and growing group of people I call starters: independent, local, bootstrapped (i.e., self-funded), hands-on business owners. I think we’re about to see a major resurgence of businesses that aren’t trying to raise infinite cash, chase infinite growth and be the next unicorn – they’re trying instead to be something useful, real, profitable and human.
As the world leans further into AI and as traditional coding jobs become extinct, the only real differentiator or ‘moat’ left for businesses will be either 1) building an actual community and/or 2) creating things you can touch and feel. That’s the one thing AI can’t replicate and probably/hopefully never will.
The startup world is about to change in a big way. It’s exciting because new models are emerging. It’s terrifying because the old playbook doesn’t work anymore. But if I were a betting guy, I wouldn’t put my money on tech startups – I’d bet it all on starters.
Which books are sitting on your bedside table right now?
There’s a Japanese concept called tsundoku, which is the phenomenon of acquiring books and letting them pile up. I’m guilty of this. Some books that are half-read or waiting to be read are:
When We Cease to Understand the World, by Benjamín Labatut
Voices of the Fallen Heroes: And Other Stories, by Yukio Mishima
Company of One, by Paul Jarvis
Various recently bought secondhand photobooks
And about 400 back issues of The New Yorker.
You've interviewed and met hundreds of small business owners over the years —what is the most common answer you've heard to the question, “Looking back, what is the one thing you wish you'd known before starting out?"
“How hard it would be.”
If you could invite 3 different start-up owners to sit around a table for dinner one evening, who would they be and why?
My wife, my dad, and whoever the opposite of Elon Musk is.
Is there anything you really wish to share with us — be it a reflection, a thought, a question, or just what is inspiring you right now?
I honestly believe that our world is about to go, for lack of a better word, bananas. Up will be down, and down will be up. Gen AI will wipe out entire professions and transform industries. No one knows what will happen when AGI is reached. The growth of populism, nationalism and protectionism will continue to be hugely destabilising. The quantum apocalypse is coming (just Google “Q-Day”). And, of course, there’s global warming, the mother of all problems. I really don’t want to be alarmist, but the prognosis of all this stuff isn’t… great. [Editor’s note: and he wrote this before the latest tariff chaos!].
And yet. There are still things in our control. There’s a lot you can do, right now, to help prevent some of the worst outcomes. As one of my friends recently told me, There’s a time for complaining and a time for building. So, start building. Build a sustainable business. Build something for your local community. Don’t add to the slop and noise and disinformation and brain rot. Find a way to use business for good. Be a good neighbour. Be a good person. If everyone did this, or just more of us did it, we’d be alright. And then I could finally take that nuclear bunker in New Zealand out of my Amazon shopping cart…