/ / What A Year In Tuscany Taught Me As An American Entrepreneur
/ / What A Year In Tuscany Taught Me As An American Entrepreneur

What A Year In Tuscany Taught Me As An American Entrepreneur

By Steve MacDonald

It’s not exactly been like Rip Van Winkle, but for an American entrepreneur and investor who spent much of the past year in a 500-year-old villa overlooking Florence, Italy, man, what a difference that year has made for me. 

When my family and I left Tampa for Tuscany last August, the big conversations in tech focused on Web3, the Metaverse, and related cryptocurrency and blockchain opportunities. How were we going to build (and invest in) the next generation of Internet technologies over the next several years? Fast forward to now, and Web3 is, well, something we’ll get around to one of these days. 

The real heat, which has completely replaced Web3 and the Metaverse conversations, is in artificial intelligence applications and companies, especially generative AI uses such as we’re seeing with ChatGPT, Midjourney, Stable Diffusion, Firefly, Bard, and hundreds of emerging and established companies. The conversation has changed dramatically. 

It’s a big shift in a relatively short time, but it’s also good news for me. One of our family goals in moving to Florence was to change things up, taking a timeout from the crazy pace of everyday life that we had known while building two startups into successful exits, making dozens of investments, pursuing a wide range of life adventures, and not incidentally, raising a great kid. 

The plan worked. This past year was an opportune time to step back and watch from afar, perched in a very different business climate and mindset, as U.S. markets plummeted and rebounded, entire sectors reset, and expectations changed dramatically. 

The distance from Florence, weirdly, gave me more, or at least a different, clarity than I would have had living in the middle of things in the United States. Now, I’m excited to bring this new perspective to my investing and business decisions going forward. 

So what do I expect will change as I jump back in? I plan to identify a new set of phenomenal founders and companies that are maximizing the opportunities out there in several sectors, then focusing on them more intensely and intentionally. 

The big vision is to create a mini version of Berkshire Hathaway, investing and closely supporting a portfolio of smart companies for the long haul. I’ve already embraced one such company, Kush, which focuses on B2B distribution of cannabis and CBD products

In looking at other possible portfolio companies, I plan to take a longer view of what deals I join, and why. A more considered approach is way overdue as we try to figure out the winners of a fast-evolving economy. 

To be fair, after the pandemic pulled back and the economy reopened with a roar, it was difficult to do that in 2021 and early 2022. 

Take too long to vet a deal and you might get shut out completely. People were just writing checks, seemingly without asking a lot of questions, so they wouldn’t miss out on a potentially big opportunity. The logic of the moment may have made sense, but it inevitably led to some bad investments, and bad company-building practices. 

That said, I’m also excited that the rise of new, cheap, and powerful online tools are changing what entrepreneurs need to get a company up and running. With these technologies, it’s back to two people in a garage, able to leverage a compelling idea into reality with just a few hundred thousand dollars of investment. 

That’s a big change from just a couple of years ago, where the investment conversation seemingly was always about raising as many tens of millions of dollars as possible, to puff up a valuation, scare off competitors, and perhaps get a leg up in partnerships and market share. Just to get started might cost $5 million to $10 million. 

Now, that approach seems heavy handed and unnecessary. In fact, if a startup’s team says they need $10 million to launch, these days I’m thinking they may not be the right team to back.  

Will I miss some things from Italy itself? Of course. The amazing food, alongside beautiful Brunello di Montalcino red wines, is truly special, especially looking out over Florence. My son not only picked up a new language, and an appreciation for the Italian style of soccer, but also a newfound love of mathematics. 

And living in a 2,000-year-old city gives you another kind of perspective, of long time. Our villa was built in the 15th Century by a nephew of the greatest Medici of all, Lorenzo the Magnificent. I’ll miss my neighbor Henry the Hermit, a holy Bishop who’s skeletal remains that were displayed and enshrined in the altar of a 1,000-year-old chapel abutting our Villa.  The timelines are a little crazy to ponder, but they push you to think bigger and more long-term about your life and what you’re doing with it. 

Italy certainly also has some things I won’t miss, from ridiculous bureaucracies to the notoriously crazy drivers (and motorbike riders) to mosquitos whose bite can raise a nasty welt. And the entrepreneurial climate for startups is terrible, and difficult to fix. 

So I look forward to returning to Tampa, and restarting the life I knew with new perspectives and a different cadence of life. I can’t wait to dive back into startup-focused organizations such as Florida Funders and the Tampa Bay Wave accelerator. But most importantly, I’m thankful that I could take a year with my family to have an extraordinary set of experiences, reset my life and life patterns, and return to the fray with new perspectives. I can’t wait to see what comes next.