Online Entrepreneurship: What Gennaro Cuofano learnt from his Failures and Success Online

First of all, thank you for having me. It’s really a pleasure to share a bit of my story, because we’re going to talk about the blog and the research I do on business modeling and business strategy, but I usually don’t get the chance to tell my own story. So I’m glad there’s an opportunity. I come from a very small town in Southern Italy—maybe around 5,000 people. It’s in the Campania region, where the Amalfi Coast and Naples are, and we have many beautiful things there. In terms of professional opportunities, I moved to Rome when I was 19, so I spent my entire teenage life in Southern Italy. My name actually tells the story for people from Italy—my name is typical of Southern Italy. There are hardly any people outside that region with my name, so if you’re Italian, you know where I’m coming from.

Yeah, yeah, absolutely. It’s the Campania region. It’s Naples. Pretty much all the Naples area, you know, it’s one of the most common names. But outside, there is not much, unless you go like to New York, where we have many Italian American people were probably you’re going to find this name, otherwise they are. Actually was fun because a few, few weeks ago, I was interviewing the vice president of blockchain at IBM, and the funny thing is, now he’s a an American, Italian, but he changed his name like names like Jerry, but in reality, his real name is like general, so it’s my same name. This was the first time that found like someone American who has my, my same name, so it was interesting.

Pretty much, I grew up in these small towns from the time I was about 18. There are many interesting things about where I come from—lots of beautiful places—but I’m very passionate about history. One interesting thing is, before the Romans, there were the Etruscans, who laid the foundation for the Roman Empire. One of their most important settlements was in my region, and it was also an important settlement during Roman times. Since I love history, that’s really fascinating to me.

Then, of course, on a daily basis, there are a lot of interesting people. If you go to Southern Italy, we’re usually quite different from Northern Italy. It depends on how you look at it, but we’re generally seen as friendlier, more open, and so on. Sometimes stereotypes get it right. It’s a really interesting place.

Well, honestly, I lived a pretty regular life—nothing crazy about me or my family. Probably the most interesting thing is that I never expected to work in the digital marketing space. For instance, when I lived in San Diego, I had no idea about this world. I really got into it after I left California. It’s funny because you’d think you’d get familiar with digital marketing in California, but for me it happened afterward. So maybe the most interesting thing is that, professionally, I’ve led a lot of different lives. But no, I can’t say I was a stripper or went to jail or anything like that.

I’m back in Italy. I first moved to Rome when I was 18, then I moved to the US when I was about 24, and then I moved back to Italy—Rome—around 28 or 29. I love this place. I’m pretty passionate about history; there’s history everywhere here. I think it’s a beautiful place, especially if you’re running a digital business, because you can work with people from all over the world. It’s great—many people really want to come here. If I say, “I might do an event—would you come?” they’ll say, “Yes, of course. I’d definitely come.”

I’ll try to keep this relatively short, though there are a lot of pieces to it. Before I started law school, I actually wanted to become a doctor, mostly because my mother was a doctor. In Italy, there’s still a strong emphasis on professions like being a lawyer or a doctor. But I couldn’t get into med school, so I ended up in law. Even then, I already knew I didn’t want to be a lawyer—I just liked the mindset you get from law, constantly thinking about objections, which helps in sales and other fields. But the profession itself wasn’t my passion.

At the same time, I got fascinated by finance and investing. I liked the idea of being independent, so I started investing a bit on my own, studying the stock market and economics. Right after law school, I pivoted into finance. I got an internship in Washington, D.C., came back to Italy, then did an apprenticeship and enrolled in an MBA program in Rome. I finished that MBA in San Diego, where I landed a role with a commercial real estate company, working in analysis and finance.

While I was growing that career, it still didn’t feel right. I wanted freedom, but ended up working more than ever for someone else. I realized I needed another change, so I quit my job in the US and returned to Italy, where I got into digital marketing. That’s when the Four-Week MBA concept took shape. The idea first came to me back in business school, when I realized many academic models and theories didn’t fully apply to the real world. I thought, “What if I could build the business school I wish I had?” So I started documenting my learning journey, building Four-Week MBA initially for myself.

Around 2015 and 2016, getting a digital business off the ground was tougher than I expected. After a year, I made a little money but not enough to go full-time. I realized I was missing the marketing and sales piece. Coming from a law and finance background, I used to dismiss salespeople, and I had to change that mindset. If you can’t bring in customers, you can’t survive as a business.

That was when I joined WordLift, an AI-for-SEO startup, in a business development role. I learned how crucial it is to understand a client’s business model, because that’s how you sell on a deeper level. I got passionate about business model innovation and strategy, and I poured all that into the Four-Week MBA blog, focusing on real-life application.

Early on, I tried third-party platforms (Udemy, Amazon) to distribute my content. I got good numbers—lots of students and books sold—but my brand got diluted there. By 2017 and early 2018, I shifted focus to my own site. A key moment was when I wrote a post on DuckDuckGo that went viral—100,000 hits in a couple of days. That convinced me to double down on my blog.

From then on, I focused heavily on strategy and business model innovation. It’s basically my real-life “PhD.” Instead of going back to school, I do my own research and document everything on the Four-Week MBA. It’s a work in progress, but that’s the essence of how I went from law school to finance, then to digital marketing, and ended up in the entrepreneurial space I’m in now.

Yeah, absolutely. I think for me there was an important realization after a few years in the digital marketing space. When I started back in 2015, I didn’t know anything about it. Coming from a different industry, I thought, “Okay, if I want to start a digital business, what do I do?” My initial, most logical conclusion—which I realized after a few years wasn’t correct—was: “I’ll just develop content, then push it to a third-party platform like Amazon or Udemy.” So I used those platforms as the main distributors of my content. But I wasn’t really curating my own distribution, and it took me two years to understand that wasn’t the right approach.

You can call my blog a startup or a company I’m trying to bootstrap. I talk to many startups, and often they’ll say, “I’m not going to use that channel—like SEO—because right now I need to get customers quickly. I’m going to start doing paid acquisition,” and so on. That’s fast, but if you don’t build your own brand identity—which means building a real customer base—you can’t grow sustainably.

So, looking back at 2015 to around 2017, I’d call those years a huge failure for me in digital marketing. It was almost three years of one failure after another. I still fail a lot—I’m not saying everything works perfectly now. But at the time, the biggest issues were: (1) I wasn’t relying on my own distribution, and (2) my pricing was messed up because I didn’t control it. Ultimately, I needed more control over my own business.

In the second phase, around 2018, I said, “Okay, this is the topic I want to pursue, and I want my blog to have high authority in this niche. How do I do that?” I decided to treat it like I was studying for a PhD—document everything I’m doing, put out all this content on the blog, and keep it free. I pushed as much as possible because I was starting from zero, and I knew if I tried to compete with big brands while also heavily monetizing, it wouldn’t work early on.

That’s not the only strategy, of course. In marketing, you might be more effective writing for big publications like Forbes or Business Insider to quickly gain authority. But I’d tried that before, and I decided, “Instead of pitching those publications, I’ll publish original research on my own site so I’m the primary source.”

From an SEO standpoint, if you look at major players like Investopedia or Business Insider, they’re massive compared to me. I asked myself, “How can I provide value that they can’t?” My answer: go really deep on research and content development. Because they’re so large, they can’t sink that much time into individual articles or else they’d go bankrupt. I can afford to spend weeks on a single piece of content if I need to. It’s not scalable, but it makes me unique, and it’s something I’m passionate about.

That’s basically the realization that got me here. So, starting around 2018, I’ve been pushing and pushing; that’s how the blog began gaining traction. Right now, I’m trying to share more of my story so people understand how I arrived at this point, while also doubling down on the same approach. It’s not the most scalable, and I don’t have unlimited time, but I’m essentially working two jobs to provide as much value as I can. That’s the process in a nutshell.

Again, I went back to the job market to develop the skills I was missing, especially in sales and marketing. From around 2016 or 2017 up to 2018, I was mostly focused on business development at this startup, and I kind of left my blog on the side. I worked on it, but since I didn’t see it taking off, I felt it was probably a waste of time—I was just using it to sell the educational materials I had.

Then I realized that if I didn’t start pushing harder on this, I couldn’t really call it a true experiment. One thing that happens a lot in the startup world is that we say we “experiment” and “test a lot of things,” and sure, there are cheap tests you can run to see if they work, then double down on what does. But there are also things you want to succeed no matter what, and you can’t really call those “experiments”—they’re things you’re determined to do, even if they fail multiple times. You just keep pushing until they work, and I think that’s what entrepreneurship is really about.

It’s important to have models and frameworks so you can test things cheaply and quickly at a tactical level, while also setting boundaries and saying, “Even if this doesn’t work the first or second or third time, I’m still going to push.” Very few projects take off right away. If we look at exceptions like Google, yeah, it gained traction quickly as a tool, but even Google took a few years to figure out a scalable, viable business model.

So even cases that look like overnight successes still involve a lot of failures in the background. It can be painful—I wish failure were less painful, but it usually isn’t. That’s why you need a long-term vision and also a short-term framework for experimentation. You can move fast tactically, but you keep your big-picture vision steady. If you don’t truly want to build a certain part of your business, just leave it alone, because if you’re not committed, it’s not going to work.

Right, there’s a strategy I like to use that really suits me well. I try to adopt an approach where I look at two opposite things. On one side, I use SEO a lot for understanding where the interest is—so I adapt content based on volume and demand. But on the other side, if I feel something is very interesting, it doesn’t matter if there’s search volume or not; I’ll publish it because I believe it’s valuable. Maybe right now there’s no volume at all, but there are topics I know I need to cover because it feels right. I might not see a return for one or two years—maybe even three—but I’ll still push out that content, so when the market eventually picks up on those topics, I’m already positioned for it.

For example, when I wrote about DuckDuckGo back in 2016 or 2017, the company had existed since around 2009, but it wasn’t that popular yet—at least not in mainstream circles. I was just excited about it and covered it without any clear strategy, and it gained some traction initially. Later, when people became more interested in privacy, it picked up even more.

So I basically use two approaches: one, yes, rely on SEO as an incredible source of data for what to produce, because it can give you an ROI. But two, don’t rely on data exclusively. If you think a topic might blow up in a few years, cover it even if there’s currently no demand. If you go too heavily on SEO alone, you risk becoming a commodity in terms of content. That’s how I like to balance those two things when developing new material.

I honestly love Google. I think it’s fascinating to break down everything they do because it’s one of the most interesting companies out there. Of course, when I covered Google’s business model, some people said, “This will never apply to my company.” But the point isn’t whether it applies to your specific company; it’s about understanding the logic of a platform that controls your distribution. Right now, Google and Amazon are gatekeepers connecting you to your customers. If you don’t grasp their underlying business logic, it’s tough to build a better small business.

That’s the main reason I’m obsessed with huge companies like Google and Amazon—but from a certain perspective. I’m not trying to tell you how to be like Jeff Bezos or Steve Jobs. I’m showing you the business logic behind these companies so you can “surf the wave” and gain traction. Otherwise, you’ll struggle just like I did when I started my digital business.

I use Google a lot, partly because it lets me see how the company’s algorithms and updates evolve over time. The more you observe the search results, the more you understand how they’re changing. On the other hand, I also use DuckDuckGo to step out of the filter bubble, especially if I’m digging deeper into research. Of course, Google is still far more advanced in terms of search results. I think people use DuckDuckGo mainly for privacy, but they also like identifying with something different from what most people use. It’s a bit of a statement—“We’re not the status quo; we’re not mainstream.”

Some people, especially technical folks like engineers, say they use DuckDuckGo purely for privacy. Yes, that’s part of it, but I also think they enjoy feeling different from the masses. We all want to feel unique. Another thing is that DuckDuckGo can sometimes produce results that vary a lot from Google, so you find information you might otherwise miss. If I’m doing certain kinds of research, I’ll use DuckDuckGo. Otherwise, my default is usually Google because it helps me study the platform itself—seeing how it’s shifting and experimenting in real time.

For example, a few weeks ago, Google tested “deduplication,” where they removed the standard organic result if you were already in the featured snippet (the answer box at the top of results). I noticed it happening live and mentioned it to some people at Google, pointing out that on desktop, it didn’t make sense—there was a snippet that looked like a knowledge panel on the left side of the page, and it just took away traffic. People on desktop aren’t the same as on mobile, yet Google treated them the same. They heard that feedback from the community and ended up rolling back that feature snippet variation. It was interesting to see it play out in real time and realize you could contribute to the conversation when Google’s experiments didn’t quite work.

Yeah, absolutely. I’m a real-case scenario for that. The main issue on Amazon is that they also take a good fraction of your sales, and it’s not like you automatically get visibility. You have to understand something like “Amazon SEO”—there are many people working on that. If you really want better placement and visibility, you need to study how Amazon’s algorithm works.

So my point is, either Amazon isn’t your main distribution channel, or you have the ability to negotiate your terms with them—your pricing, your distribution, and so on. That might be possible if, for example, you’re really influential. Then you can say, “Amazon, I’ll give you my book, but only if you let me set my own pricing and allow certain types of distribution.” That’s how big publishers often do it, because they have the negotiating power.

Otherwise, if you rely on Amazon as your main channel, you’d better understand that either you publish a lot of material—so you’re aligning with Amazon’s mission of showing variety and convenience—or you become really good at Amazon SEO. Or you accept that you might not get much out of it. I’m not a fan of those scenarios.

My suggestion is either go with an established publisher—though that might involve a lengthy pitch process—or go back and build your personal brand if you’re trying to do a personal-brand-based business. Maybe you use influencer marketing, or like I did, you invest in creating content and become an authority in your space. It takes time, but it strengthens your negotiating position so you can eventually go to Amazon and say, “I’ll publish this book with you, but only under these conditions.” Unless you have that power, you’re just another person on a third-party platform whose content could be commoditized.

Yes, there are exceptions: you can become a bestseller on Amazon, and some people have done that. But I’d say that’s more of an exception than the rule—probably less than 0.1% of people who try it.

Well, really, the best place is just to go on the blog—FourWeekMBA.com. That’s where you’ll find all the research I’ve done over the years. And of course, you can subscribe to the newsletter, because I try to push out a lot of content. I’m very prolific, so people may complain that I send out too many newsletters, but the problem is I have a lot of stuff that I want to share. I can’t stop myself from doing that. So I’ll push it out or try to pace myself so I’m more strategic in some ways. But then I also want to share all the things I’m starting and doing. So really, before anything else, just go on the blog and you can find all the information you need.

Thank you very much. I appreciate it. It was fun. Thank you.