Profile of a Serial Entrepreneur- Marco Ottolini

We recently sat down with Marco Ottolini, a serial entrepreneur whose latest project, Styloola, is currently crowdfunding on CrowdBnk. Styloola aims to become a leading data company for fashion retailers, creating  comprehensive profiles of fashion enthusiasts interested in shopping and supporting them in innovative ways while they shop in brick and mortar and e-commerce sites. Marco's ample experience with entrepreneurship and crowdfunding made for a deeply interesting conversation.

Tell us a bit about your background as a serial entrepreneur.

I founded Italia Online in 1994. It was among the first Internet service providers in Italy and over the years become one of the most successful – and has survived until now.

I then founded Moda Online and Travel Online. Moda Online published pictures from the Milano fashion week in February '96, making it one of the first fashion websites. Travel Online started as a web magazine for travellers. It included TripAdvisor-like features. The site received a Series A of €2.6M in 1999 and was later sold to two publishers in Italy. It is now part of eDreams.

After selling the company, I worked at the Italian startup ZDNet and, in 2004, took a break to start my own family (now I'm a proud father of two). I re-entered the workforce through project work and in 2011, I started working on a project that later become the heart of Styloola, my current startup. Styloola was founded in October 2012 after a successful crowdfunding round in Italy through a platform called SiamoSoci. We’re now raising another round through CrowdBnk.

What have been some of the most pivotal moments in your career?

One of the most important was the first time my co-founders and I received investment (€2.5M) for Italia Online in 1999. Discovering that our idea was worth millions was an amazing feeling. It gave us the confidence and energy to grow.

Another important moment for me was in 1990, when I was appointed as Editor in Chief of PC Magazine in Italy. That gave me the opportunity to connect with the most influential people of the decade (Bill Gates, Larry Ellison, Steve Ballmer, Ray Ozzie and many others). It forged my entrepreneurial spirit and gave me a privileged view into the digital revolution that was taking place.

You've managed to crowdfund a number of times. How have you found the crowdfunding process?

It's much more difficult in the setup phase, compared to other methods of financing, because you have to prepare a lot of documentation. It needs to be perfect. But after that, the crowdfunding process is smoother because you have the opportunity to reach a larger audience. You present your idea to people who are genuinely interested and able to understand your real value proposition. So, it's definitely more efficient and faster than a "normal" venture capital round.

What advice could you give to entrepreneurs who want to crowdfund?

Be bold and never lie. Try to really explain your vision and don't spend too much time on details in the business plan that only venture capitalists are able to understand (like churn). Investors who come from crowdfunding are betting on you - the amount each individual invests is not as big as a venture capital firm, so they can decide faster than VCs, but only if they’re "inspired". They’re also willing to take a chance on the team, rather than focusing only on raw numbers, since they know these are forecasts.

What's next for you and Styloola?

We recently introduced the Styloola Box, a hardware device that is installed in retail stores. It allows retailers to measure footfall, profile customers and target them while they shop. This will radically change the way they approach customers. It has also opened up new possibilities for us. We are creating a new brand (FreeWi) to specifically address the retail sector and are building up a dedicated sales team to achieve our business goal. I would say that after a long development cycle, it's now time for Styloola to grow!