We just got ripped off in Milano, and sitting on the train at the moment, I feel shitty about it.

We should have seen this coming but, 48 hours in the city, what could go wrong?

It started as soon as we we walked out of the train station on day 1. A random guy running after us looking for a few Euros for a phone call after telling us some elaborate story on how his fanny pack got stolen.

First off, who the hell still wears a fanny pack? We should have known then.

Our Airbnb, which we had booked only a few days beforehand was about an hour walk away, so we decided to walk.

In retrospect, that walk was one of the best experiences we had in the city. Besides the cigarettes and diesel (ugh, a common theme in big city Italy), the walk was nice. We passed old churches, parts of the old Roman wall, and some beautiful gardens and parks.

We met our Airbnb host outside the building and quickly started walking up the stairs.

To our surprise, the first floor was really the second, and we were on the 5th. But after hiking the Alps a few days before, we new our legs could handle it.

The apartment was small, and freshly renovated. Ikea products furnished it, and we were told that we’d be the first guests they welcomed in this rental.

I had a sense of relief as well as slightly being alarmed, especially when 20 minutes after I got a text asking if we were home. They needed to drop off more appliances and pots.

I wondered if the apartment was actually ready to be lived in.

After a quick lunch across the street, we went back to the apartment so Melissa can take a quick shower and get ready for the night’s activities.

I was hosting a mentoring / Q&A session at Bocconi University for their entrepreneurship club and I needed some time to get my head straight.  

This is when we found out that we had no hot water. A few calls to our host, it seemed like the hot water heater was not turned on.

Let me paint the picture of the bathroom for you so you can understand what we were dealing with:

A sink, toilet, bidet, water heater, and shower — all within a 5×5 space. No tub, no real shower, just a shower head and a drain, directly next to the toilet.

**Deep Breath** It’s charming, right?

Okay, time for my first session.

We didn’t know what to expect walking in there so we were down for anything.

But what I THOUGHT would happen is different than what ACTUALLY happened.

I met the head of the Bocconi entrepreneur club through a mutual friend a while back.

We got to talking online and he realized I would be in Italy for 3 months.

He asked me if I’d be in Milano. I wasn’t sure, but I love Milano, so I figured I could make it happen considering the cousins I was staying with live an hour from Milano.

Over the course of a few months we talked about the value I could bring with my 15 years of branding and marketing experience with startups, big brands, creatives, entrepreneurship, college kids, as well as touching upon the state of the modern-day business world.

I offered up my time to do a question and answer / ask me anything session for club members.

There you have it, that’s what we decided on. A 2-day Q&A / ask me anything.

So I showed up 4 pm sharp (not a common thing in Italy, to be on time), we set up the room and started talking.

The conversation went between scaling agencies, to writing SOW’s, to personal branding, finding your purpose as an entrepreneur, being comfortable in uncomfortable situations, toastmasters personal development, and how entrepreneurship is a spiritual journey we must accept to become successful.


But here’s the catch, to my surprise only 2 people showed up, Don and Karina. =O

Day 1 Bocconi


Talk about a shock, this could have been really deflating. We came to one of the most prestigious business schools in the world to add value to their budding entrepreneurship programs and only 2 people showed up!

You could look at this in a million different ways:

  1. Was my time taken advantage of?
  2. Was I too eager to work with a big university name and didn’t vet the opportunity correctly?
  3. Was timing not on our side, as exams were in session?
  4. Was I not a big enough name to draw people in?

Yes, all of the above, BUT when opportunity knocks, you gotta answer that fucking door.

The truth, I prepared for this. I prepared for no one to show up. You know why?

Because as an entrepreneur, you put yourself out there good or bad, and what defines us isn’t what happens but how we react to what happens.

I’ve stood in front of thousands of people, I’ve lectured in universities in different countries, I added value to multiple cultures, industries, and people of all ages and backgrounds.

One thing remains the same. Approach everything honestly, with humility and vulnerability and hope the 2 people who got to talk with me tonight received personal value they can take with them for life.

… With that out of the way, we said “fuck it” and looked for a place to write down our thoughts.

We got a lot more than that. In fact, we got the best experience we could have ever asked for in Milano.

We walked into GianFranco’s place. An enoteca / wine bar that welcomed us with open arms, full wine glasses, and conversations that stretched into very late into the evening.  

GianFranco's Place
The next day, after attempting to find wifi for a few hours, I finally got settled at a cozy hotel across the street from the university. Perfect, as my inbox was scaling out of control and the anxiety was starting to get to me.

After the night priors poor attendance, I seriously had no idea what to expect for day 2.

Like entrepreneurship itself, I was completely surprised.

Standing outside the building at 10 minutes to 4, a random student came up to me and asked me if I was Steven. He had seen my picture from the flyers and invite and we quickly hit it off.

Next thing you know, there were 5 students all surrounding me and chatting.

I know that this session would be better.

We sat around in a circle and starting conversing about entrepreneurship, their ideas / businesses, as well as our experience and how we’d handle certain situations.

It was humbling. Humbling to see the youth of Europe take such as interest in building their own business and questioning the status quo that has been establishing, not just in America, but across the modern world.

90 minutes went by pretty quickly.


This intimate AMA (Ask me anything) seemed to really hit home some core ideas I’ve been thinking about in regards to entrepreneurship and the state of business.

First off, it’s about mindset.

Seeing these kids, most of whom are in their early 20’s, asking the same questions we’re all asking makes me wonder if the state of entrepreneurship has become too trendy. Too much of a buzzword.

– How do I know if my ideas are good enough?

– How do I know what I’m really supposed to be doing?

– What if I fail?

– What if I succeed?

At the core, they all are or have struggled with mindset. With the idea that it’s okay to make mistakes. In fact, it’s expected and you should embrace it with open arms and an open heart.

Because in the end, that is all that really matters. Not IPO’ing the next Facebook, or making millions with Bitcoin. What truly matters is that you life your purpose, your life, to the best of your ability with your core values and day-to-day actions doing and saying the same thing.

Until next time, Bocconi. Keep hustling. Keep innovating. Keep on keepin on. It’s all we have to do in this life.