In this vlog, Ben Sharf chronicles a week-long trip to Italy with his girlfriend Giulia (Juliette) and her family, weaving together travel experiences, personal reflections, and entrepreneurial challenges. He describes the logistical strain of balancing work emails, a training schedule for an upcoming boxing fight, and family time while touring iconic sites like the Colosseum, Pompeii, Sperlonga, and the Spanish Steps. Ben reflects on how documenting his life with a camera can both romanticize moments and enhance presence. He shares insights from reading Sahil Bloom’s The Five Types of Wealth, applying its five wealth categories—time, social, mental, physical, financial—to his own life and urging other entrepreneurs to consider holistic success. The vlog details his boxing preparation, including breathing techniques, leg stamina work, and intense “puker” interval sessions with trainer Charlie. A business update highlights a milestone for his startup Platter: zero negative customer feedback in the implementation phase, boosting confidence for sales. Throughout, Ben emphasizes the supportive role of his girlfriend, her family, and friends in encouraging his content creation, and he underscores the importance of disconnecting, mindfulness, and gratitude while traveling. The video concludes with final day activities, reflections on journaling, and a call to action for viewers.
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Welcome back to another episode of the vlog. We conversate and do anything. I heard you talking in your sleep. You made it. Welcome to the Colosseum! I'm definitely not a huge tour guide person on vacation. I much prefer to be like immersed in a country's culture, but this is pretty cool. I don't know how the crowd is anymore. I feel like if you do one thing in Rome, it's going to the Colosseum, which is obviously the first thing we did. Smile! Cheers for you guys! The most challenging part of the trip right now is definitely balancing the time zone difference with my work schedule, training schedule, and then our family time and touring schedule. We were out today for like 8 hours touring around around. It is now past 12 o'clock at night and I have to do about an hour of work sending some emails and then have to wake up at like 6 or 6:30 tomorrow morning to get a workout in before getting on a train. This is definitely part of the game. So gonna get a little bit of work done and then head to sleep. We just got off a 45-minute bus ride and Julia was holding a coffee the entire time. Took 2 sips and we get off and what happens? She spills the entire thing all over my leg. Sorry. So fun. This is a great learning lesson. This is what I learned in therapy, because when she spilled the coffee on me, I was ready to lose my mind. But my therapist taught me you can only control how you feel and how you respond to situations. So it was very good. I just stood there in silence and didn't say anything. It was a growing up moment for me. Our first Italy sorbet experience. Wow. Two chickens in love. Honestly, looking at the amazing views here, and she just said something really interesting that I wanted to record, which is something that a camera forces you to do. As you guys know, this is like a new thing for me to basically start documenting my life, and the thing that she said was that a camera forces you or allows you to romanticize your life because there's moments that you have where you're maybe not thinking about like how beautiful or how special they are, but then you're like, wait a minute, I want to capture this on camera. And while in some ways it might force you to not be present because you're just focused on capturing a shot, in the same vein, I actually think it allows you to be present because you're basically picking a moment to film something and capture it because it's special. And it might have been subconscious to you, but once you turn the camera on, you can go back and like look at it and be grateful and appreciative for like having those special moments. I mean, I live in the chaos in New York City, not very often do I to just come to Italy and walk around with Giulia. Like, look how amazing this is. Welcome back to another episode of the vlog. We are currently in Sperlonga, Italy with Giulia's family. Sperlonga. Sperlonga. Week in the life as an entrepreneur trying to be chill, exploring nature. You should do it too, it's good for your mental. Oh my God, are you still alive? We're still good. I'm still new to this whole creator thing. I almost just dropped my camera in the ocean. The purpose of this video is basically just to shed light on the reality behind traveling as an entrepreneur. One of the beautiful parts about the 9-to-5 job lifestyle that I envy is the ability to like fully disconnect when you're doing things. But when you're an internet entrepreneur and you go away, it takes like a crazy level of discipline to fully try to disconnect. And it's something that I've really been trying to focus on this week. And something that I don't do very often in New York is read. And I always have glorified this idea of being a reader, but I've really struggled to do so. But this week I actually picked up a book for the first time in a while, and I sat down and read 50 pages straight, which maybe doesn't seem crazy, but I haven't done that in like years. And so I wanted to talk about it for a second. The book that I'm reading right now is called The Five Types of Wealth by Sahil Bloom. It actually talks about his life when he basically left the corporate world to go into being an entrepreneur and ultimately realizing that making as much money as you can is not the only barometer for living a successful life, depending on how you deem success. And he breaks it down into the 5 different categories, which are time, social, mental, physical, and financial. It's made me think long and hard just in terms of how I spend my time, who I spend my time with, what's really important to me. And it forces you to ask a lot of hard questions to yourself, right? Like, if you're watching this, think to yourself, How many times your mom or dad called and you're like, oh, I'm busy, like, I can't talk right now. Or you miss a family dinner or family vacation because you had to, like, go do this one thing for work, which, like, obviously it happens sometimes. But I think one of the problems is when you just get so fixated on maybe just making a lot of money, you lose sight of every other aspect of your life. And it asks really hard questions around, like, how you're prioritizing your intimate relationships, your personal relationships, your physical health. And I am just talking about this because it's more of a reflection for me that while at this point in my life the financial element is so important to me, I think it doesn't really matter if you're not filling up any of your other cups. And so I've really appreciated reading the book so far to force myself to hone in on each category and get really clear with writing down what's important within that and making sure that I'm not neglecting everything else at the expense of one bucket, because I don't think being super being fulfilled in one and being depleted in the others leads to a fulfilling life. So if you're also an entrepreneur who lives in like a crazy environment like I do in New York and you can resonate with this, I think this is definitely a book worth checking out. Even if you don't action against it, just like forcing yourself to think deeper about it when you're in the quiet environment, right? Like I'm in a beach town right now in Italy in peace and quiet in nature reading a book, which saying that out loud makes me laugh because I'm usually in the middle of the most chaotic part of New York City, like waking up, working out, meeting people, building things all the time, and I love it, don't get me wrong. But forcing myself to take small moments like this to just be grateful and to reflect and to just recalibrate as I continue to push forward, I think, is, is equally as important. Oh, and one more note that I wanted to share for all of you entrepreneurs that are watching this that want to start creating content but are super nervous about people judging you. Trust me when I tell you, finding a significant other and a significant other's family and friends who don't judge you but actually encourage you to kind of follow your passions is the most liberating thing in the world. You'll see in this video literally my girlfriend's mom participating in the vlog, and it just makes it so much easier to have fun with it because everyone has intrusive thoughts and self-doubts. But I am finally starting to find my groove and obsessing over making these videos because the people around me are encouraging to follow my passions. One of the best parts about vacation staying in a small beach town is you get a playground yourself. This fun little gym is my playground for the next hour. There is nobody in here and I get this amazing view of the beach. Let's get after it. Yeah! Pit your poison, I had one too many, I'm drunk in love, karla gela, quite enjoy it, my parents thought I'd be grown. I feel like I have two challenges right now in boxing training for the fight that I'm doing on November 6th. One of them is obviously learning how to breathe because when you get amped up, tired, or tense, lactic acid buildup really crushes you. The second one is my legs burn out, so I'm trying to do more high-rep leg workouts to just like build up the stamina on my legs because it's crazy how much your lower body burns from boxing. I'm still trying to figure out, but I only have 50 days before the fight, so doing everything that I can to basically build up the stamina on my lower body. I don't want to do the end of this workout. I've been sitting here on my phone just shitposting on Twitter, delaying the inevitable. Charlie, my trainer at my boxing gym, makes me do what he calls pukers, which are minute-long sprints on the treadmill with 10% incline, followed by a 1-minute plank as your rest time, and repeat that 5 times over. It's terrible, but I won't be able to live with myself if I know I just blatantly skip it. So here goes nothing. Just kidding. Treadmill's broken. Bike sprints it is. That's enough exercise for today. I don't think you can say that you made a vlog of your time in Italy without at least one shot of you crushing a gelato. Buongiorno! It is our final day in Italy today. Today is our final day in Italy. We have been here for about a week now. We did Rome, Pompeii, Sperlonga, and we are back in Rome. It is just Jewel and I today. Her family left this morning, actually. We've done a lot of touring over the first couple days of being here, so really just want to eat some food and chill. Also found a boxing bag in the gym, so probably going to do that for a little bit and then head back to New York tomorrow. Officially under 50 days out from the fight. Breakfast in bed and Netflix, box, Spanish Steps, Soho House, bowl of pasta, back in bed where we started, and then back to New York tomorrow. Pushing yourself to stay in shape on vacation is just such a mental battle. I feel like it takes hours, weeks, months to get in shape and just like a couple days to lose it. So it's such a mental battle, but so important to just continue to do it no matter where you are. We just got to the Soho House in Rome, gonna have a little bit of lunch. And on the last day, enjoying silence, which isn't something I usually have often. I'm gonna attempt to read and journal for a bit. I've been thinking about wanting to get back into journaling for a while, but just have struggled to do so. So I figured using this last day on vacation when I'm in a pretty calm headspace, going to attempt to be productive today after enjoying a wonderful meal with Miss Juliette. Can any of the guys watching this vlog right now relate to having a girlfriend who just needs to get her steps in every day when you don't want to? We are going to see the Spanish Steps right now because my dad has been telling me we have to to see it before we leave Italy. And I was like, great, we can go. She's like, yeah, let's walk. It's a 45-minute walk. I don't really know that many guys that like to do long-distance walking for fun. That's long distance. That's a long distance. 45 minutes. Well, I hope someone watching this can just comment and say that you can relate. Yeah, no, but I'm high-intense fitness person, so I'm an active lazy person. When I exercise, I exercise hard, and if I don't, it's all about efficiency. Come with me on a 45-minute walk to the Spanish Steps because my girlfriend made me. Win for the good guys. I convinced my girlfriend to let us get some watermelon midway through this walk because I've been such a good walker. She's rewarding me. Positive reinforcement. Because we still have like 30 minutes left. There's one thing I learned: good things come to those who wait. We're still on our walk to the Spanish Steps. I had one thought that I wanted to share. Tried to disconnect for this week, uh, I only worked like a couple hours a day, but I did join the all-hands meeting for Platter because we only do it once a month, so that definitely wasn't something I was going to miss. And I wanted to share one highlight from from that, which was that Kieran, my— one of my co-founders, shared on the call that over the last month we've gotten zero negative feedback from our customers that are in the implementation process of building their new storefronts. And I'd say this is probably the first time that has happened in 4 years of building the company, which is a huge milestone for us because remember like a couple years ago what it was like. I mean, everyone knows in startups you're basically building the plane while flying it. So to be able to get that feedback and just see response from everyone on the call is super cool because every time we hit like a new milestone, I'm always in my head thinking like, wow, it's like a real company now. You know, as one of the founders, I struggle always looking at it through the lens of what could be better because complacency will be the day that we die. But I have to say, this is definitely a moment to celebrate because now the level of confidence I have every time we sign a new customer is so high. And I think that confidence and conviction bleeds into our sales cycle when we're talking to really large brands. They can and genuinely believe it in our voice when we tell them that they'd be silly not to work with us. And the results just continue to compound. Are we there yet? Yeah. How far? Right here. No, we're not. Yeah. You'll never believe it, after 45 minutes of walking, we finally made it. You can do it! If you're still here— you're still here— I hope you enjoyed— if you're still here, we hope that you enjoyed another episode of the vlog, and you should like, comment, subscribe, etc. if you're feeling generous and you want to see more. And we had such a good time for Ben Sharf's time in Italy. What she meant to say is, I hope you enjoyed another episode of the vlog. We'd appreciate if you like, comment, and subscribe below. See you next week.
