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When in Rome
Dennis's Serendipity Digest - weekly insights on personal growth, AI, tech, entrepreneurship, and more.
Hey,
it’s Sunday morning in Rome. After escaping hoards of fellow tourists I am glade to write to you from the couch of my Airbnb.
I'm on the 4th floor, the car noises outside do sound like the windows are open. Which they are not, the apartment just lacks insulation.
Let’s get to it.
📸 Photo of the Week

A sidecar seen next to the Colosseum. I hear telling a good story pulls the reader into the sidecar, right next to the author. I guess I have to try a ride like that.
Two ideas
David and I started a podcast (in German). It started with just the two of us, but over the next few weeks we’ll have our first guests.
Of course I bought a book to learn more about how to do it well. “Stop asking questions” by Andrew Warner. While he does interviews, we want our podcast to have a more conversational style. Yet I think there are some useful nuggets in his book. They go beyond podcasting and add depth to any conversation. Here are a few things that stood out to me:Before starting into the recording ask the guest: “What’s a win for you?”
“Join the resistance”, for example when someone says “I’m not a worrier”, you can say “I don’t usually get to talk to people who are 100% confident.”, this might lead them to correct you. I look forward to try this one out.
Reciprocity: sharing something personal helps build trust and encourages others to share safely.
The “dramatic lowball”, for example asking someone whether they do a million € in revenue a year, when clearly they do a lot more.
I like this one a lot: “Stop asking questions”, for example instead of asking them “How did you get your first customer?”, say “Tell me how you got your first customer.” The reason I like this one a lot is, because asking a lot of questions can come across as needy which reduces the quality of the conversation. Leading them through a better conversation is exciting.
Draw out interesting stories by asking “Tell me about a time when …” eg. “you experienced a failure”, or “What’s a past success that you think about often.”
Stop asking “Most” questions, I like this one, because I have done this myself in the past. By asking someone what their “most” whatever experience is, the mental load on them is a lot higher than if you leave out the “most”. Andrew recommends to rephrase most “most” questions, for example instead of asking “Who’s the most important person you hired?”, ask “Who’s an important person you hired?“
It’s about creating a safe space for depth and sharing.
BTW: I’m only halfway through the book. If you want more insights from Andrew’s book, let me know.
When in Rome: Here’s a little adventure that happened to my girlfriend (Olga) and me during our stay in Rome this weekend.
Olga wants to see the Colosseum and the Forum Romanum, but when we check GetYourGuide for tickets there are no slots for Saturday. It’s all sold out. So we do the adventurous thing and just walk to the Colosseum, hoping to buy a ticket in person.
As we approach the Colosseum, some dude with an information sign hanging around his neck (which looks like his daughter printed it for him) asks in an Indian accent “Do you need tickets?”. I confidently say “no”, which is a total lie.
About 280m after meeting that dude we reach a guardrail, which is about 10m above the ground floor of the entrance to the Colosseum. To my left the Colosseum. But then I look towards the right and I don’t like what I see.
There’s a line (and calling it a line, is a huge understatement). It’s thousands of people lined up, like a snake on Nokia towards the end of the game, where you don’t know where the start nor the end of the snake is. I don’t want to queue up there. I hate queuing. And this is the Ultramarathon of queuing. It’s completely ridiculous.
I start negotiating with Olga, whether she’d be comfortable to go by herself. She kindly says that’s ok for her. But it’s the kind of okay, where I know it’s not okay. So we decide to go downstairs, to get a better grip of the situation. Only to realise that we don’t know how to get downstairs. We’re clueless tourists here. At that point I wonder where is that Indian dude, maybe he can help.
We walk back and he’s still there, so I ask him: “Hey, how does this work, you got some tickets? I don’t want to line up. What can you offer?”
He makes a couple of phone calls and tells us that there’s a Spanish tour starting in 25 mins. We don’t speak Spanish, but then he mentions the magic words “skip-the-line”. That’s all I needed to hear. Tickets are 48€ each.
But we’re not interested in the tour, we just want to avoid the queuing so I propose: “Look we don’t need the tour, we don’t speak Spanish. We just need to get inside without waiting for hours. Can you do 25€ each, we’ll just go inside and leave the tour after getting inside?”
“No, cannot do.” he says.
But then he goes “You just want to get in fast? And you don’t need a tour, right?”
“Correct.”
“Okay, you pay me 20€ and I show you a spot where you can buy the tickets for 18€ each and you get in fast, no big queuing like down there.” and he points to the Snake like queue.
I look at Olga and before I can say something the Indian dude pulls out his smartphone, opens the calculator, types and speaks “You see, 20€ + 18€ + 18€ = 56€ total. Instead of 48€ each.”
I am sold and tell him “Let’s go.”
He asks us to follow him and we walk for about 4 mins getting further away from the Colosseum. Then we pass two police officers (and I wonder whether they might stop us, which they don’t), before we enter a dark alley, where he stops. “Give me the 20€ please.” I look at Olga and we both know this is not a good idea. He explains that he can’t take the money in front of the ticket counter, because it’s not his territory. I think whateva, let’s just try our luck and Olga opens her purse, pulls out the 20€ and hands it over to him.
He takes the 20€ and continues walking for at least another 5 mins. As we walk I am curious what the economics of selling tour tickets are, so I ask him about that. He tells me he makes 10€ commission on each ticket and I think to myself, no wonder he didn’t want to do the 25€ per ticket deal I proposed earlier.
When he goes “Usually I don’t do this, but you’re a nice guy.”, I think to myself, in the worst case he’ll just run away with the 20€ and we have a fun story to share.
About 2 mins later a large queue emerges and he tells me not to worry, this is only for groups, we pass it and there it is. A ticket office, with about 20 people waiting and three counters. I feel relief.
“Just buy the ticket and then go straight to the entrance.”, he says, pointing at the checkpoint where they check tickets for the long queue (which is supposedly just for groups). He reassures us that there’s no need to wait. We thank him and wish him well.
When we buy the ticket, I ask the lady where we get in, and I don’t believe what she does. She raises her arm, she points behind me, telling me “There, you need to get to the end of that line.”
“No cannot be. That line is only for groups, right?”
“No, this is for everyone. It’s for the security check.”
I don’t like where this is going. I preferred the Indian dudes guideline to go inside directly. So we pay the tickets and I pull Olga to me and whisper into her ear: “I don’t want to queue, let’s just try and go in directly.”
So we walk towards the ticket inspector at the entrance, leaving the long queue behind us. When we reach the security tape, I wave our tickets (like we have VIP tickets), towards the inspector.
The inspector uses two ticket scan pistols like in a Western movie and I like his energy. So I tell him as he approaches us “dude nice way to scan all the tickets”. At this point I am a bit nervous. I hold the first ticket toward him and see him aim that ticket scanning pistol at the ticket. In my mind I see a red alert popping up. “Careful, nasty tourist trying to get in without queueing”. But that never happens. Tickets are scanned and he lifts the security tape up, so we can enter. Eight steps later we’re at the security check. We made it.
I don’t know whether we did something wrong, but I felt relief to enter the Forum Romanum. Thanks Indian dude for helping us.
Three cool links
Stephen Wolfram’s (Creator of Mathematica) outdoor ‘walking desk’ setup to maximize productivity → I have no Idea how this guy is so prolific, but I find it hugely inspiring
Dickie Bush’s gratitude practice with an interesting twist → I especially like the third one “What do I have today that my current self, when sick or injured, would beg to have?“
(nur auf deutsch) David’s und meine neue “Meine Erste Million” Podcast Episode “#8 - Vom Waisenhaus zum Milliardär – Und warum Dennis beim Klettern fast alles hingeworfen hätte” ist live → hört mal rein
Personal note
Thanks for making it this far.
Now do me a small favour, I live off of compliments. Just send me a short email and say what you’re thinking.
I wrote it. You read it. How was it?
Dennis
P.S. - if you wanna go read this on a rad website (seriously) or send to a friend, here’s the link: check it out!