Finding Startup Serendipity in New York City

TL;DR

New York City's unique energy creates unparalleled serendipity for founders. Simply by being present, you can meet the exact people you need to accelerate your startup. #VentureStep #NYC #Entrepreneurship

INTRODUCTION

Choosing a city is one of the most critical decisions a founder can make. It’s not just about finding an office space; it’s about immersing yourself in an ecosystem where the right resources—people, capital, and industry expertise—are in close proximity. In this solo episode, Venture Step host Dalton Anderson details his exploratory trip to New York City, a journey to test his hypothesis that the right environment can dramatically accelerate a startup from a mere idea to a tangible venture.

Dalton’s trip was a trial run to see if New York could provide the specific cluster he needs for his new venture in the reinsurance market. He discovered that the city's value isn't just in its established institutions but in its incredible density of talent and the serendipitous encounters it fosters. From random conversations at a bar to waiting in line for pizza, he repeatedly met the exact people who could provide critical feedback, industry connections, and advice on his entrepreneurial journey, proving that sometimes the magic of a city is its most valuable asset.

This episode is a deep dive into the unfiltered energy of NYC, the power of putting yourself in the right place at the right time, and how those chance meetings provided more progress than weeks of planned outreach could have. Dalton shares his personal experiences, his key learnings from Washington D.C. and New York, and outlines the concrete next steps for his startup, fueled by the validation and momentum gained from his trip.

KEY TAKEAWAYS

• New York City's density fosters powerful “serendipity,” where crucial professional connections can happen completely by chance.
• For industries like finance and insurance, physical proximity to the market “cluster” is a non-negotiable strategic advantage.
• Spontaneous, low-stakes conversations with strangers can lead to more significant breakthroughs and idea validation than formal networking.
• The raw, unfiltered energy of a major city can directly fuel a founder's motivation and belief in their mission.
• After gaining initial validation, the most critical next steps are building a minimum viable product (MVP) and securing a distribution strategy.

FULL CONVERSATION

Dalton: Welcome to Venture Step Podcast, where we discuss entrepreneurship, entry trends, and the occasional book review. ¹If you're watching on video, I'm in a unique place, not my typical recording studio. ²That's because I am in New York. ³Before I get into the whole episode, I want to start off with a video from Naval Ravikant. ⁴ So let me share my screen, kick that off.

Dalton: So that video encapsulates my visit to New York City. ⁵I was in between two places, San Francisco and New York City. ⁶I've never been to San Francisco, but I know what San Francisco is kind of about. ⁷But when I was thinking about the idea and the things that I wanted to execute, I was also thinking about the key resources that I would need in close proximity. ⁸

Why Location Is a Founder's Most Critical Resource

Dalton: I would relate this to if I was traveling to Mexico City or my travels in Tokyo or Seoul, when you go to these new places, you've got to figure out what are my key resources. ⁹This is subjective to yourself. ¹⁰My key resources was, if I need to get a quick bite to eat, what are the two places that I could go to? ¹¹If I need anything from the grocery store, where are the two shops that I like? ¹²If I want to work out, where's the workout parks at or where's the gym? ¹³Figuring out a way to settle into an area quickly makes sense when you have key resources. ¹⁴

But when you're starting a company, the key resources are the places or things that allow you to be successful. ¹⁵

Dalton: Simply put, if you're traveling somewhere, identifying the key resources as quickly as possible and then making sure that you know where they're at and you have a relationship with those resources. ¹⁶Same thing when you're starting a company. ¹⁷What I need for my idea is I need close proximity to the reinsurance market. ¹⁸I need to be in an area where if I needed to meet with investors, I could. ¹⁹I need to be somewhere where if I needed to take a flight internationally to London or Bermuda for the reinsurance market, I could and also be somewhere that would be considered a cluster for financial services or insurance. ²⁰When you're looking around in the U.S. there's only a couple of places where that qualifies and that would really be like a New York or Chicago, but New York is really the place. ²¹With all the insurance brokers, reinsurance brokers, which is people who get insurance for insurance companies. ²²That's typically done either in Bermuda. ²³They've got a pretty big cluster in Philly and New York and then London. ²⁴And then there's some stuff in Germany with Munich Re. ²⁵For the most part, those are the clusters. ²⁶

The Hypothesis: Can a City's Energy Accelerate an Idea?

Dalton: Those things are really important. And if I want to do what I want to do, that's where I have to go. ²⁷So I was giving a trial run and seeing how I like it and then getting a feel for the land. ²⁸I had a hypothesis that if I spent a couple of weeks here, it would be very productive and just the magic of the city and the magic of life and putting things out there and getting things back would just allow me to make progress on my ideas, which has been true multiple folds more than I expected. ²⁹

It's crazy what New York can do. It's just like a weird thing where you're just at a bar with somebody and they wind up being the person that you should meet. ³⁰

Dalton: It's so weird where it seemed consistently that I was meeting these people that I always needed to meet. ³¹They were just on the cusp of exactly what I needed. ³²It's hard to describe, but in this episode, I'm gonna be breaking down my experience in New York and a little bit of Washington, D.C. and just giving you an update on life and my progress with the startup. ³³

A Wellness Retreat in Washington, D.C.

Dalton: First off, let's walk through the agenda. So I got a startup progress update, then we have my experiences in New York City and in DC. ³⁴So first off, I would like to start with Washington DC. ³⁵I was able to spend a couple of days in Washington DC with my friend Luke and he just moved there for a big job. ³⁶Congratulations to him. ³⁷We spent some time and he also has an Equinox membership and I was able to be a VIP guest and we got to go to yoga classes and go to the sauna, steam room, and then after which we would take a really cold shower. ³⁸We were doing that literally every day. ³⁹It was almost like I went to a wellness retreat. ⁴⁰We're more like, okay, so we're gonna do yoga at 8 a.m., then we're gonna work out, then we're gonna do 20 minutes of the sauna, 20 minutes of the steam room, and then we're gonna do a five minute cold shower, and then we'll do a hot shower, and then we'll start our day. ⁴¹And that's what we did all the time. ⁴²For the four days there, three of the days I spent two and a half hours a day in Equinox just spawning out, just having a great time. ⁴³My back and my body and just my mind was recovered. ⁴⁴So nice, those classes are worth it. ⁴⁵Those yoga classes really unlock you. ⁴⁶There's a class like unlocking your body, deepest stretch you've ever had in your life. ⁴⁷And I loved it. ⁴⁸

From Grungy Dive Bars to Legendary Burgers

Dalton: It was great, honestly. I loved every minute of it. ^49494949After that we went out, I think one night out late and we went to this place called Lucky Buns for a hamburger. ⁵⁰Phenomenal hamburger. ⁵¹It was like nine bucks, 10 bucks, top five hamburger I've ever had. ⁵²And then after Lucky Buns, we went to this place called Dance Cafe. ⁵³Dance Cafe is some kind of legendary grungy dive bar that you know, you're drinking out of a condiment cup and you are located maybe on a pool table with a blue tarp on it. ⁵⁴The lights are all flickery, it's dirty and it's just packed with people and they're drinking out of mayonnaise and you're drinking out of ketchup. ⁵⁵It was $15, but $20 total because you had to provide a $5 deposit on your condiment cups that you were using and your two shot glasses. ⁵⁶We got pineapple and rum. ⁵⁷Dude, we were pirates, which I thought was a great theme chosen by Luke. ⁵⁸It was a pretty cool experience. ⁵⁹I've never experienced anything like that in my life. ⁶⁰If you have the opportunity and you're in Washington, DC, definitely give it a shot. ⁶¹

First Impressions: The Unfiltered Energy of New York City

Dalton: Moving on to New York City, loving New York City. ⁶²New York City is just a different animal, especially from coming from DC. ⁶³It hits you hard in the face. ⁶⁴

DC's raw, it's unfiltered, it's fast, it's exhilarating, it's everything you'd ever want it to be. ⁶⁵

Dalton: I've only been here for a couple weeks and I love it so much, it's great. ⁶⁶One of the things that I think it's great at is that it's unfiltered. ⁶⁷Like it's unfiltered life. ⁶⁸You could see the tragedies of life and mental health issues on the streets. ⁶⁹You could see the polish and the status and all these other societal things. ⁷⁰It has everything, everything you could ever want. ⁷¹And you can almost do anything, you can almost find anything at any time. ⁷²If you wanted to do something at a random 4 a.m. on a Sunday, there's probably something that is related to what you want. ⁷³And it was refreshing to be in a big city like New York City that's not in a foreign country because Tokyo is sick. ⁷⁴Seoul is so sick. ⁷⁵But I can't read Japanese. ⁷⁶I don't know Korean. ⁷⁷Getting around and communicating in New York City has been so easy. ⁷⁸It's just crazy how easy it is when the signs are in English and everything's in English. ⁷⁹

The Power of Spontaneity: Jazz, Speakeasies, and Comedy

Dalton: Luke was able to come in with me. ⁸⁰We took the train, which was great. ⁸¹It was only a three hour train ride and we just popped up a hot spot and worked on the train on Sunday. ⁸²Luke's really into jazz. ⁸³And so we went to a jazz show and saw this guy named Doc. ⁸⁴He was great. ⁸⁵He ripped the guitar, crazy. ⁸⁶ Afterwards, we went to this place. It was a Speakeasy inside of Five Guys. ⁸⁷I think it's in East Village. ⁸⁸It was super cool. ⁸⁹The vibes are great. ⁹⁰The music was great. ⁹¹And it was late on a Sunday. ⁹²It was packed on a Sunday at 11:30. ⁹³ None of it was planned. It wasn't like this whole planned itinerary thing. Everything was spontaneous. ⁹⁴And to do that stuff spontaneously on the cuff of a conversation is pretty cool. ⁹⁵And then we also went to the Comedy Cellar and I saw Mark Norman along with other comics and that was really cheap. ⁹⁶It was like 15 bucks. ⁹⁷Just every day I was doing something incredible. ⁹⁸

Startup Serendipity: Meeting the Right People by Chance

Dalton: On top of that, I was meeting great people as well. ⁹⁹And I'm not searching these people out. ¹⁰⁰I'm just walking around the city, eating at a bar. ¹⁰¹And I just talked to the person to my right or my left. ¹⁰²And it turns out these people are fascinating. ¹⁰³For example, I randomly met with someone that was connected with reinsurance and was able to pitch ideas to them. ¹⁰⁴That was great. ¹⁰⁵And see what the interest was for the startup idea of the event cancellation thing. ¹⁰⁶They said, "Yeah, we would. That actually sounds pretty cool. You just got to think about it a little bit more. You got to get the right story together. We'd want to see the pricing and the risk aggregation strategy, but on a high level, 10,000 foot view, this idea seems pretty cool and legit." ¹⁰⁷Then I was at a bar watching the game and I randomly was at this reinsurance bar and they were talking about surplus lines and reinsurance and commercial. ¹⁰⁸I overheard their conversation, let them finish their thought, and just introduced myself. ¹⁰⁹One of them was like, "Hey, I'm actually a senior person at Guy Carpenter," which is a really big reinsurance company. ¹¹⁰"And I'd love to have a chat with you." ¹¹¹And he gave me his card. ¹¹²That was just me just walking about the city, doing my own thing, minding my own business, and asking for some things, and the city just gave it right back. ¹¹³

I'm not searching these people out... I'm just walking around the city... and before you know it, the city's just given back. ^114114114114

Dalton: The conversation I had with the guy yesterday, his name was Roy. ¹¹⁵Roy is some senior engineer at Amazon and eventually wants to found his own company. ¹¹⁶I literally just asked the guy, "Hey, are you a photographer or is this just a hobby?" ¹¹⁷Then he started asking me questions and before I know it, the rest was history. ¹¹⁸I got his number and he said that he's had a couple of his friends that graduated from Y Combinator and that he'd be willing to connect me with them and help me out. ¹¹⁹Incredible. ¹²⁰¹²⁰

Getting Real-Time Feedback From Strangers

Dalton: Later that night, I'm waiting in line to get pizza at John's Pizzeria on Bleecker street. ^121121121121The guy's complaining because the line's long. ¹²²I turn around and I was like, "Man, don't worry about it. It's only five minutes." ¹²³Everybody thought that was funny. ¹²⁴

I said when your soldiers are losing hope, you've got to give them inspiration and then push them a little further. ¹²⁵

Dalton: There was these two women behind me that thought it was hilarious that I did that. ¹²⁶We wound up sitting next to each other. ¹²⁷It sparked up conversation. ¹²⁸They asked me why I'm here. ¹²⁹And I was like, "Oh, I'm trying to trial New York City and see if I want to live here and eventually start a company here." ¹³⁰And eventually it kind of went into like a full vetting of my idea. ¹³¹They were like, "Okay, so what if this happens? How would you do this? How are you going to secure partnerships and distribution?" ¹³²They were kind of really ripping me. ¹³³It was a good conversation. ¹³⁴One person was an AI person at Adobe. ¹³⁵Once again, I'm not searching out for these people. ¹³⁶I'm just waiting in line and I am just talking to the person next to me. ¹³⁷

The Verdict: Going All-In on New York

Dalton: The energy of the city and what it's giving back in such a short amount of time without me providing any legitimate effort... I'm all in. ^{138138138138138138138}I am legitimately all in. ¹³⁹

No doubt in my mind that if I moved to New York, I can become the person I want to be and consistently execute the things and the goals and the ambitions that I have. ¹⁴⁰

Dalton: It can be done in New York city. ¹⁴¹No problem. ¹⁴²There's so much opportunity here. ¹⁴³There's so many things and people willing to help you that it seems like almost anything is possible. ¹⁴⁴

Next Steps: Building the MVP for Automated Event Protection

Dalton: Since I've made some serious progress with the startup idea, I really need to get down and start working on the MVP and secure a co-founder. ¹⁴⁵I can apply to these incubators without a co-founder and they'll help match me up with somebody. ¹⁴⁶So that's fine, but I do need to work on the MVP and start building out the machine learning model that deals with frequency and severity and running through the weather data from the history of the United States. ¹⁴⁷And if it does occur, having a separate model run that would predict the severity of the occurrence. ¹⁴⁸And then from there, I could create a pricing model. ¹⁴⁹Those things aren't too hard, but they will take some time. ¹⁵⁰Afterwards, I'll have to build out some kind of thought process on distribution or securing distribution for weddings. ¹⁵¹I was thinking there might be banquet owners or wedding planner websites who have the need and the ability to allow me to go onto their platform and be an additional offering. ¹⁵²Ideally, the user just clicks, "I want automated event protection," clicks the button, and then that stuff is sent to me via API. ¹⁵³

The Founder's Path: Incubators, Sacrifices, and a Sweat House

Dalton: It seems as if there's interest in the reinsurance market. ¹⁵⁴There's interest with the investors. ¹⁵⁵There's a high possibility that I can get into an incubator. ¹⁵⁶So really the only thing that I need to execute on is MVP, distribution ideas, and vetting that. ¹⁵⁷After my application, I would have to move to San Francisco for three months. ¹⁵⁸And then after that, I would probably live at my Nana's for three months and live as impoverished as I can. ¹⁵⁹And then from there, move to New York City, live in some kind of sweat house, like some founder house that's got hopefully four or five other founders and we just live there and cook and we just make cool stuff. ¹⁶⁰That would be perfect. ¹⁶¹The date that I start the incubator, I'll have to quit my job. ¹⁶²And when I quit my job, I'll lose all my salary. ¹⁶³

Sustained progress instead of bursts of inspiration. ¹⁶⁴

Dalton: That was my update for New York City. ¹⁶⁵I hope that you find the episode intriguing and informationally light, where it's just kind of you just listening and hearing my experiences. ¹⁶⁶Until next time. ¹⁶⁷I hope that wherever you are in this world, you have a good morning, good afternoon, good evening. ¹⁶⁸Thanks for listening. ¹⁶⁹

RESOURCES MENTIONED

• Naval Ravikant
• Equinox
• Lucky Buns (Washington D.C.)
• Dance Cafe (Washington D.C.)
• Five Guys
• Comedy Cellar
• Mark Norman
• Y Combinator
• John's Pizzeria on Bleecker Street
• Adobe
• Guy Carpenter
• Amazon
• Google DeepMind

INDEX OF CONCEPTS

Naval Ravikant, San Francisco, New York City, Mexico City, Tokyo, Seoul, reinsurance market, London, Bermuda, Chicago, Philly, Germany, Munich Re, Washington D.C., Luke, Equinox, yoga, Pilates, Brazilian Jiu Jitsu, Lucky Buns, Dance Cafe, East Village, West Village, Doc, Five Guys, Speakeasy, Comedy Cellar, Mark Norman, automated event protection, event cancellation, risk aggregation, Guy Carpenter, Roy, Amazon, Y Combinator, John's Pizzeria on Bleecker Street, Adobe, Aon, MVP (Minimum Viable Product), machine learning model, API, founder house, Google DeepMind, Dallas, surplus lines, parametrics, maritime