From Hot Dogs to Millions: Lessons on Connection with Sam Parr

Welcome to the latest issue of Future of Culture, where we explore what it means to create meaningful connections at work and beyond.

This week, I’m excited to share insights from my conversation with Sam Parr—a founder, storyteller, and community builder whose journey from slinging hot dogs to building multi-million-dollar businesses is anything but ordinary.

I’m a long time listener and first time caller (or in this case podcaster) with Sam. I’ve long admired the way he approaches business, and life.

I first met Sam after joining Hampton.

Like many founders, I was searching for a community of peers who I could relate to and confide in —the highs, the lows, and the unique challenges of building something from scratch.

Hampton delivers that, and Sam’s authenticity in how he approached building community left a mark on me.

In our conversation, we unpacked his journey—from running hot dog stands in Nashville to founding The Hustle, launching Hampton, and hosting the wildly popular My First Million podcast.

Here’s his story and what we can all learn from it.

From Hot Dogs to Airbnbs: The Origin Story

Sam’s entrepreneurial journey started in Nashville, where he launched a chain of hot dog stands aimed at the city’s thriving nightlife scene. Some nights, he’d make $80. Other nights, he’d walk away with over $1,000.

From there, Sam landed a shot at Airbnb, back when it was still “Air Bed and Breakfast.” He packed up, moved to San Francisco, and was set to start—until a background check derailed the opportunity.

That setback pushed Sam to go all-in on himself. He started a small company, sold it for enough to live for a year, and eventually launched HustleCon, a conference for entrepreneurs that would lay the foundation for his next big move.

The Hustle: Napkin Math to Millions

The Hustle started as a simple idea: a daily email newsletter that delivered business and tech news in a voice people actually enjoyed reading.

Sam’s belief in the business was based on what he calls “napkin math.”

 “If I get someone to subscribe one time via their email, and they stick with me for, say, a year, and I talk to them this many times per week… That’s only 1,200 words I have to write per day. And if I charge advertisers $40 per 1,000 impressions, I can make millions.”

At the time, email newsletters weren’t “cool.” Investors dismissed the idea, calling it small-scale and outdated. But Sam saw it differently.

With scrappy experiments—like living on Soylent for a month and exposing shady Amazon Kindle scams—Sam and his team turned The Hustle into a newsletter with over 3.5 million subscribers. By 2021, it was generating $20 million a year in revenue and caught the attention of HubSpot, which acquired the company for tens of millions of dollars.

“People laughed at the idea of newsletters. But I thought, if you have someone’s attention, does it matter whether they’re on Safari, Chrome, or their email app?” - Sam Parr

In an age where content is king, creating a message that resonates with your community is key.

Hampton: A Community for Founders

After selling The Hustle, Sam turned his attention to solving a problem he’d faced himself: the loneliness of being a founder.

That’s what led to Hampton, a private community for CEOs and business leaders.

Unlike most “networking groups,” Hampton focuses on depth over scale. Members are placed in small, curated cohorts that meet regularly to tackle their toughest challenges—everything from layoffs and fundraising to navigating personal burnout.

 “I realized that a big part of my own success came from having someone I trusted to talk to about work, life, and money. Hampton is designed to give founders that same support.” - Sam Parr

My First Million: Sharing the Blueprint

While building Hampton, Sam also co-hosts the wildly successful podcast My First Million. What started as a side project at The Hustle has grown into one of the top business podcasts in the world, with over 2.5 million monthly downloads.

 “It’s not scripted. When we log on, we don’t even say hello until we hit record. That’s why it feels real—it’s just two friends having a conversation.” - Sam Parr

The show blends actionable business advice with personal stories, featuring guests like Andrew Wilkinson, Rob Dyrdek, and Dharmesh Shah. But its real magic lies in the chemistry between Sam and his co-host, Shaan Puri.

“We just talk about stuff we’re curious about, whether it’s Charlie Munger, fitness stacks, or new business ideas. The goal is to keep it fun and valuable.” -Sam Parr

Lessons from Sam on Building Connection

Sam’s career is full of lessons on creating meaningful connections—whether with customers, employees, or fellow founders. Here are three takeaways I’m applying at Marco:

1. Start Simple: Great ideas don’t need to be complicated. Whether it’s a newsletter or a team retreat, focus on delivering value in a way that’s clear and consistent.

2. Know the Difference Between an Audience and a Community: Sam explains this distinction perfectly:

    “An audience is one-to-many. You create content, and they consume it. A community is many-to-many. Even if you stop creating, the people in the group will keep interacting and building together. That’s the magic of a real community—it becomes self-sustaining.” - Sam Parr

   For companies, this means fostering environments where employees or customers interact and create value together, not just consuming messages from leadership.

3. Build Trust First: Whether you’re launching a company or hosting a team meeting, trust is the foundation for everything. Create spaces where people feel safe to share and collaborate.

Final Thought

Sam’s story reminds us that success isn’t just about hustling—it’s about creating something that connects people, whether that’s through a newsletter, a team retreat, or a founder community. What stands out most is his ability to turn simple ideas into powerful platforms by focusing on relationships first.

The challenge for all of us is this: How can we create spaces—at work or in life—where people feel seen, supported, and inspired to contribute? Because in the end, it’s not just about the things we build—it’s about the communities we build them with.