How a Hot Dog Stand Turned Into an 8-Figure Exit: The Wild Story of Sam Parr

If you want to know how to go from slinging hot dogs to making millions, pay attention. Because Sam Parr did just that. And not in some fake guru, Lamborghini-renting way. He actually built, scaled, and sold a media company to HubSpot for an 8-figure payday.

But before the big exit, he had to:

Get fired from Airbnb before his first day. Get shut down by the government for selling illegal alcohol online. Realize that running events is basically running into a wall of stress and misery.

This is the story of scrappiness, resilience, and a ridiculous work ethic. Let's break it down.

The Hot Dog Hustle & Selling Moonshine Online

Like all great entrepreneurs, Sam Parr didn’t start with a trust fund. He started with a hot dog stand.

While in college at Belmont University, he opened Southern Sam’s: Wieners as Big as a Baby’s Arm, an objectively hilarious and wildly profitable hot dog stand that pulled in $1,000+ on good days. A college kid making cash like that? That’s rare.

Then he got another idea: selling moonshine online. Because, obviously. He launched Moonshine Online, a website that legally (but actually, illegally) sold white whiskey over the internet. And it worked. Until the government shut him down for, you know, breaking the law.

The lesson? Regulations suck. Selling hot dogs is better. But more importantly, Sam realized he liked building businesses more than he liked school. So he dropped out and moved to San Francisco.

Getting Fired Before Day One at Airbnb

This part is brutal. Sam did what every hungry 22-year-old should do. He cold-emailed Airbnb’s CEO, Brian Chesky, pitched website improvements, and got a job offer. That’s how you get noticed. But here’s where it went sideways.

Before he could start, Airbnb ran a background check and saw that Sam had an old arrest (nothing major, but he hadn’t listed it on his application). They called him a liar and rescinded the offer on the spot.

Absolutely devastating. But instead of packing his bags, he stayed in San Francisco, started networking, and launched his first real startup.

Bunk: A Roommate Matching App That Got Acquired (Sort Of)

Sam met a guy named John Havel, who was running a Tinder-for-roommates app called Bunk. They teamed up and built it out, charging people to match with potential roommates.

Ten months later, they sold it.

For $15,000.

Not exactly buying a yacht money, but it was an exit, and enough to get Sam hired at Apartment List, where he learned how to run a legit business.

From Hustle Con to The Hustle (A Multi-Million Dollar Media Empire)

At Apartment List, Sam realized something. Startup events sucked. So he launched his own.

Hustle Con was a one-day event featuring founders who built businesses without venture capital. Sam spent $6,000 putting it together. It made $50,000 in revenue. Then he did it again and made $188,000.

But there was a bigger opportunity. The newsletter Sam used to market Hustle Con was getting way more attention than the event itself.

So in 2015, he pivoted. Instead of running a conference, he launched The Hustle, a daily business newsletter written in a sharp, funny, no-BS style.

It exploded.

By 2020, The Hustle had:

1.5 million subscribers $10M+ in revenue A wildly profitable premium community called Trends

And guess who noticed? HubSpot.

The $27 Million Exit to HubSpot

In early 2021, HubSpot bought The Hustle for a reported $27 million (some say it was closer to $20M, but who's counting?).

Sam had bootstrapped his way into a multi-million dollar payday. No crazy venture funding, no nonsense, just a solid product, a rabid audience, and a business model that actually made money.

But after selling, he wasn’t done.

Hampton: The $8M Founder Community

After taking a break, Sam got back in the game with Hampton, an invite-only mastermind group for high-growth founders.

This thing took off insanely fast.

1,000+ members within months $8M+ ARR just from memberships A vision to hit $100M+ in revenue

Why does it work? Because founders are lonely. Hampton gives them a vetted, exclusive network where they can actually talk shop with people who get it.

What Can You Learn From Sam Parr?

1. Cold Emails Can Change Your Life

Sam’s whole career started with a cold email to Airbnb’s CEO. Then he used cold outreach to get event speakers, newsletter subscribers, and more. Moral of the story. If you want something, email the person who can give it to you.

2. Bootstrapping > Venture Capital (Most of the Time)

The Hustle made $10M+ without raising VC money. Sam believes in owning the whole damn thing so when you sell, you keep the money.

3. Community Is a Cheat Code

The Hustle wasn’t just a newsletter. It was a tribe of founders, business nerds, and entrepreneurs. Same with Hampton. If you build a loyal community, you have a built-in customer base forever.

4. Learn From Failure, Then Move On

Got fired? Lost money? Screwed up? Who cares. Sam got shut down, fired, and rejected before he hit big. But he kept going.