How Sam Parr Went from Selling Hotdogs to Running The Hustle and selling to Hubspot for $27 million

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Table of contents

  • Company - The Hustle
  • Founders - Sam Parr & John Havel
  • Based in San Francisco Bay Area, US
  • Started in 2015
  • Around 30 employees
  • Media company
  • Newsletter with over 1M subscribers
  • Revenue - $15 million

Sam's hotdog hustle

Sam Parr, a college student in Nashville, was working for Mike Wolfe, the main guy on the TV show American Pickers, when he realised there were no places to eat or drink near the store. 

A man named Doc offered to rent him a hot dog stand, and Sam decided to give it a shot. He researched the law and found a location outside a music venue, Station Inn, which was popular with customers. 

He asked the owner's permission to be outside his building, which he got. Sam then found a commissary, which he needed by law to prepare the food. 

He didn't have enough money, so he asked the bar owners if he could use their kitchens, and they agreed.

Sam got his rig approved by the health department and got a business license and an encroachment permit at the DMV. He used his license to get access to Restaurant Depot, a bulk food store and bought $500 worth of supplies and a few brands of hot dogs and onions. 

He started with Vienna beef dogs, mustard packets, onions for the grill, soda + water, and chips.

The night before launching, Sam did a test run at home. He prepared everything in the kitchen and used the cart in his driveway to test it. He had the entire neighbourhood come by and eat for free as a test run, and it was like a block party. He opened for the first day three weeks later.

Sam worked on his corner from 10:30 am to 3 pm, then went to class. He contacted a radio station, and they let him work their summer concert series. 

He would work at track meets and high school sports events and sell Gatorade + hot dogs. Sam used Square and would charge 40 cents to use a credit card.

Sam could eventually hire some friends, Carly and Rydell, who worked with him at the stand. Rydell had gold teeth and had spent 25 years in prison for assault.

They'd all hang out each night and have lots of fun. Rydell would work the stand when Sam had class and get most of the day's profit. 

At night, Rydell wore a black leather jacket and gloves, and people asked if they were famous and if he was their bodyguard. 

Sometimes, Sam would sleep on the street for 2-4 nights to get to the best corner during big street music festivals.

Sam's hot dog hustle was hard work, and he used to get horrible sunburns. 

On a slow day, he would make $200, on a good day, he would walk home with $1,000 or $2,000 cash in his pocket. 

Moving on from hotdogs

Sam started an online store, he'd be in class, and his phone would be going ka-ching. He'd leave class with a thousand dollars in his PayPal account. Sam liked this more than hustling and selling hot dogs.

A note from Sam's old Tumblr site "Ordered by the government to shut down MoonshineOnline, my online liquor store."

The business was an online liquor store. But eventually, Sam got rid of that and the hotdog stand and moved out to San Francisco.

Sam moves into tech

It all started when Sam cold emailed a guy named Brian, who had a company called Air Bed and Breakfast (now known as Airbnb). In the email, he expressed his interest in the company and offered to help make it better.

Surprisingly, Brian responded and invited Sam to come for an interview. Sam claimed he was in the Bay Area and booked a flight to San Francisco.

Sam got the job, eventually got rid of all his belongings, and moved to San Francisco to work for the company.

Sam admitted he had no idea when asked how he knew that Airbnb was the right company for him. He thought it sounded cool, and he was impressed that one of their early employees was a famous runner who had quit his running career to work for the company.

Unfortunately, just before he started his new job, Airbnb called him to rescind the offer. They claimed that Sam had lied on his background check and that they couldn't hire a liar. 

Sam had failed to disclose a past arrest on the background check and had mistakenly thought he didn't have to disclose it because he hadn't been convicted.

Although devastated by the setback, Sam didn't let it stop him. He continued to pursue his passion for tech. 

Sam starting his own thing

While it was a devastating experience for Parr, it turned out to be a turning point in his life. 

He realised he needed to get clean and rebuild his life, so he decided to stay in San Francisco and start a book club to build his network. 

He also collaborated with a website designer to create a roommate-matching app called Bunk, which they eventually sold to Apartment List for $15,000.

Parr continued working with Apartment List and eventually made about $100,000 throughout his contract. However, once the contract was over in 2014, Parr found himself at a crossroads. 

He was still determining what to do next but knew he wanted to continue working in the tech industry.


The concept of Hustle Con came to Sam Parr when he was trying to figure out his next move after leaving Apartment List. He envisioned it as a one-day event where startup enthusiasts could get practical advice on the industry. 

Parr started building the idea within six weeks of the conference despite not knowing whether it would succeed.

Leveraging his network and using content marketing strategies like newsletters, blog posts, and Reddit posts, Parr attracted 2,000 to 3,000 website visitors daily in the first month, translating well into Hustle Con attendees. 

With only $6,000 in investment, the first Hustle Con generated $50,000 thanks to sponsors and volunteers.

The following year, the second Hustle Con made $188,000 with a budget of just $17,000. While it was tempting to continue with what worked, Parr realized he didn't love the business model, as conferences were incredibly stressful to produce. He wanted to focus on writing content that engaged his audience instead.

After receiving positive feedback from readers who enjoyed his newsletters, Parr saw an opportunity to start something new. He began The Hustle, a media company that aimed to deliver engaging, informative, and entertaining content about business and technology to its subscribers.

Launching The Hustle newsletter

In 2014, Sam Parr started The Hustle newsletter with the same content marketing strategies he had used for Hustle Con. He began sending two to three weekly stories, which helped grow the newsletter. 

However, he also added a new tactic to the mix, posting outrageous content designed to go viral on Reddit. 

He shared stories like how Pandora founder Tim Westergren convinced employees to work for free and how a man made $50,000 a month selling plagiarized books about pickup artistry on Amazon.

Parr also created alter egos whose bylines could appear in opinion-based stories he wrote from different perspectives. 

For instance, he wrote about using LSD to treat depression under the name Steve Garcia. In contrast, Steph Whitfield wrote about men hitting on her through LinkedIn. He even created Reddit and LinkedIn profiles for these nonexistent writers. 

Parr was defensive when asked if the key to his early success with the Hustle was disingenuous, saying, "I did genuinely think: How does this character think about this? How would she react to this? Let's write my opinion on it. It was as made up as an opinion could be made up."

As the newsletter grew to between 75,000 and 80,000 subscribers, Parr secured his first advertisers, mainly companies whose founders he'd previously worked with through Hustle Con sponsorships.

These companies paid about $1,000 for placements, while he also raised around $800,000 from angel investors. 

However, Parr realised that creating outrageous content was exhausting and hard, and it took more work to develop new ideas.

That's when Parr thought the Hustle could create daily news that people could rely on. "I didn't know what would hit, but if we created news that people could rely on every single day, more people would engage with us," he said.

Rebranding the Hustle in 2016

In 2016, Sam Parr decided to rebrand The Hustle to news, taking inspiration from the daily newsletter TheSkimm. 

The decision proved wise, as The Hustle gained 100,000 subscribers in its first year, followed by an impressive 500,000 in the second year. 

By its third year, the newsletter had reached a staggering 1 million subscribers.

In June 2019, Parr expanded The Hustle's offerings by launching Trends, a subscription service that helps entrepreneurs spot hot opportunities. This new venture provided Parr with a recurring revenue stream. 

He also added a podcast to The Hustle's portfolio that same year. Parr partnered with Shaan Puri to co-host My First Million, a podcast where the two entrepreneurs discuss business ideas. 

Although the first episode was downloaded 60,000 times, those numbers quickly dropped to around 10,000 per episode.

According to Parr, growing the podcast was one of the toughest challenges he has ever faced. Despite the initial struggles, he and Puri continued to record and release two to three weekly episodes for two years. Their hard work and consistency ultimately paid off, leading to hundreds of thousands of monthly downloads.

How The Hustles ambassador program got 300K email subscribers

There are two ways that The Hustle invites new ambassadors: through an ambassador landing page on their website and via email to existing newsletter subscribers.

The ambassador landing page is easy to read and highlights the program's benefits. It's a no-brainer for people who enjoy The Hustle's content, and the landing page directs them to a simple opt-in form. 

When someone opts in, they receive an unforgettable thank-you page with a GIF of a man nodding his head.

Existing subscribers receive an invitation to become an ambassador a few weeks after they sign up for the newsletter. 

Each subscriber has a unique sharing link to start referring friends immediately. The Hustle's ambassador program is designed for "joiners," or people who participate in low-barrier ambassador programs and may engage further through referrals, commenting, and sharing.

Once people are in the program, The Hustle gives them an online home where they can track their progress, view their unique sharing link, learn how to describe The Hustle and get tips on how to get more referrals. 

Ambassadors can also earn rewards, such as free swag and event tickets, based on the number of referrals they generate. 

The Hustle has refined its referral tiers over time to better understand the average customer lifetime value of a referral.

To keep rewards relevant and encourage virality, The Hustle chooses prizes specific to its brand and niche. 

For example, stickers are a popular giveaway item because people love to display them on their laptops, resulting in thousands of free impressions. 

The Hustle also goes the extra mile with each reward, including a handwritten note and branded packaging.

Finally, The Hustle provides tips and resources to help ambassadors feel confident talking about the company and promoting it to their friends. 

By the time ambassadors finish scrolling through the resources, they feel empowered to go out and invite more people to join the newsletter.

The Hustle's expansion

Every entrepreneur's success story is unique and full of twists and turns. The same can be said for The Hustle, whose journey was anything but a straight line. Despite the challenges, The Hustle's success was steady and unwavering.

As the newsletter grew, founder Sam Parr realised that relying solely on a small team of writers was not sustainable, particularly with the controversial and drug-related content they created. He recognised the need for a change in direction.

With that in mind, Parr shifted The Hustle's focus towards business-centred content, featuring trends and fresh ideas in the entrepreneurial world. 

This pivot led to the creation of, an exclusive community-based newsletter designed to explore new business opportunities and creative ideas to help entrepreneurs achieve their goals.

Think of as an interactive Netflix for entrepreneurs, a space to network, learn, and share ideas with like-minded business enthusiasts. Here, entrepreneurs can find inspiration and practical insights to help businesses grow and flourish.

When Sam knew it was time to sell The Hustle

Parr had always been upfront about his limitations as a business person. He felt that managing the day-to-day tasks of running The Hustle was outside his skill set, and he longed to focus on his creative passions. 

But when he received an email from HubSpot in October 2021, he seriously considered selling the brand.

HubSpot, a marketing software company, initially approached Parr with a vague partnership proposal. But Parr wanted to cut to the chase. He asked them directly if they were interested in buying The Hustle. When they confirmed they were, Parr decided to be completely transparent with them.

In an email to HubSpot, Parr listed every reason why The Hustle had its flaws, as well as what made the brand great. To his surprise, HubSpot was on board with everything. The deal was made, and Parr made over $20 million from the sale, some of it in HubSpot stock.

Selling The Hustle was the best move for Parr. He could now focus on his creative endeavours and the things he was passionate about while leaving the management of The Hustle and Trends to HubSpot. Parr continues to host his podcast, My First Million, but he's excited about what the future holds for him and his creative pursuits.

Why Hubspot bought The Hustle

HubSpot's acquisition of The Hustle was a strategic move aimed at expanding its reach and attracting a broader audience. 

The Hustle's unique content creation approach, combining humour, wit, and intelligence, perfectly fits HubSpot's brand values. 

According to HubSpot's CEO, Brian Halligan, The Hustle is one of the most innovative media companies. The company is thrilled to bring its unique style and approach to its customers and the broader business community.

In addition to its newsletter, The Hustle also produces two popular podcasts: The Hustle Daily Show and My First Million. The Hustle Daily Show offers daily news and commentary on the latest business and technology trends, while My First Million interviews successful entrepreneurs and business leaders.

From its humble beginnings as a small newsletter with only 300 subscribers, The Hustle has grown into one of the most influential media companies in the United States, with millions of readers and listeners.

The Hustle's success is a testament to the power of diverse content, innovative marketing strategies, and the perseverance and vision of its founder, Sam Parr.

What's next for Sam Parr? 

Parr said he wants to have kids and start a new project, though he still needs to settle on one. "When I sold, I was a person with poor eyesight who put on glasses and saw the world differently," he explained. "I was like, 'Oh my God, living is so wonderful!' This is life? I could have been living this for a time. I just felt great."

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