Episode Length: 39 minutes

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Sam Parr catapulted to celebrity status within the startup world when he sold a daily newsletter called The Hustle for a reported 8 figures.

But how did this down-to-earth guy with no previous media experience build such a valuable company?

This episode breaks down that story. You’ll hear exactly how Sam Parr went from being a scrappy college kid with a hot dog stand to one of the leading voices in entrepreneurship.

Here’s what you’ll learn:

  • [2:05] How Sam sold The Hustle to HubSpot for 8 figures
  • [3:50] The business that got Sam hooked on building companies
  • [5:49] The white lie that cost Sam his job at one of the world’s most-successful startups
  • [9:45] Why The Hustle started as an events business
  • [12:19] The two unconventional growth strategies Sam used to grow The Hustle
  • [17:20] The turning point that allowed The Hustle to scale
  • [20:07] Sam’s leadership approach to running the day-to-day at The Hustle
  • [21:58] Sam’s tips for hiring freelance writers and sales reps
  • [24:40] How a podcast unexpectedly changed everything for Sam’s career trajectory
  • [27:40] The hobby-turned-business that helped diversify The Hustle’s income
  • [31:35] Why a CRM company was interested in acquiring Sam’s media empire
  • [36:34] What’s next for Sam after a life-changing, 8-figure exit

Thanks to Sam for taking the time to share his story. You can connect with him on Twitter @thesamparr or his My First Million podcast.

Plus, a shout out to our sponsor for this episode, Chicago Partners, a team of financial advisors who specialize in wealth management. Get their support at ChicagoPartnersLLC.com.

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How Sam Parr sold The Hustle

Before he became the founder and creator of The Hustle, Sam Parr was a college student with an incredible opportunity: to work with Airbnb in its earliest stages.

“They gave me an interview, and [the CEO] offered me the job,” he recalled. “I flew back, left school, sold all my stuff, and flew back to San Francisco. The Sunday before I was supposed to start, Airbnb [called] me and took away my offer, saying I lied to them.”

Parr was floored, and tried to argue his case.

“In college, I had a little bit of a drug and alcohol problem and I got arrested,” he explained. “I didn’t tell anyone on the Airbnb background check. I just said ‘no’ on the checkbox that asks if you are currently under investigation … I forget exactly what it was, but I thought the way they worded it, that technically, I haven’t been convicted yet.”

Airbnb didn’t buy his explanation. “They were like, ‘No, you smart ass. You should have told us and we could have worked with you, but we can’t hire a liar,'” Parr recalled.

While losing the Airbnb gig was the “lowest point” in his life, Parr said it served a purpose: He learned from the experience and vowed to get clean and rebuild his life.

Sam Parr on rebounding from a “low point”

He decided to stay in San Francisco, get sober, and start a book club to build his network. He also teamed up with a website designer to create a roommate-matching app called Bunk. They sold that business to Apartment List for $15,000, and Parr took a job with the company, eventually making about $100,000 over the course of his 366-day contract.

Once Parr left Apartment List in 2014, he wasn’t sure what he wanted to do next. He began developing the idea for Hustle Con, a single-day event where attendees could get tactical advice on the startup industry. “I did that just as a way to kill time, thinking maybe this isn’t going to be The Thing, but maybe it’ll help me find The Thing,” he said.

With just six weeks to go before the conference, Parr leveraged his network to book speakers and sponsors, using content marketing newsletters, blog posts and Reddit posts to attract website visitors. After the first month, he had an average of 2,000 to 3,000 website visitors daily, which translated well into Hustle Con attendees.

Thanks to sponsors and volunteers, Parr spent just $6,000 on the inaugural Hustle Con, which raked in a whopping $50,000, he said. Building on its success, a second Hustle Con the following year made $188,000 on a $17,000 budget.

While it would have been easy to keep doing what worked, Parr didn’t love the business model.

“I thought conferences are kind of cool, but kind of a pain in the butt,” he said. “All the revenue comes in the last two weeks. It’s incredibly stressful. It’s kind of training for a marathon. It sucks. It sucks. It sucks. Then you are done and you’re [like], ‘Oh, that was kind of fun. I want to do it again.’ But it still sucks 98% of the time.”

Parr realized producing the event wasn’t “The Thing” for him, but writing the content that drove its attendance could be.

“People would write me saying, they love this newsletter, [that] it’s hilarious or they learn a lot,” he explained. “I thought, ‘Well, maybe this is The Thing.’ That’s when I started The Hustle.”

Launching The Hustle as a newsletter

In 2014, Parr began sending two or three stories a week, growing the newsletter with the same content marketing strategies he had used for Hustle Con. He also added a new tactic: posting “outrageous” content designed to go viral on Reddit, including a story on how Pandora founder Tim Westergren convinced employees to work for free and another on a man who made $50,000 a month selling plagiarized books about pickup artistry on Amazon.

In addition, Parr created “alter egos” whose bylines could appear on opinion-based stories he wrote from different perspectives. For example, “Steve Garcia” described using LSD to treat his depression, and “Steph Whitfield” wrote about men hitting on her through LinkedIn. He even created Reddit and LinkedIn profiles for these non-existent writers.

When asked if the key to his early success with the Hustle was disingenuity, Parr hedged.

“I would take things that were happening in real life that people had told me about, and I would use those alter egos to say different opinions,” he said. “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.”

Once he had between 75,000 and 80,000 newsletter subscribers, Parr got his first advertisers, mainly companies whose founders he’d previously worked with through Hustle Con sponsorships. They paid about $1,000 for placements. He also raised around $800,000 from angel investors.

But it was getting harder and harder to come up with content to publish. “Coming up with these crazy stories and doing outlandish stunts — it’s exhausting and it’s hard,” he admitted. “I didn’t know what’s going to hit, but if we created news that people could rely on every single day, more people are going to engage with us.”

On May 1, 2016, inspired in part by the daily newsletter TheSkimm, Parr rebranded The Hustle to news. And he was right: The Hustle grew to 100,000 subscribers its first year, then 500,000 in its second year. By its third year, the newsletter had racked up a whopping 1 million subscribers.

In June 2019, The Hustle launched Trends, a subscription service that helps entrepreneurs identify hot opportunities. That helped Parr add a recurring revenue stream to the business.

That same year, Parr added a podcast to The Hustle’s portfolio. Partnering with Shaan Puri, Parr became co-host of My First Million, where the two entrepreneurs discuss business ideas. The first episode was downloaded 60,000 times, though those numbers quickly dropped into the 10,000 range. Parr described growing the podcast as one of the hardest things he’s ever done, explaining that hard work and consistency — recording and releasing two to three episodes a week for two years — is what ultimately helped them get to hundreds of thousands of downloads each month.

How Parr knew it was time to sell The Hustle

Parr credits his team for the brand’s meteoric rise, but he was also tired of managing tasks he felt were outside his skill set.

“I’m not really that much of a business person; I’m an artist. I was being a business person and I was worn out and I wanted to create, not have meetings and manage people,” he said. “So I was really worn out.”

Parr had started to look for a CEO who could handle the management side of the business when he got an email from HubSpot, a marketing software company.

“They emailed me saying they want to do a partnership. That was vague to me,” he said. He replied, asking them to be clear: “Just tell me, are you trying to buy us? Because if you are, maybe we can have a conversation, but don’t waste my time. And they go, ‘Yeah, we’re trying to buy you.’”

To save time, Parr leaned into transparency. “I sent them an email and I listed every reason why we are bad, why we suck, and what’s wrong with our company,” he said. “I also listed every reason why we’re awesome and why this maybe could work. They replied and they go, ‘That sounds great. We’re OK with all this.'”

Selling was ultimately the best move for Parr. He sold in February 2021 for $17.2 million in cash, according to Hubspot’s SEC filing, plus equity. Parr said the total deal was more than $20 million, and the value of his HubSpot stock doubled shortly after the sale. (Other outlets have valued the deal at about $27 million.) He’s still hosting My First Million, but has handed over all his responsibilities for The Hustle and Trends to HubSpot.

What’s next? Parr said he wants to have kids and start a new project, though he hasn’t settled on one yet.

“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.”