Sam Parr - Founder Of The Hustle, Hampton And My First Million Podcast

4 Startup Secrets from Sam Parr, Founder of The Hustle

In a recent episode of the Forward Obsessed podcast, hosts Pete Sena and David Salinas sat down with Sam Parr, the founder of The Hustle, a popular email newsletter and media company that he successfully sold to HubSpot for $27 Million. Sam is also the co-host of the My First Million Podcast, and is currently building as the co-founder of Hampton, a highly vetted membership community for entrepreneurs, founders and CEOs. Throughout the interview, Parr shared his journey as an entrepreneur, from his early days selling hot dogs in Nashville to building and scaling The Hustle newsletter to millions of subscribers and a massive exit to Hubspot.

Parr's story is one of grit, hustle (pun intended), and strategic pivots. He candidly discussed his failures, like getting fired from Airbnb before even starting the job and underpricing his newsletter product, as well as his successes, such as building a passionate audience and cultivating a unique company culture. In this article, we'll dive into five key learnings from Parr's experience that aspiring entrepreneurs can apply to their own startup journeys.

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1. Master the art of the cold call/email to open doors and build relationships

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One of the most striking things about Sam Parr is his fearlessness when it comes to reaching out to people, whether it's potential customers, partners, or even celebrities. "I cold call people all the time. I still do that," Parr said in the interview. He shared a story about how he once cold emailed the founder of Airbnb, offering unsolicited advice on how to improve their website. His audacity led to a job offer with what would become one of the largest online marketplaces in the world. While that particular outreach didn't pan out (more on that in the interview), Parr's hustle mentality has served him well in building The Hustle and his subsequent ventures.

Parr's dedication to mastering the art of the cold call is evident in the unconventional tactics he used to hone his skills. Early on, he would open up the phone book and call random numbers, challenging himself to convince the person on the other end to recommend a movie for him to watch that night. “I would do that literally like a hundred times a day to like get over my fear,” he recollected in his interview. “That was a great exercise.” This practice helped him desensitize himself to rejection and refine his pitch.  While cold calling random people may not be the most efficient use of your time, the basic principle of desensitizing yourself to rejection and honing your pitch still applies.

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Parr also learned to use self-deprecation to his advantage, a technique he still employs today. When promoting his latest venture, Hampton, to a high-level executive, Parr opened the conversation by acknowledging the potential awkwardness of the situation: "Hey, this is a really weird call. And I'm so sorry for bothering you. And what I'm about to say sounds super douchey." By leading with vulnerability and humor, Parr was able to instantly disarm the executive and create a more human connection.

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Putting it into practice:

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Start small by reaching out to one person you admire each week, whether it's via email, Twitter, or LinkedIn. Focus on providing value upfront rather than immediately asking for something. For example, share an article or resource they might find helpful, or offer a thoughtful compliment on a recent project of theirs.

To dive deeper into the art of cold outreach, check out the book "How to Get a Meeting with Anyone" by Stu Heinecke or take a sales training course like "The Startup Sales Course" by Close.io.

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2. Hire quirky, passionate people and let them be themselves

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When it comes to building a successful startup team, Parr has a somewhat unconventional approach. "I hire weirdos," he said bluntly. He gave the example of Trong Phan, a former writer for The Hustle who now has over a million Twitter followers. "When we hired him, he didn't even have a Twitter." In our interview, Parr recounted why he hired such a unique personality in the first place, stating that he looks for people who are not only skilled in their craft, but also have unique perspectives and a genuine passion for their work. He shared his interview technique of focusing on "the bottom fourth of the resume" - the part where candidates list their interests and hobbies. "I would always ask them about like things like that or, uh, like a variety of questions for the bottom fourth of the resume. And that's like how I would find them."

Parr digs deep into this "bottom fourth" of the resume, using it as a window into a candidate's true passions and personality. He shared a favorite interview question: "What was the best class you studied in school, and why?" Parr believes that if someone has spent four years and hundreds of thousands of dollars on their education, they should be able to speak engagingly about what they learned and why it mattered to them. "If you couldn't entertain me about why you were passionate about this thing, I don't want to be around you. If you could capture my attention, and I could feel your passion about why you're interested in a topic, you got some juice in you and I want to know about it."

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In addition to probing candidates' passions, Parr also looks at the content they create and share online as a key part of his hiring process. He specifically mentioned being drawn to Steph Smith, a former Hustle writer who now works at Andreessen Horowitz, because of a blog post she wrote titled "How to Be Great? Just Be Good, Repeatably." Parr was so impressed by the piece that he reached out to Smith directly, even though she wasn't actively looking for a writing job at the time. By looking beyond just credentials and resumes and instead focusing on the ideas and creations that candidates put out into the world, Parr is able to identify uniquely talented and passionate individuals who might otherwise be overlooked.

But hiring passionate, quirky people is just the first step. Parr believes in creating a culture where employees feel comfortable expressing their full selves. "I had this joke at the office, I would say The Hustle is where you can let your freak flag fly." he recalled. Parr actively encourages his team members to embrace their weirdness and bring their whole selves to work. By cultivating an environment where individuality is celebrated rather than stifled, Parr believes that creative output and overall team performance are enhanced. As he put it, "We just did a really good job of pushing them and letting them be freaks."

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Putting it into practice:

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When hiring for your startup, don't just focus on credentials and hard skills. Look for candidates who have unique perspectives, diverse interests, and a genuine excitement for your mission.

In interviews, ask open-ended questions that allow candidates to share their passions and personality. For example: "What's the most interesting thing you've learned recently outside of work?" or "Tell me about a side project or hobby you're currently excited about."

Once you've built your team, foster a culture of psychological safety and self-expression. Encourage team members to share their ideas, even if they seem a bit "out there" at first. To learn more about building a strong startup culture, read "The Culture Code" by Daniel Coyle or check out the resources at CultureAmp.com.

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3. Focus on building one great product before expanding

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In the early days of a startup, it can be tempting to chase every shiny new opportunity that comes your way. But Parr cautions against spreading yourself too thin. "I focus a lot. People think that I don't." he emphasized. Parr believes that it's hard to do more than one thing well at a time, especially as a small startup team. Instead, he recommends going deep on one great product before expanding into adjacent areas. "I think about a ton of stuff and do all the research. But when I make a bet, I try to do it with a high degree of certainty that it can work."

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One area where Parr sees many early-stage startups getting distracted is in branding. While having a strong brand is undoubtedly important, Parr argues that it shouldn't come at the expense of building a great product. However, Parr is quick to point out that once you've achieved product-market fit and are ready to scale, investing in branding becomes crucial. He learned this lesson firsthand with his latest venture, Hampton. "Once I developed an audience and felt confident in my ability to execute, I realized you have to nail the brand and culture first. You've got to get it right early because it's a pain to go back and redo it."

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Putting it into practice:

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As you're building your startup, ruthlessly prioritize the features and initiatives that will have the biggest impact on your core product. Resist the urge to tack on bells and whistles before you've nailed the core value proposition.

Use frameworks like the Lean Startup methodology and the jobs-to-be-done theory to validate your product hypotheses and ensure you're building something people truly want. Focus on achieving product-market fit before worrying about scale.

Recommended resources: "The Lean Startup" by Eric Ries, "Hooked: How to Build Habit-Forming Products" by Nir Eyal, and the ProductPlan blog for product management best practices.

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4. Don't undervalue your product or target the wrong customers

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One of Parr's biggest regrets with the earlier parts of his career was underpricing the products he created in the early days. "When I started Trends, I was 27 and still kind of broke. I didn't imagine that businesses would pay a lot of money for things," he reflected. Parr admits he made the mistake of not putting himself in the customer's shoes and truly evaluating the value his product provided. In the interview, Parr elaborated on the thought process behind his pricing decisions. "I charged $300 a year for Trends. I should have charged $30,000 a year and sold it to companies. That was a massive mistake." He attributed this misstep to his lack of experience and understanding of the B2B market at the time. "I was in my late 20s and had never really sold to businesses before. I didn't realize how much value we were providing and how much companies were willing to pay for that kind of information."

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This pricing mistake had significant consequences for the business. "We were leaving so much money on the table. If we had priced it right from the beginning, we could have grown much faster and had a lot more resources to invest in the product and the team." Parr's experience with Trends taught him a valuable lesson about the importance of understanding your target customer and pricing your product accordingly - knowledge he has learned to leverage with his newest venture, Hampton, which puts a premium on creating an environment for entrepreneurs, founders, and CEOs to network and collaborate in private settings. 

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Putting it into practice:

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When setting pricing for your product, don't just pull a number out of thin air based on your gut feeling. Conduct thorough market research to understand how much value your product provides to customers and what comparable solutions cost. Talk to potential customers to uncover their willingness to pay and the key benefits they derive from your product. Consider value-based pricing rather than cost-plus pricing.

Make sure you're targeting the right customer segment for your product. Identify the customers who have the biggest pain point and the most to gain from your solution, and focus your marketing and sales efforts on reaching them. To learn more about pricing strategy, read "Monetizing Innovation" by Madhavan Ramanujam and Georg Tacke. For customer development and segmentation, read "The Lean Product Playbook" by Dan Olsen.

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Building a successful startup is never easy, but you can tilt the odds in your favor if you learn some of the basics that Sam Parr emphasized in our interview . For a start: Master the art of the cold call, hire passionate oddballs, focus on one great product, and make sure you're targeting the right customers at the right price.

Of course, this is just the tip of the iceberg when it comes to Parr's startup wisdom. To hear the full story of his entrepreneurial journey, including his early failures, his experience building and selling The Hustle, and his thoughts on the future of media and community, be sure to check out his episode on the Forward Obsessed podcast. It's well worth the listen.

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Now if you'll excuse me, we have some cold calls to make. Happy hustling!

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