Hot Dogs to Millions: The Wild Entrepreneurial Journey of Sam Parr

If you’re a fan of scrappy entrepreneurship tales, then grab a seat. This is the story of Sam Parr – a guy who went from hawking hot dogs on the streets to selling a media empire for eight figures, and then co-hosting one of the most popular business podcasts around.

Sam’s journey is anything but ordinary. It’s packed with quirky side hustles (think street-fight videos on YouTube and a hotdog stand with a hilariously outrageous name), bold leaps of faith, crushing setbacks, and big wins. And through it all, Sam has maintained a down-to-earth charm that makes his story as relatable as it is inspiring. In this casual deep-dive, we’ll walk through Sam Parr’s life – from his early days and first hustles, to building The Hustle newsletter, launching the My First Million podcast, and beyond.

Along the way, we’ll highlight the key lessons and philosophies that propelled him forward, and even share a few personal anecdotes (including how a blog post helped him meet his future wife!).

So, let’s jump in and see what we can learn (and be inspired!) from Sam’s ride from hot-dog carts to million-dollar exits.

Early Life: A Curious Kid from the Midwest

Sam Parr was born and raised in St. Louis, Missouri, in the American Midwest (men from here rock - cue my perfect husband from Minnesota!)​. From an early age, Sam had entrepreneurship in his blood – literally. His parents were both entrepreneurs, so he grew up thinking that starting businesses was just a normal way of making a living. That mindset, combined with an almost boundless curiosity, set the stage for Sam’s future ventures.

As a kid, he was known to pepper adults with questions – not just the usual “why is the sky blue?” variety, but business-savvy ones like asking his parents’ friends how much money they made or how they could afford their car​. Sam wasn’t trying to be rude; he was genuinely fascinated by how people become successful and the “mechanics of being great”​. He recalls being intensely interested in how things work – from how buildings are constructed, to who invented the air conditioner – and he realized early on that business often comes down to a simple formula: make something for a certain price and sell it for more​.

That insight might sound obvious, but for a young kid it was an eye-opening peek into the world of entrepreneurship.

Growing up, Sam was also a dedicated athlete. He was a talented runner – so good that he earned a NCAA Division-1 track scholarship for the 200m and 400m sprints at Belmont University in Nashville, Tennessee​. By his late teens, he moved from Missouri to Tennessee for college, balancing a rigorous athletics schedule with academics. But despite training on the track every day, Sam’s entrepreneurial itch never went away. In fact, it found new ways to express itself during his high school and college years.

Picture young Sam as that kid who was always up to some scheme or side project to make a buck (or just for the thrill of it). For instance, during his track days, he found a market for his used running gear – he would sell his old track shoes and uniforms on eBay and Craigslist​. Not exactly a Fortune 500 endeavor, but it taught him early on that there are customers for almost anything if you know where to look.

Sam also dabbled in the Wild West of online content in the late 2000s. In one particularly cheeky hustle, he started uploading “street fight” videos to YouTube – but with an interesting twist​. He noticed that when you typed “streetfight” into YouTube’s search, the autocomplete suggestions got oddly specific (one example he gave: it would suggest “black guy beats up white guy”). Sensing an opportunity, Sam began creating videos with sensational, clickbait titles matching those popular search terms. The videos themselves? Not actual fights, but basically just a still image (the thumbnail) with music playing in the background​.

It was a bit of a scammy tactic, sure, but it worked: the sensational titles drew clicks, and Sam monetized it by charging up-and-coming bands to feature their music in the background of these videos. In typical hustler fashion, teenage Sam found a way to turn even a fake streetfight video into a win-win – viewers got their “content” (albeit just a looping image with sound) and indie bands paid him for exposure.

Looking back, Sam openly admits this scheme was kind of sketchy, but it showcases a recurring theme in his life: resourcefulness. He had a knack for spotting unconventional ways to make money or get attention, a skill that would serve him well later on.

Beyond those early online antics, Sam’s first “real” business arrived while he was still in college. And yes, it involved hot dogs. Around 2010 (during his junior year at Belmont), Sam started a humble hot dog stand in Nashville. But of course, this wasn’t going to be just any hot dog stand – it had to stand out. Embracing his irreverent sense of humor, Sam gave his venture an unforgettable name: “Southern Sam’s: Wieners as Big as a Baby’s Arm.”​ (Take a moment to appreciate that imagery!).

The outrageous name was half marketing stunt, half reflection of Sam’s personality. “A hot dog is a commodity. They’re pretty much all the same,” he later explained, so he figured he needed a gimmick to differentiate. The “baby’s arm” slogan certainly turned heads, and Sam even devised a silly promo: if parents came by the stand and literally put mustard on their child’s arm (yes, really) to take a photo, he’d give them a free hot dog​.

Ridiculous? Absolutely.

But it got people talking. And more importantly, it got them buying. Southern Sam’s turned into a decent little business, reportedly pulling in up to $1,000 on good days with about 50% profit margins​. Not bad for a college side hustle selling $2 hot dogs!

Running the hot dog stand taught Sam some invaluable lessons in promotion and grit – shouting “All beef hotdogs!” on a street corner in the 99°F Nashville heat will do that​. He was out there grinding, chatting up strangers on the sidewalk, and figuring out first-hand what it takes to get customers one by one. In a later recollection, Sam described those days vividly: he’d spend hours under the sun, yelling out deals and bantering with passersby until he was sunburnt and exhausted​. It was tough work, but he loved the feeling of making something happen on his own. And amazingly, this was just one of his ventures at the time.

While slinging hot dogs, Sam also started an online liquor store during his senior year​ (near and dear to my own Sommelier heart!). He has said that between the hot dog stand and the liquor e-commerce business, he was able to pay his way through college. He’d be sitting in class and hear his phone go “ka-ching!” with each new order coming in for alcohol delivery – a pretty great distraction to have as a 21-year-old student​.

Eventually, as graduation neared, Sam realized he had the entrepreneurial momentum to skip the typical job route. So, in 2012 he made a bold decision: drop out of college a few credits shy of finishing and head west to Silicon Valley, hoping to break into the tech startup scene.

Little did he know, the next chapter of his life would test his resolve like never before.

From Hot Dogs to Silicon Valley: Taking the Leap

Armed with ambition (and perhaps a healthy dose of naïveté), Sam Parr landed in San Francisco in 2012 with big dreams of building an internet company​. He didn’t have a specific idea in mind; he just felt that San Francisco was where things were happening and he didn’t want to miss out. In fact, the move was triggered by an intriguing near-miss opportunity.

While still in Nashville, Sam had caught wind of a quirky startup called “Air Bed and Breakfast” – which, as you might guess, was the early incarnation of Airbnb​. Through sheer hustle, Sam managed to get the attention of Airbnb’s team. He cold-emailed the founders, praising their website and basically asking for a job interview​. To his surprise, they responded and invited him to come in. There was just one problem: Sam was not actually in San Francisco at the time – he was still finishing school in Tennessee​.

Minor detail, right? Rather than admit that, Sam bluffed that he was “in town” and could swing by the office, then immediately booked a flight to California. It was a ballsy move – the kind of do-whatever-it-takes maneuver that defines Sam’s style.

Amazingly, the bluff worked, at least initially. Sam flew out the next day and went in for the interview at Airbnb. In fact, the co-founder Joe Gebbia himself offered Sam a job on the spot​. It was a dream come true – until it suddenly wasn’t. Just days before his start date, Airbnb rescinded the offer.

Sam received a devastating call: during a background check, they discovered he’d lied about a recent run-in with the law​. (In college, Sam had gotten into some trouble related to drugs and alcohol, resulting in an arrest – something he tried to hide on the job application​.) When Airbnb found out, they told him in no uncertain terms: We can’t hire you. Sam was floored. He tried to explain that he thought the wording on the form was tricky (he hadn’t technically been convicted yet at the time, or so he thought), but Airbnb didn’t budge​.

Just like that, the golden opportunity vanished.

This was, in Sam’s own words, the “lowest point” of his life​. Imagine: he had dropped out of college, sold his stuff, moved across the country chasing a dream – only to end up jobless, almost broke, and alone in San Francisco. He remembers calling his parents in tears after the Airbnb fiasco, feeling like he’d hit rock bottom​. His mom was crying too, worried for her son who had rolled the dice and seemingly lost. For a brief moment, it looked like the end of the road.

But if there’s one thing to know about Sam Parr, it’s that he doesn’t stay down for long. That crushing experience became a turning point. Sam resolved then and there to clean up his act and double down on building a life he could be proud of​. He swore off alcohol and any substances (and indeed, he’s been sober ever since) and decided to make the most of being in Silicon Valley even without a job waiting​.

It was time to hustle from scratch.

Stranded in San Francisco, Sam did two things that would prove pivotal: network like crazy and team up on a tiny startup. First, to meet people and learn, he started a sort of informal book club for ambitious folks, cheekily named “The Anti-MBA.”​ Each week, he’d gather people to talk about business books and invite local entrepreneurs to speak. It was free to attend – the whole point was to build connections (and, perhaps, show those Stanford MBA-types that you could self-educate just fine).

This book club not only expanded Sam’s knowledge (he read dozens of biographies and business books during that time), but also plugged him into a valuable network of founders and mentors​. In fact, Sam credits this period – hosting events, blogging about what he learned, meeting new people constantly – as the foundation that later enabled his success​.

Second, Sam caught a lucky break through an unlikely roommate situation. While couch-surfing and apartment hunting, he met a web designer named John Havel who happened to be working on a startup idea: a roommate-matching app called Bunk. The concept was like “Tinder for roommates,” letting you swipe on potential roomies – a quirky idea, but interesting enough​. Sam immediately saw this as a chance to break into startups. He basically invited himself to join John’s project, pitching himself as a co-founder who could help grow it​. John said yes, and suddenly Sam had a foothold in the startup world.

Bunk was a modest venture – they spent about 10 months building this roommate-finder app in 2012–2013​. It was far from a runaway success, but it did well enough to get acquired by a company called Apartment List for a small sum (reportedly $15,000)​. That’s not life-changing money, but for Sam, even a tiny exit was validation. He was now officially a tech entrepreneur with a real win under his belt. Plus, as part of the deal, he got a one-year job at the acquiring company, which paid about $100K over that year​ – finally providing some financial stability after the turbulence of his arrival in California!

By mid-2014, with the Bunk chapter closed (and a business degree completed as well – Sam managed to finish his remaining college credits online to formally graduate​), Sam found himself at a crossroads. He had a bit of cash, a lot of new knowledge, and endless enthusiasm to do something big. But what would that something be? It was time for the next big idea. As fate would have it, that idea would start out as a small event – almost an experiment – that would eventually snowball into the media empire known as The Hustle.

Hustle Con: An “Accidental” Business Launch

Fresh out of his first startup experience, Sam wasn’t entirely sure what to do next. He often says he was looking for his “Thing” – the big, passion-fueled project he could pour himself into​. His strategy? Stay busy and put himself in the path of opportunity.

So, in 2014, Sam decided to organize a one-day event for entrepreneurs. He called it Hustle Con, and in his mind it was just a fun side project – maybe it would spark an idea or connect him to someone who had one​. As Sam later put it, “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.”

Little did he know, Hustle Con would become the springboard for his future company.

Hustle Con was envisioned as a startup conference for non-techies – basically, a day of talks where founders of successful companies share practical advice, TED-style, but geared towards people who wanted to build businesses without necessarily being engineers or coders. Sam got the inspiration because he admired TEDx conferences but couldn’t afford the steep ticket prices as a scrappy twenty-something year old (the main TED conference can cost thousands)​.

So, he thought, why not create a more accessible version? He often jokes that he started Hustle Con because he was “too poor to attend” the fancy conferences, so he made his own.

Now, organizing a conference from scratch in a matter of weeks is no small feat – especially for someone with no experience doing it. But Sam approached it with his trademark hustle. He leveraged every connection he had (and many he didn’t yet have) to line up speakers and sponsors in a short time frame​. In fact, he managed to put together the entire event in just 6 or 7 weeks​. He set a date (July 2014) and without overthinking it, announced the event publicly before everything was even in place – committing himself to figure out the details on the fly​.

This “announce now, build as you go” approach is classic Sam Parr. It forced him to hustle hard to avoid embarrassment, and it worked.

To drum up attendees, Sam got creative (yet again). He started blogging and sending emails to promote Hustle Con – writing about the speakers, sharing tips, posting on social media and even Reddit. He had that small network email list of ~300 people from his friend Erik (more on that in a second), and he began to grow it by publishing engaging content about the upcoming event.

Here’s a fun fact: Sam didn’t actually come up with the name Hustle Con himself. He met two early-stage investors (Erik Bahn and Elizabeth Yin) in San Francisco who had thought about doing an event with that name and even had a tiny mailing list for it​. They weren’t using it, so when Sam mentioned he was looking for his next move, they basically said, “Hey, we have this name Hustle Con and a list of 300 emails. Want to do something with it?”.

Sam’s response: absolutely yes. It was the perfect banner to run with.

Hustle Con’s first event absolutely smashed Sam’s expectations. Thanks to a whirlwind of promotion and likely Sam’s infectious enthusiasm, the inaugural conference in 2014 sold around 400 tickets and made roughly $60,000 in profit​. (Sam himself said he thought it wasn’t going to work – that it’d just be a way to meet someone to start a company with – but to his surprise, “it worked”​.) Suddenly, what was supposed to be a side project became a profitable business in its own right. Encouraged, Sam did it again the next year. The second Hustle Con (2015) was even bigger: reportedly $250,000 in profit from that one-day event​. This little “time-killing” idea had momentum!

However, despite the success, Sam realized something important about himself: he didn’t love the conference business model.

Hustle Con was great, but running events is stressful. As he vividly described, “All the revenue comes in the last two weeks. It’s incredibly stressful. It’s kind of like training for a marathon. It sucks. It sucks. It sucks. Then you’re 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.”​ That tongue-in-cheek rant captures it perfectly – even when an event is successful, the process can be a nail-biter, since you often don’t know if you’ll break even until just before showtime. As someone who has been in hospitality for almost 2 decades now, this is exactly how event planning feels.

So while Hustle Con was bringing in cash and drawing crowds, Sam didn’t see it as The Thing he wanted to scale long-term. But something else did catch his attention: the newsletter and blog content he had been creating to promote the event was getting a life of its own. People were emailing him saying, “I love these stories you’re writing – they’re hilarious and insightful.”​ In fact, many attendees said they came to Hustle Con because they enjoyed reading the emails Sam sent out in advance​.

This planted a crucial seed in Sam’s mind. Maybe, he thought, the content is the real gold here, not the conference itself. As Sam later put it, “I realized producing the event wasn’t ‘The Thing’ for me, but writing the content that drove its attendance could be. ... I thought, ‘Well, maybe this [newsletter] is The Thing.’”​​ This lightbulb moment would lead directly to the birth of The Hustle as a media company.

Before we move on, it’s worth noting how serendipitous this all was.

Sam started Hustle Con almost on a lark, and it just so happened to give him the idea and initial audience for what became his flagship venture.

It’s a great example of a philosophy Sam often preaches: do things, even if they aren’t perfect or the ultimate goal, because action creates opportunity. By taking action with Hustle Con – even not knowing where it would lead – he stumbled upon a much bigger opportunity.

And he was smart enough to pivot when he saw that opening.

Building “The Hustle”: From Newsletter to Media Empire

In mid-2015, fresh off the success of Hustle Con, Sam decided to formally launch The Hustle – not as another event, but as a digital media brand. At the core of it was a simple idea: a newsletter that delivers business and tech news with an irreverent, bold voice that young professionals actually enjoy reading. Sam had noticed that existing business news was often dry or stuffy, and he wanted The Hustle to feel like a savvy friend emailing you a little summary of the day’s news, with a dose of humor and attitude. The tagline was “bold, irreverent, and authentic,” and the style was often likened to a mix between BuzzFeed and The New York Times, with a bit of Vice-like edge.

In short, The Hustle aimed to make serious news fun. Who doesn’t need more of this? Especially today.

But Rome wasn’t built in a day, and neither was The Hustle. In the very beginning (late 2015), it was just Sam writing random blog posts and email blasts a few times a week. These weren’t yet the polished daily news digests; they were more like long-form articles or experiments to find out what content would hit. True to Sam’s style, many early stories were outrageous or provocative to grab attention.

For example, one piece detailed how Pandora’s founder convinced employees to work for free (which got people talking), and another exposed a guy making $50,000 a month selling plagiarized “pickup artist” books on Amazon​. Sam even wrote first-person stunt stories like an account of taking LSD to treat depression (under a pseudonym) and an experiment where he lived off nothing but Soylent for a month​. These kinds of headlines were tailor-made for virality – perfect for sharing on Reddit or social media, which Sam did deliberately. He would often post his content on Reddit with catchy titles to spark huge threads.

The strategy was clear: create viral hits to grow the audience.

One funny tactic Sam employed was creating fake personas as authors for some articles​. Since The Hustle was a tiny operation (basically just him and maybe a friend helping), he invented characters with names like “Steve Garcia” and “Steph Whitfield” to write opinion pieces from different perspectives​. He even went so far as making LinkedIn profiles for these fictional writers, just to make it all look legit​.

In reality, Sam was writing most of it, but using alter egos allowed him to cover a range of voices and topics as if he had a whole team of reporters. When people later asked if this was disingenuous, Sam half-defended the practice, saying the stories were still truthful (they were based on real tips or experiences from others), he just delivered them through colorful characters​.

Sneaky? Yes. Effective? Also yes.

This hustle (pun intended) got The Hustle off the ground in its early months.

Within a year or so, The Hustle’s newsletter picked up tens of thousands of subscribers. Sam’s initial readers – many acquired through the Hustle Con event and those viral posts – loved the fresh voice and started sharing it with friends. By late 2015, he had about 75,000 – 80,000 subscribers, which was enough to attract the interest of advertisers​. The first sponsors were friendly companies, often run by founders who had spoken at Hustle Con or were in Sam’s network, and they paid roughly $1,000 for ad placements in the emails​.

This meant The Hustle was making money early on, a rarity in media startups. Sam also raised some outside capital – around $800,000 from angel investors – to give the venture more runway​. Impressively, he convinced some big-name angels to back him: the roster included the likes of Tim Ferriss (of 4-Hour Workweek fame), who chipped in, as well as founders of Bleacher Report and Wired, and even early Uber investor Scott Belsky​.

These high-profile supporters believed in Sam’s vision for a new kind of media company. Later on, The Hustle even did a brief crowdfunding campaign when it hit 200,000 subscribers – Sam opened up investment to readers, thinking maybe they’d raise $150K in a few months; instead they pulled in $350K in 48 hours​. (Sam admitted they didn’t really need that money at the time, but he loved that it got readers literally invested. Plus, as he noted, “Tim Ferriss, who gave me money, is now my friend and I can text him for advice. That is a cool trade-off.”​)

Despite early wins, by 2016 Sam faced a critical choice: stick with sporadic wild stories or evolve into a more stable, daily news source.

Chasing viral hits was exhausting and unpredictable – you never knew which crazy story would blow up and which would flop. Sam realized that to keep growing, The Hustle needed to become something people relied on, not just a source of occasional entertainment​. He was inspired in part by another successful newsletter, theSkimm, which was delivering daily news in a voicey, female-centric way and had amassed millions of readers by then​.

Seeing that model, Sam decided to pivot The Hustle in May 2016 to a daily newsletter format focused on the latest business and tech news – still served with a side of attitude and fun analogies​. “I thought, if we create news that people can rely on every single day, more people are going to engage with us,” he said of this crucial strategy shift​.

The pivot worked spectacularly. Once The Hustle rebranded as a daily news email (with the tagline “business and tech in 5 minutes” or similar), its growth exploded. By the end of 2016 (year one of daily operation), The Hustle had about 100,000 subscribers​. By the next year, around 2017, it hit 500,000. And by 2018-2019, it crossed the one million subscriber mark​.

Think about that for a second: in roughly three years, Sam went from zero to 1 million+ readers – all largely via word-of-mouth and clever content marketing, without huge VC money or a corporate media machine. The Hustle became one of the fastest-growing email media startups in the country​, serving a young professional audience hungry for a fresh take on news.

With growth came opportunities to expand. Sam and his small team (The Hustle grew to have a full staff of writers and salespeople) didn’t just stop at the free newsletter. In June 2019, they launched Trends, a paid subscription product for premium research and insights​. Trends was aimed at entrepreneurs and investors looking for the “next big thing” – it offered deep-dive reports on emerging industries and business ideas. This move added a nice stream of recurring revenue to The Hustle’s model, making the company less reliant on advertising alone. Sam had a knack for community-building, so Trends also included access to a private community where members could swap ideas. It was essentially monetizing the super-fans, and it worked well.

By the end of 2019, Sam’s little newsletter venture had blossomed into a multifaceted media business – daily news, events (Hustle Con was still held annually and growing, with thousands attending by 2019), and premium content. They reportedly had ambitions (at least Sam’s personal goal) of reaching $100 million in annual revenue by 2025​. Sam wasn’t shy about thinking big.

He even tweeted out his lofty revenue goals, which he kept as a motivator for the team​. The Hustle’s distinctive voice and direct connection with its audience proved to be a major asset. Sam often said he avoided building the business on social media platforms too much, because depending on algorithms is like “building a business in a rented apartment where the landlord can raise the rent any time.”​

He focused on owning the audience relationship directly via email, which gave The Hustle a stability many media startups lack​. This philosophy of independence (no reliance on Facebook or Twitter traffic) was forward-thinking, and it paid off when algorithm changes later hurt a lot of other media sites. Sam proudly kept The Hustle mostly bootstrapped, only raising that angel round and a small reader round – no big VC funds – which meant he maintained control.

As The Hustle grew, Sam’s role naturally evolved into that of a CEO managing a team. And while he excelled at setting vision and hustling for growth, the day-to-day management began to wear on him. By 2020, Sam found himself, in his own words, “being a business person” more than a creator, and feeling “worn out”​.

He has a self-deprecating way of saying that he’s not actually a great traditional businessman, that he’s more of an “artist” type when it comes to entrepreneurship​. He loves to start and build things, but meetings, org charts, and operational details drain him (don’t blame him!). With The Hustle’s success came a lot of those responsibilities. By late 2020, Sam was actually considering finding someone to take over as CEO so he could step back into a more creative role.

Then, the HubSpot offer came along and changed everything.

The Big Exit: Selling The Hustle to HubSpot

In late 2020, Sam received an email that would mark the beginning of the end (or rather, the start of a new chapter) for The Hustle. It was from HubSpot, the marketing software giant. Initially, HubSpot’s email was vague – they said they wanted to discuss a potential “partnership”​. Sam, being a straight-shooter, cut to the chase: “Just tell me, are you trying to buy us? Because if you are, maybe we can talk. If not, don’t waste my time.”​HubSpot responded that, yes, acquisition was indeed what they had in mind.

That got Sam’s attention.

Rather than play coy, Sam leaned fully into transparency during the negotiation. In what might be one of the most Sam Parr moves ever, he literally emailed HubSpot a bullet-point list of every reason The Hustle sucked and every reason it was awesome​. He laid out the warts and weaknesses – essentially presenting HubSpot a frank risk assessment of his company – alongside the strengths and potential synergy. He figured there was no point in hiding the negatives; if this was going to work, the buyer should accept all of it. HubSpot, to his surprise, came back and basically said, “Cool, we’re fine with all that.”​ That candid approach likely sped up the process and built trust.

By early 2021, they struck a deal. In February 2021, HubSpot officially acquired The Hustle. The terms, as reported later, were around $27 million total value​. Sam himself confirmed it was an eight-figure deal comprising $17.2 million in cash (per HubSpot’s SEC filing) plus a chunk of HubSpot stock that brought the total north of $20 million​. And funnily enough, the HubSpot shares that Sam received doubled in value shortly after, effectively making the sale even sweeter for him.

Not bad for a business he started with just a few thousand dollars and a lot of hustle.

The acquisition made a lot of sense on both sides. HubSpot was building out a media arm (they later launched HubSpot Media), and The Hustle’s content was a perfect fit to draw in the kind of small-business audience HubSpot covets. For Sam, it was a chance to take chips off the table and finally get a bit of relief from the grind of running a fast-growing startup. He had been at it non-stop for about 6-7 years.

The sale allowed him to hand over the reins. After the acquisition, Sam stayed on in a limited capacity – he continued hosting My First Million (which HubSpot also picked up as part of the media portfolio) and did some advisory work, but he was no longer in charge of managing The Hustle’s newsletter or team​. He basically achieved what every startup founder dreams of: an exit that both rewards you financially and lets you step back while your creation lives on.

Emotionally, selling The Hustle was a big deal for Sam. He has candidly talked about how it changed his life. One colorful quote: “When I sold, I was like a person with poor eyesight who put on glasses and saw the world differently... I was like, ‘Oh my God, living is so wonderful! ... I just felt great.’”​ In other words, the sale lifted a huge weight off his shoulders. Financial freedom and the absence of constant startup stress allowed him to enjoy life in a way he hadn’t before. After years of grinding, he could finally breathe and even indulge a bit – though knowing Sam, “indulging” probably meant immediately scheming his next project rather than sipping cocktails on a beach for long.

One immediate effect of the sale: Sam and his longtime girlfriend Sara (now his wife) decided to make some life moves. They had been living in San Francisco, then tried out New York City for a while, but ultimately relocated to Austin, Texas (which in recent years has become a hotspot for entrepreneurs)​.

Sam and Sara bought a house there in late 2021, settling into a city with a growing tech and startup community, but a more laid-back vibe than the Bay Area. This move was also partly motivated by personal goals: Sam had mentioned that after selling, he was looking forward to starting a family​. In fact, not long after, Sam and Sara got married and, as of late 2023, welcomed their first child (making Sam a proud new dad!). It’s a pretty big life change – going from all startup all the time, to suddenly having the flexibility to focus on family and new interests.

But don’t think for a second that Sam Parr just rode off into the sunset. True to form, he didn’t stay idle for long after The Hustle. By 2022, he was already plotting his next venture: Hampton.

Hampton is a private, highly-vetted entrepreneurs’ community (Sam calls it a “mastermind” network) designed for founders and CEOs of fast-growing companies​. Essentially, it’s like a support group meets brain trust for people running businesses, allowing them to share advice, experiences, and connections in a confidential setting. If that concept sounds a bit like something millionaire entrepreneurs would come up with after they exit a company – well, it is!

And it’s actually been quite successful out of the gate. Sam launched Hampton in early 2023 and it quickly attracted hundreds of members, including some big-name founders. It’s a business that plays to Sam’s strengths: community building, creating value through networking, and of course, a subscription model (members pay dues). In a way, Hampton circles back to those “Anti-MBA” book club days, but on a much larger scale and for a different audience.

Sam also started another project called Sam’s List, which is a forum/directory to help people find accountants and financial professionals​. That one seems a bit more niche – basically a product scratching an itch he saw among business owners (perhaps born out of discussions in Hampton). It’s clear that Sam just loves building things and solving problems he encounters.

Money wasn’t the main driver anymore (he already secured a life-changing sum), but the thrill of entrepreneurship keeps him coming back.

Through all these changes, one thing remained a constant passion for Sam: My First Million, the podcast he co-hosts. In fact, the podcast deserves its own section in this story, because it’s been a huge part of Sam’s journey and brand in recent years. So let’s rewind a bit to see how that came about and how it rose to prominence.

“My First Million”: Podcasting His Way to Popularity

Sam Parr is widely known not just as “the Hustle guy,” but also as one half of My First Million – a hit podcast he co-hosts with his friend (and fellow entrepreneur) Shaan Puri (I’ll write about Shaan next week, still researching!). The podcast’s concept is simple and addictively entertaining: Sam and Shaan brainstorm business ideas, riff on trends, and swap stories about entrepreneurship. Sometimes they bring on guests who have interesting business stories, but more often it’s just the two of them bantering and ideating.

Think of it as eavesdropping on two sharp, slightly goofy business minds as they scheme “the next million-dollar idea.” It’s light, it’s insightful, and it’s often funny – which has made it a top-ranked business podcast.

The origins of My First Million trace back to 2019. By that point, Shaan Puri (who had sold his own startup, Bebo, and was working at Twitch) and Sam had become friends in Silicon Valley’s small circle of young entrepreneurs. They both had this habit of meeting interesting people just out of personal curiosity – whether it was a guy who built a $100M real estate portfolio or someone who’d been a spy for the CIA​.

Sam and Shaan would invite these folks to coffee or their office and pepper them with questions, essentially doing informal interviews for fun. One day, Shaan suggested, “Hey, why don’t we record these chats and put them out as a podcast?”​. Sam was game, and thus My First Million was born as part of The Hustle’s content lineup in late 2019​.

In the early days, the podcast struggled to find an audience. It’s heartening to know that even guys with large followings and a media company behind them don’t always get overnight success in podcasting.

Sam mentioned that the very first episode had about 60,000 downloads, likely because The Hustle promoted it heavily to newsletter subscribers out of the gate, but after that initial curiosity, the numbers dropped to like 10,000 downloads per episode (or even less) for a while. Growing it beyond a niche was tough. Sam called it one of the hardest challenges he’s faced – harder, in some ways, than growing the newsletter​.

Why? Because podcasts are a slow burn; discovery is difficult, and you’re asking people for a lot of their time. But Sam and Shaan committed to making it work. They cranked out two to three episodes every single week for years​. That consistency – and their on-air chemistry – eventually paid off.

By 2021, as more people found the show (often through word-of-mouth or cross-promotion), My First Million started climbing the charts. This is around the time my friend Courtney sent it to me, and I have listened to every episode since! It has a kind of cult following among aspiring founders and business junkies who love the off-the-cuff idea sessions and the hosts’ energetic optimism about opportunities everywhere.

The format also evolved: initially they did more interviews, but some turning point came when a guest canceled last-minute and Sam and Shaan just did the episode with no guest, talking about ideas they had and recent news​. Listeners loved the hosts-only format even more. So they leaned into that, making most episodes just the two of them (with the occasional guest for a special treat). This set them apart from the bazillion other interview podcasts and let their unique personalities shine.

As of today (2025), My First Million is a bonafide hit. The show gets millions of listens each month across platforms​, and its YouTube channel (where they post video highlights) has blown up too, sometimes reaching entirely new audiences who prefer video clips.

It’s not uncommon to see episodes trend on Apple’s business podcast charts. The show has also attracted high-profile guests for the special episodes – everyone from tech billionaires to celebrity investors have dropped in. But perhaps more tellingly, Sam and Shaan themselves have become mini-celebrities in the startup world. They have over 300,000 followers each on X (Twitter) where they often discuss topics from the pod, and fans eagerly discuss episode takeaways on forums and even a dedicated My First Million Discord community.

For Sam, the podcast has been a fantastic platform to share his philosophies and to keep doing what he loves: talking about businesses. You can hear the joy in his voice when an idea excites him or when he’s joking about some oddball scheme (like the time they debated the merits of a hypothetical cat restaurant business). And because it’s in a casual, conversational format, listeners get to know Sam on a personal level – complete with his humor, occasional rants, and the way he says “dude” a lot.

In a sense, My First Million has helped cement the Sam Parr brand beyond The Hustle. It shows him not just as a media founder, but as a thinker, investor, and entertainer in the business space.

Interestingly, hosting the podcast also reinforced some of Sam’s beliefs about content and consistency. As mentioned, he discovered that there’s no shortcut other than putting in the work week after week. For the first year or more, growth was slow, but they kept the faith. Sam has said the persistence with the podcast – releasing new episodes every Monday/Thursday without fail – is what eventually unlocked big growth​. There’s a lesson in that for creators: you have to love the process enough to stick with it before the big audience shows up.

Today, Sam continues to host My First Million twice a week, even as he juggles his new startups and being a new father. The podcast, now under the HubSpot Media umbrella, is a core part of his life. And thanks to its success, Sam Parr’s voice (figuratively and literally) reaches a far wider audience than even The Hustle did at its peak. It’s pretty cool to see, considering the show started as two friends recording conversations on a lark.

Speaking of Sam’s voice and perspectives – let’s delve into what underpins all these adventures. What philosophies and values drive a man to do all this weird and wonderful stuff? From college hustles to big business deals, Sam has picked up a wealth of insights.

Next we’ll explore some of the key lessons and personal philosophies Sam has shared over the years, which might just be the most valuable takeaways from his journey!

Personal Life & Values: The Man Behind the Hustle

Amidst all the hustle (pun intended), Sam Parr’s personal life and values have played a huge role in shaping who he is and how he operates. We’ve touched on some of this already – like his decision to become sober after that early setback – but let’s paint a fuller picture of Sam beyond the businesses.

First and foremost, Sam is guided by an intense curiosity and love of learning.

He’s a self-professed history and book nerd. Even when he was grinding on The Hustle, he made time for reading biographies and non-fiction to glean lessons from great leaders and innovators. Reportedly, he’s read over 60 biographies of notable people, and he would even jot down timelines of when those people started their ventures versus when they achieved success​.

That long-term perspective taught him that overnight success is a myth – most “sudden” successes actually come from years of groundwork. Sam often mentions historical figures as inspirations: he admires John D. Rockefeller for being both a ruthless businessman and a calm, family-oriented guy. He’s fascinated by bold explorers like Lewis and Clark or surfer Laird Hamilton – people who push boundaries and dare to try audacious things​. The Wright Brothers are another favorite example of his; he finds it “incredibly courageous” how two unknown bicycle mechanics from Ohio believed they could invent the airplane, and then did​.

To Sam, stories like that are “freaking cool” and embody the kind of confidence and audacity he aspires to​. He even follows modern-day heroes like Neeraj Chopra, an Olympic gold medalist from India who rose from humble beginnings (honestly, he just seems to really like buff guys too, he’d love my husband!) – Sam loves a good underdog-to-winner story​. All this is to say, the guy is a sponge for knowledge and inspiration. He actively channels these lessons from books and history into his own life, whether it’s how he runs a company or how he takes personal risks.

On a values level, one thing that stands out about Sam is his emphasis on authenticity and independence.

He’s not one to put on airs. In fact, part of The Hustle’s brand was basically Sam’s own personality writ large – informal, sometimes irreverent, but always real. He hates overly “corporate” vibes. This extends to how he built his business (keeping it independent of big tech platforms’ whims) and how he interacts on social media (often joking and being candid about failures).

Sam also values hard work, but not in the generic “grind 24/7” way – more like, if you’re going to do something, really commit and be consistent. We saw that with how he tackled the podcast slog, or how he wrote the newsletter every single day without fail for years. He’s quoted as saying, “You can wing it and I think you should wing it... I don’t project five years out... I have a vague vision of the future, but I’m going to zig and zag every single day and figure it out as I go.”​. That captures a bit of his philosophy: you don’t need a perfect plan to start (wing it), but you do need to take action daily (zig and zag consistently) and adjust course over time.

In other words, just start, keep moving, and trust yourself to adapt. A philosophy I agree wholeheartedly with.

Sam’s personal life also saw a wonderful development that he likes to joke about: he met his wife, Sara, because of his blog. Yes, really. Back around 2013, after his cross-country motorcycle trip (did we mention he once motorbiked across America after Hustle Con? Because he did – just for adventure), Sam wrote about that journey on The Anti-MBA blog and some publications picked up the story​.

Sara read about this cool guy riding around the country and thought it was interesting. They eventually connected (Sara even had bought one of Sam’s Craigslist apartment-finding guide PDFs before they met – talk about a meet-cute for entrepreneurs!)​. One thing led to another, and they started dating​.

It’s like a modern entrepreneur fairy tale: girl reads blog, meets boy, boy sells startup for $27M, they live happily ever after.

In all seriousness, Sam often gives credit to Sara for grounding him and bringing happiness outside of work. They got married in 2022 (Sam cheekily mentioned on Twitter how they literally sat down and negotiated their marriage terms upfront – ever the practical thinker)​. And as noted, they just welcomed a baby in late 2023, which Sam proudly shared on Instagram with a big smile. Fatherhood was something he had been looking forward to (“I want to have kids” he said after selling​), and now that’s a reality.

It’s a new chapter that’s certainly changing his daily routine – fewer late-night brainstorm sessions, more early-morning diaper changes!

Speaking of routines, Sam’s day-to-day habits have evolved. In the height of The Hustle grind, he was known to wake up very early, crank out writing, hit the gym (fitness is still important to him from his track days), and consume information voraciously. He’s not shy about saying he hires trainers or coaches for accountability – he approaches personal goals with the same “system” mindset as business goals. And remember, he’s completely sober now – he quit drinking in his early 20s after that wake-up call with Airbnb and hasn’t touched alcohol or drugs since​.

Instead, he channels energy into hobbies like reading, fitness, and lately, being an outdoor enthusiast (Texas offers good hiking, and he still rides his motorcycle now and then). The sobriety decision is a core part of his story; he’s mentioned how getting sober changed his life for the better, giving him the clarity and focus to achieve what he has​.

Another personal trait: Sam is incredibly open about seeking advice.

He’s always asking questions and learning from others – a humility that perhaps comes from that childhood curiosity. He cultivated mentors like Neville Medhora (a famous copywriter/blogger) early on, which helped him refine his content skills​. He’s also unafraid to admit what he’s not good at. For example, when The Hustle started making decent money (~$300K in the first year, he said​), Sam realized that even if he didn’t love writing per se, he was good at content and it could pay the bills, so he “would be an idiot not to pursue it”​.

That pragmatism – doing what works and not just what your ego wants – is a valuable insight into his mindset.

Finally, in terms of values, Sam strongly believes in networking and community (which explains Hampton).

He often says the best opportunities in his life came from talking to people, being out there, and sharing ideas. His whole career arguably started because he wasn’t afraid to email strangers like Airbnb’s founders or chat up a random designer who became his co-founder. Even The Hustle’s growth was community-driven – he fostered a sense of belonging among readers (inside jokes, referring to readers as “Hustle” family, etc.) that made them stick around. Sam seems to genuinely enjoy connecting people and seeing them succeed too. That’s why Hampton isn’t surprising as his new project: he finds joy in facilitating others’ growth as well.

In summary, the man behind the media persona is someone who is curious, bold, and hardworking, yet also reflective and values-driven. He’s not all about the money (after all, he basically “retired” at 31 with more than $20M​ but jumped right back into building new things). For Sam, entrepreneurship is as much sport and creative outlet as it is livelihood. His journey shows that success isn’t just about one big idea – it’s the culmination of consistent small actions, learning from failures, staying true to yourself, and taking chances when opportunities knock. And importantly, he’s balanced that with building a fulfilling personal life, which keeps him happy and sane.

Now that we’ve traversed the winding road of Sam Parr’s story, let’s distill a few key takeaways from his life and career. There are plenty of lessons aspiring entrepreneurs (or anyone, really) can draw from this tale of hot dogs, hustle, and beyond.

Sam Parr’s Playbook: Key Lessons from a Life of Hustle

Sam’s journey is full of teachable moments. Here are some of the big philosophies and lessons that emerge from his story:

• 1. Start something – action breeds opportunity: Sam didn’t always know his ultimate path (far from it), but he jumped into projects that interested him, from a hot dog stand to a book club. Each venture – even the small ones – taught him skills and led to connections that opened the next door. Lesson: Don’t wait for the “perfect” idea; start with small hustles and experiments, because you never know where they’ll lead​.

• 2. Be ridiculously resourceful: Whether it was selling used shoes online or creating fake reporter personas for his newsletter, Sam mastered the art of doing more with less. He leveraged free channels (Craigslist, Facebook, Reddit) and clever hacks to grow his businesses on a shoestring budget. Lesson: Creativity beats big budgets. If you’re scrappy and think outside the box, you can gain traction without needing a ton of money or resources​.

• 3. Learn from lows and keep moving forward: Getting a dream job offer yanked away due to his own mistake could have broken Sam. Instead, he calls it one of the best things that happened – it pushed him to get sober and build his own thing​. He didn’t dwell on failure; he transformed it into motivation. Lesson: When you hit a low point, extract the lesson, make a change, and use it as fuel rather than giving up.

• 4. Build an audience before you need it: A huge part of The Hustle’s success was that Sam had been building an audience through Hustle Con and blogging even prior to launching the newsletter. When he flipped the switch, he already had eager readers. Lesson: Audience is everything – nurture followers by providing value (content, events, communities) and they’ll be there to support your ventures when you launch.

• 5. Don’t be afraid to pivot when something isn’t working: Sam could have kept running Hustle Con events and one-off viral blogs, but he recognized the need to change course. He bravely shifted The Hustle’s format (from sporadic articles to a daily news email) and its business model (introducing a paid product with Trends) when he saw better opportunities​. Lesson: Stay flexible. Pivot quickly if you find a more viable strategy or if your current approach isn’t scalable.

• 6. Consistency + patience = growth: The My First Million podcast’s rise illustrates this well. It didn’t explode overnight; Sam and Shaan stuck to a thrice-weekly schedule for two years before it really caught on​. Likewise, The Hustle’s daily grind of writing built trust over time. Lesson: Show up regularly and give things time to compound. In content, business, or fitness – the unsexy consistency often yields the sexiest results.

• 7. Authenticity wins (and it’s easier on the soul): One reason people love Sam (and his products) is the authentic voice. He’s not trying to be someone he’s not. The Hustle’s tone was basically Sam’s humor and candor at scale​. He’s transparent with his audience (even about the company’s flaws during the HubSpot deal)​. Lesson: Be real. It builds trust and sets you apart in a world full of corporate-speak. Plus, life is too short to pretend – as Sam learned, honesty (with yourself and others) is freeing.

• 8. Know your strengths (and weaknesses): Sam recognized that he loves creating and hates long meetings. He’s an idea person and a marketer at heart, not a spreadsheets guy – so he engineered his career to fit that, whether by planning to hire a CEO or eventually selling the company​. Lesson: Self-awareness is key. Figure out what you’re good at and enjoy, and structure your business or role to maximize that. Get help or exit when you’re spending most of your time on things that drain you.

• 9. Invest in relationships and community: From his college days networking with Mike Wolfe of American Pickers to raising money from Tim Ferriss to co-founding Hampton, Sam has leveraged and given back to his network constantly​. He’s a connector. Lesson: Relationships are the real currency. Help others, stay in touch, and put yourself out there. Opportunities often come via people, not just ideas.

• 10. Keep your priorities straight: Finally, Sam’s journey underscores the importance of personal well-being and happiness. He built a company called Hustle, yes, but he also chose sobriety, prioritizes family, and eventually cashed out when the time felt right to focus on life. He even moved out of the SF rat race to a calmer Austin life for a better balance. Lesson: “Hustle” doesn’t mean burn out. Work hard but make choices that serve your life, not just your business. Success is as much about enjoying the ride as it is about the destination.

As Sam might say, those are the main bullet points he’d jot on a napkin if you asked him for advice.

His story is proof that there’s no single formula for entrepreneurship – it’s messy, unpredictable, and often ridiculously fun if you embrace the twists and turns. From selling baby-arm-sized hotdogs to signing a multimillion-dollar deal with a tech giant, Sam Parr has shown that ambition, grit, and a good sense of humor can take you a long way in the world of business.

In Sam’s own life, this isn’t the end of the story – at just 35 years old, he’s now running new ventures, continuing to spin out ideas on My First Million, and raising a family. You get the sense that he’s just getting started on another chapter of adventures, armed with the lessons of the past and the enthusiasm of a newbie entrepreneur. And for those of us following along, the ride is sure to be educational and entertaining in equal measure.

So here’s to Sam Parr – a true hustler (in the best sense) who’s shown us that business can be fun, success can be built unconventionally, and sometimes the road to your first million might just start with a hot dog cart and a crazy dream.

Not bad for a kid from St. Louis with curiosity to spare.