There’s a long, awkward stretch where you’re doing the work but can’t yet justify it to yourself, let alone anyone else. It doesn’t feel like failure - just a lot of effort with very little external validation. 

That’s usually where most people tap out.

Sam Parr didn’t. 

Long before he launched The Hustle (the wildly popular business newsletter that later sold to HubSpot), he was in Nashville selling hot dogs on the pavement, sweating in the sun and shouting “ALL BEEF!” at passing strangers.

A few years after his stint at the Wiener stand, he ended up raising $1M in seed funding, growing The Hustle to nearly 2 million subscribers, turning it into a $15M-a-year business and walking away with an eight-figure acquisition.

Fair to say things escalated.

But how exactly did he go from that unsexy day job to a multimillion-dollar exit? While looking into this case study, I didn’t find a neat shortcut - there never is. However, there are a few decisions and patterns SMEs raising capital can learn from.

If you’re at a job you secretly (or openly) can’t stand, keep reading.

This one’s a long read, so here’s a quick rundown before you commit:

1/ Sam Parr went from Tennessee hot-dog cart to eight-figure exit through persistence, not genius.

2/ Every step he took - HustleCon, The Hustle, Trends - created more leverage than the step before it.

3/ He raised small, kept control and only took capital when his numbers proved the model.

4/ His audience was the real asset; HubSpot bought distribution and trust, not tech.

5/ The entire journey is a reminder that momentum beats inspiration - start, keep going and stack sensible moves until the leverage becomes obvious.

Sam Parr didn’t start out with some grand entrepreneurial identity. He did what most people do in their early working lives: whatever job was available. For him, that included flogging hot dogs to disinterested pedestrians in the Nashville heat.

Hardly a dream job, but oddly effective training.

Because when you’re selling hot dogs, you learn how real people behave - not hypothetical “users”. You see what makes someone stop, what makes someone buy, and what makes them walk away. You also learn that good ideas don’t magically spread; you have to put them in front of people repeatedly and loudly.

This experience becomes relevant later, as Sam’s entire fundraising success is rooted in his understanding of attention, demand and practical execution - all of which he learned long before he touched a pitch deck.

Eventually Sam moved to San Francisco because… that’s what ambitious 20-somethings did at the time. Airbnb even offered him a job. Then pulled it after a background check. Brutal.

Fortunately, Sam ignored the cosmic sign to go home. He stayed, got sober and started building relationships the only way he knew how - by pulling people into something social and slightly odd: The Anti-MBA Book Club.

This wasn’t a business. It wasn’t a “growth strategy”. It was just Sam being Sam.

But it did something critical: it plugged him into a network of founders and investors. The exact people he would later raise from.

Founders obsess over pitch decks and metrics, but they forget that most capital raises start with one thing: a warm intro and a reputation for showing up.

This phase gave him both.

Through that book club network, he met designer John Havel and ended up co-founding Bunky - a roommate-matching app. Ten months later, they sold it for roughly $15K. Not life-changing, but it came with a one-year job paying around $100K.

On paper, it looks minor. But this is where founders misunderstand momentum.

A “tiny exit” plus stable income buys you time.

→ Time buys you clarity

→ Clarity forces better decisions

Sam now had the breathing room to think bigger without panicking about rent. And when founders aren’t panicking, they start building properly - which is exactly what happened next.

Sam inherited the name “HustleCon” (a niche event for early-stage founders) and a 300-person email list. Sam turned it into a full-blown, profitable conference in six weeks.

He cold-emailed speakers, wrote blog posts about them and plastered those posts across every platform with a comment box. It was messy, inconsistent, borderline chaotic - and extremely effective.

And here’s the capital-raise-relevant part:

HustleCon proved that Sam could acquire customers profitably, build an audience from scratch, and monetise that audience immediately. Investors don’t invest in “ideas”. They invest in patterns. HustleCon was the first undeniable pattern.

In 2015, Sam used HustleCon profits plus another $250K seed cheque to launch The Hustle. And this is where everything compounds.

He wrote constantly - sometimes under his own name, sometimes under alter egos - pushing out bold, viral articles. He had a sharp instinct for what the internet wanted to read.

As a result:

Then he made the shift that changed everything: turning The Hustle into a daily email. Business news written like a human, not a Deloitte consultant. It became part of people’s morning routine, which meant the list didn’t just grow - it stuck.

The subscriber count went from 100k → 500k → over 1 million.

This is the point where capital raises stop being uphill battles. When you have an audience this size and this engaged, you’re no longer pitching investors - they’re circling you.

And the part SMEs should copy? Sam didn’t spend on ads until he had 250k organic subscribers and knew exactly what each one was worth. Once the numbers were solid, then he scaled.

Fast forward to 2019, and Sam launched Trends - a paid community and research product. He tested it by throwing up a Gumroad presale. It pulled in $30K in 24 hours. At launch, it hit $1.2M ARR with 4,000 subscribers - later surpassing 10,000.

This was the final confirmation that The Hustle wasn’t a “newsletter business”, but a monetisable attention engine. Ads, events, subscriptions, community… it all worked.

By this point, Sam had:

In other words: the perfect conditions for a seed round that he controlled, not the other way around.

By the time The Hustle attracted buyers, HubSpot had realised that ads only work while you pay for them. Owning an audience lasts.

So HubSpot started building “HubSpot Media”, and The Hustle was basically the cheat code. A daily email with 1.5-2 million young professionals already reading it first thing in the morning?

Exactly the audience HubSpot drools over.

Exactly the distribution they couldn’t build themselves.

Zero effort required on their end.

The team was another selling point. They could launch things like My First Million without overthinking it, which is a rare trait in media teams.

When HubSpot floated a partnership, Sam didn’t play corporate tango - he asked whether they were interested in buying the business. Bluntly. 

He followed it up with a memo that was almost aggressively honest - here’s what works, here’s what doesn’t, here’s where the bodies are buried. 

And it worked - because buyers actually appreciate that honesty (mainly because they already know).

The deal reportedly landed somewhere in the $20-$27M range, with about $17.2M in cash and the rest in HubSpot stock. The stock then doubled, which is the sort of financial outcome you brag about but pretend you’re humble about.

Because he never took meaningful VC money, Sam kept a huge personal stake.

And because he was brutally honest about being sick of running the company, the acquisition also came with the bonus prize of not being a CEO anymore. 

He got to keep doing the parts he enjoyed - creating, talking, scheming - without the bits that make founders question their life choices (HR, budgets, Slack threads that should’ve been emails).

After the sale, things moved in a fairly predictable direction. He married his girlfriend Sara, moved to Austin, became a dad and, unsurprisingly, started new projects. Turns out selling a business doesn’t cure the urge to build things, it just removes some of the friction.

Hampton launched and took off.

Sam’s List appeared out of nowhere and made money.

Other niche experiments followed.

All of it came from one simple principle: build leverage first, raise or sell second - and only when you actually have options.

Let’s pull this out of story time and into something you can apply.

Sam didn’t sit around waiting for a perfect idea or a life-changing epiphany. He sold hot dogs, ran a book club, built a conference, wrote a newsletter - he just kept moving. None of these things looked like “the big one” at the time. But each tiny experiment opened a door he couldn’t see yet. 

Sam gained clarity by getting stuck in and doing the things. If you feel stuck, it’s rarely because you need a better plan - it’s because you haven’t started anything that gives you new information.

The path looks linear only in hindsight: hot dogs → HustleCon → The Hustle → Trends → and beyond. In reality, each stage was funded by customers first, long before investors showed up. HustleCon profits paid for The Hustle.

Early ads paid for the next hires. Revenue validated the idea before any pitch deck did. So when Sam eventually raised capital, it wasn’t to “see if the business worked”. It was to scale something that clearly already did.

I wrote about this on LinkedIn and, shockingly, no one argued:

That’s the difference between raising from strength and raising from panic - investors can smell the difference a mile off.

Sam didn’t raise a headline-grabbing round. In total, he raised a low seven-figure amount - modest by startup standards, but intentional.

That restraint meant he kept a large personal stake. It also meant he avoided the VC treadmill, where growth-at-all-costs becomes mandatory because someone else’s return depends on it.

Instead, Sam stayed focused on the outcome he actually wanted: a business that was profitable, controlled and sellable on his terms. So when HubSpot came knocking, he didn’t need permission from investors who owned half the company.

HubSpot bought The Hustle’s distribution: 1-2 million people, exactly in their target demographic, opening an email every morning. 

That kind of attention is incredibly hard to build and ridiculously expensive to buy. Sam created it for free using writing, consistency and personality. An audience is leverage - for sales, for fundraising, for exits. Products can be copied; distribution cannot. 

If you’re building something you may eventually sell, start building the audience your future acquirer wishes they already owned.

Sam didn’t touch paid acquisition until The Hustle had 250K organic subscribers and a clear grip on the fundamentals - LTV, CAC and payback. By the time he spent on growth, the economics were already understood.

So when The Hustle finally scaled spend, it was straightforward maths: £X per subscriber, £Y in lifetime value, Z-month payback.

 If you can’t explain your unit economics in one sentence, you’re not ready to raise or scale.

Nothing Sam did was “the big plan”. 
The small exit from Bunk gave him a salary and time. 
That time gave him the space to build HustleCon. 
HustleCon gave him cash flow and an email list. 
That list powered The Hustle. 
The Hustle built a brand strong enough to launch Trends. 
Trends proved he could monetise the audience in multiple ways. 
Each step de-risked the next one. 

This is how you compound advantage: not by swinging for a home run, but by stacking small, low-risk moves until you suddenly have leverage. 

Plenty of people have run newsletters. Very few have grown them like Sam. 

His real advantage wasn’t the idea, but his ability to write, sell, recruit, promote, hustle, improvise and get attention from strangers on the internet. 

The lesson? Rather than just focusing on the numbers, demonstrate what you’re good at to investors. Show them how those skills reduce risk.

Funnily enough, it’s also worth showing what you’re not good at. During the HubSpot talks, Sam sent a memo that listed everything The Hustle didn’t do well - right next to the things it did incredibly well.When you’re not desperate, you earn the right to be brutally honest - and this shortens timelines in the process since acquirers stop worrying about what you may be hiding. 

Transparency creates trust, and trust creates leverage. It also signals that you’re confident enough in your strengths that the flaws don’t scare you.

So no, you don’t need to sell hot dogs, run a conference and build a newsletter empire to raise capital from a position of strength.

I was listening to Don’t Stop Me Now the other day - as you do - and ended up down a Queen rabbit hole. Which reminded me how overqualified that band was on paper. 

Did you know that Brian May has a PhD in astrophysics? And Roger Taylor studied biology? These weren’t people short on options; they could’ve done almost anything.

Instead, they chose music. Loud, theatrical, slightly ridiculous music. And it worked.

I like that as a reminder. We tend to treat our current path like it’s fixed, as if choosing one thing automatically rules out everything else. 

It doesn’t. 

Most limits are self-imposed. People are far more flexible - and capable - than they give themselves credit for.

Sam Parr didn’t have a world-changing idea. He kept stacking small, sensible moves until they turned into real leverage. That’s how he really won.

It’s impressive, really - nothing he did was flashy or perfectly timed, and yet the compounding was almost superhuman.

So, if you take one thing away from this newsletter, just start. It’s the only part you can’t outsource.

Till next time,

James