The Hustle $27M founder story

Hey, it's Guy & Farzan,

It's Wednesday. 37 degrees in Sydney. Took Enzo the Cavoodle to the water. In and out all day. Stay cool. Here are this week's founder stories.

Reading time: 8.5 mins

In the mail today. 3 founder stories, 2 founder notes

 Founder story 1 

From Selling hot dogs on Nashville streets to building a million-subscriber newsletter and exiting to HubSpot for $27 Million in just six years.

The Journey
- Started selling hot dogs outside a Nashville music venue as a college student
- Launched online ventures while still hustling on the streets
- Founded Hustle Con conference in 2014 with just $6,000
- Launched The Hustle newsletter in 2014 with content marketing strategies
- Relocated to San Francisco to pursue tech opportunities

The Evolution of Vision
- 2014: Created a one-day conference for startup enthusiasts (Hustle Con)
- 2014: Started The Hustle as a weekly newsletter with viral content
- 2016: Rebranded to daily business news inspired by TheSkimm
- 2019: Launched Trends subscription service for entrepreneurs
- 2019: Started My First Million podcast with Shaan Puri
- 2021: Sold to HubSpot for $27 million with 1M+ subscribers

Overcoming Obstacles
- Started from scratch selling hot dogs in extreme weather conditions
- Lost Airbnb job offer due to background check disclosure mistake
- Had to sleep on streets for 2-4 nights to secure prime festival locations
- Initial podcast struggled with only 10,000 downloads per episode after strong start
- Realized creating controversial viral content was exhausting and unsustainable
- Managed the stress of producing annual conferences while seeking different model

Today's Impact
- 1 million+ newsletter subscribers
- $15 million annual revenue
- Around 30 employees
- Sold to HubSpot for $27 million
- My First Million podcast: hundreds of thousands of monthly downloads
- Trends.co: Exclusive community for entrepreneurs

Growth Strategies That Worked
- Viral Content: Posted outrageous stories on Reddit to drive traffic
- Ambassador Program: Generated 300,000 email subscribers through referral program
- Content Marketing: Sent newsletters, blog posts, and Reddit posts to build audience
- Unique Rewards: Offered branded swag with handwritten notes to keep ambassadors engaged
- Daily Consistency: Shifted to daily news format that people could rely on
- Podcast Persistence: Released 2-3 episodes weekly for two years despite initial struggles

Key Milestones
- Started hot dog stand with $500 in supplies
- Made up to $2,000 cash per day on good days
- Sold roommate app "Bunk" to Apartment List for $15,000
- First Hustle Con generated $50,000 with $6,000 investment
- Second Hustle Con made $188,000 with $17,000 budget
- Grew to 75,000-80,000 subscribers and secured first advertisers at $1,000 per placement
- Raised $800,000 from angel investors
- Hit 100,000 subscribers in first year after 2016 rebrand
- Reached 500,000 subscribers in second year
- Achieved 1 million subscribers by third year HubSpot acquisition in October 2021

The Philosophy

"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."

"When I sold, I was a person with poor eyesight who put on glasses and saw the world differently. 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."

Founder story 2

See how Lily built a $5K/month business from her bedroom

Lily quit her 9-to-5 to build a $5K/month wellness business in 2.5 years. Started with a $5.99 candle sold to her mom on Shopify.

Here's how she did it:  
→ Bought a candle kit off Amazon during a rough patch
→ Made one candle, sold it to her mom for $5.99 on Shopify
→ Friends started buying, ordered wholesale stock
→ Did pop-up at local gym, made £850 in one day
→ Applied to Westfield (despite doubts), got accepted
→ Bought too much stock early, ate through savings
→ Someone suggested a candle-making workshop collab
→ Discovered workshops had 85% profit margins
→ Converted garden studio into workshop space
→ Now profitable at $5K/month, hired first employee

Key lessons from Simon Squibb:  
- You only need ONE customer to start (even if it's your mom)
- Don't buy big inventory
- Test demand first with small batches
- Say YES to opportunities you've never done before
- Use pop-ups in existing spaces vs. expensive retail
- Build 1,000 "true fans" who tell 10 people each
- Create community value WITHOUT extraction
- Start with WhatsApp groups before building apps
- Partner with influencers through equity, not just paid posts

The path to $10K/month: Focus on workshops (higher margins), leverage influencer partnerships, and build community through behind-the-scenes content and customer connections.

Founder story 3

From class clown to six-figure revenue: How Jake, Lezlie, and Nick built a chocolate empire that sold over 25 Million Bars."

The Journey
- Jake struggled academically in high school and became the class clown
- Failed to graduate with his class, then went to college to become an actuary
- Couldn't secure a summer banking job, had an epiphany watching Shark Tank
- Started outdoor fitness boot camps in Montreal, making good money
- Launched a clothing brand that became popular but went bankrupt
- Lezlie closed her fashion company while Nick sold his software company
- Lezlie had been making healthy chocolate squares for Nick for 2.5 years
- Nick found market research showing rapid growth in dark chocolate and plant-based protein
- Jake's sister Lezlie and brother-in-law Nick approached him to be their third partner in August 2018 Officially launched Mid-Day Squares in August 2018 with Jake handling brand and storytelling

The Evolution of Vision
- 2018: Created a healthier chocolate alternative with real food ingredients, dark chocolate, protein, and fiber
- 2018: Launched with goal to build the next big chocolate snacking company in the better-for-you space
- 2019-2020: Expanded from online direct-to-consumer to retail partnerships
- 2021-2023: Scaled across North America, entering 7,000 stores
- 2024: Focused on dominating afternoon snacking and chocolate markets Future Vision: Become a modern-day Hershey's in the better food space with $150M+ annual revenue

Overcoming Obstacles
- Started with zero budget competing against giants like Hershey's and Mars
- Couldn't afford traditional marketing materials or store real estate
- Faced significant challenges with scaling and manufacturing an innovative product
- Required three years of R&D to perfect the formulation and manufacturing process
- Had to convince retailers to take a chance on an unknown brand
- Built everything from scratch without traditional resources
- Balanced the pressure cooker environment of entrepreneurship with staying resilient

Today's Impact
- Six-figure revenue business In 7,000 stores across Canada and USA
- Sold over 25 million bars
- Raised $17 million to scale the business
- Shipped over 700,000 Polaroid pictures with custom messages
- Built a strong community of fans who feel connected to the founders
- Expanded from one flavour to multiple product lines

Growth Strategies That Worked
- Sample Program: Charged $0.25 initially for sample bars to attract serious customers, not freeloaders
- Hand Delivery: Personally delivered orders in Montreal with Polaroid pictures and handwritten custom messages
- Personalization: Looked up customers on social media and personalized messages (mentioning their dogs, etc.)
- Social Media Storytelling: Documented and shared everything about building the business—the good, bad, and ugly
- Turned Customers into Fans: Made customers feel like they were buying from friends, family, or neighbours
- Word of Mouth: Created memorable experiences that people shared online In-House Engineering: Built internal tools and software to streamline manufacturing and data analysis
- Data-Driven Decisions: Used purchasing data, SPINS data, and Nielsen data to guide resource allocation
- Building Out Loud: Followed Elon Musk's approach to marketing and transparency

Key Milestones
- 2016-2018: Lezlie created healthy chocolate squares for Nick for personal use
- 2018 (June/July): Jake joined as third partner to handle branding and storytelling
- 2018 (August): Officially launched Mid-Day Squares
- 2018-2019: Started with sample program at $0.25, gradually increased to $1 before stopping
- 2019-2021: Expanded from online to retail, entering stores across North America
- 2021-2023: Grew to 7,000 stores across Canada and USA
- 2023: Sold over 25 million bars total
- 2023: Raised $17 million in funding to scale the business
- 2024: Shipped over 700,000 Polaroid pictures since launch

The Philosophy

"Always be unapologetically yourself no matter what."

"Be really comfortable with getting uncomfortable because those are the times when greatness happens."

"Block out the noise and stop comparing yourself to others. This is a dangerous path to go down because it distracts you from your own goals and prevents you from being your best self."

"Freedom is the most valuable thing in the world. I am driven by the freedom that comes from being unapologetically myself every single day."

"There's something incredibly powerful about embracing the uncertainty of not knowing whether we can do it, coupled with the determination to give it our all."

"What sets you apart is your uniqueness. Embracing and leaning into that is what gives you the best chance at success."

 Founder note from Joseph Lee founder of Supademo  

I turned 30 this year.

While I don’t have everything figured out, here are 30 lessons I’d tell my younger self:

1. Invest in your own well-being. It’s the highest ROI action you can take.

2. Stop associating vanity metrics with success. A lot of what you read about “killing it” isn’t always true. Trying to measure progress against handpicked, rosy stories is pointless and harmful.

3. Don’t be so rigid about the definition of a ‘startup.’ Not all industries are created equal. Some scale rapidly, others take time.

4. Take advice with a grain of salt (especially from non-operators).

5. Be mindful of your time & who you spend it with. You learn through osmosis.

6. Stop working on what’s fun. Work on things that actually matter.

7. Avoid sweeping failure under the rug. Instead, dissect it: it's the best way to learn.

8. Institutionalize the celebration of milestones. Or forever chase a moving goalpost.

9. Embrace the opportunities that come with uncertainty.

10. Don't wait too long for more data. The opportunity could be long gone.

11. Work with people with complementary skills.

12. Great artists steal. Always be on the search for great ideas.

13. Find time for friends, family, and your partner. Time-block if you must.

14. Periodically slow your pace and look around.

15. Don’t be arrogant. It’s the fastest way to tarnish your reputation.

16. Find experienced, credible mentors who've done what you’re trying to do.

17. When it comes to investors, everything but a term sheet is a NO.

18. Travel & explore the world while you’re young.

19. Some of the greatest, most valuable folks are unseen and execute behind the curtains. Give them the spotlight from time to time.

20. You don't owe your investors any returns. But you do owe them earnest effort, time, and passion.

21. Building a remote team? Get into the habit of oversharing and posting in public Slack channels. It’s better to overshare than to create knowledge silos.

22. Default to saying yes. Many of us have become lazier, flakier, and less present in today’s hyperconnected society.

23. Action is almost always better than inaction (in the startup world).

24. Be open to changing opinions. The world is more fractured than ever, and I think much is due to the hardening of opinions. Be open to contrarian views and be flexible to change.

25. There’s always a third door. Go find it.

26. Take accountability for your actions. Credibility is not given; it’s earned.

27. Health powers everything. Make sleep, strength, and sunlight non‑negotiable. Turn these into habits and let compounding do the rest.

28. Entitlement kills growth. Trade comfort early in your career for freedom later.

29. You’re not the company. The company is not you. Try not to associate your identity and self-worth with your startup.

30. We’re small in the grand scheme of things. Live your life doing great work, but don’t grip so tightly that life slips by.

 A founder note we loved

That’s all for this week. See you in a week.

Quick reminder - If you like our newsletter, please do “add to address book” or reply. These are “positive signals” that help our newsletter land in your inbox. If you hate it, please unsubscribe (the unsubscribe link is in the footer).

Cheers

Guy + Farzan
Founderoo