Ever wondered what it really takes to build a media company from scratch and sell it for a fortune? Sam Parr (The Hustle founder) sat down with Austin Rief and Alex Lieberman (Morning Brew co-founders) for an incredibly candid, year-by-year breakdown of their parallel journeys.

From college dorm rooms and scrappy beginnings to navigating massive growth, near-death moments during COVID, and ultimately selling their newsletter empires (Morning Brew for $75M, The Hustle for a reported $27M), they spilled the beans on revenue, subscribers, profits, key hires, brutal lessons, and biggest regrets.

If you missed this masterclass in media entrepreneurship, here are the key insights and takeaways:

1. The Early Grind & Contrasting Starts (2015-2016):

• Origins: Morning Brew started as a PDF attachment (Market Corner) by Alex in college to help finance students understand the news, with Austin joining soon after. The Hustle began as Sam’s successful event series (HustleCon) before pivoting to a newsletter.
• Revenue Pressure (or Lack Thereof): Brew had the advantage of starting while in school, giving them ~1.5-2 years without intense pressure to monetize. HustleCon was profitable from the start, funding the initial newsletter launch.
• Early Wins & Validation: Brew hit early product-market fit with finance students. HustleCon proved Sam could build an audience and generate revenue.
• Scrappiness & Regrets: Sam regrets extreme early frugality (like buying/returning Costco supplies). Alex regretted not getting formal permission for Brew while at Morgan Stanley (leading to an insider trading scare).
• Funding Decisions: Sam raised a small round for The Hustle early on but later regretted having too many small investors. Brew raised $750k later, primarily driven by the need to make payroll due to ad payment cycles. Lesson: Raise as little as possible, or not at all if cash flow allows.

2. Scaling Wars: Growth vs. Profitability (2017-2018):

• Finding Talent: Both emphasized hiring non-traditional talent with high potential (bloggers, growth engineers) rather than expensive, established media figures. Brew highlighted Neil Fryman’s critical role in executing their content vision. Sam noted poaching talent often involved selling the dream.
• Aggressive Ad Spend: Brew went all-in on paid acquisition (spending up to 500k/monthonFacebookadsbyendof2018)oncetheyfelttheyhadproduct−marketfit.TheHustlespentsignificantly(500k/monthonFacebookadsbyendof2018)oncetheyfelttheyhadproduct−marketfit.TheHustlespentsignificantly(1M in 2018) but Sam admits his scarcity mindset held them back from being as aggressive as Brew.
• Culture & Values: Brew established core values early (“Ownership Mentality,” “Underdog Mentality”) which drove their intensity. Sam regrets not codifying The Hustle’s values and culture formally until much later.
• The Spreadsheet Math: Both relied on simple spreadsheet models projecting subscriber growth and CPMs to validate the business model, often baffling outsiders but proving effective.
• Brutal Content Standards: Brew described a maniacal daily process of printing out competitors’ newsletters and ruthlessly critiquing their own content to maintain high standards. Lesson: The standard you allow becomes the standard.

3. Maturation & Strategic Pivots (2019):

• Hitting Plateaus: Brew realized the economics of a single, broad newsletter were plateauing ($18/subscriber/year potential) and began launching niche B2B verticals (Retail, Marketing, etc.) with higher CPMs.
• Focus Shift (Hustle): Sam launched the My First Million podcast and the high-ticket subscription product “Trends” ($300/year), shifting focus from pure user growth to cash flow and direct monetization as he felt burnout approaching.
• Operationalizing the Business: Reading the book Traction (implementing the Entrepreneurial Operating System – EOS) was a transformational moment for both companies, helping them build structure, processes, and transition from founder-led chaos to scalable businesses. Austin effectively took over as operational CEO at Brew during this phase.
• Founder Dynamics: The Brew co-founders acknowledged their relationship and communication matured significantly over time, initially lacking the radical candor they developed later. Sam reflected on the loneliness of being a solo founder without that built-in peer support.

4. The Exit: Selling Under Pressure (2020):

• Timing & COVID Impact: Both sold in 2020. COVID initially caused panic (Brew lost 30% booked revenue almost overnight), forcing drastic brainstorming (Patreon? Education products?). Then, business boomed in the second half of the year for both.
• The Sale Process: Brew’s process was long (11 months) and grueling. Hustle’s sale to HubSpot was faster and done without a banker (Sam had a bad prior experience).
• Emotional Toll: Described as the most intense, horrible, and miserable period. Dealing with investor expectations, employee anxieties (“How do I get mine?”), and the pressure of a life-changing event was incredibly stressful. Austin learned how to “be right without being an asshole.”
• Deal Dynamics: Brew shopped the deal widely to media companies but got little interest; Axel Springer was the main contender. Kip Manley (HubSpot CMO) revealed he’d wanted to buy both Brew and Hustle earlier but timing/stage wasn’t right.

5. Lessons Learned & Key Mistakes:

• Don’t Raise (Unless Necessary): Both advocate for bootstrapping or raising minimal funds, emphasizing the benefits of retaining ownership.
• Codify Values Early: Define your culture and operating principles sooner rather than later.
• Focus Maniacally on Content: It’s the core product; everything else follows. Don’t chase growth hacks with mediocre content.
• Hire Non-Traditionally: Look for potential and drive, not just credentials.
• EOS / Traction: Implement an operating system to scale beyond founder control. Hire an implementer (Sam’s regret).
• Know Your Numbers: Understand unit economics (value per subscriber, CPMs) deeply.
• Pivoting is Hard: Moving from content to physical products or software is extremely difficult; stick close to core competencies.

6. The Future of Newsletters & Media:

• Harder Game: The arbitrage/easy wins of 2017 are gone. Newsletters, podcasts, YouTube – everything is more saturated.
• Niche is Key: Go deep into a specific vertical where you can build trust and monetize directly (higher CPMs, info products, subscriptions). B2B is often more resilient.
• Content Quality Paramount: Readers are less tolerant of mediocrity.
• Physical Opportunity: Potential exists for high-quality, high-priced physical quarterly magazines/newsletters for specific industries (Sam’s idea).
• New Frontiers: Alternative investments media (Alex’s idea), better retail investor support (competing with Motley Fool).
• Big Swings: Use content as the funnel for ambitious ventures (e.g., Overtime model in sports).

Wildest/Most Interesting Story:

• The Morning Brew team pitching SoFi, only to be brutally shut down by an executive who, after seeing their pitch for reaching millions via email, dismissively showed the SoFi Stadium background on Zoom and asked, “We have 300 million eyeballs a year [from the stadium]. Why would we want 3 million emails?” Ouch.

Overall Vibe:

Incredibly raw, honest, and vulnerable. This wasn’t just business talk; it was therapy. Sam, Austin, and Alex shared the highs, the lows, the numbers, the personal struggles, and the hard-won wisdom from building two of the most successful newsletter businesses of the last decade. Packed with actionable insights for any entrepreneur, media operator, or creator.

Find Sam Parr on the My First Million podcast. Find Austin Rief (@austin_rief) and Alex Lieberman (@businessbarista) on Twitter/X.

Listen to the full episode here: [Link to MFM Episode]

Until next time,

The Podcast Notes Team