Startup Stories - Mixergy

Episode #2269: How the “My First Million” Guy Made his Money

Host: Andrew Warner
Guest: Shaan Puri
Date: November 15, 2024

Episode Overview

This episode features Andrew Warner in conversation with Shaan Puri, best known as co-host of “My First Million” and founder of The Milk Road newsletter. The discussion dives deeply into Shaan’s entrepreneurial history, how he built and sold several digital businesses (notably Milk Road and Bebo), his unique philosophies on motivation, business growth, product design, and the art of spending “startup money.” The two also touch on practical advice for newsletter entrepreneurs, the challenges and rewards of exits, and lessons from both failure and success. The tone is candid, witty, and densely packed with takeaways for aspiring founders.

Key Discussion Points and Insights

1. Early Days & Bebo Acquisition

[00:45–07:20]

• Shaan retells how he became CEO at Michael Birch’s IdeaLab (“Monkey Inferno”) after moving from Australia to San Francisco.
• Bebo, which sold to AOL for $850M, was reacquired by Birch (and Shaan) for $1M after AOL wrote it off.
• Attempts to revive Bebo included multiple product “shots on goal” (video messenger, a Bitmoji-like tool) until they created a live streaming app, which was then acquired by Twitch/Amazon.

“We bought it back for $1 million in a crazy high stakes game of poker…” (Shaan Puri, 04:38)

• Exit details: While some believed Shaan didn’t benefit much, he affirms, “I had a stake in that business and … it was a good exit for everybody.” (07:05)

2. Mindset After a Win & Motivation Shift

[08:12–13:07]

• Shaan describes feeling driven even after success—a trait Andrew attributes to many classic entrepreneurs. Shaan reframes this as using capital (financial and psychological) to experiment outside pure monetary gain.

“If not, what was the point of making life changing money if it doesn’t change your perspective of life?” (Shaan, 10:59)

• Launching “My First Million” was about becoming the “voice in people’s earballs” as a mentor/friend, not optimizing for profit.

3. Origin of “My First Million” & Growth Partnerships

[13:07–14:58]

• Shaan started the podcast solo, then partnered with Sam Parr (The Hustle) for distribution, splitting revenue 50/50—a play to combine “content for audience” in a no-brainer partnership.

“The entrepreneur doesn’t turn off… if I went to Sam, he’s got a big audience, he’s got no podcast.” (Shaan, 13:28)

4. The Milk Road: Why a Crypto Newsletter?

[14:58–18:24]

• Crypto’s rapid evolution and Shaan’s belief in “hosting, not attending, the party” led him to start a newsletter to become central in the crypto scene.

“Hosting the party is certainly more work... but it’s 100x the return.” (Shaan, 15:43)

• Shaan saw newsletters as the best “forcing function” to learn, network, and be at the center of opportunities in crypto.

5. Newsletter Growth, Product, and Differentiation

[20:23–40:26]

• Initially, Shaan acted as editor, not the writer, building a repeatable format so others could write (“editor, not author”).
• Differentiating factor: Combine humor with basic, essential learning—leave readers “a bit smarter” and entertained.
• Key insight: Most newsletter growth came from producing a “remarkable product” (not “growth hacks”), resulting in high organic referrals.

“A product over time will become as good as our taste. And having great taste is a creative... competitive advantage and is something that cannot be copied.” (Shaan, 38:20)

• Referral programs and partnering with Beehive, a newsletter platform built with necessary automations and referral systems, enabled recommended growth.

Growth Tactics Breakdown

[27:13–33:30]

• Early users: Focus on the “10 people who would love this.”
• Used Twitter for initial traction—offering “scarcity and mystery.”
• Stunt idea: “What if I put up a million dollars in a crypto wallet and tried to run it up to 10 million?” (Spoiler: It didn’t add much growth.)
• The main driver was making The Milk Road “the email you look forward to opening” with approachable content and humor.

Humor & Creative Habits

[33:43–39:03]

• Example: Ending every newsletter with a silly photo of Ethereum’s Vitalik Buterin.
• Writers used voice memos to pitch stories before writing—ensuring conversational, group-chat tone.
• Format (consistent structure) is critical in building habit and loyalty (like a TV show “template”).
• “Stealing with taste” from admired media (like Bill Simmons’ mailbags) and making it fit their style.

6. Revenue, Exit, and Spending Success

[40:26–47:10]

• Ad revenue topped $1M–$2M/year before the Milk Road’s sale.
• The exit was “the best exit experience” Shaan’s had, despite being during a downturn in crypto markets; terms remain undisclosed.

“All exits are a roller coaster... The exit for this was not tough. It was amazing. It’s probably the best exit experience we’ve had…” (Shaan, 41:07)

• Post-exit: Shaan spends money on everyday joys rather than “status” items (“I always buy socks when I exit”).
• Best spend: Hiring a private chef for family—biggest impact on time, health, and happiness for the whole household.

“Anybody who buys, like, a hundred thousand dollar car before you have a chef, I think is a wild decision.” (Shaan, 46:01)

7. Teaching Kids & Entrepreneurial Lessons

[48:19–50:03]

• Shaan’s young children are too small for structured entrepreneurship lessons, but his philosophy is to learn from kids’ playfulness and curiosity, “not trying to make her an entrepreneur right now.”
• Learning through play and small projects (like lemonade stands when they're ready) is better than formal business instruction.

8. Ownership and Structure of “My First Million”

[50:20–51:07]

• HubSpot owns the IP due to The Hustle’s acquisition, but Shaan and Sam retained creative control and upside.

“We maintain [creative control and upside], and they get to own the IP.” (Shaan, 50:45)

Notable Quotes & Memorable Moments

• On Motivation & Success:
  “My motivation was like, I think I'm good, but the evidence says I suck. Which one is it? … I want to spend the next year just doing whatever seems most interesting to me.” (Shaan, 10:36)
• On Product vs. Growth Hacks:
  “A more remarkable product is better, meaning a product that stands out because it's different and is worth telling other people about was the thing that actually worked for us.” (Shaan, 31:42)
• On Humor & Format:
  “Consumers think they want variety, but what they really want is familiarity—a format that doesn't change builds habit.” (Shaan, 36:45)
• On Spending Money:
  “You forgot the purpose of this thing! This thing is a tool to improve the quality of your life.” (Shaan, 47:05)
• On Teaching Kids:
  “The best thing to do with kids is to be a kid… I actually spend more time trying to learn from them versus trying to teach them how to be more like me.” (Shaan, 48:45)

Important Segments & Timestamps

• [00:45–07:20] Shaan’s Bebo story and first big exit
• [10:22–13:07] Perspective shift after selling, leading to launching the podcast
• [15:43–18:24] The “host the party” philosophy behind Milk Road’s origins
• [20:23–22:29] Newsletter as “forcing function” for learning and relationships
• [27:13–33:30] Early growth tactics for Milk Road—what worked and what didn’t
• [33:43–35:26] Embedding humor, storytelling, and personality in the newsletter
• [40:26–43:16] The reality of exits, revenue numbers, and the sale process
• [43:46–47:10] Post-exit spending philosophy—socks, chefs, and everyday upgrades
• [48:19–50:03] Passing entrepreneurial spirit to children

Conclusion

Shaan Puri’s startup story is packed with practical wisdom: from bootstrapping daily newsletters and engineering a remarkable product, to “winning” in ways that change your life more than your status. His transparent approach to both success and failure models a kind of entrepreneurship driven by intrinsic curiosity, taste, and reinvesting in life’s true pleasures—while building teams and products others want to talk about. Andrew’s probing questions and Shaan’s candid answers make this a vital episode for any founder wondering “what comes after the win.”

Further Resources

• Beehiiv (Newsletter platform): mixergy.com/beehive (for free trial mentioned in episode)
• My First Million Podcast: Podcast link
• Andrew Warner’s Book: “Stop Asking Questions”

(Summary by Startup Stories - Mixergy Podcast Summarizer, all rights to content remain with Mixergy and original creators.)