My First Million Podcast Summary

Episode: Why Is Andrew Wilkinson Monetizing His Twitter Followers?
Date: August 24, 2023
Hosts: Sam Parr and Shaan Puri
Guest: Andrew Wilkinson, Co-Founder of Tiny

Overview

In this episode, Sam and Shaan host Andrew Wilkinson, founder of the publicly traded holding company Tiny. Together, they dive deep into Andrew’s recent experiment monetizing his Twitter following, his thoughts on the “status game” among entrepreneurs, lessons from building and scaling agencies like Metalab, frameworks for maximizing business value, and a showcase of interesting niche investments. The episode is rich with behind-the-scenes business strategies, personal philosophies, and Andrew’s candid reflections on wealth, happiness, and fulfillment.

Key Discussion Points & Insights

1. The Twitter Monetization Experiment

• Why monetize followers?
  Andrew explains he started charging $29/month for a Twitter subscription for a filtered, high-value audience that can DM him, join an AMA, and access a Telegram group.
• Revenue and Results:
  • 550+ paying subscribers ($16k MRR; ~$200k ARR) with minimal time input.
  • Primary motivation was to filter outreach and create a community, but the unexpected upside was cash flow and even hiring through this group.
  • “I’m making money, and I’m getting deal flow.” (Andrew, 10:59)
• Business Math:
  • “If I get 1% conversion, that’s $800,000. If I do 5%, that’s $4 million… this is like $5, $10, $15M of value.”
    — Andrew Wilkinson [00:00]
• Motives Scrutinized:
  • Shaan speculates the real play is to catch Elon Musk’s attention. Andrew insists it’s genuinely about filter and connection, dismissing ulterior motives. [12:00]
• Filtering for Quality:
  • “I’m getting people being filtered out, the dinguses are filtered out.” (Andrew, 10:44)

2. The Status Game and Social Dynamics among Entrepreneurs

• Rooms Full of Billionaires:
  • Andrew shares experiences mingling with ultra-wealthy individuals (e.g., on a $100M yacht), and how the incremental status game never ends:
  • “I remember I was talking to a guy… he goes, ‘Lauren Powell Jobs is so fucking rich…’ and he goes glassy-eyed and he’s like, ‘Superyacht… I can’t do a superyacht yet.'” — Andrew, [24:35]
• Endless Ladder:
  • No matter the success level, there are always higher rungs. This relates to feelings of inadequacy or exclusion, even for high achievers.
  • “No end to the status game. It’s like leaving a party, you go to the next room, and you’re back at the kids’ table.” — Shaan, [25:24]
• Dealing with Social Anxiety:
  • Andrew’s solution: ask questions, make others feel good about themselves, and you’ll always leave a good impression. (Dale Carnegie approach) [19:32]
  • “Everybody wants to talk about themselves…” — Andrew, [19:32]

3. Building, Scaling, and Valuing Agencies (Metalab & Tiny)

• How Metalab Became a Cash Machine:
  • Metalab (product design agency) grew through niche focus, reputation, and mostly inbound business. High margins (public numbers: $81M revenue / $20M EBIT).
  • “We basically own product design and building MVPs for startups and worked at it for a really long time.” — Andrew, [28:56]
  • Agencies as “launchpad” businesses—a way to generate cash and fund other investments (Tiny’s acquisition model).
  • “If I lost everything… I would probably go start an agency. That is the easiest way to make $500k a year.” — Andrew, [35:11]
• Growth Strategy:
  • Created/acquired smaller agencies to capture excess demand (“sawdust from the sawmill”).
  • Model similar to Syed Balkhi’s (WPBeginner): combining audience/lead source with high-margin add-ons.
  • “One plus one equals a hundred.” — Andrew, [34:59]; [39:51]

4. Business Philosophy: Making, Spending, and Investing

• Profit First, Always:
  • Andrew recommends “Profit First” methodology: allocate profit upfront (“small plate” effect) rather than as an afterthought. [76:32]
• Dividend Discipline:
  • “You don’t want to leave excess cash burning a hole in the CEO’s pockets… I like them to basically have a month, two months of cash.” — Andrew, [78:28]
• Personal Income Philosophy:
  • “I want to spend 5% of what I earn, at most. Everything else goes into investments.” — Andrew, [81:01]
  • Living well is important—don't delay enjoying wealth, but avoid going overboard.
  • “The exit was right in your bank account… you could have just dividended the money out.” — Andrew, [82:01]
• Big Wins Matter Most:
  • Shaan: “For most of my 20s, I was just trying to figure out how do you make way more money? Not go from 20% to 30% savings.” [83:55]
  • Ramit Sethi principle: “Don’t focus on $3 problems like coffee, focus on $30,000 problems like getting a raise.” [85:21]

5. Cool Niche Business Examples

• No Story Lost ([44:04])
  • VIP version of StoryWorth: Biographers interview family members, creating custom-written biographies.
    • “I’m about to get this book, professionally written about my dad’s life.” — Andrew
    • Investment: $25k at ~$1M valuation, main challenge is customer acquisition.
• Routines Club ([51:41])
  • Aggregates daily routines of high-performers, with affiliate links. “Infinitely shareable” — easy SEO affiliate play.
• Maui Nui Venison ([55:13])
  • Hunts invasive Axis deer in Hawaii. Ethically sourced, ultra-healthy meat, strong regulatory moat, and big influencer backing.
  • “They’ve spent the last seven years getting approval to actually hunt and sell this meat…only people FDA-approved to sell it.” — Andrew

6. Reflections on Community Business Models (EO, YPO, Vistage, Hampton)

• Hampton’s Growth & Challenges:
  • Sam’s new business, inspired by EO, is a carefully curated founder community with high retention potential and long time horizons (“these can be 50–100 year companies”).
  • Critical to growing slowly and keeping quality high: “Once you screw up a community, I don’t think you can fix it.” — Sam, [68:06]
  • “You have an unfair advantage… free customer acquisition… one plus one equals a hundred.” — Andrew, [72:19]
• Culture Fit Above All:
  • The necessity of removing toxic members and curating values, even at the expense of short-term growth. [69:55]

Notable Quotes & Memorable Moments

• On status and value:
  “There’s no end to it… I look at him and I’m like, ‘What, can you not do that she can?’… and he’s like, ‘Superyacht. I can’t do a superyacht yet.’ That is the most pathetic, insane thing…”
  — Andrew Wilkinson [24:35]

• On newsletter/agency business models:
  “To a man with a hammer, everything looks like a nail. You’d probably both start newsletters; I’d start an agency. It’s whatever you know.”
  — Andrew Wilkinson [39:23]

• On filtering “dinguses”:
  “I’m getting people being filtered out, the dinguses are filtered out. I’m making money, and I’m actually getting deal flow.”
  — Andrew Wilkinson [10:44]

• On Buffett-style living:
  “How do you take enough of Buffett that you have the freedom to spend your time?”
  — Andrew Wilkinson [42:43]

• On startup valuation:
  “If you think about what you would pay for a business that makes that much money a year, like, this is like $5, $10, $15 million of value.”
  — Andrew Wilkinson [00:00]

• On community curation:
  “If there’s someone who’s toxic, the cancer has to be cut out. But that is an incredibly awkward conversation.”
  — Andrew Wilkinson [70:53]

• On the profit-first approach:
  “If you want to make 30% profit margins, take $30 of every $100 that comes in, you move it to another bank.”
  — Andrew Wilkinson [78:25]

Suggested Timestamps

• Monetizing Twitter: 08:53–14:59
• Status Games & Yacht Story: 21:49–25:06
• Agencies/Making Money as a Service Founder: 28:36–36:18
• Business Frameworks (1+1=100): 34:59–40:29
• Cool Business Pitches: 44:04–60:52
• Profit First & Dividend Discipline: 76:32–83:03
• Community Businesses (Hampton/EO): 66:46–76:07

Tone & Style

The conversation is lively, irreverent, and deeply candid — the hosts and Andrew mix sharp business acumen with playful roasting and off-the-cuff wit. This openness makes the episode both highly educational and relatable, particularly for entrepreneurs and creators thinking about how to leverage their audience, structure their businesses, and find meaning beyond numbers.

Final Takeaway

Andrew’s personal and business philosophy boils down to creating launchpad businesses, capturing “1+1=100” unfair advantages, enjoying wealth without being consumed by the status game, and above all, constructing lives and careers aligned with one’s genuine interests. Whether you’re building an agency, developing a subscription community, or investing in deer jerky, the real wins come from focusing on the right leverage, the right community, and the right mindset.

For more business brainstorms, personal anecdotes, and irreverent takes, listen to the full episode of My First Million.