The $500 billion Ai gamble

Hey, it's Guy & Farzan.

The rain finally stopped in Sydney. Week of sun ahead. Been painting my kids' bedroom while they're away. Slow, methodical and surprisingly zen. Also been getting in the surf which is lush. Salt water therapy. Enjoy this week's founder stories.

Reading time: 8 mins

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

 Founder story 1 

Masayoshi Son: From $70B Crash to $500B AI Gamble

From bullied Korean outsider to tech gambling legend: How Masayoshi Son lost $70 billion, built SoftBank into a global empire, and placed a $500 billion bet on AI's future.

The Journey
- Born in 1957 on a "dirt track with no name" in Kyushu to Korean parents in poverty
- Endured bullying and discrimination as a "Zainichi" outsider in postwar Japan
- Made a teenage vow to become Japan's most successful businessman
- Moved to California at 16, following McDonald's Japan founder Den Fujita's advice
- Built his first fortune at 19 by selling a pocket translator patent for $1.7M
- Founded SoftBank in 1981 as a floppy disk distributor

The Evolution of Vision
- 1976: "I'll make $10,000/month working 5 minutes a day through invention"
- 1981: "SoftBank will be a billion-dollar company" (declared to two employees who quit)
- 1995: "We'll become the venture capital arm for the internet revolution"
- 2000: "We'll back the next generation of global tech giants"
- 2017: "We'll fund the next age of innovation with the world's largest tech fund"
- 2025: "AI infrastructure will reshape everything - let's build it"

Overcoming Obstacles
- Survived the dot-com crash that erased $70 billion of wealth (97% of his fortune)
- Battled chronic hepatitis in the mid-1990s while hiding illness from investors
- Endured Vision Fund losses of $18 billion in 2020, one of history's worst annual losses
- Faced activist investor criticism over poor transparency and results
- Weathered multiple market crashes and company failures across decades

Today's Impact
- $17 billion net worth (as of 2025)
- SoftBank: Global technology investment powerhouse
- $100 billion Vision Fund: World's largest tech investment vehicle
- Alibaba investment: $20M stake became worth over $70B
- Co-leading OpenAI's $500B "Stargate" AI infrastructure project

Growth Strategies That Worked
- Vision-First Investing: Backed founders with "sparkle in their eyes" over rigid business plans
- Market Share Over Profits: Lost money initially on broadband and mobile to dominate markets
- Massive Scale Bets: Used size and capital to intimidate competitors and secure deals
- Long-Term Thinking: Created a "300-year vision" for SoftBank's future
- Resilience Over Caution: Treated every failure as fuel for the next big bet

Key Milestones
- Sold Space Invaders arcade machines in the US, earning $1M profit in six months
- Took SoftBank public in 1995 with $1B in annual sales
- Invested $40M in Yahoo, turned it into $808M in months (18x return)
- Briefly became world's richest person in 2000, surpassing Bill Gates
- Lost $70B in the dot-com crash - "biggest personal loss in history"
- Bought Vodafone Japan for $20B just to become iPhone's exclusive carrier
- Launched $100B Vision Fund in 2017 with Saudi Arabia's backing

The Philosophy

"Too much guts, I lose a lot of money, but vision trumps convention. If I had listened to cautious advisers, we would never have done the Alibaba deal."

"Life is short, so we need to get bigger, faster, crazier. One big winner can mask all the other failures combined."

"We're not just investing in companies, we're funding the next age of human innovation. Whether it's AI, telepathy networks, or technology that lets people talk to their pets, we're playing the very long game."

Founder story 2

See how Matt and Lauren out a $1 Million loan to buy a movie theater. Now it brings in $550K a year

Matthew McClanahan (35) and Lauren McChesney (41) bought Shankweiler's Drive-In Theater in Pennsylvania after it was listed for sale for 6-7 years. They scraped together funds including a $1M SBA loan and seller financing to purchase the historic venue in November 2022.

Key Business Insights:
- Theater is only profitable 4 months per year (June-August carries the entire operation)
- Film licensing costs 50%+ of ticket revenue and represents their biggest expense
- First year they barely paid themselves; year two brought regular salaries
- They operate year-round unlike most East Coast drive-ins to maintain some revenue flow

The Reality: 
Two weeks after purchase, their projector failed spectacularly. With no working capital or technical expertise, Matthew had to learn repairs himself. Despite the constant stress and questioning, seeing hundreds of families enjoy the nostalgic movie experience reminds them why they're preserving this piece of Americana.

Bottom Line: 
Sometimes the most meaningful businesses aren't the most profitable - they're the ones that bring communities together and preserve cultural experiences for future generations.

Founder story 3

Alex Zaccaria, Anthony Zaccaria & Nick Humphreys: From Music Marketing to $37M Revenue with Linktree.

From Music Industry Insiders to Digital Pioneers: How Three Australian Entrepreneurs Created a Six-Hour Solution That Reached $37M Annual Revenue and $1.3B Valuation Transforming How Millions Share Their Digital Presence.

The Journey
- Raised in Australia's music industry through parents' musical instrument business
- Started managing club nights and artists while studying entrepreneurship
- Brothers Alex and Anthony each led separate music projects before joining forces
- Partnered with Nick Humphreys to bridge the digital marketing gap in music
- Launched Bolster, a successful digital marketing agency for festivals and artists
- Built Linktree in just six hours as a side project in 2016
- Scaled from 7 to 230+ employees globally during hyper-growth phase

The Evolution of Vision
- 2016: "Why can artists only share one link in their social media bio?"
- 2017: "Let's create a simple multi-link solution for the music industry"
- 2018: "This could work for all creators and influencers, not just musicians"
- 2020: "We can democratize digital identity for everyone"
- 2024: "Building the premier online presence aggregator for individuals and businesses"

Overcoming Obstacles
- Initially targeted only existing agency clients before viral growth began
- Had to pivot from music-focused tool to universal digital solution
- Managed explosive growth from 10 daily users to 10,000 signups per day
- Balanced maintaining free service while developing sustainable revenue model
- Navigated platform dependencies and policy changes from social media giants
- Faced competition from Instagram and other platforms copying core features
- Built global team while maintaining bootstrapped profitability for four years

Today's Impact
- $1.3 billion company valuation
- $37 million annual revenue (2023)
- 10,000+ daily new signups
- 35+ million users globally (90% outside Australia)
- 39 app integrations and growing ecosystem 230+ employees across global offices

Growth Strategies That Worked
- Product Hunt Launch: Early user showcased platform, leading to viral adoption by Alicia Keys
- Freemium Model: Generous free tier with premium features for power users
- Word-of-Mouth: Leveraged existing music industry network for initial traction
- Timing Advantage: Launched during transition from chronological to algorithm-driven social feeds
- Community Focus: Built around democratizing digital access for all users
- Strategic Funding: Remained profitable while bootstrapped, then raised $120M+ for acceleration

Key Milestones
- Started as six-hour side project while running successful marketing agency
- Gained 3,000 users overnight through Product Hunt feature and celebrity adoption
- Achieved consistent 800+ daily signups baseline after viral moment
- Launched PRO subscription in April 2017, confirming product-market fit
- Maintained bootstrapped profitability through 2020 with $10M annual revenue
- Raised Series A of $10.7M in 2020 from Airtree Ventures and Insight Partners
- Secured $110M Series B in 2022, reaching unicorn status at $1.3B valuation

The Philosophy

"Our mission is to equalize the digital realm, making the internet and digital identity accessible to all, thus championing a more democratized online world."

"The story of Linktree teaches us that astute observation of market gaps combined with execution speed can create an indispensable tool, even when starting with the simplest of functions. It reinforces the notion that with precise targeting and a user-centric approach, even a basic concept can blossom into an enterprise with a global footprint."

 Founder note from Brad Mac

21 marketing lessons from Rory Sutherland (and the last one might be the most valuable).

1. A flower is simply a weed with an advertising budget

2. The opposite of a good idea can also be a good idea

3. People don’t think what they feel, don’t say what they think, and don’t do what they say.

4. Solving problems using rationality is like playing golf with only one club.

5. Trust grows at the speed of a coconut tree and falls at the speed of a coconut.

6. The nature of our attention affects the nature of our experience.

7. Don’t design for average.

8. The problem with logic is that it kills off magic.

9. Benchmarking can stifle the ability to differentiate.

10. Without the element of surprise when providing information, you don’t get attention.

11. Creative ideas come from inspired acts of observation.

12. Highly targeted advertising merely finds customers; less well-targeted advertising can create customers.

13. Not everything that can be counted counts, and not everything that counts can be counted.

14. Never call a behaviour irrational until you really know what the person is trying to do.

15. If we allow the world to be run by logical people, we will only discover logical things.

16. Buyers usually care less about seeking perfection and more about avoiding catastrophe.

17. Consumer research is great at telling you what people did; it’s terrible at telling you what people will do.

18. Perception can alter value and purchase decisions more than physical attributes.

19. What gets mismeasured gets mismanaged

20. It doesn’t pay to be logical if everyone else is being logical.

BONUS: Test counterintuitive things, no one else will.

 A founder note we loved

All done for today. See you in 7 days.

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See ya.

Guy + Farzan
Founderoo