E1138: Ask Jason! Benefits to growing a company internationally, Apple’s new chip impact, investing in solo founders & more!

Episode Summary

Executive Summary: This Ask Jason episode covers practical startup and investing advice: when non-US startups should expand to the US, whether solo founders are viable, how angel investors should size bets, how to grow a podcast, the impact of Apple’s M1 chips, and how students can enter entrepreneurship. Jason emphasizes thoughtful strategy, customer understanding, diversification, founder conviction, low-debt optionality, and building products people love.

Main Topics: International startups: when to enter the US market (Priority: 5/5): Jason argues that founders in smaller English-speaking markets should often validate locally first, especially if they want American investors or stealth testing, but should expand to the US when the local market is too small to prove demand. Solo founders vs. multi-founder teams (Priority: 5/5): He says founder count matters less than product quality and execution; solo founders can outperform teams, though multiple founders add redundancy while also increasing conflict and dilution risk. Angel investing portfolio sizing and diversification (Priority: 5/5): Jason recommends broad diversification, using multiple bet sizes, and increasing investment only in companies showing strong growth and clear winner signals. How to grow a podcast (Priority: 4/5): He argues that audience growth follows genuine enthusiasm and great conversations, not forced marketing, and that clips and community engagement are secondary to authenticity. Apple’s M1 chip and vertical integration (Priority: 4/5): Jason explains that Apple making its own chips gives it control over performance, costs, and product integration, but the transition will take time and may benefit from Apple’s data advantage. How students can enter entrepreneurship (Priority: 5/5): He encourages young people to build projects early, avoid excessive student debt, and focus on skills, shipping, and action over credentials.

Key Arguments: Founders outside the US should often exploit their local market first because it can provide stealth, cheaper talent, and proof points before approaching American investors. American investors care less about geography than about whether a founder can demonstrate thoughtfulness, market understanding, and real traction. Solo founders can be ideal when one exceptional person can move faster than a team; the main downside is lack of redundancy if they burn out or leave. Multi-founder teams often fail due to infighting, and too many founders create serious dilution and control problems. Angel investors should diversify heavily because returns follow a power law: one or two outcomes drive most of the portfolio’s upside. A good angel strategy is to use different check sizes and reserve capital for clear winners that are showing real growth. Podcast success comes from loving the conversation and the topic; audience growth is a consequence of authenticity, not the primary goal. Young people should prioritize building products, developing skills, and minimizing debt so they can take risks and keep optionality. Apple’s chip strategy is valuable because it captures margin, improves integration, and lets the company optimize hardware based on user data. Vertical integration can be a long-term advantage, but it requires scale, patience, and years of execution to pay off.

Data Points: Australia population: 25 million - Used as an example of a smaller English-speaking startup market Canada population: 25–30 million - Compared with the US as a similar but smaller market Ireland population: 5–10 million - Used to illustrate small English-speaking markets LinkedIn B2B marketer effectiveness: Over 78% - Ad read citing LinkedIn as the most effective social platform for B2B objectives LinkedIn decision makers: Over 62 million - Ad read describing LinkedIn’s reach Masterworks waitlist: 25,000 people - Ad read promoting skip-the-waitlist offer Melanie/Canva episode reference: Episode 939 - Jason references a previous podcast with Canva’s founder Canva episode date reference: May 2019 - Context for earlier interview with Melanie Angel List first syndicate community size: 300 people - Jason describes early syndicate growth after investing via AngelList Current syndicate size: Over 5,000 people - Jason says his syndicate has grown substantially Syndicate growth rate: 500 a month - Reported growth of his syndicate community Podcast cadence: 150 episodes a year - Jason describes current output cadence Fordham tuition (historical): $9,000–$10,000 a year - Jason compares older college costs to modern tuition Current Fordham tuition reference: $65,000 a year - Jason cites contemporary tuition as an example of rising higher-ed costs Early college debt: About $6,000 - Jason says he paid off his own debt quickly Student loan benchmark: Under $50K annual income - Jason suggests borrowers under this threshold should get temporary relief Ramen funding: $8K per founder - Jason references Paul Graham’s early YC-style funding approach Example angel investment: $25K–$50K - Jason describes putting this amount into an early company and receiving roughly 4x back Launch accelerator initial check: $100K - Jason invites the Australian founder to apply if traction reaches a threshold

Pivotal Quotes: "I don't need to know if your idea is going to succeed. I need to know if you're going to succeed." — Jason: On how investors evaluate founders beyond the specific market or idea "Scared money don't make money." — Jason: On angel investing and the need to take prudent risks "If you don't love it, there's no way the audience is going to love it, they'll see right through it." — Jason: On podcasting and why authenticity matters more than growth hacks

Implications: Listeners should prioritize proving real traction, preserving optionality, and making thoughtful decisions over chasing prestige or speed. For founders and investors, execution, conviction, and diversification matter more than rigid rules about team size or geography.