This Week in Startups
This Week in Startups

Best of This Week in Startups: Week of November 9th, 2020

E1136 featuring SEC Commissioner Hester Peirce: https://rb.gy/pndfna E1137 featuring Repl.it's Amjad Masad: https://rb.gy/ypwjd2 E1138 Ask Jason!: https://rb.gy/hzsutw Follow Jason: https://linktr.ee/calacanis

Featured Speakers

Jason Calacanis Host

Topics Discussed

Episode Summary

Executive Summary: The episode covers two major themes: SEC Commissioner Hester Peirce’s openness to more flexible pathways for accredited investor access, paired with strong warnings about scams, diversification, and due diligence; and Replit CEO Amjad Massad’s view that AI will first augment programmers rather than replace them, while full automation of programming could trigger dangerous, runaway intelligence growth. Jason also argues solo founders can be just as compelling as multi-founder teams, with founder quality and product-market fit mattering far more than team count.

Main Topics: Expanding access to investing and accredited investor rules: Hester Peirce discusses Jason’s proposal for using Angel University as part of a test to qualify as an accredited investor, noting the SEC is open to ideas and that capped investment models already exist in crowdfunding. Investor caution, diversification, and scam awareness: Peirce stresses that people should not concentrate all risk in one basket, should only invest what they can afford to lose, and must watch for red flags and fraud when evaluating investments or investment tests. AI’s near-term effect on developers: Amjad Massad says AI will most immediately make programmers more effective and expand access to programming, rather than fully replacing developers in the near term. The risk of fully automated programming: Massad argues that if machines can program themselves, it could lead to an intelligence explosion, centralize power, and create a highly risky future. Solo founders versus multi-founder startups: Jason answers a listener question by arguing that founder count is less important than idea quality, execution, and customer love, though very large founding teams can create governance and dilution issues. Founder dilution and equity structure: Jason explains how multiple founders can end up with too little ownership after dilution, and why top-offs or retention mechanisms may be needed to keep a founder committed.

Key Arguments: Peirce supports exploratory pathways for investing education/qualification but insists on caution, due diligence, and consumer protection. She emphasizes diversification across both investments and career risk, warning against overconcentration in employer equity. She sees capped investment amounts as reasonable in some contexts, citing crowdfunding as an existing example. Massad believes AI will first boost programmer productivity and access, not eliminate developers immediately. He warns that true self-programming AI could trigger an intelligence explosion and concentrate power dangerously. Jason rejects the idea that solo founders are inherently inferior; he prioritizes product quality, execution, and customer demand over founder count. Jason argues that large founding teams can cause infighting and create messy equity splits, while solo founders can be faster and more decisive. He notes that founders with too little equity may lose motivation, making vesting top-offs or retention grants strategically important.

Data Points: Episode number: 1136, 1137, 1138 - Three consecutive episode segments referenced in the transcript Crowdfunding cap model: Limited investment amounts - Peirce cites crowdfunding as an example of existing caps on how much people can invest AI timeline: "Definitely decades away" - Massad’s estimate for AI reaching programmer-replacing capability AI horizon: "Two or three decades" - Massad says this time frame can pass quickly and still matters for future risk Founder grant model: $8K per founder - Jason references Paul Graham’s early Y Combinator funding approach Ramen funding example: $16K for two founders - Based on $8K per founder in the YC model Jason described Ramen funding example: $24K for three founders - Based on $8K per founder in the YC model Jason described Example investment: $25K–$50K in / about 4x return - Jason describes a Reportive investment outcome as modest from his perspective Founder equity threshold: 30%–40% - Jason says this is a typical sign of a solo founder-level ownership stake Multi-founder equity: 10%–20% each - Jason says this is common for two- or three-founder teams Dilution example: 20% - Jason uses 20% dilution as part of his ownership math example VC ownership example: 30% - Jason mentions venture capitalists taking 30% in a hypothetical capitalization scenario Employee equity example: 10% - Jason includes 10% employee equity in his dilution illustration Founder ownership example: 12% each - Jason describes five founders each owning 12% before dilution in a sample scenario Top-off example: 5 points over 5 years - Jason recounts proposing an equity top-off for a founder at 11% ownership Second founder example: 15% ownership - Jason describes another founder who wanted a top-off to 25%

Pivotal Quotes: "diversification is a way to protect yourself" — Hester Peirce: She warns investors not to concentrate investments and career risk in the same company "I think the most immediate thing that AI will do is we'll make programmers more effective, more efficient" — Amjad Massad: He describes AI as a productivity multiplier before it becomes a replacement technology "there's so many more important things to think about with a startup. How good is the idea? How good is the execution of that idea?" — Jason: He argues founder count matters far less than product quality and execution

Implications: Listeners should expect more debate over investor-access rules, stronger emphasis on scam awareness, and continued AI augmentation before replacement. For startups, founder quality and ownership structure matter more than team size.

From the Episode

Out what the right answer is here. We need to draw on the wisdom of everyone out there, people who have been in the investing world and who know the kinds of information that people need to know before they invest. On episode 1137, Replit CEO Amjad Massad explained AI's immediate impact on developers and if it could ever replace them entirely. I think the most immediate thing that AI will do is we'll make programmers more effective, more efficient, and will. Continue to increase the access to programming, kind of in the same way that Replit does that. We continue to look at it and invest in it. And at some point, we're probably going to build something there. But I don't see it. So, if you replace programmers, that's the last job you have to replace. Because think about it: if the machine can program itself, then you get into what AI researchers call intelligence. Explosion because you have an AI that is programming itself to get better. And so maybe an AI programs, it's sort of the next version that is better of itself. And then the next version is programming the next version. And then you have a runaway explosion. And then we invented God. So it is, if programming gets automated, it's the last job of.

Amjad Massad · at 4:00

You guys work for three or four months. If it works and it works out great. If it doesn't work, it doesn't work. So that's why you have this addiction to the multi-founder approach. I don't care because there are maniacal people who are exceptional founders, who are so good that for them to have a co-founder would only slow them down. What co-founder in the world is going to be able to keep up with Mark Zuckerberg? Come on. What founder in the world, what co-founder is going to be able to keep up with Elon Musk? You know, like Steve Jobs had Woz. That was actually a true co-founder because he needed a technical person at that time. And so in some cases, it's just much better to not have co-founders. When it is, it is good because it creates redundancy. It is bad because sometimes. It creates

Jason · at 10:43

With the idea that people should be able to invest their money as they choose. I get very uncomfortable when we're trying to micromanage people's finances, but I can see that I have to work with colleagues who are maybe more conservative than I am in that regard, and they would like to put some breaks in place. So I can see that kind of thing being attractive to people, and that gives you a little chance to practice maybe investing small amounts. I would say, even if the government Government doesn't tell you that that's how you should approach things. It's really good idea to be cautious in how you approach things. Don't jump in with, don't empty out your bank account and jump in with both feet to invest in something unless you're really sure what you're doing. You really need to be careful. And there are a lot of people out there who are just waiting eagerly to steal your money. So that brings me to the final concern that I would have about.

Hester Peirce · at 1:30
🔓 Sign Up for Unlimited Episode Search

About This Week in Startups

Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.

View all episodes from This Week in Startups