This Week in Startups
This Week in Startups

Shopify Board proposes share restructuring + The Atlantic's Derek Thompson, Why American Teens Are So Sad | E1433

First we discuss Shopify planning 10-to-1 stock split & increasing CEO/Founder Tobi Luke’s control from 34% to 40% (1:42). Then, the Atlantic's Derek Thompson joins to discuss his piece “Why American Teens Are So Sad” (25:59), including the impacts of new-parenting styles (33:38), social me

Featured Speakers

Jason Calacanis HostDerek Thompson Guest

Topics Discussed

Episode Summary

Executive Summary: The episode opens with Shopify’s proposed 10-for-1 split and a parallel move to boost founder Toby Lutke’s voting control, sparking a debate over whether public companies should resemble founder-controlled private firms. It then shifts to a long interview with Derek Thompson on rising teen depression, arguing that social media, reduced socialization, pandemic effects, stress, parenting styles, and news saturation all interact to worsen youth mental health.

Main Topics: Shopify stock split and founder control: The hosts discuss Shopify’s planned 10-to-1 stock split and a governance proposal that would raise Toby Lutke’s voting power from 34% to 40%, framing it as a founder-friendly move that may deter hostile takeovers and activist pressure. Public-company governance vs founder control: A broader debate emerges over whether public companies should be allowed to retain quasi-private control structures that give founders disproportionate power while still accessing public capital and investor trust. Why American teens are increasingly sad: Derek Thompson explains his Atlantic article on rising teen sadness, highlighting a multi-factor “jambalaya” of causes: social media, isolation, pandemic acceleration, stressful world news, and modern parenting practices. Social media as attention-alcohol: Thompson argues social media behaves like alcohol: beneficial for many but harmful for a susceptible minority, especially teenagers whose peer-sensitive brains and constant negative-emotion exposure make the platforms especially risky. Parenting, resilience, and over-accommodation: The conversation explores whether modern parenting is too accommodating—buffering kids from discomfort instead of building resilience through exposure to difficulty, boredom, and manageable stress. News media incentives and outrage: The hosts and Thompson discuss how news, social platforms, and journalistic incentives can amplify fear, anger, and outrage, potentially worsening anxiety and polarizing public discourse. Practical guardrails for kids and devices: The discussion ends with ideas like age limits, social norms around device use, boredom, and family rules that reduce screen dependence and restore more real-world activity and community.

Key Arguments: Shopify’s split is not just about liquidity or psychological price effects; it also appears designed to preserve founder influence and make hostile takeovers harder. Public markets may be entering a hybrid zone where companies get public capital while founders keep private-company-like control. The stock split itself is largely psychological, because fractional-share access already exists; the governance change is the more consequential part. Teen mental health deterioration is real, not just a survey artifact, because objective indicators like suicides, ER self-harm admissions, suicide attempts, and eating disorders are also rising. Social media is especially harmful because it rewards high-arousal negative emotions and intensifies peer comparison in adolescents. Modern parenting may unintentionally weaken resilience by accommodating fears and discomfort instead of helping kids tolerate stress. News and social media together create a self-reinforcing loop of outrage and fear that can shape young people’s worldview and mood. The best response is not utopian happiness but reducing harmful inputs across several dimensions: screens, isolation, overprotection, and constant doom exposure.

Data Points: Shopify market-cap peak: $212 billion - Shopify reached this peak in November 2021 before falling sharply. Shopify decline from COVID peak: 64% - The company had fallen 64% from its pandemic-era high. Shopify IPO valuation: $1.2 billion - Shopify went public in 2015 at this valuation. Shopify pre-COVID trading level: about $60 billion market cap - Hosts referenced Shopify trading well above its pre-COVID level before the pandemic surge. Current Shopify share price during recording: $605 - Used to explain the effect of a 10-for-1 split on nominal share price. Planned stock split ratio: 10-to-1 - Shopify’s proposed split would reduce the per-share price and increase share count. Toby Lutke voting power before proposal: 34% - Founder and CEO voting power prior to the proposed change. Toby Lutke voting power after proposal: 40% - The board-backed founder share conversion would increase his control. Shopify GMV in 2021: $175 billion - Gross merchandise volume sold through Shopify’s platform. Shopify revenue in 2021: $4.6 billion - Revenue from software fees and take-rate on sales. Shopify net income in 2021: $2.9 billion - Profit cited to show the business is real and substantial. Shopify price/earnings ratio: 27x - Used to frame the company as a high-growth but still expensive stock. Teen sadness/hopelessness trend: all-time high - CDC high-school survey showed persistent sadness or hopelessness at a record level. Rising sadness over a decade: 85% increase - Mentioned as the growth rate in persistent sadness over 10 years. U.S. teen mental health inflection point: 2011-2012 - Thompson linked this period to smartphone penetration surpassing 50% and social media mainstreaming. Instagram/internal product analogy: like alcohol - Thompson described social media as beneficial to many but dependency-forming for some. Average teen screen environment: Apple/Google/Samsung devices throughout the day - Described as a constant companion replacing offline interaction. Shopify founder control target: 40% voting power - Board proposal intended to strengthen founder’s ability to block takeovers.

Pivotal Quotes: "The company is looking to get the influence of our future in Toby's hands." — Robert Ashe: Quoted during the Shopify governance discussion to explain the rationale for increasing founder control. "Social media is attention alcohol." — Derek Thompson: Thompson’s framing of platforms as broadly useful but potentially addictive and harmful, especially for some users. "Life has suffering and it is pain, and it is our responsibility to determine our emotional reaction to the inevitable pain and suffering." — Derek Thompson: Used in the parenting and resilience segment to argue that kids need exposure to manageable stress.

Implications: Listeners are left with two big takeaways: founder-controlled public companies may become more common, and teen mental health likely requires multi-pronged interventions—less screen time, more resilience, and healthier info diets.

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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.

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