Founder Fridays No. 137
The Shopify AI Memo -- The Three-Person Unicorn -- Boredom Breeds Brilliance
Happy Friday.
2025 Startup Legal Survey
Fellow Founders and Operators,
There's a critical gap in startup knowledge: no publicly available data exists to understand what 'normal' legal spend looks like at different stages. Today, I'm changing that by launching the first (hopefully annual) Startup Legal Survey, and I need your help. Will you take a moment to fill out the survey please?
This anonymous survey contains just 18 multiple-choice questions, is mobile-optimized, and takes less than five minutes. You can easily complete it while waiting in line at the coffee shop. As a thank you, you can opt to receive a custom benchmarked report showing how your legal approach compares to similar-stage companies.
Your insights will help build the resource we all wish existed. Be part of creating this essential startup tool that will help founders make smarter legal decisions for years to come. Click the button below to take the survey. I greatly appreciate it.
The Shopify AI Memo
While many bosses merely tolerate artificial intelligence use, Shopify's Tobi Lütke is making it a requirement for continued employment at the company. Using AI effectively is now a fundamental expectation for everyone at Shopify — not just a suggestion but a requirement tied to their core values of constant learning and thriving on change. The most successful team members are achieving 100 times productivity by reflexively incorporating AI into prototyping, problem-solving and ambitious tasks that wouldn't have been attempted before. Before requesting additional resources or head count, teams must demonstrate why they cannot accomplish goals using AI tools that have been made readily available across the organization. @tobi (6 minutes)
The Three-Person Unicorn
While many founders still equate scale with head count, a new breed of AI-native startups are proving that small has become a compounding advantage in the race to more than a $100 million annual recurring revenue. Companies like Cursor, ElevenLabs and Mercor are achieving unicorn status with just 30–50 employees by leveraging AI to handle everything from development and sales to marketing and customer service — creating a virtuous cycle where fewer people means less politics, fewer meetings, faster decisions and less dilution. The ideal three-person unicorn team consists of an aggressive visionary CEO, a "words person" with empathy and psychology insights, and a "numbers person" obsessed with metrics — all generalists capable of juggling multiple roles and leveraging AI as a force multiplier. Biology's concept of allometric scaling now applies to startups: as AI handles the repeatable, consistent work while humans focus on outlier creativity that machines can't replicate. NFX (10 minutes)
Boredom Breeds Brilliance
What if the notification-free silence you've been avoiding is actually the gateway to your next breakthrough idea? Digital fasting — deliberately unplugging from all devices for predetermined periods — combats the "always on" mentality that research shows isn't actually making you more productive but is actively depleting your cognitive resources and creativity. Even Bill Gates famously isolates himself for "Think Weeks" where he simply reads and thinks, while entrepreneurs like Aytekin Tank find their greatest inspirations while working on family olive farms in Turkey, far from digital distractions. Start small with one-hour breaks, work up to full-day "digital sabbaths" and watch as your mind begins to wander into surprising new territories of innovation that no amount of scrolling could ever produce. Entrepreneur (5 minutes)
Founder FAQ: Workers at My Startup Are Willing to Work for Equity Only. Is that OK?
Eager employees willing to work for stock alone might seem like a startup founder's dream, but this arrangement could become your legal nightmare. Federal and state labor laws absolutely require employees to receive at least minimum wage plus overtime (for non-exempt workers) before any equity compensation can be considered — making equity-only compensation for employees explicitly illegal under U.S. law. While independent contractors theoretically could be paid solely in equity, this creates a dangerous risk of worker misclassification claims that could result in crippling back taxes, wage penalties and civil fines reaching back years. Smart founders understand that equity works best as a supplement to required cash compensation, designed with proper tax planning and legal guidance to align interests without triggering compliance disasters. Westaway (4 minutes)
Startup Funding Guides
I’ve put together a series of guides to equip founders to excel at fundraising. These guides break down the deal term-by-term and give you negotiation tips so that you can speak to investors with confidence.
Convertible Note: Guide / Video
Certainty in an Uncertain World
The startup journey is filled with uncertainty. A fractional General Counsel provides the certainty of on-call legal expertise. Having an experienced GC gives founders invaluable peace of mind. With a seasoned startup legal expert on demand, founders have a steady guide through uncertain legal terrain. The GC acts as a trusted strategic advisor while handling day-to-day legal tasks. This lifts a huge burden off of startup leaders, allowing them to focus on growth with legal confidence. Rather than getting bogged down in legal details, founders feel empowered delegating tasks to an expert and focusing on their vision. Founders sleep better knowing their GC can swiftly handle any legal issue that arises. If you’re curious how a fractional GC can give you peace of mind, let’s talk.
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