Founder Fridays No. 157
AI Kills Search Ads? -- Bootstrapping Beats Credentials -- Speed First, Moats Later
Happy Friday.
AI Kills Search Ads?
Google could lose 95% of search volume and still print money—but only if it keeps the queries that actually convert to purchases. AI assistants are already devouring the low-value informational searches (like "how many protons in cesium") while leaving the profitable commerce queries intact, but this honeymoon period won't last forever. The real disruption happens when AI starts replacing "best laptop for programming" searches, forcing a complete reimagining of how we discover and buy products. Amazon and Shopify are positioned to survive this shift because they own the transaction layer, not just the discovery phase. a16z (12 minutes)
Bootstrapping Beats Credentials
A 17-year-old high school dropout with zero industry connections built a billion-dollar restaurant platform by charging 40x more than competitors—and customers happily paid because the ROI was undeniable. Adam Guild's secret wasn't fancy credentials or VC backing; it was obsessing over customer outcomes so intensely that premium pricing became a forcing function for excellence. The pandemic that killed his dining-focused product became the catalyst for explosive growth when he pivoted to online ordering, proving that existential threats often reveal your customers' most urgent needs. His bootstrap-first mentality created unshakeable discipline around profitability and customer intimacy that venture funding later amplified rather than replaced. First Round Review (15 minutes)
Speed First, Moats Later
Building defensible AI companies requires sequential strategy deployment—not everything at once. Most founders obsess over network effects from day one, but the real winners master a "motte-and-bailey" approach: use fast-deploying advantages like distribution and brand to capture market position quickly, then retreat to deeper defensibilities like network effects and embedding when competition intensifies. The companies that survive this AI boom will be those that recognize when to fight for rapid growth in the "bailey" and when to build impregnable "motte" defenses. Your early defensibility should maximize speed; your long-term defensibility should maximize stickiness. NFX (11 minutes)
Founder FAQ: What’s the Deal with Copyright?
Most founders obsess over patents and trademarks while ignoring the simplest IP protection that costs less than a nice dinner. Copyright protection kicks in automatically the moment you create something original, but registering it for under $100 unlocks the ability to sue for damages and collect attorney fees—turning your legal protection from a paper tiger into a real weapon. Your code, marketing materials, and product documentation are literary works that deserve the same protection as bestselling novels. The biggest mistake isn't failing to file; it's discovering too late that you can't enforce what you never registered. Westaway (8 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 (GC) 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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