Happy Friday.
AI Beats Hiring
What if your best engineer got outpaced by an AI agent you called a "bad intern" just months ago? Linktree chose to scale talent instead of headcount in 2025, keeping their team flat at 190 people while dramatically increasing product velocity through aggressive AI adoption. The key wasn't just deploying tools—it required treating AI agents like junior team members who need proper management, context, and realistic task sizing. Senior engineers emerged as the most effective AI users, not because of technical prowess, but because they understood how to delegate and provide sufficient context, skills they'd developed managing human teams. Linktree (12 minutes)
It’s Pitch Season
Most founders obsess over their deck while ignoring the calendar—but VCs make faster decisions when they're focused, in town, and feeling competitive pressure. The fundraising calendar has two hot seasons (January-March and September-November) when investors are most active, plus a weird summer period where deals still happen but with less competition for attention. Smart founders plan for 12 months, prep for 9 months, then execute lightning-fast during a single hot season to create momentum and "hotness" around their deal. The key insight: your ability to orchestrate timing and urgency often matters more than having the perfect pitch. NFX (8 minutes)
ROI Beats Hard Work
The difference between promoted managers and stuck ICs isn't work quality—it's knowing which work actually moves the needle on business metrics that matter. Most people confuse inputs (hours worked) and outputs (dashboards built) with actual impact (revenue driven or costs saved), but senior roles require translating every initiative into ROI calculations using driver trees. The secret framework: define your return metric, map the lever you're moving, build out all other factors that affect your target through MECE breakdowns, then model the ripple effects with explicit assumptions you can iterate on. Smart operators size everything in a common currency (usually revenue) so they can stack-rank initiatives and avoid working hard on projects that go nowhere. Diving Into Data (12 minutes)
Founder FAQ: What’s the Importance of Trademark in a Startup?
Your domain name registration doesn't give you trademark rights—a costly misconception that destroys startups overnight. Trademarks protect your brand identity across specific industries, provide legal recourse against copycats, and can dramatically increase your company's value to investors and acquirers. The process involves conducting thorough searches through USPTO databases, filing applications ($250-$350 plus $3,000-$5,000 in legal fees), and actively monitoring for infringement once registered. Most founders skip the monitoring step, but failing to enforce your trademark rights can result in losing them entirely, while trademark infringement can force expensive rebranding and expose you to significant damages. Westaway (6 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
An Innovative Law Firm?
Being listed among Fast Company's “Most Innovative Companies” is an honor for our law firm, yet we believe innovation matters if it actually produces better outcomes for startups. Here’s how we’ve innovated to better serve startups:
Clear Pricing. Traditional billable hours can lead to misaligned objectives and unexpected fees. We've replaced this with straightforward, flat-rate pricing.
General Counsel. Most entrepreneurs want a trusted legal partner, but they hate surprise legal bills. At Westaway, we take care of your startup’s legal needs for a fixed, monthly fee so you can control your costs and focus on scaling your business.
Automation and Artificial Intelligence (AI). We've streamlined our operations through automation and AI (where appropriate), ensuring efficient, high-caliber results.
If you’re an innovative startup looking for an innovative law firm, let’s talk.
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