Happy Friday.
Here’s my October playlist. Enjoy!
Timing Your Raise
Raising money isn’t about survival—it’s about knowing exactly what unlocking that capital will do, whether it’s shipping products faster or extending runway to outlast competitors. The fatal mistake is raising too early (giving away 25%+ for a slide deck) or too late (missing your market window), so aim for the “smart time” when you have an MVP with usage, early revenue, and signs of product-market fit that prove capital will accelerate proven traction. Structure matters more than founders realize: SAFEs move fast but can stack up and create brutal dilution if your cap is too low, while priced rounds take longer but set a clean baseline—so choose based on what creates the least friction for your next raise, not what sounds impressive. The real work starts post-raise when you must ruthlessly manage burn, hit milestones, and communicate transparently with investors who become partners, because raising at a valuation you can’t grow into within 12-18 months turns your seed round into a down-round trap. The Founders Corner (8 minutes)
VC Heard Mentality
The best VCs claim to win by being contrarian, yet half of Benchmark’s deals include another top-tier firm as a co-investor. Data from the top 20 venture firms reveals that 40% of their investments are syndicated with peers, with firms like Benchmark, Redpoint, and Greylock leading the pack in co-investing behavior. The pattern suggests many elite investors prioritize risk-sharing and social proof over concentrated conviction, despite the industry’s rhetoric about independent thinking. This consortium approach may optimize for career safety rather than genuine alpha generation—raising questions about whether top-tier syndication represents strategic wisdom or herd mentality dressed up as validation. Substack (2 minutes)
The $100K Talent Tariff
Pricing innovation at $100,000 per visa application doesn’t protect American jobs—it just ensures the best engineers build the next generation of AI companies in Toronto and London instead of San Francisco.The Whitehouse’s H-1B fee hike from $5,000 to $100,000 creates a two-tier system where Big Tech can afford global talent while startups are forced to either abandon critical hires or shift operations overseas entirely. Founders whose companies were built by H-1B holders (including co-founders and heads of engineering who led to successful exits) now face an impossible math problem: one U.S. visa costs the same as hiring 20 remote engineers abroad. The policy achieves the opposite of its stated goal—rather than bringing jobs to America, it’s accelerating the export of entire startup operations to countries that welcome immigrant talent without six-figure gate fees. TechCrunch (6 minutes)
Founder FAQ: What IP Should Be Prioritized By Startups With Limited Resources?
Most startups waste precious capital on patents when their competitive moat actually lives in trade secrets that cost almost nothing to protect and last forever. Trade secret protection is immediate (no multi-year patent process), costs nearly zero (just confidentiality agreements and security measures), and covers things patents can’t—like proprietary algorithms, customer databases, and business processes that competitors can’t reverse-engineer if you never disclose them. Trademarks should come second because it’s devastating to build a product around a brand only to have it stripped away by an infringement claim, so protect your company name first, then file for logos and taglines when revenue comes in. Patents rank third for resource-constrained startups since they’re expensive (attorney fees plus maintenance costs), time-consuming (years to grant), and uncertain (examiners may reject them)—but filing a provisional patent application buys you a priority date and “patent pending” status for a fraction of the cost, giving you 12 months to test market demand before committing to the full application. Westaway (7 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
Built By Founders for Founders
I co-founded my first startup with friends in 2007. As a founder, I struggled to find an affordable law firm that was designed for early-stage startups. So, I created one myself. Westaway is a law firm built by founders, for founders. If you’re ready to ditch the outdated billable hour model and try a new approach to legal services that saves you time and money, let’s talk. I’d love to jump on a 15-minute call to show you how we can make legal work smooth, fast and cost-effective for your startup. Schedule a call with me now.
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