Happy Friday.
Fundraising Season Is Open
Your pitch isn’t the only thing deciding if you raise — the calendar is quietly working against or for you, and most founders never check it. VCs move fast when they feel urgency and slow to a crawl when they don’t, and that urgency clusters in two windows a year: January to spring break, and Labor Day to Thanksgiving — which means the “hot” season most founders wait to notice just opened. So this week, map your target list of specific partners (not firms), get your data room and narrative tight now, and time your outreach to land multiple investors in “term-sheet-ready” territory in the same two-to-three week stretch instead of trickling meetings out over months. Do that, and you turn a slow, one-at-a-time pitch process into real competitive pressure — the kind that gets you better terms, a faster close, and a term sheet before you’re forced into a down round or a season you can’t afford to skip. NFX (8 minutes)
AI: Sustaining or Disrupting?
Is AI a sustaining innovation or a disruptive one? The answer looks like both at once, strengthening incumbents in some ways while undercutting them in others, which is unusual for a single technology. For established companies, adoption depends on human initiative, and that agency gets constrained by risk-averse calculus favoring the downside over pushing into the unknown. Startups face the opposite incentive, since failure is already the default outcome, so leaning hard into AI is pure upside with little to lose, which is why founders willing to go all-in on automation are positioned to outmaneuver incumbents still keeping humans in the loop. Stratechery (6 minutes)
What Actually Drives Founders
Forget the billionaire dream — Paul Graham says the thing that gets founders out of bed isn’t the payoff, it’s the fear of looking like a fool when the server crashes. That distinction matters because motivation built on avoiding disaster is more durable than motivation built on a future payday; it’s what keeps you working the unglamorous, unrewarded middle years before anyone thinks you’re impressive. This week, stop measuring your team’s urgency by the size of the outcome you’re chasing and start asking what specific failure you’re each most afraid of right now — then fix that thing first. Anchor your daily execution to concrete disasters you’re avoiding instead of abstract wins you’re chasing, and you’ll find the grind easier to sustain on the days the big vision doesn’t feel real. Youtube (5 minutes)
Founder FAQ: Why Understanding Types of Acquisitions of Startups Is Important?
Your acquisition price isn’t set by your revenue or your traction — it’s set by which of three totally different buckets you fall into, and most founders never figure out which one they’re actually in. A team buy pays $1-3M per engineer for talent, a product buy pays $5-500M to fill a roadmap gap, and a strategic buy can hit $20B+ for something the acquirer simply can’t replicate — same company, wildly different number depending on what the buyer actually wants. This week, if you’re even loosely exploring an exit, write down the honest answer to “why would someone buy us” in one of those three categories, then check whether your pitch, your metrics, and who you’re even talking to actually match that category. Get that alignment right and you negotiate from a position of strength instead of hoping the buyer values you the way you value yourself — get it wrong and you leave real money on the table before the conversation even starts. Westaway (5 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.