Happy Friday.

An Enduring Company on One Product

Charles Brannock built a company in 1925, refused to ever expand beyond his single foot-measuring device, never took venture money, and it’s still profitable a hundred years later — while Payless, backed by private equity and “modernized” with debt, went bankrupt and disappeared. The lesson isn’t nostalgia, it’s that relentless focus on making one thing well, funded by real revenue instead of leverage, builds something that survives market shifts and cheap knockoffs because customers can feel the difference in quality. This week, pick the one part of your product you’d stake your reputation on, and go find where you’ve quietly let quality slip to hit a growth number — a Brannock exec once won a huge account just by showing the buyer a broken competitor’s part next to his own. Do that consistently and you get what most “hot” startups never do: a business that doesn’t need the next funding round or acquisition to survive the next decade. 99% Invisible (18 minutes)

Fix Your Board Slides

Here’s the uncomfortable truth: giving equal weight to all your quarterly goals doesn’t show discipline — it’s a confession that you don’t know how to prioritize, and it’s often how founders accidentally lie to themselves about how much trouble they’re in. A founder with four months of runway who lists “fundraising” and “ship feature X” as equal-sized boxes on a slide isn’t being balanced, they’re avoiding the one number that should be dominating every decision they make. So this week, rebuild your next board slide with sized boxes, not a bulleted list — runway under 12 months means fundraising takes up 95% of the slide in giant font, full stop, and every other goal shrinks to match its actual urgency. Do this and your board meeting stops being theater where you perform “fine” — it becomes the one recurring moment that forces you to check your plan against reality before a shrinking runway turns into a crisis nobody saw coming. NFX (5 minutes)

Never Abandon Your Team

Here’s the part most managers get backwards: when your direct report bombs in front of a board member, jumping in with hard questions or distancing yourself with “well, I don’t agree” doesn’t protect you — it just proves to everyone in the room that you’ll throw people overboard the second things get uncomfortable. The principle is simple but rarely followed: in any meeting, you and your team are always on the same side of the table, because their performance is a direct reflection of your leadership, not a separate event you get to spectate. Before your next high-stakes meeting where someone on your team is presenting, tell them explicitly beforehand — “if this gets heated, I’ll help navigate it” — and agree in advance on which questions you’ll field versus which are theirs, so you’re not improvising loyalty in real time. Do this consistently and you build the kind of trust that makes people want to stay and take risks for you, because they know you won’t let them stand alone when it counts. Stay Sassy (4 minutes)

Founder FAQ: How Delaware Franchise Tax Can Be Helpful For Startups?

That $75,175 Delaware franchise tax bill you just got isn’t actually what you owe — Delaware defaults to the calculation method that makes tiny, pre-revenue startups look massive on paper. This matters because the state gives you two ways to calculate the tax, and almost nobody tells you the second one exists or that it can cut your bill by 99%. This week, before you pay anything, pull your authorized shares, issued shares, par value, and total gross assets, and ask your accountant to run the Assumed Par Value Capital Method instead of just accepting the default Authorized Share Method number. Do this and a company like Gregarious Games — 10M authorized shares, $800K in assets — drops from a $75,175 bill to $350, freeing up real runway for a five-minute phone call. Westaway (3 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.

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: 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:

1. Clear Pricing. Traditional billable hours can lead to misaligned objectives and unexpected fees. We’ve replaced this with straightforward, flat-rate pricing.

2. 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.

3. 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.

Post of the Week

Happy Friday! Welcome to the month August.

Check out the the July 2026 venture capital funding data from AngelList.

Pre-Seed

Median Money Raised:

$1,118,600

Median Post-Money Valuation:

$11,900,000

Seed

Median Money Raised:

$4,221,000

Median Post-Money Valuation:

$33,500,000

Series A

Median Money Raised:

$17,916,800

Median Post-Money Valuation:

$101,800,000

Series B

Median Money Raised:

$29,277,778

Median Post-Money Valuation:

$283,333,333

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.

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: Guide / Video

Should a Seed Round Cost $100,000?

A friend recently told me his relatively straightforward $7 million seed round costs over $100,000 in legal fees — much higher than initially quoted. Unfortunately, this is becoming more common. However, for an experienced startup law firm, a standard seed round based on NVCA docs should cost $20,000 to $40,000 all in. At my firm Westaway, this complete seed round package is a flat $24,000. No runaway legal costs. No surprise bills. Just transparent pricing. If you’ve got an upcoming fundraise, let’s talk.

Happy Friday.

YC Request For Startups

Y Combinator’s Fall 2026 Requests for Startups centers on AI moving into the physical world, with ideas spanning education, defense, eldercare, crypto, compliance, and consumer products, including a first-ever request from the sitting U.S. Secretary of the Army. The batch’s throughline is that AI capability has matured enough to rebuild the systems powering real life, not just digital work. Three standouts: 1) “The Primer” imagines a Diamond Age-style adaptive AI tutor that teaches every child to read, write, and reason at the quality of a devoted private tutor, at consumer scale. 2) “Multiplayer AI” argues that agents are the last major work tool still stuck in single-player mode, and calls for shared live agent sessions that teams can watch, redirect, and hand off together, the way Google Docs beat Word. 3) “Proving You’re Human” tackles the collapse of trust signals in a deepfake era (prompted by a $25M fraud via an all-deepfake video call) by proposing a privacy-preserving verification layer that every bank, app, and call would check before trusting anyone. YCombinator (12 minutes)

8 Reasons People Share

Growth teams obsess over A/B testing headlines and CTA buttons, but the founder who studied 5 million+ users found that sharing is decided almost entirely by psychology, not button copy. Every share is a quiet trade-off in someone’s head — “does this make me look good, and how much effort does it cost me” — and the founders who win growth are the ones who tilt that math, not the ones who just reduce friction. This week, pull up your last three pieces of marketing copy or in-product prompts and check if any of them center the user’s status, identity, or usefulness to their tribe instead of your product’s features — rewrite one line to make sharing about how it makes them look, not how great you are. Get that shift right and you turn casual users into unpaid distribution, because a person sharing to boost their own standing works harder for you than any performance ad ever will. NFX (7 minutes)

Logo Hunt vs. Land Grab

Chasing a Fortune 100 logo can quietly kill your company, even when the deal itself barely moves revenue. Buyers don’t actually buy your vision of the future — they buy either proof that someone credible went first, or math that proves you’ll save them money, and picking the wrong one wastes months your competitors spend closing real deals. This week, ask two questions about your buyer: how much personal or career risk are they taking by signing with you, and does a competitor’s logo actually travel through their network or do they not care who else uses it? If exposure is high and reputation travels (think legal, finance), go land a few trusted names and let them do your selling; if mistakes are recoverable and reputation doesn’t spread (think mid-market ops tools), skip the logo chase and close on ROI at speed instead — get that match right and you stop losing deals to competitors who simply picked the correct game. A16Z (9 minutes)

Founder FAQ: Why Stakeholders Decisions Are Important for a Startup?

Most founders assume they can run the company however they want once the round closes — but the moment you take VC money, your preferred shareholders get a standing veto over a specific list of moves, and most founders don’t find out what’s on that list until they try to do one of them. This matters because protective provisions aren’t boilerplate — they cover things you’ll actually want to do, like issuing new shares, taking on debt, changing your option plan, or expanding the board, and missing one can blow up a financing or an option grant after the fact. This week, pull your actual Series A documents (not a template) and list every action on your protective provisions clause next to your cap table’s approval thresholds, then check it against anything you’re planning in the next two quarters — a raise, a board seat, an ESOP refresh, a related-party deal. Do this now and you avoid finding out mid-negotiation that a routine decision actually needs a shareholder vote you never scheduled. 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.

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: Guide / Video

Is the Billable Hour Right for Startups?

Most law firms bill startups by the hour because that’s the status quo. But while it may work for big companies, the billable hour is likely the wrong model for startups. Why?

1. It incentivizes inefficiency. Firms are motivated to pad hours rather than work efficiently. This adds unnecessary costs.

2. It rewards busywork over results. Startups care about outcomes, not hours logged.

3. Costs are unpredictable. With fluctuating monthly hours, legal spend is hard to budget.

4. It stifles innovation. Hourly billing gives no incentive to find better solutions. Startups need forward-thinking counsel focused on results. That’s why we’ve ditched the billable hour for transparent flat fees.

If you’re ready to explore a law firm with a better billing model, let’s talk.

Post of the Week

Happy Friday.

Here’s my July playlist. Enjoy!

Business Isn’t One Shape

Chouinard built a $1.5B outdoor brand while capping growth at “whatever customers ask for” and taking months off each year to climb mountains — and Buffett got rich buying a dying textile mill and using its cash to invest in stocks, not to scale operations. Both prove the “raise money, grow fast, exit” playbook is just one configuration among many, and most founders never question it because it’s the only story they’ve heard — not because it’s the only one that works. This week, write down the actual tradeoffs you’re accepting under your current model (investor pressure, forced growth rate, time away from your life) and ask whether they’re serving your goals or just the template’s. Do this honestly and you’ll either double down on your current path with real conviction, or spot a version of your business — slower, self-funded, differently structured — that actually fits what you want out of your one life. Commoncog (22 minutes)

AI Didn’t Fix Your Bottleneck

Everyone thinks AI solved the hard part of building a company — it didn’t, it just moved the hard part: going from prototype to shipped, learned, and iterated is now the real bottleneck, not making the thing exist in the first place. Most AI-first teams get faster individually but stay stuck, because speed without cross-team communication just produces more unfinished work, not more shipped product. This week, pick one team and map exactly which tasks are done by a person, which by AI, and which need human review — if you can’t draw that map cleanly, you don’t have an AI-native team, you have people with subscriptions. Do this and you’ll stop mistaking activity for progress, and start measuring what actually matters: how fast you move from V1 to V2, not how fast you generated V1. NFX (6 minutes)

Wold Models

Human brains learn a new skill from a handful of tries while frontier AI models need tens of thousands of examples for the same task — and the gap isn’t more data or compute, it’s that humans build an internal model of how the world works and simulate outcomes before acting, while most AI systems just pattern-match from experience. This matters because “world models” — systems that predict what happens next, not just what to do next — are what let something learn fast from little data, which is exactly the bottleneck holding back AI products in messy, real-world domains like robotics and self-driving. If you’re building or buying AI for your product, this week ask your team one question: is this system predicting outcomes, or just mimicking patterns from training data? — because a model that can simulate “what happens if” will need far less data and adapt far faster than one that only knows “what usually comes next.” Get this distinction right and you’ll spend less on data collection, ship AI features that generalize to situations you never trained for, and avoid over-investing in brute-force approaches that plateau exactly where your competitors’ will too. Youtube (36 minutes)

Founder FAQ: What Is The Procedure of Managing A Startup Cap Table?

Most founders treat their cap table like a spreadsheet chore until it's on fire — but the real risk isn't the spreadsheet itself, it's discovering mid-fundraise that an old equity grant was never properly documented. The cap table isn't admin work, it's the single source of truth investors will scrutinize before they wire money, and a clean one signals you run a tight operation while a messy one raises doubt at the worst possible time. Set a calendar reminder right now to migrate off your spreadsheet onto a platform like Carta, Pulley, AngelList, or LTSE Equity two months before you plan to start raising your next round — not two weeks. Do this and you walk into investor conversations with a cap table that's already clean, instead of scrambling to reconstruct option grants while a term sheet clock is running. 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.

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: 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.

Post of the Week

Happy Firday!

Build a Governance Fortress, Not Just Founder Control

Founder control is the weakest way to protect your startup’s mission because a single person is a guardian with an expiration date, and success makes you vulnerable by turning your company into a target. Eric Ries writes in Incorruptible that this is why Whole Foods couldn’t resist Amazon despite being profitable every quarter it was public. the real defense is a governance fortress, a five-step structural system starting with a Public Benefit Corporation foundation, then a supermajority vote requirement of two-thirds of ALL shares (not just votes cast) so an activist has to win active consent from two-thirds of every shareholder, then a self-reinforcing lock that requires the same two-thirds vote to change the two-thirds rule itself, then a board mission pledge to keep directors focused on mission, and finally outer walls like a classified board, high proxy barriers, and a poison pill. Costco built this in 1985 and held off every attack since. Twilio learned the hard way. when founder Jeff Lawson’s supervoting shares sunset, it took activist investors less than 199 days to force him out because the company had built nothing to protect the mission once founder control expired. The fortress outlives the founder. Forbes (12 minutes)

What Should Founders Never Automate?

Founders are rushing to automate everything with AI, but 95% of AI projects fail to deliver ROI according to MIT’s study of 300 enterprise deployments, and the problem has nothing to do with the tools. The real issue is that most AI budgets went to visible functions like sales and marketing while the biggest measured returns came from invisible back-office operations. A seed-stage founder automated his entire customer support pipeline with a 70% deflection rate and near-instant response time, then discovered six months later that the same feature complaint had been phrased forty different ways in resolved tickets that nobody had read. The AI answered every question politely, so the signal never reached a human, and he lost those customers not because the agent failed but because the answers were good enough that critical product insights disappeared. The breakthrough isn’t picking better tools; it’s learning which functions hold your product-market fit and treating those as the last places to automate, because some conversations are too valuable to outsource to a machine. Venture Curator (18 minutes)

Disney Cracked the Code on Compounding Asset Value

Disney is the most successful enterprise ever created for monetizing human nostalgia because Walt Disney discovered a revenue flywheel in 1928 and then spent forty years perfecting its mechanics into a system that no competitor has ever replicated. He lost Oswald the Lucky Rabbit to a distributor’s betrayal, so he built Mickey Mouse and locked in the brand by slapping “Walt Disney” on every frame, then synchronized sound with Steamboat Willie, which became a global sensation. The real insight came when a theater-led Mickey Mouse Club accidentally scaled to over one million members while a syndicated comic strip reached 100 million readers, and merchandise royalties overtook film revenue in 1934. Instead of squeezing sequels, Disney routed each character’s cultural momentum into secondary nodes like comic strips, music, and licensed watches that reinforced fandom without cannibalizing demand for the core films. Snow White cost $1.5 million, a bet-the-company risk everyone called folly, but it generated $8 million in rentals and proved the model worked. The Disney Vault discovery turned re-releases every seven years into a high-margin growth engine because a new generation of kids had never seen the films in theaters, and by the time Disneyland opened in 1955 as the ultimate monetization engine, the flywheel was compounding across decades. Competitors studied this playbook for a century but failed because they oversaturated franchises with cheap sequels and sold off their back catalogs to satisfy quarterly earnings, structurally preventing the long-term value compounding that requires an obsessive commitment to scarcity and brand prestige. Acquired Briefing (271 minutes)

Founder FAQ: What Is a Cap Table?

Most founders don’t understand their own cap table deeply enough to explain it to an investor, and that gap costs them millions because a cap table is the complete blueprint of exactly who owns what percentage of your company, how many shares each person holds, what those shares cost to purchase, and what happens to everything when you raise money or get acquired. A sloppy cap table that doesn’t track preferred vs. common shares, vesting schedules, option pool allocations, and convertible note conversion triggers will leave you scrambling to close a funding round at the last minute when your investor’s counsel discovers mathematical errors that took six weeks to unravel. The cap table doesn’t just track ownership; it predicts outcomes because it shows you exactly how much dilution your founders and early employees will face in future rounds and whether your option pool has enough shares reserved to actually attract talent without over-diluting the founders into sub-1% ownership. Getting this right before you raise money means knowing your capitalization inside and out so you can negotiate from a position of confidence, spot errors before they cost you a deal, and build a repeatable system for updating the table correctly every time someone earns equity or you close a round. 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.

• SAFE: Guide / Video

• Convertible Note: Guide / Video

• Seed: Guide / Video

• Series A: Guide / Video

Control Legal Spend

Startups suffer from unpredictable legal bills under the billable hour system. Fees fluctuate month to month without warning. Law firms drag out billable hours, but startups foot the bill. Even basic work can lead to surprisingly high legal bills. This unpredictability cripples financial planning. Budgets rarely match actual spend. With utter uncertainty around legal spend, startups cannot forecast or manage burn rates effectively. The antiquated billable hour system fails them. Our General Counsel flat, monthly fee service gives startups cost certainty. Legal spend becomes predictable with bundled services and no surprise overage bills. By switching from hourly to our flat-fee model, startups finally get confident budgeting, accurate forecasting and predictable legal spend. If you’re sick of getting surprise legal bills and are interested in controlling your legal spend, let’s talk.

Post of the Week

Happy Friday.

Don’t Copy, Localize

A century before “product-market fit” was a phrase, Shinjiro Torii built Japan’s biggest beverage empire on one bet: don’t sell the West’s product, rebuild it for your customer’s actual taste. Torii’s first whisky flopped because it mimicked Scotch — the win came only when he stopped imitating and started tuning flavor, packaging, and positioning to what Japanese drinkers actually wanted, a discipline Suntory repeated for a century (gin, coffee, the highball) instead of resting on one hit. This week, pick your most “obviously good” product decision — the one copied from a competitor or a Western playbook — and ask your team where it’s actually a misfit to your customer, not just underperforming. Do this, and you find the tweak that turns a stalled product into a category-definer, the way Suntory turned a failed whisky into a 127-year company by refusing to just copy what worked elsewhere. Town & Country (6 minutes)

Record Funding?

Record venture headlines are lying to you: in Q1 2026, four companies (OpenAI, Anthropic, xAI, Waymo) took 65% of all global VC dollars, meaning “best funding year ever” and “brutal year to raise” are both true at the same time, for different companies. The market didn’t shrink, it polarized — capital piled into a handful of giant rounds while the middle, where almost every real startup lives, thinned out, so benchmarking your raise against headline numbers is comparing yourself to a distorted average that no normal company actually hits. This week, stop pitching against “the market is hot” and instead pull the actual comp data for your stage and sector (seed/Series A round sizes and timelines, not blended totals) so you know the real bar you’re clearing, not the one skewed by nine-figure outliers. Do this and you stop misreading rejection as your problem when it’s actually a structural squeeze — and you position your raise for where the real capital in your bracket still is, instead of chasing a number built for a different game. Venture Curator (5 minutes)

Skip The Model Layer

Everyone assumes AI’s next fortune gets made competing with OpenAI and Anthropic at the model layer — but the smarter startup play right now is going one level beneath them, building the power, materials, and physical infrastructure the hyperscalers themselves are desperate for. The historical pattern is clear: growth never comes from intelligence alone, it comes from intelligence paired with power and coordinated action, and today America has AI intelligence in abundance but is critically short on the power grid and physical execution needed to actually deploy it — which means the bottleneck, not the breakthrough, is where the opportunity sits. This week, instead of asking “how do we build a smarter model,” ask your team “what physical, logistical, or infrastructure constraint is stopping our customers (or our industry) from actually using AI at scale” — and look one layer down the stack from where everyone else is competing. Do this and you position yourself in the part of the AI boom that’s still underbuilt and under-competed, riding hyperscaler-level demand without having to out-fund a hyperscaler. NFX (5 minutes)

Founder FAQ: Why Updating Investors Are Important for a Startup?

Most founders treat investor updates as a status report, but the highest-leverage line in every good template isn’t the metrics chart — it’s the specific ask, the moment you turn passive shareholders into active problem-solvers. Investors who stay engaged month to month are the ones who reinvest, refer new capital, and give real strategic help when you need it, but engagement only happens if you give them something concrete to act on, not just numbers to skim. This week, rewrite your next update so it ends with 2-3 named, specific requests (a warm intro to a named type of person, feedback on a stated problem, a decision you’re stuck on) instead of a vague “let me know if you can help.” Do this consistently and your cap table stops being a spreadsheet of names and starts being a bench of people actually working your problems with you — which shows up fast when you’re back in market for your next round. 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.

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: 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.

Post of the Week

Happy Friday! Welcome to the month July.

As is my annual tradition, here’s my 4th of July country music playlist. It’s 21+ hours of country with the top 10 country songs from 1990-2025 + new stuff I like this year. Enjoy.

Check out the the June 2026 venture capital funding data from AngelList.

Pre-Seed

Median Money Raised:

$1,343,750

Median Post-Money Valuation:

$12,500,000

Seed

Median Money Raised:

$4,064,063

Median Post-Money Valuation:

$36,125,000

Series A

Median Money Raised:

$18,278,438

Median Post-Money Valuation:

$109,125,000

Series B

Median Money Raised:

$31,850,000

Median Post-Money Valuation:

$245,000,000

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.

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: Guide / Video

Should a Seed Round Cost $100,000?

A friend recently told me his relatively straightforward $7 million seed round costs over $100,000 in legal fees — much higher than initially quoted. Unfortunately, this is becoming more common. However, for an experienced startup law firm, a standard seed round based on NVCA docs should cost $20,000 to $40,000 all in. At my firm Westaway, this complete seed round package is a flat $24,000. No runaway legal costs. No surprise bills. Just transparent pricing. If you’ve got an upcoming fundraise, let’s talk.

I started sending Founder Fridays to a handful of clients back in February of 2022. I couldn't have imagined that the community would grow to 50,000+ founders 200 weeks later. Thank you for being part of it, and for sharing it with your friends. To mark this 200th edition, I wanted to break format and do something a little different, zeroing in on the defining issue of our age: AI. Specifically, I want to dig into two essays from Anthropic CEO Dario Amodei, a hopeful one and its deliberate companion nightmare, that together lay out both the staggering upside and the existential downside of this technology. My aim is to take a longer view and wrestle with the question underneath all the noise: will AI elevate humanity, or destroy it?

Machines of Loving Grace

What if we made the next 50 to 100 years of medical progress in just 5 to 10? That single compression is the engine behind Anthropic CEO Dario Amodei’s vision of an AI-transformed world. He argues that most people underestimate the upside of powerful AI just as badly as they underestimate the risks, and that he focuses on the dangers precisely because they are the only thing standing between us and a radically better world. He avoids the term “AGI” and instead defines “powerful AI” concretely: a system smarter than a Nobel laureate across most fields, able to control tools, robots, and instruments, capable of running millions of copies at ten to a hundred times human speed. He calls it “a country of geniuses in a datacenter.”

His timeline rejects two extremes. There is no instant “Singularity” where everything transforms in days, because biology, manufacturing, clinical trials, regulation, and human institutions all move at their own stubborn pace. But there is also no reason progress should take a century. Amodei’s central concept is the “compressed 21st century”: after powerful AI arrives, we make the next 50 to 100 years of progress in just 5 to 10 years. Intelligence stops being the bottleneck, and the limiting factors become the speed of experiments and the friction of the real world. He organizes the upside into five areas:

1. Biology and health. The prevention and cure of most infectious diseases, the elimination of most cancer, reliable treatment of genetic disease, and a doubling of the human lifespan to roughly 150 years. That sounds like fantasy until you remember life expectancy already nearly doubled in the 20th century, from about 40 to 75, so doubling again is “on trend.” Drugs already extend maximum lifespan in rats by 25 to 50%, and some turtles live 200 years, so biology has no fixed ceiling.

2. Neuroscience and mind. Curing or preventing most mental illness, including depression, schizophrenia, addiction, and PTSD, then going further to improve baseline cognition, focus, and everyday emotional well-being.

3. Economic development and poverty. Harder than curing disease, he admits, because the bottleneck is not knowledge but distribution, politics, and the gap between rich and poor nations. The technology to lift the developing world will exist; deploying it is a human problem AI cannot solve alone.

4. Peace and governance. AI could tilt the global balance toward democracy over authoritarianism, but only through deliberate effort, never automatically.

5. Work and meaning. When machines do almost everything better than we do, what are people for? His answer is that meaning comes from the activity of living rather than from being economically indispensable, though he concedes the economy will have to be reorganized in ways we have not yet figured out.

What makes the essay land is its conditional structure. None of this is a prediction that things will go well; it is a portrait of what becomes possible if we get the risks right, offered as motivation to do exactly that. The title comes from a Richard Brautigan poem about a world where machines watch over us with “loving grace,” and Amodei is clear-eyed that grace is the optimistic branch, not the default one. For founders, the strategic signal is enormous. The essay is effectively a map of the largest markets of the coming decade, longevity, mental health, drug discovery, climate, and global development, and it reframes where value will concentrate: once intelligence is cheap and abundant, the scarce resources become the physical and regulatory chokepoints that intelligence cannot instantly dissolve. The companies that win will be the ones positioned at those chokepoints, translating a country of geniuses into things that actually ship into the real world. Read it not as prophecy but as a brief on the size of the prize. Dario Amodei (45 minutes)

The Adolescence of Technology

Fifteen months after painting the dream, Dario Amodei wrote the nightmare, and he says it was far harder to write. The Adolescence of Technology is the deliberate companion to Machines of Loving Grace, and it opens with a scene from Carl Sagan’s Contact: asked what single question she would put to an alien civilization, the astronaut answers, “How did you survive this technological adolescence without destroying yourself?” That, Amodei argues, is exactly where humanity stands. We are about to be handed almost unimaginable power, and it is deeply unclear whether our social, political, and technological systems are mature enough to wield it. He frames the whole moment as a rite of passage that will test who we are as a species.

The essay mirrors the optimistic one, mapping the dangers into five areas, each paired with a “Defenses” section so the reader is never left without a response:

1. Autonomy risk (”I’m sorry, Dave”). The same country of geniuses in a datacenter that could cure cancer could, if misaligned with human goals, divide its efforts across cyber operations, R&D, persuasion, and statecraft to disempower humanity entirely. The defenses are Anthropic’s core agenda, interpretability and alignment, making sure we can see what these systems are doing and that they want what we want before they grow too capable to correct.

2. Misuse for destruction (”A surprising and terrible empowerment”). AI dramatically lowering the barriers for individuals and small groups to build biological, chemical, nuclear, and cyber weapons, taking capabilities once limited to nation-states and putting them within reach of a motivated few.

3. Misuse for seizing power (”The odious apparatus”). AI as the perfect engine of authoritarian control through surveillance, propaganda, and entrenchment, with the same tools democracies need to defend themselves capable of being turned inward to build tyranny at home.

4. Economic disruption (”Player piano”). The section founders should read most carefully. Amodei restates his 2025 warning that AI could displace half of all entry-level white-collar jobs within one to five years, even as it accelerates growth. He separates labor market displacement from economic concentration of power, where the gains pool into a handful of companies or individuals who control the AI itself.

5. Indirect effects (”Black seas of infinity”). The harder-to-predict second-order consequences, building to the conclusion he calls “Humanity’s test.”

That conclusion is the most important part, because it explains why the essay is so sober rather than simply alarming. The deepest difficulty, Amodei argues, is that the risks are in genuine tension with one another, and you cannot just maximize safety on every axis at once. Taking the time to build AI carefully so it does not autonomously threaten us is in tension with the need for democracies to stay ahead of autocracies. The very tools required to fight authoritarian regimes can, taken too far, create tyranny in our own countries. Mitigating one danger can worsen another, and the only path through is to thread the needle on all of them simultaneously. There is no single lever to pull, which is why he resists both doomerism and easy optimism.

For founders, this essay is a strategic document as much as a moral one. It is the clearest available map of where regulation, scrutiny, and public anxiety will land over the next few years, and every “Defenses” section is effectively a list of industries that have to be built: AI security, model evaluation and interpretability, biosecurity, provenance and anti-fraud tooling, and the governance infrastructure for a world of abundant intelligence. Read alongside Machines of Loving Grace, the pair forms a single argument. The upside is staggering and the downside is existential, and the gap between them is closed not by technology alone but by the maturity, skill, and seriousness of the people building it. That is the test, and we are taking it now. Dario Amodei (60 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.

• SAFE: Guide / Video

• Convertible Note: Guide / Video

• Seed: Guide / Video

• Series A: 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.

Happy Friday.

Compute in Orbit

SpaceX’s biggest revenue line by 2030 won’t be rockets or satellites — it’ll be selling AI compute time from data centers in orbit, already under contract to Anthropic ($1.25B/month) and Google ($920M/month), from a business that didn’t exist before February. The energy bottleneck will kill the AI buildout before the chip shortage does — terrestrial solar requires permits that take years and land that’s politically radioactive, while orbital solar delivers 4–10x more power with no grid, no night cycle, and no NIMBYs; whoever controls cheap access to orbit controls the AI power supply. Run the “idiot index” on one critical cost line in your business this week: find the ratio between what you pay for something and the raw cost of its inputs, then ask who you’d have to fire or replace to close that gap — SpaceX cut launch costs 99% by refusing to accept supplier math. If you identify even one process where you’re paying a 10x markup because you accepted the first quote, you’ve found the wedge that could double a margin line — and the habit of questioning every requirement is what separates companies that hit escape velocity from those that optimize their way to irrelevance. A16Z (26 minutes)

Big Teams Make You Dumb

A programmer who stops being allowed to ship new ideas doesn’t just get frustrated — they stop having ideas at all, meaning every large org is running a slow lobotomy on its best people without anyone noticing it’s happening. The tree structure that every large company is forced to adopt means individual freedom shrinks in direct proportion to headcount — not because of bad managers or bad culture, but because the math of coordination requires it, so the only way to protect creative output is to stay small by design. Before your next hire, ask whether adding this person solves a problem or just compensates for a process you haven’t killed yet — Graham’s data is blunt: mediocre hires hurt you twice, once in output and once by making you bigger, which slows everyone else down. Founders who treat headcount as a last resort rather than a growth signal keep the small-team physics — fast decisions, full context, no tree — that are the only structural advantage a startup permanently holds over a well-funded incumbent. Paul Graham (8 minutes)

You’re Fixing The Wrong Leak

Nine out of ten founders who think they have a conversion problem actually have a demand problem — meaning every hour you spend tweaking your pitch, your pricing, or your close rate is covering for the fact that you’re simply not talking to enough people in the first place. Going from a 10% to 15% close rate is a 50% improvement that requires rebuilding your sales motion; going from 10 demos a month to 20 just requires more outbound — and right now AI can do the prospecting, scoring, sequencing, and intent-signal crawling that used to eat most of a sales team’s week, which means the bottleneck on demand is no longer labor, it’s whether you’ve pointed the system at the right ICP. Pull last month’s numbers and ask one question: did you miss because deals didn’t close, or because you didn’t have enough deals to begin with — if it’s the former, pick one intent signal (a job posting, a funding announcement, a blog post about an offsite) and rewrite your outbound sequence to open with that signal rather than a generic cold pitch this week. Founders who fix their demand diagnosis before hiring their first sales rep stop the most expensive mistake in early GTM — bringing in a salesperson to solve a product-market fit problem — and instead build a demand-rich pipeline where conversion improvements actually compound on something real. The Split (45 minutes)

Founder FAQ: Why Proper Documentation is Important for a Startup?

The moment a founder scrambles to find a signed employment agreement or a board consent during due diligence is the moment an investor starts discounting the valuation — your document chaos isn’t an admin problem, it’s a pricing problem. Investors and acquirers don’t just want clean docs — they’re using your document hygiene as a signal for how you run everything else; a disorganized data room says “this team cuts corners,” and that inference bleeds into every number on your cap table. Spend 90 minutes this week setting up a shared drive with ten folders — incorporation, board records, equity, executed agreements, templates, cap table, compliance, financials, IP, insurance — and drop every document you already have into the right place, even if some folders stay empty for now. When your next investor asks for a data room, you send a link in five minutes instead of spending three weeks in triage — and that composure alone signals the kind of operator people wire money to. 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.

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: Guide / Video

Saving Time and Money on Legal

When we met this Series B startup, they were frustrated with their law firm’s slow turnaround and high fees. Contract reviews took four to six weeks, and they charged $250,000 annually for basic work. The startup wanted to reduce sales cycle times and legal spend. They switched to General Counsel at Westaway. In year one, we 1) saved them about $200,000 in legal fees; 2) shortened their sales cycle by about four weeks; and 3) our streamlined processes saved their ops team eight to ten hours per month previously spent managing legal. By switching to Westaway, they expedited deal closures, saved hundreds of thousands in legal bills and regained one day per month in productivity. If you’re curious if we could save you time and money, let’s talk.

Post of the Week

Happy Friday.

Fish for Rejection Early

The Meta CRO who scaled one of history’s most important revenue orgs says the single most useful sales tactic he knows is deliberately forcing a “no” as early as possible — because a prospect who keeps saying “yes, we’re interested” while never committing is the most expensive customer you have, and most founders are too afraid of rejection to cut them loose. The best salespeople treat their time as the scarcest resource in the deal — not the product, not the relationship — and that reframe changes everything: you stop optimizing for enthusiasm and start qualifying for real intent, because a warm prospect who never closes costs you the same calendar time as one who does. Audit your current pipeline this week and find every deal that has had three or more “positive” conversations without a concrete next step — then send each one a short, kind message that names a specific deadline and offers two options: move forward by that date, or reconnect in 90 days when the timing is better. You’ll lose some deals that were never real, free up 20–30% of your sales team’s week, and create the scarcity signal that actually moves the prospects who are genuinely interested — because the ones worth closing almost always respond better to a deadline than to another follow-up. YouTube (48 minutes)

Shared Goals, No Silos

Figma’s CMO runs marketing, customer support, and growth under one roof — not because it’s tidy on an org chart, but because the moment you give marketing and sales different goals for different pipeline stages, you’ve already broken the system. The CMO role in 2026 is a portfolio manager, not a campaign owner: hold the whole engine accountable to the same end goal, run “maintain the business” work in the background, and pour disproportionate time into the two or three moonshots that could produce a step-change — because AI has made low-quality scale trivially cheap, and judgment is now the only scarce resource. This week, audit your team’s OKRs: if marketing owns MQLs and sales owns pipeline closed, collapse them into one shared revenue number, then separately track each team’s input metrics — that one change kills the finger-pointing loop and forces the conversation onto what actually matters. Teams that share the end goal stop optimizing their own stage at the expense of the next one, your best people spend less time on internal politics and more on the moonshots, and — as Figma’s playbook shows — you can expand your audience without losing the core community that made you credible in the first place. YouTube (60 minutes)

Co-Design or Get Lapped

Moore’s Law would have given you 10x compute over the last decade — NVIDIA delivered 1,000,000x — and the entire gap came from one design decision: stop optimizing individual layers and start co-designing chips, networking, storage, software, and compilers against the same objective at the same time. The same co-design principle that compounded NVIDIA’s hardware also predicts which AI products will compound and which will plateau: agents have a fundamentally different compute pattern than training (low-latency single-threaded CPU calls, not parallel throughput), and teams building agent products on infrastructure designed for training are optimizing the wrong layer — their ceiling is already baked in. This week, draw the actual compute pattern of your most important agent workload — trace every step from user input to output, mark where the system waits, and check whether your infrastructure was designed for that latency profile — because if your GPU is stalling on a CPU thread or a network storage hop, no amount of model optimization fixes it. Founders who match their architecture to the actual workload pattern in the next 12 months will build products that feel qualitatively faster than competitors running on mismatched stacks — and as tokens-per-watt keeps compounding and energy becomes the binding constraint, that structural efficiency advantage turns into a cost moat that is very hard to close from behind. The AI Corner (12 minutes)

Founder FAQ: What Are the Procedure of Taking Meeting Minutes?

Most founders treat board minutes as a box-ticking chore — but acquirers and investors read them during due diligence to assess whether your board actually governs the company or just rubber-stamps the CEO, and sloppy minutes have killed or repriced deals that the product and numbers would have otherwise won. Minutes are not a transcript — they are a curated legal record that shows the board exercised fiduciary judgment: what was decided, the key rationale behind it, and who voted; done right, they protect every board member from personal liability and signal to the next investor that your governance is clean before they ever ask. Before your next board meeting, draft a skeleton of the minutes directly from your board deck agenda — date, attendees, resolutions, quorum — so that during the meeting you are filling in decisions and rationale rather than trying to reconstruct them afterward from memory. Clean, consistently formatted minutes stored in a data room cut weeks off your next fundraise or acquisition process, give your lawyers less to fix, and mean that when a litigant or auditor comes looking, your paper trail shows a board that knew what it was doing — which is exactly the story you want told. 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.

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: Guide / Video

Extending Your Runway with General Counsel

In this economy, every startup is looking to lower burn rate and extend runway. We helped a Series A, generative AI company drastically reduce their legal spend by switching to our General Counsel service. When we first met the owners, they were working with a big law firm and felt they were overpaying for basic legal work. Nearly every month, they got a hefty bill just to cover equity grants, contract reviews and lawyer calls/emails. When they switched to General Counsel at Westaway, they:

• Got more personal service and quicker response times.

• Significantly reduced their legal spend.

With faster deal execution and lower spend, they extended runway and improved cash flow. If you’re looking to optimize legal costs and extend runway, click here to schedule a call. Let’s discuss whether on-demand General Counsel is right for your startup.

Post of the Week

Weekend Briefing

Field Notes: The Dolomites Circuit

Every evening on the trail followed the same improbable script. We stumbled off the mountain dirty, tired and proud, and within 30 minutes we were showered up and have an Aperol Spritz in hand and on your way to a three-course dinner and a warm bed. The next morning, we laced up and did it again…

Read more

2 months ago · 3 likes · Kyle Westaway

Happy Friday! Welcome to the month June.

Check out the the May 2026 venture capital funding data from AngelList.

Pre-Seed

Median Money Raised:

$1,153,125

Median Post-Money Valuation:

$11,250,000

Seed

Median Money Raised:

$4,310,625

Median Post-Money Valuation:

$30,250,000

Series A

Median Money Raised:

$21,200,000

Median Post-Money Valuation:

$132,500,000

Series B

Median Money Raised:

$45,527,778

Median Post-Money Valuation:

$248,333,333

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.

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: Guide / Video

Should a Seed Round Cost $100,000?

A friend recently told me his relatively straightforward $7 million seed round costs over $100,000 in legal fees — much higher than initially quoted. Unfortunately, this is becoming more common. However, for an experienced startup law firm, a standard seed round based on NVCA docs should cost $20,000 to $40,000 all in. At my firm Westaway, this complete seed round package is a flat $24,000. No runaway legal costs. No surprise bills. Just transparent pricing. If you’ve got an upcoming fundraise, let’s talk.

Happy Friday.

Go. Then Come Back

Stockholm has spawned Spotify, Klarna, and a credible bid to become Europe's startup capital, yet the harder truth is that no local ecosystem yet replicates what a few months in Silicon Valley do to a founder's ambition. The mechanism is not money or even network density, it is peer concentration: working alongside hundreds of equally ambitious founders compresses years of trial-and-error into a single cohort, and the only known dose-response is to actually go. The right prescription for non-Bay founders is small and reversible, go for a stint and come back, because returning founders are exactly what turns a promising local scene into a self-sustaining one. The bottleneck for most startup hubs is not capital or talent, it is exposure to people who treat building something planetary as the obvious goal rather than an exotic one.. YouTube (12 minutes)

Burn Tokens, Not Headcount

Most companies are still asking how AI can make employees more efficient, while the latest YC batch is building companies as a series of recursive AI loops that fire thousands of times an hour, around the clock, with no humans in the middle. The architecture is concrete: sensors pull from customer emails, support tickets, code changes, and product telemetry, a strategy layer codifies the rules of what AI can do alone versus what needs a human, and a tool layer of deterministic APIs handles the actual database queries and calendar checks. The real unlock is killing the Roman legion org chart where information flows up and commands flow down, and replacing it by turning the business knowledge trapped in Slack threads, emails, and human heads into context the AI can read and iterate against. The numbers tell the story: many recent Demo Day companies now post revenue per employee roughly 5x what was typical 18 months ago, and the founders who internalize “burn tokens, not headcount” will run companies that improve while they sleep. YouTube (13 minutes)

Recruit Like You Sell

The best salespeople you want to hire will never apply for your job — they’re already employed, being courted by their old boss, and have zero reason to open your LinkedIn posting, which means your entire inbound hiring funnel is systematically filtering out the people you actually need. The fix isn’t better job ads or a fancier recruiter — it’s treating talent acquisition as a sales motion: build an internal recruiting function compensated on commission, measure it with a pipeline funnel (touches → connections → screens → offers → hires), and do the same LinkedIn prospecting work you’d do to build a lead list. Take your two best salespeople, connect on LinkedIn, spend 30 minutes tonight going through their connections filtered by role and city, build a shortlist of 15 names, and come to a 20-minute meeting tomorrow where they tell you which ones are actually worth pursuing — that one structured conversation will outperform any referral bonus you’ve ever offered. Once this system is running, you stop competing for the candidates everyone else sees and start accessing the ones no one else is even talking to — which is the only talent market where you can consistently win. Common Cog (14 minutes)

Founder FAQ: What Are Procedures of Running an Effective Board Meeting?

Most founders treat board meetings as a performance — showcasing wins, glossing over problems — which means they’re spending their most expensive and experienced resource on an audience rather than a brain trust. Your board meeting is only as valuable as the specificity of the problem you bring to it. One or two pre-defined working sessions on your actual hardest problems will generate more value than 90 minutes of polished metrics review. Before your next meeting, decide the two questions you most need answered — not the ones that make you look strategic, but the ones that are genuinely keeping you up at night — then build the entire agenda backward from those, and send the deck seven days early so board members arrive already thinking rather than still reading. The outcome is a board that functions like an on-call advisory panel instead of a quarterly audit: they stay current through monthly written updates, they come prepared, and when you need a warm intro or a hard call on strategy, they’re already in the problem with you. Westaway (9 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.

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: 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:

1. Clear Pricing. Traditional billable hours can lead to misaligned objectives and unexpected fees. We’ve replaced this with straightforward, flat-rate pricing.

2. 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.

3. 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.

Post of the Week

Happy Friday.

I had a blast hanging out with the Founder Fridays communities at a happy hour in San Francisco this week. Thanks to everyone who came out.

Fight or Lose Them

Your best startup hires won’t quit over a bad salary — they’ll quit because you never pushed back hard enough on anything. Entrepreneurial people are builders, not extractors — they measure you by your willingness to fight for what’s right, and they read your silence or agreeableness as a character flaw, not a virtue. This week: pick one thing your team is doing wrong, say it plainly and publicly, then watch who argues back — the ones who push back hardest are likely your most valuable people, not your problem hires. You’ll retain the people who can carry you through a platform shift — the exact ones every well-funded competitor is actively trying to poach right now. Stay Sassy (7 minutes)

Your Absence Is the Metric

How long you can disappear without things breaking is a more honest measure of your leadership than how many people depend on you daily. Being the person everyone comes to isn’t leverage — it’s a ceiling; real scale happens when your team can solve novel problems by internalizing your principles, not by pinging you. Book a week fully offline in the next 60 days, tell no one to escalate to you, and debrief afterwards on every decision that stalled or went sideways — those gaps are your leadership debt, and fixing them is the actual work. You get a company that can move fast while you’re heads-down on the things only you can do — raising a round, closing a key hire, or figuring out your AI strategy — instead of one that freezes every time you step away. Boz.com (4 minutes)

Research Wins the Room

The thing that separates funded founders from the rest isn’t the deck or the numbers — it’s walking in knowing what this specific partner said on a podcast eight months ago about your exact category, and that’s now a two-minute prep task, not a two-hour one. VCs invest in 4 out of every 1,000 introductions they see, and the filter isn’t your market — it’s fit with how one specific human thinks; a six-prompt Claude pipeline that sequences fund thesis → partner background → objection map → portfolio signals → framing brief → one-page doc gives you that picture before you sit down. Before your next investor meeting, run just the first two prompts from this piece — fund profile and partner background — paste the outputs into a doc, and identify one thing the partner has said on record about your category that you can reference or directly address in the room. Founders who show investors they’ve done this level of prep trigger a different conversation — not evaluation mode, but engagement mode — and that shift is what moves a polite 45-minute meeting toward a follow-up ask. The Founder Corner (8 minutes)

Founder FAQ: What Are the Prime Tasks For the Board of a Startup?

The equity grants, exec hires, and major contracts you’ve already made without a paper trail are quietly sitting in your cap table like ticking clocks — and they’ll blow up the moment a serious investor runs due diligence. Board consents aren’t bureaucracy — they’re proof that your company made its biggest decisions legally and intentionally, and sophisticated investors use them to decide whether you’re fundable or a liability. This week, ask your lawyer to audit the last 12 months for any equity grants, key hires, major contracts, or financing decisions that lack a signed board consent — then get retroactive consents drafted before your next fundraiser kicks off. Due diligence moves faster, investors trust you more, and you don’t lose a round — or a valuation — because a lawyer found a governance gap three days before term sheet signing. 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.

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: Guide / Video

Is the Billable Hour Right for Startups?

Most law firms bill startups by the hour because that’s the status quo. But while it may work for big companies, the billable hour is likely the wrong model for startups. Why?

1. It incentivizes inefficiency. Firms are motivated to pad hours rather than work efficiently. This adds unnecessary costs.

2. It rewards busywork over results. Startups care about outcomes, not hours logged.

3. Costs are unpredictable. With fluctuating monthly hours, legal spend is hard to budget.

4. It stifles innovation. Hourly billing gives no incentive to find better solutions. Startups need forward-thinking counsel focused on results. That’s why we’ve ditched the billable hour for transparent flat fees.

If you’re ready to explore a law firm with a better billing model, let’s talk.

Post of the Week

Happy Friday.

I’ll be in the Bay Area next week click and would love to meet you. I’ll be hosting a happy hour on Wednesday night click here to sign up.

I’ll also be at the Praxis Summit. If you’re there shoot me a note. I’d love to say hi.

Q1 Startup Funding

Tech venture funding just rocketed from $5.3 billion to $36.2 billion in a single quarter, a nearly sevenfold spike that pushed total Q1 2026 capital to $39.9 billion across just 165 deals (the lowest deal count since 2016). Up rounds hit 86%, the first time they've cracked 80% since Q3 2022, and Series D and later pre-money valuations jumped from $1 billion to $2.5 billion in three months. The bifurcation is brutal though, Series B medians actually dropped from $195 million to $165 million, meaning capital is stampeding to anointed late-stage winners while mid-stage rounds get squeezed. If you're raising a Series B in 2026, you're competing against a market that's pricing your stage down 15% while writing checks 2.5x bigger one round above you, so sharpen your traction story or get creative with bridge structures before the gap widens. Cooley Go (5 min)

Agents Aren’t Copilots. They’re Replacements

Salesforce is now charging $2 per agent-completed call while Microsoft pushes Copilot at $30 per seat per month, and the gap between those two pricing models is the entire story of where enterprise AI value gets created. Per-seat productivity tools depend on rank-and-file employees actually changing how they work, but the original computing wave didn't make 1970s bookkeepers faster, it eliminated them, and executives bought in because the ROI was a brutally rational calculation on the bottom line, not a change-management gamble. That's why the most interesting AI bet right now is Palantir's ontology-driven Foundry approach, where years-long, top-down data integration engagements look like "back to the future" to SaaS investors who got addicted to organic, credit-card-driven adoption. If you're building in AI, stop pitching seat licenses to team leads and start pitching "seat-replacement" contracts to the C-suite, because the buyers willing to fund agent infrastructure care about replacing the 41% of wasted labor, not augmenting the workers doing it. Stratechery (8 minutes)

Infinite Supply Changes Everything

Every marketplace breakthrough in history — Uber, DoorDash, Indeed — came from unlocking a new form of supply. AI doesn’t just unlock more supply. In some categories, it creates supply that never sleeps, never has calendar constraints, and trends toward zero marginal cost. If your marketplace moat depends on supply scarcity, that moat is already eroding. The race to the bottom is real, but it only hits founders who mistake the AI tool for the business. The actual opportunity is positional: own the workflow before and after the transaction, not the transaction itself. Marketplaces that survive this shift will capture the awareness and consideration stages of the buying cycle — not just intent and purchase — turning search boxes into intelligent, personalized guides. The ones who don’t will watch take rates compress until the math stops working. This week, map your full demand-side workflow: what does your buyer do in the 30 days before they come to your marketplace, and the 30 days after? Pick one step in that pre- or post-transaction journey that currently happens off your platform and build or bolt on something that pulls it in. Even a lightweight AI tool that helps buyers scope, plan, or evaluate — before they transact — creates the high-frequency retention loop that makes downstream monetization inevitable. The goal is: demand comes for the AI, stays for the marketplace. Incumbents have the data and capital advantages, but they’re optimizing the existing transaction. The attack surface is the workflow around it. Founders who embed themselves in pre- and post-transaction behavior before incumbents notice will build switching costs that have nothing to do with supply depth or take rates — and everything to do with the fact that leaving means losing your whole workflow, not just your vendor list. NFX (7 minutes)

Founder FAQ: How Startups Board Members Can Be More Efficient?

Most founders treat their board like a quarterly obligation — prep the deck, survive the meeting, repeat. The counterintuitive reality: board performance is almost entirely a function of what the founder puts in, not who’s in the room. A weak board is usually a founder problem, not a director problem. The board meeting is the last place where real decisions should be made. By the time everyone is in the room, the outcome should already be known. Every major decision needs to be pre-sold one-on-one before it hits the table — not because you’re gaming the process, but because surprises in group settings create defensive reactions, not good thinking. The meeting is for ratifying, not debating. Before your next board meeting, call each member individually. Not to brief them — to ask what they’re seeing, what concerns them, what they’d push back on. Then send your pre-read 72 hours out, not 72 minutes. If you catch yourself thinking “I’ll just explain it in the meeting,” that’s the thing that’s going to derail the meeting. Resolve it on the call first. Founders who run their boards this way get something most don’t: board members who actually work between meetings. When a member feels genuinely consulted rather than periodically updated, they make introductions, flag risks early, and advocate internally at their own funds. The ones who feel like passive audience members do the minimum. The difference is entirely in how the founder runs the relationship — not in who they picked. 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.

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: 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.

Post of the Week

Happy Friday.

Software Ate The World, Now AI Eats The Software

Every industry you thought was protected — SaaS, services, agriculture, defense, drug discovery, semiconductors — is being rebuilt from scratch, and the founders who move in the next 12 months will set the category defaults for the next 20 years. AI has simultaneously collapsed the cost of producing software, running services, and executing scientific discovery — which means the moat that protected every incumbent (code volume, headcount, institutional knowledge) is gone, and the new moat is closed loops: companies that make their operations, data, and workflows fully legible to AI will compound every model improvement automatically while everyone else catches up manually. Pick the single most expensive, manual, or outsourced process in your market — whether that’s pesticide application, chip supply chain tracking, scientific hypothesis generation, or enterprise compliance — and ask: can I replace the outcome entirely rather than improve the tool? Then identify the one incumbent whose moat was pure code volume, and start building the AI-native replacement this week. The founders who frame their companies as closed-loop outcome providers — not software vendors, not copilots — will raise faster, price higher, and build the category-defining companies of the next decade while everyone else is still debating feature roadmaps. Y Combinator (15 minutes)

Your Org Chart Is The Bug

Adding AI copilots to your existing workflows isn’t a strategy — it’s a way to preserve the exact org structure that AI is about to make obsolete. Every layer of human information routing — managers, status rollups, coordination meetings — exists because companies ran as open loops where data was fragmented and manually interpreted; AI closes that loop, which means the middleware isn’t just redundant, it actively slows you down. This week, pick one process that requires a human to gather and summarize information for someone else — a sprint review, a status update, a weekly report — and replace it with an agent that has direct access to the source data: Linear, Slack, GitHub, sales calls; then measure whether the output is better or worse than the human version. Early-stage founders who build queryable, artifact-rich companies from day one start with an architectural advantage that incumbents literally cannot replicate without breaking their live product — and that gap compounds with every model improvement. YouTube (10 minutes)

Complexity Is a Product Flaw

A Canadian startup selling tractors with 1990s engines and zero software just received 400 unsolicited inquiries from American farmers after a single interview — because John Deere spent 20 years building machines farmers can’t fix themselves. When an incumbent adds complexity to extract margin and lock in customers, it creates a permission structure for a challenger to win on simplicity alone — Ursa Ag isn’t competing on features, it’s competing on who owns the machine after the sale. Audit your competitor’s product this week specifically for features that exist to create dependency rather than deliver value — proprietary formats, locked integrations, required service contracts — then make “you own it completely” a first-class part of your pitch. In any market where the incumbent has spent years prioritizing lock-in over repairability or portability, a stripped-down challenger priced at half the cost doesn’t need a marketing budget — the resentment is already there, waiting for an alternative to show up. Wheelfront (4 minutes)

Founder FAQ: How To Build a Competent Board for a Startup?

Most founders treat board seats as a fundraising concession — something you give away to close a round — when they’re actually the most consequential governance decision you’ll make, because the wrong person at the table can block your exit, fire you, or derail a Series B years after the check clears. A board seat is a decade-long relationship with legal authority over your company, not an advisory role — which means the right selection criteria aren’t credentials or brand-name fund, they’re trust, intellectual honesty, and whether this person will tell you hard truths when you’re wrong. If you’re 6–9 months out from a raise, identify two or three people you’d consider for a board seat and call three founders they’ve previously worked with this week — not for a reference check on their resume, but to ask specifically: “Did they push back when it mattered, and did it help?” Founders who treat board composition as a strategic asset rather than a deal term end up with a room that accelerates decisions, opens doors, and protects them when things get hard — instead of one that slows them down when speed is the only thing that matters. 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.

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: Guide / Video

Control Legal Spend

Startups suffer from unpredictable legal bills under the billable hour system. Fees fluctuate month to month without warning. Law firms drag out billable hours, but startups foot the bill. Even basic work can lead to surprisingly high legal bills. This unpredictability cripples financial planning. Budgets rarely match actual spend. With utter uncertainty around legal spend, startups cannot forecast or manage burn rates effectively. The antiquated billable hour system fails them. Our General Counsel flat, monthly fee service gives startups cost certainty. Legal spend becomes predictable with bundled services and no surprise overage bills. By switching from hourly to our flat-fee model, startups finally get confident budgeting, accurate forecasting and predictable legal spend. If you’re sick of getting surprise legal bills and are interested in controlling your legal spend, let’s talk.

Post of the Week

Happy Friday! Welcome to the month May.

Check out the the April 2026 venture capital funding data from AngelList.

Pre-Seed

Median Money Raised:

$1,317,600

Median Post-Money Valuation:

$12,200,000

Seed

Median Money Raised:

$4,194,200

Median Post-Money Valuation:

$31,300,000

Series A

Median Money Raised:

$13,490,400

Median Post-Money Valuation:

$92,400,000

Series B

Median Money Raised:

$45,527,778

Median Post-Money Valuation:

$248,333,333

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.

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: Guide / Video

Should a Seed Round Cost $100,000?

A friend recently told me his relatively straightforward $7 million seed round costs over $100,000 in legal fees — much higher than initially quoted. Unfortunately, this is becoming more common. However, for an experienced startup law firm, a standard seed round based on NVCA docs should cost $20,000 to $40,000 all in. At my firm Westaway, this complete seed round package is a flat $24,000. No runaway legal costs. No surprise bills. Just transparent pricing. If you’ve got an upcoming fundraise, let’s talk.

Ferrari’s Scarcity Flywheel

Ferrari has sold just 330,000 cars in 79 years, fewer than Rolex ships in 3 months, yet it clears $8.2B in revenue at a nearly 50% gross margin and throws off $170K+ of gross profit per car while Ford runs ~7%, BMW ~14%, and Porsche 15-25%. The scarcity math: ~14,000 units a year, 80% reserved for existing owners so fewer than 3,000 slots go to new customers annually, and the top Icona tier (the F80 supercar: 799 units at $4M each) carries 80-90% gross margins and can contribute ~30% of annual profits in its first delivery year. The brand moat is a graduation ladder (you must own 10-20 Ferraris before you’re even invited to buy a supercar), an inclusivity-exclusivity paradox (400M F1 fans, a theme park, and Puma collabs for fandom; the 0.0001% actually own the product), and a functional alibi where 80 years of unbroken F1 history lets buyers frame a $500K average price as performance engineering rather than status signaling. The founder takeaway is to design scarcity as a feature rather than a limitation: sell one less than the market demands, turn manufacturing inefficiency into a marketing asset, refuse any scale that dilutes the myth, and build one moat (like an unbroken 80-year racing record) that capital literally cannot buy. Acquired Briefing (7 min)

Ferrari is a fascinating company. If you like deep dives on business strategies like this, check out my other email Acquired Briefing.

Acquired Briefing

Demand Beats Supply, Always

Microsoft deliberately sandbagged its own Azure growth number — they had the GPU capacity to beat it, but chose not to, because their internal workloads were worth more than the customer revenue they gave up. The real constraint in AI right now isn’t cost-per-query — it’s opportunity cost: every enterprise deal you take means turning away a higher-margin internal workload, and every consumer user you serve is compute you can’t sell to an agent workflow paying 10x more, which means every AI company is quietly rationing who gets served and at what quality. This week, rank your customer segments by gross margin per unit of compute (or attention, or engineering time) — if your lowest-margin cohort is consuming a disproportionate share, you don’t have a pricing problem, you have an allocation problem, and you should either reprice that tier or cut it. Founders who figure out their own opportunity cost hierarchy before their next fundraise will have a far more defensible unit economics story — and will stop accidentally subsidizing the customers who are quietly killing their margins. Stratechery (12 minutes)

Users Win, Founders Don’t

U.S. consumers are extracting $172 billion in annual value from generative AI — but they’re mostly doing it for free, which means the gap between value created and value captured by founders has never been wider or more dangerous to ignore. Adoption speed without monetization is a liability: AI reached 53% population adoption faster than the internet ever did, coding benchmarks went from 60% to near 100% in a single year, and yet the talent pipeline feeding U.S. AI is down 80% in one year — which means the window to build a defensible position on the current capability curve is much shorter than the hype suggests. This week, calculate what your product would need to charge to capture even 5% of the value a median user gets from it — if that number feels politically impossible, you either have a pricing problem or you’re building a feature, not a business, and you need to know which one before your next board meeting. Founders who close the value-capture gap now — before commoditization accelerates and open-source closes the remaining performance delta — will be the ones still standing when the market stops rewarding growth and starts demanding margin. HAI Stanford (15 minutes)

Founder FAQ: Why Balancing duties and interests are important for a Founder in a Startup?

The business judgment rule protects you from a bad outcome — but it does not protect you from a bad process, meaning a founder who accepts an acquisition offer that turns out great can still be sued for how they made the decision. As a founder, you are legally bound to two duties at all times — care (make decisions like a diligent, informed person would) and loyalty (never let your personal upside override the company’s interests) — and in a fundraising environment where investors are scrutinizing governance harder than ever, a single undisclosed conflict of interest can unravel a deal or a board relationship faster than any cap table issue. This week, write down every financial relationship you have that touches your company — vendors you own equity in, side projects competing for your time, any transaction where you’re on both sides — and run it by your attorney or a disinterested board member before your next board meeting, not after. Founders who document their decision-making process and disclose conflicts proactively build the kind of investor trust that survives hard moments — and avoid the personal liability that quietly follows founders who didn’t think the legal stuff applied to them. 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.

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: 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.

Post of the Week

My sincere apologies! I found last week’s Founder Fridays in my drafts folder. So, I’m sending it tonight. You’ll see another one tomorrow morning as usual.

Here’s my April playlist.

The Brand Age

Between the early 1970s and early 1980s, unit sales of Swiss watches fell by almost two-thirds, yet the handful of watchmakers who survived ended up more profitable than ever, not by making better watches but by transforming themselves into luxury brands selling expensive status symbols. That pivot reveals the most important thing technology does to any industry: it eventually makes substantive product differences disappear, which means brand, what's left when everyone can match your performance, becomes the only game in town. The critical tension every founder must understand is that branding and design are fundamentally opposed, since design seeks the single right answer (which converges with competitors), while branding requires distinction (which demands moving away from right answers and toward the deliberately unreasonable). The deeper lesson for founders is not to copy the brand playbook but to follow genuinely interesting problems, build during the golden age of your field, and recognize the inflection point before technology commoditizes the thing you've spent years perfecting. Paul Graham (25 min)

Seed Checks, Fewer Bets

Q1 2026 was the largest venture quarter ever recorded, with $300 billion poured into roughly 6,000 startups globally, up 150% both quarter-over-quarter and year-over-year. The obvious reaction is that it’s all four mega-deals (OpenAI, Anthropic, xAI, and Waymo combined for $188B), but even stripping those out you’re looking at a ~$112 billion quarter, which would itself be a record in most prior years. About 80% of the capital went to AI companies, up from 55% a year ago, with early-stage funding up 41% and seed dollars up 31% year-over-year. The seed data carries one important tension founders should track: while total dollar investment was up, deal count fell 30% from Q1 last year, meaning VCs are writing fewer bets with significantly larger checks, a signal that the flight to quality at the early stage is accelerating fast. A16Z (3 min)

Discount The POC, Not The Price

The enterprise buyers actually spending the most on AI deliberately run multiple tools for the same job — meaning the competitor you’re discounting against may already be in the budget alongside you, and you’re giving away margin you never had to give. AI price wars are fought on the wrong battlefield: the real threat isn’t the cheaper competitor but your customer’s engineering team, and as inference costs keep falling, the only defense that works is differentiation that’s genuinely expensive to rebuild internally — deep workflow integration, proprietary training data, embedded customer success. Take your next competitive deal where you’re tempted to cut price and instead cut the POC — offer free credits, unlimited usage during evaluation, or a zero-friction 30-day trial, then hold your contract price firm once they’re hooked. Buyers consistently chose the tool that proved indispensable during evaluation, not the cheapest one — founders who protect their price and win on adoption will enter the market consolidation phase with better unit economics and customers who stay because switching is genuinely costly. A16Z (8 min)

Founder FAQ: Why Drafting Strong Contracts Is Important For Startups?

Most founders treat contracts like checkbox tasks, which is exactly why the majority of startup legal disputes trace back to the same three drafting mistakes. The foundation isn't the contract itself but a term sheet that locks in price, payment terms, IP ownership, and dispute resolution before formal drafting begins, because walking back agreed-upon deal points mid-draft is both expensive and relationship-damaging. Strong contracts require precision over jargon: specific obligations with hard deadlines, active voice that names who does what, and key terms defined clearly and used consistently throughout, since ambiguity is not just a nuisance but the soil where disputes grow. Your startup lawyer's real value is not writing legally compliant language but knowing which deal points are actually worth fighting for in your specific situation, and moving fast enough that legal process doesn't kill deal momentum. 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.

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: Guide / Video

Saving Time and Money on Legal

When we met this Series B startup, they were frustrated with their law firm’s slow turnaround and high fees. Contract reviews took four to six weeks, and they charged $250,000 annually for basic work. The startup wanted to reduce sales cycle times and legal spend. They switched to General Counsel at Westaway. In year one, we 1) saved them about $200,000 in legal fees; 2) shortened their sales cycle by about four weeks; and 3) our streamlined processes saved their ops team eight to ten hours per month previously spent managing legal. By switching to Westaway, they expedited deal closures, saved hundreds of thousands in legal bills and regained one day per month in productivity. If you’re curious if we could save you time and money, let’s talk.

Post of the Week

Happy Friday.

Agents Do Jobs

Most founders building AI agents are automating the wrong things first — they’re reaching for complex, one-off workflows when the highest-ROI agent is almost always the single most boring, repetitive task someone on their team does every single day. The gap between a chatbot and an agent is the gap between a tool and an employee: agents don’t just respond, they perceive, reason, act, and loop until a goal is done — and that “while not done” loop, hooked into your actual systems, is where the 171% ROI enterprises are reporting actually comes from. This week, ask every person on your team to name the one task they do daily that feels like it could be taught to a new hire in 20 minutes — that list is your agent backlog, ranked by frequency and embarrassment, and you should have a no-code prototype of the top item running before Friday. One reliable agent on a high-frequency workflow compounds fast: it frees a person’s time, creates a logged, auditable process, and gives you a proof-of-concept you can show investors or customers as evidence you’re building an ops advantage that’s hard to copy. The AI Corner (6 minutes)

The Hunt for Bitcoin’s Creator

The New York Times just published its most comprehensive investigation into the identity of Satoshi Nakamoto, and the evidence points to Adam Back, the 55-year-old CEO of Blockstream and creator of Hashcash, the proof-of-work system that became foundational to Bitcoin mining. John Carreyrou, the journalist who broke the Theranos story, spent a year analyzing overlapping timelines, matching writing patterns and connecting Back’s cryptographic work to Bitcoin’s architecture. Back flatly denied it, calling the evidence “circumstantial interpretation” rather than definitive cryptographic proof. For founders in crypto and Web3, the deeper lesson is that Bitcoin’s value has only grown precisely because it operates independently of any single creator, proving that the strongest protocols are the ones that transcend their founders. NYT (22 minutes)

Enterprise AI Is Real Now

That widely-cited MIT stat claiming 95% of enterprise AI pilots fail is almost certainly wrong — hard internal data from a16z shows 29% of the Fortune 500 are already live, paying AI customers, less than 3.5 years after ChatGPT launched, which is faster enterprise penetration than any previous technology wave. The pattern behind every breakout enterprise AI use case — coding, support, legal, healthcare — is the same: the work is text-based, the output is verifiable, there’s a human in the loop as a natural safety valve, and you don’t need 100% accuracy to deliver clear ROI; the sectors still waiting for their moment share the opposite traits: physical world, interpersonal relationships, regulatory friction, unverifiable outcomes. If you’re building or pitching in a sector that hasn’t broken out yet, run this checklist against your use case this week: Is the output verifiable? Is there a clean human escalation path? Is the work text-based? Does your buyer already measure success in quantifiable metrics? If you hit all four, you have a credible “why now” for investors — if you’re missing two or more, figure out which constraint you’re actually solving before your next pitch. Accounting and auditing jumped nearly 20 points on model capability benchmarks in the last four months — founders who are already building in the next wave of sectors, with real customer infrastructure in place before the capability unlocks arrive, will be the ones who capture the market when it tips. A16Z (9 minutes)

Founder FAQ: What Are the 10 Contracts Every Startup Should Have on Hand?

Most founders scramble to draft agreements in the middle of a deal, which is exactly the wrong time to be negotiating legal terms under pressure. The 10 contracts every startup should have ready to go are: an advisor agreement, an independent contractor agreement, an employment offer letter, a CIIAA (confidential information and invention assignment agreement), a restricted stock purchase agreement, a stock option grant, an NDA, a master service agreement, a board consent template, and a separation agreement. Each one protects a different flank, from securing your IP and aligning incentives with equity grants to streamlining client deals with an MSA that eliminates renegotiation on every project. Having these agreements custom-drafted before you need them isn’t just good legal hygiene, it’s a competitive advantage that lets you close deals, onboard talent and protect your company without losing a single day of momentum. 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.

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: Guide / Video

Extending Your Runway with General Counsel

In this economy, every startup is looking to lower burn rate and extend runway. We helped a Series A, generative AI company drastically reduce their legal spend by switching to our General Counsel service. When we first met the owners, they were working with a big law firm and felt they were overpaying for basic legal work. Nearly every month, they got a hefty bill just to cover equity grants, contract reviews and lawyer calls/emails. When they switched to General Counsel at Westaway, they:

• Got more personal service and quicker response times.

• Significantly reduced their legal spend.

With faster deal execution and lower spend, they extended runway and improved cash flow. If you’re looking to optimize legal costs and extend runway, click here to schedule a call. Let’s discuss whether on-demand General Counsel is right for your startup.

Post of the Week

Happy Friday! Welcome to the month April.

Check out the the March 2026 venture capital funding data from AngelList.

Pre-Seed

Median Money Raised:

$1,155,000

Median Post-Money Valuation:

$11,000,000

Seed

Median Money Raised:

$3,290,000

Median Post-Money Valuation:

$28,000,000

Series A

Median Money Raised:

$23,156,250

Median Post-Money Valuation:

$142,500,000

Series B

Median Money Raised:

$45,527,778

Median Post-Money Valuation:

$248,333,333

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.

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: Guide / Video

Should a Seed Round Cost $100,000?

A friend recently told me his relatively straightforward $7 million seed round costs over $100,000 in legal fees — much higher than initially quoted. Unfortunately, this is becoming more common. However, for an experienced startup law firm, a standard seed round based on NVCA docs should cost $20,000 to $40,000 all in. At my firm Westaway, this complete seed round package is a flat $24,000. No runaway legal costs. No surprise bills. Just transparent pricing. If you’ve got an upcoming fundraise, let’s talk.