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

22 days 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.

Happy Friday.

Two Paths, No Middle

Most software CEOs think they’re buying time with incremental layoffs and “AI-enhanced” roadmaps — they’re not; the market has already priced in the middle ground as a dead end. The terminal value of software is being repriced right now, and the only two positions that survive are +10 points of revenue growth from genuinely new AI-native products, or 40%+ true operating margins (stock comp included, no asterisks) — everything between those poles is a slow bleed of multiple compression and dilution. This week, put one question at the top of your board deck and don’t let yourself off the hook with a vague answer: are we credibly on the growth path or the margin path — and if growth, who are the five people (regardless of title) you’d bet the company on, and have you actually given them the mandate yet? Founders who pick a lane and execute hard over the next 12-18 months come out the other side with either a reaccelerated business and a team that believes in the mission again, or a lean, high-margin asset that throws off real cash — both are fundable, acquirable, and defensible; the middle is none of those things. A16Z (8 minutes)

Distribution Is The Moat

When anyone with a laptop can ship a working product overnight, the thing you spent months building can be replicated by a solo founder this weekend — which means your tech is not your defensibility, your audience is. Distribution isn’t followers or views — it’s the consistency of getting the right message in front of the right people repeatedly, and in a world where the cost to build approaches zero, the ability to own attention and convert it into a specific buyer is the only asset that compounds and can’t be instantly cloned. This week, map your current distribution honestly across three columns — UGC, paid, and organic — identify which one you’ve been neglecting entirely, and commit to one repeatable action in that channel before the end of the week, even if it’s just one piece of content or one seeded conversation with a creator in your space. Founders who build a consistent distribution engine now — before they need it — will be the ones who survive the next wave of AI-built competitors, because when the product is table stakes, the relationship with the audience is the only thing a new entrant can’t spin up overnight. X (5 minutes)

Survive First, Win Later

The founders who reach out for help when they’re three months from death aren’t the reckless ones — they’re often the brightest ones who never made “don’t die” their first principle, treating survival as a given instead of an obsession. Winning long-term isn’t about the boldest moves or the best ideas — it’s about staying alive long enough to be right, because almost every failure mode except running out of runway or quitting is recoverable, and the founders who compound quietly over years are exponentially harder to stop than the ones who spike and flame out. This week, calculate your actual death boundary — not your optimistic runway, but the specific number, date, and conditions under which you genuinely cannot recover — then ask whether every major decision you’re making right now has been stress-tested against that boundary first. Founders who internalize survival as a non-negotiable constraint paradoxically become more aggressive, not less, because once you know exactly where the cliff is you can sprint right up to the edge — and that clarity about the downside is what lets you take the asymmetric risks that build the real moats. Amjad Masad (6 minutes)

Founder FAQ: What Should I Do in the First 30 Days of My Startup?

The founders most likely to lose their company in a legal or financial crisis aren’t the ones who took big swings — they’re the ones who were too busy building to spend three days on paperwork in month one, and that oversight compounds silently until it explodes at the worst possible moment.Your cap table, corporate records, EIN, and bank account aren’t bureaucratic busywork — they are the infrastructure that determines whether you can close a funding round, hire cleanly, or survive due diligence without a fire drill, and every week you delay them is a week of technical legal debt accumulating on top of your technical product debt.This week, if you haven’t already, open your post-incorporation checklist and block a single afternoon to knock out the three most critical items: get your EIN, open a business bank account, and set up your cap table — none of these take more than a few hours and all three become exponentially harder to fix retroactively.Founders who treat legal and financial hygiene as a product sprint — done once, done right, maintained consistently — never lose a deal, a hire, or a round to something that cost $500 and a Tuesday afternoon to prevent. 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

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.

Taste Is Competitive Moat

While most AI companies are racing to ship faster and cheaper, Weber Wong spent 10 weeks waiting for a handcrafted Italian couch for his startup’s Brooklyn office, and it wasn’t vanity. Wong is the founder of Flora, a $42 million AI-native creative tools company, and he argues that existing AI models are “made by non-creatives for other non-creatives to feel creative.” His contrarian bet is that the real moat in AI isn’t model performance, it’s taste. Flora doesn’t compete on model quality. Instead, it offers an “infinite canvas” that integrates with existing models through a visual interface where professionals in fashion, advertising, and film can generate text, images, and video in node-based workflows. Wong’s deeper insight is that most creative professionals are stuck in “artifact thinking,” generating one output at a time with no system underneath. The founders who build creative infrastructure, not just creative tools, will own the next wave of professional AI adoption. Every (4 minutes)

The Delegation Sales Question

Asking enterprise buyers “what’s your biggest pain point?” is dead — sophisticated buyers have already patched their obvious problems, and the question that unlocked a $1B company was simply: “If you could hire someone to sit next to you, what would you hand off?” Reframing discovery around delegation instead of pain removes the ego threat — buyers stop defending their competence and start revealing what they actually resent doing, which is where your real wedge lives. Before your next five customer calls, swap your pain-point opener for a delegation question and listen specifically for tasks they’ve “solved” with workarounds they hate — that gap between “it works” and “I love it” is your product. Founders who find that gap and build a 10x better experience inside a budget category buyers already have will compress their sales cycle dramatically, because the ROI is obvious before procurement even gets involved. First Round (9 minutes)

More Channels, Less Signal

Adding a Slack channel to fix communication is the same mistake as adding highway lanes to fix traffic — both just induce more volume, and your team ends up knowing less despite being bombarded with more. The bottleneck was never output, it was absorption — and every channel you add raises the noise floor, making it harder for anything critical to land. This week, count every communication channel your company uses, then kill one — pick the channel with the lowest signal-to-noise ratio and shut it down before Friday; the test is whether anyone notices. Teams that consolidate ruthlessly will find that fewer, clearer channels actually move faster — because people stop tuning out and start hearing what matters. The Best Leadership Newsletter (5 minutes)

Founder FAQ: How Do I Pick a Startup Co-founder?

Most founders treat co-founder selection like a dating app, chasing credentials and résumé overlap instead of the qualities that actually predict survival. Research from Noam Wasserman's The Founder's Dilemma shows that 65% of startup failures trace back to interpersonal tension within the founding team, making this the single highest-stakes decision you'll face before writing a line of code. The framework is straightforward: you need complementary skills (every team needs a builder and a seller), shared passion for the specific problem you're solving, and aligned values that will guide hard decisions when things get messy. The trap is that it's nearly impossible to assess these qualities in someone you don't already know well, which is why the best co-founder relationships almost always come from deep prior experience working together. Don't optimize for the most impressive name. Optimize for the person you'd trust in a foxhole. 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.

Vision Is The Moat

AI isn’t competing for the $1 trillion global software market — it’s competing for the $50–60 trillion global labor market, which means every founder still pitching “we replace a tool” is playing the wrong game entirely. When intelligence becomes infrastructure, the constraint flips: capital, talent, and technology are all commoditizing fast, which means the only defensible edge left is a founder’s conviction about what the world should look like before anyone else can see it. Rewrite your one-liner by replacing the word “tool” or “platform” with what work your product actually does autonomously — if you can’t describe it as labor replaced rather than software sold, your positioning is already behind where the market is heading. Founders who reframe their product as autonomous labor rather than a SaaS tool will find sharper product focus, faster investor pattern-matching, and a larger addressable market on the pitch deck — because they’re pricing against human work, not against a competitor’s subscription. NFX (9 minutes)

NRR

Most founders know their bank balance to the dollar but can’t tell you their net revenue retention — yet NRR is the single number that tells you whether your business is actually working or just surviving on new bookings. Revenue is the only metric customers can’t fake: they either pay again or they don’t, and tracking just five MRR flows (new, expansion, contraction, churn, net) gives you a complete picture of business health that gut feel and NPS never will — especially now, when investors at every stage are pattern-matching on retention quality before they write a check. Pull three months of billing data and calculate your Gross Revenue Retention (GRR) and Net Revenue Retention (NRR) — if NRR is above 100%, expansion is covering churn and you have a story; if it’s below, you have a leak to fix before your next fundraise conversation. Founders who can answer “what’s your NRR and payback period?” in under 60 seconds close investor conversations faster and make better hiring and spend decisions — because they’re operating on signal, not noise. The VC Corner (8 minutes)

Data Network Effects

Software ETFs are down 30% since January on fears that AI kills the industry — but the bear case is built on a fundamental misreading of where software value actually lives, and founders who understand the difference are about to inherit markets from incumbents who don’t. Code was never the moat — data network effects, embedded workflows, and brand trust are what made software companies durable, and AI makes all three stronger, not weaker, because better models don’t shrink the application layer, they make it more capable of doing things with the knowledge it already holds. Map your product against one specific moat — data network effects, proprietary data, or process depth — and write a single paragraph explaining why that advantage compounds as AI improves; if you can’t write that paragraph, you’re building a thin wrapper that will get repriced, and you need to find your way to a deeper layer before your next raise. Founders who can clearly articulate a non-code moat will close rounds faster in a market where investors are actively separating “real software businesses” from “ChatGPT with a UI” — and they’ll be building toward the larger, not smaller, software market that comes out the other side of this transition. A16Z News (11 minutes)

Founder FAQ: Which common open sources are suitable for Startups?

With thousands of open source licenses in existence, 98% of all open source code in use is covered by just 20 — meaning the license decision most founders agonize over is actually a binary choice between two philosophies: share freely or control derivatives. Permissive licenses (MIT, Apache, BSD) maximize adoption and collaboration; copyleft licenses (GPL, MPL) force anyone who builds on your code to release their changes — and which camp you choose signals whether your moat is community or code control. Audit every open source dependency in your product and check whether any are GPL-licensed, because if they are and you’re distributing software, you may already have an obligation to open-source your own code — a legal exposure most early-stage teams don’t discover until due diligence. Founders who nail this early avoid the messy, expensive relicensing conversations that derail Series A diligence and give enterprise buyers a clean answer when legal teams ask about your IP chain. Westaway (7 minutes)

Startup Funding Guides

I’ve put together a series of guides to equip founders to excel at fundraising. These guides break down the deal term-by-term and give you negotiation tips so that you can speak to investors with confidence.

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! Welcome to the month March. To kick off the moth, check out my March playlist.

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

Pre-Seed

Median Money Raised:

$975,000

Median Post-Money Valuation:

$9,750,000

Seed

Median Money Raised:

$4,375,000

Median Post-Money Valuation:

$31,250,000

Series A

Median Money Raised:

$15,398,125

Median Post-Money Valuation:

$86,750,000

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.

AI Kills Your Interface

The $25K/seat vertical SaaS you built on workflow UX is now worth zero—because when users type plain English into a chat box, years of carefully designed UI muscle memory becomes instantly obsolete. Your competitive moat wasn’t the data (it was licensed or public); it was the interface layer, and AI just made that layer disappear by replacing it with natural language that runs entirely in the cloud. This week, audit which parts of your product are actually “interface tax” versus genuine workflow value—ask your team: “If a user could describe what they want in one sentence to an AI agent, would they still need this feature?” The companies that survive won’t be the ones defending their UI; they’ll be the ones rebuilding around agent-first architectures before their customers realize they’re paying premium prices for what’s become a thin client with an expensive legacy wrapper. Stratechery (8 minutes)

ChatGPT Ads

Ad agencies are flooding into ChatGPT advertising without measurement tools or brand safety guarantees because they’ve watched consumer discovery migrate to AI platforms and know missing this window means losing the next decade of digital distribution. The underlying shift is that search behavior is moving from Google’s ten blue links to conversational AI—and the first movers who figure out how to show up in those AI-generated answers will own customer acquisition before pricing goes through the roof. This week, allocate 5-10% of your paid budget to test ChatGPT ads (or similar AI platform ads) and track one metric obsessively: conversion rate compared to your Google Search campaigns, because you need to learn what messaging works in conversational contexts before your competitors do. If ChatGPT converts even 70% as well as Google at half the CPC, you’ve just found the arbitrage opportunity that funds your next growth phase—but only if you move before everyone else figures it out. AdAge (3 minutes)

Game Your AI Workflow

Treating your AI system like a board game—where you first identify “what are the pieces and what do they do” before optimizing strategy—unlocks building capability that feels impossible when you’re staring at a blank Claude prompt wondering why your AI project stalled out. The insight is that most founders get stuck not because AI tools are inadequate, but because they skip the “teach” phase: defining the discrete components (your meeples, your victory conditions, your resource tokens) before trying to architect the whole system. This week, open a doc and literally list out every tool, prompt, data source, and handoff point in your AI workflow as if you’re writing game instructions for a nine-year-old—give each piece a simple name and one-sentence job description. When you can see your AI system as modular game pieces instead of an overwhelming tangle of prompts and APIs, you’ll spot exactly which piece is missing or broken, and suddenly those “infinite possibilities” compress into 2-3 concrete next moves that actually ship. Every (4 minutes)

Founder FAQ: What are the pros and cons of using Open Source for a startup?

The abandoned npm package you depend on for authentication hasn’t been updated in 18 months, and when it breaks in production, you’ll discover there’s no commercial support to call and your senior engineer just quit—this is how “free” open source becomes a $50K emergency contractor bill at the worst possible moment. The underlying issue is dependency risk: startups treat open source like a buffet, adding packages without checking if projects are actively maintained, have strong communities, or even align with their compliance requirements, then act shocked when a critical library gets abandoned or fails an enterprise security audit. This week, create a simple spreadsheet tracking your top 10 dependencies with three columns: last commit date, number of active maintainers, and whether commercial support exists—flag anything unmaintained for 12+ months or single-maintainer projects as “migration candidates” before they become production emergencies. The payoff is sleeping through the night instead of scrambling when that obscure parser library your entire API depends on suddenly stops working, because you proactively migrated to a well-supported alternative while you still had the bandwidth to do it right. 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

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

Sorry…. I thought I had this post set to publish on Friday, but apparently not. So, this Monday evening you get to feel like it’s Friday for just a moment. Cheers!

Why Bundling Works

The pricing strategy that built Spotify, Netflix, and nearly every successful SaaS company isn't a modern invention. it's a decades-old economic principle that most founders still underutilize. In a classic a16z post, Chris Dixon explains why bundling beats à la carte pricing for information-based businesses. The core insight is that different customers value different products differently. A sports fan and a history buff each top out at $10 for their preferred cable channel, but bundle the two channels and both will pay $13 for the package, generating more revenue while leaving customers feeling like they got a deal. The math works because bundling flattens the demand curve, shrinking the "deadweight loss" of transactions that never happen due to high prices. For founders, the takeaway is practical: subscription models outperform transactional ones, bulk discounts capture value that would otherwise evaporate, and bundling works best when your customers have varied, taste-driven preferences. A16Z (8 minutes)

Annoying VC Questions

Most VC objections aren't questions, they're soft rejections wrapped in polite language, and founders waste months chasing investors who were never going to say yes. Every "show me more traction" or "come back when you have a lead" is a signal about fit and timing, not a to-do list. This week, after every investor meeting, force a binary: is this person genuinely excited or are they stalling? If they can't name a specific milestone that would get them to yes, move them to the update list and stop spending time there. Founders who treat fundraising as a numbers game, running toward conviction and away from maybes, close rounds faster and with better partners. Venture Curator (9 minutes)

The Rise of the Supermanager

Cutting middle management looks like efficiency, but without redesigning how managers actually work, you’re just setting your best people on fire. The real problem isn’t the span of control. It’s that most companies flatten the org chart without changing the job description, training, tools, or expectations. This week, if you’ve recently expanded anyone’s team size, sit down with them and ask two questions: do you have clarity on the three most important outcomes for your team this quarter, and what’s one thing taking up your time that I could remove? Managers who operate with clear goals and fewer administrative distractions retain more people and move faster, and that compounds directly into your ability to execute and fundraise. Fast Company (6 minutes)

Open Source Compliance

The free code powering your product could become your most expensive legal problem if you're not paying attention. Open source software is a startup's best friend until a license obligation gets missed, a vulnerability goes unpatched, or a legal audit reveals a compliance gap that should have been caught years earlier. The fix isn't complicated, but it does require intention. Start by building a detailed inventory of every open source component you use, including version numbers, license types, and how each piece integrates into your product. From there, assign someone to own compliance, implement automated scanning tools, and establish a review process before any new component gets added. The licenses governing open source software change over time, so your compliance program needs regular updates, not just a one-time setup. For founders building on open source foundations, which is nearly everyone, treating compliance as a risk management function from day one is far cheaper than cleaning it up later. Westaway (7 minutes)

Startup Funding Guides

I’ve put together a series of guides to equip founders to excel at fundraising. These guides break down the deal term-by-term and give you negotiation tips so that you can speak to investors with confidence.

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! Welcome to the February of 2026.

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

Pre-Seed

Median Money Raised:

$1,075,000

Median Post-Money Valuation:

$10,000,000

Seed

Median Money Raised:

$4,159,375

Median Post-Money Valuation:

$30,250,000

Series A

Median Money Raised:

$12,012,500

Median Post-Money Valuation:

$77,500,000

Series B

Median Money Raised:

$22,322,222

Median Post-Money Valuation:

$163,333,333

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.