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.

I'm doing something different this week. No roundup, no links, just one conversation I haven't been able to shake. I recently interviewed Dave Evans, co-founder of Stanford's Life Design Lab and author of How to Live a Meaningful Life. What he said was simple enough to fit on a sticky note, but it rearranged something in the way I've been thinking about work, ambition, and what any of it is actually for. I wanted to share it with you while it's still fresh.

BUY HOW TO LIVE A MEANINGFUL LIFE

Stop Searching for the Meaning of Life. Start Making Meaning in It.

Dave Evans has spent 20 years at Stanford helping people find purpose. His advice? Stop asking the big question.

What’s the meaning of life?

It’s the question we’re all circling, whether we admit it or not. It surfaces at 2 a.m. when sleep won’t come. It lurks beneath the Sunday evening dread. It’s there when you watch your kids grow and wonder if you’re doing this right, or when you sit across from your spouse and realize you’ve been talking logistics for weeks without really connecting.

I recently sat down with Dave Evans, co-author of the New York Times bestselling Designing Your Life series and co-founder of Stanford’s Life Design Lab. His new book, How to Live a Meaningful Life, tackles this question head-on. Check out the full interview below.

Or rather, it sidesteps it entirely.

“If I knew the meaning of life, I’d tell you,” Evans said when I asked him directly. “The book doesn’t answer that question.”

Instead, Evans proposes something that sounds almost too simple. A one-word change that reframes everything.

The Preposition Problem

The meaning of life is a deathbed question. It’s aspirational, long-term, and, Evans argues, not particularly useful for the people asking it at 35 or 45 or 55. It’s the kind of question that paralyzes rather than propels.

But there’s a different question hiding in plain sight: How can I make more meaning in life?

“The big question is fine, but it’s not very answerable,” Evans told me. “A different one, how to make more meaning now in the life I’m already living, that we’ve got some ideas about.”

This isn’t wordplay. The shift from “of” to “in” changes everything about how you approach Monday morning, your marriage, your friendships, your role as a parent or colleague or neighbor.

The meaning of life asks you to solve an equation before you’re allowed to feel satisfied. The meaning in life asks you to notice what’s already working, and to design more of it.

Why We’re All Asking This Now

Evans and his co-author Bill Burnett have been teaching life design at Stanford for two decades. But something shifted after the pandemic. The questions got more urgent. The dissatisfaction got louder.

During the Great Resignation, somewhere between 47 and 52 million Americans walked away from their jobs, most without another position waiting. They’d lived through an existential threat. They’d watched people die, or nearly died themselves. And when they looked at the lives they’d built, many found those lives wanting.

“People jumped,” Evans said. “I’m not sure how many of them got to a better place, frankly. But since then, the hue and cry we’re hearing is, ‘It’s just not meaningful enough. It’s just not fulfilling enough. And what did I do wrong?’”

This isn’t just a career question. It’s a life question. The same dissatisfaction shows up at home, in relationships, in the quiet moments when we wonder if we’re actually present to our own existence or just going through the motions.

The Impact Trap

When Evans asks people what would make their lives feel more meaningful, two answers dominate. The first, by a wide margin: impact. Am I making a difference? Am I changing anything?

The second: fulfillment. I just don’t feel fulfilled.

Both answers reveal the same underlying problem. We’ve outsourced our sense of meaning to outcomes we can’t control.

“Impact is a transaction,” Evans explained. “It’s a production outcome. My life is about producing results. Well, that’s a very small part of the human experience.”

Here’s the uncomfortable truth: you can do everything right and still fail. Your carefully planned initiative might not work. Your kids might make choices you wouldn’t make for them. Your marriage might go through seasons where connection feels impossible despite your best efforts. The other 8 billion people on the planet don’t follow your script.

Even when impact works, its shelf life is short. “About five minutes later,” Evans said, “the world asks, ‘What have you done for me lately?’”

If you’ve staked all your meaning on impact, you’re perpetually behind.

Living in the Flow World

Evans draws a distinction between two modes of existence. The transactional world is where most of us spend most of our time. It’s the world of to-do lists and deadlines, of planning the future and evaluating the past. It’s productive and necessary. It’s also, Evans argues, where meaning goes to die.

The alternative is what he calls the flow world. Not the flow state that productivity experts talk about, that feeling of being “in the zone.” The flow world is simpler than that. It’s the awareness of the present moment, the recognition that it’s always now.

“The transactional world lives in the past evaluating what you did, and mostly in the future asking if you’ve pulled this off yet,” Evans said. “It’s never lived in the present moment.”

But wonder, connection, coherence, the things that actually make life feel meaningful, those only happen in the present. You can’t schedule awe. You can’t optimize love. You can only be available for them.

Evans estimates that 99.7% of us spend 98% of our time in transactional mode. We’ve become, in his words, “half-brained people who have lost access to part of themselves.”

The Compass Practice

So how do you shift? Evans offers a deceptively simple exercise called the compass. It asks you to articulate three things.

First, your life view. What do you actually believe about the big questions? Why are we here? What happens when we die? What’s the relationship between individuals and others?

Second, your work view. What is work for? What does it mean to do it well? How does it connect to your life view?

Third, your story. How did you get here? What experiences shaped you?

Then you examine alignment. How well are these three elements getting along right now?

“You can’t experience alignment unless you’ve articulated it,” Evans said.

This isn’t about achieving perfect coherence. It’s about catching yourself in the act of living coherently. Those moments, when your actions match your stated beliefs, when your work connects to your larger sense of purpose, when your story makes sense of your choices, those moments are meaning. Not the promise of future meaning. Meaning right now.

The Paradox of Control

Evans shared something that initially sounds discouraging. The correlation between good decision-making and desired outcomes is zero.

Let that land.

How well you think through something today has no causal impact on the future. Too many variables intervene. Other people make choices. Circumstances shift. The world doesn’t cooperate.

But here’s the twist. Good decision-making, coherent living, still matters. If you ran the same experiment across a thousand parallel universes, the person making thoughtful, aligned choices would succeed more often. The odds improve. You just can’t guarantee any individual outcome.

“You’re not in control of the world,” Evans said. “You’re in control of yourself.” Seneca would have nodded. He wrote that the wise person does everything well while knowing that nothing is promised. The effort is the point. Not because outcomes don’t matter, but because they were never yours to guarantee.

This is actually liberating. If outcomes aren’t the measure, you’re free to focus on the only thing you can actually control: how you show up right now.

Catching Yourself in the Act

The most practical advice Evans offered was this: notice when it’s working.

Not when the outcome worked. When the living worked. When the conversation with your spouse felt connected. When the project at work aligned with what you care about. When the moment with your child, even a mundane one, felt fully present.

“Am I actually present to the reality that I’m in?” Evans asked. “Living coherently, some would say, is about all you get.”

This isn’t about lowering your ambitions. It’s about locating your satisfaction correctly. The meaning isn’t waiting for you at the end of some achievement. It’s available right now, in this conversation, this meal, this evening, this life you’re already living.

You don’t have to figure out the meaning of life. You just have to make more meaning in it.

Happy Friday.

The Adolescence of Technology

Dario Amodei, founder of Anthropic, argues that humanity is entering a “technological adolescence” with AI, facing civilizational-level risks as we approach systems he describes as a “country of geniuses in a datacenter,” potentially within 1-2 years. 1) The first risk is autonomy, where AI systems could develop goals misaligned with human values and potentially dominate through superior capabilities. 2) The second is misuse for destruction, where terrorists or rogue actors could leverage AI to dramatically amplify their capacity for harm. 3) Third is misuse for seizing power, where authoritarian leaders or corporate actors could use AI to gain decisive control over global affairs. 4) Fourth is economic disruption, where even peaceful AI participation in the economy could cause mass unemployment and radical wealth concentration. Fifth is indirect effects, where the rapid pace of AI-driven change could destabilize society in unpredictable ways. Amodei concludes that while the odds of overcoming these risks are good if we act decisively and carefully, we must approach this challenge with sober pragmatism rather than doomerism or denial, avoiding both extreme reactions and complacency. Dario Amodei (45 minutes)

Invisible Beats Sticky

The companies capturing the most attention today are losing—the winners are building products you can ignore. AI agents that negotiate deals while you sleep, interfaces that shrink to a blank field and cursor, hardware going screenless: the pattern is clear, and it flips the last decade’s playbook on its head. The best products now win by reducing the time users spend with them, not maximizing it, because AI can finally execute complex work without human supervision—something no previous technology could do. This week, audit one workflow in your company where your team spends time babysitting software (monitoring dashboards, copying data between tools, checking if something finished), then build or buy an AI agent to handle it autonomously while your team does higher-value work. You’ll free up 5-10 hours per person per week that currently goes to “supervision tax,” and you’ll start learning how to design products where capability increases as interface disappears—the only moat that matters in 2026. NFX (7 minutes)

Delegation Without Anxiety

Most founders have never experienced true delegation—the kind where you hand off a task and genuinely forget about it because you trust it’ll be done right. If you’ve managed a world-class operator, you know that feeling: pure leverage, zero overhead, no follow-up anxiety. AI agents are making this psychology available to everyone for the first time, not just founders who’ve hired exceptional people. This week, identify one recurring task you currently “delegate” but still mentally track (checking if it’s done, fixing errors, providing constant guidance)—maybe it’s data analysis, customer research, or competitive monitoring—and hand it fully to an AI agent with clear success criteria, then force yourself not to check on it for 24 hours. You’ll either discover the agent actually delivers (giving you back 3-5 hours per week of mental bandwidth you didn’t know you were spending), or you’ll identify exactly where AI workflows still break down, which tells you where to focus your product development if you’re building in this space. Jason Fried (2 minutes)

Founder FAQ: What Are the Pros and Cons of Open Source Software?

Most startups use open source software haphazardly and only discover during due diligence that they’ve violated copyleft licenses—mixing GPL code with proprietary code without realizing they’re now legally obligated to open-source their entire product, which can tank acquisitions or force you to rip out and rebuild core infrastructure under time pressure. The difference between “strong copyleft” (GPL) and “weak copyleft” (LGPL) or permissive licenses (MIT, Apache) isn’t academic—strong copyleft means if you link to or incorporate that library, your whole codebase must be open-sourced under the same license, while permissive licenses let you do whatever you want as long as you keep the copyright notice. This week, audit every dependency in your codebase (use tools like FOSSA or Black Duck if you have hundreds), create a whitelist of approved licenses (MIT, Apache 2.0, BSD are safe; anything with GPL requires legal review), and establish a policy requiring engineering leads to get approval before adding any new open source component—no exceptions. If you find GPL violations now, you can quietly replace them; if investors or acquirers find them during diligence, you’ll either kill the deal or get hammered on valuation because you’ve just introduced massive legal risk and technical debt that someone else will have to clean up. 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

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.

Acquired Briefing

Your briefing for the Acquired podcast.

By Kyle Westaway

The Secretive Empire of Mars Inc.

Mars Inc. is a $50 billion global powerhouse that remains 100% family-owned and notoriously private. While famous for M&M’s and Snickers, the company is actually a pet care titan in disguise; that segment generates 59% of its revenue ($29.5 billion) and employs roughly 100,000 of its 140,000-person workforce. Much of Mars’ dominance stems from Forrest Mars, who built a European empire in exile after a falling out with his father. He eventually returned to execute a hostile takeover of his father’s company. Since the 1930s, Mars has enforced a strict open-office policy with no executive perks. Every employee, including the CEO, must punch a time card to earn a 10% punctuality bonus. With the recent $35.9 billion acquisition of Kellanova, Mars continues to transform from a candy maker into a diversified CPG colossus, all while the family ($117 billion net worth) avoids the public eye. Acquired Briefing (22 minutes)

Two Buttons Beat Twenty

The original Cuisinart had two paddle buttons that sound confusing to describe but feel obvious to use—because great interface design optimizes for physical intuition, not feature completeness, and most products fail by adding too many controls instead of perfecting the core ones. When users can operate your product with oven mitts on, in bad lighting, or while distracted, you’ve designed for real-world conditions instead of ideal demos; when you need a manual to explain it, you’ve already lost. This week, open your product and identify the one interaction users repeat most often—then remove every element that doesn’t directly serve that action until what’s left has satisfying tension, clear affordances, and works even when users aren’t paying full attention. You’ll stop losing customers to friction they can’t articulate and start building the kind of intuitive experience people describe to friends as “just works.” Jason Fried (2 minutes)

Chiefs of Staff Playbook

Most founders hire a Chief of Staff thinking it’s a permanent executive role, but the best CoS relationships last exactly 2-3 years before burnout or misalignment kills the value—because the role exists to fill your specific gaps today, not to scale forever, and what you need at 20 people (thought partner who preps decks) is radically different from what you need at 200 people (stealth COO designing org-wide systems). A CoS who complements your weaknesses (technical founder hires finance/ops background, visionary CEO hires operational grinder) becomes a force multiplier only when you’re brutally clear this isn’t forever and co-design their exit into a functional leadership role from day one. This week, if you’re considering a CoS hire, write the MOC (Mission, Outcomes, Competencies) for the next 12-18 months and explicitly include “transition plan at 24 months” as a success metric; if you already have a CoS, have the uncomfortable conversation about what they want to own next and start building toward that internally now. You’ll avoid the passive-aggressive deterioration that happens when talented people outgrow ambiguous roles, and you’ll get 10x leverage during the window when alignment is perfect instead of mediocre performance stretched across five years. A16Z (8 minutes)

Founder FAQ: How Important Service Legal Agreement for a Startup?

Most startups set aggressive SLA targets like 99.99% uptime to look impressive, then burn trust every time they miss by 0.02%—but the smartest companies promise 99.95% and consistently deliver 99.97%, because customers remember broken commitments far more than exceeded ones, and every SLA breach triggers compensation clauses that directly hit your margins. Your SLA isn’t a marketing tool to showcase your ambition; it’s a legal contract that defines when you pay penalties, lose customers, or face termination clauses—and vague promises like “high availability” or “fast response times” create expensive disputes instead of clear accountability. This week, audit your current SLAs (or draft your first one if you’re winging it) and reset every metric to a level you can hit 95% of the time even during your worst operational week, then add specific consequences for non-compliance (like 5% service credit per 0.01% below target) and measurement methods customers can verify independently. You’ll stop bleeding money on penalty clauses, eliminate the passive-aggressive “you promised” conversations that poison renewals, and build the kind of predictable reliability that turns customers into references instead of churn statistics. 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

Happy Friday.

This week in my other newsletter, Acquired Briefing, I'm covering one of my favorite companies of all time. It's also, in my opinion, Acquired's best episode ever. I've been looking forward to sharing this one with you for months. If you aren't subscribed yet and you love business deep dives, join our rapidly growing community and subscribe below to get these directly to your inbox every Thursday.

Acquired Briefing

Your briefing for the Acquired podcast.

By Kyle Westaway

IKEA!

IKEA may be the most singular company in business history. A globally scaled, $50B revenue business with no direct competitors, yet only ~5% market share. One of the world's largest retailers, yet selling only their own products. Generating billions in free cash flow annually, yet having no shareholders. Ingvar Kamprad's vision and discipline are extraordinary. He had a clear mission to bring well-designed furniture to the masses and executed flawlessly, building a $50 billion empire purely off profitability without ever taking external capital beyond an initial 500-krona loan. The evolution from matches and pens to global furniture dominance is remarkable. Kamprad's strategic frugality and long-term thinking created a company that defies conventional business logic at every turn. This folksy Swedish mail order business ended up in living rooms, bedrooms, kitchens, and garages around the globe. And yes, they even sell hot dogs cheaper than Costco. IKEA is a masterclass in counterintuitive strategy executed with relentless consistency. Check out my briefing on the Acquired episode that covers this enigmatic company. Acquired Briefing (23 minutes)

Bet Bigger Always

When Databricks asked a16z for $200k, Ben Horowitz said no—then wrote a $10M check instead, reasoning that if you’re going to build, actually build. Critics have called a16z too loud, too political, too big since 2009, yet Fund III just hit 11.3x net returns and the firm now holds positions in 10 of the top 15 private companies globally. This week, pick your highest-conviction opportunity and ask yourself: are you giving it the resources it actually needs to dominate, or are you hedging with half-measures that guarantee mediocrity? When you believe something will work, over-resourcing it—more capital, more attention, more support—turns conviction into competitive advantage that compounds faster than cautious competitors can match. A16Z News (12 minutes)

Find your screaming fans

Canva launched to 15,000 waitlist signups but only got 500 users on day one—then discovered social media managers were using it obsessively and evangelizing it everywhere, turning lukewarm traction into a word-of-mouth engine that hit 20,000 users in 30 days. This matters because one hyper-engaged cohort that naturally talks about your product online will outperform ten diffuse user groups who like it but don’t care enough to recruit for you—early evangelists aren’t just users, they’re your unpaid growth team. This week, pull your usage data and find the segment with the highest retention and most active sharing behavior, then build one feature or template specifically for them and directly tell them you built it for them—make them feel like insiders. If you nail this, you’ll convert quiet users into loud advocates who recruit your next thousand customers for free, because people who feel seen become your most effective marketing channel. Firstround Review (9 minutes)

Founder FAQ: How Important Licensing Is for A Startup?

Most founders treat licensing as a quick cash grab with big upfront fees, but the smartest deals stack ongoing royalties that turn a single agreement into recurring revenue that compounds as your licensee scales their business using your IP. The structure matters because upfront fees feel safe but cap your upside at exactly the moment your technology proves valuable—royalties align incentives so you win bigger when your licensee wins, creating a revenue stream that funds operations without diluting equity. This week, if you’re negotiating a license, model both scenarios: calculate what 3-5% royalties would generate over 24 months versus a one-time payment, then push for a hybrid structure with a smaller upfront fee plus royalties tied to their revenue or usage metrics. Get this right and you’ll turn IP that’s sitting idle into a funding source that extends your runway by 12+ months without touching your cap table, buying you time to hit the milestones that unlock your next round at a higher valuation. 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

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.

Here’s my January playlist featuring Gracie Abrams, The Lone Bellow, Olivia Dean, Jon Bellion, Bruce Springsteen and others.

The first story this week is a briefing on the history of Rolex as told on the Acquired podcast. It’s not a story about jewelry. It’s a story about branding, survival, and the brilliance of Hans Wilsdorf.

As you may know, I have another newsletter called Acquired Briefing, where I take in-depth notes on Acquired episodes. Over the next month or so, I’m covering some of their most popular episodes, and some of my favorites. Rolex was this week; the surprisingly fascinating story of IKEA is next. I think you’ll really dig it, so sign up to get those briefings directly.

Acquired Briefing

Capturing brilliant insights from the Acquired podcast in a written briefing.

By Kyle Westaway

The History of Rolex

Rolex is a series of paradoxes. They sell obsolete and objectively inferior mechanical devices for 10-1000x the price of their superior digital successors… and demand is stronger than ever in history! Their products are comparable to a Hermès Birkin bag in price, luxury status and waitlist times… yet they produce over 1m units / year (roughly 10x annual Birkin production). They make the most universally recognized and desired Swiss watches… yet their founder wasn’t Swiss and didn’t start the company in Switzerland! If Rolex were publicly traded, they’d almost certainly be among the top 50 market cap companies in the world… yet they’re 100% owned by a charitable foundation in Geneva that (among other things) literally just gives away money to local people in the city. This is one of the most fascinating and admirable companies Ben and David have ever covered on Acquired and one of my favorites. Check out my briefing on Rolex including some iconic Rolex print ads. Acquired Briefing (18 minutes)

Stop to Go Faster

The CEO advice to “focus” fails because it doesn’t explain the mechanism: stopping most things doesn’t just reduce distraction—it literally creates the time and energy to execute the few things that separate thriving companies from dead ones, the way ending toxic customer relationships frees you to turn satisfied customers into fanatics who drive word-of-mouth growth and never churn. The principle underneath: you have fixed time and energy, so every mediocre activity you protect is space stolen from transformative work—chasing every ill-fitting prospect means 1/3 the pitches to good-fit customers at 1/3 the close rate. This week, list everything your team did last month and mark what would happen if you stopped the bottom 70%—not delegated, not optimized, actually stopped—then calculate how much time that frees for your top three priorities. The realistic outcome: you’ll either kill the draining customers, generic marketing copy, and metric-chasing that consumes 60% of your week while delivering 5% of results, or you’ll keep starving in Sylvia Plath’s fig tree, watching opportunities rot while you’re too busy with everything to be great at anything. A Smart Bear (4 minutes)

Growth Costs Money Now

AI companies that celebrate user growth are often celebrating their own bankruptcy—Replit’s gross margins collapsed from 36% to -14% as usage increased, the exact opposite of traditional SaaS economics where more users meant more profit on the same infrastructure. The underlying shift: every time your customer uses your product, you’re paying OpenAI or Anthropic, turning the beautiful fixed-cost model of software into something that looks more like a retail business. This week, calculate your fully-loaded cost per active user (including all LLM calls, not just your average) and compare it to what you’re charging—if your power users cost more than they pay, you’re MoviePass ($9.95/month subscription, $10/ticket cost to theaters). The outcome: you’ll either implement usage-based pricing, subscription overages, or rate limits before your best customers bankrupt you, or you’ll learn this lesson when your gross margins turn negative and investors start asking why growth is destroying unit economics instead of improving them. Every (6 minutes)

Founder FAQ: Why Data Breaching Is Harmful For Startups?

Investors now view data breaches as disqualifying risk signals, not just operational hiccups—a startup that can’t protect customer data gets marked as unable to execute on basic business fundamentals, which tanks your ability to raise the next round even if your product metrics look strong. The underlying issue: breaches trigger cascading damage (GDPR fines reaching millions, customer exodus, reputation collapse that spreads instantly) that investors know will consume management bandwidth and cash for quarters, making you radioactive during diligence. This week, audit your third-party vendors who touch customer data and implement the minimum viable security stack: encryption at rest and in transit, two-factor authentication, regular security audits, and an incident response plan your team has actually practiced—not a 47-page document nobody’s read. The outcome: you’ll either close the obvious security gaps before they become fundraising killers (because one breach announcement between your seed and Series A will cost you 6-12 months and multiple term sheets), or you’ll learn this lesson when a breach forces you to disclose during diligence and watch investors ghost you regardless of your growth rate. Westaway (5 minutes)

Startup Funding Guides

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

SAFE: Guide / Video

Convertible Note: Guide / Video

Seed: Guide / Video

Series A: Guide / Video

Web3: Guide / Video

Is the Billable Hour Right for Startups?

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

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

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

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

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

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

Post of the Week

Happy Friday! Welcome to the January of 2026.

Check out the the December 2025 venture capital funding data from AngelList.

Pre-Seed

Median Money Raised:

$660,000

Median Post-Money Valuation:

$10,000,000

Seed

Median Money Raised:

$4,232,800

Median Post-Money Valuation:

$28,600,000

Series A

Median Money Raised:

$17,800,200

Median Post-Money Valuation:

$102,300,000

Series B

Median Money Raised:

$17,800,200

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.