Happy Friday.
My October playlist leans into folk and country, with Noah Kahan, Sam Barber and a pairing of Wynonna with Iron & Wine.
Faster Code, Slower Delivery
AI can make coding faster while making software delivery slower. Francisco Trindade describes a 10-engineer startup team that hit a four-week feature deadline, then spent two weeks largely fixing bugs. The release looked fast until you counted the cleanup and the customers living with it. More code can overwhelm review, testing and decision-making, turning feedback loops into formalities. His three principles: 1) Define outcomes in customer value, so success means solving a business problem rather than opening more pull requests. 2) Manage the whole journey from idea to production. If planning takes longer than development, another coding agent is solving the wrong bottleneck. 3) Measure team productivity. An engineer running 100 agents can create 100 times more work for somebody downstream. The useful measure is how quickly a change delivers value to customers, including the time spent correcting it. My friend Francisco wrote a book on this, aptly called Leading Effective Software Teams. Check out this post and if you dig it, but the book. Francisco Trindade (6 minutes)
The Craft of Sales
AI can automate sales administration. It cannot reliably read a room, earn trust or help a buyer navigate an internal fight over budget. The human work comes down to five habits: 1) Treat prospects like friends. Be useful beyond the deal instead of sending another generic follow-up. 2) Arrive prepared. Know the product, understand the buyer’s industry and keep your promises. 3) Read the room. An objection may hide uncertainty that another pitch will not resolve. 4) Make buying easier. Write the business case, prepare your champion for objections and map the evaluation with owners and deadlines. 5) Ask direct questions about priorities, urgency and whether you are the preferred vendor. Then add discipline: protect prospecting time, requalify deals weekly and reserve 10 minutes before each call and five afterward. One founder emailed a $300,000-plus proposal and lost the deal without hearing the price objection. Present important proposals live, where you can hear the hesitation and respond. First Round (27 minutes)
Platforms and the Open Internet
What if Big Tech’s recurring controversies are symptoms of a larger change in the internet itself? We have focused on individual scandals while overlooking the shift from open protocols to privately governed platforms. Email and the web let people build at the edges without asking a central owner for permission. Search engines, social networks and video platforms solved real problems, then became the environments where much of digital life happens. Their rules and recommendation systems increasingly shape what people encounter and how they participate. The question is whether companies built to predict behavior still understand the societies they serve, or whether their own models have become substitutes for that understanding. The platforms have not collapsed or lost their users. That continuing success may be what makes the structural change so difficult to see. Techdirt (7 minutes)
Founder FAQ: How Can Startups Avoid Wasting Money on Lawyers?
A $2,000 legal bill that turns into $20,000 is often a management problem as much as a pricing problem. Founders can control both. Start with a lawyer who understands startups, so you are not paying someone to learn standard venture practices. Keep incorporation documents, approvals and equity records organized instead of handing counsel a pile of unrelated folders. Before asking a question, learn the basics and send a clear description of the decision you need to make. Invest in reusable contract templates and a negotiation playbook that identifies preferred terms and acceptable compromises. Agree on flat fees whenever possible, or a cap when they are unavailable. A cap limits the surprise, but it can still become the firm’s target. Use startup counsel for routine work and bring in larger firms selectively for specialist questions. Saving money on legal starts with making the work easier to scope, repeat and price. 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.
Convertible Note: 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.