TLDR Founders

TLDR FOUNDERS 2025-08-18

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01GENERAL

Sponsored

5 HARD-LEARNED LESSONS ABOUT SCALING PRICING

Remember when you could ship a pricing change in an afternoon? Then you scaled, and suddenly every pricing tweak needs an engineering ticket, a sprint, and a prayer that nothing breaks in production.

metronome.comSponsor

03STRATEGIES & TACTICS

FOCUS ON FULL FUNNEL SEO NOT JUST THE TOP

SEO teams obsess over rankings and traffic, but ignore what happens after someone clicks. This kills SEO's value when clicks decline. The fix is full-funnel SEO that follows the entire customer journey. Activation SEO targets searches like "how to import contacts into [product]" - boring queries that determine if trials convert to paid. Retention SEO mines support tickets for friction points. When frustrated users Google problems before calling support, you'd better rank for those queries or Reddit will. Expansion SEO helps existing customers upgrade by ranking for tier comparisons and referral searches. The real measure of SEO is about being present with helpful answers at every critical moment.

productledseo.com5 min read

GETTING STARTED WITH USAGE-BASED PRICING

AI features create a pricing nightmare because some customers barely touch them while others 10x their usage overnight. Kyle Hart built Toast's pricing playbook from $0 to $100M ARR and says customers claim they want usage-based pricing but actually hate the variability. His approach is similar to how you'd test a new feature. First, audit what you have - which features do reps discount most? What are customers actually using? Then, form 2-3 mock pricing pages to test in real sales calls. Slowly build your conviction over time before making the swap.

dearstage2.com6 min read

WHAT TO DO MORE (AND LESS) OF

Most teams know what good product development looks like, but can't figure out why they're not doing it - the answer isn't what to add, it's what to stop. The author studied high-performing teams and found they create space for the right behaviors by killing the wrong ones. They weave context into every discussion instead of jumping straight to solutions and pretending they know everything. They ship meaningful progress weekly instead of getting stuck in analysis paralysis for months. They question year-old commitments instead of blindly executing plans made when everything was different. For your next product planning session, try asking, “What would we need to stop doing to make room for what matters?”

cutlefish.substack.com6 min read

04TOOLS & RESOURCES

Sponsored

GET YOUR STARTUP FOUND IN AI RESULTS AND GOOGLE — AND BE SECURE, TOO

OpenVPN is featuring startups that use their business VPN on the OpenVPN website [12]. It's a great chance to get a link from a high-authority domain, expose your brand to 3M+ monthly visitors, and show that you care about data security. All you need to do: Sign up

openvpn.netSponsor

SCHEMATIC

Schematic is a modern monetization platform for SaaS that powers usage-based billing, customer portals, and pricing flows to help teams ship pricing faster and grow revenue.

schematichq.comTool

DEN

Den is a multiplayer AI agent builder that centralizes your chats, docs, and agents so humans and AI can collaborate and automate work in one shared space.

getden.ioTool

MACAULAY

Macaly turns conversations into working apps and websites, letting you build by simply describing what you want—no coding required.

macaly.comTool

05MISCELLANEOUS

PRODUCT WON'T END AT CHAT

AI capabilities have run so far ahead of product design that we could stop all model development today and still have years of work left. Everyone's bundling everything into chat apps, but chat sucks for depth, workflow, and longitudinal data. There's a reason AI code generators are IDEs, not text boxes. We'll see the same unbundling that happened with Craigslist - horizontal chat platforms will disaggregate into deeper, purpose-built apps. Any guidebook or professional guide is a candidate for standalone AI apps that go beyond chat. The optimal product has yet to be discovered, but chat won't cut it.

99d.substack.com5 min read

WHY THE VENTURE CAPITAL SECONDARY MARKET IS BOOMING IN 2025

While everyone waits for the IPO window to reopen, secondaries quietly hit $152 billion in 2024, up 39% year over year. What started as a liquidity hack is now essential infrastructure. LPs tired of waiting can sell their fund stakes. Founders can give employees partial cash-outs without forcing an IPO. GPs spin their best companies into continuation vehicles to hold them longer while still returning cash. The numbers are wild. VC secondaries jumped from 16% of deal activity in 2020 to 29% in 2024. Secondaries aren't a workaround anymore. They're how venture capital actually works when traditional exits take over a decade.

thevccorner.com7 min read

SF TECH CEO OFFERS BUYOUTS TO LET WORKERS FLEE 'EXTREME' WORK CULTURE

Cognition's CEO, Scott Wu, offered buyouts to Windsurf employees after acquiring the company, emphasizing a demanding work culture with 80+ hour workweeks. He clarified that those rejecting the buyout must commit to an all-consuming environment. Wu accelerated share vesting schedules and laid off 30 staff, leaving 200 workers to decide on the buyout.

links.tldrnewsletter.com4 min read