"This is not a product category." "They're not actually going to work on this." "They're going to acquihire themselves to somebody." When Christina Cacioppo (@christinacaci) first pitched her startup in 2018, investors couldn't believe anyone would want to build compliance software. Eight years later, @TrustVanta works with 16K customers from Lovable to Icelandair, earning a $4.2B valuation. Now, she faces the opposite question: With AI, can't anyone build this? How does Vanta stay ahead of a new wave of hype-y startups? "I subscribe to the 'never let them see you blink' school of thought, she tells me. On The Upstarts Podcast, Cacioppo shares how she created value in a sleepy category; how she prioritizes “infinity things” as a startup unicorn CEO; and why when it comes to good security hygiene, we could all spend more time brushing our teeth. Plus, she shares her Upstart Moment: working to re-think, and future-proof, Vanta's software business in the face of powerful AI models. This season is presented by @Rippling 🫡 CHAPTERS 00:00 Introduction 1:39 What Vanta does 5:26 Selling to other startups 9:28 How AI agents change ‘pretty much everything’ 14:06 Christina’s *real* founder origin story 16:23 Underdog fundraising and gaming VCs 18:59 The problem with startup valuations 24:08 Turning LinkedIn ‘cringe’ into customer traction 26:41 Reinventing Vanta with AI 33:43 Whether AI could clone Vanta 35:23 ‘Never let them see you blink’ 37:24 Avoiding burnout with ‘infinity things’

VoidZero, the team behind Vite, Vitest, Rolldown, Oxc, and Vite , is joining Cloudflare. Vite stays open source, vendor-agnostic, and built for everyone. cfl.re/3Q1XYSX

BIG DAY! @voidzerodev is joining @cloudflare 🚀 before anything else: @vite_js is very much remaining open source, and will always remain that way, with robust ongoing investment we're also going to keep making cloudflare the best place for building applications! thrilled to have @evanyou and team join us to help us on that mission. blog.cloudflare.com/voidzero…

Really loved getting to speak to @nickfrosst and diving deep into the @cohere story for this piece for @BetaKit’s Most Ambitious 2026! Also, amazing to have a byline on BetaKit again after so many years! ❤️ betakit.com/canadas-ai-champ…

Shopify CEO Tobi Lutke explains Goodhart’s law and why he doesn’t like KPIs or OKRs “Goodhart’s law is real. The moment a metric becomes a goal, it’s no longer a useful metric… No metric by itself is a complete heuristic for a complex business. There’s a million different tensions in a company, and you can’t keep all of them in harmony by optimizing for one thing.” For this reason, Shopify doesn’t use KPIs or OKRs. But as Tobi explains, this doesn’t mean they don’t value data and metrics. “We are extremely data informed. We have invested enormous amounts of money and time into systems that give us basically everything at our fingertips… But what Shopify attempts to do is just not over-fit for what’s quantifiable.” People love optimizing for highly-quantifiable things because there’s immediate gratification that comes from seeing a number go up. But Tobi thinks that the most important aspects of a product are rarely quantifiable: “The overlap of the most valuable things you can do with a product and the things that happen to be fully quantifiable are like maybe 20%. Which leaves 80% of a value space unaddressable by the people who only look at quantifiable things.” He continues: “Shopify is comfortable with unquantifiable things like taste, quality, passion, love, hate… The sort of deep satisfaction that a craftsperson feels when they’ve done a job well is actually a better proxy if you allow it to be.” They then have robust analytics systems that tell the company if something’s wrong or a new rollout breaks something. “We think about it as a cockpit for a pilot. The decisions are still made by pilots, and we think this leads to better results… I think there needs to be more acceptance in business of unquantifiable things… And then metrics take a support function.” Source: @lennysan (Feb 2025)

We’re introducing the Cursor SDK so you can build agents with the same runtime, harness, and models that power Cursor. Run agents from CI/CD pipelines, create automations for end-to-end workflows, or embed agents directly inside your products.