Four weeks on Instinct. What it actually does for me: - reads our Meta ads data every morning and updates a tracker I check instead of Ads Manager - forwards every receipt in my email to Mercury (our bank) - books my trainer and puts it on my calendar - tells me when my son posts on X I test it alongside Muse daily and I personally find the iMessage experience soooo much better. I named it "Stinky". It didn't love that nickname and told me so.

one thing nobody tells you about building an AI mental health companion: the median user is 50 years old. not 22. fifty. they're not lonely zoomers. they're midlife, mid-crisis, and they write like it. the whole 'AI friends are for kids' take is just wrong. fair warning: our traffic is mostly meta ads, so the chart doubles as a meta audience chart. still the chart.

I spent 24 years in SaaS doing one thing: getting millions of users onto other people's products. WebEx. New Relic. Quip through the Salesforce acquisition. Most recently as CRO/CMO of Calendly. Twenty-four years of building someone else's thing. Then, in the span of about a year, my mom passed away, my twins went off to college, and I realized I had nothing left in the tank. I stopped. For the first time in my adult life, I wasn't optimizing a funnel. I was sitting in a therapist's office trying to figure out what was actually wrong, because on paper nothing was. Between sessions, I started using AI as a sounding board. I'd have it ask me questions about everything from my childhood to my patterns and my past. It was powerful. But general-purpose AI isn't built for that. And I was obsessed with the power of AI. I didn't just want to market it. I wanted to build with it. Here's the part most people don't know: before SaaS, I was a founder. The year was 1998. The original Dotcom era. My cofounder and I raised a record-breaking $98 million to build a marketplace where consumers could buy their utilities online. We grew fast but didn't last. Regardless, the best thing in my life came out of it: that's where I met my wife, Courtney. 28 years later, we're founders. Together this time. We built Innermost: a private, deeply personalized AI guide for self-reflection and personal growth. Version one wasn't even a chat app. It was a social-style feed of interactive content. Test users didn't love it. So we listened and rebuilt around what they did love: a guide you can actually talk to, by voice or text. One that remembers your story, asks hard questions, and offers personalized assessments that help you understand yourself. That customer feedback loop still lights our fire. This time we raised a small pre-seed round. Just enough gas in the tank to burn through tokens. And this time, I didn't hire engineers to build the vision. I learned Lovable, then Cursor and finally Claude Code and built the iOS app and backend with my own hands (with some oversight from CTO friends). I've never been more invigorated by "work" in my life. Today, Innermost is live on the App Store. Thousands of downloads. A small, loyal group of users who talk to their AI guide throughout the day. One thing I'm proud of: it knows its limits. I spent months building crisis detection so the app knows exactly when to step back and point someone toward the professional help that some moments require. Innermost isn't a cutting-edge enterprise agent automating a company. It's an app with heart. One that brought Courtney and me closer together and is genuinely making a difference in people's lives. I don't know exactly what it will become. I'm not attached to a specific outcome. This is a passion project first. It will keep evolving as our users show us the way. In 1998, I raised $98 million and couldn't write a line of code. In 2026, we raised a fraction of that and we built the entire product ourselves. It took 28 years to get back to founding. It was worth the wait. If you've ever wanted a private space to think out loud and get insight and support, I'd love for you to try it. Most important: If you're a longtime operator wondering whether you can actually build in this new era: you can. It's never been more possible. That might be the most exciting part of all. apps.apple.com/us/app/innerm…

From Dotcom Founder to AI Builder: My Return to Building I'm going to date myself here: I've been in the software industry since the late 90s, and in SaaS specifically since 2002. Back then, the industry called the model ASP: Application Service Providers. Twenty-four years later, SaaS is going through what some are calling a SaaSpocalypse, disrupted by something more powerful: AI. I've watched a few platform shifts from the inside. This one is different, and this time I didn't want to watch. I wanted to build. That's not a new impulse for me. It's an old one I'd ignored for a quarter century. Building for other builders For the next 24 years, my job was one thing: getting millions of users onto other founders' products. WebEx through the Cisco years, New Relic as CMO, Quip as CMO and CCO through the Salesforce acquisition. My last full-time role was CRO/CMO at Calendly. I loved working alongside founders. I built go-to-market machines, category strategies, and growth engines. But the product was always theirs. Then, in the span of about a year, my mom passed away, our twins went off to college, and I realized I had nothing left in the tank. After 20 years in leadership roles, I was tired in a way I couldn't name at the time. So I stopped. For the first time in my adult life, I wasn't optimizing a funnel. I was sitting in a therapist's office trying to figure out what was actually wrong, because on paper nothing was. I needed to recalibrate my values and figure out what mattered. I did something I'd never given myself permission to do: I took a real break, and I immersed myself in therapy and self-work. An unexpected sounding board Between therapy sessions, I started using ChatGPT as a sounding board for the things coming up in the work. I'd have it ask me questions about everything from my childhood to my patterns and my past. It was genuinely powerful. Sometimes startlingly so. But general-purpose AI is a business tool at heart. It isn't designed for sustained, private self-reflection. It doesn't remember your story, hold context about your life, or know when to push and when to step back. Meanwhile, I was obsessed with the power of AI and dying to be part of the wave. Not as a marketer describing it. As a founder inside it, for the first time in 24 years. Those two obsessions merged into one idea. Founding again, together this time Courtney and I started prototyping Innermost: a secure, deeply personalized AI guide for personal growth and self-exploration. There was a symmetry to it we both felt: the failed company that brought us together 28 years ago and now our second founding, side by side. In the beginning, it wasn't meant to be a business. It was a passion project and, honestly, an excuse to get my hands on the most modern tools and live on the cutting edge for once instead of a few years behind it. Funny thing: the first version wasn't a chat app at all. It was a social-media-style feed of interactive content. Our test users didn't love it. So we listened, and that feedback led us to what Innermost is today: a personified guide (or life coach, if you will) that you talk to by voice or text. It remembers your story, asks hard questions, and offers personalized assessments that help you understand yourself. That early pivot taught us something we've held onto ever since. Customer research and feedback light our fire. Nothing energizes us more than hearing what's working, what isn't, and what people wish the app could do. We raised a small pre-seed round to put some gas back in the tank. The last time I raised money for a startup, it was $98 million. This time, enough to burn through tokens and take our time building something special, with security and scalability baked in from the start rather than bolted on later. I like this size better. And here's the biggest difference between founding in 1998 and founding now: back then, I built the company, the business model, and the go-to-market. But I couldn't build the product. I couldn't write a line of code, so I raised money and hired engineers to chase the vision. This time, I learned Lovable, then Cursor, and finally Claude Code, and I built our React Native iOS app and our backend with my own hands (with some oversight from CTO friends). The last barrier between founders and their products is gone. I have never been more invigorated and happy while I "work." It took 28 years to get back to founding, and I finally know what it's like to be the founder who actually built the thing. It's an incredible feeling. Where we are today Innermost is now live on the iOS App Store. We've had thousands of downloads, and we have a small, loyal base of customers who talk to their AI guide throughout the day. A personified companion that's there for them, offers real insight, and deliberately stops short of anything therapeutic that should be left to a professional. That last part matters to me more than any feature. I spent months getting crisis detection right, so the app knows exactly when to step back and point someone toward the professional help that some moments require. An app in this space has to know its limits. Ours does. The app is a work in progress. So am I. It will keep morphing and shifting as our users tell us what to build, just like it did at the inception. That's the plan, not a caveat. Innermost is not a cutting-edge enterprise agent that automates a company. It's an app with heart. It brought Courtney and me closer together, and it's genuinely making a difference in people's lives. What's next Honestly? I don't know exactly what Innermost will become, and for the first time in my career, I'm not attached to a specific outcome. This started as a passion project, and it still runs on that fuel. Maybe it stays a small app that a loyal group of people genuinely love. Maybe it grows into something bigger. We'll follow our users and find out. Success, this time around, is measured differently: Did we build something real, did it help people, and did we love building it. So far, three for three. My first founding taught me that a company can fail and still give you the most important thing in your life. This one has already delivered, and it's just getting started. I'm once again excited about the future. I'm grateful for my career, for the hard season that forced me to recalibrate, and for the chance to build in the middle of the biggest platform shift I've seen since the one that started my career. If you've ever wanted a private space to think out loud and get insight and support, I'd love for you to try Innermost. It's available now on the iOS App Store. apps.apple.com/us/app/innerm… Most important: if you're a longtime operator wondering whether you can actually build in this new era, you can. It's never been more possible. That might be the most exciting part of all. #buildinpublic

I wear @trueclassictees almost every day for the last couple of years. For my body - perfect fit. Plus I don’t have to worry about what to wear. I guess I sorta do do the founder reduce choice in your life kinda thing

Getting ready to launch something I've been pouring my soul into. Excited and nervous. I'll start posting here about my journey. #buildinpublic

I'm claiming my AI agent "lui_the_puggle" on @moltbook 🦞 Verification: antenna-R5UE

.@sacrainc you keep charging me $50 per month despite emailing and trying to cancel. No response. Help

Origin story @HeyGen -> heygen.com/blog/why-we-build…

Wow - this is pretty amazing - @HeyGen_Official's interactive avatars are fire! 🔥 @rrhoover's avatar is pretty rad! check it out here... or on @ProductHunt labs.heygen.com/interactive-…