AI Ads Will Be The Next Land Grab (Here's How I'd Play It)

Early Google and Facebook ads felt like a cheat code. Then the advantage disappeared. AI chat platforms are introducing ads now, and this might be another early window. The real challenge is timing. Today I’ll show you how to get that timing right and avoid the common traps I’ve seen across hundreds of SaaS companies. Links on the Video: SaaS Institute: https://tinyseed.com/institute Watch Next: If I Started SaaS in 2026, Here’s My B2B Content Strategy for $1M ARR: https://www.youtube.com/watch?v=Sxn1ji7vYzU SaaS Marketing Strategies That Actually Work in 2026: https://www.youtube.com/watch?v=bUeeVU-OoCM&t=7s About Me: I’m Rob Walling. I’ve been building, growing, and acquiring SaaS companies for nearly two decades. I’ve started six companies (five of them bootstrapped) and exited multiple times, most notably selling Drip in 2016. I’ve invested in over 200 startups, and my focus is on helping founders build multimillion-dollar companies without the pressure of the traditional "unicorn or bust" venture capital model. 🚀 Scale Your SaaS with TinySeed If you are a B2B SaaS founder looking for funding, mentorship, and community, check out the accelerator I co-founded. We designed it specifically for bootstrappers. Apply to TinySeed: https://tinyseed.com 🤝 Join the Community at MicroConf I co-founded MicroConf to create a space for non-venture-backed startups. Connect with thousands of other founders, watch world-class talks, and find the support you need to grow your business. Explore MicroConf: https://microconf.com 🎙️ Listen to Startups for the Rest of Us Check out my podcast, where I’ve shared insights on bootstrapping and growing startups for over a decade. With over 800 episodes and 15 million downloads, it’s the longest-running podcast for software entrepreneurs. Listen here: https://www.startupsfortherestofus.com 📚 My Books on Startups & SaaS I’ve written several books to provide tactical advice on launching, growing, and selling your software company: The SaaS Playbook- My guide to building a multimillion-dollar startup without venture capital. https://saasplaybook.com Exit Strategy: The entrepreneur's guide to selling your business without regret (co-authored with Dr. Sherry Walling): https://exitstrategybook.com Start Small, Stay Small: A developer's guide to launching a startup: https://startsmall.com/ The Entrepreneur's Guide to Keeping Your Sh*t Together: How to handle the psychological pressure of being a founder (co-authored with Dr. Sherry Walling): https://saasplaybook.com/order/p/entrepreneursguide-ebook 👋 Connect with Me Twitter/X: https://twitter.com/robwalling LinkedIn: https://www.linkedin.com/in/robwalling Website: https://robwalling.com