Strategic Friction Can Double SaaS Trial Conversions
Adding friction to your trial funnel can double your conversions. Or it can kill them. The difference comes down to your product, your customer, and their state of mind when they sign up. I sat down with Ruben Gamez of SignWell and Bidsketch to answer listener questions that turned into one of the deepest conversations I've had on the show. We covered why friction works completely differently for his two SaaS products, how to test without enough volume, and what it actually takes to develop real product instincts as a bootstrapped founder. Check it out 👉 https://lnkd.in/ezKiG_hT
PE Demands AI Moats for SaaS Deals in 2026
Some private equity firms in 2026 won't show your SaaS to their investment committee without at least one AI moat. I sat down with Einar Vollset of Discretion Capital , who advises on B2B SaaS exits between $2M and $20M...
$2 Trillion Evaporated From SaaS. I’m Not Worried
Rob Walling opens by noting a $2 trillion market‑cap wipe‑out in public SaaS during early 2026, dubbing the headlines a "SaaS apocalypse." He argues that the panic is misplaced for bootstrapped founders, whose business models differ fundamentally from enterprise‑scale, seat‑heavy public...
AI Helps Operations, Not Copy: Prioritize Human‑First Marketing
Most founders are using AI wrong for their marketing. I sat down with Taylor Hendricksen , a full-stack marketer who has managed tens of millions of dollars in ad spend. We talked about where AI is genuinely useful in your...
Redefining Profit: Eric Ries' Incorruptible Vision
Tobacco companies are technically profitable. So are Ponzi schemes. Eric Ries says the definition is broken, and he has a better one. The author of The Lean Startup and his new book Incorruptible joined me to revisit the ideas that...
Start a SaaS From $0 in 2026
Rob Walling explains that launching a SaaS in 2026 requires virtually no cash, only strategic focus. He argues the real expense is acquiring paying users, not polishing code, and advises founders to defer formal entities until revenue materializes. He outlines a...
Pivot to Project Work Generates $10K‑20K Monthly
A TinySeed founder had no product-market fit, and the company wasn't making money. Two months after deciding to pivot into project-based work, they were generating $10,000-$20,000 a month. No inbound traffic, no big audience. In this episode, I talk about...
Escape Golden Handcuffs: When to Go All‑In
How do you leave a $400K salary to go all in on your business? I answer that and more in this round of listener questions episode. We cover: • The golden handcuffs problem and how to escape it • When...
Is Mailchimp the Greatest Bootstrapped SaaS Ever?
Mailchimp’s rise from a 2001 side‑project email tool to a $12 billion bootstrapped exit is the focus of this episode of SaaS Legends. The founders, Ben Chestnut and Dan Kurzius, repurposed abandoned e‑greeting code to solve a painful email‑newsletter problem for their...
Charge Your First Customer or Offer It Free?
Should your first customer pay you, or get your product for free? In this episode, I answer listener questions on charging your first customer, what metrics to track for a transaction fee-based SaaS, and when freelancers help vs. hurt your...
Every Story You Tell Yourself About Churn Is Wrong
Rob Walling’s video challenges the stories founders tell about churn, arguing that most assumptions are wrong and that churn is a metric that can make or break a SaaS business. He explains that even a 5% monthly churn forces a company...
AI Can Code, but Not Choose the Right Product
AI can help you write code, draft cold emails, and generate blog posts. But there's one of the core four SaaS skills where AI falls flat: Product. Knowing what to build, what not to build, and how to listen to...
Running SaaS in a Post‑Software, Agentic Era
.@TheCraigHewitt takes the stage to close out #MicroConf 2026 talking about how to run a SaaS in a post-software / agentic world. https://t.co/zzixtMeUsl
Defining SaaS: What Truly Counts for Founders
Is your product actually a SaaS? I gave the definition of SaaS more thought than I ever have before, and it turns out ChatGPT and I disagree on a few things. In this week's episode, I answer listener questions covering...
StartupS Pod Celebrates 16 Years And
16 years ago today, the first episode of @startupspod went live. It’s now old enough to drive. 825+ episodes later, still shipping. Appreciate everyone who’s listened, reviewed, shared, or sent in a question along the way. https://t.co/ViciIzm0Bu