Blog

In this episode of The SAAS Operators Podcast, we sat down with Jacob Posel to talk about his journey navigating the earliest stage of building a SAAS business and how he is thinking about AI, distribution and product-market fit. Jacob shares why chasing the “biggest opportunity” is not enough without obsession. How his background in marketing and advertising gives him an edge. He explains why stealth mode matters, how he is thinking about first hires, and why great tech is still the foundation of any surviving SAAS business. We talk about Icon’s controversial move into managed services, whether software as a service companies are destined to become... just service companies, and the reputational risks of overpromising when you only get so many first impressions. From cycle times in SAAS, to the important of momentum, and how AI is changing the way founders meddle directly in product development, this conversation is an exploration of how SAAS businesses starting today in 2025 operate.

In this episode of the SaaS Operators Podcast, we sat down with Jason Lemkin who explains how AI and Shopify have completely reshaped the landscape, eliminating lifestyle businesses and forcing founders to adapt or get steamrolled. He describes how defensibility in B2B SaaS is eroding, success in the Shopify ecosystem, and why hitting $10M ARR no longer guarantees a path to $100M. Jason Lemkin shares his rule for founders and execs. Deploy one new AI tool every month. Speed, brand, and execution matter more than ever. The episode closes with an honest take on raising capital in ecom SAAS, why VCs avoid the category, and what it will take to build a truly fundable business in the age of AI.

In this episode of the SaaS Operators Podcast, we’re joined by Dan Pantelo, founder of Marpipe, for a deep dive into SaaS growth strategy, pricing, and go-to-market plays. We kick off with Judge.me’s $12M ARR business, debating whether it’s a massive success or still untapped potential, and explore why moving upmarket is often easier than defending the bottom. Rishabh shares how a $500/month SMB version of Fermat is scaling quickly through cold calling while email struggles in crowded inboxes. Dan walks us through Marpipe’s new free feed management tool and the upsell strategy behind it, sparking a discussion on “good enough” vs. “better” positioning. We wrap with a breakdown of SaaS pricing myths, the real role of subscriptions, and how events plus consistent social content create the “everywhere” effect.

In this episode of The SaaS Operators Podcast, we dive into the tradeoffs of venture capital, bootstrapping, and the gray area in between. Josh Perk, Founder & CEO of Vector, joins the crew to talk about building a YC-backed company and why his $130K AWS bill makes bootstrapping impossible. The conversation covers how Vector is taking on giants like 6sense and Demandbase with contact-based marketing, why fundraising isn’t just about dilution but also about partner quality, and how capital markets are shifting as funds scramble to deploy earlier. We talk about secondary liquidity, founder motivations, and the real math behind VC outcomes, and when it makes sense to turn down the sure thing. The conversation wraps up on the messy reality of employee equity, acquisitions, and how founders navigate the tension between personal wealth, team outcomes, and long-term vision.