
Episode #20
The Bootstrap Founder's Bet on Agentic Support
What do you do when your bootstrapped business hits $5M ARR but stops acquiring new customers entirely? Alex Turnbull didn't wait for the answer. He shut it down and started over. Twice. Host Alex Theuma speaks with Alex Turnbull, CEO of Helply, formerly CEO of Groove for 15 years. With 100 companies already committed with deposits and a $165K MRR pipeline before launch, Turnbull explains why he killed two products to build one agentic-first platform, no seats, no legacy baggage. In this episode, we explore: (00:41) Why Groove became a textbook NRR zombie at $5M ARR (03:21) The decision to bolt AI onto Groove and why it failed (08:13) Helply V1 reaches $1M ARR in 12 months then gets shut down (11:01) Why owning proprietary data is the real moat in agentic support (15:08) How Helply's ICP and ARPA shifted dramatically from Groove (19:20) The no-seat pricing model and why incumbents cannot copy it (23:04) Turnbull's honest warning to legacy SaaS founders still on the fence (28:19) How vaporware at SaaStr AI Conf produced 125 qualified demos The AI Revolution Show is the intelligence podcast for B2B software founders navigating the platform shift, the founders building through it, and the founders already on the other side. Hosted by Alex Theuma, founder of Shift AI Events. Subscribe so you don't miss the next episode. This episode is brought to you by Leapsome. For more information, visit Leapsome: https://hubs.li/Q04xm8f_0 .

