Most founders spend years perfecting a dashboard. George Hartley — who built and sold SmartrMail (acquired by Relay Commerce in 2022) and co-founded Bluethumb, Australia's largest online art marketplace — is betting his third company on removing it entirely. Nitrosend runs from inside Claude, Cursor, or ChatGPT, with AI agents doing the majority of the work.

In this episode, George walks through the decision to rebuild an email company from scratch with the same team, the acquisition deal that nearly collapsed under a stalled LOI, and why he now believes the addressable market for email isn't measured in people — it's measured in agents.

George Hartley has spent over a decade building and scaling companies — Bluethumb, an online art marketplace he co-founded in 2012, and SmartrMail, an e-commerce email platform he built, grew, and sold to Relay Commerce in 2022. Both experiences shaped the decision behind his current company, Nitrosend: an agent-first email platform built for a world where AI agents, not humans, do most of the operating work.

This conversation covers what it's like to reassemble a founding team for a third company, the tradeoffs between staying capital-efficient and being able to seize an opportunity, and why George now thinks about total addressable market in terms of AI agents rather than people.

Key Takeaways

1. A signed LOI doesn't guarantee a deal. George's SmartrMail acquisition was locked into an exclusive agreement for weeks before the buyer walked — a reminder that exclusivity protects the buyer's optionality, not the seller's certainty.
2. Being too capital-efficient can cost you the upside. George names "well capitalized" as a top value for Nitrosend specifically because running lean in prior companies meant sometimes not having the resources to seize a real opportunity.
3. Planning assumptions fail — build a workaround, not a delay. When Nitrosend's official AI-platform app store listing stalled, the team shipped an agent-onboarding skill instead of waiting on approval.
4. Total addressable market may need to be recalculated around AI agents, not just people. George reframes Nitrosend's TAM from "half the internet" to potentially "a hundred billion agents" as autonomous agents begin operating businesses.
5. A high failure rate on new ideas is normal, even for a repeat founder. George estimates roughly two-thirds of his own initiatives don't move the needle — the discipline is in testing quickly, not being right the first time.

George Hartly is the founder of Nitrosend, an AI-native can find George and Nitrosend at https://nitrosend.com

00:00 The Hundred Billion Agent Market

01:29 Building a Game With AI

05:15 The Drive to Keep Creating

08:05 Turning Rejection Into Opportunity

12:46 Building Australia’s Largest Art Marketplace

16:55 Launching SmarterMail

19:01 Selling the SaaS Company

25:07 The Birth of NitroSend

29:58 Finding the Ideal Customers

32:51 Lessons From Previous Startups

44:13 Preparing for an Agentic Future

53:22 Practical Advice for Founders

Guest: George Hartley

Title: Founder, Nitrosend (also founder, SmartrMail — acquired by Relay Commerce, 2022; co-founder, Bluethumb)

Company: Nitrosend

Website: https://nitrosend.com/

LinkedIn: https://www.linkedin.com/in/gthartley/