Mostly Technical 106: We've Got ARR!
Nov 11, 2025
The hosts dive into the 20-year journey of HelpSpot, revealing insights on sustainable SaaS and customer profiles. Aaron shares his surprising Twitter success and the strategies behind it. They discuss the importance of managing customer concentration and how modest subscriber counts can sustain a business. Additional topics include parenting challenges and balancing work with family logistics. The conversation wraps up with exciting updates on Database School and the launch of subscription services.
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From Spam To A Surprise Birthday Invite
- Aaron recounts getting a Paperless Post invite that he first assumed was spam and then realizing it was a real birthday invite for twins.
- The spontaneous decision to attend led to a delightful family outing and new neighborhood friendships.
Introduce Yourself To Make Connections
- Introduce yourself to other parents using an easy, natural opener like noticing twins.
- You can form real friendships and get invited to events by making small social gestures.
Twenty Years Running HelpSpot
- Ian reflects on HelpSpot's 20-year run and how it feels both long and like it always existed.
- He credits a small, stable team and long-term customers for sustaining the business.
