106: We've Got ARR! - Mostly Technical - Audio Brevity | Audio Brevity
106: We've Got ARR!
Mostly Technical

106: We've Got ARR!

Nov 11, 2025 74m
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Episode Description

Ian and Aaron talk about 20 years of HelpSpot, Aaron's big week on Twitter, and....talk about burying the lede....Aaron's got ARR!  Subscription revenue!  It's happening!

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  • (00:00) - A Weekend Story
  • (15:25) - Sick Kids
  • (20:12) - Laravel New Update
  • (22:40) - 20 Years of HelpSpot
  • (37:27) - Ian's Hiring
  • (43:03) - Aaron's Big Week on Twitter
  • (53:20) - Database School Update
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AI-Generated Summary

Weekend Stories and Parenting Adventures

In this segment, Ian and Aaron share amusing weekend stories, particularly about attending a birthday party for their kids. Aaron recounts an experience where he initially mistook an invitation for spam due to not having spoken to the host in years. However, the event turned out to be a wonderful family outing where Aaron's children had a great time, and he forged new connections with other parents, emphasizing the importance of community and making friends in unexpected places.

20 Years of HelpSpot

The podcast highlights the 20th anniversary of HelpSpot, a help desk software developed by Ian. He reflects on the journey of running an internet business over two decades, the evolution of SaaS (Software as a Service), and how HelpSpot has maintained a loyal customer base over the years. Ian acknowledges the importance of good customer service and nurturing relationships with clients as essential for longevity in the software industry.

Aaron's Success on Twitter

Aaron discusses his unexpected success on Twitter, revealing that a series of tweets gained significant attention, leading to thousands of impressions and interactions. He reflects on the nature of social media engagement, the randomness of virality, and how his tweets, while seemingly unrelated to his main business, have opened doors for increased visibility and potential business opportunities.

Database School Progress

Towards the end of the episode, Aaron shares updates on his Database School project, where he is transitioning to a subscription model. The early results show promising traction with subscribers already signing up for annual recurring revenue. Aaron emphasizes the importance of the gradual build-up of content and the potential to continue monetizing through this model, expressing excitement about the lessons learned along the way.

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