SixSides
76: Upgrading HubSpot before our biggest launch yet

76: Upgrading HubSpot before our biggest launch yet

August 11, 2026

In this episode, Mitchell and Gavin race towards the first World Police Games app handover, onboard two new clients, upgrade HubSpot for future growth, and debate gated content, paid advertising, encrypted chat, translations, and the next phase of SixSides.

Chapters

  • (00:00) - Intro and a very busy week
  • (04:20) - Onboarding two new clients
  • (07:13) - Community growth and the HubSpot upgrade
  • (16:25) - Is gated content dead?
  • (23:04) - When should SixSides start advertising?
  • (26:39) - The SixSides redesign and launch deadline
  • (32:55) - News feeds, official posts and the first milestone
  • (38:43) - Encrypted chat and group messaging
  • (41:43) - Translation, on-device AI and speech-to-text
  • (45:57) - Fitness, stress and going sober

In this episode, we cover:

  • Onboarding two new SixSides clients while preparing for a major product launch
  • How referrals between event organisers are creating new sales opportunities
  • Turning event attendees into future community builders and qualified leads
  • Whether SixSides should host its own community instead of relying on platforms like Skool
  • Using white glove onboarding to improve the experience for new community organisers
  • Upgrading HubSpot to manage a growing sales pipeline and thousands of new users
  • Using Claude and MCP integrations to configure CRM workflows
  • The opportunity to support organisations with communities of up to 70,000 volunteers
  • Why gated white papers and downloadable resources may be losing their value
  • Making content publicly available for AEO, AI discovery and organic search
  • Waiting for a proven customer acquisition pipeline before spending money on advertising
  • Measuring return on ad spend in a bootstrapped SaaS business
  • Redesigning the SixSides website ahead of the World Police Games app release
  • Creating onboarding emails, product guides and launch communications for 5,000 users
  • Separating official announcements from general community posts in the SixSides news feed
  • Designing private messaging, group chats and announcement channels
  • The challenges of end-to-end encryption in community messaging products
  • Translating user-generated content without compromising user privacy
  • Exploring on-device AI for private translations and live speech-to-text
  • Managing founder stress, fitness routines and the decision to take a break from alcohol

Got questions or topics you want us to cover? Email us at journey@sixsides.co

If you enjoyed this episode, please leave us a 5-star rating and a review on your favourite podcast app. It really helps us reach more people!

Connect with us