SixSides
69: How we are multitasking while bootstrapping our SaaS startup

69: How we are multitasking while bootstrapping our SaaS startup

June 23, 2026

In this episode, Mitchell and Gavin unpack the chaos of multitasking across SixSides, DealBuddi, sales, marketing, product, fitness, and life, while working through a new content strategy, a path to $1.5m, a painful sales lesson, a near-miss in the Startup World Cup, and a major technical move from MySQL to Postgres for offline event app support.

Links

Chapters

  • (00:00) - Intro and the multiple balls problem
  • (03:08) - Breaking priorities into action plans with ChatGPT
  • (03:56) - The new SixSides marketing plan
  • (10:24) - Mapping the road to $1.5m
  • (12:45) - Why onboarding is becoming a bottleneck
  • (17:47) - Mr Worldwide and the next big opportunity
  • (21:13) - App redesign and improving team workflows
  • (27:43) - Gavin’s painful sales mistake
  • (39:48) - Missing out on the Startup World Cup
  • (49:57) - Moving from MySQL to Postgres for offline mode

In this episode, we cover:

  • Gavin’s “multiple balls problem” and how he used walks and ChatGPT to break messy priorities into clearer action plans
  • The new SixSides marketing plan built around interviewing community leaders and turning those conversations into useful content
  • Why SixSides may need to think more like a media company to build trust and create a sustainable pipeline
  • The road to $1.5m, including founder-led sales, team-enabled sales, product-led growth, and better onboarding
  • Why customer onboarding is becoming one of the most immediate bottlenecks for SixSides
  • Preparing for the World Police Games and a potentially much bigger “Mr Worldwide” opportunity
  • The app redesign, including handing more design implementation work over to the team
  • How Mitchell is improving team workflows in Linear with clearer comments, screenshots, and before-and-after updates
  • Gavin’s sales mistake with a potential charity client, and why founders need to be careful when sharing unqualified pricing material
  • The “fat guy, skinny guy” sales framework for anchoring value by showing the before and after
  • Why missing out on the Startup World Cup might be a useful reminder to focus on customers instead of grants and competitions
  • Gavin signing up for a 100km Brisbane to Gold Coast bike ride for cancer fundraising
  • Mitchell saying no to extra commitments and narrowing his focus
  • Moving the SixSides database from MySQL to Postgres to support ElectricSQL and offline mode in the mobile app
  • Why offline app support matters for event attendees, especially international participants without reliable mobile data
  • TinyBase, Cloudflare Durable Objects, and why the team is now leaning towards Postgres and ElectricSQL
  • Local AI models, Apple’s on-device AI direction, and possible future use cases for translations inside the SixSides app

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

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