36: The day we lost $97K
Nov 04, 2025
In this episode, Mitchell and Gavin talk through their best month yet in podcast downloads, Gavin’s rapid expansion into multiple podcasts, and the final lead-up to the Volunteering WA event — including Mitch’s mad dash to polish features and release a build in time. They also reflect on a tough week of stress, miscommunication, and their first big disagreement as co-founders, and how they worked through it. Plus, there’s a deep dive into why traditional digital lead generation is losing effectiveness — and how in-person events might be the comeback story.
Links
Links
- Subscribe to the newsletter: sixsides.substack.com
Chapters
In this episode, we cover:
- (00:00) - Intro
- (00:43) - The Leap podcast launch
- (03:41) - Podcast download growth
- (05:59) - Volunteering WA prep
- (07:26) - Juggling three major events this week
- (09:46) - Last-minute app tweaks and release plans
- (11:09) - Recap video design decisions
- (13:06) - Photo timing, music, and recap video UX
- (16:05) - Video formats for social media
- (17:12) - Gavin’s on-the-ground plan for interviews in Perth
- (19:01) - Hope for a smooth event rollout
- (20:35) - The DocuSign debate
- (22:29) - Business case writing for WorldShare
- (25:08) - Streamlining the process with Fireflies
- (26:06) - Sales learnings from recent calls
- (28:52) - We didn’t get the grant
- (31:16) - In-person lead gen is making a comeback
- (33:37) - The case for businesses building community
- (34:58) - SixSides vs online event platforms
- (36:31) - Making content AI searchable
- (38:06) - DealBuddi and LLM-ready SEO
- (39:16) - Mitch and Gavin’s falling out (and how they resolved it)
- (47:07) - Next week’s in-person catch-up in Brisbane
- (48:09) - Recording plans for next week’s episode
- (50:07) - Laracon AU volunteering and wrap-up
In this episode, we cover:
- Celebrating the show’s best-ever month for downloads
- Gavin’s new podcast series, The Leap, and upcoming guests
- Preparing for Volunteering WA, Founders Collective, and WorldShare’s Cambodia event
- Recap video functionality and design tweaks before release
- Shifting lead generation from digital back to in-person
- Building a business case for WorldShare and how it became a new playbook
- Honing the SixSides value prop in real sales conversations
- Reflecting on not getting the Ignite Ideas Grant
- The emotional toll of juggling multiple businesses and responsibilities
- How Mitch and Gavin handled their first real co-founder conflict
- Behind the scenes of Gavin’s push for video interviews and content strategy
- Why AI-written cold emails are losing their edge
- SEO vs LLM optimisation and what they’re doing for visibility
- Using SixSides as a live case study at Volunteering WA
- The vision for helping regular businesses run community events
- What’s next for the product roadmap post-event season
Expect a candid, behind-the-scenes look at what it really takes to launch a B2B SaaS company from scratch – completely bootstrapped.
Got questions or topics you want us to cover? Email us at journey@sixsides.co
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