69: How we are multitasking while bootstrapping our SaaS startup

69: How we are multitasking while bootstrapping our SaaS startup

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 * Gavin's Brisbane to Gold Coast Fundraiser [https://fundraise.mater.org.au/fundraisers/gavintye/brisbane-to-gold-coast-2026] * Open Source iPhone Chatbot from Kiraa [https://www.youtube.com/watch?v=OtLL0SO36LI] 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 [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 * SixSides: sixsides.co [https://www.sixsides.co/] * Book a call with Gavin: call.sixsides.co [https://call.sixsides.co/gavin] * Mitchell on Bluesky: mitchdav.is [https://bsky.app/profile/mitchdav.is] * Mitchell on LinkedIn: mitchdav [https://www.linkedin.com/in/mitchdav/] * Gavin on LinkedIn: gavintye [https://www.linkedin.com/in/gavintye/] * Gavin on YouTube: gavintye1 [https://www.youtube.com/@GavinTye1] * SixSides on LinkedIn: sixsides [https://www.linkedin.com/company/sixsidesevents/] * SixSides on X: sixsidesevents [https://x.com/SixSidesEvents] * SixSides on Bluesky: sixsides.co [https://bsky.app/profile/sixsides.co] * SixSides on Youtube: sixsidesco [https://www.youtube.com/channel/UC2l1wOk07BWCJo7U1ym3gsw] * SixSides on Substack: sixsides [https://sixsides.substack.com/] * SixSides on Skool: Community Builders Network [https://www.skool.com/community-builders-network-2197]

68: AI is making us dumber

In this episode, Mitchell and Gavin deal with their first proper hater, reset their routines after a messy few weeks, unpack a six month marketing project for SixSides, and get into a surprisingly tense debate about whether AI is helping us work smarter or quietly making us lazier. Links * Community Builders Network on Skool [https://www.skool.com/community-builders-network-2197] Chapters * (00:00) - Intro x2 * (01:33) - Meeting the first hater * (03:56) - New habits die easy * (08:01) - Fitness goals, walking, and pickleball * (13:48) - Juggling multiple balls across SixSides and DealBuddi * (17:46) - Planning a six month marketing project * (20:39) - Research projects for the engineering team * (23:37) - Redesigning the SixSides mobile app * (35:13) - World Police and Fire Games delivery timeline * (37:52) - AI is making us dumber In this episode, we cover: * Handling negative feedback from someone who does not believe in the SixSides vision * Why the opportunity might be in the cracks that other people miss * How moving house disrupted Gavin’s routines, habits, gym schedule, and focus * Why new habits die easy, especially when your environment changes * Mitch’s post-wedding fitness motivation struggles and the search for a new goal * Pickleball, long walks, and finding achievable physical challenges * Gavin juggling SixSides, DealBuddi, family revenue, house setup, sales, and lead generation * The pressure of managing a team, delivering for the World Police and Fire Games, chasing customers, and exploring funding * Planning a six month marketing project around community fundraising ideas * Using research, interviews, webinars, podcasts, blog posts, LinkedIn content, and white papers as one connected marketing engine * The SixSides community being set up on Skool * Research projects for the engineering team across ticketing, event websites, and event registration * Why the team paused coding for a week to research the market before building * The new SixSides mobile app design, including native iOS patterns and liquid glass * Reducing event organiser customisation so the app feels more cohesive * Designing communities, events, explore flows, and future app navigation * Preparing for the World Police and Fire Games timeline and internal testing window * Offline mode research and why it may require a major rethink of the mobile app data layer * Whether AI-generated research, code comments, LinkedIn posts, and internal communication can be trusted * The difference between AI-generated work and AI-assisted thinking * Why founders still need to slow down, think clearly, and care about quality Got questions or topics you want us to cover? Email us at journey@sixsides.co [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 * SixSides: sixsides.co [https://www.sixsides.co/] * Book a call with Gavin: call.sixsides.co [https://call.sixsides.co/gavin] * Mitchell on Bluesky: mitchdav.is [https://bsky.app/profile/mitchdav.is] * Mitchell on LinkedIn: mitchdav [https://www.linkedin.com/in/mitchdav/] * Gavin on LinkedIn: gavintye [https://www.linkedin.com/in/gavintye/] * Gavin on YouTube: gavintye1 [https://www.youtube.com/@GavinTye1] * SixSides on LinkedIn: sixsides [https://www.linkedin.com/company/sixsidesevents/] * SixSides on X: sixsidesevents [https://x.com/SixSidesEvents] * SixSides on Bluesky: sixsides.co [https://bsky.app/profile/sixsides.co] * SixSides on Youtube: sixsidesco [https://www.youtube.com/channel/UC2l1wOk07BWCJo7U1ym3gsw] * SixSides on Substack: sixsides [https://sixsides.substack.com/]

67: Stop selling the future

In this episode, Mitchell and Gavin rethink how they are selling SixSides, map out what it could take to grow towards $1.5m ARR, unpack the pressure of supporting the World Police Games, and talk through burnout, admin days, AI-assisted onboarding, multilingual apps, LinkedIn experiments, and whether video should become a bigger part of their marketing. Links * Laracon AU [https://laracon.au/talks/the-lazy-product-manifesto] Chapters * (00:00) - Intro, stretching, lawns, and episode 67 * (06:31) - Selling what SixSides can do today * (13:32) - Planning the path to $1.5m ARR * (17:28) - Onboarding, AI agents, and AI redundancy * (22:49) - Mitchell is speaking at Laracon AU * (25:48) - Wednesday admin and avoiding burnout * (35:09) - New mobile app design and Liquid Glass * (38:36) - The World Police Games gets very real * (42:31) - Should SixSides start making videos? * (46:42) - LinkedIn, lead gen, Skool, translations, and team updates In this episode, we cover: * Why Gavin realised SixSides needs to sell what it can do today, not just the community-led platform it is becoming * How flagship events could become the wedge into broader community and account growth * The challenge of building towards $1.5m ARR without breaking onboarding, support, or customer experience * Why the World Police Games could create a major product-led growth opportunity for SixSides * Whether an AI onboarding agent could help customers set up events faster * Why SixSides is an AI-assisted business, not an AI-reliant business * Mitchell’s upcoming Laracon AU talk about reducing friction in software with AI * Mitchell’s new “Wednesday admin” experiment to reduce stress and protect focus time * The risk of burnout while juggling SixSides, other businesses, product work, sales, and the World Police Games * The new SixSides mobile app design, including Apple’s Liquid Glass UI direction * Watching the World Police Games TV commercial and realising how big the project is becoming * Whether SixSides should use YouTube and video content as a marketing channel * LinkedIn results, AI-generated posts, and shifting back towards more genuine founder-led content * Building a community for event organisers using Skool * Translating the SixSides app into Spanish, French, simplified Chinese, German, and Portuguese * Weekly CEO and CTO updates to keep the growing team aligned Got questions or topics you want us to cover? Email us at journey@sixsides.co [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 * SixSides: sixsides.co [https://www.sixsides.co/] * Book a call with Gavin: call.sixsides.co [https://call.sixsides.co/gavin] * Mitchell on Bluesky: mitchdav.is [https://bsky.app/profile/mitchdav.is] * Mitchell on LinkedIn: mitchdav [https://www.linkedin.com/in/mitchdav/] * Gavin on LinkedIn: gavintye [https://www.linkedin.com/in/gavintye/] * Gavin on YouTube: gavintye1 [https://www.youtube.com/@GavinTye1] * SixSides on LinkedIn: sixsides [https://www.linkedin.com/company/sixsidesevents/] * SixSides on X: sixsidesevents [https://x.com/SixSidesEvents] * SixSides on Bluesky: sixsides.co [https://bsky.app/profile/sixsides.co] * SixSides on Youtube: sixsidesco [https://www.youtube.com/channel/UC2l1wOk07BWCJo7U1ym3gsw] * SixSides on Substack: sixsides [https://sixsides.substack.com/]

66: Mitchell is becoming a real CTO

In this episode, Mitchell and Gavin unpack a much better workflow for managing the SixSides development team in Linear, clarify their event-led positioning and pricing strategy, share early wins from voting at recent events, and discuss app onboarding, nested communities, AIME 2027 and a simpler approach to theme customisation. Links * FeedSpot - B2B SaaS podcasts [https://podcast.feedspot.com/b2b_saas_podcasts/] * Linear [https://linear.app/] * Clarityflow [https://clarityflow.com/] * Builder Methods [https://buildermethods.com/] Chapters * (00:00) - Gavin’s new house, FeedSpot and a fitness update * (04:43) - Managing the SixSides dev team with Linear * (12:18) - Projects, statuses and weekly development updates * (22:30) - Mobile onboarding and nested communities * (25:42) - Positioning SixSides and rethinking the pricing page * (36:12) - Planning for AIME 2027 and building a community * (41:53) - Voting feedback from MArinas and StartClub BNE * (48:04) - Reducing theme customisation for a better app design * (51:27) - Where to find Mitchell and Gavin online In this episode, we cover: * Gavin’s move into a new home and office, and Mitchell’s fitness accountability update * SixSides being recognised by FeedSpot as a top B2B SaaS podcast * Managing an offshore software development team with better processes in Linear * Engineering office hours, ticket shaping, project statuses and review pipelines * Using weekly development updates to improve accountability and team communication * Building the World Police and Fire Games app on the existing SixSides codebase * Improving mobile app onboarding before asking attendees to register or sign in * Supporting nested communities for countries, sports and other groups within major events * Positioning SixSides as a community-led events platform * Why high-value B2B software pricing often needs a sales conversation instead of a public calculator * Using an internal pricing calculator to support quoting and future business case creation * Preparing for AIME 2027 and building an event organiser community before the conference * Feedback from MArinas and StartClub BNE after launching in-app voting * Using pre-event onboarding and email sequences to improve attendee engagement * Reducing theme customisation so the SixSides mobile app can feel more polished and consistent Got questions or topics you want us to cover? Email us at journey@sixsides.co [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 * SixSides: sixsides.co [https://www.sixsides.co/] * Book a call with Gavin: call.sixsides.co [https://call.sixsides.co/gavin] * Mitchell on Bluesky: mitchdav.is [https://bsky.app/profile/mitchdav.is] * Mitchell on LinkedIn: mitchdav [https://www.linkedin.com/in/mitchdav/] * Gavin on LinkedIn: gavintye [https://www.linkedin.com/in/gavintye/] * Gavin on YouTube: gavintye1 [https://www.youtube.com/@GavinTye1] * SixSides on LinkedIn: sixsides [https://www.linkedin.com/company/sixsidesevents/] * SixSides on X: sixsidesevents [https://x.com/SixSidesEvents] * SixSides on Bluesky: sixsides.co [https://bsky.app/profile/sixsides.co] * SixSides on Youtube: sixsidesco [https://www.youtube.com/channel/UC2l1wOk07BWCJo7U1ym3gsw] * SixSides on Substack: sixsides [https://sixsides.substack.com/]

65: We will crack a few eggs

In this episode, Mitchell and Gavin get ready for the Marinas event, unpack a very busy week of sales meetings, rethink their LinkedIn strategy, and work through the product, marketing, and sales roadmap leading into the World Police and Fire Games launch window in August. Links * Mobbin [https://mobbin.com] * UI.sh [https://ui.sh] * The 4 Levels of SaaS Landing Page UI Design [https://www.youtube.com/watch?v=eMMiLeo_UGI] Chapters * (00:00) - Intro * (01:05) - Fitness, accountability, and morning routines * (03:29) - Marinas is almost live * (08:10) - Event support and customer service expectations * (13:01) - Nine meetings in one week * (13:59) - Using DealBuddi and Gamma for proposals * (20:13) - Rethinking the LinkedIn strategy * (29:21) - Building a sales dashboard * (34:05) - Cold outreach and new sales channels * (37:40) - Mitch stole Gavin’s big idea * (40:41) - Everything changes in August * (44:34) - Rebuilding the marketing website * (46:57) - Turning changelogs into feature and use case pages * (53:00) - Scheduled notifications, voting, and dev updates In this episode, we cover: * Mitchell’s attempt to get back into fitness, and Gavin’s suspiciously productive morning routine * The upcoming Marinas event, and what it has taught us about onboarding larger events * Why hands-on customer support still matters when you are bootstrapping a SaaS * Gavin’s nine sales meetings in one week, and what that says about the new lead generation motion * Using DealBuddi and Gamma to quickly produce a professional proposal * The difference between strategic white papers and lighter proposal decks * What we are learning from LinkedIn content, and why the strategy is changing * Moving SixSides-focused posts to the company page * Building personal founder audiences through build in public posts * Creating a sales dashboard to track effort, pipeline, and revenue * The cost and strategy behind thoughtful cold outreach * Mitch accidentally rediscovering Gavin’s Canva integration idea * The August roadmap for the World Police and Fire Games * Preparing the SixSides marketing website for a potential spike in attention * Turning changelog entries into feature pages, use case pages, and industry pages * Using AI tools to improve product marketing and website design * Shipping scheduled notifications and live voting for events * Why August could become a major turning point for SixSides Got questions or topics you want us to cover? Email us at journey@sixsides.co [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 * SixSides: sixsides.co [https://www.sixsides.co/] * Book a call with Gavin: call.sixsides.co [https://call.sixsides.co/gavin] * Mitchell on Bluesky: mitchdav.is [https://bsky.app/profile/mitchdav.is] * Mitchell on LinkedIn: mitchdav [https://www.linkedin.com/in/mitchdav/] * Gavin on LinkedIn: gavintye [https://www.linkedin.com/in/gavintye/] * Gavin on YouTube: gavintye1 [https://www.youtube.com/@GavinTye1] * SixSides on LinkedIn: sixsides [https://www.linkedin.com/company/sixsidesevents/] * SixSides on X: sixsidesevents [https://x.com/SixSidesEvents] * SixSides on Bluesky: sixsides.co [https://bsky.app/profile/sixsides.co] * SixSides on Youtube: sixsidesco [https://www.youtube.com/channel/UC2l1wOk07BWCJo7U1ym3gsw] * SixSides on Substack: sixsides [https://sixsides.substack.com/]