Our B2B SaaS Journey

SixSides
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Join the SixSides.co team as we navigate the highs and lows of building a B2B SaaS company. From finding product-market fit to scaling sales and community-driven growth, we share real insights, tough lessons, and candid conversations about what it really takes to grow a successful SaaS business. Whether you're a founder, marketer, developer, or just SaaS-curious, this is your backstage pass to the journey.

  1. 5d ago

    79: Cancel all my meetings

    In this episode, Mitchell and Gavin submit the first Police Games app release ahead of a 6,000-person rollout, unpack SixSides’ pivot from event managers to community-led organisations, and share how AI-assisted development, a tough client decision, and a new AEO strategy are shaping the next phase of the business. Chapters (00:00) - Moving out of the office and working from home (08:14) - The Police Games app is submitted (13:39) - Automated testing and the launch timeline (20:45) - New SixSides events and client updates (22:18) - The City of Gold Coast and solving the cold start problem (27:45) - Our ICP pivot and finding a blue ocean (32:53) - Sales-market fit and the 5.8 method (36:24) - Rebuilding DealBuddi with Laravel AI (45:30) - The difficult client decision (49:23) - AEO, HubSpot and getting ready to launch In this episode, we cover:Mitchell leaving his coworking office after five years and adjusting to working from home full-timeSubmitting the Police Games mobile app to Apple and Google ahead of a rollout to around 6,000 peopleThe final QA push across iOS, Android, API endpoints and app screensHow Claude Code and AI-assisted development dramatically accelerated the final stages of the releaseUsing Maestro for automated mobile app testing across real devicesPlanning the Police Games launch timeline, onboarding and communicationsRunning another SixSides event for Toll Women in Aviation and preparing for the Queensland Volunteering ConferenceGavin’s plan to build local network effects by concentrating communities around the Gold CoastApplying ideas from The Cold Start Problem and Blue Ocean Strategy to SixSidesPivoting the SixSides ideal client profile from event managers towards community managers and associationsRevisiting sales-market fit and Gavin’s 5-ate sales methodRebuilding DealBuddi onboarding with Laravel AI to make one-to-many workshops commercially viableMaking the difficult decision to end a client relationship after a successful pilot stopped feeling collaborativeAnswer engine optimisation, HubSpot and creating content designed to appear in AI-generated answersGetting the business infrastructure, product and marketing ready for the next phase of SixSides growthGot 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 SixSides: sixsides.coBook a call with Gavin: call.sixsides.coMitchell on Bluesky: mitchdav.isMitchell on LinkedIn: mitchdavGavin on LinkedIn: gavintyeGavin on YouTube: gavintye1SixSides on LinkedIn: sixsidesSixSides on X: sixsideseventsSixSides on Bluesky: sixsides.coSixSides on Youtube: sixsidescoSixSides on Substack: sixsidesSixSides on Skool: Community Builders Network

  2. Aug 24

    78: Rejection only makes us stronger

    In this episode, Mitchell and Gavin navigate an App Store rejection as the World Police Games launch gets very real, unpack a new Claude-powered development workflow that is dramatically increasing output, explore how MCP could connect the different sides of SixSides, and celebrate Gavin surviving his 100km bike ride. Chapters (00:00) - Gavin’s 100km ride (07:27) - Testing week and Apple rejects our app (13:35) - Racing towards the World Police Games launch (16:25) - The new SixSides marketing site (19:21) - HubSpot, Snitcher and our ICP workflow (22:37) - Why Mitch is moving from Cursor to Claude (29:19) - Connecting SixSides to Claude with MCP (33:16) - The real-world ROI of AI development (36:00) - Mitch is moving out of his office (38:31) - Wrapping up In this episode, we cover:Gavin completing his 100km bike ride from the Gold Coast to BrisbaneTesting week for the World Police Games app ahead of launchWhy Apple rejected the app while Google approved itPreparing an iOS and Android app for App Store reviewAdding account deletion and removing unused NFC and background audio permissionsPreparing SixSides for thousands of World Police Games attendeesThe remaining work around athlete CSV imports, HubSpot and welcome email automationProgress on the new SixSides marketing website and design workflow in Figma and SlackEarly signs that SixSides blog content is being indexed and found through GoogleUsing Snitcher and HubSpot to identify and follow up with ideal customer profilesWhy Mitchell is moving from Cursor towards Claude Code and SoloUsing MCP to connect AI agents with Cloudflare, AWS, Sentry and other business systemsCutting infrastructure costs from roughly $2,000 per month towards $300 with the help of AIBuilding an MCP integration so SixSides data can be accessed through Claude and ChatGPTUsing AI to connect product development, marketing, sales and operationsHow AI is changing the role and workflow of experienced software developersMitchell's decision to give up his office and return to working from homeGot 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 SixSides: sixsides.coBook a call with Gavin: call.sixsides.coMitchell on Bluesky: mitchdav.isMitchell on LinkedIn: mitchdavGavin on LinkedIn: gavintyeGavin on YouTube: gavintye1SixSides on LinkedIn: sixsidesSixSides on X: sixsideseventsSixSides on Bluesky: sixsides.coSixSides on Youtube: sixsidescoSixSides on Substack: sixsidesSixSides on Skool: Community Builders Network

  3. Aug 17

    77: From 64 Facebook groups to one app

    In this episode, Mitchell and Gavin celebrate a hugely positive WPFG demo, race to get the new app through Apple and Google review, unpack why SixSides’ customer-first culture is getting noticed, and wrestle with HubSpot pricing, a non-paying client, release automation, translations, and a new way of giving developers more ownership. Chapters (00:00) - Intro (02:29) - WPFG demo feedback (04:17) - The final stretch for WPFG phase one (11:31) - App Store assets and a new SixSides look (12:59) - Our culture is shining through (14:36) - Automating the release process (17:14) - The HubSpot pricing surprise (20:34) - A hard client decision (22:59) - Chat, translations and giving developers more ownership (30:44) - Landing page progress and Gavin’s massive ride In this episode, we cover:The overwhelmingly positive feedback from the latest WPFG app demoReplacing the need to manage 64 individual Facebook groups for sporting communitiesGetting the WPFG app through Apple App Store and Google Play reviewManaging TestFlight, external testers and beta feedback before launchThe final polish required before rolling the app out to thousands of athletesCreating better App Store and Play Store assets for WPFG and SixSidesWhy SixSides’ customer-first culture is becoming a competitive advantageUsing Claude to improve and automate the mobile app release processManaging multiple branded mobile apps from a single codebaseThe unexpected cost of HubSpot marketing contacts and whether the deal still makes senseWhat to do when a client keeps using your SaaS but stops communicating or payingPrototyping real-time chat and translation features for eventsUsing AWS translation APIs and exploring on-device language modelsGiving developers outcome-based projects instead of tightly scoped ticketsPreparing the development team to work independently while Mitchell is awayEarly progress on the redesigned SixSides landing pageGavin’s underprepared 70 km training ride ahead of a 100 km eventGot 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 SixSides: sixsides.coBook a call with Gavin: call.sixsides.coMitchell on Bluesky: mitchdav.isMitchell on LinkedIn: mitchdavGavin on LinkedIn: gavintyeGavin on YouTube: gavintye1SixSides on LinkedIn: sixsidesSixSides on X: sixsideseventsSixSides on Bluesky: sixsides.coSixSides on Youtube: sixsidescoSixSides on Substack: sixsidesSixSides on Skool: Community Builders Network

  4. Aug 10

    76: Upgrading HubSpot before our biggest launch yet

    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 launchHow referrals between event organisers are creating new sales opportunitiesTurning event attendees into future community builders and qualified leadsWhether SixSides should host its own community instead of relying on platforms like SkoolUsing white glove onboarding to improve the experience for new community organisersUpgrading HubSpot to manage a growing sales pipeline and thousands of new usersUsing Claude and MCP integrations to configure CRM workflowsThe opportunity to support organisations with communities of up to 70,000 volunteersWhy gated white papers and downloadable resources may be losing their valueMaking content publicly available for AEO, AI discovery and organic searchWaiting for a proven customer acquisition pipeline before spending money on advertisingMeasuring return on ad spend in a bootstrapped SaaS businessRedesigning the SixSides website ahead of the World Police Games app releaseCreating onboarding emails, product guides and launch communications for 5,000 usersSeparating official announcements from general community posts in the SixSides news feedDesigning private messaging, group chats and announcement channelsThe challenges of end-to-end encryption in community messaging productsTranslating user-generated content without compromising user privacyExploring on-device AI for private translations and live speech-to-textManaging founder stress, fitness routines and the decision to take a break from alcoholGot 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 SixSides: sixsides.coBook a call with Gavin: call.sixsides.coMitchell on Bluesky: mitchdav.isMitchell on LinkedIn: mitchdavGavin on LinkedIn: gavintyeGavin on YouTube: gavintye1SixSides on LinkedIn: sixsidesSixSides on X: sixsideseventsSixSides on Bluesky: sixsides.coSixSides on Youtube: sixsidescoSixSides on Substack: sixsidesSixSides on Skool: Community Builders Network

  5. Aug 4

    75: Can we handle 5,000 people at launch?

    In this episode, Mitchell and Gavin check in on fitness and their delivery timeline, share updates on WPFG and the latest SixSides design work with Robin Holesinsky, celebrate two new clients, and map out the next 6 to 12 months while trying to spend more time working on the business rather than only in it. Links Robin HolesinskyChapters (00:09) - Intro and Mitchell’s Laracon speaker video (02:16) - Fitness updates, leg presses and very long walks (10:44) - WPFG app timeline, polish and testing (14:52) - Preparing to onboard more than 5,000 participants (22:56) - Design update with Robin Holesinsky (27:22) - Podcast plans during Mitchell’s honeymoon (30:11) - Two new clients and more deals close to signing (34:11) - Planning the next 6 to 12 months and exploring HubSpot (39:04) - Using AI and MCP while working on the business (42:28) - Outro and listener feedback In this episode, we cover:Preparing the SixSides mobile app for its first major WPFG releaseWhy the app needed another round of polish after 12 weeks of developmentReframing the product from an event management tool to a community communication platformTesting the mobile app with TestFlight, Google Play and MaestroPreparing SixSides to onboard more than 5,000 WPFG participantsUsing serverless infrastructure, automatic database scaling and caching to manage launch trafficStaggering user invitations to reduce risk during a large app rolloutPlanning customer onboarding, support and engagement with Intercom and BentoHiring Robin Holesinsky to redesign the SixSides marketing websiteManaging a tight launch timeline before Mitchell leaves for his honeymoonKeeping the podcast running while Mitchell is travelling through EuropeSigning two new clients and building the SixSides sales pipelinePlanning the next 6 to 12 months of the businessConsidering HubSpot for sales and customer relationship managementUsing AI and MCP tools to improve internal workflowsMaking more time to work on the business rather than only delivering client workFounder fitness updates, including gym progress, cycling and long-distance walkingGot 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 SixSides: sixsides.coBook a call with Gavin: call.sixsides.coMitchell on Bluesky: mitchdav.isMitchell on LinkedIn: mitchdavGavin on LinkedIn: gavintyeGavin on YouTube: gavintye1SixSides on LinkedIn: sixsidesSixSides on X: sixsideseventsSixSides on Bluesky: sixsides.coSixSides on Youtube: sixsidescoSixSides on Substack: sixsidesSixSides on Skool: Community Builders Network

  6. Jul 27

    74: Six inches high and rising

    In this episode, Mitchell and Gavin unpack a catastrophic house flood, celebrate the launch of Changemakers and 10,000 LinkedIn followers, simplify SixSides’ lead generation strategy, and race through community features, GDPR compliance, device testing and onboarding with one week of development left. Links Changemakers podcastChapters (00:00) - Intro and Gavin’s flooded house (06:24) - Changemakers is finally live (10:05) - Finding a LinkedIn voice and reaching 10,000 followers (16:12) - The A-hole title delivers, and lead generation gets simplified (22:21) - Repurposing whitepapers with AI (30:49) - Community features and GDPR compliance (36:16) - Maestro testing and one week of development left (43:10) - Building a bespoke Police Games integration (50:20) - Onboarding webinars and the marketing design decision (56:52) - The Brimstone Brawl and outro In this episode, we cover:Gavin’s disastrous weekend after five open taps flooded his house with six inches of waterLaunching the first episode of Changemakers with Nick Marchese from Orange SkyRepurposing podcast interviews into LinkedIn carousels, blog posts, quotes and future long-form contentFinding an authentic LinkedIn voice while building a B2B SaaS in publicThe five years of consistent effort behind Gavin crossing 10,000 LinkedIn followersWhy LinkedIn comments can create valuable B2B conversations even when most receive no responseSimplifying SixSides’ lead generation after cold email failed to produce resultsCreating clearer content workflows for a remote marketing and sales teamTurning bespoke whitepapers and strategic briefs into reusable sales and marketing assetsUsing AI to personalise whitepapers and potentially help prospects build internal business casesBuilding community posts, comments, reactions, member lists and management tools into SixSidesSupporting GDPR account deletion without damaging historical event attendance analyticsTesting a mobile app across multiple iPhone and Android devices with MaestroPreparing the Police Games app for testing, App Store review and launchKeeping bespoke Police Games logic outside the core SixSides codebase with a Cloudflare WorkerUsing registration data to automatically add athletes to the correct events and communitiesPlanning in-app onboarding and live webinars for international sporting associationsWeighing a three-month design retainer against cash flow, workload and potential return on investmentThe Brimstone Brawl, where people in medieval armour hit each other with swords and axesGot 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 SixSides: sixsides.coBook a call with Gavin: call.sixsides.coMitchell on Bluesky: mitchdav.isMitchell on LinkedIn: mitchdavGavin on LinkedIn: gavintyeGavin on YouTube: gavintye1SixSides on LinkedIn: sixsidesSixSides on X: sixsideseventsSixSides on Bluesky: sixsides.coSixSides on Youtube: sixsidescoSixSides on Substack: sixsidesSixSides on Skool: Community Builders Network

  7. Jul 20

    73: What do you say we cut the chit chat, a-hole?

    In this episode, Mitchell and Gavin unpack a reassuring World Police Games client catch-up, turn LinkedIn into a competitive sport, prepare the Changemakers podcast for launch, and push SixSides towards release with a redesigned app, new analytics and support tooling, community features, and a long-overdue plan to reduce their bus factor. Links What do you say we cut the chit chat, a-hole?Chapters (00:00) - A World Cup lesson for bootstrappers (04:14) - Proactively updating the Police Games team (08:14) - Chasing sporting events and parkrun connections (10:48) - The LinkedIn impressions showdown (15:49) - Launching the Changemakers podcast (21:12) - Hiring a designer for the SixSides marketing site (29:45) - PostHog, Intercom and the finished app redesign (35:06) - Two weeks to finish the World Police Games milestone (40:07) - The bus factor problem (43:18) - Communities, expansion revenue and launch planning In this episode, we cover:Proactively keeping major event clients informed during long development projectsThe latest progress on the World Police Games appExpanding SixSides into sporting events and volunteering organisationsBuilding relationships with the founder of parkrun AustraliaMitchell and Gavin’s LinkedIn impressions competitionWhat makes personal founder-led LinkedIn content performPreparing the new Changemakers podcast for launchEditing podcast intros, music and production workflowsBudgeting for a professional SixSides marketing website redesignFinding SaaS designers through DribbbleIntegrating PostHog analytics into the mobile app and web dashboardAdding Intercom customer support and push notificationsCompleting the SixSides mobile app redesign and translation systemAutomated mobile app testing with MaestroGDPR, account deletion and attendee privacyReducing the bus factor inside a bootstrapped SaaSGiving contractors enough access to keep the business runningBuilding community posts, comments, likes and invitations in SixSidesExpansion revenue from existing customersPlanning a coordinated launch campaign for the new SixSides websiteGot 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 SixSides: sixsides.coBook a call with Gavin: call.sixsides.coMitchell on Bluesky: mitchdav.isMitchell on LinkedIn: mitchdavGavin on LinkedIn: gavintyeGavin on YouTube: gavintye1SixSides on LinkedIn: sixsidesSixSides on X: sixsideseventsSixSides on Bluesky: sixsides.coSixSides on Youtube: sixsidescoSixSides on Substack: sixsidesSixSides on Skool: Community Builders Network

  8. Jul 13

    72: We put a database in your backyard

    In this episode, Mitchell and Gavin make a $500 LinkedIn bet, share the infrastructure mistake that was slowing down every screen in SixSides, and unpack their plans to support global events, launch community features, and pursue an opportunity that could transform the business. Links Problem-Led Growth for B2B GTM on SkoolChapters (00:00) - Wedding rings, swearing and podcast downloads (03:49) - Fitness updates and the 100-kilometre ride (08:35) - LinkedIn posting and the $500 impressions bet (15:39) - Listener shoutouts and sending Nick his dice (19:31) - Gavin’s first community leader interview (22:08) - Too much work and growing DealBuddi (24:26) - Building global infrastructure for SixSides (38:31) - Android is complete and communities are next (41:44) - Taking SixSides worldwide (49:42) - Startup World Cup, Snitcher and the marketing website In this episode, we cover:Building consistent fitness habits while running a bootstrapped SaaSMitchell’s return to LinkedIn and the wedding post that nearly floppedGavin’s 13,000-impression LinkedIn postThe $500 LinkedIn competition running until the end of the financial yearListener shoutouts for Ryan David, Varun Jain and Nick TaylorGavin’s first community leadership interview with Orange Sky founder Nic MarchesiGrowing DealBuddi while continuing to fund SixSidesPreparing SixSides for the World Police and Fire Games launchMigrating the SixSides database from MySQL to PostgreSQLMoving from PlanetScale back to AWS AuroraDeploying infrastructure across Sydney, Germany, Singapore and North VirginiaUsing synthetic canaries to test API performance around the worldFinding the unnecessary WorkOS request that was slowing down every screenReducing global API response times to under 500 millisecondsCompleting the Android redesign and supporting older iOS versionsBeginning development of SixSides community featuresPiloting SixSides with the Global Entrepreneurship Network in AustraliaUsing a local-first strategy to grow a global event networkWhy ProcurePro was the deserving Startup World Cup winnerReviewing Snitcher traffic and the need for a stronger SixSides marketing websiteDeciding whether to hire an external website designerUsing ChatGPT voice mode during longer fitness walksGot 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 SixSides: sixsides.coBook a call with Gavin: call.sixsides.coMitchell on Bluesky: mitchdav.isMitchell on LinkedIn: mitchdavGavin on LinkedIn: gavintyeGavin on YouTube: gavintye1SixSides on LinkedIn: sixsidesSixSides on X: sixsideseventsSixSides on Bluesky: sixsides.coSixSides on Youtube: sixsidescoSixSides on Substack: sixsidesSixSides on Skool: Community Builders Network

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About

Join the SixSides.co team as we navigate the highs and lows of building a B2B SaaS company. From finding product-market fit to scaling sales and community-driven growth, we share real insights, tough lessons, and candid conversations about what it really takes to grow a successful SaaS business. Whether you're a founder, marketer, developer, or just SaaS-curious, this is your backstage pass to the journey.

Information

  • Creator
    SixSides
  • Years Active
    2025 - 2026
  • Episodes
    79
  • Rating
    Explicit
  • Copyright
    © 2025 SixSides
  • Show Website
    Our B2B SaaS Journey

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