Our B2B SaaS Journey

SixSides

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. 2d ago

    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

  2. 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

  3. 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

  4. 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

  5. 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

  6. Jul 6

    71: You can just shoot the messenger

    In this episode, Mitchell and Gavin deal with possums, fitness resets, a brutal sales call, one of their worst days building SixSides so far, and the product push to get the World Police and Fire Games app ready for testing in just four weeks. Links Problem-Led Growth for B2B GTM on SkoolChapters (00:00) - Explicit warning from Editor Mitch (00:31) - Possums, alarms, and nude home defence (05:20) - Socceroos, bike rides, and getting back into fitness (08:46) - Mitchell restarts the 75 challenge (18:27) - Shoot the messenger (24:59) - Europe, Brisbane, Laracon AU, and travel plans (33:26) - One of our worst days building SixSides (41:46) - World Police and Fire Games app progress (51:12) - LinkedIn results and marketing experiments (58:18) - Onboarding session and what still needs work In this episode, we cover:Why this episode earned an explicit rating before it even startedGavin’s 2am possum alarm scare and the noble art of nude home defenceMitchell watching the Socceroos and Gavin’s take on Australian footballRestarting a 75 Hard-style fitness challenge after slipping out of routineThe link between exercise, stress, mental health, and founder energyA sales meeting that made SixSides feel like a “side hustle”Why blunt feedback can be useful, even when it lands badlyThe value of not shooting the messenger and digging into the real messageBooking Europe, Brisbane, Laracon AU, and a very packed few months of travelOne of the toughest founder conversations Mitchell and Gavin have had so farRegaining confidence by merging unfinished product work back into the main appPreparing the World Police and Fire Games app for testing in four weeksTranslating the SixSides app UI into multiple languagesBuilding splash screens, map views, calendar views, and better event visualsUsing ChatGPT to help turn event schedules into Laravel seedersPlanning venue maps, transport links, and event discovery inside the appPostgres migration work and Android progressLinkedIn content experiments and what performed better this monthGavin’s upcoming Orange Sky interview for the SixSides marketing planReviewing the customer onboarding flow and realising SixSides is still at level zeroGot 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. Jun 29

    70: Let's take this offline

    In this episode, Mitchell and Gavin talk through the final stretch before World Police and Fire Games testing, the Postgres and S3 work behind SixSides’ offline sync plans, an app store trademark dispute, and Gavin’s rapidly evolving community-led marketing campaign that might now include a new YouTube strategy. Chapters (00:00) - Intro and bird complaints (02:27) - Pool losses, Socceroos, and pub plans (07:07) - Postgres, S3, and offline mode (13:35) - Podcast reviews, downloads, and app redesign progress (17:39) - The app store trademark dispute (24:14) - Gavin’s community-led marketing campaign (27:20) - Should SixSides create a YouTube channel? (35:14) - The new LinkedIn strategy and Community Builders Network (40:06) - Testing advertising on GPT (43:57) - The year so far and what comes next In this episode, we cover:The Socceroos, pub lunches, and the perks of running your own businessWhy SixSides is migrating from MySQL to PostgresHow ElectricSQL could unlock offline mode and real-time sync for event appsMoving request logs from the database to Amazon S3Using Amazon Athena to query log files stored in S3Hitting 2,000 podcast downloads and five-star Spotify reviewsThe ongoing SixSides app redesign and the push toward a more polished event appThe five-week countdown to World Police and Fire Games testingAn app store trademark dispute and why it has been frustratingGavin’s new community-led marketing campaignPlanning guest interviews with community leaders and charitiesWhether SixSides should create a more intentional YouTube channelA new LinkedIn strategy focused on community stories instead of product promotionThe early days of the Community Builders Network on SkoolTesting advertising opportunities through GPTWhy the SixSides website and freemium funnel need to improve before paid ads make senseOverselling the vision, then racing to make the product catch upGot 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. Jun 22

    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 FundraiserOpen Source iPhone Chatbot from KiraaChapters (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 plansThe new SixSides marketing plan built around interviewing community leaders and turning those conversations into useful contentWhy SixSides may need to think more like a media company to build trust and create a sustainable pipelineThe road to $1.5m, including founder-led sales, team-enabled sales, product-led growth, and better onboardingWhy customer onboarding is becoming one of the most immediate bottlenecks for SixSidesPreparing for the World Police Games and a potentially much bigger “Mr Worldwide” opportunityThe app redesign, including handing more design implementation work over to the teamHow Mitchell is improving team workflows in Linear with clearer comments, screenshots, and before-and-after updatesGavin’s sales mistake with a potential charity client, and why founders need to be careful when sharing unqualified pricing materialThe “fat guy, skinny guy” sales framework for anchoring value by showing the before and afterWhy missing out on the Startup World Cup might be a useful reminder to focus on customers instead of grants and competitionsGavin signing up for a 100km Brisbane to Gold Coast bike ride for cancer fundraisingMitchell saying no to extra commitments and narrowing his focusMoving the SixSides database from MySQL to Postgres to support ElectricSQL and offline mode in the mobile appWhy offline app support matters for event attendees, especially international participants without reliable mobile dataTinyBase, Cloudflare Durable Objects, and why the team is now leaning towards Postgres and ElectricSQLLocal AI models, Apple’s on-device AI direction, and possible future use cases for translations inside the SixSides appGot 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
    76
  • Rating
    Explicit
  • Copyright
    © 2025 SixSides
  • Show Website
    Our B2B SaaS Journey

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