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

    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

    1h 2m

  2. Jun 15

    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 SkoolChapters (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 visionWhy the opportunity might be in the cracks that other people missHow moving house disrupted Gavin’s routines, habits, gym schedule, and focusWhy new habits die easy, especially when your environment changesMitch’s post-wedding fitness motivation struggles and the search for a new goalPickleball, long walks, and finding achievable physical challengesGavin juggling SixSides, DealBuddi, family revenue, house setup, sales, and lead generationThe pressure of managing a team, delivering for the World Police and Fire Games, chasing customers, and exploring fundingPlanning a six month marketing project around community fundraising ideasUsing research, interviews, webinars, podcasts, blog posts, LinkedIn content, and white papers as one connected marketing engineThe SixSides community being set up on SkoolResearch projects for the engineering team across ticketing, event websites, and event registrationWhy the team paused coding for a week to research the market before buildingThe new SixSides mobile app design, including native iOS patterns and liquid glassReducing event organiser customisation so the app feels more cohesiveDesigning communities, events, explore flows, and future app navigationPreparing for the World Police and Fire Games timeline and internal testing windowOffline mode research and why it may require a major rethink of the mobile app data layerWhether AI-generated research, code comments, LinkedIn posts, and internal communication can be trustedThe difference between AI-generated work and AI-assisted thinkingWhy founders still need to slow down, think clearly, and care about qualityGot 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: sixsides

    55 min

  3. Jun 9

    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 AUChapters (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 becomingHow flagship events could become the wedge into broader community and account growthThe challenge of building towards $1.5m ARR without breaking onboarding, support, or customer experienceWhy the World Police Games could create a major product-led growth opportunity for SixSidesWhether an AI onboarding agent could help customers set up events fasterWhy SixSides is an AI-assisted business, not an AI-reliant businessMitchell’s upcoming Laracon AU talk about reducing friction in software with AIMitchell’s new “Wednesday admin” experiment to reduce stress and protect focus timeThe risk of burnout while juggling SixSides, other businesses, product work, sales, and the World Police GamesThe new SixSides mobile app design, including Apple’s Liquid Glass UI directionWatching the World Police Games TV commercial and realising how big the project is becomingWhether SixSides should use YouTube and video content as a marketing channelLinkedIn results, AI-generated posts, and shifting back towards more genuine founder-led contentBuilding a community for event organisers using SkoolTranslating the SixSides app into Spanish, French, simplified Chinese, German, and PortugueseWeekly CEO and CTO updates to keep the growing team alignedGot 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: sixsides

    1h 6m

  4. Jun 1

    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 podcastsLinearClarityflowBuilder MethodsChapters (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 updateSixSides being recognised by FeedSpot as a top B2B SaaS podcastManaging an offshore software development team with better processes in LinearEngineering office hours, ticket shaping, project statuses and review pipelinesUsing weekly development updates to improve accountability and team communicationBuilding the World Police and Fire Games app on the existing SixSides codebaseImproving mobile app onboarding before asking attendees to register or sign inSupporting nested communities for countries, sports and other groups within major eventsPositioning SixSides as a community-led events platformWhy high-value B2B software pricing often needs a sales conversation instead of a public calculatorUsing an internal pricing calculator to support quoting and future business case creationPreparing for AIME 2027 and building an event organiser community before the conferenceFeedback from MArinas and StartClub BNE after launching in-app votingUsing pre-event onboarding and email sequences to improve attendee engagementReducing theme customisation so the SixSides mobile app can feel more polished and consistentGot 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: sixsides

    52 min

  5. May 25

    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 MobbinUI.shThe 4 Levels of SaaS Landing Page UI DesignChapters (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 routineThe upcoming Marinas event, and what it has taught us about onboarding larger eventsWhy hands-on customer support still matters when you are bootstrapping a SaaSGavin’s nine sales meetings in one week, and what that says about the new lead generation motionUsing DealBuddi and Gamma to quickly produce a professional proposalThe difference between strategic white papers and lighter proposal decksWhat we are learning from LinkedIn content, and why the strategy is changingMoving SixSides-focused posts to the company pageBuilding personal founder audiences through build in public postsCreating a sales dashboard to track effort, pipeline, and revenueThe cost and strategy behind thoughtful cold outreachMitch accidentally rediscovering Gavin’s Canva integration ideaThe August roadmap for the World Police and Fire GamesPreparing the SixSides marketing website for a potential spike in attentionTurning changelog entries into feature pages, use case pages, and industry pagesUsing AI tools to improve product marketing and website designShipping scheduled notifications and live voting for eventsWhy August could become a major turning point for SixSidesGot 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: sixsides

    55 min

  6. May 18

    64: David vs multiple Goliaths

    In this episode, Mitchell and Gavin recap Mitch’s Tasmanian honeymoon, unpack a sudden surge in leads, build out management reporting and Slack notifications, and wrestle with how SixSides can compete with much larger event platforms without hiding what makes the product special. Chapters (00:00) - Intro and audio note (01:18) - Life after the wedding and Mitch’s honeymoon (14:10) - So many leads (17:54) - Building management dashboards (19:49) - Slack notifications and sales visibility (27:00) - Startup World Cup and the next three months (34:26) - How do we compete with larger competitors? (47:47) - Building a changelog for SixSides (51:45) - Dev updates - Bento, attendee search and notifications (54:16) - Voting, app releases and managing the dev team In this episode, we cover:Mitch’s honeymoon in Tasmania, including Hobart, Bruny Island, Port Arthur, Freycinet and LauncestonThe shift from being “on the tools” to building a management and reporting structureA growing number of leads coming through LinkedIn and HubSpotWhy the team may need better dashboards to track revenue, pipeline, lead indicators and website activityUsing Slack notifications to surface new deals, website visitors and product activity across the teamGavin’s trip to a Startup World Cup info night and why he wants to pitch SixSidesThe massive three month lead-up to the first World Police Games releaseHow SixSides should prepare its website, onboarding and positioning for more international exposureHow small SaaS companies can compete with larger competitorsWhy public product docs, feature pages and changelogs might be worth the competitive riskHow AI changes the speed at which competitors can copy featuresBuilding a changelog as a signal that SixSides is becoming a more mature product businessDev updates including Bento integration, attendee search, notification scheduling, adjustable logo heights and votingHow Mitch is evolving the engineering review process with Martin and RaymondGot 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: sixsides

    1 hr

  7. May 12

    63: Nine leads and a wedding

    In this episode, Mitchell returns from his wedding and honeymoon break to find Gavin, the team, and the SixSides sales machine starting to build real momentum, with new leads coming in, LinkedIn and cold email taking shape, a potential SixSides community on the table, and an unexpected trademark issue in Singapore forcing the founders to get serious about protecting the brand. Chapters (00:00) - Intro and Mitchell’s wedding recap (05:36) - Travel touches, DJs, dancing, and photo booths (12:06) - The sales machine is starting to work (13:36) - Managing the team while Mitchell was away (17:37) - Website traffic, PostHog, and app designer behaviour (18:25) - LinkedIn outreach and cold email (19:17) - Building a proper sales structure (20:16) - Why SixSides may need its own community (25:53) - The SixSides trademark scare in Singapore (31:10) - Wrapping up and what is next for the team In this episode, we cover:Mitchell’s wedding recap, including travel-themed details, geese, photo booths, and Gavin on the dance floorWhy founders probably should not pretend they will work “just one hour a day” on holidayHow Gavin managed the business while Mitchell was awayThe pressure of onboarding new team members while one founder is offlineThe early signs that the SixSides sales machine is starting to workNew leads coming in through the business, and how the team is handling follow-upBuilding a clearer sales structure around LinkedIn, cold email, content, and communityWhy not every prospect is in a buying cycle, and how community could help bridge the gapWhether SixSides should build its own event manager community on SixSides or start on another platformUsing PostHog to better understand how people move through the SixSides website and app designerTrademarking SixSides after a Google Play Store issue in SingaporeThe challenge of protecting a SaaS brand internationally as a bootstrapped startupGot 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: sixsides

    32 min

  8. May 4

    62: How to stay married while bootstrapping a SaaS (with Mel Tye)

    In this episode, Gavin is joined by his wife Mel to unpack how they met, how they process risk differently, what it is like watching SixSides grow from the sidelines, and why trust, communication, and the occasional hard conversation matter when you are building a bootstrapped SaaS around family life. Chapters (00:00) - Mel’s first podcast begins (02:10) - How Gavin and Mel met (07:40) - Same values, very different ways of processing information (13:20) - Work, motherhood, control, and learning to let go (18:50) - Gavin’s many business ideas before SixSides (26:30) - From Sales Market Fit to DealBuddi (33:20) - How Mel reacted to SixSides and meeting Mitch (42:00) - When your co-founder becomes part of the family (49:10) - Big client wins and the next phase of SixSides (56:30) - Advice for founders and their partners In this episode, we cover:Mel’s first ever podcast appearanceHow Gavin and Mel met while working in recruitment and electrical contractingFirst impressions, nervousness, arrogance, and how people can be misreadThe difference between Gavin and Mel’s decision-making stylesGetting comfortable with risk when your partner is a founderGavin’s long list of past business ideas, including importing products, dog mats, lights, car mattresses, Cards Against Humanity, and 3D pensHow Sales Market Fit evolved into DealBuddiWhy Gavin’s sales skills work best when he is helping other people clarify and sell their own ideasThe $20K course decision, and what it taught Gavin and Mel about making big financial calls togetherHow Mel felt when Gavin first started working with Mitch on what became SixSidesWhy meeting Mitch and Nicole mattered personally, not just professionallyThe blurred line between business partnerships, friendships, and familyWinning the World Police and Fire Games, and the role of long-term effort rather than luckSigning the Civil Contractors Federation as a major new SixSides clientMoving into the next phase of SixSides, including team management and additional supportAdvice for founders and partners on communication, money, risk, and staying alignedGot 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: sixsides

    53 min
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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
    69
  • Rating
    Explicit
  • Copyright
    © 2025 SixSides
  • Show Website
    Our B2B SaaS Journey