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. 6D AGO

    54: There is so much to do

    In this episode, Mitchell and Gavin celebrate their fastest client win yet, prepare for five events in seven days, share updates to the SixSides app and dashboard, and unpack the growing pressure of building a bootstrapped SaaS when the momentum finally starts to kick in. Chapters (00:00) - Intro (00:19) - Fitness update and hitting new milestones (03:42) - Fastest client win yet (06:46) - Five events in seven days (10:35) - Building the first user guide (14:59) - Should we go back to AIM next year? (18:11) - Product updates in the app and dashboard (22:33) - There is so much to do (31:31) - Should we hire our first developer? (38:05) - Outro In this episode, we cover:Fitness progress and how personal routines are tracking alongside startup pressureOur fastest client win yet and what made the sales process workHow a quick Loom walkthrough helped close a new event customerWhy community building keeps coming up in SixSides sales conversationsInvoicing momentum and how March revenue is already beating last yearPreparing for five events in seven days across multiple customersThe operational risk of becoming the bottleneck as event volume growsBuilding a first draft attendee user guide for event clientsUsing Gamma to speed up polished documentation and onboarding assetsWhy sponsor and exhibitor workflows could become a product-led growth leverRecommitting to AIME as a key conference for future customer growthNew SixSides product updates including sponsor tier layouts and feature togglesFixing AI assistant tooling issues in the dashboard backendThe growing product roadmap across the website, dashboard, infrastructure and mobile appWhether it is time for SixSides to hire a first developerThe realities of bootstrapping while juggling multiple businessesGot 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

    39 min

  2. MAR 2

    53: Our biggest deal yet

    In this episode, Mitchell and Gavin celebrate one year of podcasting, lock in their biggest client commitment yet with four more events booked through to EOFY, and unpack what’s next across dashboards, lead gen follow-ups, Linear vs Slack, and a big push towards a better AI workflow inside SixSides. Chapters (00:00) - Intro and one year anniversary (02:40) - Biggest deal yet - four more events booked (06:27) - Project Rendezvous - still waiting (07:34) - Leadfeeder signals and why the website needs work (10:46) - Slack channel vs Linear for feature requests (15:58) - AI inside SixSides - Vercel AI SDK, agents, and better chat UX (22:14) - Infra fatigue and keeping the work fun (27:02) - AIM follow-ups and lead gen reply reality (29:36) - The DICE - mailing packs and handwritten notes (31:19) - Fitness check-in and staying consistent In this episode, we cover:One year of podcasting and how routine keeps the business groundedLanding the biggest SixSides deal so far and booking four more events through to EOFYHitting 93% event app adoption and what might be driving itProject Rendezvous delay and learning to live on other people’s timelinesUsing Leadfeeder-style tooling to see who’s checking out the SixSides siteWhy the marketing site needs screenshots, walkthroughs, and a proper sign-up pathLinear vs Slack for feature requests and how to keep dev work organisedUsing AI inside SixSides to duplicate events and reduce setup grunt workMoving towards the Vercel AI SDK and improving agent workflows, approvals, and attachmentsParking infra work to stay motivated and keep shippingAIM follow-ups, outreach reply rates, and lead gen back in motionThe DICE mail-out plan and handwritten notes for supportersFitness routines, travel disruption, and staying consistent over perfectionGot 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

    37 min

  3. FEB 23

    52: This episode is mostly technical

    In this episode, we go mostly technical - Mitchell migrates the SixSides dashboard from Vue to React, moves the database to PlanetScale, and outlines the plan for proper preview environments that go from Linear to Cursor to live. Along the way there’s a fitness check-in, a disrupted Canberra trip, Project Hammer running without us on-site, and a new plan for an event manager success playbook. Links mostlytechnical.comChapters (00:00) - Intro, billionaires, and the Christmas present (05:00) - Anniversary trip recap - escape room, Harbour Bridge nope, ice cream mission (08:50) - Fitness updates - gym habits, 75 Hard halfway, and easing into running (14:20) - We’re a React app now - why we moved from Vue (20:05) - PlanetScale migration - ditching RDS and simplifying the database setup (25:05) - Cost reduction and scaling globally into other regions (27:30) - Import issues, support fixes, and the “metal instance” workaround (32:50) - Linear to Cursor to live previews - the new dev workflow (41:30) - Project Rendezvous, CCF Magazine, and external deadline pressure (48:25) - Canberra trip disruption, Project Hammer lessons, and mailing out the dice In this episode, we cover:The “billionaire” Christmas present (Zimbabwean dollars, obviously)Anniversary trip vibes, escape rooms, and bailing on the Harbour Bridge walkFitness updates - 75 Hard progress, running blocks, and sore feetWhy SixSides is now a React dashboard (goodbye Vue)Using Cursor to accelerate a React rewrite and why popularity matters for AI toolingMoving the SixSides database from AWS RDS to PlanetScaleConsolidating global and regional databases into a simpler modelData sovereignty trade-offs (and when it’s worth paying for)Big cost reduction for adding regions (from hundreds to tens per month)The plan for preview environments: Linear tickets - Cursor agents - live preview linksReplacing Laravel Vapor with Terraform for better automationProject Rendezvous update and what “due diligence” could look likeCCF Magazine editorial deadline pressureCanberra trip disrupted, then Sydney trip pivotProject Hammer ran without the founders on-site - lessons learnedBuilding an event manager success playbookMailing out SixSides dice to leads - and a review-for-dice offer Got 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

    58 min

  4. FEB 16

    51: We shipped our dashboard between bike rides

    In this episode, Mitchell and Gavin debrief their first big AIME conference trip - from Mitch’s truly unhinged packing list to what they learned meeting organisers face-to-face, how they plan to follow up leads, and why the new SixSides dashboard and AI workflows suddenly became the star of the booth. Chapters (00:00) - Intro (02:05) - What did Mitch pack? (06:34) - Relocating to Melbourne - podcast gear, desktop PC, and the mic-in-a-cup moment (11:12) - AIME debrief - nerves, then finding the groove (13:23) - Selling lessons - human first, outcomes over features (16:35) - Lead follow-up plan - LinkedIn connects, then email sequencing (17:49) - Dice idea - why we want them at every event (20:14) - Booth lessons - placement away from competitors and why banners weren’t the play (22:22) - The Monday sprint - shipping the dashboard demo fast (24:05) - What we’d change next time - travel days, flights, schedule and dress code (28:19) - Project Hammer update and meeting Joe in person (29:10) - Dashboard and AI workflows - self-serve events and production rollout (35:49) - The “exercise trip” recap - 40k steps, food, and no relaxing (37:16) - The tan track and the uphill cycling humiliation (39:43) - Project Rendezvous white paper - global rollout strategy and what’s next In this episode, we cover:Mitch’s chaotic travel kit - steamer, mini fan, full desktop PC, and podcast gearAIME conference debrief - nerves, first conversations, and surprising momentsWhat worked at the booth - demoing dashboards, theming, and speed of executionHow Mitch and Gavin approach conversations differently - features vs outcomesLead follow-up plan - LinkedIn connects, email sequencing, and timingDice update - why physical gimmicks might matter more than bannersLessons learned - flights, schedules, attire, and staying until the endThe SixSides dashboard - self-serve event setup and getting Mitch out of the loopProductivity gains with AI tooling (with a bigger tech stack chat teased for next week)Exercise and travel routines - 40k steps, sore legs, and avoiding weight creepProject Rendezvous update - white paper strategy and “initial rollout” framingFounder Collective update - co-hosting with The Precinct and upcoming events Got 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

    51 min

  5. FEB 9

    50: Live from Melbourne

    In this episode, Mitchell and Gavin record in person from a Melbourne hotel room ahead of AIM, share what it cost to exhibit and what they’re actually trying to achieve, and unpack big momentum updates across Project Rendezvous, CCF, and a major push to get SixSides dashboards ready for live demos. Links atlas.devChapters (00:00) - Audio note - recording in person with two mics (00:28) - Live from Melbourne - exercise trip meets lead gen trip (02:53) - Morning person vs night person (and the need for naps) (05:39) - Project Rendezvous update - multi-year potential and pricing pressure (08:29) - What AIM is and why we’re exhibiting (09:23) - Booth setup - reusable banner, shipping pain, and vendor shoutout (12:19) - Booth envy - avoiding the event tech aisle and why positioning matters (15:08) - Conference strategy - lead rating, rapport, and follow-up commitments (17:12) - Pricing direction - per-event pilots to SaaS, dashboards as the key (26:57) - Shoutout to Clay Smith on Bluesky (28:44) - CCF President’s Lunch recap - JT on stage and Tag, You're It via event photos (31:51) - Dashboards build sprint - consolidating repos and shipping fast with AI (35:42) - Using AI for white papers - foundations first, then polish (38:13) - Weight loss update - 5kg down, walking focus, no booze habits (46:00) - Lessons learned coming next week - pitching, exhibiting, and confidence building In this episode, we cover:Recording in person from Melbourne and the joys of mismatched micsExercising like maniacs and discovering who’s a morning person vs a night personWhat AIM is, why we’re exhibiting, and how much it costBooth setup decisions, reusable banners, and avoiding the intimidating event tech aisleConference lead strategy - cold/warm/hot leads and getting commitment to follow upProject Rendezvous update - pricing pressure, US decision makers, and multi-year deal potentialShifting from per-event pricing to SaaS pricing, and why dashboards are the unlockThe CCF President’s Lunch recap, JT on stage, and a new angle for Tag, You're It using event photosHow we’re both using AI - white papers for sales, dashboards for product iterationMitch’s weight loss journey update Got 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

    47 min

  6. FEB 2

    49: Why we're being so transparent

    In this episode, we unpack why we’ve chosen to be so transparent on the podcast - the upside for listeners, the potential risks with customers and competitors, and where we draw the line on sharing sensitive details. We also share a stack of updates as AIME approaches, including meeting bookings, a new client trial, analytics learnings from Heroly, multi-agent AI workflows, and a big strategic planning prompt from Inductive. Plus, wedding prep and fitness check-ins to round things out. Chapters (00:00) - Intro (00:46) - AIME meeting bookings update (Gavin on 11+, Mitch on 3) (03:20) - Banner logistics and prep for Melbourne (06:07) - The secret AI breakthrough teaser for AIM (09:28) - Why we’re being so transparent (and the downsides) (16:34) - Being “small” vs getting on people’s radar (18:40) - New client trial and shifting to community-based pricing (20:43) - Why short events don’t suit “tagging” features (22:10) - Catching up with Heroly: analytics, AI and advice (24:35) - Using multiple AI agents in parallel (what worked, what didn’t) (29:00) - Claude Code vs Cursor experiments (30:02) - Project Hammer update and deadlines (30:40) - Inductive session: backcasting to $10M-$20M (32:45) - Wedding planning update (catering, dogs, MC/DJ, photo booth, bus) (37:41) - Fitness check-in (weight, habits, 5k walks, Apple Watch, Strava) (46:24) - Episode 50 coming up and outro In this episode, we cover:Why we’re choosing transparency, and what could go wrongThe trade-offs between “looking big” vs being honest about being smallAIME prep: meeting bookings, banners, and how we’re pitching the standA new client trial and testing a community-based, ongoing pricing modelWhy “tagging” style features don’t suit short events and meetupsLearning from Heroly's analytics setup (and what we’re missing)Using multiple AI agents in parallel without melting your brainCursor vs Claude Code, and what we’re experimenting with nextProject Hammer update and timelines for event setupBackcasting with Inductive to plan for a $10M-$20M futureWedding planning progress and suit decisionsFitness habits: daily 5k walks, early gym sessions, and staying consistentEpisode 50 coming up Got 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

    47 min

  7. JAN 26

    48: No dice

    In this episode, we debrief a not-quite-right funding program (and a rejection that honestly saved us time), share encouraging momentum on Project Rendezvous, and get into full pre-conference mode for AIME in Melbourne - flights, accommodation, banner logistics, meeting bookings, and the lead capture tool build. Chapters (00:00) - Intro - wedding prep and what’s on this week (07:01) - Funding chat - rejected for the first interview and why it wasn’t a fit (10:15) - Project Rendezvous update - signs are positive (and it could change everything) (14:25) - Marinus check-in - timelines, sponsors, and expectations (15:23) - Lead capture tool progress - backend done, frontend next (18:36) - AIME prep - flights, accom, and the Melbourne plan (21:26) - Credit card points - Amex without spending beyond your means (23:25) - Booth logistics - banner arrives and meeting booking portal opens (26:00) - No dice - supplier drama, refunds, and the Alibaba pivot (29:30) - 75 hard vs 75 medium - fitness updates, shin splints, and staying consistent In this episode, we cover:Why the accelerator style funding program wasn’t a fit (10 weeks in-office with no guarantee)A positive update on Project Rendezvous and what “long-term partner” could meanCatching up with Marinus ahead of their May conference and sponsor scale (60+ exhibitors)Progress on the sponsor lead capture tool - backend done, frontend nextWhether the lead capture tool should become a separate appAIME conference prep - flights, accommodation, bikes, and daily walking plansApplying for an Amex to earn points on business spend (without spending beyond your means)Banner arrived - and it’s way heavier than expectedMeeting booking portal opened and how we’ll approach outreachThe dice order saga, the refund, and switching to Alibaba for cheaper dice75 hard vs 75 medium updates - plus shin splints, walking plans, and diet tweaksExpect 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 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

    40 min
  8. 47: We're thinking about funding

    JAN 19

    47: We're thinking about funding

    In this episode, Mitch and Gavin ease back into the year with a big life update (Mitch’s tea ceremony), some very real fitness chat, and then get into the spicy question they keep circling - should SixSides consider funding to accelerate growth? Chapters (00:00) - Intro and personal stuff (17:30) - Back to business - AIM prep (18:29) - Booth logistics - table hire costs and keeping it simple (19:04) - Ordering dice, cancelling the order, and refunds (19:49) - Shout out to Nick Taylor (20:56) - Booking flights and timing around AIME (21:24) - Main topic - we’re thinking about funding (25:30) - What funding changes for Gavin (focus, lead gen, capacity) (29:08) - The trade-offs - bosses, reporting, networks, advice (31:10) - Lead capture tools and sponsor lead gen pricing (34:14) - Reducing reliance on attending events in person (37:31) - Getting the most out of a work trip (Project Hammer travel stacking) (39:35) - Referral to an international events company (40:16) - Wrap up and where to find us In this episode, we cover:Mitch’s edit note - the first 17 minutes are very not-businessGetting back into fitness - 75 Hard, 75 Medium, and 75 EasyParkrun follow-up, chafing survival strategies, and being sickMitch’s tea ceremony recap - games, challenges, and family speechesAIME prep - booth setup decisions, signage, hiring tables, and keeping it simpleOrdering custom dice and cancelling a dropship orderShout out to Nick Taylor and the promised diceBooking flights and planning travel around eventsThe big topic - funding vs bootstrapping and what “full-time” would changeLead capture tools, sponsor lead gen, and how to create more inbound opportunitiesReducing reliance on attending events in person and planning for clashes and overseas eventsReferrals and partnerships that could pull SixSides into new regionsExpect 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 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

    41 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
    54
  • Rating
    Explicit
  • Copyright
    © 2025 SixSides
  • Show Website
    Our B2B SaaS Journey