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. 8H AGO

    57: Building the right team

    In this episode, Mitchell and Gavin unpack a tense enterprise procurement process, share where hiring is up to across lead gen and development, and talk through the product, positioning, and SaaS agreement changes that are making SixSides feel more scalable. Chapters (00:00) - Intro (01:31) - Project Rendezvous and enterprise procurement delays (03:51) - Fitness updates and wedding countdown (07:28) - Hiring plans across lead gen and development (12:38) - Loom screening, technical hiring and what good candidates look like (18:38) - Creating room for initiative and experimentation in the team (23:18) - Project Hammer and expanding within existing accounts (25:12) - Website, design direction and making SixSides feel premium (32:33) - Product updates - dashboard fixes, AI assistant improvements and feature cleanup (38:54) - SaaS agreements, positioning work and wrapping up In this episode, we cover:The procurement panel slowing down a major SixSides deal Whether to keep hiring even before a large contract is formally signed Fitness updates, discipline struggles, and wedding prep Interviewing candidates for lead generation and development roles Why responsiveness and initiative matter more than a polished CV Building a 90 day onboarding plan for new hires Delegating LinkedIn and email outreach as the team grows A new expansion opportunity with Project Hammer Moving customers from one-off events to ongoing SaaS agreements Updating the SixSides dashboard so organisers can manage more without developer help Improving the AI assistant so it can handle links, logos, profile photos, and more event setup tasks Why modern UI matters for an event platform built around connection and community Using product design to make SixSides feel more premium Planning webinars and outreach to convert past event users into future organisers Clarifying SixSides positioning as a community-first event engagement platformGot 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

  2. MAR 23

    56: We're hiring!

    In this episode, Mitchell and Gavin unpack a huge turning point for SixSides as they start hiring, celebrate Project Rendezvous moving into contracts, and talk through how DealBuddi, team structure, and long-term planning are all evolving at once. Links DealBuddi - https://dealbuddi.comChatGPT Atlas - https://chatgpt.com/atlas/Superwhisper - https://superwhisper.comAaron Francis on YouTube - Are designers cooked? - https://www.youtube.com/watch?v=tm9im-3g8fYStitch by Google - https://stitch.withgoogle.comSuno - https://suno.comChapters (00:00) - Editor’s note and intro (00:52) - We’re hiring at SixSides (07:38) - Using Atlas browser and AI to screen applicants (14:08) - Project Rendezvous gets approved (18:49) - What DealBuddi does and why it matters now (27:39) - Rebuilding DealBuddi in Laravel (31:04) - Founder roles, planning styles and playing to strengths (35:23) - National Safety Conference and product adoption lessons (38:44) - PlanetScale spikes and event infrastructure (41:58) - Founders Collective, student work experience and wrap-up In this episode, we cover:Why now feels like the right time for SixSides to start hiringHiring a growth marketer, lead gen support and multiple developersUsing AI tools like Atlas browser to screen job applicants fasterHow voice-to-text workflows with Superwhisper and ChatGPT are changing day-to-day workProject Rendezvous getting committee approval and moving into contract discussionsWhy DealBuddi’s positioning needs work and how it supports real sales conversationsThe plan to rebuild DealBuddi from Bubble into LaravelFounder roles, planning styles and how to play to each other’s strengthsLessons from the National Safety Conference and event app adoptionDatabase load spikes in PlanetScale during live eventsFounders Collective momentum, community building and staying in touch between eventsWhy student work experience is a good idea, but not the right fit just yetGot 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

  3. MAR 16

    55: That's tree trimming money

    In this episode, Mitchell and Gavin unpack a huge week of live events, reflect on the first real signs of SaaS leverage inside SixSides, talk through plans to hire their first extra team members, and share why Project Rendezvous could become a major turning point for the business. Chapters (00:00) - Intro (01:25) - CCF Women in Civil and a big week of events (03:31) - We’re not engaging with attendees properly (08:13) - We’re hiring (12:03) - Good signs for Project Rendezvous (20:43) - Project Hammer Brisbane and tree trimming money (27:45) - Bridging the gap between operations and dev with Linear (39:09) - NSCA tomorrow (40:31) - Understanding the user journey on our site with PostHog (43:41) - When do we hire for AI and agents? In this episode, we cover:What happened at the CCF Women in Civil event and how attendee usage is improvingWhy SixSides needs a better post-event attendee engagement strategyHow the team is thinking about email automation and lifecycle messaging with BentoThe current growth in platform users across all SixSides eventsWhy Mitchell and Gavin are planning their first hires across development and lead generationHow Project Rendezvous could unlock faster growth and more engineering capacityThe moment SixSides started to feel like a real software business with paid events running without hands-on supportLessons from Project Hammer and how event setup is becoming more repeatableBridging the gap between operations and development with better planning in LinearWhy the team is looking at PostHog to better understand the user journey on the marketing websiteHow bootstrapping affects hiring, planning, and long-term product decisionsWhen AI agents might become part of the team structureGot 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

  4. MAR 9

    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

  5. 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

  6. 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

  7. 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

  8. 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
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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
    57
  • Rating
    Explicit
  • Copyright
    © 2025 SixSides
  • Show Website
    Our B2B SaaS Journey