Made with Grit

After bootstrapping Median, why go venture-backed with Workshop?Derek talks about their $3mm seedEasier to raise after some winsWhat has been different about having capital from the start?Derek talks about some of the marketing strategies that are helping them build up a large following in the HR spaceAcquired a newsletter for $6kRunning ads that point to templates accessed by filling out an email formHubspot formLinks:WorkshopWorkshop Raises $3mmPrevious episode with Derek@dhomann

Notes:First post-covid vacationsNew hire running customer operations and freeing Landon up to sellThe struggles of handing-off tasks you've owned for yearsForce testing how the business runs without youWhat is a customer ops manager?What Landon has been doing on the outbound sales side and how it's goingA new product direction/use case that's brought on $100k in ARR in the past few monthsHow to find these opportunitiesHow we're feeling about the Userfeed acquisition six months later Outbound sales emailCopy pointersIndustry-based sequencesTacticsWhen email works and when it doesn'tHow we approached outbound at Rigor (selling to enterprise in a highly competitive incumbent market)Personalization do's and don'tsWhy making assumptions in emails workLandon's first seed investment (Grayscale). See episode 15 where we talked to the CEO of Grayscale (Ty) about his business. By the way, they're hiring.Links:MixMaxHubspotRigor 

Landon and Kyle discuss growth, hiring, and selling business ideas.Today's Topics:Getting back in the officeGrowing revenue by following leads, expanding offeringsHiring for help with customer operationsDifferentiation vectors: usability, functionality, design, etc.A storefront for business ideas?Coming soon: Made with Grit swag

Notes:Why did we sell?How did we sell the business?MicroAcquireManaging leads and sharing information with potential buyersHow long did it take?What were the terms?What went well and what would we do differently?Why focus is important

Today's Topics:Clubhouse takes...what is it good for?Update on Landon's stock trading "hobby"What we're drinkingNew Webflow marketing site launchedIt's tax time - R&D tax credits & filing servicesUpdate on what we're buying: Cocofloss, coffee deliveryLandon got a new Apple watchChanging the default music app on iOSWe're getting M1 MacbooksLinks & Resources:Clubhouse (no, not this Clubhouse)Capiche.fm - Talk to the internetUncle Nearest WhiskeyAgora - Realtime video and voice engagementNew Ad Reform website on WebflowEndorsal - Customer testimonials, automatedCheckly - Delightful active monitoring for developersMainstreetTaxfyleCoco FlossBottomless Coffee (Kyle's referral link)

Episode SummaryTyler Williams on bootstrapping and selling Motion Array for $65 Million. Episode NotesToday's Topics:After selling your company for $65mm what was your first purchase?The story on how they sold the businessWhy they bootstrapped the businessWhat is Motion Array and how did Tyler come up with the ideaWhat move really made the business take offThe importance of SEO and why bootstrapped businesses need to find free/cheap distribution channelsVenture Studio model Failure.incSome ideas he's cooking up for his next ventureLinks & Resources:Motion ArrayArtlist acquisition of Motion ArrayFailure.incTyler Williams on Twitter

Today's Topics:A lot of momentum for alt-funding options like PipeMoney is cheaper, with less "baggage" than ever beforeMarketplace for selling a smaller SaaS is growingBest time ever to be a bootstrapped founderComparing our march to $1mm ARR vs what it was like getting there in our previous company 5 years agoWhat we're drinkingRecent fancy DTC purchases we've madeMade with Grit T-shirt design in the worksRegulation changes for crowdfunding Links & Resources:PipeHausMiniMeisCasper glow lightsExposureCoco FlossFatherly

Today's Topics:Deleting Twitter from phone and using MailbrewWhat are we drinkingHow we performed our first profit shareWhy invoice collections are a huge pain for a small teamBootstrapped business ideasMade with Grit t-shirtsLinks & Resources:MailbrewTip Top canned cocktailsNathan Barry: Profit-sharing for bootstrappers

Landon and Kyle discuss the idea of avoiding popular SaaS markets and give their thoughts on building in public (while sipping on some bourbon & eggnog). They also give their thoughts on some of the recent SaaS acquisitions. Today's Topics Include:Their podcast drinks of choice Acquisitions of Kustomer (Facebook) & Slack (Salesforce)New product: BumpBuilding in public? Pros and cons Learnings are helpfulLeads to more competitorsMore interested in klout instead of businessSpending more time showing you're building in public than actually buildingMany 'open startups' move away from that as they growGiving a business more time to mature90% of companies still aren't using cloud-based softwareThese are the unsexy nichesLinks & Resources:Salesforce, Slack, and the future of workBump

Landon and Kyle discuss their business bouncing back from the dip they experienced during the beginning of the pandemic. They also discuss their previous company getting acquired by Splunk. Today's Topics Include:Kyle's long absence from the podcastAd Reform's revenue bouncing back strong after the pandemic dip Userfeed launch of a new Intercom app: BumpKyle and Landon's previous employer, Rigor, selling to Splunk for 8-figuresUS election crazinessKyle and Landon getting new houses and dealing with the movesLinks & Resources:RigorRigor acquired by SplunkBump

Landon and TJ discuss what it's like transitioning from services to products, bootstrapping, selling to NGOs/healthcare, and being motivated by the impact their products have on the world. TJ also talks about how his global health data SaaS is having quite a moment in the year of COVID, sparked by a free tool that tracks Coronavirus data. Today’s Topics:ATL tiesBootstrap or raise?Services to productsBuilding for impactWhen to cut your losses and move to the next idea or product"Luck is the residue of design"Building a fully remote teamGlobal health data and how COVID has shined a light on the spaceCovid Mapping ProjectSelling, contracts, and collections pains in the healthcare industryProfit-sharing and owner distributionsLinks & Resources:Secure Data KitNTDeliverCovid Mapping ProjectSwitchyardsAtlanta Tech VillageNathan Barry on profit-sharing@TJMule

Landon and Baird discuss what it's like starting and running multiple SaaS businesses. Baird's businesses include Wavve, Zubtitles, Duplikit, and Churnkey and are doing over $2mm ARR combined.Today’s Topics:Should you build more than one SaaS?One company or multiple?Dealing with support/churn across multiple businessesWhat's more important: growth or retention?Moneyball approach to prioritizationLow effort, high impactAsync communication and decision-makingLinks & Resources:WavveZubtitlesDuplikitChurnkey@BairdHall

Jeff Gardner of Graphy joins Landon and Kyle to discuss his 8-year journey at Intercom. He chats about the early days of the product (he was employee #4), growing a support team from 1 to 100, launching a developer platform, and more.Today’s Topics:Intercom pricing (and potential IPO?)Growing support in lockstep with customer growthThe evolution of hiring needs as a company scalesBeing remote in a majority in-person companyGoing from "we have an API" to "we are a developer platform"Advice for indie developers building on a platformBack to the beginning: moving to GraphyWhat is customer success?Customers as collaborators on the product journeyThinking in trade-offsLinks & Resources:Jeff on Twitter: @erskingardnerGraphy: Data collaboration in a visual, fun and flexible wayFinite and Infinite Games by James P. Carse

Landon chats with Derek Homann, co-founder of Median and Workshop, about bootstrapping, working on multiple SaaS products, taking money off the table, and more.Today’s Topics:Building SaaS outside Silicon Valley (in Omaha, in Derek's case)Running multiple SaaS products as a small, bootstrapped teamDerek's career journey: technical recruiter > customer support > director > founderLatest project: Workshop: Collaborative & Actionable MeetingsJumpstarting a business by building on a platformTaking money off the table with perpetual licensingLinks & Resources:Derek on Twitter: @dhomannMedian: Simple CoBrowsing for Support TeamsWorkshop: Collaborative & Actionable Meetings

Kyle and Landon share a company update, then chat about the Facebook ad boycott, stocks, and HEY.Today’s Topics:How the pandemic has impacted revenue and growthPaused customers are returning...will that continue?The pain of getting a home loan as a bootstrapperThe Facebook ad boycott: meaningful, or just posturing?Investing a little money for fun (and maybe profit)HEY, Basecamp, and DHH's Twitter masteryLinks & Resources:Razer Kiyo webcam + lightSquadcastHEY.com

Kyle and Landon discuss recent changes to their product development and marketing processes.Today’s Topics:The psychological impact of slow growthObjective improvements vs. psychological tricksBalancing commitment and responsivenessPrioritization and execution: Serial process, or concurrent threads?Shipping cadence: Minimizing work-in-progress, maximizing throughputMarketing: one-month-at-a-time, one thing per weekFinding rhythm and a sustainable paceLinks & Resources:Intercom's 6 week product cyclesUserfeed video: 3 ways to collect feedbackRescueTime (Kyle's referral link)Userfeed + GitHub integration

Kyle chats with Andy O'Hara, a finance guy turned healthcare entrepreneur (and now a self-taught developer). Listen as they discuss Andy's experience growing an on-demand pediatrics business.Today’s Topics:The acquisition of Andy’s recent companyLearning to code on the job at Chiron HealthBuilding an app simply for an easier dev - and user - experienceAndy’s journey building a telemedicine businessDeciding against the brick-and-mortar route and building an on-demand pediatrics serviceWhat Andy is doing differently with the new companyVC-backed and profitableModern Pediatrics’ roadmap in light of COVID-19Using code and no-code tools togetherNo-code debtLinks & Resources:Andy on LinkedInModern Pediatrics - Let the pediatrician come to youChiron Health - See your patients over HIPAA-compliant video with full reimbursementElixir - A dynamic, functional language designed for building scalable and maintainable applications.Ruby On Rails - A web-application framework that includes everything needed to create dat

Landon chats with Brandon Cummings about his journey from finance, to tech, to starting a non-profit in Atlanta that feeds 6,000 people per week.Today’s Topics:Brandon’s journey from finance, to biz dev, to engineeringThe demise of VoxaBootstrapped vs “going big”A detour into data scienceGoing full-time on a side projectTaking a new job after COVID-19 shuts down the businessBuilding an open source platform for COVID-19 testingStarting a non-profit to feed hospitality workers during the pandemicBuilding software and systems to support feeding 6,000 people a week$20 provides 4 family meals. Donate here.Links & Resources:ATL Family Meal - Feeding 6000 hospitality workers per weekATL Family Meal on Instagram, Twitter, LinkedIn, and FacebookKevy - The best marketing platform for growing salesRigor - Digital Experience Monitoring and OptimizationTerminus - Full Funnel Account-Based MarketingRails Tutorial - Michael HartlCapgemini - A global leader in consulting, technology services and digital transformationFlo

Landon & Kyle have a heated discussion about B2B customer support.Today’s Topics:We got the PPP loan!Decided not to run for presidentWhat we’ve learned about B2B SaaS supportStop calling them support “tickets”Live chat isn’t the problemChoosing to be opinionated about customer feedback managementDon’t make your customers do all the workWhy you should be collecting customer feedback from the beginningLinks & Resources:Business Casual Podcast episide with Ray Dalio (Part 1 and Part 2)Remote Team - Automated Payrolls, Time Off, HR Tools, and Compliance for Remote TeamsCalendly - Super easy online appointment scheduling softwareUserfeed.io - Customer feedback designed for Intercom

Today’s Topics:Kept up all night by…the dogWhat we’re working onNew podcast ideaHandling subscription pause requests due to COVID-19Automating payrollVirtual coffee with the founder of a new SaaSLooking back at the inflection points for Ad ReformTrying to monetize free softwareWhat we would have done differently if we started the business todayIterative billing strategiesJoe Rogan and UFOsLinks & Resources:Remote Team - Automated Payrolls, Time Off, HR Tools, and Compliance for Remote TeamsAds.txt Pro - Monitor ads.txt files, find errors before files go live, and get notified in SlackAd Reform - Your intelligent ad ops assistantUserfeed - Customer feedback designed for Intercom