The SaaS Podcast - AI, Growth & Product-Market Fit for SaaS Founders

Most SaaS companies invest heavily in content creation and then do nothing to promote it. Alan Silvestri built an entire agency around fixing that SaaS SEO strategy gap - and his outreach email was so good it landed him on this podcast after Omer initially said no. In this episode, Alan walks through his exact SaaS SEO strategy for link building and content promotion. He explains why most outreach fails, how to reverse-engineer competitor backlinks to find untapped prospects, and the SaaS content marketing process that separates companies dominating organic search from those with content graveyards. Growth Gorilla's link building playbook distinguishes between "money pages" (keyword-targeted content) and "linkable assets" (content designed purely to attract backlinks). Alan's content promotion process uses personalized outreach that leads with genuine value rather than generic pitches. Key Lessons 🎯 SaaS SEO strategy requires equal investment in creation and promotion: Publishing content without promoting it creates a "content graveyard." Alan says companies should invest as much time in link building as they spend on content creation. 📧 Personalized outreach gets replies, generic pitches get deleted: Alan's email to Omer stood out from thousands because it led with value and personalization. Your outreach should ask questions and offer help, not pitch your company. 🔄 Reverse-engineer competitor backlinks to find untapped prospects: Instead of contacting the same sites linking to competitors, analyze what types of pages link out. Then find similar pages not linking to anyone yet for better SaaS SEO strategy results. 💰 Separate money pages from linkable assets in your content strategy: Money pages target keywords and drive conversions. Linkable assets like infographics attract backlinks. Use both to build domain authority that lifts all your content. 📉 SaaS SEO strategy results are exponential, not linear - do not quit early: Most companies see 20% of results after 80% of effort and give up. Committing long-term separates companies that dominate organic search from those with content graveyards. Chapters Introduction Alan's favorite quote: Marty McFly from Back to the Future What Growth Gorilla does: content promotion for B2B SaaS Why content promotion matters for SaaS companies The content graveyard: why most SaaS content never ranks Common SaaS SEO strategy mistakes How Alan's outreach stood out and led to this podcast The skyscraper approach and why it stopped working Reverse-engineering competitor backlinks for untapped prospects Money pages vs. linkable assets in SaaS SEO strategy Building a prospect list and finding the right contacts How to prioritize which pages to promote first Combining Ahrefs data with Google Analytics conversions Creating a 12-month content marketing roadmap The outreach email that actually gets replies Personalization at scale: tools and processes Follow-up strategy: value first, ask second The exponential curve of SaaS SEO strategy results Lightning Round Wrap Up Resources Full show notes: https://saasclub.io/299 Join 5,000+ SaaS founders: https://saasclub.io/email

Dave MacLeod spent years trying to sell to everyone and got nowhere. Then he focused his SaaS go-to-market on one niche SaaS market - school districts - and that single decision built a $20M business. For almost five years, ThoughtExchange focused exclusively on K-12 education. That SaaS go-to-market discipline gave them sharp messaging, passionate customer advocates, and a product purpose-built for one buyer. Today, half their business comes from Fortune 100 enterprise customers - but only because they committed to vertical focus before going wide. Dave's go-to-market strategy proves that niche SaaS focus creates the foundation for broad expansion. ThoughtExchange grew to $20M ARR with 200 employees and $45M in funding by resisting the temptation to chase every market opportunity. Key Lessons 🎯 SaaS go-to-market focus on one market is how you find product-market fit: ThoughtExchange tried selling to everyone and failed. Focusing exclusively on school districts for 5 years built a $20M ARR business with passionate customer advocates. 📉 Building a product before finding a problem is the classic mistake: Dave and Jim created collective intelligence software first, then wandered looking for buyers. They heard "interesting but not for us" repeatedly until finding education. 🏢 Niche SaaS discipline creates the foundation for enterprise expansion: ThoughtExchange built product depth and customer references in education that made Fortune 100 sales possible. Half their revenue now comes from corporate enterprise. 💰 Stay in your market until customers recruit for you: Dave says you have not found product-market fit until 10 customers voluntarily take reference calls, go on stage, and help you sign up others in the same market. 🧠 A billion-dollar company grew by doing 80% less, not more: A CEO with nearly $1B in revenue told Dave the same SaaS go-to-market truth - focus is critical at every stage, not just the early days. Chapters Introduction Dave's favorite quote: good judgment comes from experience What ThoughtExchange does: discussion management for large groups Origin story: the outdoor guide and the physicist Business size: $20M ARR with 200 employees and $45M raised The "terrible" mistake of building product before finding a problem Recipe cards and infinite recipe cards: how the idea was born Struggling to find customers: "interesting but not for us" The school superintendent who changed everything Going all in on one niche: SaaS go-to-market with school districts Why niche focus works: customers become advocates When to know you are in the right market The temptation to expand too early Investor pushback on an education focus Building vertical-agnostic features inside a niche market Expanding from education to corporate enterprise The billion-dollar CEO who grew by doing 80% less How half the business now comes from Fortune 100 Lightning Round Wrap Up Resources Full show notes: https://saasclub.io/298 Join 5,000+ SaaS founders: https://saasclub.io/email

Santi Bibiloni was stuck at $2K MRR selling to small agencies. Then he shifted his enterprise sales strategy upmarket and started closing multi-year contracts with some of the largest agencies in the world. In this episode, Santi reveals how COR went from offering free trials and monthly plans to eliminating free trials entirely, selling annual and multi-year contracts to CFOs, and growing to between $1M and $2M ARR with 9% month-over-month growth. His enterprise sales playbook targets CFOs at agencies with 50-200 employees through B2B SaaS sales cold email with an 86-day average cycle. COR's shift from SMB to enterprise SaaS transformed their metrics: 114% net revenue retention and just 4.5% annual dollar churn. Santi's B2B sales process proves that customizing the demo - not the product - closes enterprise sales deals faster. Key Lessons 🏢 Move enterprise sales upmarket when SMB growth stalls: COR was stuck at $2K MRR selling to small agencies. Shifting to mid-market and enterprise with 50-200 employees unlocked 7-figure ARR and 9% monthly growth. 🎯 Define your ICP down to buyer persona and company size: Santi targeted CFOs at creative agencies with 50-200 employees. This specificity made cold email outreach and enterprise sales messaging dramatically more effective. 💰 Eliminate free trials and sell multi-year contracts instead: COR dropped free trials entirely and moved to annual and multi-year contracts, increasing prospect commitment and reducing churn from 15%+ to 4.5% annually. 📧 Cold email to CFOs outperforms paid ads for enterprise sales: COR spent their angel round on Google and Facebook ads with poor results. Almost all enterprise SaaS revenue came from cold email outreach and email lead nurturing. 🤝 Customize the demo, not the product in enterprise sales: COR shows each prospect how their specific pain points are solved rather than doing generic feature walkthroughs, making every demo feel personal without building custom features. Chapters Introduction Santi's favorite quote: think big, take risks, be resilient What COR does: project profitability platform Business size: $1-2M ARR with 9% monthly growth Origin story: running an e-commerce agency in Argentina Building the MVP and getting two agencies to try it Early users hated the product but kept using it Raising an angel round and wasting money on paid ads Why paid advertising failed without a clear ICP Moving upmarket from SMB to enterprise sales Cold email vs. paid ads: what actually worked Lead nurturing and email marketing strategy Defining ICP: CFOs at agencies with 50-200 employees Personalizing cold email for enterprise sales Eliminating free trials and selling multi-year contracts Multi-stakeholder enterprise sales process Average 86-day enterprise sales cycle Lightning Round Where to find COR and Santi Resources Full show notes: https://saasclub.io/297 Join 5,000+ SaaS founders: https://saasclub.io/email

Jon Fagg spent 18 months struggling to get 10 paying customers. Then he introduced a freemium SaaS model, and within six months, Skedda had more signups than they had managed in the previous two years combined. In this episode, Jon reveals how Skedda grew from a side project that three part-time co-founders built across time zones into a bootstrapped 7-figure business with 4,000 paying customers. He explains why the freemium SaaS approach - combined with one focused SEO project - replaced every other channel they tried, including handwritten letters in the mail. The freemium model unlocked free trial conversion at scale. Skedda replaced confusing pricing tiers with a generous SaaS free tier plus one $49 paid plan. That simplicity, combined with vertical-specific landing pages for SEO, created a freemium SaaS flywheel where word of mouth matched organic search as a growth driver. Key Lessons 🎯 Freemium SaaS creates volume that unlocks word-of-mouth: Skedda's free tier drove signups, usage, and feedback that eventually made word-of-mouth as powerful as SEO - all without paid marketing spend. 🔄 Simplify pricing to one freemium SaaS tier plus one paid plan: Skedda replaced confusing alliterative pricing tiers with a generous free plan and a single $49 premium option, making the decision obvious for users. 🚀 One SEO project can replace paid marketing entirely: Jon restructured Skedda's site with vertical-specific landing pages in a single focused effort, and organic search became the primary customer acquisition channel for years. 📉 18 months of failure does not mean the idea is wrong: Skedda's founders tried handwritten letters and various outreach tactics for 18 months before freemium SaaS and SEO unlocked growth - persistence mattered more than tactics. 💰 Bootstrapped freemium SaaS can reach 7-figure ARR without funding: Skedda grew to 4,000 paying customers and multiple seven figures with a team of 15, proving this model can scale without venture capital. Chapters Introduction Jon's motivation: building things with interesting people What Skedda does: space management software Why Skedda exists: flexible scheduling across verticals Customer range: from farmers to Harvard and Mercedes-Benz Business size: 4,000 paying customers and 7-figure ARR Origin story: running a sports facility in Melbourne Recruiting an engineer doing his PhD in Germany Building the MVP and first product iteration 18 months to find the first 10 customers Trying handwritten letters and other failed tactics Introducing the freemium SaaS model and simplifying pricing The SEO project that changed everything Why SEO became the biggest growth driver What held them back from freemium sooner The avalanche effect after launching freemium How COVID accelerated enterprise adoption In-person founder retreats for strategic decisions Lightning Round Wrap Up Resources Full show notes: https://saasclub.io/296 Join 5,000+ SaaS founders: https://saasclub.io/email

Most venture capital SaaS stories start in Silicon Valley with decades of experience. Liam Gerada did it at 19 from a small island in the Mediterranean - with zero coding skills and a brother who was still a teenager. In this episode, Liam reveals how he and his brother Travis built Krepling, a Shopify competitor, from scratch after their own e-commerce struggles. He shares the venture capital SaaS journey that took them from losing every user when they introduced pricing to landing 500 customers and a pre-seed round from Jason Calacanis' LAUNCH accelerator. Their SaaS fundraising success came from traction, not pitch decks. Krepling's startup funding story proves that raising from VCs requires real customer traction. The brothers reached 500 paying customers and $1 billion in platform GMV before any investor took them seriously - overcoming the skepticism of being teen founders from Malta. Key Lessons 🚀 Venture capital SaaS funding requires traction, not just a pitch: Krepling raised from LAUNCH accelerator only after reaching 500 customers and $1B platform GMV - proving that even teenage founders can secure funding with real traction. 📉 Switching from free to paid will expose product gaps: Krepling lost every user when they started charging, but the founders treated it as a signal to improve the product rather than reverting to free. 🎯 Agency partnerships accelerate customer acquisition without paid ads: E-commerce agencies frustrated with Shopify integrations started building client sites on Krepling, creating a word-of-mouth engine at zero cost. 🛠️ Non-technical founders can build MVPs with minimal coding skills: Travis learned just enough coding to build Krepling's first version, and they hired real developers only after validating demand with paying customers. 🤝 Community-driven growth starts with grassroots hustle: Posting on Quora, Reddit, and sending cold emails got Krepling's first 10 customers - enough to prove the concept before approaching venture capital SaaS investors. Chapters Introduction Liam's motivations and working with his brother Travis What Krepling does and how it competes with Shopify How Krepling differentiates from Shopify and BigCommerce Business size: 500 customers and $1B+ platform GMV From Shopify store to agency idea to building a platform Building the MVP without coding experience Launching a free product and attracting early users Every user churned when pricing was introduced How Krepling centralized e-commerce integrations The no-code approach to third-party integrations Getting the first 10 paying customers Agency partnerships as a growth channel Raising venture capital SaaS funding from Jason Calacanis' LAUNCH Hiring the first developer as non-technical founders Lightning Round Where to find Krepling and Liam Resources Full show notes: https://saasclub.io/295 Join 5,000+ SaaS founders: https://saasclub.io/email

Ryan Fyfe couldn't get 10 customers to pay for his scheduling software. People seemed interested but always had an excuse. Then his co-founder left and he became a solo founder of a product that nobody wanted to pay for. Getting startup traction felt impossible. But after years of persistence, Ryan bootstrapped Humanity to $100K ARR, raised funding, and grew it to $12M ARR with 40,000 customers including Nike, CNN, and Lyft. In this episode, Ryan shares the startup traction playbook he wishes he had - from launching free to get early traction, to SEO and review sites as growth engines, to the pricing mistake that cost him five years of revenue. Ryan's getting traction journey proves that initial traction comes from launching free online rather than in-person pilots. His biggest regret: 70% of Humanity's customers generated only 10% of revenue because he lacked the confidence to charge more for five years. Key Lessons 🎯 Launch free online to find startup traction instead of in-person pilots: Ryan spent months on local business pilots that went nowhere. Launching a free version online attracted passionate early adopters who actually used the product and provided feedback. 💰 Segment customers before pricing costs you five years: 70% of Humanity's customers generated just 10% of revenue. A quad system ranking customers by size and expansion potential let them focus resources on profitable segments. 🚀 SaaS review sites compound startup traction when you start early: Ryan listed Humanity on G2, Capterra, and GetApp when those sites were just starting. Being early on review platforms created a ranking advantage that compounded as those sites grew. 📉 Price confidence matters more than price level for startup traction: Ryan always positioned Humanity as the cheapest option out of insecurity. When they finally raised prices, revenue grew faster because they attracted serious buyers. 🧠 Know when you're a builder, not an operator: Ryan realized he disengaged when working through management layers and was too slow to hire executives. Handing the CEO role to someone better suited let the company thrive. Chapters Introduction Ryan's quote: "When you're backed against the wall, break it down" What Humanity does: employee scheduling software SaaS in 2009: no tool stack, no smartphones, no cloud adoption How the idea came from working hourly shifts Building the product himself with no technical co-founder Validation: trusting his gut instead of customer interviews Co-founder fallout and becoming a solo founder The demoralizing period: can't get 10 customers Launching free online and finding startup traction Building feedback loops through customer forums Solo founder: hiring remote support as first employees Bootstrapping to first few hundred customers Raising a seed round after an investor found them through reviews Growing to $10M ARR and handing off the CEO role Growth channels: SEO, content marketing, review sites Launching paid plans: the pricing confidence problem Customer segmentation: the 70/10 discovery Self-awareness: knowing you're a builder, not an operator Weekly journaling framework for founders The Humanity acquisition during COVID Joining Workpuls as co-founder and COO Lightning round Resources Full show notes: https://saasclub.io/294 Join 5,000+ SaaS founders: https://saasclub.io/email

Iris Shoor got her first customer 30 minutes after turning on Facebook ads - for less than $50. The product was clearly working. Then she killed it. She shut down a product with real users, real engagement, and real validation because investors told her Facebook would build it themselves. In this episode, Iris reveals the SaaS pricing journey that took Oribi from free to $79 to $500 per month, why charging more actually improved retention, and how she grew the company to 60 employees and $28 million in funding by competing against free Google Analytics. Her pricing strategy evolved through painful lessons about pricing optimization. Oribi founder Iris Shoor raised SaaS pricing from $79 to $500/month and discovered that customers with real marketing budgets invested more in the product, extracted more value, and churned less. Her pricing model proved that competing against free requires demonstrating clear ROI, not matching their price. Key Lessons 💰 Higher SaaS pricing improves retention, not just revenue: Oribi raised prices from $79 to $500/month and found that higher-paying customers engaged more deeply, extracted more value, and churned less because they had real budgets to invest in the product. 📉 Never kill a working product based on investor concerns alone: Iris shut down a validated Facebook analytics tool because investors warned Facebook would build it. Four years later nothing changed, and she lost years of compounding growth. 🎯 Vertical packaging boosts conversion before vertical features: Oribi created separate landing pages and onboarding flows for e-commerce and agencies with vertical-specific terminology. Conversion rates jumped even before adding vertical-specific product features. 🧠 Create a wish list of experts, not a convenience list of contacts: Instead of asking friends for feedback, Iris reaches out to specific experts on LinkedIn with precise questions - getting 80% reply rates by being relevant and specific. 🚀 Facebook ads work for B2B SaaS pricing validation: Iris acquired Oribi's first customer in 30 minutes through Facebook ads. B2B founders who dismiss Facebook as "B2C only" miss that decision-makers use Facebook too. Chapters Introduction What inspires Iris: building things and solving challenges What Oribi does: no-code marketing analytics Target customers: mid-sized companies with marketing budgets Business size: 60 employees, thousands of customers, $28M raised Background: architecture to Autodesk acquisition to OverOps How the analytics idea came from marketing pain Building a wish list of dream advisors Reaching out to ex-Google Analytics PMs on LinkedIn The key question: if this is painful, why is nobody solving it? First product: Facebook analytics tool First customer in 30 minutes through $50 in Facebook ads Killing the product after negative investor feedback Starting over: building codeless data collection from scratch Getting first customers through Facebook ads Why Facebook ads work for B2B SaaS Building lookalike audiences with gated content at $1-2 per lead SaaS pricing evolution: free to $79 to $300 to $500/month Why starting free before a fundraise can be strategic Competing against free Google Analytics Vertical packaging: e-commerce, agencies, SaaS Lightning round Resources Full show notes: https://saasclub.io/293 Join 5,000+ SaaS founders: https://saasclub.io/email

Zandra Moore and her co-founders carried a server across a car park to start their company. Then they wrote 500 handwritten letters to software vendors - because in a market dominated by Tableau and Power BI, their SaaS sales strategy meant doing things nobody else would. In this episode, Zandra reveals how Panintelligence grew into a multiple 7-figure SaaS business with 50+ employees by embedding white-labeled analytics inside other SaaS products. Their competitive differentiation comes from querying data where it already lives instead of moving it. Zandra's SaaS sales strategy combines creative outbound with sharp SaaS differentiation. From handwritten letters to fish-and-chip demos to LinkedIn messages citing podcast quotes, Zandra proves that standing out in SaaS requires a sales approach as distinctive as your product. Her SaaS sales strategy narrowed from "all software vendors" to four verticals on AWS using the Crossing the Chasm framework. Key Lessons 🎯 Build competitive differentiation by solving what giants ignore: Power BI and Tableau move data and serve end users directly. Panintelligence found their niche by querying data in place and white-labeling for SaaS vendors - a use case the big players overlooked. 🤝 Handwritten outreach creates a SaaS sales strategy that gets attention: Zandra sent 500 personalized letters because email was too noisy. Doing things that don't scale - fish-and-chip demos, hand-signed letters - got attention when automation couldn't. 📉 "All software vendors" is still too broad an ICP: Even after choosing to sell only to software vendors, Panintelligence needed to narrow further. The Crossing the Chasm framework helped focus on four verticals with existing references. 🔄 Reseller channels drain resources without clear SaaS sales strategy: Resellers needed heavy enablement and lacked technical depth. Direct relationships with SaaS vendors who embed the product proved far more sustainable. 💰 Personalization scales better than you think: From handwritten letters to LinkedIn messages citing specific podcast quotes, personalized outreach consistently converts at much higher rates than automated campaigns - even at 50+ employees. Chapters Introduction Zandra's quote: Givers gain What Panintelligence does: embedded white-label BI for SaaS Customer examples: ACI Worldwide, schools, healthcare The broad market challenge: analytics for everyone Origin story: spinning out from Pancredit What "spinning out" actually looked like Carrying a server across a car park First three months: 500 handwritten letters Why send letters instead of emails What the letters said: personalization approach The lesson: do things others aren't doing Narrowing the ICP with a SaaS sales strategy Expanding from UK to international markets Using LinkedIn and content marketing for outreach Following up 12 times without being annoying AWS partnership and marketplace learnings Competing against Tableau and Power BI Why data-in-place is the key differentiator Building ML-powered predictive analytics Lightning round Resources Full show notes: https://saasclub.io/292 Join 5,000+ SaaS founders: https://saasclub.io/email

Esben Friis-Jensen went from co-founding a VC-backed security company with 200 employees and $37 million in funding to a bootstrapped product-led growth startup with just two people - and nearly $1M in annual recurring revenue. In this episode, Esben reveals how a single customer request triggered Cobalt's pivot from bug bounty to pen testing, why he chose to bootstrap Userflow after years in the VC world, and how product-led growth can sell a SaaS onboarding tool without a sales team. Userflow's self-serve SaaS approach means many customers complete a free trial and purchase without a single conversation. Esben's PLG strategy is built on exceptional UX and treating every support ticket as a product improvement opportunity. This product-led growth mindset lets 2 people serve hundreds of paying customers without dedicated support staff. Key Lessons 🔄 A single customer request can reveal product-led growth potential: Cobalt's pivot started when one customer asked for a pen test and paid $8,000 - proving the market wanted a different product than what was being built. 💰 Subscription beats transactional pricing for SaaS onboarding: Cobalt moved from per-bounty fees to annual pen testing subscriptions, transforming unpredictable revenue into recurring ARR that the team could plan around. 🛠️ Solve support tickets in the product, not in help docs: Userflow treats every support request as a product-led growth improvement opportunity, which is why 2 people can serve hundreds of customers without dedicated support staff. 🎯 Disincentivize enterprise to keep product-led growth operations lean: Userflow deliberately pushes mid-market buyers toward self-serve credit card plans, reserving enterprise procurement only for truly large companies. 🚀 UX is more important than features for product-led growth: Userflow wins by being advanced yet easy to use. Competitors cluster into simple-but-basic or powerful-but-complex - the middle ground is underserved. Chapters Introduction Esben's favorite quote: Quality at Speed What Userflow does: no-code SaaS onboarding Revenue: closing in on $1M ARR with 2 people What is Cobalt and pen testing as a service How 4 Danish founders with no security experience started Cobalt Building the MVP in Buenos Aires and joining Boost VC First year challenges and early bitcoin exchange customers The pivot: from bug bounty to pen testing Running out of money and the eureka moment The transition period and why dual marketing failed Moving from transactional to subscription pricing Selling pen testing against consulting incumbents Transitioning from sales-led to product-led growth at Cobalt Breaking into the close-knit US security community How Esben and Sebastian connected and started Userflow Going full circle: from sales-led back to product-led growth How customers buy without speaking to anyone Userflow's differentiation: advanced yet easy to use Building great UX and the importance of less is more Using Userflow for Userflow (meta onboarding) Growth channels: SEO, Google Ads, thought leadership, word of mouth How 2 people do everything: the power of product-led growth Customer mix: SMB majority with some enterprise Disincentivizing enterprise procurement Lightning round Resources Full show notes: https://saasclub.io/291 Join 5,000+ SaaS founders: https://saasclub.io/email

Steve Carroll sent his co-founder into New York bars to ask strangers how they paid their rent. Some women thought it was a pickup line - until they saw the Typeform survey. That scrappy approach got them 1,000 survey results and enough conviction to build a niche SaaS product for the rental market. In this episode, Steve reveals how Findigs pivoted from a consumer rent payments app to a B2B niche SaaS leasing platform after brand partners kept asking for access to renters at the point of move-in. That shift to vertical SaaS, combined with an ML-powered tenant screening engine, helped Findigs reach $2M ARR with just 12 people serving 60,000 units. Carroll's journey from consumer payments to industry-specific SaaS proves that the best niche SaaS ideas come from listening to adjacent stakeholders, not just your core users. Findigs differentiated in a crowded vertical software market by integrating alongside existing tools instead of replacing them. Key Lessons 🎯 Validate with niche SaaS customers, not just users: Carroll's bar surveys showed consumer demand, but the real business insight came from calling landlords already receiving Findigs payments - revealing the leasing pain point that became their core product. 📉 Onboarding mismatches kill niche SaaS retention: Findigs signed diverse customer profiles before supporting their workflows, creating manual workarounds that end users resented - proving that decision-maker enthusiasm does not equal user adoption. 🔄 Listen to adjacent stakeholders for pivot signals: Brand partners told Carroll renters are most valuable at move-in, not after. That feedback from outside the core user base triggered the pivot from payments to leasing. 🤝 Warm outbound beats cold outbound in niche SaaS sales: Findigs' first B2B customers were landlords they already paid rent to, turning cold calls into warm conversations with a built-in touchpoint. 🛠️ Avoid rip-and-replace to shorten sales cycles: Findigs integrates alongside existing software instead of replacing it, reducing sales cycles from months to weeks - critical in a market with entrenched incumbents. Chapters Introduction Steve's background on Wall Street and restaurant tech What Findigs does and the problem it solves Business size: $2M ARR, 12 people, 60,000 units How the idea came from renting in New York City Starting with rent payments as the first product Getting started with funding from a Wall Street contact Bar surveys: collecting 1,000 results in New York How Keith met his girlfriend doing customer research Shipping the first product in five months Getting 400 payments in the first month with no marketing Why the service was free and 75% of users tipped Pivoting to B2B niche SaaS after brand partner feedback Understanding the leasing pain point for landlords Six months of research before building the new product Early product mistakes: shipping before workflows were ready Getting attention in a crowded market Outbound sales: posing as renters to find leads Differentiating with ML-powered underwriting Usage-based pricing model Sales cycle measured in weeks, not months Lightning round Resources Full show notes: https://saasclub.io/290 Join 5,000+ SaaS founders: https://saasclub.io/email