The SaaS Podcast - Growing Profitable AI SaaS & AI Agents

Five years at $50K ARR. Ten failed projects. Lending the business money out of his own bank account. George Georgiadis came close to shutting Happier Leads down. Instead he broke through the revenue plateau and reached $1.5M ARR with zero employees. George explains what moved the number: an end-to-end platform instead of a narrow point tool, cold email as his cheapest channel because he owns the mailboxes and the data, and running a SaaS with AI agents he built himself to handle support and bug fixing around the clock. Plus: why he turned down a $1M offer to sell, and why he is hiring again after reaching seven figures alone. Happier Leads identifies anonymous website visitors, qualifies them with AI, and engages them by email. George Georgiadis bootstrapped it from a $50,000 AppSumo campaign to $1.5M ARR with no outside capital. This episode is brought to you by: 🍎 Product Fruits → Book a demo tailored to your product 🔑 Key Lessons 📉 A plateau is a depth problem, not an effort problem: George wore every hat for five years at $50K ARR and never went deep enough on one channel to make the unit economics work. 💰 Own the infrastructure your channel depends on: Building his own mailboxes and using the 175-million-contact database he already owned pushed cold email costs low enough to send millions profitably. 🎯 The point tool that felt like a mistake became the moat: Building identification, qualification, enrichment, and email sending into one platform took seven years, but no competitor covers the full path. 🤝 Cold email works on precision, not personalization theater: He picks the exact company and job title, keeps the message short, and withholds links until the prospect replies to protect deliverability. 🛠️ AI replaces a team only when the data lives in one place: Ripping out HubSpot, Intercom, and Pipedrive for self-built tools gave his AI brain the visibility it needs to fix bugs unattended. 🚀 Lifetime deals buy time, not revenue: The $50,000 AppSumo campaign got consumed by server and data costs within two years, but the reviews, word of mouth, and runway were worth more. 🧠 A solo operator owns a job, not a company: Even at $1.5M ARR with AI doing the heavy lifting, George is hiring because a business that stops when he stops cannot be sold. Chapters Cold open: five years stuck, then $1.5M What Happier Leads does $1.5M ARR with zero employees, bootstrapped From Greece to London and 10 failed projects Where the Happier Leads idea came from Clearbit quoted $20,000 so he built his own Funding the product with AppSumo lifetime deals Buying the data, building the business on top The real cost and hidden upside of lifetime deals Five years stuck at $50K ARR 80% development, 20% marketing and sales Building end to end instead of a point tool Nearly quitting and lending the business his own money What finally changed: going deep on unit economics Cold email becomes the main acquisition channel What makes cold email work at scale Running the business with self-built AI agents Self-healing software and KPI monitoring Why he's hiring again after zero employees Lightning round Resources Full show notes: https://saasclub.io/489 Join 5,000+ SaaS founders: https://saasclub.io/email

George Georgiadis

Founder and CEO

Happierleads

Ron Hash bootstrapped Skimmer, software for pool service companies, to over $1 million in ARR and 1,500 customers with zero paid marketing, then sold it. His SaaS pricing was the engine: 50 cents per serviced pool with a $29 minimum, when every competitor charged per seat. Ron shares how he validated the idea with one cold call, why his SaaS pricing aligned revenue with each customer's growth, how he cut churn from 6% to 2% by fixing onboarding, and why he never regretted the exit. His SaaS pricing chose a value metric close to the money instead of per-seat pricing, which made adding customers feel good and kept churn low. Ron Hash built Skimmer with no prior SaaS experience and got it to 1,500 customers on SEO and word of mouth alone. That SaaS pricing model kept churn low and made the business acquirable; he sold to Unbundled Capital in 2020, after which the company raised $79 million and grew past 100 employees. He is now building QuickFax. This episode is brought to you by: 🍎 Product Fruits → Book a demo tailored to your product 🔑 Key Lessons 💰 Usage-based SaaS pricing aligns revenue with customer success: Skimmer charged 50 cents per serviced pool, so a customer's bill rose only as their business grew, making them happy to pay more. 📉 Per-seat SaaS pricing punishes growth and drives churn: Ron priced on serviced pools instead of seats, so customers never hesitated to add users and the product became stickier across the whole team. 🎯 Validate with one real conversation, not a survey: Ron cold-called a single pool pro who said "the paper game is killing me," and that one honest answer was enough proof the problem was real. 🚀 SEO plus word of mouth can replace an ad budget: Ranking for "pool service software" and delighting customers got Skimmer to 1,500 users with zero paid marketing. 🔄 Churn is usually an onboarding problem: Ron cut churn from 6% to 2% with a simple onboarding flow that pulled new users to their first win, not by adding features. 🛠️ Build for the user doing the work: A fast, low-tap, offline-capable mobile app for field techs beat the web-based tools competitors built for office staff. Chapters 00:00 50 cents a pool 00:30 Introduction 01:46 What Skimmer is and who it's for 03:46 Where the idea came from 07:05 Going all in on nights and weekends 08:16 Deciding what to build first 08:53 Welcome calls and learning from customers 11:36 The first customer and teaching himself SEO 13:32 Inbound vs the people he cold-called 15:00 The long slow ramp to 76 customers 16:39 Pricing at 50 cents a pool, not per seat 20:32 Explaining usage-based pricing to customers 22:41 Pen and paper vs software 25:19 Why Skimmer got so much traction 31:00 Cutting churn from 6% to 2% 36:25 The hard days of bootstrapping 39:17 Selling Skimmer 43:26 No regrets on the exit 44:53 QuickFax, his new project 47:56 The biggest lesson: solve small problems 49:35 Lightning round Resources Full show notes: https://saasclub.io/488 Join 5,000+ SaaS founders: https://saasclub.io/email

Ron Hash

Skimmer

Six years of grinding, and SaaS churn kept capping his growth: win a customer, lose a customer, repeat. Then one pricing call flipped everything. Farzad Rashidi pivoted Respona to a done-for-you service-as-software model and 4x'd in twelve months the revenue it took six years to build. Farzad shares why adding features never fixed his SaaS churn, the agency CEO haggle that sparked the pivot, how he demoted his own SaaS on the homepage to lead with the service, and how he rebuilt a software layer on top so the business could scale. Respona helps brands get cited in AI answers across ChatGPT, Perplexity, and Google AI Overviews. Farzad first appeared in episode 323 as a self-serve outreach tool doing a few hundred thousand in ARR, before SaaS churn stalled it; today the first done-for-you customer alone spends around $65K to $70K a month. This episode is brought to you by: 🍎 Product Fruits → Book a demo tailored to your product 🔑 Key Lessons 🔄 Service-as-software beats pure SaaS when usage drives SaaS churn: Respona's customers canceled because they had no time to use the tool, not because it lacked features, so doing the work for them removed the real reason for churn. 💰 Price on outcomes, not subscriptions: When Farzad shifted from an $800 monthly license to paying per result, the same customer who haggled over $300 immediately committed to $7K to $8K a month, then scaled to $65K. 📉 A plateau is a signal to change the model, not add features: For years Respona feature-slapped the product to fight SaaS churn and stayed stuck; growth only came after they changed the business model, not the feature set. 🛠️ Build the software layer back on top of a service-as-software model: After delivering manually off a Google Sheet, Respona rebuilt a client portal, publisher network, and a back-end brain so the service could scale like software. 🎯 Productize the service so it moves on an assembly line: Respona set five fixed tiers, volume-based discounts, and paid add-ons, avoiding the custom-call trap that makes traditional agencies impossible to scale. 🚀 Off-page SEO is making a comeback for AI visibility: To get cited in AI answers, Respona finds lookalike publishers, publishes fresher skyscraper content, and builds a surround-sound presence so the models repeatedly encounter the brand. Chapters 00:00 The call that changed everything 00:30 Introduction 01:18 What Respona does today 02:48 Respona's origins and the first interview 04:13 Early traction, then the SaaS churn plateau 06:20 Stuck feature-slapping the product 08:07 The pivotal customer call in early 2025 10:52 Why going into services felt like the cardinal sin 11:50 How AI changed the services math 14:20 Delivering the first service off a Google Sheet 14:54 Testing demand and finding product-market fit 19:18 Rebuilding a software layer on top 22:13 Service-as-software and the YC and Sequoia thesis 27:59 Productizing the service with fixed tiers 31:27 How AI answers get generated (the Notion example) 37:14 Finding lookalike publishers and fresher content 43:12 Surround sound and the Opus Clip case study 45:06 Is SEO dead and the truth about Reddit 50:54 Lightning round Resources Full show notes: https://saasclub.io/487 Join 5,000+ SaaS founders: https://saasclub.io/email

Farzad Rashidi

Co-Founder

ResponaVisme

Danny Jenkins was $150,000 in credit card debt with zero paying customers 18 months into building his bootstrapped startup. An accelerator told him to quit. He ignored the advice and built ThreatLocker into a cybersecurity company approaching $200M in revenue. In this episode, Danny Jenkins shares how he grew a bootstrapped startup from $150K in debt to nearly $200M in revenue. You'll hear how he turned a tiny market into a $10 billion category, why he was shaking when he asked for his first sale, and how a bootstrapped startup can win against an entire industry. ThreatLocker now protects 70,000 companies worldwide. Danny explains the zero trust approach behind the bootstrapped startup, how MSPs became his distribution wedge into small business, and the founder mindset that carried his self-funded company through near-bankruptcy. It is a candid look at bootstrapping a profitable company without losing your nerve. 🔑 Key Lessons Create a new category instead of fighting for a small market For a bootstrapped startup, sales is asking for the order, not a magic pitch Money changes your problems, it does not solve them Use MSPs as a distribution wedge into small business A real product and buyers knowing it exists are the only things that matter early Chapters 00:00 Introduction 01:04 What ThreatLocker does 01:56 Danny's background in cybersecurity 05:15 The ransomware recovery that sparked the idea 08:00 WannaCry and creating a category 10:02 The 18-month grind to the first customer 13:12 Shaking to ask for the first sale 16:03 Surviving debt, a hurricane, and near-bankruptcy 21:15 The founder mindset that kept the bootstrapped startup alive 23:00 The only two things that matter early 24:56 Hiring the right salesperson 30:02 Trade shows, COVID, and scaling 35:30 MSPs as a distribution wedge 38:27 The Kaseya attack and overnight growth 41:12 Why zero trust is controversial 45:39 Lightning round Resources Full show notes: saasclub.io/486 Join 5,000+ SaaS founders and get the best SaaS content every week: saasclub.io/email ThreatLocker: threatlocker.com Danny Jenkins on LinkedIn: linkedin.com/in/dannyjenkins

Danny Jenkins

ThreatLocker

He wrote the startup playbook. Then he watched founders who used it lose control of what they built. Eric Ries, author of The Lean Startup, felt like he was feeding companies into a meat grinder. Founders will hear his startup governance framework, why most lose founder control after product-market fit, and the two-page filing that protects them. Eric breaks down what happens when one customer becomes half your revenue, how to tell real product-market fit from slow drift, and why the term-sheet paperwork your lawyer hands you is quietly working against you. He shares the Twilio case where Jeff Lawson was removed by activists 199 days after his seven-year dual-class sunset expired, and a Harvard Law School study showing only 20% of venture-backed founder CEOs are still CEO three years after IPO. Plus: why Vectura's board sold an inhaler company to Philip Morris for an extra 10 pence per share, and what that says about every startup governance choice founders face today. Eric Ries authored The Lean Startup and the new book Incorruptible on startup governance. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🔑 Key Lessons 🧠 Startup governance erodes through drift, not attack: Founders lose companies through quiet roadmap drift, board concessions and term-sheet defaults, not one dramatic event. 🎯 Real product-market fit feels like a tornado: If you have time to call an advisor and ask whether you have product-market fit, you do not. Real PMF means drowning in demand. 📉 One big customer can hijack your roadmap: A SaaS founder Eric advised landed a whale, and the product drifted within six months around what that customer "might" want. 🏢 The two-page filing that protects founder control: A Delaware C-corp can convert to a Public Benefit Corporation in five minutes, writing the mission into the charter before investors push back. 💰 "Any lawful purpose" is not neutral: Delaware courts read it as a fiduciary duty to maximise shareholder value, which is how Vectura sold to Philip Morris for 10 extra pence per share. 🤝 Decide who you would rather die than betray: Customers, employees or shareholders. Whoever you put first becomes the test for every startup governance decision. 🚀 Build the startup governance fortress before you need it: Protective provisions and charter purpose are easiest to install when you have five people and no investors on the cap table. Chapters What would Eric Ries change about The Lean Startup today Why AI makes building cheaper but learning the real bottleneck The meat-grinder problem that led to Incorruptible Jeff Lawson, Twilio and the 199-day post-IPO ouster The LTSE bathroom floor and the capitulate-or-die ultimatum Financial gravity, explained One customer hits 50% of revenue: what happens next Product-market fit vs slow drift Why startup governance matters at five people The Public Benefit Corporation conversion in two pages The Philip Morris thought experiment The real Vectura sale and the 10-pence betrayal OpenAI, structural integrity and the limits of paper governance The 5-minute filing a founder can do this week Lightning round and where to find Eric Resources Full show notes: https://saasclub.io/485 Join 5,000+ SaaS founders: https://saasclub.io/email

Eric Ries

Founder & CEO

Long-Term Stock ExchangeLTSEThe Lean Startup

He talked openly about his startup idea. A competitor took it and beat him to market. Mark Abbott shared his SaaS vision inside a tight-knit coaching community. A member passed it to a client who launched first. Founders will hear how Mark recovered with community-led SaaS growth and built Ninety to $44M ARR and 18,500 customers. Mark explains why he spent 4 years on B2B community building before writing code, how community-led SaaS growth plus $500 a month on Facebook ads got his first 1,000 customers, and why bootstrapping past a $100M valuation set up the dilution math he wanted before a $20M Series A. Plus: how Mark protected the community-led SaaS growth playbook after the Series A and why hiring seasoned executives created what he calls "the mess." Ninety raised $55M from Insight Partners, Blue Cloud Ventures, and Catalyst Ventures, and serves 18,500 companies covering close to 1 million employees. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🔑 Key Lessons 🤝 Community-led SaaS growth beats speed: 4 years as EOS implementer #33 before writing code. The community trust Mark banked became his distribution channel, investor base, and product council. 📉 Sharing your idea openly carries real risk: Mark talked about his SaaS vision inside the EOS community. An implementer passed it to a client who built Traction Tools and beat Ninety to market. 🎯 Bootstrap until the dilution math works for you: Mark hit a $100M+ valuation before raising. His $20M Series A from Insight Partners diluted him about 17%, leaving him majority owner after Series B. 💰 A tiny ad budget can scale further than you think: $500 a month on Facebook ads layered on top of the coaching channel got Ninety to 1,000+ customers. 🏢 Executives arrive with their own playbooks - hire for your stage: Mark hired fast after the Series A. Senior leaders brought conflicting paces - he calls it "the mess." 🚀 Community-led SaaS growth compounds: Bootstrapped SaaS founders who run on channel-led growth build moats that compound. Ninety now layers AI on top of 10 years of EOS coach relationships. 🧠 Long-term product vision beats agile dogma: Mark spent 6 months on data schema before shipping. The five EOS tools shipped first, AI was on the roadmap from 2012, and conviction is paying off. Chapters The competitor who beat him to market What Ninety does and who it serves The 2005 idea and the EOS connection Pitching Gino Wickman: "It's not in our DNA" 4 years inside the EOS community before code A competitor steals the vision: Traction Tools Did getting copied change what he shares? Building the first product under license restrictions Designing for the long game: data schema first The size of Ninety today: $44M, 18,500 companies Pricing at $12 per seat and where AI changes it Selling through the coaching channel $500/month on Facebook plus community-led SaaS growth Bootstrapping toward a $100M valuation What changed after the $20M Series A The hidden cost of hiring fast AI strategy, embedded vs native, and the moat Lightning round and closing Resources Full show notes: https://saasclub.io/484 Join 5,000+ SaaS founders: https://saasclub.io/email

Mark Abbott

Founder

Ninety

Two years on Quora and Reddit. Zero customers. Yega Kumarappan and his two co-founders had no sales experience. They bet that founder-led sales could beat the B2B sales playbook. Founders will hear how Paperflite grew from a 400K seed to 500 B2B customers and seven figures in ARR while selling SaaS without sales experience. Yega shares the founder-led sales process that took conversion from 2-3% to 17-20%, why he spent 8 to 10 hours setting up a custom demo for every startup sales prospect, and how the team built qualified inbound from Quora and Reddit in their first two years. He also breaks down why Paperflite never raised after the seed and how he competes against the Seismic-Highspot merger. Plus: the Fortune 500 deal that almost died in their Intercom inbox because the team thought it was a prank, and the founder-led sales tactics that produced 26 enterprise customers in year one. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🔑 Key Lessons 🎯 Founder-led sales starts on forums, not LinkedIn: Yega's team spent two years answering Quora and Reddit questions to build qualified inbound, then converted forum readers via LinkedIn DMs and Intercom. 💰 10-hour custom demos beat generic product tours: Pre-building each prospect's actual Paperflite hub (their content, regions, buyer segments) pushed conversion from 2-3% to 17-20%, validated through A/B testing. 🤝 High-touch onboarding is leverage in founder-led sales: Paperflite manually pulled content from SharePoint and shared drives for the first 50 to 70 customers to lock in retention and learn each industry. 🚀 Profitability buys product freedom: A single 400K seed plus year-two profitability let Paperflite rebuild coaching as AI-native and content creation as Canva-like without VC-led roadmap pressure. 🏢 Position between giants and AI point solutions: Seismic-Highspot consolidation creates one big target above and AI-only entrants leave gaps below - mid-tier with deep industry context wins the middle. 📉 Verbal commitments don't predict conversion: Marketing leaders told Paperflite "we love this, we'll buy it" in validation calls and then didn't - rely on the conversations to learn, not the commitments. 🛠️ Run A/B tests on your B2B sales process, not just your product: Paperflite split prospects into self-serve vs we set it up for you cohorts and used the conversion gap (2-3% vs 17-20%) to commit to high-touch demos permanently. Chapters What Paperflite does and the size of the business Origin story at Cognizant and the content distribution problem Leaving stable jobs to start Paperflite Raising the 400K seed in 2018 Validating the prototype with CMOs who didn't buy The Netflix experience for sales content Finding the first customer through Intercom The S&P Global Fortune 500 deal that looked like a prank Two years on Quora and Reddit to build inbound Founder-led sales without self-serve onboarding The 8 to 10 hour custom demo playbook A/B testing demos: 2-3% vs 17-20% conversion Why Paperflite never raised again after seed Competing with the Seismic-Highspot merger Positioning the mid-tier sweet spot Lightning round Resources Full show notes: https://saasclub.io/483 Join 5,000+ SaaS founders: https://saasclub.io/email

Yega Kumarappan

Co-Founder

Paperflite

Two failed startups. 250K euros in debt. Stuck in Paris with a sick baby and no plan. Tibo Louis-Lucas walked away from a stable CTO job and shipped 11 products in 4 months on unemployment benefits. Today TMAKER is a bootstrapped SaaS startup portfolio doing $1M a month across 5 products with a team of 10. Tibo breaks down the exact signal that told him Tweet Hunter was the one after 10 failures, the JK Molina equity deal that took it from $3K to $20K MRR in 3 weeks, why he regrets selling Tweet Hunter and Taplio for $8 million, and the co-maker model that powers his bootstrapped SaaS startup today. Plus: why Tibo says SEO is the most durable distribution channel for a bootstrapped SaaS startup, even as LLMs reshape search. TMAKER is a bootstrapped SaaS startup studio of 5 products. Outrank crossed $200K MRR. Revid does over $600K a month. The portfolio crossed $1M a month a few weeks before this conversation. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🔍 Respona → Get featured in AI answers on ChatGPT and Google AI Overviews 🔑 Key Lessons 🚀 Distribution is the reusable bootstrapped SaaS startup asset: Tibo built one SEO playbook, one ads pipeline, and one influencer network and reuses them across all 5 TMAKER products. Each new product launches with traffic from day one. 🎯 Validate with revenue, not downloads: Tibo shipped 11 products in 4 months and only kept the one that pulled paying customers. Recurring revenue past month two is the only signal he trusts. 🤝 Equity beats commission for distribution partners: JK Molina got 25% of profits and exit proceeds tied to active work. That tripled Tweet Hunter revenue from $3K to $20K MRR in three weeks. 💰 An earnout can sell you the company twice: Tibo took $2M upfront and earned $8M total against $8M ARR. He calls it selling an $8M business for $8M, and the post-exit void hit harder than the payday felt good. 🛠️ Switch from maker to distribution as you scale: Tibo flipped from builder to distribution operator and partners with co-makers. One distribution operator can power a 5-product bootstrapped SaaS startup that 5 solo founders could not. 🧠 Real PMF is when demand outruns you: Tweet Hunter PMF showed up as overwhelming DMs, feature requests, and signups he could not keep up with. Comfortable growth is not the signal - chaos is. ⚡ AI makes building cheap, so distribution is the moat: Outrank, Revid, and TMAKER survive copycats by owning audience, SEO real estate, and partner networks that compound long after the code ships. Chapters What TMAKER does today Crossing $1M monthly across a bootstrapped SaaS startup portfolio Two failed VC startups and 250K euros in debt Sick baby, COVID, stuck in Paris Shipping 11 products in 4 months Why Tweet Hunter felt different The JK Molina 25 percent equity deal Launching Taplio for LinkedIn Selling to Lempire for $8M and why he regrets it The co-maker model explained SEO as the most durable distribution channel Lightning round Resources Full show notes: https://saasclub.io/482 Join 5,000+ SaaS founders: https://saasclub.io/email

Tibo Louis-Lucas

Co-Founder

TMAKER

Hadn't coded in four years. No team. No idea. Marius Meiners launched his AI startup, Peec AI, with a V0 prototype built in 1.5 days and 8 letters of intent. 14 months later: $8.6M ARR, 55 employees, and a competitor with 5x his funding chasing enterprise. Marius shows how to validate an AI startup before coding, win the mid-market while competitors chase enterprise, and price your AI startup at €85 a month against incumbents charging €500+. He breaks down the V0 build, the LOI playbook, and how 20% of conversions now come from AI search itself. Peec AI is an AI startup that launched in February 2025 from Antler's Berlin cohort. Marius previously transitioned from professional esports through software engineering and venture capital at PwC. This episode is brought to you by: 🔍 Respona → Get featured in AI answers on ChatGPT and Google AI Overviews 🔑 Key Lessons 🚀 Use AI to compress validation timelines: Marius built the Peec AI MVP with V0 in 1.5 days and signed 8 letters of intent before writing production code. Modern AI tools turn idea-to-validation from months to days. 💰 Mid-market pricing wins when competitors fight enterprise: Peec priced at €85 a month while competitors charged €500+. AI search optimization at the mid-market price point captured 2,000 customers competitors ignored. 🎯 Letters of intent beat verbal validation: Asking "would you sign an LOI?" filters out polite enthusiasm. Marius signed 8 LOIs from a V0 prototype - real signal that the AI startup problem was acute enough to pay for. ⚡ Speed is the moat for AI-era SaaS: Idea in October 2024, launch in February 2025, $8.6M ARR by April 2026. In emerging categories, the founder who ships weekly outpaces the founder who polishes. 🧠 Scrappiness has a shelf life: Eating €2 canned food works at zero revenue. At $8.6M ARR with 55 employees, scrappiness becomes a bottleneck. Most founders break their company by clinging to it past its expiration date. 🚀 Build with AI search optimization in mind from day one: 20% of Peec's new conversions now come from AI search itself. Founders who do not structure content for AI assistants are leaving meaningful pipeline on the table. Chapters What Peec AI does From esports to PwC to startups ChatGPT search and the aha moment for an AI startup Validating ideas in days, not months Knowing AI search optimization was the bet How AI search optimization actually works Free GEO tactics for founders without budget Building the V0 prototype in 1.5 days Getting the first 8 letters of intent The pitch that won early adopters Advice for founders chasing early traction Pricing at €85 vs competitors at €500+ Scaling from LOIs to $8.6M ARR Lightning round Where to find Peec AI Resources Full show notes: https://saasclub.io/481 Join 5,000+ SaaS founders: https://saasclub.io/email

Marius Meiners

Founder

Peec AI

He built a free tool as a lead magnet. Then customers started calling his cell phone, begging to pay for it. Ev Kontsevoy turned an open source SaaS side project into Teleport, now an 8-figure ARR business with 500+ customers. Founders will hear how a free GitHub project became an open source SaaS business worth eight figures - and why selling to the wrong buyer persona nearly capped growth. Ev reveals how he spotted the signal that his side project was more valuable than his flagship product, why shifting from engineers to VP buyers nearly tripled average deal size, and how open source monetization built trust closed-source competitors could never match. Teleport started as one component of Gravity, which was doing $4M ARR. COVID killed Gravity's pipeline while accelerating Teleport demand. The company now serves 500+ customers in 8-figure ARR, with AI agent identity emerging as a major growth driver. This episode is brought to you by: 🌎 ThreatLocker → Book a demo 🔍 Respona → Get featured in AI answers on ChatGPT and Google AI Overviews 🔑 Key Lessons 🛠️ Your open source SaaS lead magnet might be your real product: Teleport was built as free demand generation for Gravity, but customers wanted to pay for it instead - listen when the market tells you where the value is. 🎯 Ask customers to sell your product back to you: Ev discovered most customers used a tiny fraction of Teleport by asking them to describe it, revealing a buyer persona mismatch that was capping growth. 🤝 Match your sales motion to your buyer's expectations: Shifting from engineers to VPs of platform engineering nearly tripled average deal size because the new buyer expected a sales-led conversation. 🔄 Focus is not a pivot - it is subtraction: Ev stopped four of five things Gravitational was doing and concentrated entirely on Teleport, which was already generating equal revenue with fewer engineers. 💰 Price with confidence even when improvising: The first Teleport enterprise deal closed at $25,000/year because Ev said "thousand" instead of "hundred" on a cold call - then built the enterprise product around real customer requests. 🚀 Open source SaaS builds trust faster for security products: Public code audits and community reviews gave Teleport credibility closed-source competitors could not match - a natural open source lead generation advantage. 🧠 Find startup ideas in the support queue: Ev found both Mailgun and Gravitational by listening to customer problems at his day job. This open source business model started from real pain, not brainstorming. Chapters What Teleport does and the infrastructure identity problem Founding Mailgun and the Rackspace acquisition How Teleport started as a free open source SaaS component COVID kills Gravity pipeline and accelerates Teleport demand The first enterprise deal - improvised on a cold call Why open source SaaS builds trust for security products Discovering they were selling to the wrong buyer persona Shifting from engineers to VPs - 3x average deal size AI as COVID 2.0 - identity for AI agents Lightning round Resources Full show notes: https://saasclub.io/480 Join 5,000+ SaaS founders: https://saasclub.io/email

Ev Kontsevoy

Co-Founder and CEO

TeleportGravitational

Most SaaS onboarding is terrible - rigid, pushy, and forgettable. Karel Papik spent 15 years designing video games before he looked at B2B software and thought: this is hopeless. He co-founded Product Fruits, a digital adoption platform that now serves over 1,300 paying customers. Founders will hear how gaming psychology transformed their SaaS onboarding and helped them break through the $2M ARR ceiling. Karel shares how Product Fruits grew from 6 customers to $50K MRR in 12 months using PPC as the sole acquisition channel, why their product-led growth strategy stopped working at $2M ARR, and how rebuilding the entire platform around AI turned their SaaS onboarding tool into something competitors can't match. Plus the "diamond axe" technique from gaming that drove 24-25% free trial conversion. Product Fruits is based in Prague, Czech Republic, with 25 team members and over 1,300 paying customers including KPMG, universities, and stock exchanges. The company has raised venture funding from Lighthouse Ventures and Reflex Capital, with the US as its biggest market. This episode is brought to you by: 🌎 ThreatLocker → Book a demo 🔍 Respona → Get featured in AI answers on ChatGPT and Google AI Overviews 🔑 Key Lessons 🎮 Gaming psychology transforms SaaS onboarding: Karel applied the "diamond axe" technique from video games - give users the premium experience free, let them feel the value, then ask them to pay. Product Fruits used this to achieve 24-25% free trial conversion. 🎯 Test your biggest market from day one: Product Fruits targeted the US market immediately from Czech Republic instead of starting locally. Karel wanted to know as fast as possible if they could compete globally - and if not, fail fast rather than waste years on small markets. 💰 PPC works when you have the right operator: Most founders say PPC doesn't work, but Product Fruits scaled it to $1.5M/year with 8-9 month payback. The difference was hiring a PPC expert and optimizing landing pages rather than treating ads as a side project. 📉 PLG breaks down as onboarding products get complex: Product Fruits hit a growth wall at $2M ARR when the platform outgrew self-serve. Customers could not discover capabilities on their own, forcing a shift to sales-assisted growth with bigger tickets. 🐯 Rebuild before the decline forces your hand: Karel told investors he was pausing the current product to rebuild around AI - before revenue declined. Investors backed the move within 20 minutes, seeing it as a sign of a winning team rather than a distress signal. 🤖 Ship AI that solves real problems, not investor checkboxes: Product Fruits' AI copilot resolves 80% of support tickets without humans. Karel's test for any AI feature: can we sell it today? If it does not deliver measurable value, it does not ship. 🧠 Stop talking to customers when you need to dream: Karel's contrarian take - over-relying on customer feedback produces small improvements but blocks breakthrough innovation. Customers do not know what is possible in your domain. Sometimes you need to disconnect and imagine the future. Chapters Introduction What Product Fruits does and who it serves 1,300 customers across industries - not just SaaS Riding the tiger - the company philosophy Karel's video game background and meeting co-founder Ladislav Gaming psychology applied to SaaS onboarding The diamond axe technique - let users feel value before paying Growing from 6 to 1,300 customers with PPC Why PPC worked when most founders say it doesn't Pricing strategy and the "too cheap" problem PLG hitting a wall at $2M ARR The AI pivot - rebuilding the platform from scratch How investors responded to the rebuild decision AI features that actually deliver value 80% of support tickets resolved by AI What AI feature they decided NOT to build Lightning round Resources Full show notes: https://saasclub.io/479 Join 5,000+ SaaS founders: https://saasclub.io/email

Karel Papik

Co-Founder

Product Fruits

Three years. Zero traction. Then product-market fit hit - twice. Girish Redekar taught himself to code at 28 and spent years on failed ideas before B2B product-market fit clicked with RecruiterBox. Customers endured a broken PayPal payment hack just to keep using the product. He bootstrapped to 2,500+ customers, sold it, then found product-market fit again with Sprinto by paying for 10 audits before writing code. Girish shares how he validated demand using The Mom Test, why 17 of 20 GTM channels failed, and the 3 that drove Sprinto to 8-figure ARR with 3,000+ customers. Sprinto is an autonomous compliance platform with $32M raised and 350 people. AI is changing the business from three directions - product, customer operations, and external threats. This episode is brought to you by: 🌎 ThreatLocker → Book a demo 💖 Gearheart → Book a free consult and get the first 20 hours free 🔑 Key Lessons 🎯 B2B product-market fit shows up in customer behavior, not metrics: RecruiterBox knew it had something real when customers kept paying through a broken PayPal system with daily-depleting credits. The pain they tolerated was the signal. 💰 Sell a profitable business when you become the bottleneck: Girish sold RecruiterBox at single-digit millions ARR because growth had plateaued and the founders were not the right people to scale it further. 🔄 Eliminate product risk before writing code: Sprinto's biggest question was whether a consulting service could become software. Ten paid audits answered that before a line of code was written. 🚀 Harvest existing demand instead of creating it: Sprinto's first customers came from founder Slack groups, VC portfolio programs, and Google - places where people already looked for answers. 📉 Expect 85% of your GTM channels to fail: Girish tried 20 channels and 17 did not work. Partner co-selling and conferences only started working after Sprinto had brand recognition. 🧠 Founder-product fit matters as much as product-market fit: Girish passed on a WordPress competitor because the GTM required developer evangelism - not a strength. Pick the right problem for your skills. 🛠️ AI is hitting compliance from three directions: Product capabilities, customers running AI internally needing governance, and attackers using AI for sophisticated threats - creating compounding demand. Chapters What Sprinto does and key business metrics Failed ideas before RecruiterBox What kept them going through 2-3 years of no traction The PayPal payment hack that proved product-market fit Why they sold a profitable, growing business Finding product-market fit the second time with The Mom Test Paying for 10 audits to validate the product Product risk vs market risk framework 20 GTM channels tried, 3 worked How AI impacts the business from three directions Resources Full show notes: https://saasclub.io/478 Join 5,000+ SaaS founders: https://saasclub.io/email

Girish Redekar

Co-Founder

Sprinto

His competitors have raised hundreds of millions. ChatGPT can do the basics of what his product does. Sylvestre Dupont's entire company is six people. His competitive differentiation strategy - that most businesses want something simple that works in minutes, not enterprise complexity - is what keeps Parseur alive and growing 60% year over year. Founders will hear how Dupont rebuilt from rule-based to AI-powered parsing while bootstrapped, why simplicity is a stronger competitive advantage than features or funding, and how a tiny team's SaaS positioning bet is beating players with 100x the resources. Parseur generates 7-figure ARR with 1,000 customers in 70+ countries. Competitive differentiation through simplicity keeps them growing - bootstrapped, six people, 100% founder-owned. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🌎 ThreatLocker → Book a demo 🔑 Key Lessons 🎯 Competitive differentiation through simplicity beats enterprise complexity: Parseur's 10-minute self-serve setup wins against competitors requiring sales calls and hundreds of millions in funding. 🧠 AI commoditizes features, not end-to-end solutions: ChatGPT can parse one PDF, but it can't handle pre-processing, routing, compliance, and integration at scale - that's where the real product value lives. 💰 You can fund an AI rebuild from revenue, not investors: Parseur rebuilt from rule-based to AI-powered parsing using customer revenue, keeping 100% ownership and avoiding dilution. 📉 Launch failures don't kill the product - bad positioning does: Sylvestre launched to crickets, dropped price 80%, and rebuilt his approach from scratch. The product was fine - the go-to-market was the problem. 🚀 Integration partnerships pre-qualify customers: Parseur's Zapier connector converted at 20-30% because those users were already automation buyers looking to connect tools. 🎯 Horizontal SaaS works when your competitive differentiation is use-case specific: Parseur is generic, but their SEO targets individual use cases - making them appear vertical to each customer segment. 🤝 Genuine community engagement beats marketing at the start: Answering real questions on Quora without being promotional built trust and attracted Parseur's earliest paying users. Chapters Introduction and quote - keep it simple, stupid What Parseur does - automating data extraction from documents Business overview - 7-figure ARR, 1000 customers, 6 people Origin story - from travel map side project to SaaS The failed launch - a year of building, zero marketing Finding first customers on Quora Pricing mistake - dropping from $49 to $9 How simplicity became the competitive differentiation moat The Zapier integration that converted at 20-30% SEO as the 95% acquisition engine AI disruption - rebuilding from rule-based to AI-powered Managing AI costs on a bootstrapped budget Standing out against VC-funded players with simplicity Why horizontal SaaS worked instead of going vertical Adapting for the AI search era Lightning round Resources Full show notes: https://saasclub.io/477 Join 5,000+ SaaS founders: https://saasclub.io/email

Sylvestre Dupont

Founder

Parseur

Five years to the first million. Zero dollars raised. NFL teams pay the same price as high school teams. Hewitt Tomlin built TeamBuildr into a $10M ARR vertical SaaS company by focusing on one job function and refusing to charge enterprise customers more. Founders will hear why flat pricing drove more growth than premium tiers ever could. Hewitt shares how a single conversation with a college strength coach pivoted TeamBuildr from a social app to industry-specific SaaS, why founders who plateau at $500K ARR have a product-market fit problem, and how building for a job function instead of a market segment unlocked every customer from high schools to the NFL. Plus: Hewitt's take on why he won't build AI features until his customers ask for them - even as his biggest competitor bets on replacing coaches with AI entirely. TeamBuildr has 45 employees, has never raised funding, and still operates on the same co-founder agreement from 2012. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🌎 ThreatLocker → Book a demo 🔑 Key Lessons 🏢 Build vertical SaaS around a job function, not a market segment: TeamBuildr focused on the strength coaching workflow rather than targeting colleges or pro teams separately. This unlocked every segment from high schools to NFL teams with a single product. 💰 Flat pricing can drive niche SaaS growth through social proof: Hewitt charges pro teams the same as high schools, trading premium revenue for NFL logos that validate TeamBuildr to the volume market. As a bootstrapped company, this was more pragmatic than building enterprise tiers. 🎯 Stalling at $500K ARR signals a product-market fit problem: Hewitt advises that founders putting in full-time effort but plateauing for consecutive years should stop tweaking their go-to-market and reexamine whether their product actually solves what the market needs. 🤝 Treat early users as partners, not beta testers: Hewitt didn't send logins and wait for feedback. He showed up at conferences, called coaches personally, and built relationships. His first customer Dr. Steve Smith is still someone he stays in touch with 13 years later. 🧠 Listen to what customers want, not what they say they want: Customers describe missing features because they can't articulate the outcome they need. Hewitt's job is to peel back the request and identify the real workflow improvement, then decide what to build independently. 🛠️ Don't build AI features for the sake of building them in vertical software: While competitor Volt bets on AI replacing coaches, Hewitt waits for actual customer demand. He uses AI internally for developer productivity but won't ship customer-facing AI without conviction it enhances the profession. 🚀 Inbound marketing gets stronger as your niche SaaS customer base grows: Hewitt transitioned from cold calling to inbound by telling customer stories. Following HubSpot's principle that the best inbound originates with customers, a growing base made content and social proof more potent over time. Chapters What TeamBuildr does and who it's for How the idea started as a social app in college Revenue, team size, and business structure today Pivoting from athletes to coaches The conversation that changed everything Building the MVP and making the first dollar Getting free users to actually use the product Listening to what customers really want Competing with Excel in a market that didn't know SaaS existed Five years to the first million in ARR How Hewitt knew he had product-market fit Outbound vs inbound on the way to $1M Why half the customers are high schools Charging NFL teams the same as high school teams Building vertical SaaS around AI without replacing coaches Why customers aren't asking for AI yet Lightning round Resources Full show notes: https://saasclub.io/476 Join 5,000+ SaaS founders: https://saasclub.io/email

Hewitt Tomlin

Founder

TeamBuildr

Sarah Ahmad offered her first product for free during COVID. Nobody signed up. Her next company hit 10,000 customers and 8-figure ARR. The difference was SaaS product-market fit - validated before writing a single line of code. Sarah shares how she and her co-founder tested demand with a landing page in the YC community, signed 100 paying customers using Google Drive and a Stripe link, and built Stable into the leading AI-powered virtual mailbox for businesses. She also explains why the SEO playbook that built the company stopped working and what replaced it. Stable serves over 10,000 companies - from solopreneurs to enterprises like DoorDash, GitLab, and Realty Income - with 50-60 employees and operations across 20+ US locations. This episode is brought to you by: 🌎 ThreatLocker → Book a demo 💖 Gearheart → Book a free consult and get the first 20 hours free 🔑 Key Lessons 🎯 Test SaaS product-market fit before writing code: Sarah's first startup Mistro failed because she built the full product before validating demand. With Stable, she validated with a landing page and manual operations - signing 100 paying customers before writing any software. 📉 Zero signups at zero price means no product-market fit: During COVID, Mistro couldn't get users even for free. That signal was clearer than any metric - if people won't use it for nothing, the problem isn't pricing, it's relevance. 🛠️ Use embarrassingly manual MVPs for market validation: Stable's first version was Google Drive, Zoom, and Stripe. Customers sent IDs via email. It was embarrassing, but it captured real demand while the team figured out what to build. 💰 Spend enough on paid ads to get real signal: Sarah's team spent only a few hundred dollars per week on ads - not enough to know if the channel worked. She now recommends spending thousands to saturate high-intent searches before optimizing. 🚀 Word of mouth scales when you solve a real pain point: Stable reached 1,000 customers before hiring anyone for growth, with a team of just 6-7 people at $1M ARR. Genuine product-market fit drove organic referrals without a marketing budget. 🤝 Compensate for a rough product with exceptional customer experience: Sarah and her co-founder personally onboarded every early customer via Zoom and handled all support. People forgive a rough product when you solve a real problem and show up for them. 🏢 Physical operations create a moat AI can't easily replicate: Stable's processing centers and logistics network across 20+ locations give it a defensibility layer that pure software companies don't have. Chapters Introduction First startup Mistro and why it failed Discovering the virtual mailbox opportunity Validating demand with a landing page The no-code MVP with Google Drive and Stripe How Stable differentiated from legacy incumbents Getting to 1,000 customers with a team of 6 The paid ads mistake most early founders make From manual operations to building software How AI is changing the product and industry Testing SaaS product-market fit versus building blind Shifting from product builder to CEO Resources Full show notes: https://saasclub.io/475 Join 5,000+ SaaS founders: https://saasclub.io/email

Sarah Ahmad

Co-Founder

Stable

100 restaurants. Every order processed manually. Zero lines of code. Zhong Xu built Deliverect by turning integration partners into a SaaS distribution channel that scaled his product 10x faster than direct sales. Here's how he reached 80,000 restaurants and nearly $100M ARR through partnerships instead of cold outreach. Zhong shares why he launched with a Wizard of Oz MVP, how he convinced competing software companies to distribute his product, and why he opened 10 offices in a single quarter during COVID to block local incumbents before they could form. Plus: Zhong's take on why AI might turn his platform into commodity infrastructure - and his strategy to stay ahead. Deliverect connects delivery platforms like Uber Eats and DoorDash to restaurant systems across 50 countries. Zhong previously co-founded a restaurant software company that merged with Lightspeed, which IPO'd in 2019. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🌎 ThreatLocker → Book a demo 🔑 Key Lessons 🚀 Build a SaaS distribution channel through integration partnerships: Zhong partnered with 10+ software companies who each brought 100 restaurants monthly, reaching 80,000 locations across 50 countries faster than any direct sales team could. 🛠️ Launch with a Wizard of Oz MVP before writing code: Deliverect signed up 100 restaurants and manually processed every order before building anything, proving demand without wasting months on unvalidated features. 🤝 Attribute leads to distribution partners to avoid conflict: Zhong always credited partners for deals regardless of how customers arrived, eliminating the channel conflict that destroys most partnership-driven growth programs. ⚡ Enter every market before local incumbents emerge: Deliverect opened 10 offices in one quarter during COVID, betting that being number 1 or 2 early was cheaper than displacing entrenched local competitors later. 💰 Always charge early customers - free users give less feedback: Zhong found that non-paying customers feel guilty requesting help and stay silent, while even $50/month customers actively engage and provide honest product feedback. 🧠 Deep domain expertise creates unfair SaaS distribution advantages: Zhong's 12+ years in restaurant tech meant he had every partner CEO's phone number at launch, turning cold outreach into warm partnership conversations. 🎯 Build the intelligence layer before you become commodity infrastructure: Deliverect is racing to add AI-powered menu optimization and agent commerce because connectivity alone is replicable, but owning the restaurant intelligence layer is a defensible moat. Chapters Introduction What Deliverect does and how it works 80,000 restaurants and approaching $100M ARR How Zhong's father inspired his entrepreneurial journey Building one of the first tablet-based restaurant platforms Where the idea for Deliverect came from Why four co-founders and why distribution beats product The Wizard of Oz MVP - manual orders for 100 restaurants Resources Full show notes: https://saasclub.io/474 Join 5,000+ SaaS founders: https://saasclub.io/email

Zhong Xu

Co-Founder and CEO

Deliverect

Joel Griffith's first customer paid $200 a month. His infrastructure cost $50. He was profitable from day one. But it took three years of nights and weekends before his bootstrapped SaaS hit $500K ARR. Then Google Cloud launched a competing product and a startup raised $60M to go after his market. His growth did not flinch - because eight years of content had built a bootstrapped SaaS moat that funding could not replicate. You will learn how to get first customers for a bootstrapped SaaS by teaching on GitHub and Stack Overflow, why a self-funded SaaS content engine that compounds over 8 years outlasts any viral spike, and how to scale a bootstrap operation beyond what you can handle solo by partnering instead of hiring. Joel Griffith is the founder of Browserless, a browser automation platform approaching $4M ARR with under 10 people. Joel is a jazz trumpet player turned engineer who went through five failed B2C ideas before building a profitable SaaS by solving his own pain as a developer. He has never raised a dollar. This episode is brought to you by: 🌎 ThreatLocker → Book a demo 🔑 Key Lessons 🎯 Solve your own pain for bootstrapped SaaS success: Joel failed at five B2C ideas before realizing the problems he understood best were engineering problems - leading to a business that was profitable from day one. 🤝 Get first customers by teaching, not pitching: Joel's first 10 customers came from answering GitHub issues and Stack Overflow questions about browser automation, building trust before mentioning his bootstrapped SaaS. 🚀 Build a content engine that compounds over years: Eight years of blog posts, forum answers, and open source contributions now drive almost all inbound for this self-funded SaaS at nearly $4M ARR. 🏢 Partner to fill skill gaps instead of struggling through them: At $60K MRR solo, Joel partnered with Polychrome for hiring, sales, and legal instead of trying to learn everything himself. 💰 Bootstrapped SaaS beats VC-backed competitors through relationships: When Google Cloud and a $60M-funded startup entered his space, Joel's growth did not change because customers valued direct access to a founder with domain expertise. Chapters Introduction What is Browserless and who is it for Business size: nearly $4M ARR, under 10 people Five failed B2C ideas before finding developer-market fit Three years as a side project before going full-time Running solo to $60K MRR as a one-person bootstrapped SaaS Getting the first 10 customers from GitHub and Stack Overflow First customer: $200/month, profitable from day one Content engine still driving almost all inbound at $4M ARR Partnering with Polychrome to handle operations Competing with a $60M-funded startup and Google Cloud How AI agents created new demand for browser automation Lightning round Resources Full show notes: https://saasclub.io/473 Join 5,000+ SaaS founders: https://saasclub.io/email

Joel Griffith

Founder

Browserless

Vineet Jain arrived in the US with $100 and built Egnyte to over $300M in enterprise sales revenue - without freemium. While Box and Dropbox gave products away and raised billions, Vineet charged from day one. His first enterprise sales pipeline started with $6,000 in SEM. It took 12 years to hit $100M - then just 3 more to reach $300M. You will learn why enterprise sales can outperform freemium in crowded markets, how to land Fortune 86 enterprise customers as a 12-person startup through B2B sales discipline, and the inside sales strategy that kept cost of acquisition low while scaling to 400 staff selling to enterprise. Vineet Jain is the co-founder and CEO of Egnyte, a content collaboration and security platform with 23,000 enterprise customers and 1,400 employees. Egnyte has raised just $137.5M with no funding since 2018. In 2016, Gartner named Egnyte a leader alongside competitors that had raised billions more. This episode is brought to you by: 🌎 ThreatLocker → Book a demo 🔑 Key Lessons 🏢 Enterprise sales can outperform freemium: Egnyte refused to offer free tiers while competitors gave products away and raised billions. Charging from day one built a sustainable B2B sales engine now generating $300M+. 💰 Start your enterprise sales pipeline with SEM: Vineet spent $6K on search engine marketing in month one. That systematic approach scaled to millions per quarter and still drives 60% of pipeline through inside sales. 🎯 Lead with compliance to win enterprise customers as a tiny startup: Egnyte landed a Fortune 86 company within its first 25 deals by focusing on enterprise certifications and content governance. 🛠️ Build hybrid when the market says go cloud-only: 30% of Egnyte's enterprise customers use hybrid deployment for use cases where pure cloud fails - like construction sites needing LAN-speed access to massive files. 🚀 Scale inside sales in low-cost cities to keep CAC low: Egnyte built offices in Spokane, Raleigh, and Salt Lake City instead of expensive tech hubs, keeping selling to enterprise cost-effective at 400 staff. Chapters Introduction What Egnyte does and company overview Revenue milestones - $100M in 12 years, $300M in under 5 more Arriving in the US with $100 and building from nothing First startup Valdero - raised $7.5M and failed Starting Egnyte with 4 co-founders and no funding Going enterprise sales only when everyone said do freemium The hybrid cloud bet Landing the first enterprise customers with $6K in SEM A Fortune 86 company visiting a 12-person startup Consensus is the shortest path to mediocrity AI strategy and the Egnyte Copilot launch Lightning round Resources Full show notes: https://saasclub.io/472 Join 5,000+ SaaS founders: https://saasclub.io/email

Vineet Jain

CEO

Egnyte

Adam Markowitz spent seven years selling a nice-to-have in edtech. Then he built Drata and found product-market fit so strong that prospects called to complain his sales team was too aggressive. He signed 100 customers in six weeks and 1,000 in year one. The difference between a vitamin and a painkiller is product-market fit. You will learn how to validate product-market fit before writing code by talking to dozens of companies and auditors, why dogfooding your own product creates instant market validation, and how a "give before you take" AWS partnership made Drata a top 5 ISV on Marketplace in under two years. Adam Markowitz is the co-founder and CEO of Drata, a trust management platform with over 8,000 customers across 60 countries, 600+ employees, and $100M+ ARR. Drata achieved product-market alignment by solving a compliance pain Adam experienced firsthand at Portfolium, which was acquired for $43M. The company has raised over $300M. This episode is brought to you by: 🌎 ThreatLocker → Book a demo 🔑 Key Lessons 🎯 Product-market fit shows in buyer urgency: Drata signed 100 customers in 6 weeks and 1,000 in year one - versus years to close the first 5 university customers at Portfolium where PMF was missing. 🛠️ Dogfood your product before selling it: Drata refused to accept customers until they used their own tool to get SOC 2 compliant, giving them instant credibility and proving product-market fit under real conditions. 🔍 Validate by talking to every stakeholder: Adam spoke with dozens of companies and auditors before writing code, discovering identical pain patterns that made the initial product scope and market validation obvious. 🤝 Give before you take with strategic partners: Drata brought thousands of first-time customers to AWS Marketplace before asking for anything, becoming a top 5 global ISV in under two years. 📉 Product-market fit means selling a painkiller: Seven years in edtech taught Adam what a vitamin feels like. At Drata, customers lined up because compliance was blocking their deals. Chapters Introduction What Drata does and the trust problem it solves Revenue, customers, and team size From astronaut dreams to NASA's Space Shuttle program Building Portfolium and selling for $43M The long road to product-market fit in edtech How the Portfolium pain led to founding Drata Validating the problem before writing code Using Drata to get their own SOC 2 before selling Signing 100 customers in six weeks Building the Auditor Alliance partner program The AWS Marketplace strategy and give-before-you-take Why aggressive sales culture was intentional AI tailwinds for compliance and trust Lightning round Resources Full show notes: https://saasclub.io/471 Join 5,000+ SaaS founders: https://saasclub.io/email

Adam Markowitz

Co-Founder and CEO

Drata

Livestorm went from $2M to $9M ARR in one year during COVID - then lost SaaS product-market fit. Gilles Bertaux expanded into meetings and sales demos, turning Livestorm into a smaller Zoom. After a failed Series C, he rebuilt SaaS product-market fit by narrowing to enterprise webinars for European marketers in banking and pharma. You will learn why explosive growth can mask fragile SaaS product-market fit, how to rebuild PMF by narrowing positioning instead of expanding features, and why shifting from PLG to enterprise sales required replacing almost the entire sales team. Gilles Bertaux is the co-founder and CEO of Livestorm, a webinar platform for enterprise marketers. The company generates nearly $20M ARR with 3,500 customers and has raised $35M. Gilles built Livestorm as a university project in 2016, grew it through SEO and Quora, then navigated the product-market alignment challenge of post-COVID market validation. This episode is brought to you by: 🌎 ThreatLocker → Book a demo 💖 Gearheart → Book a free consult and get the first 20 hours free 🔑 Key Lessons 🎯 SaaS product-market fit can be lost by expanding too broadly: Livestorm added meetings and sales demos after COVID, becoming a smaller Zoom with no clear differentiator and declining conversion rates. 📉 Explosive growth can mask fragile PMF: Going from $2M to $9M ARR felt like traction, but 85% of customers were on monthly plans - one click away from churning overnight. 🏢 Narrow positioning wins against giants: Livestorm stopped competing feature-for-feature with Zoom and differentiated on three dimensions - European company for security, marketers only, and specific industries. 🔄 Enterprise sales requires rebuilding, not retraining: Reps who closed inbound leads could not cold-call 10,000-person companies. Gilles replaced almost the entire sales team with enterprise outbound specialists. 💰 A failed fundraise can force the right strategic shift: When Series C investors said no, Livestorm had to become profitable - pushing toward enterprise customers on annual contracts who pay more and stay longer. Chapters Introduction What Livestorm does and revenue milestones Building Livestorm as a university project The disastrous first webinar launch SEO, Quora, and co-marketing as early growth engines How SaaS product-market fit shifted after COVID Going from $2M to $9M ARR in one year Post-COVID churn and the virtual event collapse Losing SaaS product-market fit by becoming a smaller Zoom Rebuilding positioning around Europe, marketers, and industries The painful shift from PLG to enterprise sales Lightning round Resources Full show notes: https://saasclub.io/470 Join 5,000+ SaaS founders: https://saasclub.io/email

Gilles Bertaux

Co-Founder and CEO

Livestorm

Every wireframing tool claimed to use AI - but they were faking it. Adam Fard tested the competition, found they were swapping templates, and built an AI SaaS that actually generates wireframes from scratch. UX Pilot went from side project to $5.3M ARR in under two years. You will learn how to validate an AI SaaS opportunity by testing competitor claims, why a code-first architecture creates a competitive moat for an AI-powered SaaS product, and the content strategy that built a 600,000-subscriber newsletter without generic educational content. Adam Fard is the founder of UX Pilot, an AI startup that helps product design teams create wireframes and ship UX work faster. He bootstrapped the company using revenue from his UX agency, growing from $3M to $5.3M ARR in just 5 months with 15,000 paying subscribers and a 30-person team. This episode is brought to you by: 🌎 ThreatLocker → Book a demo 💖 Gearheart → Book a free consult and get the first 20 hours free 🔑 Key Lessons 🎯 Test competitor claims to find AI SaaS opportunities: Adam discovered other wireframing tools were faking AI generation by swapping templates, revealing a genuine technical gap nobody else could solve. 💰 Fund your AI SaaS with existing revenue: Agency income removed VC pressure and let Adam iterate for 6-7 months on fine-tuning LLMs and component-based approaches without chasing growth. 🚀 Focus on one hard problem instead of building with AI for everything: While competitors built no-code tools that did everything, Adam focused exclusively on AI wireframe generation for the design phase. 📈 SEO still works for AI-powered SaaS: Despite claims that SEO is dead, Adam captured high-intent keywords around design, UX, and AI generation by being one of the first products to target them. 🛠️ Talk about product updates, not educational content: Adam got more newsletter engagement sharing UX Pilot features than sending generic UX education - 600,000 subscribers engaged more with product news. Chapters Introduction What UX Pilot does and who it's for Revenue, team size, and growth metrics Running a UX agency when ChatGPT launched The user question that sparked the AI SaaS idea Testing competitors and discovering they were faking AI Why creating wireframes with AI was technically hard Building an MVP and exploring fine-tuning LLMs Building a 600K subscriber newsletter from product signups Getting to the first million in ARR with LinkedIn and SEO The inflection point from $3M to $5.3M ARR in 5 months Lightning round Resources Full show notes: https://saasclub.io/469 Join 5,000+ SaaS founders: https://saasclub.io/email

Adam Fard

Founder

UX Pilot

Two Uber product designers raised $3 million, built a scheduling tool, and watched it fail for two years. Then Tito Goldstein threw it out, rebuilt with composable Legos, and outsold the previous two years in the first month. That's the moment B2B product-market fit arrived. Tito reveals the brutal reality of searching for B2B product-market fit when you're too close to the solution, why composability beats cookie-cutter features for market validation, and how listening to what customers don't say became TeamBridge's unfair advantage. TeamBridge is a composable workforce operating system serving over 500,000 employees across 200+ enterprise customers including NFL stadiums. Tito and his co-founder were two of the first principal product designers at Uber before founding TeamBridge. This episode is brought to you by: 🌎 ThreatLocker → Book a demo 💖 Gearheart → Book a free consult and get the first 20 hours free 🔑 Key Lessons 🎯 B2B product-market fit hides in what customers don't say: TeamBridge buyers asked for features, but the real pain was "I need to stand out, not use the same software as competitors." The unstated need pointed to composability as the path to PMF. 📉 Sunk cost kills product-market fit - be willing to start over: After two years of near-zero revenue, Tito scrapped the scheduling tool and rebuilt as composable Legos that outsold two years of efforts in month one. 🏢 B2B product-market fit shifts as you move upmarket: SMBs wanted plug-and-play, but enterprise customers had unique workflows no off-the-shelf tool could handle. Composability naturally gravitates toward larger companies. 🤝 Enter new verticals by admitting you're naive but capable: When TeamBridge approached NFL stadiums, they openly said they were new to the space. First-mover partners were attracted to honest positioning and composable technology. 🔄 COVID constraints can accelerate go-to-market maturity: When door-to-door sales died overnight, TeamBridge's product-designer founders had to learn outbound email and cold calling - building market validation muscles that still power their motion. Chapters Introduction and favorite quotes What TeamBridge does and who it serves Why composability matters for workforce software Origin story: interviewing Uber drivers Raising $3M seed with just a prototype Why it took 2 years to find B2B product-market fit The pivot: from scheduling to composable Legos First significant sale during COVID Finding the right messaging and storytelling Moving upmarket to enterprise customers Discovery-first selling: hold the pitch until you know the pain Learning the nuances of each vertical Lightning round Resources Full show notes: https://saasclub.io/468 Join 5,000+ SaaS founders: https://saasclub.io/email

Tito Goldstein

Co-Founder

TeamBridge

He wore a Stanford sweatshirt to a conference. Five minutes later, he had his first customer. Nate Baker found his first customers through network selling, not cold outreach - then lived in that customer's basement for a year. That relationship set the foundation for Qualia's growth to $100M ARR. Nate reveals why the first 25 Qualia employees rotated through Barry's basement to learn the industry, the multi-year upfront contracts that brought forward $100K in cash at just $45K ARR, and the wake-up call when a VP of Sales said: "I've never seen such a gap between great product and incompetent sales execution." Qualia is a title software platform generating over $100M in ARR with 600 employees and $200M+ raised. Nate started building at 21 with zero real estate experience and found his early customers entirely through network-based relationships. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🔑 Key Lessons 🤝 First customers must come from network selling: Nate says your first 10 customers have to be in-network sales. Barry introduced Qualia to his competitors, building the foundation for initial traction. 🏠 Embed yourself with first customers to learn their world: Nate and the first 25 Qualia employees rotated through living in Barry's basement. "To actually understand what your customer does, you just have to be so in it." 💰 Use multi-year upfront contracts to align early incentives: Qualia offered 5-year contracts at 80% discounts, collecting $100K upfront from early customers when they had just $45K ARR. 🗺️ Geographic focus beats national expansion for first customers: Qualia stayed in Massachusetts for the first year, building density and network effects in one state before expanding. 🔧 Hire sales leadership before you think you're ready: At $45K ARR, Qualia's VP of Sales exposed the gap between great product and incompetent execution. Within 12 months they hit $3.5M ARR. Chapters Introduction and what Qualia does How Nate picked the title software market at 21 Finding first customer Barry Feingold at a conference Living in Barry's basement for a year When Barry's vendor shut him off overnight Why narrow geographic focus beats national expansion How to get first customers to pay before building The multi-year upfront contract strategy Network selling vs cold outreach for first customers The wake-up call: "Great product, incompetent execution" Moving upmarket and geographic expansion How AI is changing the opportunity Lightning round Resources Full show notes: https://saasclub.io/467 Join 5,000+ SaaS founders: https://saasclub.io/email

Nate Baker

Co-Founder and CEO

Qualia

A cold text to a stranger's phone number. Nine months just to close the POC paperwork. Yosef Peterseil landed McDonald's as his first B2B SaaS sales customer while bootstrapping with zero revenue. The lesson: charging even $3,000 for a POC completely changes the dynamics of closing deals. Yosef reveals why their original ICP of customer success managers had no budget, how 70 hard-earned event leads went cold because they had no follow-up system, and the 13-month contract structure that eliminated double-negotiation traps in B2B deal cycles. Blings is a personalized video platform serving enterprise sales customers including McDonald's, Mercedes, Meta, and Rocket Mortgage. The company hit $1M ARR in 2023 with a team of 19. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🔑 Key Lessons 🎯 Validate ICP budget before building your B2B SaaS sales motion: Yosef interviewed dozens of customer success managers before discovering they had no budget - pivoting to marketing where the money was saved months of wasted effort. 💰 Always charge for POCs in B2B SaaS sales: Even $3,000-$5,000 forces customers to prioritize your project, starts vendor onboarding, and signals they're serious about closing deals rather than just exploring. 📄 Combine POC and commercial into one contract: Yosef lost months negotiating POC terms only to negotiate again for the commercial deal - 13-month contracts with first-month exit clauses eliminated the trap. 📉 Build follow-up systems before generating leads: Blings spent $20K-$30K on a conference and captured 70 leads, but had no lead scoring or sequences - the entire investment was wasted. 🔗 Use channel partners to scale enterprise sales doors: Recruiting industry veterans to open doors for recurring commission scaled Blings faster than direct B2B SaaS sales alone. Chapters Introduction and favorite quote What Blings does - the MP5 video format Company metrics and enterprise customers Validating the ICP through customer interviews Pivoting from customer success to marketing Landing McDonald's through a cold text Closing the first B2B SaaS sales POC Why you should always charge for POCs Event marketing mistakes - 70 lost leads Hiring salespeople too early Building channel partner relationships Lightning round Resources Full show notes: https://saasclub.io/466 Join 5,000+ SaaS founders: https://saasclub.io/email

Yosef Peterseil

Co-Founder

Blings

Most founders think enterprise sales takes 6-12 months. Bassem Hamdy closes deals in 9 days. After scaling Procore from $10M to $100M, Bassem built Briq - an AI workforce platform now doing 8 figures in revenue. His enterprise sales strategy is counterintuitive: never demo the product early, never do free POCs, and always charge from day one. Bassem reveals why selling to enterprise starts with vision and value before showing a single screen ("I could demo a blank screen - they don't know what you're demoing anyway"), how targeting CFOs instead of innovation teams compresses B2B sales cycles, and the land-and-expand playbook that grew a $15K first deal into 8-figure enterprise sales revenue. Briq is an AI orchestration platform for construction and manufacturing that automates back-office work for enterprise deal cycles across Fortune 100 companies. Bassem spent 15 years in construction tech before selling to enterprise in this market. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🔑 Key Lessons 🏢 Enterprise sales starts with vision, not demos: Bassem says "I could demo a blank screen" - customers don't know what they're looking at anyway. Align on vision and value first, and enterprise deal cycles shrink from months to days. 💰 Never do free POCs in enterprise sales - even $1 creates commitment: Free pilots attract time-wasters. The moment money changes hands in B2B sales, prospects become invested in making the product work. 🎯 Target CFOs, not innovation teams: Innovation teams chase shiny objects but can't write checks. CFOs control the checkbook, love price certainty, and close enterprise sales quickly once they see ROI. 📈 Land small and expand to grow revenue: Briq's first deal was $15K. Through disciplined land-and-expand with consumption pricing, they grew to 8 figures selling to enterprise. 🔄 Don't pivot away from product-market fit: Briq had PMF with their automation product but pivoted to forecasting under investor pressure - and had to "refound" the company to recover. Chapters Why SaaS founders should ignore feature requests Introduction and welcome What Briq does: AI workforce for physical industries The failed "construction data cloud" idea The investor-forced pivot to forecasting How to close enterprise sales deals in 9 days Selling on vision and value vs. features Why you should never do free enterprise POCs SaaS pricing: moving to consumption-based tokenization Selling to CFOs: overcoming risk aversion Firing bad enterprise clients Lightning round Resources Full show notes: https://saasclub.io/465 Join 5,000+ SaaS founders: https://saasclub.io/email

Bassem Hamdy

Co-Founder and CEO

Briq

His co-founder live-coded a fix during the Instacart pitch - and closed the deal on the spot. Saket Saurabh used consultative selling SaaS techniques to close 15 enterprise customers including Instacart, LinkedIn, and DoorDash before hiring a single salesperson. Saket reveals why he went "enterprise first" instead of starting with SMBs, the consultative selling SaaS approach that turns every meeting into problem-solving instead of pitching, and the zero-salary pivot that made Nexla cash flow positive before their $12M Series A. Nexla is an enterprise data platform serving 50+ customers with 6-figure ACV deals. Saket's founder-led sales motion grew the company to over $5M ARR after raising $33M total. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🚨 NordStellar → Book a demo and get 20% off with code blackfriday20 🔑 Key Lessons 🤝 Consultative selling SaaS connects product to market: Unless founders sell deals themselves, they miss critical signals about pricing and product direction. Saket closed 15 enterprise customers before hiring salespeople. 🪄 Create "magical moments" in demos: Saket's co-founder live-coded a data fix during the Instacart CTO pitch, solving in minutes what took their team weeks. Enterprise selling with agility closes deals faster than slides. 🏢 Go enterprise first to build for real complexity: Architecting for SMBs first prevents you from understanding enterprise-grade problems. Nexla targeted Fortune 500 companies from day one. 🎯 Use thesis-driven outreach instead of cold pitching: Saket built specific hypotheses about each target company's data problems. Starting with "Do you see this problem?" earned trust with technical buyers. 💰 Price against internal build cost, not competitors: Saket estimated what the prospect would spend on internal engineering, then priced Nexla at one-fifth to one-tenth. Consultative selling SaaS means understanding the buyer's economics. Chapters Introduction - the "magical moment" at Instacart What is Nexla? Solving enterprise data fragmentation Origin story: from Nvidia engineer to data entrepreneur Why target enterprise customers from day one What a typical consultative selling meeting looked like The live-coding demo that closed Instacart Figuring out enterprise pricing Closing 15 enterprise deals through founder-led sales Overcoming the "we can build it ourselves" objection The zero-salary pivot to cash flow positivity How AI changed Nexla's product and market Lightning round Resources Full show notes: https://saasclub.io/464 Join 5,000+ SaaS founders: https://saasclub.io/email

Saket Saurabh

Co-Founder and CEO

Nexla

$150K ARR. Customers never logged in. They'd call with a question, get an answer, and disappear. Ibby Syed spent 18 months building what he thought was an AI SaaS - then realized he'd accidentally built a consulting business. The wake-up call came when 100 lines of OpenAI code replaced his entire data science solution. Ibby reveals the exact moment that triggered the AI SaaS pivot, why teaching customers to build their own AI agents scales better than building for them, and the outbound strategy where he sends actual leads from Reddit monitoring before the first call. Cotera is an AI-powered platform that lets enterprise customers build prompt-based AI agents on top of their existing data warehouses. The AI startup has 15 enterprise customers and generates over $1M ARR with a team of 10. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🚨 NordStellar → Book a demo and get 20% off with code blackfriday20 🔑 Key Lessons 🚨 Recognize when your AI SaaS is actually consulting: Ibby hit $150K ARR but customers weren't logging in. They called for answers instead of using the product - a dangerous signal he almost ignored. 💡 Let API breakthroughs trigger your pivot: Ibby's co-founder solved a customer problem with 100 lines of OpenAI code that outperformed a complex data science solution. That contrast made the AI startup opportunity obvious. 🎯 Deliver value upfront in outbound: Instead of pitching, Ibby sends actual leads from a Reddit monitoring AI agent. Showing value before the first call converts better than any cold pitch. 🛠️ Teach customers to build, don't build for them: After the pivot, Cotera stopped doing custom implementations. Teaching customers to build their own AI agents is what made the AI SaaS business scale. 🏢 Enterprise customers want AI on their own infrastructure: Series B+ companies want AI-powered platform capabilities on their existing Snowflake or BigQuery, not third-party clouds. Chapters Introduction and the "White Collar" quote The Y Combinator journey and the first idea Getting first customers through LinkedIn outbound The consulting trap - revenue vs. scalability The wake-up call - 100 lines of code vs. data science The pivot to building an AI SaaS agent platform The "teach, don't do" service model Prompt-based workflows vs. drag-and-drop Why vertical AI startups might die Making AI agents work at scale Lightning round Resources Full show notes: https://saasclub.io/463 Join 5,000+ SaaS founders: https://saasclub.io/email

Ibby Syed

Founder

Cotera

First paying customer: $8 a month for a fantasy football league. Bilal Aijazi's freemium SaaS grew to millions of monthly active users and 7-figure ARR with just 20 people. The challenge was figuring out which of those millions would actually pay. Bilal reveals how he separated casual free users from real buyers in a freemium SaaS, the viral loop where 12% of responders become creators who send polls to new groups, and why diversifying to Teams, Zoom, and Google Slides saved Polly when Slack built a competing feature. Plus: the product-led growth insight that "pollinators" - users picking lunch spots who will never pay - actually drive awareness for the enterprise buyers running company all-hands. Polly is a freemium SaaS engagement platform serving millions of monthly active users across Slack, Teams, Zoom, and embedded presentation tools. The free-to-paid conversion engine generates multiple seven figures in ARR with a team of 20. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 🚨 NordStellar → Book a demo and get 20% off with code blackfriday20 📡 Signal House → Learn more and get a demo 🔑 Key Lessons 🚀 Launch on platforms before the ecosystem matures: Polly launched on Slack before an app store existed. 80% of users completed a painful 5-step install, proving early movers on viral platforms get compounding distribution. 💰 Separate users from buyers in a freemium SaaS: Most free users picking lunch spots will never pay. The real buyers are comms leaders running company all-hands and sales kickoffs worth 150+ person-hours. 🔄 Build viral loops into the freemium SaaS product: 12% of Polly responders become creators, who send polls to new groups where another 12% convert. This compounding freemium conversion loop drives growth without paid acquisition. 🏢 Diversify across platforms before risk becomes existential: When Slack built Workflow Builder to compete, Bilal had already expanded to Teams, Zoom, and Google Slides. 🧠 Creator pricing beats workspace pricing for horizontal products: Charging only poll creators avoids monetizing casual users who churn. Enterprise tiers shift to monthly active users for simpler administration. Chapters Introduction What Polly does and who it serves Origin story - messaging platforms meet enterprise Launching on Slack before the app store existed Product Hunt viral moment and early growth The freemium SaaS monetization strategy First paying customer - $8/month fantasy football league Separating users from buyers in a horizontal product Free-to-paid conversion challenges When Slack built a competing Workflow Builder feature Building across multiple platforms today Lightning round Resources Full show notes: https://saasclub.io/462 Join 5,000+ SaaS founders: https://saasclub.io/email

Bilal Aijazi

Co-Founder and CEO

Polly

4,000 pound WordPress plugin. No tech skills. No VC funding. 8-figure exit. James Ashford built GoProposal as a bootstrapped SaaS for accountants and sold it to Sage - proving you don't need massive funding to build a valuable company. James reveals the self-funded playbook that took him from business consultant to successful founder, why he printed acquirer logos on his wall before getting his first customer, and the "market like a celebrity chef" strategy that let him dominate online when COVID killed competitor events. GoProposal is a bootstrapped SaaS proposal and pricing platform for accountants that reached 1.5M ARR with 1,100+ customers, a 78 NPS score, and just 12 people before the 8-figure exit to Sage. A profitable SaaS from day one. This episode is brought to you by: 💖 Gearheart → Book a free consult and get the first 20 hours free 📡 Signal House → Learn more and get a demo 🚨 NordStellar → Book a demo and get 20% off with code blackfriday20 🔑 Key Lessons 🚀 A bootstrapped SaaS MVP doesn't need perfect tech: James built GoProposal on a 4,000 pound WordPress plugin that scaled to 1,100+ customers and an 8-figure exit - solving a real problem matters more than sophisticated technology. 🎯 Build your bootstrapped SaaS to sell from day one: Before his first customer, James calculated his freedom number and printed potential acquirer logos on his wall. Every business decision was made with the exit in mind. 🤝 Buy credibility strategically as an industry outsider: James traded 10% of GoProposal for 10% of a respected accounting firm, giving instant insider status and the ability to speak from multiple perspectives. 📚 Market like a celebrity chef - give away your methodology: Gordon Ramsay shares recipes for free, yet people eat at his restaurants. James gave away his entire pricing framework and people still bought the software. 💰 Bootstrap constraints force better strategies than funding: When conferences cost 25K, he hired a full-time videographer instead. When COVID hit, competitors lost events while GoProposal dominated online. Chapters The "Don't Wish It Were Easier" philosophy What GoProposal does for accountants From business consultant to bootstrapped SaaS founder The 4,000 pound WordPress MVP that scaled Trading equity for credibility Writing a bestselling book in 2 weeks Getting the first 100 customers The bootstrapped SaaS marketing playbook The PATH Method: Pain, Aspirations, Traps, How Onboarding: the shock and awe approach Why he skipped conferences for a videographer Preparing for exit from day one The M&A process and due diligence Lightning round Resources Full show notes: https://saasclub.io/461 Join 5,000+ SaaS founders: https://saasclub.io/email

James Ashford

Founder

GoProposal

Usage-based SaaS pricing with no minimums. Customers could scale to zero without leaving. Ryan Wang launched Assembled with a pricing model that let revenue drop to nothing during COVID - even though no one was churning. It took 8 months to earn his first dollar. Ryan reveals the SaaS pricing fix that turned zero revenue into 8-figure ARR, why his team blamed themselves for months before realizing the usage-based pricing problem was macro-driven, and the pricing strategy of adding minimums and building sticky features that prevented future revenue collapses. Assembled is an AI platform for customer support that helps companies manage both human and AI agents. Ryan previously worked as a machine learning engineer at Stripe. The company now generates tens of millions in ARR. This episode is brought to you by: 💖 Sprinto → Book a demo and get 10% off + your first pentest FREE 💖 Gearheart → Book a free consult and get the first 20 hours free 📡 Signal House → Get featured on 150+ podcasts in your niche 🚨 NordStellar → Book a demo and get 20% off 🔑 Key Lessons 💰 SaaS pricing needs minimums to survive downturns: Assembled's pricing model with no minimums let customers scale to zero during COVID, dropping revenue to nothing for 8 months and proving that pricing floors are essential. 🎯 Universal pain points reveal product-market fit: Ryan found PMF when every support leader showed the same messy color-coded spreadsheet for scheduling - proving the problem generalized across companies. ⏳ Plant seeds when there is no harvest in sight: Assembled went 8 months with zero revenue, but Ryan kept meeting customers in person and building around their needs, creating the foundation for 8-figure ARR. 🔧 Filter custom deals by what generalizes: Ryan took Robinhood's custom enterprise deal because those features would scale, but walked away from an airline needing Microsoft Dynamics integration. 🤝 Win one community before scaling channels: Ryan focused on the Support Driven Slack community, building trust until every member looking for workforce management was already "team Assembled." Chapters Introduction Seeds vs. harvest: the founder mindset for surviving zero revenue Founding story: from Stripe ML engineer to Assembled The workforce management problem explained Product-market fit: the color-coded spreadsheet discovery Pandemic launch: TechCrunch and Hacker News on the worst day SaaS pricing mistake: why usage-based with no minimums failed The custom deal filter: build vs. walk away Scaling from 10 to 50 customers with data-driven ICP Community-led growth: winning Support Driven Lightning round Resources Full show notes: https://saasclub.io/460 Join 5,000+ SaaS founders: https://saasclub.io/email

Ryan Wang

Co-Founder and CEO

Assembled