The SaaS Podcast - Real Lessons on Growing Profitable SaaS

Omer Khan
  • 5.0 (32)
  • Entrepreneurship
  • Updated weekly

Building software is easier than ever. Growing it into a profitable business is the hard part. Every week, a founder gets specific about what actually moved the needle: finding product-market fit, landing customers, pricing, defensibility, and durable growth. Host Omer Khan has interviewed nearly 500 software founders, from their first customers to real scale. You get what actually worked, not theory. Lately that includes the honest take on AI: what it changed about building and selling software, and what it didn't. New episodes every week.

  1. 2 days ago

    Rick Knudtson (Workshop): The email signal he ignored for 9 months

    Nine months in. Close to zero customers. He was ready to hand the money back to investors. Rick Knudtson had already sold one company, so Workshop started with the idea he found interesting: an intranet. Customers kept telling him to fix email instead. The rebuild took 30 days and brought in 10 customers. Rick explains why big enterprises cannot run internal comms on a cheap marketing tool, how a year of newsletters and ungated resources filled the pipeline before Workshop had anything to sell, and what changed when the founding team stopped defending its own idea and started listening to customers. Plus: why Workshop dropped per-user fees for audience-based pricing, and how that changed the way customers expand into new departments. Workshop is an internal communications software platform based in Omaha with around 140 employees and just under 1,000 customers, including Capgemini. It is five years old and past $10M ARR. Rick previously co-founded Flywheel, a WordPress hosting platform sold to WP Engine in 2019. This episode is brought to you by: 🤖 Hobbes → Don't book a demo. Take one. 🔑 Key Lessons 👂 The signal was in the sales calls all along: Prospects named email as their biggest internal comms pain for nine months while Workshop kept building an intranet. Listening to customers only started once the ego from a previous exit got out of the way. 🎯 Finding product-market fit was obvious when it finally arrived: Nine months of selling the intranet earned about three customers. Thirty days on the email product brought ten. That gap told the team exactly where to go all in. 🧱 Pick a first problem you can ship fast: An intranet cannot be built iteratively, so feedback loops stall for months. Email analytics was small enough to ship in 30 days and grow into a wider platform. 🔒 Enterprise email is not a MailChimp problem: Security layers, IT governance, and getting a message into 100,000 inboxes in minutes are why large companies cannot run internal comms on an off-the-shelf marketing tool. 📣 Market for a year before you sell anything: Workshop launched a weekly newsletter on day one, now at 50,000 subscribers, alongside ungated resources and monthly webinars that grew from five attendees to five hundred. 💰 Audience-based pricing removes expansion friction: Workshop charges by employee audience size and by channel rather than per seat, so adding another department never triggers a procurement review or a new negotiation. 🧭 Write the mission first and the values later: A broad mission gave the team direction before the product existed. Values waited twelve months so they described what had actually kept the company alive. Chapters How selling Flywheel led to the internal comms idea Writing the mission statement before the product The intranet bet and why it never found a through line Why enterprise email is harder than founders assume Building a newsletter and resource library before selling Nine months, near-zero customers, and the plan to return the money The bar conversation that led to the 30-day email rebuild Ten customers in 30 days and what product-market fit felt like Audience-based pricing and dropping per-seat fees Lightning round Resources Full show notes: https://saasclub.io/493 Join 5,000+ SaaS founders: https://saasclub.io/email

  2. 27 Aug

    Selling Before Building: $1M ARR in Six Months

    Ten thousand ads, all built by hand. Julius Körfgen left that grind to build Uplane, software that automates it, then sold to his first customers before writing a line of code. Uplane reached a million dollars in ARR in about six months. Julius makes the case for selling before building: the cold outreach that got strangers on calls, the one-week sprint from discovery call to working demo, and why he refuses to run a free pilot. Without a dollar attached, he argues, you cannot tell a real business case from a polite conversation. Plus: why Julius threw out per-seat pricing and now charges a share of ad spend, so Uplane only earns more when the customer's campaigns do better. Uplane runs around twenty people across San Francisco and Berlin. Julius and his two co-founders raised their first funding round close to a year before the product existed, AG1 is a customer, and a project with Deutsche Bahn is underway. This episode is brought to you by: 🤖 Hobbes → Don't book a demo. Take one. 🔑 Key Lessons 🤝 Sell before you build: Julius closed customers before writing a line of code. His discovery calls ended with a promise to return in a week with a solution, which forced both a real deadline and a real answer about demand. 🎯 Frame outreach as learning, not selling: His cold LinkedIn messages said he had just left his job and was exploring an idea, and asked for a few questions. People opened up about problems they would never have shared with a pitch. 💰 Never run a free pilot: Without a dollar attached you cannot tell a business case from a polite conversation. Julius has watched founders stay attached to an idea for months because nobody ever asked them to pay for it. ⚡ A week is long enough to build the thing you promised: Three founders and one week produced demos that won real customers. Scrappy was fine; fake was not, and he argues AI removes the excuse for a mock-up that does nothing. 💰 Align pricing with the outcome you claim: Uplane charges a fixed fee covering costs plus a variable share of ad spend. Julius says it makes the pitch easier, because he only earns more when the customer's campaigns do better. 🏢 Be reachable faster than an agency can be: Uplane answers customers within 120 seconds. Julius treats speed of response as the main structural advantage an early-stage company has over an incumbent agency. 🧠 Volume is not the constraint anymore: AI made producing ads nearly free, so the bottleneck moved to picking the roughly ten percent that perform. Companies pushing more output without connecting it to analytics are solving the wrong half. Chapters Introduction What Uplane does and the problem it solves Ten thousand ads by hand Deciding to leave and build it The cold LinkedIn outreach that worked Standing out when everyone uses AI to personalise The first customer Why free pilots are a trap The one-week sprint from call to demo The 120-second response rule Throwing out per-seat pricing Attribution and charging on ad spend Guardrails and atomic content Lightning round Resources Full show notes: https://saasclub.io/492 Join 5,000+ SaaS founders: https://saasclub.io/email

  3. 20 Aug

    Enterprise Sales With No Product: Landing a Big Four Customer

    Two founders. Two engineers. No product. Christian Lund closed one of the Big Four accounting firms as Templafy's first customer before the software existed, by selling a point of view instead of a demo. When that customer asked to start with ten people, he didn't say no. He said "yes, if." Christian breaks down his approach to selling to enterprise without a product, why he answered every ten-person pilot request with "yes, if," and how fixing the proof criteria upfront turned trials into company-wide deals. He also explains why disqualifying prospects beats trying to convince them. Templafy now runs at eight figures in revenue with a couple of hundred employees. Christian and his co-founder spun it out of an on-premise document business, raised their first funding round close to twelve months before the product existed, and are now rebuilding the company again for the AI shift. This episode is brought to you by: 🤖 Hobbes → Don't book a demo. Take one. 🔑 Key Lessons 🏢 Sell your point of view before you sell product: During a technology shift, large enterprises buy people who understand the transition. Templafy won a Big Four firm on domain expertise alone, then co-created the product with them. 🤝 Answer pilot requests with "yes, if" rather than no: Christian never refused a proof of concept. He attached conditions on proof criteria, budget, timeline, and the rollout that follows, and walked away when they were missing. 🎯 Define what you are proving before any trial starts: A POC to see whether someone likes the product proves nothing. Agreeing the exact pass conditions upfront turns a trial into a decision rather than an experiment. ⚡ Setting the criteria shapes the competition: Because Templafy defined the proof points first, prospects who later ran competitive evaluations often used Templafy's criteria to score every vendor in the process. 🧠 Disqualify rather than convince: Christian's team filters for buyers who already accept the market is changing. He argues sales has nothing to do with convincing people, and that defending buyers cost too much time to pursue. 🚀 Land wide, then go deep: Enterprise security and procurement cost the same for ten users or a hundred thousand, so Templafy pushed for company-wide rollouts first and expanded into specific team use cases afterwards. 📉 Being too far ahead is a real cost: Templafy's AI messaging ran ahead of what buyers wanted. Christian's rule is that you can be fifteen percent ahead of the market but not eighty, or you lose the conversation entirely. Chapters Introduction What Templafy does and the size of the business Seeing the cloud shift and spinning out of the on-premise business Two founders, two engineers, and a year of unlearning Selling thought leadership instead of product Targeting 800 people with specific messaging Raising funding twelve months before the product Why every enterprise customer is its own market The ten-person pilot problem "We didn't say no, we said yes if" Writing the criteria your competitors get scored on Disqualification as a sales strategy Resetting the company again for AI: fifteen percent ahead, not eighty Uphill skiers, downhill skiers, and the lightning round Resources Full show notes: https://saasclub.io/491 Join 5,000+ SaaS founders: https://saasclub.io/email

  4. 13 Aug

    Featherless AI: When Your Weekend Experiment Makes More Than Your Startup

    He spent two years building his own AI model. Over one launch weekend, a side experiment out-earned it. Eugene Cheah killed the original product and rebuilt Featherless AI around what customers actually paid for. He explains why he concluded people wanted these models more than they wanted his, and how he made the call to walk away from two years of work. Eugene breaks down how GPU hot-swapping changed the unit economics of AI inference, why he charged a flat monthly rate while the rest of the AI industry billed per token, how stripping the technical explanation off the homepage kept improving conversion, and why Reddit and Discord drove his earliest customers. Featherless AI now provides instant access to more than forty thousand open source AI models, on the way to a target of all three million on Hugging Face. It reached multiple seven figures in ARR within about a year, and has since raised a Series A led by Airbus Ventures and AMD Ventures. 🤖 Hobbes → Don't book a demo. Take one. 🔑 Key Lessons 🔄 Let the experiment beat the plan: Eugene spent two years on his own AI model, then a side experiment made more money than it over one launch weekend. He renamed the company and rebuilt around what customers actually paid for. 🧠 Attachment to your own technology is the trap: The pivot was emotional, not technical. People wanted these models more than his model, and he had been holding his own mission back by insisting it run on his architecture. 💰 Flat pricing sells to the CFO, not the engineer: Per-token billing meant teams could not answer "what will this cost?" A fixed monthly rate removed bill shock and unblocked procurement. 🎯 Removing explanation improved conversion: Featherless kept stripping the technical story off the homepage, eventually removing their own research from the top. Conversion improved each time. 🚀 Go where nobody is competing: The top hundred models have ten providers each. Beyond that, Featherless is usually the only one. A quarter of an uncontested market beat a slice of the crowded top. 🤝 First customers came from where the complaints already were: Reddit's LocalLlama and Ollama communities and Discord were full of people asking how to run models they could not host. ⚡ A constraint you solve for yourself can become the product: They built GPU hot-swapping because they had thousands of fine-tuned models and could not afford thousands of GPUs. That workaround turned out to be the company. Chapters What Featherless AI does and the size of the business Starting as an open source model project One GPU per model, and not enough money Building GPU hot-swapping The weekend the experiment made more money than the platform What they hoped to learn from the experiment Finding demand on Reddit and Discord The mission: AI beyond English and Chinese Realizing he was holding his own mission back Why flat-rate pricing instead of per-token Removing the explanation and improving conversion Hosting the long tail of open source models Competing where no one else is The Series A and what comes next Resources Full show notes: https://saasclub.io/490 Join 5,000+ SaaS founders: https://saasclub.io/email

  5. 23 Jul

    Stuck at $50K ARR for 5 Years. Now $1.5M With 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

  6. 16 Jul

    50 Cents a Pool: The Pricing Model Behind a SaaS Exit

    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

  7. 9 Jul

    He demoted his SaaS to sell a service and 4x'd revenue in 12 months

    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

  8. 2 Jul

    How Danny Jenkins Bootstrapped ThreatLocker From $150K Debt to $200M

    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

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Building software is easier than ever. Growing it into a profitable business is the hard part. Every week, a founder gets specific about what actually moved the needle: finding product-market fit, landing customers, pricing, defensibility, and durable growth. Host Omer Khan has interviewed nearly 500 software founders, from their first customers to real scale. You get what actually worked, not theory. Lately that includes the honest take on AI: what it changed about building and selling software, and what it didn't. New episodes every week.

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