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The SaaS Podcast

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Browse by topic:All Bootstrapping First Customers AI-Powered SaaS Product-Market Fit Enterprise Sales Product-Led Growth Pricing & Monetization Founder-Led Sales Positioning & Differentiation Churn & Retention Content & Inbound Marketing Exits & Acquisitions Fundraising

Ev Kontsevoy, Teleport

The 8-Figure Open Source SaaS Playbook

Ev Kontsevoy is the co-founder and CEO of Teleport, an infrastructure identity platform based in Oakland, California. Teleport helps organizations manage secure access to their computing environments by unifying human, machine, and AI agent identities into a single layer. Before Teleport, Ev founded Mailgun in 2009, an email API for developers that was acquired by Rackspace in 2012. After the acquisition, he spent time at Rackspace listening to customer problems, which led him to start Gravitational in 2015. The original product, Gravity, helped SaaS companies deploy their applications across multiple cloud environments. But the real open source SaaS story started when Ev built Teleport as one component of Gravity - a free, Apache-licensed tool for managing secure access. He intended it purely as demand generation for the paid Gravity product. Then COVID hit. Gravity's pipeline dried up overnight while Teleport's inbound demand exploded as engineers scrambled for remote access solutions. The pivot was not really a pivot. Ev focused on one product, rebranded the company as Teleport, and launched an enterprise version. The first enterprise deal closed on an improvised phone call for $25,000 per year. Early on, they sold to individual engineers through a product-led open source SaaS motion. But when Ev asked customers to "sell Teleport back to me," he discovered they were using only a fraction of the platform. They were selling to the wrong buyer. Switching from practitioners to VPs of platform engineering nearly tripled the average deal size in a single year. Teleport now serves over 500 customers in eight figures of ARR, with AI agent identity emerging as a major growth driver - what Ev calls "COVID 2.0" for the business.

Karel Papik, Product Fruits

The Risky AI SaaS Rebuild That Broke a $2M ARR Ceiling

Karel Papik is the co-founder of Product Fruits, a digital adoption platform based in Prague, Czech Republic. Before SaaS, Karel spent 15 years building video games - shipping 16 titles, many of them for women - where he mastered the art of SaaS onboarding and user engagement through psychology rather than tutorials. When Karel met his co-founder Ladislav Salom, Product Fruits had just six customers. Within 12 months of their first investment from Lighthouse Ventures, they grew to $50K MRR using paid search as their primary acquisition channel. They achieved a 24-25% free trial conversion rate by applying product-led growth principles and gaming psychology to their own SaaS onboarding experience. But around $2M ARR, growth hit a wall. The product had become too complex for self-serve SaaS onboarding, and PLG stopped being effective. Meanwhile, AI-powered competitors were emerging fast. Karel describes this as the moment they stopped "riding the horse" and started "riding the tiger." In a gutsy move, Karel emailed investors to say they were pausing feature development on the existing platform to rebuild it from scratch around AI. The investors responded by asking how much more money they needed. The result is an AI copilot that handles discovery calls, tailors onboarding flows, prevents churn, and resolves 80% of support tickets automatically. Today Product Fruits has over 1,300 paying customers - including KPMG, universities, and stock exchanges - with a 25-person team generating millions in ARR. Karel shares lessons on why PPC worked when most founders say it doesn't, how gaming psychology applies to SaaS onboarding, and why he believes talking to customers too much can hold you back.

Girish Redekar, Sprinto

3 Years of Nothing. Then Product-Market Fit Hit Twice.

Girish Redekar is the co-founder and CEO of Sprinto, an autonomous compliance platform that helps companies prove they're handling data securely. Before Sprinto, Girish and his co-founder spent two to three years trying to build their first startup. They had no programming background, so they taught themselves to code at 28 because they couldn't afford to hire developers. The first few ideas went nowhere. A job search engine. A resume matching tool. None of them got traction. Then they built RecruiterBox, a simple CRM for hiring. It launched before Stripe even existed, so their payment system was absurd. Customers had to click a PayPal link, swipe their card, and get credits that depleted daily. When the credits ran out, they'd go back to PayPal and swipe again. It was terrible. But customers kept doing it anyway. That was the clearest signal of finding product-market fit Girish had ever seen - not from analytics or feedback forms, but from watching people jump through hoops to keep paying. They bootstrapped RecruiterBox to over 2,500 customers and single-digit millions in ARR. Then they sold it. Not because it was failing, but because it got too comfortable. They felt like they were the bottleneck, and the business would grow faster in someone else's hands. The second time around, Girish took a completely different approach to finding product-market fit. He'd experienced the pain of SOC 2 compliance firsthand at RecruiterBox, spending months and tens of thousands of dollars on consultants. So when he started Sprinto, he made a rule - no code until the idea was validated. He used The Mom Test framework, ran 15-20 customer interviews, and then paid auditors to audit his non-existent company. Ten times. Each audit, he built a little more product behind the scenes. By the tenth, he knew exactly what to build and had confirmed the consulting service could actually become software. For go-to-market, Girish tried 20 different channels. Seventeen failed. The three that worked were founder communities (Slack groups, WhatsApp groups), VC portfolio programs with startup discounts, and Google (paid + SEO). His framework - harvest existing demand rather than create new demand - helped him focus on places where people were already looking for solutions. Now AI is changing the game from three directions at once. It's changing Sprinto's product, it's changing how customers operate internally, and it's creating new security threats from the outside. The problems that didn't exist two years ago are now driving a whole new wave of demand. Today, Sprinto generates eight-figure ARR with over 3,000 customers across 75 countries. The team has grown to 350 people and they've raised $32 million.

Sylvestre Dupont, Parseur

AI Took Over His Market. His Bootstrapped SaaS Grew 60%

Sylvestre Dupont is the co-founder and CEO of Parseur, a platform that automates data extraction from emails, PDFs, and spreadsheets. The idea started with a side project in 2015. Sylvestre wanted to build a travel map that auto-updated from booking confirmations. He and his co-founder Sylvain, a senior Python developer he'd known for 25 years, saw a bigger opportunity: a general-purpose document parsing tool. They put up a landing page, ran Google Ads, and collected 50 email signups. That felt like enough validation. So they spent the next year heads-down coding. Full features, payment system ready, zero marketing. In December 2016, they launched on Product Hunt and Hacker News. Nothing happened. They emailed the 50 people from a year earlier. Two signed up and quit immediately. So they started from scratch on the marketing side. They began answering questions on Quora, genuinely helping people with document automation problems. That's where their first real customers came from. They also dropped the price from $49 to $9 a month just to get anyone to try it. What set them apart was simplicity. Competitors required users to write complex extraction rules by hand. Parseur let you visually highlight what you wanted. Setup took 10 minutes instead of two hours. That bootstrapped SaaS advantage - simple, self-serve, no sales call required - became the foundation of everything. Growth came slowly through SEO and a Zapier integration that converted at 20 to 30 percent. For the first five years, it was just the two of them. No employees, no investors, no board. Then AI changed the game. ChatGPT could do basic document parsing. VC-funded competitors like UiPath and ABBYY were spending hundreds of millions on AI. Sylvestre had to rebuild his entire product around machine learning - funding the transition from customer revenue, not investors. His bootstrapped SaaS strategy for survival: don't try to out-feature the giants. Be the tool that any business can set up in minutes without talking to sales. Simplicity as a moat, not technology. Today, Parseur generates seven-figure ARR with close to 1,000 paying customers in over 70 countries. A bootstrapped SaaS, still six people, still 100% founder-owned - and still growing.

Hewitt Tomlin, TeamBuildr

How a Vertical SaaS Hit $10M ARR With Flat Pricing

Hewitt Tomlin and his co-founder James started TeamBuildr as a social app for college athletes. A single conversation with a campus strength coach changed everything. The coach didn't want a social experience for his players. He wanted better tools for his actual job - building and distributing training programs. That pivot turned TeamBuildr into a vertical SaaS company built around one job function: strength and conditioning. Hewitt worked a full-time job for the first three years while moonlighting on TeamBuildr, growing revenue from $20K to $100K. When he went full-time, revenue jumped from $100K to $500K and then to $1M. Today TeamBuildr is a $10M ARR business with 45 employees. They've never raised funding and still use the same operating agreement from 2012. About half their customers are high schools, and they deliberately charge pro teams the same price as everyone else. Hewitt's reasoning is pragmatic. As a bootstrapped company, they couldn't afford to build different products for different verticals. By keeping pricing flat, they got NFL and college logos as social proof that drove volume in the high school market - the segment that actually moves the needle for growth. On AI, Hewitt is taking the opposite approach from his main competitor Volt, which is building AI-generated workouts to replace coaches. Hewitt believes AI should enhance the coaching profession, not replace it. He's focused on using AI internally to help his team work better and building AI features only when coaches actually ask for them - which they haven't yet. In this conversation, Hewitt shares how he built relationships with early customers instead of just handing out logins, why he thinks founders who plateau at $500K have a product-market fit problem, and how building for a job function instead of a vertical unlocked every segment from high schools to pro sports.

Sarah Ahmad, Stable

How to Validate a SaaS Idea With Zero Code

Sarah Ahmad and her co-founder Colin met freshman year of college and moved to San Francisco to work as engineers. They quit their jobs to build Mistro, a platform providing benefits for remote teams internationally. They got into Y Combinator's Winter 2020 batch, raised a pre-seed round, and had paying customers. Then COVID hit. You'd think a remote work tool would thrive when the entire world went remote. Instead, it was silent. They couldn't even give the product away for free. COVID had pressure-tested their product-market fit and exposed the truth - nobody needed what they were building. Sarah went back to basics. She ran discovery conversations with hundreds of operations managers and founders. One problem kept surfacing: companies without physical offices didn't know what to do about their business address and physical mail. The incumbents in the space had been around since the 2000s with clunky software. Nobody was raving about them. Instead of making the same mistake again - building a full product before validating demand - Sarah took a completely different approach to SaaS product validation. She posted a simple landing page in the YC community. The response was immediate. Dozens of founders emailed saying they needed it tomorrow. The first version of Stable was embarrassingly manual. A mail partner in San Francisco, Google Drive for document storage, Zoom for onboarding, and a Stripe link for payment. Sarah was manually emailing customers when mail arrived. They ran it this way for the first 100 customers before writing any code. Today, Stable is the leading AI-powered virtual mailbox for businesses with over 10,000 customers, 8-figure ARR, and a team of 50-60 people. They operate in 20+ locations across the US with processing centers in the Bay Area, New York, and Dallas. Their customers range from solopreneurs to enterprises like DoorDash, Realty Income, and GitLab. In this conversation, Sarah shares how the SEO playbook that built the business stopped working when AI overviews took over Google search results, why physical operations are her moat against AI disruption, and the moment she had to shift from product building to company building.

Zhong Xu, Deliverect

Why SaaS Distribution Matters More Than Your Product

Zhong Xu is the co-founder and CEO of Deliverect, an operating system for restaurants that connects digital sales channels like Uber Eats, DoorDash, and Grubhub into one place. Zhong's father immigrated from China to Belgium with nothing. He washed dishes in a Chinese restaurant, saved enough to open his own, and taught himself C++ from a book so he could build his own point-of-sale system. He pushed Zhong into the business early. By 14, Zhong was helping run the restaurant. By 16, he was building websites for Chinese restaurants across Belgium. By 18, he'd built over 1,000 of them. He went on to study software engineering and built one of the first iPad POS systems. He coded the whole thing himself over nine months while working full-time with a three-and-a-half-hour daily commute. In 2014, that company merged with Lightspeed. Five years later, Lightspeed IPO'd. But Zhong wasn't done building. He kept hearing the same thing from restaurant owners. Delivery platforms were taking over. Orders were pouring in from five or six different apps, and nobody had a way to manage it all. So in 2017, he left and started Deliverect. This time, he didn't spend nine months coding before talking to customers. He went out and signed up 50 to 100 restaurants first. Behind the scenes, his team was processing orders manually. It looked automated. It wasn't. But it proved the demand was real before they wrote a single line of code. Then he figured out the SaaS distribution channel that would change everything. Instead of signing restaurants one by one, he partnered with POS companies. Ten partners each bringing in 100 restaurants a month beat doing it alone. When COVID hit and restaurants scrambled to go digital, Deliverect was exactly what they needed. They opened 10 new offices in a single quarter to get ahead of local incumbents. Today, Deliverect serves over 80,000 restaurants across 50 countries with 450 employees. They've processed over $25 billion in orders and are approaching $100 million in ARR. And now Zhong is racing to build an AI intelligence layer for restaurants before the whole industry gets commoditized. Because as he puts it, infrastructure alone is forgettable - the value is in the SaaS distribution channel that controls the intelligence.

Joel Griffith, Browserless

$200 First Customer to $4M ARR Bootstrapped SaaS

Joel Griffith is a jazz trumpet player who taught himself to code. Before building his bootstrapped SaaS, he went through five or six failed B2C business ideas. Then he had a realization - the problems he understood best were the ones he dealt with every day as an engineer. The idea came from a side project. He was building a wishlist app and needed to pull product data from retail websites. That meant running a browser in the background to load pages and extract content. It was a nightmare. The browser would crash, run out of memory, and nothing worked reliably. He went to GitHub and sorted issues by most commented. They were all engineers struggling with the same thing. So he pivoted. Instead of building the wishlist app, he'd build the infrastructure to make browsers work reliably for developers. His first customer paid $200 a month. Total infrastructure cost was $50. He was profitable from day one. But growth was painfully slow. He ended his first year at about $1,000 in MRR. It took three years of working nights and weekends, writing blog posts, answering questions on forums, and building in public before he hit $500K in ARR. Even then, he waited an extra six months because COVID hit and he wanted a safety net before going full-time. He ran the business solo, getting to $60K in MRR as a one-person operation. But he eventually hit a wall - he didn't know how to hire, sell, or build a team. So he partnered with a small firm called Polychrome to handle the operational side of the business. Then AI changed everything. Joel had spent years building infrastructure for web scraping and testing. Now AI agents needed browsers to navigate websites, fill out forms, and interact with systems that don't have APIs. A whole new category of demand showed up almost overnight. Today, Browserless is approaching $4 million in ARR with a team of under 10 people. Joel has never raised a dollar. His bootstrapped SaaS survived Google Cloud and a $60M-funded competitor entering his space - his growth didn't even flinch because eight years of content and community had built something no amount of funding could replicate overnight.

Vineet Jain, Egnyte

How $6K in SEM Launched an Enterprise Sales Machine

Vineet Jain is the co-founder and CEO of Egnyte, a content collaboration and security platform for mid-market and enterprise businesses. Vineet arrived in the US with $100 and no connections. He spent four and a half years at KPMG learning to sell to everyone from line managers to CEOs. That convinced him he could build something of his own. In 2001, right after the dot-com bubble burst, he co-founded Valdero, a supply chain software company, and raised $7.5 million from Kleiner Perkins. Revenue grew quickly. Then Oracle and SAP moved in. Pricing pressure crushed them. They sold. Investors made money. The 70 employees didn't. That failure stuck with him. In 2007, Vineet and three co-founders rented a small office. No funding. Two did consulting while the other two wrote code. The idea: move the physical file server to the cloud. When they launched, analysts lumped Egnyte in with Box and Dropbox - hundreds of companies chasing the same market. Everyone told Vineet to do freemium. His board pushed back. Analysts questioned how they were different. Vineet Jain built Egnyte to over $300 million in enterprise sales revenue using three strategies: charge from day one, offer hybrid cloud when everyone said go cloud-only, and keep cost of acquisition low with inside sales offices in cities like Spokane and Raleigh instead of Silicon Valley. In 2016, Gartner named Egnyte a leader - a tiny company standing alongside competitors that had raised billions. Today, Egnyte has 23,000 customers, 1,400 employees, and has raised just $137.5 million with no additional funding since 2018.

Adam Markowitz, Drata

He Sold a Vitamin for 7 Years Then Found Product-Market Fit

Adam Markowitz is the co-founder and CEO of Drata, a trust management platform that helps companies automate compliance, security assurance, and third-party risk management. Adam never planned to be a founder. He wanted to be an astronaut. That led him to aerospace engineering, and in 2008 he landed his dream job working on NASA's Space Shuttle program. Three years later, NASA retired it. So he taught himself to code and built Portfolium, a platform that helped students prove their skills with real project work instead of resume bullet points. It took years, but he eventually got it into over 500 universities. The company was acquired for $43 million. But it was during those long university sales cycles that Adam experienced a moment he never forgot. A CIO at the largest four-year public university system in the country asked him to prove his company's security posture. He couldn't. His entire company was built on the idea of proving things with evidence - and here he was, asking a customer to just take his word for it. That pain became the seed for Drata. After Portfolium's acquisition, Adam got the band back together - same co-founders, same early engineering team. They spent six months building the first version, talking to dozens of companies and auditors to validate the problem before writing code. Then they did something most founders wouldn't: they refused to sell to anyone until they'd used their own product to get SOC 2 compliant first. When they finally launched, product-market fit was immediate. Adam signed 100 customers in six weeks and 1,000 within the first year. The difference from his edtech days was stark - he'd gone from selling a vitamin to selling a painkiller. Adam used three strategies to accelerate Drata's growth to $100M ARR: 1. Dogfooding before selling - using Drata to earn their own SOC 2 gave instant credibility 2. Building an Auditor Alliance that kept auditors independent while making audits faster 3. A "give before you take" AWS partnership that made Drata a top 5 ISV on Marketplace by bringing thousands of new customers to the platform Today, Drata has over 8,000 customers across 60 countries, more than 600 employees, and crossed $100 million in ARR before its fourth birthday. The company has raised over $300 million.

Gilles Bertaux, Livestorm

How Livestorm Lost Product-Market Fit at $9M ARR

Gilles Bertaux is the co-founder and CEO of Livestorm, a webinar platform for enterprise marketers. In 2016, Gilles and his three co-founders built Livestorm as a university project. They had two months to build a product, get some users, and present it to a panel. So they built a browser-based webinar tool. On presentation day, they livestreamed all the student presentations. Hundreds of people watched remotely. And they loved it. Even former bosses from internships told them to skip the job hunt and pursue this full-time. They were young with no real responsibilities. So they went for it. They spent weeks collecting leads and hosted a launch webinar to showcase the product. It was a disaster. Gilles tried to bring a marketing exec from a big e-commerce company on screen. Instead, his CTO popped up and said 'I think there is a bug.' Live. In front of everyone. Growth came slowly through SEO, Quora, and partnering with bigger companies to get in front of their audiences. No outbound. No sales team. Gilles wrote three to four articles a day and answered questions on Quora that nobody else was touching. For five years, Quora alone drove 10-15% of total organic traffic. Then COVID hit. In one year, Livestorm went from $2 million to $9 million in ARR. But it was chaos. Support tickets jumped from 200 to 20,000 per month. Servers crashed for an entire day. They had to throw money at AWS just to keep things running, and their margins got crushed. After COVID, things got even messier. They tried building a meeting product, then a sales demo product. Suddenly Livestorm looked like a smaller version of Zoom. Customers had no compelling reason to pick them instead. Livestorm had lost product-market fit. In 2022, they tried to raise a Series C. Investors said no. So Gilles had to flip the company to profitability. That meant going after bigger customers who would pay more and stick around longer. But his sales team only knew how to handle inbound leads. He had to replace almost the entire team. Gilles rebuilt Livestorm's product-market fit by narrowing to enterprise webinars for European marketers in banking and pharma - a niche that most founders would run from. There were moments where he wondered if the product could really make the leap. Part of him questioned whether Livestorm's best days were already behind them. Today, Livestorm generates nearly $20 million in ARR with 3,500 customers and has raised $35 million.

Adam Fard, UX Pilot

How a Bootstrapped SaaS Hit $5.3M ARR in Under 2 Years

Adam Fard is the founder of UX Pilot, an AI platform that helps product design teams create and ship great user experiences faster. In 2023, Adam was running a successful UX agency when ChatGPT and LLMs started taking off. He began experimenting with ways to apply AI to his team's design processes and built a Figma plugin that helped users work through UX frameworks and activities. Then during a user interview, someone asked a simple question: "I have all these ideas on my canvas, but can I turn them into something visual? Can I create a wireframe?" That question stuck with him. He started looking around to see if any tools could actually generate wireframes from text input. He found a few products claiming to do it. But when he tested them, he realized they were faking it. They were just swapping existing templates and personalizing the copy. None of them could truly generate a layout from scratch. There was a technical reason for that. Creating wireframes with AI was genuinely hard. So Adam started working on it himself. He explored fine-tuning LLMs, hired AI researchers, and tested component-based approaches. He spent four or five months iterating. Slowly, things started working. The outputs became stable enough to use. He added Figma integration so designers could bring wireframes into their existing workflow. Within six or seven months of that original user question, UX Pilot hit $10K MRR. But growth created a new problem. Adam hired too slowly. At $30K MRR, he kept questioning whether this was the ceiling. He added one engineer, waited, added another, waited again. Looking back, he says he should have hired five people at once instead of dragging out the process. Adam built a bootstrapped SaaS that now generates over $5 million in ARR with a team of 30 and over 15,000 paying subscribers. He proved that a bootstrapped SaaS can compete with well-funded competitors by focusing narrowly on one hard problem - AI wireframe generation for professional design teams - and shipping a code-first product that enterprise teams actually wanted.

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About the Podcast

The SaaS Podcast features in-depth interviews with proven SaaS founders and industry experts. Hosted by Omer Khan, each episode covers real strategies for building, launching, and scaling SaaS businesses.

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