Omer Khan
The SaaS Podcast - Real Lessons on Growing Profitable SaaS
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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SaaS Product-Market Fit: Manual MVP to $100M ARR 05.12.2024 48:53
Tony Jamous launched with $4 million and zero product. Two months later, the pandemic created massive demand - and his team had nothing built. Instead of turning customers away, they used a Wizard of Oz MVP where humans did everything manually behind a software front end. That approach validated SaaS product-market fit and became the foundation for scaling SaaS operations across 180 countries. Ton...
Bootstrapped SaaS: $6M ARR With Just 3 People 21.11.2024 53:04
Three co-founders. No marketing team. No sales reps. No investors. Philippe Lehoux ran a bootstrapped SaaS for almost a decade with just three people and hit $480K MRR. In this episode, you'll learn how Missive reached nearly $6M ARR while staying 100% founder-owned, using versus pages, a custom affiliate program, and a self-funded SaaS discipline that eliminated all fake work. Philippe reveals wh...
Founder-Led Sales: 8 Months of Failure to $10M ARR 14.11.2024 58:59
Palash Soni sent thousands of cold emails and got nowhere for 8 months. His founder-led sales approach kept stalling because he dismissed UI feedback as personal preference. In this episode, you'll learn how a 5-week UI rebuild, landing Drift through startup sales persistence, and a bold pivot at $5M ARR grew Goldcast beyond $10M ARR. Palash reveals how split-testing 200 cold emails between two se...
SaaS Side Project to $1M ARR in 2 Years Solo 07.11.2024 56:49
Will Van Der Sanden spent 8 years building products nobody could understand. Then he built a simple tool for his wife's business as a SaaS side project - and it became a seven-figure Chrome extension with 80,000 customers. In this episode, you'll learn how Dux-Soup hit $1M ARR in just two years using a freemium SaaS model, organic influencer marketing, and relentless simplicity. Will reveals how t...
Open Source Monetization: 40M Users to 8-Figure ARR 31.10.2024 1:00:22
Peter Wang gave away his product to 40 million users without requiring an email address. Then he built an 8-figure business on top of it through open source monetization. In this episode, you'll learn how Anaconda turned Python into the dominant language for data science and monetized the freemium SaaS model by selling to enterprise buyers instead of individual practitioners. Peter reveals how thr...
Niche SaaS: One Pain Point to $5.5M ARR in 12 Years 24.10.2024 54:50
Erling Linde had no sales experience and a product so ugly a prospect called it terrible. Twelve years later, his niche SaaS generates $5.5M ARR and employs 42 people across five countries. In this episode, you'll learn how focusing on one vertical SaaS pain point and expanding geographically - instead of adding features - built a durable business. Erling reveals how he cut demo times from two hou...
Viral SaaS Growth: $1M ARR in 4 Months With No Funding 17.10.2024 1:02:59
Martha Bitar hit $1M ARR in just 4 months - with zero funding and no sales team. Her viral SaaS growth engine at Flodesk combined a "Made in Flodesk" footer on every email sent with an affiliate program that paid $19 per referral, creating a compounding loop that drove explosive adoption. In this episode, you'll learn how to build SaaS without funding and turn unconventional pricing into a competi...
SaaS Content Strategy That Built $70M in ARR 10.10.2024 54:00
Colin Nederkoorn spent 18 months reaching $10K MRR - then compounding did the rest. His SaaS content strategy turned an email list of potential customers into a demand engine that powered Customer.io from $50 MRR to $70M ARR over 12 years. In this episode, you'll learn the content-led growth playbook behind one of the most patient SaaS success stories ever told. Colin reveals how a meeting with Ra...
B2B Product-Market Fit: 5 Years Then Takeoff 03.10.2024 45:22
Dan Uyemura spent five years grinding toward PushPress's first million in ARR. He nearly quit to go back to running his gym. But the B2B product-market fit he built - software made by a gym owner, for gym owners - turned into an 8-figure vertical SaaS serving 3,500 clients. Dan reveals how domain expertise gave him 70% accuracy on gut-based product decisions, why five-minute customer support creat...
SaaS Pricing: Sell Training, Give Software Free 26.09.2024 1:05:59
Todd Dickerson and Russell Brunson launched ClickFunnels expecting 10,000 customers. They got 1,000. Then Russell sold a $997 training course and bundled the SaaS for free - and 45% of the room bought. That SaaS pricing moment changed how they built a $140M ARR business forever. Todd reveals how ClickFunnels bootstrapped from $15K in starting capital to 100,000 customers using a pricing strategy t...
SaaS Retention: Why Firing 40% of Customers Worked 19.09.2024 51:39
Most founders fight SaaS churn by trying to save every customer. Caleb Avery fixed SaaS retention by firing 40% of them. After years in payments consulting, Caleb built Tilled and discovered that only 15-20 of his first 50 customers were succeeding. The rest were dragging the business down. Caleb reveals how deliberate customer retention pruning triggered 500% year-over-year growth, why LinkedIn c...
Serial SaaS Founder: $1M ARR 3 Times, Faster Each 12.09.2024 1:00:26
Adam Robinson bootstrapped three SaaS startups to $1M+ ARR, and he did it faster every time. Robly took 17 months. Retention.com took 27 weeks. RB2B took just 16 weeks. This serial SaaS founder never raised a dollar of outside funding for any of them. Adam breaks down the exact playbook at each stage - from running a call center out of his apartment, to provocative Facebook ads, to building a 92,0...
SaaS Onboarding: 7 Flows That Drive Growth 05.09.2024 1:12:37
Most SaaS founders obsess over getting more signups but ignore the user flows that turn signups into paying customers. Peter Loving has redesigned SaaS onboarding and growth flows for dozens of companies - and one dashboard redesign alone added $300K in ARR by lifting trial-to-paid from 18% to 26%. Peter breaks down 7 critical flows: signup, SaaS onboarding, activation, upgrade, core workflow, int...
Enterprise Sales: From Poverty to 700K Workers 29.08.2024 1:05:13
Jason Radisson grew up in poverty, raised by a 16-year-old single mother on a dirt road in rural Massachusetts. He became a Fulbright Scholar, went to Harvard, joined McKinsey, then built Movo into an enterprise sales machine with nearly 100 customers and 700,000 workers on the platform. Jason reveals how founder-led sales and warm intros at the C-level compressed enterprise sales cycles to 2-3 we...
Selling SaaS Without Sales Experience to 20K Users 22.08.2024 1:00:49
Patrick Barnes expected 4,000 ideal customers to jump on his new Amazon integration. Instead, it got 46 clicks. That kind of humbling moment keeps happening - even when you've figured out selling SaaS without sales experience well enough to reach 20,000 customers and eight figures in ARR. Patrick reveals how he bootstrapped and sold Advocately to G2, then acquired a Shopify app with 2,000 customer...
SaaS Subscription Billing: $20K to $1M ARR 15.08.2024 1:09:55
Jonathan Rhyne was an attorney selling appliances at Sears when he spotted an opportunity to overhaul SaaS subscription billing at a tiny developer tools startup doing just $20K MRR. Learn how switching from one-time licenses to SaaS subscription billing, segmenting customers by size, and charging premium prices for new features grew PSPDFKit to $1M ARR in 8 months. Jonathan reveals how he restruc...
Early Traction: 60 Waitlist Signups to $2M ARR 08.08.2024 1:07:49
Lav Crnobrnja forgot about his landing page for nine months. Then one email from a frustrated waitlist subscriber changed everything. That single message became the early traction signal that turned a company hackathon side project into a $2M ARR bootstrapped SaaS with 2,500 customers. Lav reveals how building Slack-first instead of adding Slack as an integration created a genuine differentiator,...
Bootstrap to Profitability: $1K to $26M ARR 01.08.2024 1:07:01
Guillaume Moubeche launched lemlist with $1,000 and a bootstrap to profitability mindset. Today, lempire generates $26 million in ARR with just 90 people and $10 million in EBITDA. But the path from surviving on pasta to running five profitable SaaS products was anything but smooth. Guillaume reveals how building in public with real cold email results drove 30% month-over-month growth, why warm ou...
SaaS Product Validation: 3 Startups, 2 Exits 25.07.2024 1:07:29
Jake Stein spent six months pitching enterprise customers and got zero conversions. They loved the vision of standardized contracts but wouldn't be the first to adopt. His SaaS product validation journey across three startups reveals why validating SaaS ideas with the right buyer matters more than having the right product. Jake shares how RJ Metrics' SaaS go-to-market took eight years before selli...
Self-Funded SaaS: Side Project to $5M+ ARR 18.07.2024 54:32
Dean Mathews ran his self-funded SaaS as a side project for over a decade - spending just 20 hours a week while consulting full-time. By the time he went all in, OnTheClock had already crossed $1M in annual recurring revenue. Learn how this self-funded SaaS grew to $5M+ ARR with 18,000 customers and zero outside funding. Dean reveals how he validated the idea through forum research without a singl...
SaaS Product-Market Fit: A Year of Wrong Words 27.06.2024 51:33
Michael Zuercher spent a year struggling to explain how Prismatic differed from Mulesoft and Zapier. Every sales call ended with "I don't understand how you're different." Then SaaS product-market fit finally clicked around $1M ARR - and conversations shifted from confusion to immediate understanding. Michael reveals how building 600 integrations at his previous company led to Prismatic, why findi...
SaaS Retention: 8-Figures on Just 2 Channels 20.06.2024 46:36
Kaveh Rostampor bootstrapped a SaaS retention platform for six years, grew it to eight figures in ARR, then raised $50 million - and still hasn't spent it. Learn how Planhat used just two growth channels to reach 8-figure ARR and why SaaS retention became the foundation of their entire business. Kaveh reveals how paid ads targeting department heads with outcome-based messaging about reducing churn...
Building AI Products: Cold Calls to High 7 Figures 13.06.2024 46:28
Zach Rattner forced himself through the door of a moving company for the 18th time, phone in hand, looking for an excuse not to walk in. Building AI products as an introverted engineer meant every cold call felt like torture - and half the people he pitched said his AI startup would never work. Learn how building AI products with LOI validation de-risked a technically ambitious vertical AI startup...
Sales Pipeline: 60 Customers at One Event, New Category 06.06.2024 50:44
Evan Liang spent three years trying to close some of his first deals at LeanData because prospects didn't know his category existed. Paid search was useless - there were literally no keywords to bid on. Building a sales pipeline in a category nobody searched for required a completely different SaaS go-to-market playbook. Learn how LeanData built a sales pipeline through events and customer-led gro...
SaaS Acquisition: 18 Deals to a $60M ARR Portfolio 23.05.2024 43:16
Tim Schumacher has completed 18 SaaS acquisition deals, building a portfolio that generates over $60M in ARR across 300 employees in 33 countries. Most targets are bootstrapped SaaS companies valued between 2x and 3x ARR. Learn what SaaS acquisition buyers actually look for, how earn-out structures push acquisition valuation multiples higher, and why reducing founder-dependency is the most importa...
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