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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Episodes
SaaS SEO: Rand Fishkin on Moz's Path to $29M 28.01.2015 33:04
Rand Fishkin was $500,000 in debt, hiding finances from his own father, and running a consulting firm with his mom. Then he started blogging about SaaS SEO five nights a week - and that strategy turned into a million-member community and a $29M software business. In this episode, the Moz co-founder shares how SaaS SEO content built an audience for three years before he had a product to sell, how h...
SaaS Content Marketing: 7 Years of Failure to 700 Customers 25.01.2015 40:42
Dan Norris spent seven years running a web agency with no profit. Then he burned through his savings on a software startup that topped out at $476 a month. With two weeks of cash left, SaaS content marketing became his lifeline. He emailed the list he had built through SaaS content marketing during his failed software venture, posted in a forum, and launched WP Curve. Ten customers signed up in th...
SaaS Marketplace Pivot: Free to $1M in Revenue 21.01.2015 32:24
Ryan Hamlin spent $400,000 of his own money building a free marketplace for booking events. Then he realized the SaaS marketplace model he needed was hiding inside the product he had already built. PlaceFull started as a consumer-facing booking platform where merchants listed for free and paid only when bookings came in. The problem was that free users had no incentive to keep their inventory upda...
Startup Traction: DuckDuckGo's Bullseye Framework 18.01.2015 32:25
Gabriel Weinberg built DuckDuckGo into a search engine with over a billion searches in 2013. But early on, he was stuck at just 10,000 searches a month - and the startup traction strategy he was using was never going to scale. So he studied dozens of successful founders, from Jimmy Wales at Wikipedia to Alexis Ohanian at Reddit, and unpacked exactly what made their startup traction breakthroughs h...
Competitive Differentiation: DuckDuckGo vs. Google 14.01.2015 33:27
Gabriel Weinberg spent $10,000 to launch a search engine against Google. Every previous competitor had failed by trying to match Google's technology. But competitive differentiation on privacy, not technology, is what made DuckDuckGo work - reaching 250 million monthly searches with just 30 people. In this episode, Gabriel reveals how competitive differentiation shaped DuckDuckGo's entire strategy...
Product-Led Growth: Trello's Path to Millions of Users 11.01.2015 46:51
Michael Pryor and Joel Spolsky spent 15 years building developer tools at Fog Creek Software. Then they created Trello - a product-led growth experiment that millions of people would use, including Google, Adobe, and the New York Times. In this episode, Michael shares how product-led growth shaped every decision at Trello, from targeting 100 million free users with just 1% paying $100 a year, to d...
SaaS Content Marketing: Hiten Shah on KISSmetrics Blog 07.01.2015 57:57
Hiten Shah and Neil Patel lost $2-3 million of their own money on failed businesses before Crazy Egg took off. Then they turned SaaS content marketing into the growth engine behind KISSmetrics, building one of the top marketing blogs on the web. In this episode, Hiten explains how SaaS content marketing started as a Twitter account around the #measure hashtag before becoming KISSmetrics' primary l...
Product-Led Growth: 70K Downloads in 30 Days 04.01.2015 43:50
Baydin launched Boomerang for Gmail with a two-month prototype and got 70,000 downloads in 30 days while still in private beta. Users were so desperate for the product they hacked around invite codes and hosted Chrome extension files on their own servers. That is what product-led growth looks like when you nail product-market fit. In this episode, Aye Moah reveals how a team of just eight people t...
SaaS Co-Founder Clash: Why He Stepped Down 18.12.2014 49:00
Martin Novak and his SaaS co-founder built Visidom with high school friends, bootstrapped it to paying customers, and flew to San Francisco chasing Y Combinator. Then Martin made the hardest call of his startup career - he stepped down. In this episode, Martin reveals how two "CEO types" running one company created confusion for employees, slowed development to a crawl, and forced a painful SaaS c...
Competitive Differentiation That Beat Microsoft Project 14.12.2014 36:31
LiquidPlanner entered the project management market in 2006 when everyone already had Microsoft Project on their desktops. People told them they were crazy. But a single competitive differentiation bet on predictive scheduling - capturing uncertainty with best-case, worst-case estimates - gave them a foothold that incumbents could not replicate. In this episode, CEO Liz Pearce shares how competiti...
Selling a SaaS Business: Why He Left a 7-Figure Company 10.12.2014 30:49
Stu McLaren built Wishlist Member into a 7-figure business powering 54,000 membership sites. Then he did something most founders would never consider - selling a SaaS business while it was still thriving. In this episode, Stu reveals the 2 AM moment at a family camp that changed everything, how two books rewired his thinking about focus and essentialism, and why selling a SaaS business that ranked...
Bootstrap to Profitability: $47 Plugin to 7 Figures 07.12.2014 41:19
Stu McLaren had no coding skills and no funding, but he managed to bootstrap to profitability within months. He sketched mockups in Photoshop, sold a $47 beta to 21 friends in a mastermind group, and watched Wishlist Member grow into a 7-figure business powering over 54,000 membership sites. But the bootstrap to profitability journey nearly ended when his lead developer quit, WordPress released a...
SaaS Pricing Fix: How Charging More Doubled Revenue 03.12.2014 50:40
Rick Perreault thought cheaper SaaS pricing would attract more customers. Instead, Unbounce's $10 and $25 plans were costing $150 per acquisition while those customers churned after just four months. The SaaS pricing model was bleeding money. Rick reveals how Unbounce went from zero to $7.2 million in annual revenue by killing its cheapest pricing strategy tiers, raising average revenue per custom...
Founder-Led Sales: How Close.io Hit 7 Figures 30.11.2014 57:29
Steli Efti dropped out of school at 17, flew to San Francisco with a one-way ticket, and asked a stranger at SFO how to get to Silicon Valley. Five years and one failed startup later, his team's internal sales tool became Close.io - built on founder-led sales hustle that generated seven figures with just six people. Steli breaks down how Close.io pivoted from an outsourced sales services company t...
SaaS SEO Strategy: Blog to Six-Figure Software Sales 23.11.2014 47:07
Spencer Haws spent $5,000 on a cheap developer to build his first software product. It broke after two weeks. He started over, invested $30,000 more, and turned a 1,000-person email list into a six-figure business using SaaS SEO strategy on his blog NichePursuits.com. Spencer reveals how his SaaS SEO strategy grew his email list 3-4x between launches, why his relaunch did 3x the sales of his first...
SaaS Lead Generation: Agency to 350K Users, Zero Ads 19.11.2014 54:14
Jim Belosic stopped paying his mortgage so he could make payroll. That bet turned a small design agency into ShortStack, a SaaS lead generation platform with 350,000 users and revenue approaching eight figures - with zero dollars spent on advertising. Jim shares how he spotted a repeatable pattern in agency client work, built an internal tool for SaaS lead generation campaigns, then opened it as a...
Self-Funded SaaS: $85K to Multi-Millions With Olark 16.11.2014 48:51
Ben Congleton built his first company in high school, pulling in $170,000 a year from a web hosting business before he could drive. His next act was even bigger - a self-funded SaaS that grew to multi-millions with only $85,000 in outside capital. Ben shares how Olark went from a side project he funded with consulting work to a self-funded SaaS live chat platform serving 5,000+ customers in 151 co...
Bootstrapped SaaS: From a $9.95 Spreadsheet to $5M 12.11.2014 40:08
Jesse Mecham built a budgeting spreadsheet in 2004 because he was too broke to pay rent. Nobody bought it at $9.95, but when he doubled the price to $19.95, his first sale came that same day. That bootstrapped SaaS spreadsheet became You Need a Budget (YNAB), now a profitable SaaS generating $5M a year. Jesse shares how he grew this bootstrapped SaaS by teaching first and selling second. A 9-day e...
Launching a Marketplace: The Playbook Behind 4 Wins 09.11.2014 40:45
Matt Mickiewicz built his first online marketplace at 15 years old, paying for his domain registration out of his allowance. By 30, he had used the same playbook for launching a marketplace four separate times - SitePoint, 99designs, Flippa, and Hired - and landed on the Forbes 30 Under 30 list. Matt reveals why every marketplace launch was born from watching user behavior inside an existing commu...
Niche SaaS: From a $300 PDF to Six-Figure Revenue 05.11.2014 53:12
Brecht Palombo had no technical background and no funding. He was a real estate auctioneer who saw an opportunity hiding inside public financial data from 14,000 banks. His first product was a PDF report he sold for $300. That niche SaaS bet turned into BankProspector, a six-figure business he runs from the road. Brecht shares why targeting a niche SaaS market too small for big competitors gave hi...
SaaS Go-to-Market: Tested 5 Ideas, Built the Winner 02.11.2014 53:24
Josh Ledgard and his co-founder had 50 business ideas. Their SaaS go-to-market approach was to build landing pages for each one, drive traffic, and let the data pick the winner. The winning idea got 2x more signups than anything else - and it was the landing page tool itself. KickoffLabs launched in 2011 and made just $8,000 in the first six months. But Josh executed a relentless SaaS go-to-market...
Bootstrapped SaaS Growth: Guest Blogging to $8M ARR 29.10.2014 52:34
Paras Chopra had a $1,000 per month salary and a goal to match it with his SaaS side project. Two months after quitting his job, Visual Website Optimizer brought in $4,000 in its first month - four times his target. This bootstrapped SaaS growth story took him from Delhi to $8M ARR. Paras shares how he achieved bootstrapped SaaS growth by writing educational guest posts for Smashing Magazine, runn...
Pricing Strategy That Went From $2.50 to 8 Figures 27.10.2014 47:39
Adam Schoenfeld once charged $2.50 for 48 hours of access to his SaaS product. Within two years, his pricing strategy shifted to a $500/month minimum and enterprise brands like Pepsi and Microsoft were paying far more. That pricing strategy evolution changed everything for Simply Measured. Adam reveals how he applied hard lessons from a failed startup to build an 8-figure social analytics business...
SaaS Content Strategy: 100K Customers, No Sales Team 22.10.2014 42:44
Chris Savage spent a full year building Wistia before landing a single customer. He lived in a 10-person house, worked 90-hour weeks, and considered getting a Starbucks job for health insurance. Then he discovered that SaaS content strategy could replace his entire sales function. Wistia grew from zero to over 100,000 customers without ever hiring a salesperson. Chris reveals how his SaaS content...
Freemium SaaS Playbook: From Free to 1M Users 18.10.2014 39:08
Kirk Simpson built a freemium SaaS product in a market where 70% of potential customers were still using spreadsheets and shoeboxes. Within three years, Wave had over a million users across 200 countries - all on a freemium model where the core product was completely free. Kirk reveals how a $5 Google Chrome Store listing drove 210,000 signups, why going free does not excuse a bad product, and the...
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