The SaaS Podcast: How B2B SaaS & AI Founders Get Customers

By Omer KhanBusiness Entrepreneurship Technology

The SaaS Podcast: How B2B SaaS & AI Founders Get Customers episodes

March 03, 2016Vertical SaaS: $0 to $70K/Month for Music Teachers
Brandon Pearce spent four years building a vertical SaaS and was only earning $1,500 a month. Today, Music Teachers Helper does $70,000 in monthly recurring revenue - and Brandon runs it while traveling the world with his wife and three daughters. He started the product in 2004 as a hobby project to track his own piano students.
For the first four years, Brandon worked on this niche SaaS part-time while holding a full-time programming job. Going full-time in 2008 was the inflection point that drove growth from $1,500 to $70K/month. His industry-specific SaaS now has a 25-person remote team spread across multiple countries.
Brandon first appeared in The $100 Startup by Chris Guillebeau. His secret to running a niche market SaaS from the road: hire customers as support reps, automate everything possible, and build a management team that can operate without the founder.
🔑 Key Lessons
🎯 Going full-time is the vertical SaaS inflection point: Music Teachers Helper grew slowly for four years at $1,500/month while Brandon worked part-time. Going full-time unlocked faster product development and marketing that drove growth to $70K/month.
💰 Hire your customers as support reps for vertical SaaS: After a call center failed, Brandon offered support positions to existing users at $1.50 per email. They understood the product deeply, and eight years later they remain the best support team.
🧠 Customer surveys cure founder burnout: When Brandon wanted to sell the business in 2011, he sent a survey asking teachers why they teach. The heartfelt responses reconnected him with the impact of his product.
📉 Print ads in vertical SaaS markets can be a waste: Brandon spent $1,000 per ad in music teacher magazines with nearly zero trackable response. Word of mouth and conference booths consistently outperformed paid advertising.
🔄 Build systems so the vertical SaaS runs without you: Brandon created manuals for every role, automated repetitive tasks, and hired managers - enabling him to work 4-15 hours per week while traveling 30 countries.
Chapters
Introduction
Brandon's family travel lifestyle
Homeschooling and world schooling
What drives Brandon - creativity and a Howard Thurman quote
From piano teacher and programmer to founder
How the Music Teachers Helper idea started
It started as a hobby project for himself
Building with PHP as a beginner
Launching the business in 2004
Getting the first customers through word of mouth
SEO and early marketing tactics
Why $1,500/month was motivating enough to keep going
Building a business that runs without the founder
From $30K to $70K/month MRR
Going full-time in 2008 as the inflection point
Team retention and hiring customers as support reps
Marketing - print ads vs word of mouth vs conferences
Dealing with burnout after years of building
How customer surveys cured burnout
Lightning round begins
Resources
Full show notes: https://saasclub.io/104
Join 5,000+ SaaS founders: https://saasclub.io/email
51 min
January 21, 2016Startup Go-to-Market Strategy: 124K Sites by Going Deep
B Byrne was 24 years old when his go-to-market strategy helped Clef reach 124,000 websites. The secret: go deep in small communities instead of chasing a broad audience. Clef replaced passwords with phone-based two-factor authentication but faced a brutal chicken-and-egg problem. B solved it with a niche-first SaaS go-to-market approach - earning trust through personal relationships before expanding.
A manufactured "Petition Against Passwords" PR stunt opened doors at the New York Times, which published a review calling the product "magical." The GTM SaaS lesson: that article did not drive immediate signups, but within a month the credibility effect kicked in and word-of-mouth growth accelerated.
B also open-sourced Clef's employee handbook and shares why he believes HR is the most overlooked function at startups. His launch strategy combined community depth, PR credibility, and transparent culture to build trust in a market where trust is everything.
🔑 Key Lessons
🎯 Go deep in niches with your go-to-market strategy: Clef targeted clusters of websites sharing the same users, getting adopted on five sites each user visited daily rather than one site for many users - creating genuine daily value that drove word-of-mouth.
🤝 Manufactured PR stunts can unlock real credibility: The "Petition Against Passwords" was a fabricated campaign, but it opened doors with NYT reporters who later published a review that transformed Clef from unknown to trusted product.
🧠 Credibility drives growth more than traffic: The NYT article brought traffic but few signups. The real value came a month later when users had a reference point to share with others, proving trust compounds over time.
🔄 Two-sided marketplaces need a niche-first go-to-market strategy: Clef solved the chicken-and-egg problem by concentrating on small communities where they could get both sides to adopt, rather than trying to grow users and websites simultaneously.
🛠️ Open-sourcing internal processes attracts talent: B published Clef's employee handbook publicly, and candidates applied specifically because they could see the company's culture and values before interviewing.
Chapters
Introduction
B Byrne's background and why Oakland
What drives B - learning faster than ever
How Clef works - replacing passwords with cryptography
The origin story - LinkedIn breach and Adobe experience
From tinkering to a real company
Raising friends and family funding
The explosive growth year of 2014
How the New York Times article happened
Why the NYT piece drove credibility not signups
What happens when you forget your phone
The Medusa problem - solving one creates two more
Going deep in small communities vs going broad
Team size and hiring the first employee
Why B became CEO at 24
Building culture and values from day one
Writing and open-sourcing the employee handbook
Why HR is an afterthought at startups
Lightning round begins
Resources
Full show notes: https://saasclub.io/103
Join 5,000+ SaaS founders: https://saasclub.io/email
46 min
January 13, 2016Selling a SaaS Business: $400 to a $43M Exit
Stuart Crane and his co-founder started with $400 and spent 20 years building a business worth selling. When it came time for selling a SaaS business, two deals fell through before they hired an investment banker who ran a competitive bid with 40-50 buyers. The result: a $43 million SaaS exit in July 2013.
The story starts in 1991 when Stuart met his backyard neighbor Jeff, a nurse drowning in paper documentation. Stuart was a database consultant. Within a week, they were building software together. They formed a company with $400 in seed capital and started selling at $4,996 per license using FedExed floppy disks with 30-day trials.
The startup acquisition process taught Stuart hard lessons. Two failed exit strategy attempts meant years of frustration. But the competitive bidding process that followed attracted serious buyers and maximized valuation. The business was profitable from year one, generating $700K-$900K on minimal expenses.
🔑 Key Lessons
🎯 Niche dominance is the key to selling a SaaS business: Definitive Homecare Solutions became the dominant player in home infusion pharmacy software by staying focused on one vertical for 20 years, making the company an obvious acquisition target.
💰 A $400 startup can reach a $43M exit without funding: Stuart and Jeff bootstrapped from day one, reinvesting profits to grow to 80 employees and acquiring two competitors - proving patience and profitability replace venture capital.
🤝 Trial-driven sales create switching costs that close deals: The 30-day floppy disk trial let prospects enter real patient data. When the trial expired, customers had built their workflow around CPR+ and bought immediately.
🔄 Failed attempts at selling a SaaS business teach you to run a better process: After two failed deals, Stuart hired an investment banker who created urgency and competitive bidding for the eventual $43 million sale.
🧠 The golden goose philosophy sustains long-term value: Stuart's framework of protecting product quality, employee well-being, and customer relationships kept the business profitable and attractive enough to command a $43M price.
Chapters
Introduction
Stuart's motivational quote from Jim Rohn
What becoming a millionaire makes of you
How the CPR+ idea started with a neighbor
From consulting gig to software company
Securing intellectual property ownership
Selling the hospital a $1 license
Starting the company during a recession
Pre-internet marketing with physical mailers
The FedEx evaluation packet strategy
How the 30-day trial floppy disk closed deals
When the story seemed too good to be true
Dealing with critical healthcare software bugs
The real impact of bugs on patient care
The journey to selling the company
The $43 million acquisition process
Lightning round begins
Resources
Full show notes: https://saasclub.io/102
Join 5,000+ SaaS founders: https://saasclub.io/email
1 hr
January 06, 2016One Person SaaS Business to $10M ARR Without VC
Aaron Fulkerson built what started as a one person SaaS business into a company doing over $10 million a year - with clients like PayPal, Docker, and Whirlpool. But the road to 8 figures nearly killed the company first. In 2009, MindTouch was burning cash, churn looked terrible, and the product competed against SharePoint and hundreds of funded vendors.
Aaron and his co-founder Steve left Microsoft to start MindTouch as an open source project in 2005. Within two years, the project ranked in the top 5 on Sourceforge with over 2,000 downloads a day. They commercialized with support subscriptions and grew to $2.3 million in cash receipts by 2009 - all as a bootstrapped SaaS with zero outside funding.
Aaron cut 40% of headcount, pivoted from on-premise to cloud, and used $6.2 million in legacy revenue to fund the transition. The new self-funded SaaS grew from zero to over $10M ARR in three years, outperforming top Bessemer benchmarks by 1-2 standard deviations. This solo founder SaaS journey proves that grit and focus can replace venture capital.
🔑 Key Lessons
🎯 A one person SaaS business needs a defensible niche: MindTouch nearly died competing in general-purpose collaboration against hundreds of funded vendors. Survival came from narrowing to one use case - customer self-service content.
📉 Revenue growth can mask a dying business: MindTouch doubled revenue to $2.3 million but was burning cash with terrible churn and no defensible moat - top-line growth alone does not signal health.
💰 Legacy revenue can fund a SaaS pivot: Aaron used $6.2 million from the on-premise business over three years to finance the cloud rebuild plus a services team to cover headcount.
🧠 Culture principles survive failure better than strategies: Aaron and Steve set three rules - build products customers recommend, hire smart people, reject toxic hires - and credit those principles as why MindTouch survived.
🚀 Open source creates distribution for a one person SaaS business, not revenue: MindTouch hit millions of installs but distribution alone did not produce a defensible revenue model. Commercial success required a focused cloud product.
Chapters
Introduction
Aaron's motivation and what drives him
What MindTouch does and how it works
How Docker and Zenefits use MindTouch
MindTouch powering help centers at scale
Expanding from software to manufacturers
Life at Microsoft and meeting co-founder Steve
Dealing with imposter syndrome as a founder
How the MindTouch idea was born
Leaving Microsoft and starting the open source project
The 2,000 downloads in one day breakthrough
Why they chose open source and the open core model
First paying customers and early revenue
Funding the early years with friends and family
Why 2009-2011 were the hardest years
The 2008 financial crisis killed fundraising options
Pivoting from on-premise to cloud SaaS
The moment Aaron wanted to give up
Using legacy revenue to fund the transition
When things finally turned around
Three principles that saved the company
Lightning round begins
Resources
Full show notes: https://saasclub.io/101
Join 5,000+ SaaS founders: https://saasclub.io/email
50 min
November 04, 2015SaaS Growth: 10 Lessons from 99 Founder Interviews
After interviewing 99 SaaS founders, Omer Khan pulled the 10 pieces of business advice that stuck with him most - advice about SaaS growth, mindset, and the counterintuitive decisions that separate founders who succeed from those who stall. This is the 100th episode, and instead of bringing on another guest, Omer breaks down lessons from Dan Norris (WP Curve), Wade Foster (Zapier), Rob Walling (Drip), Peter Coppinger (Teamwork), Steli Efti (Close.io), and five other founders. Each piece of advice comes with the story behind it and how to apply it.
For the 100th episode of The SaaS Podcast, Omer Khan skips the guest interview and goes solo. Instead of bringing on another founder, he went through all 99 previous episodes and pulled out the 10 best pieces of SaaS growth advice - the ones that go beyond generic "work hard" and "be persistent" to something more specific and actionable. Peter Coppinger bootstrapped Teamwork to $14 million by thinking bigger than the Irish market.
Key Lessons
🚀 SaaS growth starts when you launch, not when you plan: Dan Norris failed for years doing validation before launching. WP Curve launched.

🎯 Do things that don't scale to accelerate early SaaS growth: Tom Leung manually matched job seekers with employers using a basic HTML form.

🧠 Don't let others set the agenda for your SaaS growth journey: Rob Walling built Drip without VC funding, Silicon Valley relocation, or 80-hour.

💰 Focus on value creation, not money, to drive SaaS growth: Trevor Owens warns that making every decision based on money leads to missed.

📉 Pivoting is not failing - it's essential SaaS growth iteration: Tom Leung's team pivoted 8 times in 2 years before achieving product-market fit.

⚡ Think bigger to unlock SaaS growth beyond your local market: Peter Coppinger bootstrapped Teamwork to $14M by refusing to think small. His.
Chapters
Introduction - reflecting on 100 episodes

Advice 1: Dan Norris - you don't learn until you launch

Advice 2: Trevor Owens - don't do it just for the money

Advice 3: Paul Graham - do things that don't scale

Advice 4: Rob Walling - don't let others set your agenda

Advice 5: Wade Foster - make today better than yesterday

Advice 6: Peter Coppinger - think big, then think bigger

Advice 7: Andrew Wilkinson - screw it, just do it

Advice 8: Tom Leung - pivot without guilt

Advice 9: Steli Efti - all advice is overgeneralization

Advice 10: Omer Khan - trust your gut

Closing reflections on the journey to episode 100
Resources
Full show notes: https://saasclub.io/100
Join 5,000+ SaaS founders: https://saasclub.io/email
30 min
October 14, 2015B2B Community Building: 5 Steps to Free Press for SaaS Startups
Most SaaS founders think PR requires paying an agency $10,000 a month. Conrad Egusa built Publicize to offer the same service starting at $399. But in this episode, he gives away the entire B2B community building and startup PR playbook for free.
Conrad is a former VentureBeat writer and global mentor at 500 Startups. He breaks down his 5-step process for getting press coverage, including why you should never combine announcements, how exclusives stand out in a journalist's inbox of 1,000 daily emails, and the follow-up tactic that turned a 1-out-of-15 response rate into near-universal coverage.
His coworking space in Medellin got covered by TechCrunch, BBC, and the Financial Times - not because coworking is interesting, but because he pitched B2B community building as "turning this city into the Silicon Valley of Latin America." SaaS content marketing through startup PR works when you frame the vision bigger than the product.
🔑 Key Lessons
📣 B2B community building through PR starts with a specific announcement: Founders who said "cover my company" got ignored. Founders who said "we launch next Wednesday" got press coverage.

🎯 Lead with social proof when pitching for press coverage: Half of what makes a story interesting comes from the founding team, not the product.

🚀 Make the mission bigger than the product for B2B community building: Conrad pitched "turning Medellin into the Silicon Valley of Latin America" instead of a coworking space.

💰 Never combine announcements in startup PR campaigns: Separating a launch and funding round into two campaigns doubles coverage opportunities.

⚡ Use exclusives instead of embargoes for early-stage B2B community building: Journalists won't commit to restrictions for unknown startups. One exclusive creates urgency.

🔄 Always send one follow-up email to maximize SaaS content marketing PR response: Conrad went from 1-out-of-15 responses to near-universal coverage with a single follow-up.
Chapters
Introduction - why PR matters for B2B community building

Step 1 - come up with a specific announcement

Step 2 - identify and lead with social proof

Step 3 - make the mission bigger than the product

Example - coworking space on TechCrunch, BBC, Financial Times

Step 4 - exclusive vs embargo approach

How to find the right journalists at publications

Step 5 - repeat the cycle every 8-10 weeks

Why startup PR compounds over time through SEO backlinks

Never combine announcements - double your press coverage

Lightning round begins

Passion - trying something new every six months
Resources
Full show notes: https://saasclub.io/99
Join 5,000+ SaaS founders: https://saasclub.io/email
41 min
October 07, 2015SaaS Product Validation: 8 Failed Pivots Then PMF in 1 Week
Tom Leung spent two years and $1.5 million building a startup that never found product-market fit. Then his team pivoted eight times in six months, and on the ninth try, a one-page HTML form proved they had SaaS product validation figured out - in one week.
Anthology (formerly Poachable) lets employed tech professionals explore career opportunities anonymously. Companies like Amazon, Microsoft, and Netflix recruit through the platform. Tom shares why the first startup failed and the painful lesson about solving "migraine" problems versus "mild annoyance" problems.
The contrast in startup validation was stark. At Yabli, nobody would ask a free question. With Poachable, people gave up sensitive salary data on a form with no SSL certificate. A GeekWire article on day two brought a flood of signups. Finding product-market fit required both a huge problem and a dramatically better solution for SaaS product validation to succeed.
🔑 Key Lessons
🎯 SaaS product validation requires a "migraine" problem: Users gave up sensitive salary data on an unsecured form because the problem mattered that much.

📉 Adding features won't save a bad idea during product-market fit testing: If you are solving the right problem, even a rough product should show strong traction without 50 iterations.

⚡ Set a one-month kill threshold for SaaS product validation experiments: Tom compressed 8 experiments into 6 months instead of spending years on each one.

🧠 Don't confuse tenacity with blind faith in your idea: Tom was persistent about Yabli for 2 years because admitting failure felt like admitting he wasn't smart.

🚀 Validate with real currency, not just email signups: People filling out sensitive fields proved genuine startup validation. 10,000 worthless emails are worse than 1,000 paying customers.

🔄 Your solution must be orders of magnitude better, not incrementally better: Finding product-market fit requires both a huge problem and a dramatically better solution.
Chapters
Introduction

What Anthology does and the problem it solves

The origin story - starting Yabli in 2012

Why Yabli never achieved SaaS product validation

The series of rapid pivots - 8 experiments

Building the Poachable landing page in a few hours

GeekWire coverage and the first week explosion

Asking for sensitive information as real validation

Tenacity versus blind faith - knowing when to pivot

The danger of being good at executing bad ideas

Lightning round begins

Passion - raising two sons
Resources
Full show notes: https://saasclub.io/98
Join 5,000+ SaaS founders: https://saasclub.io/email
50 min
September 30, 2015Launching an AI Marketplace: From Excel to 14K Developers
Diego Oppenheimer spent five years building Microsoft Excel features used by a billion people. Then he discovered that even Microsoft's $7 billion research center couldn't get algorithms to the teams that needed them. So he set about launching a marketplace to fix that.
Algorithmia connects academics building powerful algorithms with app developers who can use them - and hit 14,000 developers on the two-sided platform far faster than expected. Diego shares the journey of launching a marketplace from scratch, plus the systematic fundraising approach that raised $2.5 million by pitching worst-fit investors first.
The real validation for this marketplace startup came from Microsoft. An algorithm Diego searched months for already existed inside Excel - nobody knew. He ranked 60 investors in a spreadsheet, flipped the list, and pitched bottom-up to polish his answers before reaching top targets for the algorithm marketplace.
🔑 Key Lessons
🎯 Validate demand before launching a marketplace by finding gaps in existing systems: If even Microsoft's $7 billion research center couldn't connect algorithms to product teams, the opportunity was real.

💰 Pitch worst-fit investors first when fundraising for launching a marketplace: Diego started from the bottom of his ranked list. By the time he reached top targets, he had polished answers to every hard question.

🛠️ Do things that don't scale to learn what customers need: First customers were essentially discounted consulting engagements that provided direct access to feedback.

⚡ Compress decision-making speed when leaving corporate for a marketplace startup: At Microsoft, decisions took months. At Algorithmia, you decide in days, be wrong, and never repeat the mistake.

🚀 Build the platform before scaling when launching a marketplace: Twelve months of stability work paid off when 14,000 developers joined months ahead of the multi-year target.

📉 Kill ideas quickly when they don't solve a business case: The first iteration was an algorithm competition two-sided platform. Being willing to kill it fast freed the team to build what worked.
Chapters
Introduction

Diego's background at Microsoft building Excel

What Algorithmia does and the problem it solves

How the algorithm marketplace works for both sides

The origin story - backpacking trip to idea

Moonlighting at Microsoft while launching a marketplace

Building the MVP and getting first customers

Systematic fundraising - ranking 60 investors

Growth to 14,000 developers and university partnerships

Lightning round begins

Passion for STEM education for girls
Resources
Full show notes: https://saasclub.io/97
Join 5,000+ SaaS founders: https://saasclub.io/email
43 min
September 24, 2015Building a Self-Funded SaaS: Profitable in 2 Months on $50
George Palmer spent less than $50 to launch SendOwl, a self-funded SaaS for selling digital products. Two months later, it was profitable. He found first customers by searching Twitter every morning for people complaining about competitors.
George has experience building multiple businesses, from freelance Rails work to digital product platforms. In this episode, he shares how he validated SendOwl with a $100 AdWords test before writing code, why he turned down VC funding to keep his bootstrapped startup lean, and how a game studio's $18 million launch nearly crashed his servers - then became his biggest growth engine.
When Introversion Software chose SendOwl for the Prison Architect launch, the near-downtime crisis turned into word-of-mouth marketing. George's approach to building multiple businesses centers on marginal gains - staying lean, staying profitable, and turning every side project to business insight into a competitive advantage.
🔑 Key Lessons
💰 Validate your self-funded SaaS idea before building: George spent $100 on AdWords with a fake sign-up page. A 1.5% click-through rate gave him confidence to invest three months of development.

🎯 Find first customers where competitors fail: George searched Twitter daily for complaints about competing products, converting his first two paying customers within a month.

🚀 Turn a crisis into a growth engine when building multiple businesses: Prison Architect's launch nearly crashed SendOwl's server. The studio's founder became his biggest advocate at indie game conferences.

🧠 Stay bootstrapped to build on your terms: George turned down VC offers. Staying self-funded meant steady profitability with four employees and full control over his bootstrapped startup.

📉 Watch for the feature rat race in competitive markets: E-commerce customers will not use a product missing the one feature they need, regardless of design quality.

⚡ Structure your day around energy, not hours: George codes in the early morning, takes a 2.5-hour midday gym break, then handles support and admin.
Chapters
Introduction

George's background and how SendOwl started

Finding the first customers through Twitter

Total startup costs - under $50

Prison Architect launch and $18M in sales

Turning a server crash into a growth opportunity

Why George turned down VC funding for building multiple businesses

A typical day at SendOwl

Lightning round begins

Passion for fitness and marginal gains

Where to find George and SendOwl
Resources
Full show notes: https://saasclub.io/96
Join 5,000+ SaaS founders: https://saasclub.io/email
43 min
September 16, 2015SaaS Growth: 3 Hacks That Tripled Cold Email Response
Vincent Cassar sent cold emails to people who had never heard of his product and got a 40% response rate. His secret SaaS growth tactic was embarrassingly simple: follow up three to four times instead of once.
In this episode, Vincent walks through three specific SaaS growth hacks from his Growth Hacking Experiment, including how Quora became his best-converting lead generation source at 35% signup rate, why his cold email follow-up generates 4x the responses of a single email, and how pre-launch outreach created paying customers on day one.
Vincent published the Growth Hacking Experiment as transparent documentation of every startup growth tactic he tried with Keeping - including failures. The resource attracted the exact audience who also needed a helpdesk product: small businesses interested in SaaS growth.
🔑 Key Lessons
🚀 Follow up 3-4 times to triple SaaS growth from cold email: Vincent increased response rates from 10-15% to 40% by sending short follow-ups one to two days apart. Non-response usually means busy, not uninterested.

🎯 Place URLs near the top of Quora answers for SaaS growth: Five-to-six line answers with URLs placed high converted 35% of Quora visitors into free trial signups.

📉 Automated Twitter outreach destroys credibility faster than it builds it: Vincent's bot angered users and created infinite reply loops. The traffic was not worth the reputation damage.

🛠️ Add product screenshots below Quora answers to drive more lead generation clicks: Visual proof of the product gives readers a reason to click through.

🤝 Pre-launch cold outreach builds a customer pool before day one: Cold-emailing to validate the pain point created rapport with future customers who converted on launch day.

🧠 Growth hacking is marketing without media buying: The fundamentals - cold outreach, content marketing, and Quora - are proven startup growth tactics.

💰 Document your SaaS growth experiments publicly to attract ideal customers: Transparent documentation of results built credibility and drove qualified traffic.
Chapters
Introduction

How the idea for Keeping was born from personal frustration

The Growth Hacking Experiment - why share SaaS growth tactics publicly

Hack 1 - Cold email follow-up that reaches 40% response rate

Following up 20-30 times - lessons from Steli Efti

Hack 2 - Quora marketing with 35% conversion rate

Always include a link and image in Quora answers

Hack 3 - Pre-launch customer feedback for validation

Failed hack - automating Twitter replies with a bot

Lightning round

Where to find Vincent Cassar and Keeping
Resources
Full show notes: https://saasclub.io/95
Join 5,000+ SaaS founders: https://saasclub.io/email
55 min

About The SaaS Podcast: How B2B SaaS & AI Founders Get Customers

From the publisher's feed

Building software got easier. Getting customers didn't. Every week, a founder building B2B SaaS or an AI product tells you how they got their first customers, and how they kept them: what worked, what didn't, and what they'd do differently.