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

October 15, 2014Starting a SaaS: How Canva Hit 800K Users in Year One
Melanie Perkins spent seven years turning a university side project into one of the fastest-growing design platforms ever built. Starting a SaaS from scratch, she bootstrapped a yearbook tool called Fusion Books, then used those lessons to launch Canva - which hit 800,000 users and 5.5 million designs in its first year.
Melanie reveals how starting a SaaS with blogger outreach created a viral loop, why she spent a full year finding the right technical co-founder, and how Guy Kawasaki joined after a single tweet. This is a SaaS startup guide for anyone launching a SaaS business from zero.
🔑 Key Lessons
🚀 Starting a SaaS begins with a painful problem: Canva grew to 800,000 users because design tools were genuinely difficult. Melanie built a product so simple that users naturally told others about it.

🎯 Target users who amplify your growth: Canva deliberately targeted bloggers first because they needed to design daily and had large audiences. Each new blogger became an unpaid evangelist.

📉 Bootstrap before you fundraise: Melanie spent five years bootstrapping Fusion Books before raising $6 million for Canva. That experience in starting a SaaS from scratch taught her how to start a SaaS the right way.

🛠️ Start niche, then go wide: Canva began as Fusion Books serving school yearbooks in Australia. Melanie proved the technology in a narrow, profitable market first, then expanded to mass consumer design.

💰 Lower price barriers to unlock new markets: Canva introduced a patented $1 stock image license when competitors charged $10 to $50 per image. This made professional imagery accessible to everyday creators.

🧠 Wait for the right team instead of hiring fast: Melanie spent a full year finding technical co-founder Cameron Adams. That patience built a team of 40 in Canva's first year.
Chapters
Introduction

Melanie's background and the Canva story

Favorite success quotes from Seth Godin and Steve Jobs

Life before Canva and early entrepreneurship

Starting Fusion Books at university

How Fusion Books became the blueprint for Canva

Ownership and growth of Fusion Books

The decision to build Canva and the San Francisco journey

From Fusion Books to Canva's broader market

Targeting bloggers as the first users

Blogger outreach as the early growth engine

Lessons from trying hundreds of approaches

Why Canva raised VC funding after bootstrapping

Organic community growth and word-of-mouth

Scaling challenges from 10 to 40 people

Revenue model and the $1 stock image license

Building a contributor community of photographers

How Guy Kawasaki joined Canva

Future vision and upcoming product launches

Lightning round

Final thoughts on persistence and commitment
Resources
Full show notes: https://saasclub.io/12
Join 5,000+ SaaS founders: https://saasclub.io/email
24 min
October 13, 2014 011: How Gary Swart Built the World's Largest Online Workplace - with Gary Swart
Gary Swart is a Venture Partner at Polaris Partners, an 18-year old venture capital firm. Gary is also the former CEO of Odesk, the world’s largest online workplace with over 1 million clients and 5 million freelancers. He joined the company as its CEO in 2005 and has guided the company to industry leadership and through their recent merger with Elance.
36 min
October 12, 2014SaaS Marketplace Lessons From 15 People to $1B
oDesk was manually screening every freelancer before they could join the SaaS marketplace. With a backlog of 5,000 workers and only 40 getting through per day, CEO Gary Swart realized the company was blocking its own growth. He killed the high-touch model, lowered prices, and let the SaaS marketplace mechanisms take over.
The result: $1 billion in work through the platform, 10 million freelancers, and a merger with their biggest competitor Elance. Gary shares how he scaled this two-sided marketplace from 15 people to a dominant online marketplace - and the mistakes he made along the way.
🔑 Key Lessons
🎯 Focus your SaaS marketplace on one thing first: oDesk's earlier venture Intellibank tried to build document sharing, workflow, and version control all at once. Dropbox won by doing one thing well.

📉 High-touch models block SaaS marketplace growth: oDesk manually screened every freelancer, capping onboarding at 40 per day with 5,000 in the queue. Removing the bottleneck meant trusting marketplace business mechanisms over human gatekeepers.

🚀 Referrals beat paid acquisition in a SaaS marketplace: oDesk's best customers came from friends who not only brought new clients but helped onboard them and recommended specific freelancers, creating a self-reinforcing growth loop.

💰 Lowering prices can accelerate marketplace scale: oDesk dropped prices when shifting from high-touch to an open two-sided marketplace. The lower margins were offset by dramatically faster growth and higher volume.

🔄 Mergers beat endless competition: oDesk and Elance were heading to the same destination. Rather than fighting for market share, they merged to create a $1B combined platform with 10M+ freelancers.

🧠 Say no more than you say yes: Gary credits "shiny object syndrome" as his biggest early mistake. Chasing too many directions diluted focus and slowed growth during the critical early years.
Chapters
Introduction

Gary Swart's background and oDesk overview

Success quote on learning from failure

Leaving IBM as employee 131,000

Intellibank - "Dropbox gone wrong"

What Gary would do differently at Intellibank

How Gary joined oDesk as CEO

Starting with just 15 people

The early SaaS marketplace business strategy

Why the original model could not scale

Manual screening bottleneck - 40 workers per day

Quality vs scalability tradeoff

Biggest early mistake - shiny object syndrome

Advice for marketplace founders

Customer acquisition through referrals

Growing pains and balancing both sides

How the oDesk-Elance merger happened

Moving to Polaris Partners

Lightning round

Where to find Gary online
Resources
Full show notes: https://saasclub.io/11
Join 5,000+ SaaS founders: https://saasclub.io/email
35 min
October 08, 2014 010: How to Raise $11 Million by Making Project Management Social - with Andrew Filev
Andrew Filev is the founder and CEO of Wrike, a provider of social project management and collaboration software that helps co-located and distributed teams to get things done together in real time. Andrew founded the company in 2006 and to date has raised more than $11M in funding.

49 min
October 07, 2014Self-Serve SaaS: How Wrike Reached 6,000 Customers
No sales team. No personal network. Strangers found it, tried it, paid for it. Andrew Filev deliberately avoided friends-and-family sales and let Wrike's self-serve SaaS model prove demand. A freemium SaaS approach and SaaS content marketing grew the platform to 6,000 paying customers across 50 countries.
Andrew shares how he merged project management and collaboration into one product, why his biggest mistake was not talking to customers enough, and how a self-serve SaaS approach landed 40+ Fortune 1000 accounts without an enterprise sales team.
Wrike raised over $11 million in funding. The product scales from 5-user teams to organizations with 1,000+ users managing thousands of projects - a product-led growth flywheel that turns small team adoption into enterprise expansion.
🔑 Key Lessons
🛠️ Build self-serve SaaS by solving your own pain: Andrew built Wrike because emails and spreadsheets failed his own fast-growing team. Starting as your own first user creates authentic product DNA from day one.

🚀 Self-serve SaaS beats enterprise sales for early traction: Wrike grew to 6,000 paying customers by letting people find, try, and buy online. No sales team was involved in the early years.

📉 Not talking to customers is the costliest early mistake: Andrew admits his engineering background made him avoid deep customer conversations. He recommends talking to active users, regular users, and churned users separately.

🎯 Merge adjacent markets to create differentiation: Wrike combined work management and collaboration into one product. That category-defining move attracted customers no competitor could serve.

💰 Validate with strangers to prove genuine demand: Andrew deliberately avoided friends-and-family sales. His first customers were strangers who found Wrike online, proving the product could acquire users without personal networks.

🧠 Stay focused because overnight success takes years: Andrew's top advice is to resist premature pivoting. Building something people use daily requires sustained execution, not just a compelling idea.

🔄 Use content marketing as the scalable self-serve SaaS channel: Wrike tried trade shows, analyst outreach, and ads. Content marketing outperformed all of them because it compounds over time.
Chapters
Andrew's background and Wrike overview

The origin story behind Wrike

Merging work management and collaboration markets

Customer validation and talking to early users

Timeline from idea to first paying customers

Early customer growth and exponential compounding

Biggest mistake: not talking to customers enough

Three pillars of early self-serve SaaS growth

Most successful marketing strategy

Key business metrics and milestones

Building for diverse use cases and product-led growth scalability

Lightning round
Resources
Full show notes: https://saasclub.io/10
Join 5,000+ SaaS founders: https://saasclub.io/email
47 min
October 06, 2014 009: How to Build a SaaS Product in a Weekend and Raise $8 Million - with Sahil Lavingia
Sahil Lavingia is the founder and CEO of Gumroad, a startup which enables creatives (such as writers, designers and musicians) to sell their products directly to their audience. Sahil founded Gumroad in 2011 and to date has raised more $8 million in funding.
34 min
October 05, 2014SaaS Fundraising: How Sahil Lavingia Raised $8M for Gumroad
Built in a weekend. 50,000 visitors on Monday. Zero dollars spent on marketing. Sahil Lavingia built the first version of Gumroad over a single weekend and posted it on Hacker News. Product-led growth did the rest - every creator sale exposed Gumroad to buyers who were creators themselves.
Sahil shares how he went from Pinterest's 4-person team to SaaS fundraising $8M for his own creator economy platform, why he deliberately ignored customer acquisition in favor of building a product-led growth engine, and what he learned about leadership as a 22-year-old first-time CEO.
Gumroad's SaaS fundraising journey included a $1M seed round and $7M Series A while the team focused entirely on product. The SaaS go-to-market strategy was simple: make every transaction an acquisition channel.
🔑 Key Lessons
🛠️ Build a weekend MVP to validate product-led growth potential: Sahil built Gumroad in two days. The prototype was simple - upload a file, set a price - but it attracted 50,000 visitors and proved demand.

🚀 Let every transaction drive growth automatically: Gumroad grew without marketing because every sale exposed the platform to buyers. Many buyers were creators who could use Gumroad themselves, creating a self-reinforcing loop at zero cost.

💰 Let VCs come to you by building in public: Sahil raised a $1M seed round to buy time, then focused on building. VCs reached out after seeing Gumroad's progress, leading to a $7M Series A without aggressive SaaS fundraising.

🧠 Communicate the why, not just the what, as a first-time CEO: Sahil learned that leadership requires explaining reasoning behind decisions proactively. Self-awareness and giving feedback mattered more than technical ability.

📉 Accept that growth compounds slowly at first: Sahil expected a 30x better product to attract 30x more users immediately. He learned to keep building toward the vision rather than reacting to short-term behavior.

🔄 Abstract away complexity to deepen engagement: Gumroad evolved from raw file uploads to content-type experiences. Creators stopped thinking about zip files and started thinking about selling a book.
Chapters
Sahil's background and what Gumroad does

Growing up in Singapore and moving to the US

How Sahil joined Pinterest at four people

Why Sahil left Pinterest to start Gumroad

Discovering the problem of selling digital files

Building the first version of Gumroad in a weekend

Launching on Hacker News and reaching 50K visitors

Why Sahil focused on product instead of acquisition

How Gumroad's product-led growth loop works

Evolving from raw files to content-type abstractions

Challenges of being a first-time CEO at 22

SaaS fundraising: raising the $7M Series A round

Long-term vision for Gumroad as a creator platform

Lightning round
Resources
Full show notes: https://saasclub.io/9
Join 5,000+ SaaS founders: https://saasclub.io/email
32 min
October 01, 2014 008: How Balsamiq Bootstrapped Its Way to $6M per Year in Revenue - with Peldi Guilizzoni
Peldi Guilizzoni is the founder of Balsamiq Studios, which makes Balsamiq Mockups a tool for creating quick and intuitive user interface mockups. Peldi launched Balsamiq as a one-man software company in 2008 and within 18 months, Balsamiq reached $2 million in revenue. Balsamiq is on track this year to hit $6 million in revenue.
42 min
September 30, 2014Freemium SaaS: How Peldi Built Balsamiq to $6M Solo
Built alone in a kitchen. First sale before launch day. Peldi Guilizzoni coded Balsamiq Mockups from 8pm to midnight while working at Adobe. Four days after quitting, someone found the site through Google and bought his freemium SaaS product. Product-led growth took it from there - $2M in 18 months, $6M by year six.
Peldi reveals why Balsamiq's sketchy mockup style turned every shared image into word-of-mouth SaaS marketing, how giving bloggers two free licenses created a backlink snowball, and why he resisted beta users who demanded a desktop version that became 60% of revenue.
Balsamiq grew to over 200,000 customers with a small remote team, zero VC funding, and no formal sales team. A solo founder SaaS story built through pure product-led growth.
🔑 Key Lessons
🛠️ Product-led growth starts with built-in virality: Balsamiq's sketchy mockup style made every shared image a conversation starter, turning 200,000 users into unpaid marketers without any referral program.

🚀 Amplify freemium SaaS growth with blogger outreach for SEO: Peldi gave bloggers two free licenses each, generating hundreds of backlinks and reviews that snowballed organic search traffic into the primary acquisition channel.

🧠 Listen when customers reject your business model: Peldi planned Balsamiq as a Confluence-only enterprise plugin, but beta users demanded a desktop version. He resisted for weeks - desktop became 60% of revenue.

💰 Save a full year of runway before quitting your day job: Peldi sold Adobe stock options and stopped 401k contributions to build a cash cushion, giving himself 12 months of focused development.

📉 Hire before burnout forces your hand: Peldi handled 3,000 customers solo until a health scare from six straight weeks without a day off forced him to hire. Make the first hire earlier than comfortable.

🎯 Say no to tempting distractions: Balsamiq was approached about versions for chemistry, gardening, and other verticals. Peldi turned them all down to maintain focus on one freemium SaaS product for one audience.
Chapters
Introduction and Balsamiq overview

Life before Balsamiq at Adobe

Why Peldi decided to go solo with no co-founders

Building Balsamiq nights and weekends

First sale before launch day

Built-in product-led growth and freemium SaaS virality

Validation through personal use and beta testers

Finding an untapped market for wireframing

Biggest mistake: waiting too long to hire

Revenue milestones from $160K to $6M

Marketing evolution with AdWords and sponsorships

Building Balsamiq's remote culture

The golden puzzle philosophy

Lightning round
Resources
Full show notes: https://saasclub.io/8
Join 5,000+ SaaS founders: https://saasclub.io/email
41 min
September 29, 2014 007: How a SaaS Product Helped Its Customers Earn Over $261 Million - with Ruben Gamez
Ruben is the founder of BidSketch, a web app which helps freelancers, consultants and agencies to create professional looking proposals in minutes. Ruben launched Bidsketch as a one-person company in 2009. Since then, it’s grown to help over a 1000 paying customers earn over $261M in revenue.
43 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.