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

November 02, 2014SaaS Go-to-Market: Tested 5 Ideas, Built the Winner
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 hustle - personally tweeting 20-30 prospects a day, answering questions on Quora, and giving free landing page advice to every new signup. That go-to-market strategy grew the business to $40K/month with 1,000 paying customers.
🔑 Key Lessons
🎯 Validate your SaaS go-to-market with data, not guesses: Josh built landing pages for five finalist ideas and measured email signups. The idea with 2x more captures won, removing guesswork from the launch strategy.

🤝 Personalize outreach to win first customers: Josh sent 20-30 personalized tweets daily, referencing prospects' bios and frustrations. Generic messages got ignored, but personal engagement converted strangers into customers.

🛠️ Give hands-on help to convert free users to paid: Josh personally reviewed landing pages and suggested copy improvements for the first 1,000 signups. That individual attention drove upgrades better than any automated funnel.

📉 Fix churn by expanding beyond one-time use cases: Launch customers quit in months because startups fail. Adding contests, referral tools, and CRM integrations attracted recurring campaign users.

🚀 Drive traffic before optimizing conversions: A customer with 30% conversion rate and 75 visitors quit thinking conversions were broken, when the real problem was too few visitors.

🧠 Build your SaaS go-to-market around where the audience gathers: Josh answered questions on Quora and engaged in GTM SaaS communities. Going to the audience accelerated early traction.
Chapters
Introduction

Josh's background and why he left corporate life

Success quote: "Do or do not, there is no try"

Who KickoffLabs serves and how viral referrals work

Customer success story: Chubbies Shorts tripled email lists

Where the idea for KickoffLabs came from

Validating ideas with landing pages

The other idea: Sift Social and why they killed it

Getting the first customers through personal outreach

Revenue growth: from $8K to paying themselves

Biggest mistake: optimizing conversions with low traffic

Growth trajectory and team building

Building a business with work-life balance

The retention challenge and how they solved it

Current customer count and revenue

Scaling personalization through live webinars

Lightning round

Wrap-up and where to find Josh
Resources
Full show notes: https://saasclub.io/17
Join 5,000+ SaaS founders: https://saasclub.io/email
51 min
October 30, 2014 016: How Paras Chopra Bootstrapped an $8 Million SaaS Business - with Paras Chopra
Paras Chopra is the founder & CEO of Wingify, which makes Visual Website Optimizer, a market leading A/B split testing tool. Paras launched and bootstrapped Visual Website Optimizer as a one-man software company in 2010 and within 2 years had over 1000 paying customers. Currently, Visual Website Optimizer is driving over $8M in annual revenue.
52 min
October 29, 2014Bootstrapped SaaS Growth: Guest Blogging to $8M ARR
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, running a closed beta with exclusive invite codes, and competing head-to-head against Google's free A/B testing tool. All growing without funding and from a room in India.
🔑 Key Lessons
🎯 Guest blogging drives bootstrapped SaaS growth when you educate, not promote: Paras wrote A/B testing articles for Smashing Magazine without mentioning VWO. The author bio drove signups, proving education beats pitching.

📉 Validate before building to avoid wasted effort: Paras spent seven months coding an all-in-one tool without talking to users. It failed. VWO took one month because he built only what customers asked for.

🚀 Closed betas amplify bootstrapped SaaS growth with exclusivity: Exclusive beta invites through each publication gave blogs an incentive to feature his articles and readers a reason to sign up immediately.

💰 Charge for your product even when competitors offer it free: Google offered free A/B testing, but VWO's no-code visual editor was 10x easier for marketers. A dramatically better experience justifies paid pricing.

🤝 Customer service powers bootstrap growth through referrals: Wingify handwrote cards to 900 customers in 35 countries and had every team member do support. Those personal touches doubled revenue year over year.

🧠 Failed startups teach you to stop building what nobody wants: Paras failed four or five times before his breakthrough came from asking about customer frustrations first instead of chasing his own ideas.
Chapters
Introduction

Paras Chopra's entrepreneurial background

Four failed startups before Wingify

The rock band portal that went nowhere

Motivation and challenging the best in the world

Where the idea for Visual Website Optimizer came from

Why the first Wingify prototype failed

Guest blogging on Smashing Magazine

Research and closed beta with exclusive invite codes

Building the product while working full-time

Competing against Google's free A/B testing tool

First month revenue of $4,000

Customer feedback and bootstrapped SaaS growth tactics

Handwritten cards to 900 customers in 35 countries

Biggest mistake - not growing the team fast enough

Scaling to 60 people and $8M ARR

Vision for India as a software product hub

Lightning round

Where to find VWO and Paras
Resources
Full show notes: https://saasclub.io/16
Join 5,000+ SaaS founders: https://saasclub.io/email
50 min
October 28, 2014 015: How a Failed Startup Helped Build an 8-Figure SaaS Business - with Adam Schoenfeld
Adam Schoenfeld is the co-founder & CEO of Simply Measured, a leading social media analytics and measurement platform used by brands such as Samsung, Microsoft, American Express and Pepsi to name a few. Adam founded Simply Measured in 2010 along with his co-founders Aviel Ginzburg and Damon Cortesi. The company now has over 150 employees and to date has raised $29 million in venture capital funding.
47 min
October 27, 2014SaaS Pricing Strategy That Went From $2.50 to 8 Figures
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, why his founding team started as "Untitled Startup" with no product idea, and the exact moment he realized agencies would pay 50x more than his original pricing model.
🔑 Key Lessons
💰 Start with a paid pricing strategy from day one: Adam's first startup failed because nobody would pay. At Simply Measured, charging $2.50 from the start proved marketers would pay for social analytics and validated the subscription pricing approach.

📈 Raise prices when customers ask for more features: When agencies needed multi-channel tracking, Adam introduced a $500/month tier - a 50x jump. Willing customers signaled the market could bear a higher pricing strategy.

🎯 Let paying customers drive your roadmap: Simply Measured focused on expanding value for paying customers rather than building features free users requested. Paying customers describe real problems worth solving.

🚀 Use a team-first approach when you lack a product idea: Adam and his co-founders started as "Untitled Startup" and ran experiments until one stuck. Complementary skills mattered more than a perfect idea.

📉 Hire salespeople before the bottleneck breaks growth: Adam closed all deals himself and waited too long to hire. Simply Measured ended up with more leads than one person could handle.

🏢 Move upmarket by pricing around customer complexity: Simply Measured scaled its pricing model with social profile count and audience size. Enterprise brands naturally landed at higher contract values.
Chapters
Introduction

Adam's background and personal interests

Success quotes from John Wooden

Cheddar Media: the startup that failed

When to pivot vs when to shut down

Simply Measured's target customers and differentiation

Founding as Untitled Startup with no product idea

Why a team-first approach works

How early agency customers shaped product direction

RowFeeder: the weekend hack that became the product

Early pricing strategy: from $2.50 to $500 a month

Customer acquisition and the first year of growth

Moving from $10/month to $500/month plans

Biggest mistake: hiring salespeople too late

Growing pains of transitioning the brand

Drawing on lessons from a failed startup

Discovering enterprise brands as the real market

Co-founder roles and building the executive team

8-figure revenue and scaling to 125 people

Lightning round
Resources
Full show notes: https://saasclub.io/15
Join 5,000+ SaaS founders: https://saasclub.io/email
45 min
October 23, 2014 014: How Wistia Turned Video Hosting Into a Profitable SaaS Business - with Chris Savage
Chris Savage is the co-founder and CEO of Wistia, an internet video hosting and analytics company that enables marketers to track and analyze web video viewers. Chris and his co-founder Brendan founded Wistia in 2006. In 2009 they were finalists in BusinessWeek’s 25 Most Promising US entrepreneurs under the age of 25.
42 min
October 22, 2014SaaS Content Strategy: 100K Customers, No Sales Team
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 strategy attracted buyers who were already searching for video solutions, why he waited four and a half years before adding credit card payments, and how content-led growth built a profitable 31-person company.
🔑 Key Lessons
🎯 SaaS content strategy beats cold calling when buyers are not ready: Chris's cold calls failed because prospects had no video content yet. Switching to B2B content strategy attracted people already searching for solutions, replacing Wistia's entire outbound sales function.

🛠️ Solve processes manually before building features: Wistia hand-made embed codes for individual customers and required phone calls to sign up. Savage only automated when persistent demand proved the feature was worth building.

💰 Small ad experiments validate your SaaS content strategy fast: Wistia spent just $40 on AdWords and landed Cirque du Soleil at $500/month. That single experiment proved content marketing SaaS generated better leads than months of cold calling.

📉 Flat organizations centralize power unintentionally: Having no formal structure meant every major decision flowed to the founders. Adding teams and leads gave more people real ownership.

🚀 Freemium removes friction and replaces your sales team: Wistia's free 10 GB tier let marketers try the product without talking to anyone. Combined with SaaS content strategy, this self-serve model grew to 100K+ customers with zero salespeople.

🔄 Customer requests reveal your real product direction: Wistia told customers to use YouTube for embeds. Customers refused and kept asking. That persistent demand led to the embed and analytics features that became Wistia's core business.
Chapters
Introduction

Chris Savage's background and Wistia overview

Success quote and entrepreneurial philosophy

Pain points Wistia solves for marketers

Wistia vs YouTube for business video

Origin story and the early idea for Wistia

Four years without video embedding

Bootstrapping in a 10-person house

Getting the first paying customer

Why Wistia had no website for years

Lessons from overbuilding the failed portfolio site

Considering Starbucks jobs for health insurance

What kept them going through a year of zero customers

The moment Wistia felt like a real business

From cold calling to SaaS content strategy

How $40 on AdWords landed Cirque du Soleil

Growing pains and the flat organization problem

Wistia's scale today and 100K customer milestone

Business model and freemium pricing

Lightning round
Resources
Full show notes: https://saasclub.io/14
Join 5,000+ SaaS founders: https://saasclub.io/email
40 min
October 19, 2014 013: How Wave Is Making Over a Million Small Business Owners Happier - with Kirk Simpson
Kirk Simpson is the co-founder and CEO of Wave, an integrated online solution designed for small businesses to manage their financial life. Wave has signed up well over 1,000,0000 users and currently serves customers in more than 200 countries around the world. And to date, Wave has raised over $25 million in VC funding.
38 min
October 18, 2014Freemium SaaS Playbook: From Free to 1M Users
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 painful lesson he learned after hiring 50 people in six months. If you are considering a freemium SaaS approach, this episode breaks down what actually works.
🔑 Key Lessons
🚀 A freemium SaaS model can unlock massive scale in low-LTV markets: Wave gave away its core accounting product because micro small businesses churn fast and have low lifetime value, making paid acquisition nearly impossible at the volume needed.

💰 Monetize freemium SaaS through transactions, not subscriptions: Wave generated revenue from payroll services, payment processing on invoices, and in-app ads - proving that free software sustains a business when paired with the right freemium to paid revenue layers.

⚡ Small bets on new platforms produce outsized growth: Kirk spent $5 and two hours listing Wave in the Google Chrome Store. An editor featured it, driving 210,000 installs and becoming one of Wave's biggest acquisition channels.

🎯 Build for your actual customer, not the loudest user segment: Most accounting software drifts toward accountants and bookkeepers. Kirk refused to build features that did not serve micro small business owners directly.

📉 Hiring faster than your management systems will force a painful reset: Wave added 50 people in six months, but communication and management processes broke down. Kirk had to downsize and called it one of his biggest regrets.

🧠 Free does not excuse a bad freemium SaaS product: Power users compare free products against paid alternatives just as rigorously. A free price tag does not lower the quality bar - it raises the volume of scrutiny.
Chapters
Introduction

Kirk's background and Wave overview

Why Kirk does not rely on quotes for motivation

Why Wave targets micro small businesses

Pain points of small business accounting

Building Wave's early alpha product

Bootstrapping before raising funding

Throwing out the alpha and rebuilding

Early customer feedback and the freemium SaaS decision

Positioning Wave against QuickBooks and incumbents

Acquiring the first 1,000 users

The $5 Google Chrome Store listing that changed everything

Growth from 1,000 to 1 million users

Growing pains: hiring 50 people in six months

Reaching the million user milestone

How Wave generates revenue from a free product

Why management discipline matters more than it sounds

Lightning round

Book recommendation: The Hard Thing About Hard Things

Where to find Wave and Kirk online
Resources
Full show notes: https://saasclub.io/13
Join 5,000+ SaaS founders: https://saasclub.io/email
36 min
October 16, 2014 012: How Canva is Making Graphic Design Amazingly Simple for Everyone - with Melanie Perkins
Melanie Perkins is the 27 year old co-founder and CEO of Canva, an online design platform which makes graphic design amazingly simple for everyone, by bringing together a drag-and-drop design tool with a library of more than a million stock photographs, graphic elements and fonts. Melanie founded Canva in 2012 and to date has raised over $6M in VC funding.
26 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.