The SaaS Podcast - Building SaaS in the AI Era

Seven years selling a nice-to-have. Then 1,000 customers in year one. Adam Markowitz spent nearly a decade grinding in edtech before finding product-market fit at Drata. In this episode, founders will learn how to tell the difference between a vitamin and a painkiller - and why that distinction changes everything.

Adam shares how experiencing a compliance pain at his first startup became the foundation for Drata, why he refused to sell until his team used their own product to get SOC 2 compliant, and how a "give before you take" approach to AWS made Drata a top 5 ISV on Marketplace in under two years.

Drata has over 8,000 customers across 60 countries, more than 600 employees, and crossed $100 million in ARR before its fourth birthday. The company has raised over $300 million.

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🔑 Key Lessons

🎯 Product-market fit shows in buyer urgency, not just signups: Drata signed 100 customers in 6 weeks and 1,000 in year one - a stark contrast to Adam's edtech company where the first 5 university customers took years to close.

🛠️ Dogfood your product before selling it: Drata refused to accept customers until they used their own tool to get SOC 2 compliant, giving them instant credibility and proving the product worked under real conditions.

🔍 Validate by talking to every stakeholder, not just buyers: Adam spoke with dozens of companies and auditors before writing code, discovering identical pain patterns that made the initial product scope obvious.

🤝 Give before you take with strategic partners: Drata brought thousands of first-time customers to AWS Marketplace before asking for anything in return, becoming a top 5 global ISV in under two years.

📉 Selling a vitamin versus a painkiller changes everything: Seven years in edtech taught Adam what product-market fit feels like when you don't have it. At Drata, customers lined up because compliance wasn't optional.

🚀 Reassemble a proven team to compress execution time: Adam brought back the same co-founders, engineers, and go-to-market team from Portfolium. The muscle memory from working together for 7 years accelerated every phase of Drata's launch.

🏢 Keep partners independent to build a distribution moat: Drata's Auditor Alliance kept audit firms independent rather than competing with them. Two-thirds of Drata's pipeline is now sourced or influenced through partner channels.

Chapters

Introduction

What Drata does and the trust problem it solves

Revenue, customers, and team size

From astronaut dreams to NASA's Space Shuttle program

Building Portfolium after NASA retired the shuttle

Teaching himself to code and finding a CTO

Selling Portfolium for $43 million

The long road to product-market fit in edtech

The university sales cycle that changed everything

How the Portfolium pain led to founding Drata

Validating the problem before writing code

Getting the band back together

Using Drata to get their own SOC 2 before selling

Signing 100 customers in six weeks

How Drata differentiated in a crowded market

What broke at 1,000 customers

Building the Auditor Alliance partner program

The AWS Marketplace strategy and give-before-you-take

Why aggressive sales culture was intentional

AI tailwinds for compliance and trust

Lightning round

Closing thoughts

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Resources

Full show notes: https://saasclub.io/471

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$2M to $9M ARR in one year. Then it nearly fell apart. Gilles Bertaux expanded Livestorm into meetings and sales demos after COVID, turning it into a smaller Zoom with no clear differentiator. In this episode, founders will learn how he rebuilt product-market fit by narrowing to a niche most would run from.

Gilles shares why 85% of customers on monthly plans was a ticking time bomb, how a failed Series C forced the right strategic shift, and why targeting marketers instead of IT buyers let Livestorm avoid competing with Zoom on budget.

Livestorm generates nearly $20 million in ARR with 3,500 customers and has raised $35 million. Gilles co-founded the company in 2016 as a university project and has led it through explosive COVID growth, a near-collapse in positioning, and a rebuild to product-market fit with enterprise buyers.

This episode is brought to you by:

🌎 ThreatLocker → Book a demo

💖 Gearheart → Book a free consult and get the first 20 hours free

🔑 Key Lessons

🎯 Product-market fit can be lost by expanding too broadly: Livestorm added meetings and sales demos after COVID, turning into a smaller Zoom with no clear differentiator. The longer the sales conversation, the lower the conversion rate.

📉 Explosive growth can mask a fragile customer base: Going from $2M to $9M ARR in one year felt like traction, but 85% of customers were on monthly self-serve plans. One button click and that revenue disappears overnight.

🏢 Narrow positioning wins against giants: Livestorm stopped competing feature-for-feature with Zoom and differentiated on three dimensions - European company for security-conscious buyers, marketers only to avoid IT budgets, and specific industries like banking and pharma.

🔄 Selling to enterprise requires rebuilding the sales team, not retraining it: Reps who closed inbound leads from a CRM could not cold-call 10,000-person companies. Gilles had to replace almost the entire original sales team with people experienced in enterprise outbound.

💰 A failed fundraise can force the right strategic shift: When Series C investors said no in 2022, Livestorm had to become profitable. That constraint pushed them toward enterprise customers on annual contracts who pay more and stick longer.

🛠️ Target the buyer with a separate budget: By positioning Livestorm as a marketing tool instead of an IT tool, Gilles avoided budget wars with Zoom and Teams. Marketers control their own spend and do not need IT approval to buy.

Chapters

Introduction

What Livestorm does and who it serves

Revenue, customers, and funding

Building Livestorm as a university project

The disastrous first webinar launch

Why a product launch is a timeline, not a day

Finding the first 10 customers through inbound

SEO, Quora, and co-marketing as early growth engines

Competing with GoToWebinar and Zoom

How product-market fit shifted after COVID

Going from $2M to $9M ARR in one year

Support tickets from 200 to 20,000 and servers crashing

Post-COVID churn and the virtual event collapse

Why webinars survived but virtual events died

Losing product-market fit by becoming a smaller Zoom

Rebuilding positioning around Europe, marketers, and industries

Why video is a commodity and experience is the differentiator

How Livestorm processes 4,000+ feedback items per quarter

The painful shift from PLG to enterprise sales

Rebuilding the sales team for outbound

From tech nerd to startup CEO

Lightning round

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Scale from 6-figures to $1M ARR Faster: https://saasclub.io/mastermind

Get 1:1 async coaching from Omer: https://saasclub.io/accelerate

Resources

Full show notes: https://saasclub.io/470

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Adam Fard bootstrapped UX Pilot from a UX agency side project to $5 million ARR in under two years—growing from $3M to $5.3M in just five months—without VC funding, with 15,000 paying subscribers and a 30-person team.

In this episode, early-stage bootstrapped SaaS founders will learn how Adam discovered a wireframing opportunity by testing competitors and realizing they were all faking AI generation with templates. You'll hear why he spent 6-7 months solving the genuinely hard technical problem of AI wireframe generation, and how focusing exclusively on design (not no-code, not backend) became UX Pilot's biggest competitive advantage.

Adam also shares his biggest bootstrapped SaaS mistake: hiring too slowly. At $30K MRR, he questioned whether revenue might disappear and hired 1-2 people at a time, waiting months between hires. Looking back, he should have hired 5 people at once to gain velocity faster instead of prolonging the bootstrapped SaaS hiring process for months.

This episode is brought to you by:

🌎 ThreatLocker → Book a demo

💖 Gearheart → Book a free consult and get the first 20 hours free

🔑 Key Lessons

🎯 Test Competitor Claims Before Building Your Bootstrapped SaaS: Adam discovered other wireframing tools were faking AI generation by swapping templates, revealing a genuine technical opportunity.

💰 Bootstrap with Existing Revenue Streams: Adam used his UX agency income to fund UX Pilot development, removing pressure to raise VC funding or hit arbitrary bootstrapped SaaS revenue milestones.

🚀 Focus Beats Feature Bloat in Bootstrapped SaaS: While competitors built no-code tools that did everything, Adam focused exclusively on AI wireframe generation—no backend, no drag-and-drop, just design.

📈 SEO Still Works for Bootstrapped SaaS in 2024: Despite advice that "SEO is dead," Adam got significant traffic from high-intent keywords around "design, UX and AI generation" by being first to target them.

🧠 Hire Faster Than Feels Safe When Bootstrapping: Adam's biggest bootstrapped SaaS regret was hiring 1-2 people at $30K MRR instead of 5 at once—slow hiring cost months of velocity.

🛠️ Talk About Your Bootstrapped SaaS Product, Not Just Education: Adam got more newsletter engagement sharing UX Pilot updates than sending generic UX education—people want to know what you're building.

Chapters

Running a UX agency when ChatGPT launched

The user question that sparked the bootstrapped SaaS product idea

Testing competitors and discovering they were faking AI

Why creating wireframes with AI was technically hard

Exploring fine-tuning LLMs and component-based approaches

Building a 600K subscriber newsletter from product signups

Getting to the first million in ARR with LinkedIn, newsletter, and SEO

The bootstrapped SaaS mistake of hiring too slowly

The inflection point from $3M to $5.3M ARR in 5 months

Focusing on enterprise teams vs trying to target everyone

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SaaS Club Programs

Join the SaaS Club founder community: https://saasclub.co/plus

Build your $10K MRR SaaS: https://saasclub.io/launch

Scale from 6-figures to $1M ARR Faster: https://saasclub.io/mastermind

Get 1:1 async coaching from Omer: ⁠https://saasclub.io/accelerate

Resources

Full show notes: https://saasclub.io/469

Subscribe to the podcast: https://saasclub.io/subscribe

Two years. Almost no revenue. Tito Goldstein and his co-founder Arjun raised $3 million to build a scheduling tool for hourly workers. But when they took it to market, customers kept telling them the same thing: we need to stand out, not use cookie-cutter software. So they made a call that most founders would never risk - throw it all out and start over.

The rebuild took a year. But when they launched the new version built on composable Legos instead of fixed features, it outsold the previous two years in the first month. Then it 3x'd, and 3x'd again. That's when Tito knew they'd finally found product-market fit.

TeamBridge is now doing multiple seven figures with over 200 enterprise customers, including the San Francisco 49ers' Levi's Stadium and medical staffing agencies scaling to multimillion-dollar businesses with almost no admin staff.

This episode is brought to you by:

🌎 ThreatLocker → Book a demo

💖 Gearheart → Book a free consult and get the first 20 hours free

🔑 Key Lessons

🎯 Listen to what customers don't say about product-market fit: Buyers kept asking for features, but the real pain was "I need to stand out." Reading between the lines unlocked their product-market fit breakthrough.

📉 Throw out sunk cost when finding product-market fit: Two years of work became irrelevant when they realized connective tissue (automations, workflows) mattered more than scheduling.

🛠️ Composability wins in competitive markets: Off-the-shelf tools make you a commodity. Customizable workflows make you a differentiator in the race for product-market fit.

💰 Stay lean until product-market fit: TeamBridge kept a team of 5-6 with multiple years of runway, giving them freedom to pivot without investor pressure.

🚀 First products validate problems, not solutions: The scheduling tool failed but uncovered the real pain. Use early products to learn, not scale, on the path to product-market fit.

Chapters

Introduction and favorite quotes

What TeamBridge does and who it serves

Why composability matters for workforce software

Size of the business: revenue, customers, team

Origin story: interviewing Uber drivers

Going door-to-door to understand hourly worker pain

Raising $3M seed with just a prototype

Why it took 2 years to find product-market fit

The pivot: from scheduling to composable Legos

First significant sale during COVID

Biggest objections: explaining composability

Finding the right messaging and storytelling

Downsides of casting too wide a net

Moving upmarket to enterprise customers

How COVID forced TeamBridge to mature go-to-market

Cold email lessons: honesty and relationship building

Discovery-first selling: hold the pitch until you know the pain

Learning the nuances of each vertical

Lightning round: grit, curiosity, and fitness

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SaaS Club Programs

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Build your $10K MRR SaaS: https://saasclub.io/launch

Scale from 6-figures to $1M ARR Faster: https://saasclub.io/mastermind

Get 1:1 async coaching from Omer: https://saasclub.io/accelerate

Resources

Full show notes: https://saasclub.io/468

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He lived in his first customer's basement for a year. Nate Baker found Qualia's first customer by wearing a Stanford sweatshirt to a conference. That customer, Barry Feingold, didn't just sign up—he taught them the industry, made intros to competitors, and let the team live in his basement. In this episode, founders will learn how to find their first customers through network-based selling and multi-year upfront contracts.

Nate shares the brutal early days: building for months without talking to customers, getting their first customer's software shut off overnight, and plateauing at $45K ARR because they didn't respect sales as a skill. Their VP of Sales told them: "I've never seen such a gap between great product and incompetent sales execution." Within 12 months, they went from $45K to $3.5M ARR.

Today, Qualia generates over $100 million in ARR with 600 employees and has raised more than $200 million to transform the home buying process.

This episode is brought to you by:

💖 Gearheart → Book a free consult and get the first 20 hours free

🔑 Key Lessons

🎯 First Customers Must Come From Your Network: Nate says your first 10 customers must come from in-network sales—cold outreach rarely closes when you're asking someone to trust an unproven system of record.

💰 Multi-Year Upfront Contracts Bring Cash Forward: Qualia offered 5-year contracts paid upfront at 80% discounts, aligning incentives and generating meaningful early revenue.

🏠 Embed Yourself With Your First Customer: The first 25 Qualia employees rotated through Barry's basement learning the industry—"you have to be so in it" to build great software.

🗺️ Geographic Focus Beats National Expansion Early: Qualia stayed focused on Massachusetts for the first year, building deep relationships before expanding state by state.

⚡ Crisis Creates Your Most Productive Moments: When Barry's vendor shut him off overnight, Qualia had to deliver—it became their most productive month ever.

🔧 Engineers Must Respect Sales as a Skill: At $45K ARR, the founders thought product would speak for itself. Hiring a VP of Sales unlocked $3.5M ARR in 12 months.

Chapters

Introduction and what Qualia does

How Nate picked the title software market at 21 with no experience

The academic approach to market selection (and why it was a mistake)

The real problem: coordination across multiple stakeholders

Finding first customer Barry Feingold at a conference

Living in Barry's basement for a year

When Barry's vendor shut him off overnight

How long it took to ship the first version

Why narrow geographic focus beats national expansion early

Early customer conversations and what they actually needed

How to get customers to pay before you've built the product

The multi-year upfront contract strategy

Network-based selling vs cold outreach for first customers

The wake-up call: "Great product, incompetent sales execution"

Moving upmarket and the "you don't understand Texas" objection

Strategy for geographic expansion state by state

When Nate realized they had real traction

How the opportunity looks today with AI

Lightning round

💌 Get weekly 5-minute SaaS insights: https://saasclub.io/email

SaaS Club Programs

Join the SaaS Club founder community: https://saasclub.co/plus

Build your $10K MRR SaaS: https://saasclub.io/launch

Scale from 6-figures to $1M ARR Faster: https://saasclub.io/mastermind

Get 1:1 async coaching from Omer: https://saasclub.io/accelerate

Resources

Full show notes: https://saasclub.io/467

Subscribe to the podcast: https://saasclub.io/subscribe