Adam Markowitz is the co-founder and CEO of Drata, a trust management platform that helps companies automate compliance, security assurance, and third-party risk management. He spent seven years building an edtech company that universities liked but never urgently needed. Then he stumbled into a problem so painful that 100 customers signed up in six weeks. The difference between his two companies wasn't the team, the market timing, or the fundraising. It was a single conversation with a university CIO that exposed a contradiction he couldn't unsee - and it became the foundation for a $100M ARR business. Today, Drata has over 8,000 customers across 60 countries, more than 600 employees, and has raised over $300 million. š KEY LESSONS šÆ The Vitamin vs. Painkiller Test: Drata signed 1,000 customers in year one. Adam's edtech company took years to close the first 5 universities - same founder, same team, completely different urgency from buyers. š ļø The Self-Imposed Sales Ban: Drata refused to accept paying customers until they used their own product to earn SOC 2 compliance. It delayed revenue but gave them instant credibility with every prospect. š The Google Doc That Proved the Problem: Adam and his co-founders talked to dozens of companies and auditors before writing code. The same exact words kept appearing - making the initial scope obvious. š¤ The Give-Before-You-Take Partnership: Drata brought thousands of first-time customers to AWS Marketplace before asking for anything. They became a top 5 global ISV in under two years. š The 7-Year Lesson: It took Adam 3 years at Portfolium just to discover that universities needed learning outcomes tools, not career portfolios. At Drata, he validated the problem in months. ā±ļø TIMESTAMPS 00:00 Introduction 00:28 What Drata does and the trust problem it solves 01:39 Revenue, customers, and team size 03:09 From astronaut dreams to NASA's Space Shuttle program 05:11 Building Portfolium after NASA retired the shuttle 07:03 Teaching himself to code and finding a CTO 08:26 Selling Portfolium for $43 million 09:43 The long road to product-market fit in edtech 12:15 The university sales cycle that changed everything 15:39 How the Portfolium pain led to founding Drata 19:44 Validating the problem before writing code 23:28 Getting the band back together 26:29 Using Drata to get their own SOC 2 before selling 28:20 Signing 100 customers in six weeks 29:08 How Drata differentiated in a crowded market 34:19 What broke at 1,000 customers 36:22 Building the Auditor Alliance partner program 39:09 The AWS Marketplace strategy and give-before-you-take 42:48 Why aggressive sales culture was intentional 46:53 AI tailwinds for compliance and trust 50:36 Lightning round 55:08 Closing thoughts š§° RESOURCES š Get weekly 5-minute SaaS insights: https://saasclub.io/email š” Join the SaaS Club founder community: https://saasclub.co/plus š Build your $10K MRR SaaS: https://saasclub.io/launch š Scale from 6-figures to $1M ARR Faster: https://saasclub.io/mastermind šÆ Get 1:1 async coaching from Omer: https://saasclub.io/accelerate š§ Full Show Notes: https://saasclub.io/471 š¤ Subscribe to the Podcast: https://saasclub.io/subscribe #SaaS #ProductMarketFit #Startup #FounderStory #B2BSaaS