Episode #98: Inside the $2 Trillion Employee Benefits Market Ryan Sachtjen is the Co-founder and CEO of Threeflow, building software for employee benefits brokers and insurance carriers. We do a deep dive into the nearly $2 trillion dollar employee benefits market, including structural issues that actually give the smallest companies the most leverage. We also talk insurance more broadly, AI opportunities in insurance, lessons from kickstarting a marketplace doing nearly $3B in volume, and when his wife got cancer two months after closing Threeflow's seed round, and how his co-founders adjusted to support him. Thanks to @boltdotnew for supporting this episode + to @thejoefloyd and @Rick_Zullo for introducing me to Ryan and help brainstorming topics! Full episode here on X or links in the replies. Timestamps: 3:57 Threeflow: B2B benefits marketplace 5:50 How the benefits industry works 9:20 The importance of brokers in insurance 12:32 Benefits broker software stack 15:36 How to make money in employee benefits 21:11 Ways to compete in insurance 26:34 How AI is changing insurance 31:01 What its like to be an insurance broker 35:37 Starting ThreeFlow in 2016 pre-LLMs 40:13 The 128 day walk through Europe before Threeflow 44:47 When his wife was diagnosed with breast cancer 50:23 Advice for founders on surviving large personal events 52:46 Threeflow’s unorthodox Seed round 59:46 How to vet your investors 1:04:14 Why insurance brokers exist 1:05:08 How to build a marketplace on top of Vertical SaaS 1:10:53 Choosing a marketplace entry point 1:15:05 $2.5B in premium volume on Threeflow workflows 1:26:39 Importance of supply side volume in a marketplace 1:31:21 Fundraising without a formal process 1:33:03 Hiring for “just get stuff done” 1:36:22 AI opportunities in insurance 1:41:05 Building software in insurance 1:44:56 Tactics for running a distributed team 1:49:04 Creating your own playbooks