Could Your Business Survive a 2-Month Vacation? | Kevin Ziegler (#112)

If you left your business for two months and went unreachable, would it still run? Kevin Ziegler learned the cost of key person risk the hard way when his co-founder was diagnosed with bone cancer and he sold his share of a 13-year software firm faster and cheaper than he should have. Kevin is a Milwaukee-based fractional CTO and four-time founder who co-founded Freight iQ, a logistics SaaS that reached $6 million in ARR, and now embeds with growing transportation and logistics companies on AI strategy, governance, and TMS selection. Want to know what makes your logistics business worth more? Download the free Business Value Cheat Sheet: 10 Steps to Increase the Value of Your Business: https://bizexitgrow.com/cheat-sheet Kevin says key person risk is a technology problem too: the one person who knows how to write the code or run the software is a liability a buyer will price. In this episode: – Why Kevin sold too fast and what a finance advisor taught him about asking "what is important to me" – The two-month vacation test and how to document your way out of being the bottleneck – Kevin's three-stage fractional CTO process: assessment, roadmap, advisory – How to pick a TMS with a requirements list and a one-to-five vendor scorecard instead of a referral and a sales call – Why building your own AI tools is riskier than it looks if you are not a software shop – AI governance first, then low-risk agents with a human in the loop, then cost controls before tokens get out of hand – Why the real AI bottleneck is not enough planned work, and the opportunity that creates for analysts and product owners Connect with Kevin: https://www.linkedin.com/in/kevinmziegler | https://kevinziegler.com Chapters 0:00 Welcome and guest introduction 1:06 From orthodontist track to software founder 3:06 Building a logistics software agency from 1999 4:20 A co-founder's cancer diagnosis and a rushed exit 5:30 The two-month vacation test for key person risk 6:26 Documentation, SOPs, and hiring people better than you 8:20 Why you need a five-year exit horizon and an advisor on your side 10:03 What a fractional CTO fixes first: risk, security, documentation 10:50 Kevin's three-stage process: assessment, roadmap, advisory 13:10 How to pick a TMS with a mini RFP and scorecard 16:28 Build versus buy in the AI age 18:29 AI governance, agents, human in the loop, and runaway costs 22:48 How Kevin uses AI agents and structured vibe coding 25:41 Where AI disrupts and where it creates jobs 28:53 Kevin's practical takeaway #ExitAlgorithms #KeyPersonRisk #LogisticsTech