S4E01 — Protect the King: Business Lessons From a Live Chess Game - Tyler Otto

Tyler Otto and Alex Roman have been playing chess for about two years, usually taking a day or three to make each move. For the Season 4 premiere of Humans in Accounting, they finally played a game live, and talked business between moves. Tyler runs a 16-person accounting firm that now operates day to day without him, co-hosts the Unaccountable podcast, and does his best work the same way he plays chess: fast, and on the fly. In this episode, Tyler and Alex play a 10-minute game while exploring what chess can teach business owners: when to follow the playbook and when to leave it, why giving up material can be the right move, and how protecting the king looks a lot like protecting company culture. Tyler also shares why his firm walked away from nearly $26K in monthly recurring revenue, what he learned after losing a big part of his team in a single month, why owning your mistakes in front of your team matters, and his advice for anyone who thinks it's too late to start a firm. Topics covered: • Playing a live chess game while talking business • How Tyler got into chess • Why Tyler does his best work on the fly • Knowing when to leave your playbook • Walking away from $26K in monthly recurring revenue • How Tyler inspired Humans in Accounting • Knight or bishop? What your piece says about you • Trading resources to get closer to your goal • Losing a big part of the team in one month • Protect the king: protecting company culture • Reviewing your losses • Owning your mistakes in front of your team • Advice for starting an accounting firm in 2026 Humans in Accounting is brought to you by South Offices, connecting accounting firms with skilled professionals across Latin America. 🎧 South Offices Home https://southoffices.com/ 🌎 Nearshore Accounting Company https://southoffices.com/nearshore-ac... 📞 Talk to a CPA-led Nearshore Team Specialist https://calendly.com/alex-southoffices Timestamps 00:00 Intro 00:43 Welcome to Season 4 01:12 Chess meets business: a podcast first 02:21 How Tyler got into chess 05:15 Why Tyler plays (and works) best on the fly 07:55 When your playbook stops working 09:54 Walking away from $26K in monthly revenue 10:32 How Tyler inspired this podcast 12:37 Tyler's favorite food 14:03 Knight or bishop? 16:31 Giving up material to reach your goal 17:42 Parenting time off and over-the-board chess 21:21 When a big part of the team left 22:30 Protect the king, protect the culture 24:21 Learning from your losses 25:11 Owning mistakes in front of your team 30:07 Advice for starting a firm in 2026