Most businesses spend months trying to adapt to software that was never built for them, wrestling with clunky systems, patching gaps with spreadsheets, and wondering why teams avoid the tools they paid for.

In this episode, Abi Walsh sits down with Trevor Bollers, President of Letter B Global Technologies, a custom software development company built on a different idea: design software around the culture of your business, not the other way around. Trevor brings experience from the NFL, logistics, and two decades in tech, applying the discipline he learned on the field to every client engagement.

Trevor explains what he calls cultural design, starting with how a business actually operates before writing a single line of code. He shares why spreadsheets are often the clearest signal of software failure, how Letter B connects onshore strategy with offshore delivery, and what MSPs often miss when approaching AI.

Key Takeaways:

Your spreadsheets reveal the truth about where your software is failing and where work is actually happening
Cultural design means building software around how your team thinks and works, not forcing them to adapt
Most AI tools are used like search engines, but real value comes when AI connects directly to your business data
Integrated AI understands your customers, pipeline, and patterns, helping surface what needs attention next
MSPs should use software partnerships to strengthen client relationships, not replace them, and scale gradually
Security and AI contracts differ, and business owners need clarity on where their data actually goes
AI may reduce execution-heavy offshore work, but strategic, consultative thinking remains essential
Building through the 2008 downturn taught the importance of discipline that carries through cycles

Connect with Trevor Bollers on LinkedIn: [https://www.linkedin.com/in/trevb/](https://www.linkedin.com/in/trevb/)
Visit Letter B Global Technologies: [https://www.letterbglobal.com](https://www.letterbglobal.com)
Email: [tbolllers@letterbglobal.com](mailto:tbolllers@letterbglobal.com)

I hope you enjoy this episode! Give it a like, share, and subscribe to not miss the content coming your way weekly.

– Abi and the Profit. Grow. Exit. podcast team

Connect with Abi Walsh on LinkedIn: https://www.linkedin.com/in/abiwalsh/
Visit the Encore Strategic website here: encorestrategic.io

Listen to Profit. Grow. Exit on these Platforms:
YouTube: https://www.youtube.com/channel/UCRvlZ82qYZ3_5G2B-sPpaLw
Spotify: https://open.spotify.com/show/0x5v7BQunMtbNsFLSoZTvR
Apple:​ https://podcasts.apple.com/us/podcast/profit-grow-exit/id1891305118
Amazon: https://music.amazon.com/podcasts/00643a88-8d90-4a94-ba91-3505f8e4f84b

#ProfitGrowExit #AbiWalsh #MSPBusiness #ManagedServiceProvider #MSPGrowth #BusinessExit #ExitPlanning #MSPOwner #BusinessStrategy #PeerGroups #BusinessScaling #SmallBusinessGrowth #EntrepreneurMindset #BusinessOperations #MSPSuccess

Profit. Grow. Exit. is the podcast for MSP owners who are ready to stop being the best technician in their business and start being the best operator. Hosted by Abi Walsh of Encore Strategic, each episode delivers straight-talking insight on building a profitable, scalable, and sellable managed service business — from knowing your numbers to building the team that lets you step back. Most MSP owners built a high-paying job, not a company — and it doesn't have to stay that way. If you're stuck at a plateau, unsure of your exit path, or ready to run your business like a real business, this podcast is for you.