Outsourced IT Done Right with Ann Cloyd (EP 1047)

Ann Cloyd, CEO and co‑founder of Deep Tech Inc., joins me to share how she took a Mac‑focused niche supporting New York art galleries and turned it into a 30+ person, dual‑platform IT services company serving both Mac and Windows clients. She walks through why she positions Deep Tech as an outsourced IT department instead of “just an MSP,” how staying hands‑on with clients and committing to on‑site visits has built long‑term relationships and word‑of‑mouth growth, and why acquisitions became her preferred path to scale without losing that in‑the‑trenches feel.

We also dig into Ann’s vision for Tech Bloom, a nonprofit apprenticeship program that pays women to learn tech support through real client work, mentorship, and a strong professional network. The big takeaway: if you want your help desk and day‑to‑day support to be a real growth engine, you need to treat relationships as a core asset, show up in person when it counts, and think creatively about building your own talent pipeline—whether that’s through acquisitions, apprenticeships, or partnership with programs like Tech Bloom.

=== Chapters

• 00:39 West Coast Versus East Coast
• 04:07 Art Gallery Beginnings
• 07:58 Going Dual Platform
• 09:50 Peer Groups and Women
• 13:13 Launching Tech Bloom
• 18:21 Building a Support Network
• 21:41 What Makes Deep Tech Different
• 25:29 Drive and Business Growth
• 28:46 Goldman Sachs Lessons
• 32:22 Staying Hands-On With Clients
• 37:32 Why Not Call It MSP

=== Guest: Anne Cloyd, Deep Tech Inc.

• Website: https://deeptechinc.com
• LinkedIn: https://www.linkedin.com/in/anncloyd/

=== Companies / Vendors / Products / Books

• Tech Bloom Apprenticeship Program: https://tech-bloom.org
• Goldman Sachs 10,000 Small Businesses: https://www.10ksbapply.com
• Goldman Sachs: https://www.goldmansachs.com
• FileMaker Pro: https://www.claris.com/filemaker

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