Gregory Scott Henson

$70M ARR bootstrapped. 50X angel investor. 20X founder. 4X CEO.

In 2002 I ran a company out of a one-bedroom apartment in New York. For the first nine months, I was the only employee.

That company was Henson Group. I started it after 9/11, doing free IT migrations for businesses trying to rebuild out of lower Manhattan. It grew into the #1 Azure CSP in the world and #132 on the Inc. 5000, on zero outside funding. I merged it with MyCloudDoor in 2025 to form ALIANDO, a 400+ person global Microsoft partner doing $120M ARR, where I now serve as Chairman of the Board.

Today I am CEO of SocialPost.ai, a venture-backed and profitable AI platform used by 15,000+ small businesses and creators, doing $600K+ ARR. I run Henson Venture Partners, writing checks up to $500K into pre-seed and seed software founders. And I run Cloud Veterans, a nonprofit that has moved thousands of veterans into tech since 2019. Every dollar from my paid sessions goes there.

I've also founded three companies I still back. BlackBunker, a veteran-staffed 24/7 SOC and MDR provider protecting SMBs in regulated industries. Cloudify, an agentic AI company building autonomous agents that do real business work. ChubbyNoMore, a telehealth brand for medical weight loss, now run by my son as CEO.

Husband and father. I write daily for founders scaling from $100K to $100M.