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PRESS KIT, UPDATED SEPTEMBER 2026

Gregory Scott Henson

Serial founder, angel investor, and operator. Everything on this page is approved for publication without asking first.

Gregory Scott Henson is Founder and Chief Executive Officer of SocialPost.ai, Chairman of the Board of ALIANDO, Founder and Managing Partner of Henson Venture Partners, and Founder and Executive Director of Cloud Veterans. He founded Henson Group in 2002 and led it as CEO until 2021.

Current Roles and Titles

Venture-backed and profitable AI platform, used by more than 15,000 businesses

FOUNDER & CHIEF EXECUTIVE OFFICER

SocialPost.ai logo with the tagline AI that knows Social Media

Pre-seed and seed software investing

FOUNDER & MANAGING PARTNER

Henson Venture Partners wordmark

Global Microsoft partner formed from the Henson Group and MyCloudDoor merger

CHAIRMAN OF THE BOARD

ALIANDO logo

Nonprofit moving veterans into tech careers

FOUNDER & EXECUTIVE DIRECTOR

Cloud Veterans logo, winged emblem with the Cloud Veterans wordmark

Fact Sheet

Use this as the source of truth. If another page contradicts it, this page is correct.

FULL NAME

Gregory Scott Henson

KNOWN AS

The Startup King

CURRENT ROLES

CEO, SocialPost.ai. Chairman of the board, ALIANDO. Founder and managing partner, Henson Venture Partners. Founder and executive director, Cloud Veterans.

ALSO FOUNDED

Cloudify (agentic AI), BlackBunker (veteran-staffed 24/7 SOC and managed detection and response), ChubbyNoMore (GLP-1 telehealth)

CAREER STARTED

1996, Perot Systems, Dallas. Then Microsoft Consulting Services, New York, 1996 to 2002.

FIRST COMPANY

Henson Group, founded February 2002 in a one-bedroom New York apartment. CEO until 2021, chairman through the 2025 merger.

BASED IN

Miami, New York City, Dorado (Puerto Rico), and Dallas. He does not have a single home base.

EDUCATION

Baylor University (dual major, Management and Information Systems). Wharton Executive Education, The Wharton School.

LANGUAGES

English (native), Spanish (professional working proficiency)

FAMILY

Husband to Grennessys, father of three sons

Approved Bios

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SHORT

Gregory Scott Henson is the founder and CEO of SocialPost.ai, chairman of the board at ALIANDO, and founder and managing partner of Henson Venture Partners. He founded Henson Group in 2002 and grew it to $70M in annual revenue with no outside capital. He also runs the nonprofit Cloud Veterans.

MEDIUM

Gregory Scott Henson is a serial founder and angel investor known as The Startup King. He founded Henson Group in 2002 from a one-bedroom New York apartment and grew it to $70M with zero outside funding, becoming the top Azure cloud solution provider globally and reaching number 132 on the Inc. 5000. In 2025 he architected its merger into ALIANDO, where he is chairman of the board. He is CEO of SocialPost.ai, a venture-backed and profitable AI platform used by more than 15,000 small businesses, and managing partner of Henson Venture Partners. He founded the nonprofit Cloud Veterans in 2019.

Long bio

Gregory Scott Henson has founded twenty companies, run four of them as CEO, and backed more than fifty as an angel investor. Founders call him The Startup King.

​

He was working at Microsoft in New York on September 11, 2001, and watched businesses in lower Manhattan struggle to rebuild. He started volunteering his nights to move their systems, then left Microsoft to do it full time. That was Henson Group. He ran it out of a one-bedroom apartment and was the only employee for nine months, doing free migrations for companies getting back on their feet. Nineteen years later it was one of Microsoft's largest partners, at $70M in annual revenue, the top Azure cloud solution provider globally, and number 132 on the Inc. 5000. It never took a dollar of outside funding. In 2025 he architected its merger with Spain-based MyCloudDoor to form ALIANDO, where he is chairman of the board.

​

Today he is CEO of SocialPost.ai, a venture-backed and profitable AI platform that turns what ChatGPT and Claude write into brand-correct posts across every channel. More than 15,000 small businesses use it. Through Henson Venture Partners he writes pre-seed and seed checks up to $500,000 into US software founders on transparent SAFE terms.

​

He founded Cloud Veterans in 2019 to move veterans into tech careers. Every dollar he earns from paid advisory sessions goes to it. He lives between Miami, New York, Dorado, and Dallas with his wife Grennessys and their three sons.

Photos

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Figures Worth Citing

Where a number can be checked against a third party, the source is named.

$70M: Henson Group annual revenue at its peak, built with zero outside funding. Source: Company financials, self-reported.

#132: Inc. 5000 rank in 2020, at 2,809.3% three-year growth. Source: Inc. 5000 company profile, inc.com.

#1,638: Inc. 5000 rank in 2008. Source: Inc. 5000 company profile, inc.com.

$120M: ALIANDO annual revenue, roughly 500 people across 32 countries. Source: aliando.com.

15,000+: Businesses using SocialPost.ai, with 3M+ posts generated. Source: Product data, self-reported.

$1M: SocialPost.ai seed round, led by Ember Venture Capital, September 2025. Source: Refresh Miami, FinSMEs, The SaaS News.

$500K: Largest check size at Henson Venture Partners, 27 companies backed. Source: henson.vc.

50 / 20 / 4: Startups backed as an angel, companies founded, companies run as CEO. Source: Self-reported.

2019: Cloud Veterans founded. 1,000+ veterans placed in tech roles since.. Source: cloudveterans.org.

Enterprise clients served over his career include Microsoft, Goldman Sachs, Disney, the NFL, Equinox, Movado, and Tiffany & Co.
 

What to Book Him For

He gives straight answers and specific numbers. He is not a good fit for panels about the future of anything.

Bootstrapping to $70M

What actually compounds when you have no outside capital, and what breaks at each revenue stage.

What investors really look for

Live pitch teardowns from the other side of the table. He has written checks he regrets and will say why.
 

Running a company on AI

How a profitable AI company uses AI internally, with the parts that did not work included.
 

Selling and merging a services business

He architected a cross-border merger into a $120M business. Valuation, earnouts, and what founders get wrong.
 

Microsoft partner strategy

Twenty years inside the ecosystem, from mainframe integration to the top Azure CSP spot.
 

Veterans in tech

Why he built Cloud Veterans, and what hiring managers keep misreading on a military resume.

He has presented for veteran startup cohorts including PenFed-sponsored programs, and takes paid one-on-one sessions through Intro. Every dollar of those fees goes to Cloud Veterans.

Watch: Gregory Scott Henson speaking at Microsoft Ready with then Microsoft Corporate Vice President Gavriella Schuster and Chad Young, IT Director at iSolved.
 

Speaking and Appearances

Coverage

Independent reporting

Company announcements

Press releases issued by the company and distributed over the wire. Picked up by outlets including Yahoo Finance, Business Insider, Digital Journal, StreetInsider, and Morningstar.

Working on a story? Everything you need is on this page.

Bios, photos, titles, and figures are pre-approved. For anything else, email hello@gregoryscotthenson.com and put your deadline in the subject line.

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