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DeMario Phipps-Smith

DeMario Phipps-Smith

Reporter

DeMario is a writer and journalist from Chicago. He is a former digital editor at the Chicago Sun-Times and has bylines in such publications as Blavity, Eat This Not That, and the National Football Foundation.

After creating a media startup in 2015, DeMario is passionate about entrepreneurship and business. Currently, he is a graduate student at Northwestern studying media innovation.

SaaS

A self-taught developer used a low-code tool to build this text messaging app

Smooth Messenger’s founder went from growing his skills in Zoho Creator fresh out of college, to building and selling an app powered through the platform.

A smiling main in a plaid button up shirt stands in front of a white wall and open window
Content

Content site on backyard recreation sells for about 3.3x annual revenue

Spencer Haws grew Own The Yard, a blog dedicated to backyard life, as a public case study, showing the power of content websites. He sold it three years after launch.

E-commerce

They developed beard-grooming products for men of color, then sold to an e-commerce company for global distribution

Centering on the grooming needs of underserved Black men, the Fresh Heritage founders believed they had to sell to a buyer that really understood and respected their mission.

Platform

Podcasters wanted to sell subscriptions, so she built a platform to help them monetize

Founder Amira Valliani built Glow to support podcasters who wanted to grow their business. Two years later, she sold the platform to podcasting giant Libsyn.

A woman smiles at the camera
Content

This company solved a common challenge — choosing a business name — and sold for 8 figures

Coming up with a good business name isn’t easy. Domainify Group built tools to help, and then sold for 8 figures to affiliate marketing company Game Lounge.

SaaS

With $330,000 ARR and 10,000 paid subscribers, fashion app Cladwell is acquired

Cladwell, which helps users style outfits from the clothes already in their closet, hit a growth ceiling, so its founders eyed a sale.

Cladwell team in 2013, with a baby
Content

Testing.org, which helps exam takers prep for LSAT, CPA and Bar, sold to strategic buyer

Founded by media entrepreneur Michael Gardon in 2017, Testing.org was an appealing addition to buyer Crush Empire’s portfolio of education websites.

Mike Gardon, founder of Testing.org
Services

A marketing company used software to service publishers, then sold to its tech partner

What happens when one of your company’s partners wants to turn that partnership into an acquisition? That was the case for these three founders.