Wegener got his early education at Friends' Central School. He got his love for the internet in 1997 when he made a website that showed people how to download South Park online and it hit 80,000 views. Wegener went on to earn his BA from Columbia University where he studied Neuroscience, Sociology, and Marketing. During college he made a professor review website called Culpa.info that collected ~3 million views a month. 
While he was still in college, Wegener spent a little under a year as a laboratory research assistant at Columbia University Medical designing experiments to treat cocaine addiction. After graduation, he got into digital media strategy for US newswire service, Mitchell Madison Group. His next gig was at Pontiflex doing marketing, PR, and business development for the small tech startup.
In 2008 Wegener founded JWeg Ventures LLC as a holding company several different projects he was working on. He founded Exit Strategy NYC in 2009, a comprehensive subway planning app that's been covered by The New York Times, New York Post, New York Magazine, Wired, NY1, and several other publications. Another project was FindtheMohel.com, which is a lead generating website that helps people find a Mohel for their baby's bris. He developed a prototype for an app called PeerAround.com that used data from Foursquare, RapLeaf, and Twitter to help people learn about their peers. He also did a ton of consulting between 2008 and 2010 with the following companies: 
- At GroupMe he worked in product design, analytics.
- At Loosecubes he worked in iPhone App wireframes.
- At AppFund he worked in product design and strategy.
- At Dense brain he produced functional specification document and use cases for a large brand's facebook app.
- At Drop.io he managed product launch marketing for site redesign. Managed social-media channels, blogger outreach; wrote press releases and marketing materials.
- At SkillSlate he worked on SEO strategy and HTML optimization.
- At MyMohel.com he implemented SEM campaign and call tracking solutions.
- He also designed websites and created SEM/SEO strategies for several local businesses (dvirsalon.com, lenakoro.com, brooklyndogwalk.net, yourbestcollegeessay.com)
In 2011 Wegener cofounded popular digital photo album, Timehop. Wegener did everything from washing dishes to raising $14 million in VC funding from Spark Capital, OATV, and Shasta Ventures. He went on to Snap Inc. where he worked as a product designer for a little under a year. In 2018 he started building an app called NewCo.