2026: The New 2016? 🔮

⏰ Midwest Minute 

A decade later, 2016 still refuses to log off. The memes that defined 2016 never really disappeared. The short-video format that was born on Vine (which just might make a return this year), Tumblr and the commentary from the first few years of Twitter still dominate comment sections today. The music from that year has followed the same arc. Albums like ANTI by Rihanna, Coloring Book by Chance the Rapper and Blonde by Frank Ocean are regularly rediscovered by younger audiences through short-form video. Songs released a ten years ago continue to chart on streaming platforms thanks to viral clips, proving that 2016 wasn’t just a good year for music, it was a foundational one for how culture circulates online. Lately, feeds on Instagram have filled with photos from the summer of 2016. As Gen Alpha—raised on short-form video and algorithms—starts treating the 2010s the same way millennials once romanticized the early internet, officially turning a not-so-distant decade into nostalgia.

Fashion tells the same story. Clothing trends are looping right along with it—quarter zips, straight-leg denim pared-back fits with an all-around more preppy feel are making a return, all while matcha has quietly replaced iced coffee as the “it” drink, turning 2016’s normcore into today’s default aesthetic. TikTok has accelerated trend recycling at a pace that didn’t exist ten years ago. What’s new this time is AI. Tools now generate short-form videos, auto-edit clips, recreate voices and remix memes—effectively cloning the creative behaviors that apps like Vine, Instagram and Snapchat trained users on in the first place. The result feels familiar for a reason: 2016 taught the internet how to create. 2025 is watched AI learn how to replicate it. 2026 is now all about authenticity.

Have any insights into the Midwest ecosystem or a funding announcement to share? Want to share a favorite memorie—perhaps from the summer of 2016? Send us an email: [email protected] 

📰 Notable News

Exits

• Chicago-based Obie acquired by The Baldwin Group for an undisclosed amount  

• Minneapolis-based Encore Medical filed for IPO

Startup Funding

• Skild AI - $1.4B at a $14B valuation led by SoftBank | Pittsburgh

• CHAMP Titles - $55M round co-led by W. R. Berkley Corporation, Point72 Ventures, and ORIX Corporation USA | Cleveland

• Trailhead Biosystems - $20M round led by MAK Capital | Cleveland

• PayMedix - $16M in equity funding led by HLM Investment Partners | Milwaukee

• Aether Fuels - $15M in funding from Aster Ventures and EDBI and existing investors | Chicago

• Amphix Bio - $12.5M Seed from undisclosed investors | Chicago

• Enspire DBS - $10.3M Series B led by Genesys Capital | Cleveland

• Auxira Health - $7.8M Seed co-led by Route 66 Ventures and Abundant Venture Partners | Chicago

• Onsetto - $2.2M Seed led by EJF Ventures | Minneapolis

• Rayni - $1.8M round led by HPVP | Chicago

VC Funds

• Grit Road Partners - Announced First Close of Fund II | Omaha

Other News

• U.S. VC Female Founders Dashboard

• 2025 U.S. PE Breakdown

• JPMorgan Chase says banks could fight Trump credit card rate cap: ‘Everything’s on the table’

• CrowdStrike acquires browser security startup Seraphic for $400 million

• How a federal quantum bill could accelerate Illinois' tech ambitions

• Chicago ranked 9th best city for startups — here's why

• In 2026, AI will move from hype to pragmatism

• Why the electrical grid needs more software

Have exciting news to share? If you're announcing a funding round, exit or other milestone, send your press release to [email protected] to be featured. While we can’t share everything, we love to feature great stories from across the region.

📆 Mark your Calendar

Need to fill your social calendar? We’ve scoured newsletters, scanned LinkedIn and found some of the latest tech + startup events in the region. Know of any upcoming events and want to share them in our next newsletter? Send us an email: [email protected]