Entrepreneurship | iCloud.Info

14 'Second Wave' startups aiming to take the AI era beyond cost cutting

Fri, 02/20/2026 - 05:00

Tech Insider : Business, Style, Technology

Kylan Gibbs, CEO and cofounder of Inworld
Inworld

AI, Tech, Startups, artificial-intelligence, generative-ai, limited-synd, gaming

I stopped bartending full-time to sell ice. My company now makes nearly $3 million a year, catering to Michelin-starred restaurants in New York City.

Thu, 02/19/2026 - 11:52

Tech Insider : Business, Style

man at bar — Richard Boccato launched his ice business in 2011.
Business Insider

Small Business, editorial-sponsorship, video-to-text, small-business, Business, new-york-city, Entrepreneurship

I've been selling on Amazon for a year. After storage fees bled me dry, I'm pivoting my e-comm strategy away from it.

Thu, 02/19/2026 - 05:45

Tech Insider : Business

peak pickleball — After writing about Amazon sellers for years, the author decided to try e-commerce for herself.
Kathleen Elkins

Retail, Strategy, Startups, E-Commerce, amazon-company, small-business, Retail

I quit my $192K Microsoft job and moved to Canada — then almost everything I owned was stolen. I'm learning to rebuild from scratch.

Thu, 02/19/2026 - 05:08

Tech Insider : Technology, Business

Careers, as-told-to, Entrepreneurship, Microsoft, Careers, job-search, artificial-intelligence

I'm the CEO of a cannabis and beverage company. I start my day in Central Park with my dog and hate being surrounded by 'yes' people.

Wed, 02/18/2026 - 05:05

Tech Insider : Business, Sports

This as-told-to essay is based on a conversation with Irwin Simon, the chairman and CEO of Tilray, based in New York City. It's been edited for length and clarity.

Careers, as-told-to, CEOs, Business, Entrepreneurship, Leadership, Lifestyle

I got laid off and used my severance money to launch a startup. Here's why it felt like less of a gamble than pursuing an MBA.

Tue, 02/17/2026 - 04:17

Tech Insider : Business, Sports, Technology

Sam Perry, 40, was laid off in 2022.

Courtesy of Sam Perry

Careers, Startups, Layoffs, Entrepreneurship, Careers, Startups, mbas

After 3 years of forcing myself to love venture capital, I quit and became a silent disco DJ in Bali

Tue, 02/17/2026 - 00:00

Tech Insider : Business

Nic Huzz composite — Nic Huzz started his career at a VC firm in Australia.
Nic Huzz

Careers, Entrepreneurship, small-business, remote-work

AI's first wave was about cutting costs. The second wave is about building things we've never seen.

Mon, 02/16/2026 - 18:00

Tech Insider : Technology, Business

People watch a surfer riding a wave in Praia do Norte, Nazare, Portugal.
PEDRO NUNES/REUTERS

AI, Tech, Startups, Startups, artificial-intelligence, generative-ai, ll-ms

Dario Amodei says Anthropic struggles to balance 'incredible commercial pressure' with its 'safety stuff'

Mon, 02/16/2026 - 05:04

Tech Insider : Business, Technology, Environment

Anthropic CEO Dario Amodei
Michael M. Santiago/Getty Images

AI, Tech, AI, anthropic, safety, artificial-intelligence, Business

A Gen Zer drained her savings building a startup. A 6-figure job at Meta helped her start over — then she quit.

Mon, 02/16/2026 - 02:47

Tech Insider : Technology, Business, Economy