ai-first
(6)
Andrea Calcagno Put the Store Floor Online - Then Made WiFi Think
A Calabrian engineer followed a stubborn question from Turin to Pisa to New York: what if WiFi could do more than connect? Two decades later, Andrea Calcagno is still rebuilding the answer.
Jason Davis
Jason Davis is the co-founder and CEO of Simon AI (formerly Simon Data), a New York customer data platform that rebranded around agentic AI in 2025. A machine-learning PhD who built search algorithms at Google, he founded the ad-tech startup Adtuitive, sold it to Etsy in 2009, then ran Etsy's search and data teams as the marketplace grew from $180M to a $1B+ run rate. He and grad-school friend Matt Walker started Simon to give marketers direct, governed access to the data trapped inside their own warehouses. The company has raised roughly $117.8M, including a $54M Series D led by Macquarie Group.
Muhammad Rassam
Muhammad Rassam is a Pakistani founder and marketer who started as a blockchain engineer at the agency Antematter and pivoted into AI-first go-to-market work. He is co-founder of Ertiqah, writes the 'Efficient Entrepreneur' newsletter, serves as Chief Marketing Officer at the LinkedIn-content tool LiGo, and co-founded the cold-email platform ColdSend.pro. Based in Dubai, he is known for building lean, AI-leveraged businesses and for candid LinkedIn writing about hiring, marketing, and founder life.
Samir Deolikar
Samir Deolikar is the Chief Executive Officer of BayRock Labs, a Silicon Valley product-engineering firm in San Jose that ships AI-first software for startups and enterprises. He moved into the CEO seat in February 2024 after two years as advisor, and twenty-plus years across Zensar Technologies and Reliance Industries before that.
Tobi Lutke
Tobias 'Tobi' Lütke is the German-Canadian co-founder and CEO of Shopify, one of the world's largest e-commerce platforms. Born in 1980 in Koblenz, Germany, he received a computer at age six and left school after 10th grade to complete a programming apprenticeship, never attending university. After emigrating to Canada in 2003, he built an online snowboard shop called Snowdevil and — finding every existing e-commerce platform inadequate — coded his own solution in Ruby on Rails in two months. That solution became Shopify, which he launched as a standalone product in 2006. Shopify went public in 2015, and as of 2025 processes over $1.6 trillion in cumulative gross merchandise volume for millions of merchants across 175+ countries, commanding over 14% of the US e-commerce market. Lutke is known for his radical candor, his open-source roots, and his unusual interests for a tech CEO: competitive racing driver, avid skier, and serious gamer who credits strategy games with shaping his business thinking. His April 2025 internal memo mandating AI proficiency as a baseline expectation became one of the most widely-discussed corporate AI policy statements of the year.
Eoghan McCabe
Eoghan McCabe is an Irish technology entrepreneur born in Dublin in 1984, best known as the co-founder and CEO of Intercom — the AI-first customer service platform he founded in 2011 alongside Des Traynor, Ciaran Lee, and David Barrett. After building Intercom into a $1.3B+ unicorn over its first decade, McCabe stepped down as CEO in 2020 due to a neurological autoimmune disorder, then dramatically returned in October 2022, just weeks before ChatGPT launched. Within six weeks he had a prototype of Fin, Intercom's AI agent, and proceeded to cut roughly 40% of staff and redirect the entire company toward AI — a bet that paid off: Intercom hit an estimated $343M in revenue in 2024 (+25% YoY), raised $125M from Kleiner Perkins and $250M in debt from Hercules Capital (March 2026), and recorded its largest-ever quarter by net new ARR in Q1 FY2026.