Entrepreneurship has always been hard. But heading into 2026, it’s becoming something else entirely. This is no longer just a test of endurance. It’s a test of reinvention. AI acceleration, hybrid work, and tighter capital markets have quietly rewritten the startup playbook. The founders who win next won’t just scale faster—they’ll adapt better. Here are the new rules I’m seeing emerge.

You just finished your first pitch deck. You think it’s strong. But you can’t shake the feeling that something might be off. Here’s the uncomfortable truth: founders are terrible judges of their own pitch decks. I was no exception. When I completed my first pitch as an Entrepreneur in Residence, I proudly presented it to a venture partner I was working with. When I finished, he laughed and said: “Everyone’s first pitch sucks.” He was right. I don’t want that to happen to you. This post covers: Why founders can’t accurately judge their own pitch Three stress tests every pitch must pass How to fix your pitch before investors do...

Several leading Boston AI and technology voices gathered to discuss how artificial intelligence is reshaping entrepreneurship, innovation, and business growth. Speakers included leaders from MIT, Northeastern, Bain Capital, Flagship Pioneering, and global AI pioneers like Yann LeCun and Andrew Ng.

Every generation of entrepreneurs believes it’s the one that can skip steps. Start earlier. Move faster. Figure it out on the fly. That story is compelling. It’s also incomplete. In a recent Fortune article, Jeff Bezos offered advice to Gen Z that cuts directly against the dominant startup mythology: get real work experience before launching a company. Bezos didn’t say this as a critic of entrepreneurship. He said it as someone who built Amazon—starting at age 30, after nearly a decade of professional experience. This wasn’t a casual comment. It was a strategic observation.

Most failed startups don’t collapse because the founders lacked intelligence, passion, or ambition. They fail because the founders started building before they fully understood what deserved to be built. That statement runs counter to much of today’s startup culture. We celebrate speed. We reward visibility. We advise founders to launch early, pitch frequently, and iterate quickly. None of that advice is wrong—but taken out of order, it becomes a recipe for wasted effort. A recent article from Entrepreneurship Handbook (via Medium Media), "The Wrong Way to Build a New Startup," highlights a pattern that repeatedly appears among early-stage ventures: founders fall in...

There’s a familiar moment many founders don’t talk about — the urge to refresh your analytics dashboard one more time, the compulsion to check how many views your latest post got, or the instinct to monitor every micro-metric that signals “progress.”This isn’t just curiosity. It’s a soft addiction — a pattern of behavior that makes us feel productive without actually moving the business forward.

One of the most important lessons I’ve learned — and one that many founders overlook — is this:Before you spend a dollar on inventory or packaging or web design, you need to know if you can get people to care. And the simplest way to do that is by building an audience. — ehandbook.comToo many startup founders rush straight to logistics: products, packaging, fulfillment, and e-commerce stores. Yet without audience interest, all that infrastructure is like building a ship without knowing whether anyone wants to sail.Why Audience Comes First. At the earliest stage, the real question isn’t “Can I build...

What if your side hustle — even something as fun as renting jet skis — could evolve into a business with purpose? That’s exactly what happened to one enterprising MBA student whose journey from lakeside rentals to portable-shower stations offers a powerful lesson in adaptability, vision, and social impact.

In 2025, we are witnessing one of the biggest transformations in the labor market — driven not by outdated industries, but by the rise of Artificial Intelligence (AI). According to Entrepreneur, more than 22,000 tech-industry workers have already been laid off this year, with 16,000 of those layoffs occurring in just one month. This shock may feel like random downsizing, but it’s part of a deeper structural shift: AI isn’t just cutting jobs, it’s redefining what kinds of work are valuable.When companies restructure to build AI-first operations, the ripple effects are far-reaching — from who gets hired, to what skills...

The Meaning Behind the Word “Enthusiasm.”The English word enthusiasm comes from the Greek adjective ἔνθεος (entheos) — literally meaning “having the god within.”Originally, to be entheos was more than just being energetic or eager. It meant being “full of god” — to have a divine spark, an inner fire, or an inspired spirit coursing within. In ancient Greek thought, poets, prophets, or visionary artists were often described as entheos — those who didn’t just act, but channeled something greater, producing beauty, wisdom or revelation in their work.Over time, as the word passed into Latin and then English, its meaning softened....