Blog - Siskar.com | Kevin Siskar

We usually tell the story of entrepreneurship through the lens of companies: the idea, the product, the raise, the team, the exit.

For the last two years, almost every conversation about AI and work has started with the same question: Are software engineers going away?

There is a lazy belief floating around startups that often gets disguised as pattern recognition: If this company could have broken out, it would have by now.

Wether they realize it or not, everyone is playing a game.

Machines specialized to the factory floor; I think software will specialize to the workflow floor.

From 4K to 1M to 1B to 1T: If you want to understand where AI is going, let’s stop staring at “IQ” benchmarks for a minute and look at memory.

How the Object in Our Hand Reveals Each Era’s Interface… …And Why the Next One Won’t Need a Hand at All A Quick Look in the Rear-View Mirror In the 1950s and ’60s, cigarettes served as social passports.

From radio → video → internet → AI — each wave doesn’t just add a new format.

The Long Arc of “Getting Online” (1995–2025) Twenty-nine years ago during the dot com boom, barely 1 in 40 people alive today had ever typed a URL.

What’s Happened So Far: To better understand where we are going, let’s first look at where we are coming from.

With Veterans Day upon us, I’ve had some thoughts.

During NY Tech Week 2024 Finta hosted a live panel discussion in midtown Manhattan on the state of fundraising in 2024.

Over 100+ billion humans have existed before us… When I first heard this number a few years ago, it was kind of mind blowing.

Finta is on Product Hunt today!

Lorenzo Thione, Managing Director of Gaingels We sat down with one of the most influential people in tech, Lorenzo Thione, who shares his very inspiring journey and how that led him to be where he is today.

Kevin Siskar, Millenial Investing Podcast Recently, I had the opportunity to sit on the opposite sit of the podcaster’s table to be a guest on the Millennial Investing Podcast!

Jordan Levy | SEed Capital Partners (SBNY) In the fall we sat down with one of the godfathers of Venture Capital, Jordan Levy, who shares his very inspiring founder story and how that led to his career as an investor.

Surprise!

With over 55,000 students and over 1 million minutes watched on my previous Skillshare classes, I am excited to announce my newest class on how to set up workflow automations!

Happy New Year to you and your family!