T.A. McCann

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Latest — Jun 20, 2025

Surfing a Hundred-Foot Wave - entering very competitive markets

In the small coastal town of Nazaré, Portugal, there’s a wave so massive it seems almost supernatural. Towering over 100 feet, it crashes with the force of a collapsing building. Most people run from it. A few dream of riding it. One person did it first: Garrett McNamara. In

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Understanding the Roles of AI: Co-pilots, Assistants, and Agents

In today’s fast-paced technical landscape, artificial intelligence (AI) is becoming an integral part of our daily lives, transforming how we work, communicate, and solve problems. As someone who has navigated the evolving world of startups and technology over the last 30 years, I’ve seen first-hand how these AI

Creating a great startup investor pitch - the “hourglass approach” and 10Ps

As an entrepreneur, securing funding is one of the most critical steps in bringing your idea to life. The pitch process is your opportunity to convince investors that your startup has potential. While there are many examples of presentation decks online, I developed a version of a way to think

My executive assistant gives me superpowers, and you can get some too.

Managing a hectic professional schedule can be challenging, especially when you have multiple projects, like me, and I'm sure many of you. To tackle this, I’ve had EAs (Executive Assistants) since 2011 and VAs (Virtual Assistants) since 2019, and while they are all virtual/remote, I still

Getting Connected in Seattle

During the recent Tech Week, I met so many people new to Seattle. A number of them asked me; what the best ways are for them to become more connected to the ecosystem. So, I decided just to put a quick list together. * GeekWire events, especially the Summer Rooftop Party,

Founder-idea fit and the “First Five” - some tactics on startup team building

If you’re a founder, what are your 3-5 bullet points on “founder-idea fit”? Who are your “first five”? And, what are the core attributes of your culture that set you apart from the pack? It’s worth the time to answer these questions (over and over again)!

BITW - Best In The World

My partner at PSL, Greg Gottesman, often asks entrepreneurs, “What will you be best in the world at?” I think this is a great prompt and forces the entrepreneur to consider not only the direct answer to the question but also what's unique about themselves, what's

Embracing Design: Madonna's Fashion Evolution and Influence

A few weeks ago, I went to see Madonna. I've been a fan since college, and I'd never seen her live. At this point, she's 65 years old and still performing in some amazing ways, albeit with a knee brace. One thing that really

Getting the most from your board meetings: The Five D's Strategy

In my years of experience (founded five companies and been on > 20 boards…), I've found that the key to a successful board meeting lies in preparing and structuring, and running a good board meeting. In preparation, I prefer using a Google Document vs. Deck (Google Slides/PPT)

The history channel (memories for startups)

Startups move fast and if you’re doing it right, you make a ton of progress on everything from customers, product, team, systems, press…very quickly and it’s easy to lose track. And, since most leaders are very focused on the future and what’s next, they forget to