My friend, mentor, and one of the smartest people I know, T.A. McCann, has been a guiding force in my career for more than two decades. He’s one of those rare people who can operate at 30,000 feet, seeing the entire landscape of technology and business, and then dive down to ground level to offer the most practical, actionable advice for a creator just starting out. He’s a founder, an investor, a venture studio managing director, and someone who fundamentally understands the heart of an entrepreneur.
T.A. has a long and storied career as a serial entrepreneur. He was the founder of Gist, a popular contact management tool that was acquired by BlackBerry, where he then served as a VP. He also cofounded Rival IQ, a marketing analytics company, which was later acquired as well. Today, he’s a managing director at Pioneer Square Labs (PSL), a Seattle-based startup studio and venture capital fund that helps build and launch new companies. His entire career has been about identifying problems, building solutions, and helping other founders do the same.
What makes T.A. unique is his deep empathy for the creative journey. He sees the parallels between building a venture-backed tech company and a solo photography business. He understands that at the core of both is a person with a passion, a vision, and a whole lot of questions about how to make it real. He’s not just a mentor to me; he’s a mentor to our entire creative community, whether he knows it or not.
Over the years, T.A. and I have collaborated on countless projects, from casual brainstorming sessions over coffee to more formal work. He’s been a guest on my podcast, The Chase Jarvis LIVE Show, multiple times, sharing his wisdom on everything from fundraising to founder-idea fit. You can find our recent series of conversations right here, and I highly recommend you dive in. While he wasn’t directly involved in the founding of CreativeLive, his strategic thinking has been an invaluable resource I’ve drawn upon for years as we’ve built and grown the company. His fingerprints are on my own journey in a thousand different ways.
T.A. has a gift for cutting through the noise and offering frameworks that you can apply to your own life immediately. Here are a few of the most powerful concepts we’ve discussed that I think can help you find your path.
Find Your Founder-Idea Fit
The world is full of good ideas, but not all of them are good ideas for you. The most successful creators and entrepreneurs find the perfect overlap between their skills, their passions, and a market that needs what they have to offer. T.A. visualizes this as a Venn diagram with three intersecting circles: What are you good at? What are you interested in? And what kind of customers do you want to serve? When you find the sweet spot in the middle, you’ve found a powerful foundation for a business.
How to Apply This:
- List Your Skills: Write down 5-10 things you are genuinely good at. This isn’t about what you wish you were good at, but what your skills actually are today.
- Explore Your Interests: Imagine you’re in a magazine shop. Which section do you walk toward? Business, art, tech, nature? List the topics you are naturally drawn to, the things you read about for fun.
- Identify Your People: Who do you want to help? Who do you want to spend your time with? If you don’t genuinely enjoy the people you’re serving, the work will become a grind, no matter how much money you make.
- Write Your “Why Me?” Statement: Combine the answers above and write 5 bullet points explaining why you are one of the best people on the planet to start this specific business or project.
Develop a Bias for Action
Talk is cheap. Whining is even cheaper. T.A. notes that the biggest difference between those who succeed and those who stay stuck is a “bias for action.” Entrepreneurs see a problem and immediately start testing solutions. They don’t list all the reasons it won’t work; they find one reason it might and take a step forward. This doesn’t mean being reckless, but it does mean choosing motion over stagnation. If you find yourself complaining or listing all the reasons you “can’t” do something, it’s a red flag that you have a bias for inaction.
How to Apply This:
- Take One Small Step: Instead of planning your entire business, what is the smallest possible action you can take today? Can you email one potential customer? Can you design a logo sketch? Can you buy a domain name? Do it now.
- Timebox Your Decisions: Don’t get lost in “analysis paralysis.” Give yourself one hour to research three options, then pick one and move forward. You can always adjust later. Action creates clarity.
- Surround Yourself with Doers: Pay attention to who you spend your time with. If your circle is full of people who complain and make excuses, you will too. Intentionally seek out people who are building, creating, and taking action. Their energy is contagious.
Get Close To It
One of the biggest hurdles is the giant gap between “I’m interested in this” and “I’m quitting my job to do this.” You don’t have to jump across the chasm in one leap. The key is to find low-risk ways to get closer to the thing you’re curious about. This allows you to learn, test your assumptions, and see if you actually enjoy the reality of the work before you blow up your life.
How to Apply This:
- Offer Free Help: Find someone who is doing what you want to do and offer to work for them for free in a very structured way. For example: “I will work for you every Tuesday night from 5 to 10 p.m. for the next month.” It’s an offer almost no one will refuse, and you will learn an immense amount.
- Use Your Vacation Time: Instead of a typical vacation, use that week or two to do a short, intensive internship or project in your desired field. Frame it as a learning experience with no strings attached.
- Become an Assistant: Get on the team, any way you can. Carry the bags, make the coffee, organize the closet. Being in the room where it happens is an education you can’t get from a book. Once you’re on the team, raise your hand for every opportunity.
PS – If you’re looking for a guide to help you build the life and career you’ve always wanted, the Seven Levers for Life is a free 7-day email course on just that.
