Back from Boston: New View on AI

I just boarded an Amtrak train at Boston’s South Station after attending the MarketingProfs B2B Forum for the second year in a row. As the organizers noted, more than 800 digital marketers from across the country were in attendance — a full day of learning, sharing, and discovering new ideas.

One of the standout sessions for me was a workshop led by Andy Crestodina, co-founder of Orbit Media Studios in Chicago, an award-winning digital marketing and web development firm that has built more than 1,000 websites across industries.

Andy’s session, “AI for Content Creation and Lead Generation,” focused on how to write enhanced prompts for tools like ChatGPT to get deeper, clearer, and more useful answers. Rather than typing a simple one-off question like:

“How much money has been deposited into the U.S. Treasury from tariffs?”

Andy showed how to expand the prompt so the AI knows the role, audience, and format before answering. For example:

You are an expert economic analyst who writes for a professional audience (economists, policy-makers, advanced business readers).
Your task: Provide a clear, up-to-date overview of how much revenue tariffs bring into the U.S. Treasury.

By adding this framing before the question, the user is “shaping the context window,” as Andy put it — defining how the AI reasons and how it continues the conversation. You can also add more parameters, such as:

  • Include the most recent full fiscal year and, if available, the current year to date.
  • Break down by major tariff categories and note trends compared to previous years.

When I asked ChatGPT to respond using the first two parameters, here’s what it returned:

Most recent full fiscal year
In FY 2024, the U.S. collected about $77 billion in customs duties (tariffs and related fees).

Year to date (most recent available)
As of August in FY 2025, customs-duties revenue totaled about $165.2 billion, roughly a 137% increase over the same period in FY 2024.

Seeing the difference made the point clear: enhanced prompts unlock more complete and more context-aware answers.

This was my biggest takeaway from Andy’s workshop. He has also published a book, “Content Chemistry” — now in its 7th edition — that dives even deeper into these methods.

I’m glad I attended the B2B Forum again this year, and I expect to be back next year. Plenty to think about on the train ride home.