Last week, I had the chance to step off dry land and onto Lake Simcoe for a special edition of Sailing & Scaling 2025, hosted by Chris Adams. It was the perfect backdrop—a breezy afternoon on the water, great conversation, and some honest reflections on the evolving state of marketing, entrepreneurship, and technology.

Joining me were Chris Adams (our moderator and skipper for the day) and Kevin Butler, Goose Digital’s Chief Strategy Officer. The three of us have spent years building businesses, navigating scale, and learning what it really means to grow something sustainable. This session was as much about reflection as it was about sharing the real, raw truths of building in today’s market.

We were also joined by Chris O’Neill (who did an excellent job as the sole camera crew!). And he brought us a fantastic lunch from a local deli!

A Decade of Goose Digital

This year marks Goose Digital’s 10-year anniversary. As I shared during the session, I founded Goose after a successful run leading a tech company in the e-commerce space. I wanted to build an agency that could help other founders and operators grow through smart, outcome-driven marketing. Not vanity metrics. Not overcomplicated tech stacks. Just intelligent marketing that drives results.

Kevin and I worked together in that past venture, and he’s been here for almost the entire Goose journey. We talked about how our origin in tech and e-commerce has given us a deep appreciation for scalability and discipline in marketing and sales. We didn’t come from the agency world—we came from building and selling both my previous companies’ tech and other challenger SaaS technology products. That lens shapes how we serve our customers.

The New Age of Intelligent Marketing

Chris asked us about how we support startups and scaleups, especially in this tight funding climate. The truth is, the bar is higher. You can’t just hire five marketers and throw $1 million at paid media anymore. The rise of AI, automation, and agile marketing has lowered the barrier to entry, but it’s also raised expectations.

We discussed our belief in intelligent marketing—our north star at GooseDigital. It’s about combining smart strategy with the latest tools (like LLMs and automation platforms) to increase speed, reduce cost, and elevate performance. That includes:

  • Training our team to augment their skills with AI
  • Helping clients embrace automation to drive scale
  • Streamlining content creation and distribution
  • Tying everything back to business objectives

Kevin emphasized how many businesses, even those doing $100M+ ARR, still struggle with sales and marketing fundamentals. And in startups, that gap is even more dangerous. Our job is to close that gap—to bring clarity and structure.

Lessons From the Helm

The sailing metaphor wasn’t just for show. Midway through the shoot, Chris led us through a tack (a coordinated sailing maneuver). It was a great analogy for business. Sometimes, when you see land coming too quickly, you have to make a decision—pivot, regroup, collaborate. Just like in business, speed and alignment are everything.

Chris talked about racing his sailboat with a team, and it reminded me how critical leadership and process are. If your team isn’t aligned, it’s not their fault—it’s yours. We can only move as fast as the system allows, and it’s up to leadership to define the system.

Sailing & Scaling

Where AI is Really Going

We spent a good portion of the conversation talking about the future of AI in marketing. Yes, it can create content. Yes, it can automate outreach. But the real transformation comes when AI becomes your strategic partner, challenging your thinking, testing your assumptions, and co-piloting creativity.

We’re already building this into how we work at Goose. And we believe our customers will increasingly judge vendors and agencies not just on output, but on how well they’re infused with AI-driven operations.

Kevin put it best: “We’re not just heading toward software-as-a-service. We’re heading toward output-as-a-service.”

Final Thoughts

Reflecting back, this wasn’t just another podcast episode. It was a reminder of how far we’ve come, as an agency, as a team, and as entrepreneurs.

To Chris Adams and the Sailing & Scaling crew—thank you for having us. To Kevin and Chris, thanks for being on this journey with me. And to every founder, marketer, or investor out there trying to scale something meaningful: keep your hand on the tiller, stay alert, and don’t be afraid to tack when you need to.

Here’s to the next 10 years!