Final week, I had the prospect to step off dry land and onto Lake Simcoe for a particular version of Sailing & Scaling 2025, hosted by Chris Adams. It was the right backdrop—a breezy afternoon on the water, nice dialog, and a few trustworthy reflections on the evolving state of selling, entrepreneurship, and expertise.
Becoming a member of me had been Chris Adams (our moderator and skipper for the day) and Kevin Butler, Goose Digital’s Chief Technique Officer. The three of us have spent years constructing companies, navigating scale, and studying what it actually means to develop one thing sustainable. This session was as a lot about reflection because it was about sharing the actual, uncooked truths of constructing in right this moment’s market.
We had been additionally joined by Chris O’Neill (who did a superb job as the only real digital camera crew!). And he introduced us a implausible lunch from a neighborhood deli!
A Decade of Goose Digital
This yr marks Goose Digital’s 10-year anniversary. As I shared in the course of the session, I based Goose after a profitable run main a tech firm within the e-commerce area. I needed to construct an company that might assist different founders and operators develop by means of good, outcome-driven advertising. Not vainness metrics. Not overcomplicated tech stacks. Simply clever advertising that drives outcomes.
Kevin and I labored collectively in that previous enterprise, and he’s been right here for nearly your entire Goose journey. We talked about how our origin in tech and e-commerce has given us a deep appreciation for scalability and self-discipline in advertising and gross sales. We didn’t come from the company world—we got here from constructing and promoting each my earlier firms’ tech and different challenger SaaS expertise merchandise. That lens shapes how we serve our clients.
The New Age of Clever Advertising
Chris requested us about how we help startups and scaleups, particularly on this tight funding local weather. The reality is, the bar is greater. You may’t simply rent 5 entrepreneurs and throw $1 million at paid media anymore. The rise of AI, automation, and agile advertising has lowered the barrier to entry, but it surely’s additionally raised expectations.
We mentioned our perception in clever advertising—our north star at GooseDigital. It’s about combining good technique with the newest instruments (like LLMs and automation platforms) to extend pace, cut back value, and elevate efficiency. That features:
- Coaching our crew to reinforce their abilities with AI
- Serving to shoppers embrace automation to drive scale
- Streamlining content material creation and distribution
- Tying every part again to enterprise targets
Kevin emphasised what number of companies, even these doing $100M+ ARR, nonetheless wrestle with gross sales and advertising fundamentals. And in startups, that hole is much more harmful. Our job is to shut that hole—to deliver readability and construction.
Classes From the Helm
The crusing metaphor wasn’t only for present. Halfway by means of the shoot, Chris led us by means of a tack (a coordinated crusing maneuver). It was an amazing analogy for enterprise. Generally, once you see land coming too shortly, you must decide—pivot, regroup, collaborate. Identical to in enterprise, pace and alignment are every part.
Chris talked about racing his sailboat with a crew, and it jogged my memory how essential management and course of are. In case your crew isn’t aligned, it’s not their fault—it’s yours. We will solely transfer as quick because the system permits, and it’s as much as management to outline the system.
The place AI is Actually Going
We spent portion of the dialog speaking about the way forward for AI in advertising. Sure, it may well create content material. Sure, it may well automate outreach. However the actual transformation comes when AI turns into your strategic accomplice, difficult your pondering, testing your assumptions, and co-piloting creativity.
We’re already constructing this into how we work at Goose. And we imagine our clients will more and more choose distributors and businesses not simply on output, however on how effectively they’re infused with AI-driven operations.
Kevin put it greatest: “We’re not simply heading towards software-as-a-service. We’re heading towards output-as-a-service.”
Ultimate Ideas
Reflecting again, this wasn’t simply one other podcast episode. It was a reminder of how far we’ve come, as an company, as a crew, and as entrepreneurs.
To Chris Adams and the Crusing & Scaling crew—thanks for having us. To Kevin and Chris, thanks for being on this journey with me. And to each founder, marketer, or investor on the market attempting to scale one thing significant: maintain your hand on the tiller, keep alert, and don’t be afraid to tack when you must.
Right here’s to the subsequent 10 years!
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