I first talked to Gerard Micheal back in 2023, when we discussed the Featured.com transaction and what deal structure looks like at the high end of the domain market. He was running DNPost at the time, and what stood out wasn’t the price, it was how he talked about alignment, structure, and creating value around the deal itself rather than simply facilitating it.
A lot has changed since that conversation. DNPost is now Westmore. The positioning has shifted from a transaction-based brokerage to something more like a principal investor. One that can bring capital, structure, and strategic thinking to premium transactions that go beyond a standard commission-based model. It’s a move that reflects where the most sophisticated deals in this industry are heading.
I wanted to reconnect, find out what’s changed in how Gerard thinks about the market, revisit the Featured.com deal through a new lens, and understand what the Westmore model actually looks like in practice.
Mike: Let’s start with the obvious one. DNPost is now Westmore. What’s actually different, and what’s the same?
Gerard: What’s the same is the foundation. We’re still focused on premium domain names, strategic acquisitions, and helping buyers and sellers navigate important transactions.
What’s different is the positioning. Westmore better reflects how we operate today. We’re not simply facilitating transactions anymore. We’re becoming more selective, more involved, and more focused on creating value around the deal itself. The name Westmore represents a broader vision than traditional brokerage.
Mike: You describe Westmore as operating as a principal rather than a traditional third-party broker. For people in the domain industry, what does that actually mean in practice?
Gerard: A traditional broker is primarily paid to connect buyers and sellers and negotiate a transaction.
Operating as a principal means we’re sometimes willing to bring our own capital, participate in the structure of a transaction, or help create solutions that wouldn’t exist in a standard commission-based model. Instead of simply negotiating price, we’re often helping engineer the outcome.
The goal is to align interests and create opportunities that benefit everyone involved.
Mike: When does the traditional brokerage model start to break down? Is it a price threshold, a buyer type, a deal complexity thing, or all three?
Gerard: It’s usually complexity more than price.
A straightforward six-figure transaction can be relatively simple. But when you have strategic buyers, multiple stakeholders, financing considerations, equity components, confidentiality requirements, or international parties involved, the traditional brokerage model can become limiting.
The more strategic the asset becomes, the more important deal structure becomes.
Mike: From your side of the table, what’s usually the hardest part of getting a high-value deal done? I think a lot of sellers assume it’s getting the buyer to make an offer, but I suspect it’s something else.
Gerard: Getting an offer is often the easy part.
The hard part is aligning expectations and managing risk. Buyers want certainty. Sellers want maximum value. Both sides have concerns that aren’t always visible on the surface.
Many high-value deals don’t fail because of price. They fail because of timing, trust, internal approvals, or uncertainty around the transaction itself.
Mike: When a serious company wants a specific domain, what mistakes do they typically make before they bring someone like you in?
Gerard: The biggest mistake is showing their hand too early.
Many companies approach a domain owner directly and reveal exactly how important the name is to them. That can dramatically change the negotiation dynamic.
Another common mistake is viewing the domain as a commodity rather than a strategic business asset. The best acquisitions usually happen when companies focus on long-term value instead of short-term cost.
Mike: What are the signs that a domain owner is actually willing to sell, versus just curious what someone might pay?
Gerard: Serious sellers engage in meaningful conversations.
They ask practical questions about timing, process, structure, and execution. Curious owners tend to focus only on hypothetical numbers.
The owners who are genuinely willing to sell usually understand that a successful transaction involves more than simply naming a price.
Mike: Is there a real difference between a good domain and a domain that materially changes how a company is perceived? Or is that distinction more theoretical than practical?
Gerard: There’s absolutely a difference.
A good domain is functional. A transformational domain can become part of the company’s identity.
The right domain can increase credibility, improve memorability, strengthen branding, reduce customer acquisition friction, and create a level of authority that’s difficult to replicate through marketing alone.
The best domains don’t just support a brand. They help define it.
Mike: Back to Featured.com. Two years on, how do you feel about that deal now? You told me in 2023 you thought you might’ve left money on the table.
Gerard: Every major deal teaches you something.
What I’ve come to appreciate more over time is that structure often matters more than headline price. The Featured.com transaction included a substantial upfront component, a financing element, and equity participation.
At one point I wondered whether I could have pushed harder on valuation. Today I look at it differently. The structure created opportunities that a simple cash transaction wouldn’t have provided.
Mike: A lot of domain investors still think purely in terms of buy price and sale price. Should more of us be thinking about deal structure instead?
Gerard: Absolutely.
The industry has traditionally focused on acquisition cost and exit price. But some of the most interesting transactions today involve financing, revenue participation, equity, milestone payments, or hybrid structures.
Sophisticated investors understand that value isn’t always created through price alone. Sometimes the structure is where the real upside exists.
Mike: AI has clearly moved demand for short .coms and category names. Has it changed anything else you’d point to that people aren’t talking about yet?
Gerard: One thing people aren’t talking about enough is speed.
AI companies are moving incredibly fast. Brand decisions that might have taken months are now happening in days or weeks. Because of that, premium domains are becoming even more valuable as companies look for instant credibility and market positioning.
We’re also seeing increased interest in category-defining names, not just for branding, but because they create authority in a market that’s becoming more crowded every day.
The companies that emerge as leaders will often be the ones that secure the strongest digital real estate early.
Mike: Gerard, before we wrap up, anything you’d like to leave our audience with?
Gerard: First, Mike, thank you for having me. I’ve enjoyed the conversation and the opportunity to share some of my thoughts on domains, branding, and how the market continues to evolve.
One thing I’d leave people with is this: premium domains are no longer just internet addresses. They’re strategic business assets. The right domain can influence perception, accelerate trust, strengthen a brand, and create opportunities that extend far beyond the initial acquisition.
Whether you’re a founder building the next great company, an investor evaluating digital assets, or an established business considering a rebrand, it’s worth taking a serious look at the role your domain plays in your long-term strategy.
You can learn more about what we’re doing at Westmore.com. I also publish a LinkedIn newsletter — the Digital Asset Strategic Brief — where I share insights on premium domains, branding, and developments shaping the industry. I’d love to have your readers subscribe and connect with me on LinkedIn.