How to Spot a Fake Expert Before They Cost You Money

William’s dad was an extraordinarily proud no-sock-wearing person. Nobody knows exactly where it started. Maybe a trip to Boston or somewhere in the Northeast for training back in the day, where he picked up the style and brought it home for good. Whatever the origin, it became his thing. There are pictures of him coaching youth soccer in shorts and loafers, no socks, pushing a puddle of water out of the goal box with a giant broom so the game could go on.

It was authentic. It was genuinely who he was.

Fast forward to a dinner out with his wife recently, where William spotted a well-dressed gentleman at the next table who appeared to be doing the same thing. No socks. A little smile, a little nod to his dad’s memory. Except a few minutes later William looked again and realized the man was, in fact, wearing socks. Hidden socks, tucked down just far enough into the shoe to create the illusion of going sockless without actually committing to it.

His dad would have been deeply disappointed.

Fashionable vs. Authentic

That small observation opened up a much bigger question. How much of what we see in the world today is people genuinely doing something versus people doing it because it looks good?

The no-sock trend is harmless enough. But the same pattern shows up in the professional world in ways that are anything but harmless. Business owners regularly end up working with attorneys, insurance agents, M&A brokers, and other advisors who present themselves as specialists in something they only dabble in. They say they do it. They have done it a handful of times. But it is not what they do every day, it is not where their real expertise lives, and the difference shows up when it matters most.

Why It’s So Hard to Spot a Fake Expert

Here is the uncomfortable truth about spotting a fake expert before they cost you money. It is genuinely difficult. When someone tells you they do something, the natural and reasonable instinct is to take them at their word. Verifying expertise takes time, effort, and sometimes a level of knowledge you don’t have yet in the area you are trying to fill.

That is exactly what makes the hidden socks analogy so useful. From a distance, hidden socks look identical to no socks. You have to look closely, more than once, before you see the difference. The same is true with professionals who look the part but aren’t actually delivering at the level they advertise.

What to Look For

The best signals of genuine expertise are the ones that are hardest to fake. How often do they actually do this specific type of work? Who else have they done it for and can you talk to those people? Do they ask the kind of questions that reveal deep familiarity with the nuances of your situation or do they stay at a surface level that could apply to anyone?

Authentic professionals are usually easy to identify once you know what you are looking for. They are specific where generalists are vague. They push back where someone trying to impress you would just agree. They tell you what they cannot do as readily as they tell you what they can.

Building the Right Team

For business owners, the advisory team around you is one of the most important assets you have. The right attorney, the right CPA, the right M&A advisor, the right wealth manager. Each one of those relationships has real consequences for the outcomes you achieve.

Don’t settle for hidden socks. Look for the real thing.

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One of the things you, as a kid, you start to learn little, little things about your parents, right? They, they know a lot about you, as you’re fairly self, uh, self-aware maybe, but, but not so much a- as aware of your parents. But one of the things I slowly recognized about my dad over time was he was an extraordinarily proud no-sock-wearing person.

So I don’t know where it came from. I think he went up to Boston or some place up in the Northeast for training back in the day, maybe saw it was a style and brought it back home. Um, I remember I’ve got a picture actually inside here of my dad. Played soccer as a kid, so my, my dad was a coach, and there was a puddle in front of the soccer goal, um, for one of our games.

And my dad’s out there in shorts, um, his loafers, no socks, and one of those big brooms trying to [00:01:00] push the water out of the puddle in front of the goal so that we could play. So standing memory, lots of pictures of me as a kid with my dad, no socks. So as a result, you certainly pick up on it becoming a trend again, right?

So you see out there today, it’s a lot more popular for, for, for folks of all ages not to, not to be wearing socks. And I was out to dinner with my wife the other night, and we were sitting next to this gentleman, and I look down and, you know, naturally I’m lo- looking at feet, and I see that he’s not wearing socks.

And so just kinda smiled and chuckled to myself. He’s an older fellow. He’s probably in his mid to late 60s or whatever, uh, well-dressed. And I look down a few minutes later and, and I noticed that he was, in point of fact, not not wearing socks. He was wearing hidden socks, and so the hidden socks sit down below the, um…

down far enough into the shoe that it looks like you’re not wearing [00:02:00] so- socks, but in point of fact, you’re wearing socks. And it kinda made me chuckle a little bit about how disappointed my dad would’ve been in it becoming a style rather than an actual thing. Um, and then it made me go back and s- you know, think a little bit more about authenticity and how there are so many people in this world today that do something because it’s in style or it’s in fashion rather than it being authentic, right?

It’s not something that they’re actually concerned with doing. They’re just making it look like it’s something that they do. And it goes back and, you know, obviously in the professional world, I always think back to the clients we work with and the professionals that they have around them and how often it is that they end up w- working with people who aren’t genuinely authentic or genuinely capable of delivering on the things that they advertise doing, right?

They don’t do it all the [00:03:00] time. They don’t do it with the clients that, you know, that we’re working with and, and, and whatnot. And so we end up with attorneys that do some work here. We end up with insurance agents that do some work there, M&A brokers that do some work there. Um, and so again, as I, you know, pull back and, and just think about it, authenticity, and it’s a very hard thing to truly understand because somebody says, “I do this,” uh, you generally want to take them at their word, right?

‘Cause it’s, it’s more difficult to not take them at their word than it is sometimes to take them at their word. So as we’re out there, you know, in the regular course of business, you know, it’s one of those things that unfortunately we always have to be on guard with is who is not wearing socks and who is fashionably pretending to not be wearing socks, and it’s the same thing in the business world.

Who can actually help you achieve the goals that you’re trying to achieve, um, versus who thinks they can do it? So anyways, [00:04:00] uh, as you’re out there on the day-to-day, don’t forget, look for authenticity. It’s hard to find. If you liked today’s video, hit the subscribe button down below, or better yet, just leave us a comment

ORIGINAL MEDIA SOURCE(S):

William Bissett: What’s Authentic About Not Wearing Socks? | Portus Perspectives

Originally Recorded on June 15, 2026

Portus Perspectives: Episode 26

By /Published On: July 11, 2026/