Former commercial litigator turned e-commerce founder Greg Shugar joins the show to unpack his journey away from the soul-crushing legal grind. Following Larry’s opening take on the danger of default career paths, Greg shares how a messy breakfast spill sparked a multi-million-dollar fashion empire and why buying an existing business is the smartest play you can make in the 2026 economy.

If you are trapped in a career you absolutely despise, it is time to map out your exit strategy. In this episode, Greg Shugarshares the raw, unfiltered truth about leaving the legal litigation grind to build real-world wealth on his own terms. What started as a moment of pure frustration over a ruined $70 silk tie turned into a garage-based startup that exploded overnight.
By tracking down international suppliers on Alibaba, Greg discovered that high-end ties only cost $2.10 to manufacture. A massive feature in the Chicago Tribune blew the doors off the operation, allowing him to escape a professional landscape defined by constant negativity, bitter disputes, and rigid corporate structures.
Fast forward to the 2026 economy, and the traditional startup playbook has completely changed. Greg explains why launching a brand from scratch is now a massive gamble and breaks down a safer, highly lucrative alternative: acquiring established, cash-flowing small businesses from retiring baby boomers. We also dive into the operational habits of successful CEOs, the danger of defensive founder egos, and how AI Engine Optimization (AEO) is forcing modern consumer brands to completely reinvent their digital marketing.
What We Cover:
Escaping the Legal Grind: Why the relentless friction of litigation pushes professionals into depression, and how reviewing everyday blue-collar client financials inspired Greg’s exit.
The Side Hustle Launchpad: How to leverage your full-time corporate salary to fund early product development before taking the financial leap.
The Problem with Franchises: Why forced marketing rules, rigid playbooks, and royalty fees make franchising a nightmare for creative founders.
The Humility Metric: Why checking your ego and listening to brutal customer feedback is a non-negotiable hard skill for any CEO.
Acquisition vs. Startups: Why buying a profitable, existing service trade (like plumbing or HVAC) is far cheaper and safer than building an e-commerce brand today.
The Rise of AEO: How conversational AI prompts are replacing short keywords, rendering traditional SEO models obsolete.
The Automated Studio: How off-the-shelf AI tools are completely disrupting commercial product photography roles.
Lary Port (00:00):
Dream Job or Nightmare. It’s hard to know if a career that looks great on paper will actually lead you to the life you want to live. So welcome to Dream Job Cafe. I’m Larry Port. I’ll be asking different professionals the questions you won’t find anywhere else. So grab a coffee, settle in. This is Dream Job Cafe. Sponsored by wastepark.co, where we help people navigate careers in a crazy world. Hey everybody, and welcome to another episode of Dream Job Cafe. We are going to continue with our entrepreneurship series and I’m so grateful to have my friend and neighbor Greg Shugar with us today. Hey, Greg. Hi
Greg Shugar (00:40):
Larry. Thanks for inviting me.
Lary Port (00:41):
Yeah, so Greg does a lot. He is the owner and CEO of Beau Ties of Vermont. I believe it’s his second or third business that’s in the fashion business. And he’s an investor, he’s been an attorney. He used to write a column for Entrepreneur Magazine, so he’s done a lot. So Greg, we’re very excited to have you here. Let me start by asking you this. Tell me a little bit about I guess your journey because you’re an entrepreneur now, you’re running Beau Ties of Vermont. By the way, for those keeping score at home, that’s spelled B-E-A-U Ties of Vermont. You began your career as an attorney, if I’m not mistaken. I don’t know if you did something before that and then you transitioned to entrepreneurship. So can you talk a little bit about that?
Greg Shugar (01:34):
Yeah. I mean, if you go way back, I actually majored in TV production and worked for the Atlanta Journal Constitution’s advertising department before law school. So I really never expected the path I was on. But yes, I went to law school and practiced law for about eight and a half years. And towards the end is when I started a business on the side. It was an experience I had where I was wearing a tie every day. My then three-year-old son threw some cereal on my tie. I got very frustrated. I just bought the tie. I just spent $70 on the tie and I though, why is this thing $70? I went online just that morning and found a website very few people had heard of. It’s called Alibaba, which of course now everybody knows Alibaba. And I found a bunch of factories in China and I just was more curious about how much I was getting ripped off in the tie world and found out that silk woven ties made in China were $2.10.
(02:31):
Now this was 2004, but I still felt like that’s a pretty damn good margin.
Lary Port (02:37):
That is a good margin.
Greg Shugar (02:38):
Yeah, right? So I just started poking around asking questions and my then wife and I were talking about how I pay so much for ties, everyone does. Should we? D we have to? And I don’t know. Within six months, we had come up with this idea of selling silk ties for $15. We had this idea of just doing it on the internet, which again, back then was a little bit strange. I had no design background. I had no business background. And we had the website done, the inventory made, sitting in my garage, moved it into my basement all in a period of six months and launched this company. And basically over a period of a year, it went from $0 in revenue to I think we did maybe a hundred thousand in sales in the first 12 months. But we then got this really great PR piece in the Chicago Tribune’s Sunday style section.
(03:39):
And back then people read newspapers and they definitely read the Sunday paper. And it just blew the company up and it became like an overnight boom for us. And the day before the paper came out, we did nine orders. The day that the article came out, we did 206 orders. So it completely changed the dynamic of our company overnight. After 30 days of some steady sales, I sort of reassessed my life, realized how much I hated being a lawyer and decided to quit practicing law and run the company full-time altogether. So there was about a 14-month overlap where I was a lawyer by day and e-commerce tie guy by night.
Lary Port (04:22):
Yeah, that must have been a tough grind because when I started my business, I was working full-time and it was three months and it was pretty exhausting. That’s kind of what I remember from that time period. It
Greg Shugar (04:34):
Was totally exhausting. My then wife was extremely helpful and instrumental, especially during early on. We had two little kids, so certainly that was a lot of work too. But I was also 31 years old and I had all the energy in the world. And I think what also motivated me is I just hated being a lawyer. And I think I was finding that I might have a way out of this thing finally. It was like that moment in Shashank Redemption where you find the hole in the wall. I just feel like I found the hole and the wall and I was ready to escape.
Lary Port (05:05):
It’s funny that you mentioned that you did not enjoy being a lawyer because when I worked with lawyers, we did a content piece about this issue and there’s a very high percentage of lawyers that suffer from alcoholism that are depressed. Some people truly find it to be their calling, but why do you think this is? Is this one of these default careers that people stumble into? Why do people become lawyers if they’re going to be unhappy?
Greg Shugar (05:31):
There were a lot of law students who went to law school because they didn’t know what else to do. That’s a real thing. I don’t know if it still is, it certainly was back then. It’s a good living. It’s not a great living. Obviously there are some exceptions or are lawyers making tons of money,
(05:47):
But the average lawyer makes a good living, not a great living. And it’s hard to make a good living. So when you’re like, “Hey, I found a way to make a good living,” you jump on it. The problem is it’s a grind. It never ends no matter how old you are. And I was in litigation and litigation is contentious. There’s a winner, there’s a loser. Your clients are never happy. Judges are assholes. The other attorney is definite dipshit. And so it’s like you never escape negativity and it really never ends. And so I hated every second of it if you can’t tell.
Lary Port (06:22):
Wow. Well, no, the sad part for me is that I think there’s a lot of people that are in this boat. So anybody out there who’s thinking of law school as a kind of default option, I’m not sure what else to do. I don’t know. I would maybe talk to a couple of lawyers before you jump into it because as we mentioned before, there’s a lot of unhappy people doing it. Let me ask you this though. Accountants have this ability to understand business because they see it so close up and they see so many different types close up. As a litigator, a commercial litigator, did that give you any kind of understanding of business that helped you when you went out and started on your own?
Greg Shugar (07:08):
They were definitely an inspiration because I just remember representing small business owners making a lot of money. Because depending on the lawsuit, we would have to typically know what their revenue and their margins were to help determine what the damages are and so forth. And I used to see numbers and I’m like, “This is crazy.” My best year as a lawyer made 106,000 a year. I remember representing a siding company and the guy just sold siding door to door, aluminum siding for homes. And he made 700,000 in revenue. Sounds like nothing. It doesn’t even sound like a business. He brought home 400,000 a year, and this is 2002. So I’m thinking, oh my God, a guy’s making 400 grand a year. Drives off in his Escalade. I’m parked next to him in my Honda Civic with no air conditioning. I’m like, “What am I doing wrong?” And I was so inspired by all these small business owners.
(08:01):
I represented a guy who was literally illiterate. I wrote an affidavit for him and he told me he couldn’t read it because he doesn’t know how to read. Really?
Lary Port (08:11):
And he was
Greg Shugar (08:11):
Doing almost $30 million in sales in his business and his EBITDA was over five million. And so I don’t know if it was that I learned business, but I definitely learned that if you just take the leap and you go for it, that’s basically the only way it’s ever going to happen. You can’t just sit on your hands. But I just felt like there were people less capable than me, even though that may have not been true. I certainly thought it. There were people less capable than me that were earning much better livings and maybe this is the path for me. Also as a lawyer, I was actually only in hindsight I realized this, I was quite entrepreneurial. I had a book of business early on. I had my own clients and it mattered to me. I worked hard at getting my own clients. That was something I was trying to do, not even realizing that that was an entrepreneurial thing to do.
(08:59):
I just, for whatever reason, I was gravitating towards the idea of trying to build my own book of business. It seems obvious why I would, but at the time it didn’t really feel that way. I just kind of wanted to keep myself busy and that was my way of doing it.
Lary Port (09:13):
Wow, interesting. Well, on the business front, because I think a lot of entrepreneurs have their different strengths and weaknesses. I mean, you have a great personality. You’re very funny on LinkedIn, by the way. If any of you are on LinkedIn and want to see how to use it or how not to use it, maybe follow Greg. But a lot of entrepreneurs, they kind of fall into different buckets. Some are more marketing oriented, some are more operational oriented, some are technologists like me. You mentioned before that you made a lot of rein as a lawyer. Would you say that your strength as a CEO was more on bringing in business or was it in operations? Cause there’s also these different aspects of it. What kind of CEO were you?
Greg Shugar (09:58):
I’ve always been, well, I mean, I think my strengths, let’s say, hard skills are more marketing and branding and product because the truth is they all work together. And I do see a lot of entrepreneurs make the mistake not understanding that a lot of the best marketing comes from understanding your product extremely well. But those are my strengths, marketing, branding, product side. But having said that, you have to be competent in everything. I would say my best soft skill is I’m a problem sover. When something goes wrong in our company, I just try to first figure out how to fix the problem right away. And then I try to come up with a system to make sure it never happens again. And you tend to find certain people who might spot the problem but have no solutions on solving it. And so I’d say probably my greatest strength as a owner or CEO is I see an opportunity, I go for it.
(10:54):
I see a problem, I fix it. I just don’t stand still. I don’t kick the can. The moment an idea hits me, I implement it and I try a lot of shit. A lot of stuff doesn’t work, but I’ll try anything that sounds right, I just give it a shot. So I don’t know if I, I do a lot of things, I guess, but I hate financials. Operations bores the hell out of me. I can do it. But again, I think as a CEO or an owner of a small business, you have to learn everything. You have to be a jack of all trades.
Lary Port (11:25):
Yeah. And unappetizing as that may sound for some people, it’s less so when it’s your thing. I’m kind of like you. I don’t know if you knew this, but I actually was a film and television undergraduate major. Oh, really? Did you know that?
Greg Shugar (11:40):
Okay.
Lary Port (11:41):
Yeah. And I was interested in documentary production for a while and hated it before I shifted into computer science. But my point is that like you, I wasn’t really into… I think I had never read a financial statement before. Because it’s your baby, you kind of get used to it so it makes it a lot easier to go down. Let me ask you this. A lot of people are very concerned about entrepreneurship because they think it’s risky. I have my own personal opinions about it. I’m curious what you have to say about that.
Greg Shugar (12:13):
I mean, I suppose it all depends on what you’re doing and when you do it and things like that. I mean, first of all, it’s not meant to be completely risky. You’re supposed to be taking calculated risks. I think you can try doing certain things where you try starting a business while you still have a full-time job, still collecting a paycheck and you try to do it at night the way I did it. I don’t think that’s a long-term plan. It’s a good way to get off the ground. I think it’s risky if you’re like, well, okay, I’m walking away from my job and I’m starting a business from scratch. That’s risky. There’s a lot of work you could be doing before you walk away from your job. And I think actually the best way to get into entrepreneurship right now in 2026 is through acquisition.
(12:58):
I think that there are so many… It’s much harder to start a business from scratch and to just buy a revenue-making, profit of making company. And the money you put in to start a business from scratch is more than likely going to cost more than the acquisition of an existing company. I am convinced of that. There are obvious exceptions, but generally speaking, I think that’s a much greater path and far less risky path into entrepreneurship right now.
Lary Port (13:26):
So you’re saying find a business that’s for sale, whether it’s a pizzeria, a coffee shop or whatever, and instead of opening it on your own, find a broker or some sort of person who can make this deal happen. And what about the capital side of that? Because if somebody’s doing a mid-career switch or they don’t have the savings for it, what would you recommend then? Investors, loans, that kind of thing?
Greg Shugar (13:51):
Well, I mean, just to start, you don’t necessarily find the pizzeria and say, let me go buy it. There’s listing services. There’s plenty of business broker listing services online. There’s so many of them right now. So finding a business for sale is not necessarily difficult. Sorry, what was the second part of your question? Oh, the money, the financial side. Yeah, that could be trickier. If you don’t have money, there’s options. SBA loans is an option. Some are more likely to qualify for an SBA loan from the government than others. There’s certainly seller financing is an option. There can be an earnout provision as well. Going to friends and family, I personally don’t love at least the friends part. The family part maybe. I think going to friends more of a social discussion, but I don’t think going to friends is the right move. So there are options.
(14:43):
But if you’re like, “Hey, I was going to do a startup anyway,” well, you’re still having the same conversations. Where am I going to get the money? Startups aren’t free. So you have the same conversations around where am I going to get the money, whether it be a startup or an acquisition. But there are so many types of businesses for sale. I mean, this conversation that’s been going on for a few years now. There’s this baby boomer generation who are owners of businesses whose second generation kids are not interested in becoming a part of it. They have presumably not exercised a lot of creativity or aggressive marketing. And so they’re leaving opportunities on the table that they’ve never even tried. And the theory goes that a younger, hungrier entrepreneur can come in and turn it into something far more lucrative than the previous owner. You see it a lot in what we, I don’t know, recession-proof, AI proof businesses, service businesses.
(15:33):
So plumbing, lawn service, HVAC. They’re some of the highest trade businesses, traded businesses, meaning the multiples on their EBITDA is super high right now because they’re super hot. There appears to be so much opportunity on the acquisition side, meaning that there’s so much more money to be made that the multiples are higher. But the point being that there’s so many of these types of businesses for sale. There’s plenty of e-commerce businesses for sale, which is my world, but the e-commerce world is a shitty and challenging one right now and not one I really recommend. It’s probably the riskiest business to try to get into right now. But I guess what I’m just trying to say is it’s not hard to find a business for sale.
Lary Port (16:18):
It’s kind of interesting. So for anybody who’s listened to this podcast before, Greg, you just mentioned two things that are trends that we talk about quite a bit. One is the notion of the aging population and that’s where you have all these baby boomers who in some cases it’s detrimental. They’re kind of clogging up the top at corporations so people can’t advance, but they are retiring in droves. And number two is what that’s doing to the skilled trades. Because as these people move out of the labor force, there’s just not enough people to fix your shit. And this is a problem that’s happening all across the country. So these are two ways in which you kind of touched on those issues. Let me ask another question for you. What about franchising? It used to be when I thought of a franchise, I though of Kentucky Fried Chicken.
(17:10):
Now people have franchises where they walk dogs.
Greg Shugar (17:13):
Yeah. I’m the wrong guy to advocate for franchises. I think they are by far the worst business idea, especially with anybody that has entrepreneurial leanings because of all the handcuffs they put on you. You have to do it this way. You have to sell this. You have to do it for this price. You can’t do your own marketing. There’s so many rules in place for these franchises. It makes sense why the rules exist, but if you have any sort of entrepreneurial or creative leanings, franchise is not the way to go. Not to mention, of course, you’re giving away a certain amount of your revenue to the franchisor. But I mean, you talk about dog walking is a great example. Why would I need a franchise to open up my own dog walking company? You might say, well, it’s for the goodwill. It’s for the name of the business.
(18:07):
It’s an easier sell to somebody who might be familiar with the name. I mean, I think franchises make the most sense with Kentucky Fried Chicken with a really strong franchise, but all this other stuff, just do it yourself. You’re more than likely franchising a name that very few people know and whatever operations or systems they already have in place that they supposedly hand to you so you don’t have to do the work, it’s not going to be rocket science. I think franchising is by far the worst way to get into entrepreneurship. I hate it. So I’m sure people love it though.
Lary Port (18:39):
Especially if you are more on the creative side, like an entrepreneur like you or me. If you’re more into the maybe spreadsheet side of things, I could see how it might be more appealing. But even then I hear what you’re saying. Unless it’s a nationally recognized brand, why even bother?
Greg Shugar (18:57):
Right. And then if you want to own 20 Dunkin Donuts, I mean that’s a great way to make a real living. Owning one is not, owning 20 is. That’s a pure… Again, if you’re entrepreneurial and to your point, creative, it’s not the path. Yeah, if it’s not a big brand name, I don’t see the point at all.
Lary Port (19:16):
Interesting. Now let me ask you this. Obviously one of the beautiful things about entrepreneurship is that the spoils can be great. You can end up doing really well in entrepreneurship, but it does require, in my opinion, a certain personality type. In your opinion, what skills or traits would lend somebody to be a good entrepreneur and who should maybe run screaming in the opposite direction?
Greg Shugar (19:49):
I mean, who’s the type? You have to have the type A personality. You have to be the person that just… I don’t know. I’m going back to something I already said, which is you have to be a problem solver. You have to be the person that wants to fix the existing problem, make sure it doesn’t happen again. You just have to be completely obsessed with your business. Working hard is, in my opinion, no longer a prerequisite for… I mean, it is a prerequisite for being an entrepreneur, but it’s not nearly enough. You have to obsess over your business and you have to be willing to do everything. And people say you got to clean the bathrooms. I mean, I literally had at one point clean the bathrooms. You have to just be willing to do everything. My first business every weekend during Christmastime, I would go in Saturday and Sunday and print and pack all the orders myself.
(20:43):
I was the only one in there quiet, completely quiet, and I would just pick and pack orders all weekend just so we can get a head start on Monday. You have to be willing to do anything and everything. And if that’s not your personality type, if you’re like, “Well, I’m a specialist or I’m too good for something,” it is not for you. And you have to be willing to have a lot of bad days. That’s the problem with entrepreneurship is there’s not a lot of… Certainly early on, it’s really hard to get winning days. And you have to find a way to get through those days where you don’t get a lot in sales or something’s horribly wrong, your internet’s down for three days. You have to have the thick skin to get through that. And then of course, to come up with the solution of those problems.
(21:26):
What am I going to do to stimulate sales again? What am I going to do? Okay, we’re out of… I mean, this just happened. Our internet went down. We couldn’t print orders that had to go out FedEx that day. They had to. So my solution of course was run down to the FedEx place, grab the sheets that you literally hand write on the shipping labels and ship these things manually. And we’ll deal with tomorrow contacting the customers and letting them know that everything’s shipped and here’s a tracking number.You have to be willing to just… You have to come up with everything and anything right away.
Lary Port (22:02):
Yeah. I used to think it was like a rollercoaster because you’d have some days where you’d land your biggest account and those were amazing days and you felt incredible. And then you’d have other days where you’d lose your biggest account and you felt miserable and it was scary. One time somebody came to me that was working for my staff and he was starting a business and he was going through a recovery for a pretty nasty addiction. And I was like, “Are you sure this is the right idea?” For him, that level of volatility did not end well for him. But I think for the most part, it is possible for people to do it. I don’t know if you felt this way, but for me, one of the things where I knew I was kind of onto something or I felt that it was obvious that my idea would work.
(22:51):
And it didn’t matter what people said to me, I was like, “They don’t see it. They don’t get it. ” And you see it sometimes when they interview people in Shark Tank after the people reject them. They’re like, “Yeah, I don’t know what they’re thinking. They’re wrong.” You’re just so convinced that it’s going to work. If you don’t have that level of conviction, I think, then maybe it’s not the right play.
Greg Shugar (23:14):
Yeah. You know what I have not mentioned, I should, and I always preach this, so I’m sorry I forgot, is entrepreneurs need to have humility. They need to realize that they don’t have all the answers, that sometimes your customers are actually correct in their criticisms of your product. You have to realize when your marketing campaigns are not working. You have to just realize you may have not created the greatest thing in the world, whether it’s the product itself or the operating system in the back or some technology you’ve added to your site. You need humility. And I have met with way too many startups who come to me asking for advice and when I start giving it to them, they get defensive and they almost get angry with me and they defend what they’re doing even though what they’re doing is clearly not working. And I just think that humility is the most overlooked quality you need to have as an entrepreneur.
(24:08):
And I really do talk about this all the time. I can’t even begin to tell you how many companies I have seen that are just not working and I’ve been asked to give my input. I give my input and the entrepreneur gets angry with me. I’m like, you’ve got problems. They are convinced that it’s you, the customer who just doesn’t get it.
Lary Port (24:28):
Interesting. That’s
Greg Shugar (24:29):
Not how to think of a company. In my world of, let’s say, consumer goods, you see that with people. And I thought you were going with that on Shark Tank because there are people who walk out of Shark Tank after not getting a deal saying, “These guys are idiots and I can’t believe they didn’t see how great my product is or my company is. ” Or they asked for these ridiculous valuations and that comes from a ridiculous sense of importance or success that their company doesn’t have. Have a little humility that your company is not as grandiose as you might think.
Lary Port (25:01):
Yes, that I do agree with. I think the most important thing that you said there is you definitely have to think that what you’re onto is hot shit, but you have to be able to admit when you’re wrong. And a lot of people can’t hear those words that you’re just incorrect about this. And nowadays it’s like, all right, there’s usually data for every decision you’re making. So if you’re staring something in the face, you have to honor that. But for me, I think some of that was tempered by the fact that I was a technologist and I was used to being when I was right, I knew I was right. And when I was wrong, it was very obvious when I was wrong. So you kind of do have to have that. And also the ability to course correct. What about working with other people?
(25:55):
There’s no way to grow a business without getting around the people around you to grow and hiring people and bringing people in. Is that something that you enjoy doing or how did you approach that? Because I was not that good at that.
Greg Shugar (26:16):
I was about to say I’m the wrong guy. I suck at that. I got to tell you, I’m the worst at delegating and enabling people or helping them grow. I do my best. I know what I’m supposed to do, so when I’m paying attention, I’ll do those things. But I am just such a fuck it, I’ll do it type of guy. And I just suck at it. I happen to have great people who work for me now and I have done a much better job with this company than my other companies in leaning on the people who know how to do things for me. And I have a person who works for me, I call her my chief of staff, and she’s so good at doing so many of the things I just don’t want to do. And she’s extremely detail-oriented. And I think when you’re an entrepreneur, you’re usually scatterbrained and you’re all over the place.
(27:10):
You can’t possibly remember everything because you have so many irons in the fire going. And so it’s so good to have somebody to keep track of all that and to be detail oriented when you overlook things. And she’s that person for me and I think she’s been a huge part of my success. And likewise, we’re a manufacturer of our own brand. And so I have a couple production managers in Vermont where our company is, and they do just an outstanding job of managing the cutting and the sewing and of course the production of all of our products. And I couldn’t possibly have done it without them. It helps that they’re in Vermont. If I lived in Vermont or if the factory were here in Florida, who knows how much I would have destroyed that operation that they’ve created. But because I’m not there, they do a really good job.
(27:59):
But yes, I mean everyone I’ve ever heard that’s far more successful than me talks about the importance of hiring the right people and empowering them and having them take on more responsibility and grow and all that. I’m sure that’s all true, but I’m the wrong person to give a testimonial on it. All
Lary Port (28:18):
Right. So Greg, you’re a big advocate for entrepreneurship. What about for the people out there that just don’t want it? What kind of words of advice might you have for them in terms of finding a fruitful career or something like that?
Greg Shugar (28:34):
I’m terrible at that too. I don’t know how to tell somebody I have a fruitful career. I sucked working for other people, so I can’t answer that. But you did send me some pre-questions related to AI that I’m happy to talk about, or am I not the AI guy for you?
Lary Port (28:49):
No, I want to hear about how it’s affecting everybody in every industry because it’s affecting… You don’t have to work for a consulting company to be interested in AI. It could be anywhere. So Greg, what are your thoughts about how AI is affecting your industry, your thoughts about it in general?
Greg Shugar (29:07):
AI has played a huge role in e-commerce. You can’t go to a conference now that doesn’t have AI as pretty much the only topic we’re talking about in some ways. I mean, all the conversations around merchandising and inventory control have gone to the wayside. All we do is talk about AI. There’s a lot of technology that is out there for websites. Some is okay, and I would say most is not. The most common place you see it is in chatbots. I’m sure you’ve had experience as customers talking to a chatbot –
Lary Port (29:39):
Today?
Greg Shugar (29:40):
Yeah. And how’d it go?
Lary Port (29:42):
Oh, I wanted to kill the people.
Greg Shugar (29:45):
Yes, exactly. So the best AI I’ve found in terms of chatbots are probably built in – house by big companies with big budgets. But the off-the-shelfs technology for companies like me, they’re just not there yet in my opinion. There’s also AI Pay for things like inventory control. Shopify has its own AI, a native AI thing called Sidekick. I don’t know if you’ve heard of it. It’s within Shopify. It basically has helped you instead of pulling reports, you just tell it what kind of report you want and it creates it for you. So it’s just made things a little bit easier. I don’t know how helpful it is in terms of making suggestion. I know there’s all this talk about creating agentic AI and I’m nowhere, that’s not me either. I’m trying to just get off the ground and save some work. I still believe that human decision making is better.
(30:40):
I think AI is good for executive assistant type of things or just summarize something or write something that I don’t feel like writing. So I don’t think it should do all your writing. There’s some emails that we write to our customers, email campaigns that I purposely write because I think my voice is a fairly unique one and I frankly enjoy writing and I don’t want someone to take that away from me. And I’ve played with it trying to understand my voice and it does a caricature of me and it’s like trying too hard to be me. I’m like, “That’s not me. I’m much cooler than that. ” So anyway, AI is all over in e-commerce and it’s just not there yet. We’re all spending a lot of money in it. But again, at least as far as off-the-shelf technology, I don’t think it’s great. I will say one thing though where it’s been unbelievable in e-commerce, it’s photography.
(31:38):
And I hate to say it because we have a great photographer that we work with and I still hire and I’m very happy to use, but there are tasks that we are able to now use through AI and I don’t even use them all even though I know how to and I know where they exist. But the ability to capture product photography through AI is phenomenal. You don’t need a professional photographer to take
Lary Port (32:00):
Product
Greg Shugar (32:00):
Photos anymore. The truth is those people, if they’re not currently out of a job, they will be very soon.
Lary Port (32:07):
Oh, that’s tough to hear. What about how Google now jumps in front of the search results page? That has to be affecting e-commerce.
Greg Shugar (32:15):
Yeah, I mean there’s this whole world. So we all know what SEO is, of course, search engine optimization. Yeah, that’s where I was going.
(32:20):
Yeah. And there’s this term now you may have heard called AEO, which is basically AI engine optimization, whatever. They just call it AEO. So it’s how do you appear in AI answers to questions into responses to prompts? And so everybody’s trying to figure out the puzzle of how do you end up in the suggestions of either Gemini when they summarize at the top what are the best Beau tie companies or of course Claude and OpenAI or ChatGPT. So everyone’s still trying to figure that out. It’s a little bit of a mystery. There are companies that are coming up with attribution models to help show you when it is and isn’t working. The problem is in the old days with search, it’s so easy. You just type in Beau ties. That’s how you’d find your Beau tie companies. Or you want to shop shoes, you used to just type shoes.
(33:10):
Everybody now is typing in prompts. They’re typing in long sentences. So it’s really hard to figure out where you are in terms of success of showing up in answers to OpenAI because people don’t go into ChatGPT and type in Beau ties. They say, “Where would I find the best Beau tie in Boca Raton? It’s got to be green with the blue stripe.” Everything is so much more, I forget the term, there’s a term, but long-winded. And so it’s really hard to figure out where you are in the AI world. So the best thing you can do is get one of these attribution software and se what kind of traffic you’re generating from these AI models. And that includes Google. But right now, I don’t think Google really differentiates between what’s coming from Gemini click and what’s coming from a sponsored click.
Lary Port (33:53):
Interesting. Very interesting stuff. So obviously when you become an entrepreneur, you have to go deep into things like this, as did I. However, it was a different era. It was the search era. And so Greg, I guess one last thing as I might observe is that you got to be a lifelong learner and you got to like to learn if you want to be an entrepreneur. Agree, disagree?
Greg Shugar (34:14):
Yeah, totally. I mean, people are like, “How long have you been doing e-commerce?” I’m like, “22 years, but if you’ve been doing this two years, you have the same experience as I do in e-commerce. Maybe not in running a business and all those other things, managing people. But you put someone who’s been this two years and they could more than likely run circles around me because at this stage of my life, I’m a little bit more part-time, a little bit more laid back. But if you’re really into e-commerce right now and it’s like your life and you’re doing it 80 hours a week, you could become an expert real fast. So yeah, to be me, I’m in a group of e-commerce owners, an online forum, and I listen most of the time. I am not there to give anybody advice. I take advice from everyone else because they know their shit far better than I do.
Lary Port (35:01):
All right. Greg Shugar. Hey, thank you very much for being on the program.
Greg Shugar (35:06):
Yep. Thanks for having me.
Lary Port (35:08):
Folks, if you like this podcast, please like it. Tell your friends about it. And if you can, be grateful for something today. Thanks for listening. Don’t forget to like and subscribe to Dream Job Cafe on Spotify, Apple Podcasts, or wherever you listen. And don’t forget to check out wastespark.co, where we help people navigate careers in a crazy world.
Greg Shugar is a former commercial litigator who successfully transitioned into an e-commerce innovator and angel investor. He has founded multiple multi-million-dollar consumer brands and currently runs operations for Beau Ties of Vermont.