Unhidden: Sleeping Well At Night – A Conversation With Josh MacDuff

Kathryn Blume 30 May 2019

Recently, we were contacted by an insurance agent named Josh MacDuff who told us that he was very interested in becoming a Heady Vermont business partner in large part because the primary focus of his work is insuring farmers and other agricultural business owners and that he has a particular passion for figuring out ways to serve Vermont’s new but rapidly growing cannabis industry.

When we finally sat down to chat with Josh, it also turned out that he has a very personal history with cannabis on both sides of the law, and that that experience has profoundly impacted both his life and his career choices.

Listen to the conversation with Josh here, or read the transcript below.

Josh MacDuff: Yes, I’m Josh MacDuff. I work for Kinney Pike Insurance. We’re based over in Rutland, Vermont.

Kathryn Blume: What’s your personal background with cannabis?

Josh MacDuff: I’ve got a long history from a recreational standpoint. I went to Green Mountain College. While I was there, I was put through the system for selling cannabis.

Kathryn Blume: When you say put through the system, you mean you got busted?

Josh MacDuff: I got busted—

Kathryn Blume: And you ended up in jail.

Josh MacDuff: Not so much jail. The reason I avoided jail was to— I dangled a carrot in front of them that I would flip on the people who were higher up than I, but obviously—

Kathryn Blume: Was that a dangerous choice for you to make?

Josh MacDuff: Yeah, I mean it was a dangerous choice, but I had no intention of ever doing it, and I never did. But yeah, so they put me through the system. Shortly after that, I was out of school because of my choices there, and spent four years while on probation working in a state quarry and going to classes at night to get my associate’s degree. After the four years of probation as part of my plea deal, they expunge my record and therefore, I was effectively never in the system to begin with.

Kathryn Blume: Clearly, this is something that you’re willing to share with people is an issue for you in your current job situation?

Josh MacDuff: I don’t have a record. I don’t have to answer certain questions on an application. But I’ve always found in what I do, and what makes me kind of the person that I am, is to be transparent. And it’s one of those things where I might anger some clients, or maybe deter clients from doing business with me if they ever find out that I have a history with cannabis. And I guess in theory, there was a window where I was a convicted felon but it doesn’t make me any less of a person. So I’m comfortable sharing my story with anybody who wants to hear it.

Kathryn Blume: How did you get busted in the first place?

Josh MacDuff: [Laughs]. I’ve changed over the years, but I guess I would say I wasn’t a savvy businessman. I became the guy who sold to the locals. As the guy selling to the locals, there were a lot of strange unknown faces showing up in my dorm room at various hours of the day and—

Kathryn Blume: So, you were living on campus?

Josh MacDuff: I was living on campus, yes.

Kathryn Blume: And your friends were streaming and out and they were not known to the college community?

Josh MacDuff: Correct. In a small town going to Green Mountain College which (God rest its soul) is no longer in abundance where it’s a small town. And I think the school officials can kind of keep a better track on who’s visiting the campus and who isn’t.

Kathryn Blume: You’re a young well-educated white guy.

Josh MacDuff: [Laughs].

Kathryn Blume: So, how is it for you getting caught up in a system which generally has more significant impact on people of color and people from a lower income socioeconomic strata? Did you feel like you were a bit of an outsider in the system?

Josh MacDuff: I certainly— In Vermont, I probably was. I was your stereotypical cannabis dealer but my upbringing I wasn’t— Now, I’m I guess I would consider myself – if it exists – a middle class worker. But my dad worked in the slate quarries and we were very low income as well. So maybe that influences what got me in to selling cannabis in the first place. I wouldn’t necessarily say that I was profiled any differently. But again, it’s hard to put a barometer on it in a state that’s – especially at that time which was about 2005 – was significantly white, very predominantly white as far as that goes.

Kathryn Blume: Right. So, it’s hard to tell— The social justice issues that we talk about a lot which are much more visible in larger communities don’t raise to the top of people’s awareness in Vermont quite so much.

Josh MacDuff: That’s correct, yeah. And I guess to further kind of clarify that, a few short years later while I was still a convicted felon, I got pulled over for a simple traffic violation, and I had, like, a license plate light was out. And they pulled me over on my car and in— The police officer was calling it in and I could hear the dispatch guy verbally calling me a dirtbag. It was really, I guess, interesting to be labeled that way by law enforcement. Because obviously, I do have a record. It gave them more of an emphasis to try to search me, to try to find anything that they could to really to really stick it to me.

Kathryn Blume: And did they get you for anything?

Josh MacDuff: I think I had some license status issues but it was because of an unpaid ticket. But no, they didn’t.

Kathryn Blume: So, you didn’t have weed in the car, you didn’t have—

Josh MacDuff: Well, I did but I put it in my shoe—

Kathryn Blume: [Laughs].

Josh MacDuff: —which is a very— I don’t know if I should be giving tips to kids these days, but until you go into booking, they can’t really take off your shoe. I was able to get it into my shoe.

Kathryn Blume: I went across the Canadian border once with cannabis in my feminine care products, figuring that was not something they were going to take a look at unless they really, really had to.

Josh MacDuff: Dire times call for dire measures.


Kathryn Blume: So, you’re now clean living law abiding citizen – as from the legal perspective – and you’re working in the insurance industry.

Josh MacDuff: Yes, absolutely.

Kathryn Blume: How’d you get into that?

Josh MacDuff: It started with me coming out of my 2-year college with an associate’s in accounting and a local insurance company took a flyer on me in 2010, and it was on the carrier side. So I was actually representing a company as an underwriter. And now I’m on the agent’s side where I’m actually selling insurance, commercial insurance.

Kathryn Blume: And what makes the work compelling for you?

Josh MacDuff: I think in sales, you have to find something that helps you kind of sleep at night in what you do. And that’s really been my focus here on the cannabis industry, as well as a lot of my clients are farmers. I found an area where I feel there’s an underserved market and I want to be that point person. I want to be the person that provides them solutions that help their businesses succeed. For farming as an example, I found that a lot of— Oftentimes, I’ll sit in front of a client and they’ll tell me that they weren’t able to do X business venture because their insurance company wouldn’t cover them for it.

I don’t want ever to sit in front of a client and tell them that any plan or any vision that they have for how they run their business is off the table. I found a tight knit community within the farming industry and I’m working my way into the cannabis industry in the same capacity. Because again, it’s an underserved market today. It’s not gonna make me rich by any stretch of the imagination and if that’s all I’m in sales for, then I’m no better than anybody else.

Kathryn Blume: What are the challenges for writing policies for the cannabis industry right now?

Josh MacDuff: You would think in a state like Vermont, this wouldn’t be the case but it’s a 100 percent unknown so the liabilities with— Right now, so really what we’re really talking about in the cannabis industry right now from an insurance perspective is CBD hemp products. That’s really what’s kind of open as far as that marketplace goes.

Obviously, medicinal cannabis as well. But what I’m working diligently on currently is CBD and hemp products. And what’s difficult is there is no actuarial data to understand what losses look like, how to predict losses claims payouts on the products liability side. So that kind of aligns with the fact that there is no medical surveys and studies, no real—

You know how driven we are by the pharmaceutical industry having spent billions of dollars on developing these studies that tell you cause and effect of consumption of a product. That doesn’t currently exists in the form that an insurance company can get comfortable with from the CBD and hemp products standpoint.

Kathryn Blume: How were you able to write policies for folks?

Josh MacDuff: There are markets out there. They are very difficult to— From a pricing standpoint for my smaller producers. But what I think separates myself from the rest of the pack is that I continuously turn over the stones.

So, I’m actually working with a partner. Our agency is a membership of what’s called an Insure X Global partner. We’re the only ones in the state of Vermont that represent Insure X Global. And we work with other agents within the country and it’s a global partnership.

So, we’ve been in other countries to provide support to one another. And we’ve actually been in contact with West coast California domiciled insurance brokers who— They’ve got obviously a much larger landscape of products and offerings to try to bring products in. Whereas the rest of the insurance industry both at the company level and my level— The agency level is waiting for the products to come to them, waiting for the solutions to come to them. We’re actually putting in the work to find new products and offerings that can help make the process go smoother for our clients.

Kathryn Blume: So, when you’re talking products, you’re talking policy so that it’s not just, “We only have one blanket policy for you because this is such a new industry.” We’re trying to craft a whole suite of policies that best fit whatever your business is at whatever level you’re operating.

Josh MacDuff: Absolutely, so that’s exactly it. So we— Right now, we’re working with brokers who are domiciled in Vermont. As well as— I’ve been working with an insurance company out of Illinois as well as— Again the company in California to bring in more offerings, to bring in more policies, more liability options.

I’m not going to get too into the weeds on the makeup of a general liability policy. But when I look at what’s out there in the marketplace for us currently, it makes me sick to my stomach, because they’re not protecting the policyholders. You’re paying a premium and you’re not getting the type of protection that I’m comfortable selling. Because you look to us when something goes wrong. We want to make sure that you don’t have to close your doors because of it.

Kathryn Blume: So, it’s got to be a lot of creative investigation and maybe a little bit of wheeling and dealing on your part to try— Particularly because you’re not an insurance mogul yet at this point in your career. I would imagine the amount of industrial power you have is fairly limited. So you have to find really, I think, probably, alternative solutions for people.

Josh MacDuff: Right.

Kathryn Blume: How do you back that up financially when you’re dealing with something as potent as a liability issue?

Josh MacDuff: You know from an agency standpoint, our bottom line isn’t affected by what the dollar amount of the claim is paid. Really, my job right now is to— And I’m as an employee of an agency, I’m not an owner. I don’t get paid to research these markets. It’s me doing my due diligence within my time to— Like you said build a bigger empire of clients, to build a larger landscape where it does eventually bring in revenues to the agency makes it advantageous for our agency to be the go to in the cannabis industry.

Kathryn Blume: And I would imagine the more policies you write, the more clients you have, the greater variety you have, the easier it gets over time.

Josh MacDuff: Absolutely. And then, as new markets come available, and they get into the state of Vermont, and they want to do business in Vermont, we’re the first agency that they go to. We’re the resource because we’re the experts and that’s really—

We’re really starting this from the ground floor. And it’s really me with the blessing of ownership to go on the crusade. And hopefully, I’ll be able to bring my peers up as well, and get them educated on the ins and outs of a cannabis operation, as well as the what that looks like within the construct of an insurance portfolio.

Kathryn Blume: Did you have to convince your business that this was something that was going to be of value, or were they are pretty onboard from the beginning?

Josh MacDuff: Yeah, it’s a mixed bag. I mean, one part of our ownership team is probably more cautious with what generates the most revenue in me not spinning my wheels on things that currently don’t. But then, I have another part of the ownership that is very bottom line driven. And if I can show him that this is a long haul, this is in the first two or three years, this won’t make me any money, but as new markets come up, it could be a very nice opportunity.

And I think they laughed at me a lot just because they’re baby boomers and they see a young millennial chasing business that’s not going to make them money. And they have this vision of me sitting around with a four foot bong and just really kind of having this powwow and eating Doritos and not getting a lot accomplished. It’s my job to make sure that they understand that—

Kathryn Blume: Disabuse them of that notion.

Josh MacDuff: Exactly. Disabuse them of that notion, and make it understand that— I mean within this industry, there are so many polished professionals now. And it’s amazing to see the entrepreneurial spirit of them all, as well as the folks that are out there like yourselves pushing for reform. I mean it’s amazing to see it. I just read an article actually on Heady Vermont from within the Castleton University and UVM pushing to put together a program for these entrepreneurs.

It’s amazing and it’s funny because one of those professors (who will remain unnamed) as— is somebody I know personally and was very proud to see their name in – just like the podcast – coming out of the shadows, and really stepping into the light and letting people normalize the industry. So that you can understand that a professor can be a proponent of cannabis and a consumer recreationally, and still be a good productive citizen. And the insurance agent can do the same and not let your house go up in smoke as a result, or your investment banker can still help you make money in retirement while enjoying a little recreation on the side.

Kathryn Blume: And, without again getting too granular or technical, is there a particular project that you’ve worked on, policy you’ve written, research that you’ve done that for you was either super fun or meaningful, or you were able to pat yourself on the back because it was so freaking clever?

Josh MacDuff: [Laughs].

Kathryn Blume: Was there one that stands out for you?

Josh MacDuff: I have a small producer right now who had a farm, who has a farm, and is producing CBD products and he– bless him was very patient with me. He was very unique. His operations existed within a dwelling, and in it made for challenges to get the necessary coverages from a property and a liability standpoint.

And I filled out hundreds of pages of applications for this gentleman. And it became a passion project for me because again, it was a small operation, growing operation I should say, and a very new venture. And we’re working hard for him. I’ve lost money on the deal but I’ve gained, I think, the respect of somebody who otherwise would be exposed and unprotected from the liabilities and the common exposures that a business owner faces.

Kathryn Blume: Looking at the current arc of legalization both in Vermont and across the country, and really around the world, where do you see things headed and what gives you the greatest hope and what are you still concerned about?

Josh MacDuff: I see with some of the larger metro areas really adopting legalization and in recreational use and sale that— Let’s take Massachusetts as an example with Boston. There are a lot of insurers who who actually reside in Boston, standard company insurers who in two years, I mean they have— Somebody has got to step up to the plate, and I think with all of the influences, New York pushing for legalization. I mean, if New York can make it happen and find a way for it all to work nicely— I mean, New York is probably the most diverse state just given the construct of the state. And then you have New York City kind of hopefully forever being still part of the state, but really skewing the median there.

I think it gives me a lot of hope that in two or three years, all of our neighboring states will have some semblance of legalization and really normalize cannabis use both recreationally and medicinally, and get rid of all of the stigma that’s around it. And hopefully, the insurance companies will flock to it just like they do the craft brewery scene or— And now, I think we’re even seeing now where we’re breweries or brewing beer with THC in it. I mean it’s what can you do at that point? I think you have to fall in line and then somebody is going to step up to the plate, and I’m very confident in that.

Kathryn Blume: And there is a banking bill working its way through Congress right now on the federal level.

Josh MacDuff: Mm-hmm.

Kathryn Blume: I would imagine if that passes that also makes your job easier.

Josh MacDuff: Yeah, exactly. Again, one of the— I think hinges is first of all, the fact that it’s federally illegal currently. But the other is that where does the money go? Because right now obviously CBD and hemp products is a little bit different but there’s no real banking system that has stepped up to the plate as well to allow for those funds to go through. Which, from an actuarial, from an insurance standpoint, if there’s not a hardcopy paper trail to your revenues and your payrolls and everything involved with overhead, it makes an insurance company a little weary that you’re – that you’re kind of underestimating or are exaggerating your actual sales.

Kathryn Blume: That’s a great image of an insurance company being weary.


So, sorry you’re tired.

Josh MacDuff: Yeah, exactly.

Kathryn Blume: There’s still a lot of people in the general public who are unfamiliar with cannabis, and there’s a lot of, sort of, second generation reefer madness misinformation running around. If you had the opportunity to speak to the general public, people who don’t know a whole lot about cannabis, what would you want them to know?

Josh MacDuff: I think I would want them to – just like the stigma that I originally got with my owners at the insurance agency – to understand that there are people out there who use it in the right way. And to keep an open mind and really wrap their heads around the studies that we’re finding of the amazing things that it’s doing medicinally. And then to understand that you can be in a normal functioning human being and still have a well a little fun on the side. It’s no different than drinking. I prefer not to drink. I just wish that people would understand that there could be this great opportunity to have a few tokes after work with your co-workers, or have an insurance company who typically would bring you out for happy hour. Sorry, not happy hour. For a drink after work and they could do the same with cannabis and they’d be delighted at, I think, how capable they would still be to function thereafter.

Kathryn Blume: Is there anything I haven’t asked you that you really want to say?

Josh MacDuff: Not at all. I think I really like what Heady Vermont is doing and the direction that they’re helping take the state of Vermont. And what I would say is that I want to be a part in any way possible. I want to be able to control what I know well about the cannabis industry and in my profession and really help the same people that you’re trying to help to find their successes within their own right.

Kathryn Blume: And that my friends is it for this episode of Unhidden. I’m your host Kathryn Blume. Thanks to the whole team and Heady Vermont; Monica Donovan, Eli Harrington and Luna the Wonder Dog. Thanks also to Josh MacDuff and his colleagues at Kinney Pike Insurance and to West End Blend for the excellent music. You can find happy Vermont on Facebook, Instagram, Twitter, YouTube, iTunes and Headyvermont.com. Look for the Unhidden Podcast at Soundcloud, iTunes and wherever fine podcasts are sold. We’ll see you next time.

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