051: How Cannabis Entrepreneurs Can Leverage Virtual Assistants with Tajanna Mallory

Over the last half-decade, there’s been an explosion in interest in virtual assistants. Entrepreneurs of all kinds have hired remote support staff to do all sorts of tasks: making travel arrangements, managing calendars, briefing team members before conferences or engagements, and even assisting with content creation and social media. This is as true of cannabis as it is with other industries, but it comes with its own hurdles and challenges.

To learn more, we’re talking to Tajanna Mallory, Founder, and CEO at CannAssistants. CannAssistants is a virtual assistant agency that provides administrative support to mid-size cannabis companies, founders, and business executives. She has over a decade of experience providing administrative support, H.R., and talent recruiting services for large teams and C-level executives in the for-profit and not-for-profit space. She’s worked with Fortune 500 companies, including Deloitte & Touche, the NFL, Pfizer, Comcast, Chick-Fil-A, and Oliver Wyman, to name just a few.

In this episode, Tajanna shares the story of her journey from corporate America to the cannabis industry, how she helps entrepreneurs take administrative tasks off their plate, and how CannAssistants empowers virtual assistants as business owners themselves.


  • Why virtual assistants are a versatile and affordable way to scale a company.
  • The unique issues facing cannabis entrepreneurs (and the virtual assistants working with them) as they grow their businesses.
  • How Tajanna finds the right assistants for her clients and creates opportunities for them to convert to full-time when an employer is interested.
  • How Tajanna sees diversity in the cannabis industry and within her own businesses.
  • What makes the career trajectory for assistants so unique–and how Tajanna helps her assistants achieve their goals just as much as her entrepreneurs’.
  • Why Tajanna doesn’t think full federal legalization will happen in the next four years.


  • “Virtual assistants are business owners. Not only are they able to make a living for themselves but they’re also able to grow a business.” – Tajanna Mallory




If you enjoyed today’s episode of The Green Repeal, hit the subscribe button so future episodes are automatically downloaded directly to your device.

And don’t forget to leave us a rating & review! Reviews on Apple Podcasts are greatly appreciated and will allow us to build awareness for the show. If you received value from this episode, please take a moment and rate and review the podcast by clicking here.


Do you have a question you would like answered on a future podcast? Email us at greenrepeal@sohoexp.com and we’ll do our best to answer it!





Rick Kiley: Hello, everyone, and welcome back to another episode of The Green Repeal. I am desperately waiting for the weather to get warm here in Brooklyn and spring just will not come. How you doing, Jeffrey Boedges? How’s New Jersey treating you?


Jeffrey Boedges: It’s actually pretty nice today. It’s not as nice as it is in Tampa, Florida but that’s just I’m not trying to give you a softball pitch set up here but you know.


Rick Kiley: Yeah, I love a nice segue. A geographical segue.


Jeffrey Boedges: Yeah, that’s what we do.


Rick Kiley: Joining us from sunny Tampa, Florida today, we welcome Tajanna Mallory, the founder and CEO of CannAssistants, a virtual assistant agency that provides administrative support to mid-sized cannabis companies, founders, and business executives. A core tenet of her work, Tajanna believes the foundation of every strong organization is steady and seamless support staff, man, I love all those S’s in a row, that excels in daily operations and exceeds client expectations. In 2016, after spending over a decade providing administrative support, H.R., and talent recruiting for large teams and C-level executives in both the for-profit and not-for-profit space, Tajanna launched her own business aimed at providing these much-needed services to the cannabis industry. Her expertise spans startups, technology, finance, education, hospitality. She’s worked with Fortune 500 companies like Comcast, Chick-Fil-A, Deloitte & Touche, the NFL, Pfizer, and Oliver Wyman. Oh, my gosh. The list goes on. She has a Bachelor of Arts in Religion from Florida State University, surprising, and a Master of Arts in Theological Studies from Liberty University. And she currently lives in Tampa, as we said, with her husband and their chihuahua.




Rick Kiley: Tajanna, welcome to The Green Repeal. I’m going to pause to let my cat in for a second and she is freaking out.


Jeffrey Boedges: And I’m going to say go Seminoles.


Tajanna Mallory: Thank you. I appreciate it. I love me a – did you go to Florida State?


Jeffrey Boedges: I didn’t. No. I’m one of those guys that got on the bandwagon early to hate all Florida college football teams because they were so good for so long. But now they’ve been bad for so long, I have flipped the script. I’m ready for them to come back and assume their rightful role as the evil empires of college football.


Tajanna Mallory: Yes. That is definitely a practice around the state here. We love to run into other people wearing their favorite Florida college team, and we like to bash them and completely trash talk in the middle of the aisles at Trader Joe’s or Wal-Mart. It doesn’t matter. Because when it comes to college football, the tact is all the same.


Rick Kiley: I feel like the trash talking at Trader Joe’s is different than the trash-talking at Wal-Mart. Is it not?


Tajanna Mallory: I agree with that.


Rick Kiley: Okay.


Tajanna Mallory: I would say bigger words versus smaller words, something like that.


Rick Kiley: Well, one store also has guns and the other doesn’t.


Tajanna Mallory: That is actually actual factual. Both have cheap wine.


Jeffrey Boedges: Oh, good. Yeah. There you go.


Tajanna Mallory: So, either way, it’s going to be a good conversation.


Jeffrey Boedges: Awesome. What a great segue right into…


Rick Kiley: Well, we’re already off track. Let’s try to get back.


Jeffrey Boedges: Sorry. Rick stepped away, and I took right off the rails.


Rick Kiley: As we go. So, I mean, I think, we got through that whole intro and then, of course, at the end and the reason we left your studies in there is because I’m just super curious how someone who is a student of religion, theology ends up running a virtual assistant agency in the cannabis industry.


Jeffrey Boedges: Yeah. That’s not a linear progression.


Rick Kiley: Yeah. You got to have the path there. Is it on a multi-variable equation?


Tajanna Mallory: It’s a very interesting story. So, I was in college, first generation of college student. My family had moved from Chicago to Tallahassee, Florida, which was culture shock in and of itself.


Rick Kiley: Yeah.


Tajanna Mallory: And I lived in Tallahassee, Florida for 12 years. I stayed for college. At the time, my family was super involved in the church, and I also wanted to go into a career of journalism. So, the plan was to write for a journalistic Christian or some type of like faith-based magazine or journalistic periodical, which…


Jeffrey Boedges: The Science Monitor or something along those lines.


Tajanna Mallory: Something. You know, Christianity Today. I don’t know. Something like that. As I continued on in school, so initially I was going to college for communications. As I was doing my pre-reqs, I kept taking all these religion courses. I’m super interested in culture and languages like fascinated by it. It didn’t dawn on me to go get a degree in linguistics. Instead, I just kept taking these religion classes that had nothing to do with my communications courses, and I also really wanted to get out of college. So, come year three, my advisor is like, “I don’t know what degree field you think you’re in but you’ve taken so many of these courses, you can finish in another year if you just go ahead and graduate with this religion degree or another two years.” I was like, “No, the two years is not an option.” So, I went ahead and got that Bachelor’s in Religion. We love the coursework.


My first job right after college was as an administrative assistant for Deloitte & Touche, and that was where I kind of sunk my teeth into the administrative work and what it looks like to work for like a big company. Deloitte is an international firm. They’re most known for being one of the four big accounting firms. I worked on the technology side but that’s where I started to get my taste of like real-life corporate world, what the role of like project managers looks like, what administrative support work looks like. And then I went and got a master’s just as like a plan B in case I don’t like this kind of work but I finished that master’s.


Rick Kiley: Yeah. What’s interesting with your story here is you finished the religion degree out of convenience and then got a master’s in more religious studies. So, something must have shifted.


Tajanna Mallory: It was like the plan B was going to be like, “Oh, I could always get a job and teach at like a Christian school or at the university level,” and I didn’t do that either.


Rick Kiley: All right.


Jeffrey Boedges: So, now it’s all clear.


Rick Kiley: So, the work at Deloitte & Touche paved the way towards this virtual assistant industry. And so, everyone at Deloitte was just token up like where did the cannabis come in?


Tajanna Mallory: The cannabis was completely by accident. So, I’m climbing up this corporate ladder. I’m an administrative assistant. Then I become an executive assistant. I go into some project management, I go into executive assistant, work in H.R. all the way to the point where I’m supporting CEOs, board executives, the whole nine, right? So, I’m at the top part of my administrative support career and I want to travel. I don’t want to drive to work anymore. I don’t want to sit in a cubicle anymore. I don’t want to do any of these things. So, I started researching ways in which people are traveling the world and making money. And I kept coming across this virtual assistant, virtual assistant, but it was really popular in like the Philippines. Some people were doing it in Europe but nobody was really doing it on like a great scale in the United States. And at this point, I had ten years of experience. And I’m talking to my husband about it and he’s like, “Just quit your job and do it like you’re miserable. You hate it there.” He’s like, “Just do it.” And I did. And my first client right out of the gate was in the cannabis industry.


Rick Kiley: All right.


Tajanna Mallory: That’s how I landed in cannabis. Back in 2016, there were not as many legalized states as there are now. Remote work was not super popular in 2016, so like the whole thing was just fairly new.


Rick Kiley: Right. So, you caught a little lightning in the bottle with the virtual assistant thing getting in there before it was needed.


Tajanna Mallory: Yes.


Rick Kiley: Nice.


Tajanna Mallory: Not to say before it was needed. I would say before it became popular or I would even say before people even understood what it looks like to have an assistant in this industry.


Rick Kiley: Right. So, then talk to me about like let’s explain for the people who are listening in for the person talking right now. What exactly is a virtual assistant? We’re not talking about like the AI that Siri in your phone. This is…


Jeffrey Boedges: It’s a robot.


Rick Kiley: This is a person?


Tajanna Mallory: It’s a real-live person.


Jeffrey Boedges: It’s a robot that sits in your office.


Tajanna Mallory: No. It’s a real-live. It is not the Jetsons. What was the lady’s name who came around with a tray?


Rick Kiley: Rosie.


Jeffrey Boedges: Rosie, yeah.


Tajanna Mallory: Rosie on her wheels or wheel. No. So, a virtual assistant is, first of all, the first thing you should understand is generally they’re freelancers or contractors. You can also hire a virtual assistant agency to find someone for you but essentially, it’s a person who works independently and their services can range from anything from a general administrative support. So, things like travel arrangements, managing your calendar, preparing executives or professionals for speaking engagements or going to conferences, helping with the event planning all the way to there are virtual assistants who strictly specialize in things like content creation and social media. So, the beauty about the virtual assistant world is that there is no clear like in concrete definition about the scope of work that a virtual assistant can do. It’s really more so about their skill set.


Rick Kiley: Okay. Got it. And are they fractional in nature? Meaning, like, are they not full-time? They are often, is it like someone’s getting someone for 8, 12, 20 hours a week, that kind of thing?


Tajanna Mallory: Yeah. So, most times virtual assistants do work with several different clients. So, yeah, that’s another beautiful thing about it is that you’re not having to hire a full-time employee. You’re able to have someone who is a subject matter expert, and you can get them at a part-time because, as a freelancer, they’re working with a lot of different clients. So, you can get them at part-time hours, yes.


Jeffrey Boedges: So, they’re carrying around four cell phones? How do they figure out who’s call they’re answering? That’s what I want.


Tajanna Mallory: So, it really just depends on who that assistant is. So, with CannAssistants, we have a lot of different communication methods. Some of those are ways in which the client has a preference. So, you might say like I just want to be texted like don’t email me because I’m never going to check it anyway or your assistant is the person checking your email, so it’s no need for them to email you for an email they’re going to check.


Jeffrey Boedges: Right.


Rick Kiley: Get someone just to check my email, that would be great.


Tajanna Mallory: Yeah.


Jeffrey Boedges: Yeah. I would just like somebody that says…


Rick Kiley: Delete all my unneeded emails.


Jeffrey Boedges: “You’re about to be late for a meeting.” That’s the virtual assistant I need, you know.


Tajanna Mallory: And we do that as well. Not only can we check your emails and tell you when you’re going to be late for a meeting but we can respond on your behalf for those emails or even attend those meetings in your stead. So, again, it’s really just about the partnership that you have with your assistant, the type of work that you do, and how they can help you manage all of those things.


Rick Kiley: Got it. So, I…


Jeffrey Boedges: I think you’re kind of golden.


Rick Kiley: It’s basically pitching our business today. I’m like sign me up.


Jeffrey Boedges: Yeah, I’m in.


Tajanna Mallory: One of the things that I love to tell people is that, first of all, a lot of times busy professionals, especially business owners, they don’t go into business to do administrative work unless you are me, who is the person who did go into business to do administrative work. But generally, you’re spending a lot of time doing things that don’t really excite you. You’re probably not even really good at it, to be honest. And so, you want someone who is fueled by that type of work, and that’s what they specialize in. And those things can get knocked off of your plate a lot faster than you are looking at it on your to-do list.


Jeffrey Boedges: Can I ask the obvious question in cannabis? Do you feel like maybe some of the people who need assistance are a little bit more absentminded than the average businessperson?


Tajanna Mallory: Tell you this. This is what I have now…


Jeffrey Boedges: Go on.


Tajanna Mallory: Specific to this industry is that I spend a lot of time talking to people who have never worked in a corporate environment before, or if they did, they did not have the benefit of having an assistant to help with their workload. So, a lot of times I’m educating business owners, unlike what even an assistant can do for them in this industry, and then obviously convincing them to hire us. We have a rule on our team. One of the things that I tell assistants who come to us who may have never worked in this industry before is that if you are on the call, it is very possible that your client is going to light one up on the phone right then and there.


Jeffrey Boedges: Yeah. They’ve been on our podcast.


Rick Kiley: Yeah.


Tajanna Mallory: I’m like that is your moment. You take more intense notes than like any other time that you’re taking notes and you’re keeping up with all the things. Also, that’s not your opportunity to light up. That is your opportunity to like listen but this is where like all the creativity is about to come out.


Jeffrey Boedges: Does that need to be covered? Is that like not something that’s obvious?


Rick Kiley: Yeah, I think that’s probably.


Tajanna Mallory: Part of our orientation.


Rick Kiley: I bet it is. I bet it is. Yeah.


Jeffrey Boedges: Yeah. We might have to add that to our own.


Rick Kiley: So, I guess my question, when you launched the agency, was it always intended to service the cannabis industry exclusively? Like, was that always an intention or did that just sort of like happen as a result of the first couple of clients you picked up and you were like, “Hey, we got a real niche here.”


Tajanna Mallory: Yeah. Okay. So, two things that happened that were not on purpose but are the best things that ever happened. The first was I did not intend to go into the cannabis industry at all. It wasn’t even an industry that I was aware was an industry. When I got my first two clients right out of the gate, second day I launched my business, one of them happened to be a grower in the cannabis industry and he was very, very busy because he had also just launched a nonprofit. And so, this gave me the opportunity to look into this industry and I got to see how someone who is a cultivator in one state is like nationally known, and traveling to states that are not even legal, also is known and asked to come and speak about more than just cultivation. So, there was where I really got to see a lot of service lines that exist in this industry and what are a lot of things that the entrepreneurs are doing, what are they involved in. So, I did not intend initially to be in the industry but I did lay in here kind of really immediately as soon as I started.


I also did not intend to have a virtual assistant agency. I really just wanted to like pay my bills and go hopscotch in Mexico. And so, what ends up happening was it just kind of became word of mouth and we kept getting more clients in this industry. And I couldn’t take on all the work. So, then I started hiring and subcontracting with other virtual assistants. So, both things happened by accident but both things put us where we are today.


Rick Kiley: Got it. And does anybody call you from the can industry because of CannAssistants?


Tajanna Mallory: No.


Rick Kiley: No? That would be weird because people are making cans and need assistance out there. Alright. Good.


Tajanna Mallory: No. But you know what, we’ll take them too.


Rick Kiley: I bet. Yeah. So, I guess that’s a question. If someone called you and said, “I want to hire you but I’m not in the cannabis industry,” are you taking that business or are you saying, “Sorry. Talk to somebody else.”


Tajanna Mallory: No. We do take those clients. We have another arm of our business, Modern Assistants. And so, we do take clients from all industries. I always say that cannabis industry professionals like working with other cannabis industry professionals.


Rick Kiley: Sure.


Tajanna Mallory: So, we did line out a cannabis-specific arm of our business to just let them know we’re here for you and we are working in this industry alongside with you.


Rick Kiley: Nice. Okay, cool. And so, when you’re hiring, then people to work as a cann assistant specifically for the cannabis industry, how are you finding the talent? Are you finding professionals who have been executive assistants before and then training them up on cannabis? Are you finding people who have an affection for cannabis but just happen to be organized like…?


Jeffrey Boedges: Who’s calling? That’s what I want to know. I think it’s probably people who have an affection for cannabis first, right? “Yeah. Hey, I love weed and I like taking notes. I’m your perfect employee.”


Tajanna Mallory: Yes. And because of that, so we recognize that we work in a very unique industry that is cutting edge with a lot of people wanting to get involved, right? But being an administrative support professional is a specific type of work as well. So, I can’t have someone come to me and say like, “Hey, I really want to work in the cannabis industry but I’ve been in retail or even at like a higher level of like, I don’t know, a human resources executive.” And so, it’s really a combination of skills that they already have and transferable skills and the desire to work in this industry and to be passionate about the plant. So, those are the things that I’m weighing when I’m having these conversations. Do you have transferable skills? You were not already working in an administrative support field. Do you have a passion or a desire for administrative work? Do you even understand the importance of administrative work? Because that’s super important. Are you able to handle a lot of the soft skills, like the customer service skills and the client relationships? And can you be proactive?


So, there are a lot of like soft skills that come into play that I had during those interview conversations. But also, for people who want to work in this industry, it’s a great opportunity to give them an opportunity to do so but that is also kind of like a separate vetting conversation that we have as well.


Rick Kiley: And so, are some maybe, let’s just say, has it happened where there’s a company that starts working with somebody through you but then they’re like, “I want to hire this person full time,” and they buy them out. Like, do you offer staff placement services as well?


Tajanna Mallory: Yes. We do offer that as well and we are actually pivoting more so to that model because I have found that, one, if I can match a great assistant with a great professional and that relationship can work out very well, I’ve done my job, right? I’ve done my part. But also, there is a growing number of assistants or people who want to work as administrative support professionals in this industry and I found that I love building the community of that, the community of those assistants, making sure they are trained, making sure they’re understanding what’s going on in our industry. It’s super fast-paced, you know. So, we’re figuring out a way that we can marry the two, the virtual assistant enrichment community and training, and marry it and continue to broaden that as we continue to grow out our agency.


Jeffrey Boedges: Can I ask, do they make decent money? Is this something that we should be promoting right now and everybody saying, “Hey, if you’re interested in making money, this is a good place to start?”


Tajanna Mallory: Yes. So, virtual assistants make, let me say this, a couple of things. First, I would say it depends on a lot of things like niche, how specialized they are, how many different ways can a professional utilize their virtual assistant services, right?


Jeffrey Boedges: Right. So, the more services you offer, the better money you make, period.


Tajanna Mallory: And I would also say the better data you have about results. So, if you’re in social media management, when you can grow engagement and you can grow followers and you can build a newsletter list and things like that like that’s going to be so valuable for a business owner. So, what virtual assistants charge is it’s completely up to you. Yes, though, they do make a very good, livable wage. And I think that’s the benefit of being a US-based assistant versus assistants overseas. They charge a lot less money but you deal with things like language barriers and time zone issues that they don’t always coincide well with the professionals that are here on the East Coast.


Tajanna Mallory: Yeah. So, virtual assistants are business owners. I mentioned that before. So, not only are they able to make a living for themselves but they’re also able to grow a business.


Jeffrey Boedges: Are you helping them get like companies like organize like create their own little fees and things like that to help? I mean, from a tax perspective, obviously, right, you don’t own your own business. You need to be able to discount or to take those rebates.


Tajanna Mallory: So, tax advantages, yeah, for sure. And that’s a part of that virtual assistant community and training that like we talk about on that side of the business. We’re talking about ways that as a virtual assistant, how can you grow? How can you make sure that your business elements are established so that you can take advantage of being a business owner? Absolutely. And also, being able to plug into some of their local like government contracts or city work that is available from being able to have their own business.


Rick Kiley: Got it. So, the way that you’re structured then is a client contracts you and you’re subcontracting to another entity that is the virtual assistant. They are or are not your employees? Or is there some a little of both?


Tajanna Mallory: All of our assistants are subcontractors. They are not actual employees. We do that, I have done that because, again, to the vein of wanting to empower business owners in this industry but also allowing them an opportunity to work with professionals in this industry.


Rick Kiley: Got it. Okay.


Jeffrey Boedges: And how’s the turnover? I mean, are you pretty solid? Like, people come in and they stay or how transient is it? In our industry, we have different roles, have different levels of transience but it’s an expensive proposition, which you have too much turnover.


Tajanna Mallory: Well, that’s a great question. I am constantly in contact with our assistants on both the client work that they are doing on behalf of CannAssistants but also their businesses. And I think this was something that early on, being a leader in business, I wanted to set myself apart. I have worked for over ten years as an executive assistant. I understand what it is like to be treated as an executive assistant in corporate America. Honestly, it can be you’re high on a pedestal or you’re like the last person that anybody is paying attention to. Keep in mind, though, doesn’t matter which company you’re at, high on a pedestal or people pushing you in a corner and treating you like a servant. Either way, administrative professionals are the ones who run these organizations. So, either way, they deserve the highest level of respect that anyone does. And so, I forgot the question that you asked me and how you got me on the like soapbox.


Jeffrey Boedges: Just about level of transience, just about people turning over.


Tajanna Mallory: Oh, yes, yes. Okay. So, with that being said, I have taken that experience from corporate and I’ve brought it kind of into my own company. And so, the way I try and lead is in a holistic view, right? So, I’m working with assistants on the client work but I’m also asking them about their businesses. Do you have any hang-ups in your business as you’re trying to grow as a professional? What are some skills that you feel like clients are calling for but maybe you’re lacking in? So, we do a lot of training. I do a lot of training, coaching, and enriching. So, because of that, I think I have had very limited turnover because I’ve made sure that we have just such a great environment to work in.


Jeffrey Boedges: It’s a partnership, yeah.


Rick Kiley: It’s definitely a true partnership but also, it’s just building that assistant community once again. Like, you work so siloed as a solo virtual assistant that that community is just really integral for building your skillset.


Jeffrey Boedges: Okay. So, you gather all the assistants once a week, once a month for like a group therapy or a powwow or what?


Tajanna Mallory: We do have team calls for sure but I have one-off calls with all of them. And then on the client-side, I’m always checking in with clients as well, “How is your assistant doing? What are some gaps that you think need to be filled? Where are some areas where you think some fine-tuning need to happen or where you’d like for them to be a little bit more professional? Where do you want them to speak up or maybe speak a little less?” So, I’m having those conversations with them as well. That makes for, one, great rapport with our clients and they really feel supported, two, great rapport with our assistants because they’re getting that feedback as well and they’re really understanding where they can train up in some areas.


Tajanna Mallory: All right.


Jeffrey Boedges: It’s impressive. You’re going to come work with us and teach us a couple of things. I mean, Rick and I now I think…


Tajanna Mallory: I think you guys are doing great.


Rick Kiley: Oh, thank you. That’s kind of you to say but we probably both need virtual assistants or real assistants or just assistants in general like the verb.


Jeffrey Boedges: Like professional.


Rick Kiley: So, one question I have is we’ve interviewed a lot of people in the industry on this podcast. And one sort of common thread of what’s happening in the industry right now is an interest for, a need for to talk about diversity, inclusion, and social justice. And sometimes that’s reflected in people’s hiring, in their H.R. practices, of course, in these different companies. I’m curious if you’ve found that you have had to create a strategy in the virtual assistants that you are trying to bring on that fit into a DEI need that in for some companies may in fact be a mandate. I’m just curious how you address that with what you’re doing.


Tajanna Mallory: You know, I think that the first approach that I take in which I’m not sure how many companies are doing that and that is really just looking over the landscape of our industry. There’s a lot of diversity in this industry. It’s certainly not enough but there is enough diversity in this industry to see where diversity needs to grow, if that makes any sense. So, I can see some areas of people. I can see some areas of genders. I can see some areas of even skillset and I’m also saying where they need to grow and expand. And so, that’s kind of where I look at it and I’m also looking at it on my team. So, if this is what I’m seeing in the cannabis industry and this is where I also am hearing people say we need more diversity, I’m also paying attention to my team. Does our team look like the industry? Does our team look like the clientele of the industry? And does our team look like what people are saying we need more of like do we have that on our team?


Rick Kiley: Yeah.


Tajanna Mallory: So, for me, like right out of the gate, seeing the clientele and making sure that I am hiring as our industry is continuously reflective of that and also diversity of skillset. And that’s super important on our team. And it’s super important to continue to help the assistants on our team have diverse skill sets as well. So, if an assistant says to me like, “I’m heavy in social media but I want to learn more general administrative,” then we’re going to work on a plan in order to do so. And I think that’s where the DEI is really important is once you have diversity on your team, how are you helping them to scale up and build up I think is another area that needs to be paid attention to.


Rick Kiley: Okay. Yeah. That’s good stuff. And so, when you’re going out and trying to solicit clients, when you’re trying to generate business, how are you doing that? I mean, obviously, we’re going to be able to get you connected to all of our listeners on this show but doing podcasts is probably only one part of your business development plan, I would imagine.


Tajanna Mallory: Yeah, definitely. Conferences are opening back up so I’m showing up there, which is awesome, by the way. I think it is such a great soil for connecting and networking. It sucks that we have been in this like pandemic for I don’t know how long this seems like forever now and events are opening back up and everyone’s so excited to be at an event. So, everyone is just really like salivating to connect with other people. So, it is so great.


Jeffrey Boedges: And you should sell for us too, by the way, because that’s exactly what we tell people every day, you know.


Tajanna Mallory: And also, I would say just participating in a lot of workshops with organizations like and, for example, being able to participate in some of their cohorts and workshops and helping to really talk about how people can participate in this industry as an entrepreneur on the ancillary side of things. And so, that’s where I’m continuously showing up and having those conversations and as I have those conversations, I’m meeting new prospective clients and business owners along the way.


Rick Kiley: Awesome. All right. So, I mean, we talked about the world of events opening up again and you being able to do that. And one thing I was curious about is you said you started this business in 2016. Then, of course, we know that COVID hit and work life changed dramatically. I’m curious as to did your business shift dramatically, like when COVID started? And I feel like probably…


Jeffrey Boedges: I would think you were in the catbird seat.


Rick Kiley: It was like you and Peloton and Zoom really did well. But I’m just curious, like, did anything change specifically about your business or is it just like more need?


Tajanna Mallory: Oh, it was definitely more need. I will tell you a couple of interesting things that I was really grateful for during the pandemic. The first is that I was working in the cannabis industry because all industry folks know, when the pandemic hit, sales went up, right? Everybody was at home like now is the time to smoke all day every day.


Jeffrey Boedges: Goes home and stressed. I mean, I think everybody was like…


Tajanna Mallory: And stressed out, right.


Jeffrey Boedges: Legitimately, looking for some way to deal with.


Rick Kiley: Yeah. And they can’t watch the same movie again so they have to watch it stoned.


Tajanna Mallory: And then for folks who had kids at home, I was like, “God bless you all.” So, yes, our business was great. On the other side of our business, Modern Assistants, we have clients who are in sports and events and things like that. And so, that was not as great because everything shut down. But again, as a business owner, I was glad that we had these two sides to the business. Another interesting thing was seeing a lot of virtual assistants come into play. All of a sudden everyone was a virtual assistant. And I thought that was pretty interesting. Cool, but also interesting because not everyone had the experience.


Rick Kiley: For those of you not able to see her face right now. The interesting came with like a big side-eye. I mean, it was just like the side-est eye of side-est eyes. Holy moly, that was solid. I really wish you could see it.


Tajanna Mallory: I talk about this viral TikTok that went around because it was like it really got under my skin but it was like this 22-year-old who started a virtual assistant business. She had literally been at it for like six months and like completely went viral. And I did not understand for the life of me why she was going viral and why she was now a virtual assistant coach. So, I was like, “Oh, this is weird,” because I don’t think she has any experience.


Jeffrey Boedges: Right.


Rick Kiley: We’re in the post-experience age.


Tajanna Mallory: We really are.


Jeffrey Boedges: I’m curious about what needs are specific to cannabis virtual assistants versus your other side of the business. What’s the skill set difference? Is there one?


Tajanna Mallory: So, the skillset differences are more about pace of work and adaptability. So, this industry moves a lot faster. I tell people like something can be legal right now and by the time I get off of a call, it’s like, “Oh, well, I guess that’s not legal anymore.” Or states activate and all of a sudden like it just blows up and goes crazy. So, the pace is definitely different. And being able to like turn on a dime, like you got to be really adaptable and you have to be really, really flexible. So, I think those couple of things make it different as far as the work is concerned but as far as the skillset is concerned, I think being able to once again adaptability because you’re moving in a lot of different groups when you are doing so on behalf of a cannabis entrepreneur. So, you may be talking to a political official one day, you may be talking to your building inspector the next, your person’s general contractor. I mean, the vendors are just different multi-faceted.


Jeffrey Boedges: Yeah. That’s a huge scope. So, you have to be, yeah. You probably have to be fairly voracious in your appetite for information.


Rick Kiley: And how up-to-speed on like the compliance? Does your team need to be? I imagine that’s a pretty specific need for understanding.


Tajanna Mallory: So, it is generally information that we need to know but it is not like we’re not studying compliance rules or anything like that, one, for liability reasons. If I mess up a compliance rule like I can ruin someone’s entire company. But we do stay abreast of those things because generally, administrative support workers are the like person moving all the things in place, right? So, we need to have a general sense of compliance in that aspect for sure.


Jeffrey Boedges: Are a lot of the clients MSOs or most of them state-specific? I mean, I think if it was state-specific, it’s a lot easier to kind of figure out where the booby traps are.


Tajanna Mallory: So, honestly, we have both. We have had both MSOs with single state operators but also other ancillary business owners. So, knowing a little bit more about like some of their service lines is also super helpful as well.


Tajanna Mallory: Okay.


Jeffrey Boedges: Yeah, that makes sense. So, people that are, like you, servicing the industry on the whole are also your clients.


Rick Kiley: Right.


Tajanna Mallory: Absolutely.


Rick Kiley: And are you finding because you have these two sides of business, do you find the cannabis industry more open to the idea of virtual assistants than other industries? Or is it about the same appetite? I’m just curious.


Tajanna Mallory: Okay. So, that is a great question. Okay. So, the way this works is on the non-cannabis, on our Modern Assistants side of our business, I don’t have a hard time explaining to people what an assistant is and what they can do. It’s more so just explaining how we are so awesome. On the CannAssistants side, that is the side where I’m more so educating on what a virtual assistant is, why you need one, how we can increase your business’s bottom line. Those are the conversations I’m having. Once people understand the value, then I’m like, “Okay,” and we’re awesome so you should hire us. But that’s just really where the difference comes in. On the other side of it, most people are seeking us out. They’re like, “Hey, I need an assistant. They’re coming to us.” Whereas on this side, I’m like, “Hey, you need an assistant. Here is why. I’m seeing you, first of all, has six conferences. I’ve also been emailing with you through different organizations and you need some help. So, that’s kind of where the approach is different.


Rick Kiley: All right.


Jeffrey Boedges: Can I ask a question about like how – a lot of these companies have had a hard time paying people because of the banking issues. Has that been an issue at all for you with any of your grow side, distribution side, that type of thing?


Tajanna Mallory: So, we have to get creative with how we sometimes collect payments. So, the way…


Jeffrey Boedges: Go on. Yeah?


Tajanna Mallory: Yeah, you’re right. Okay. I should have paused. Let me explain that better.


Jeffrey Boedges: No, it’s okay. You know, we all do it.


Rick Kiley: Swiss bank accounts?


Tajanna Mallory: No, no, no.


Rick Kiley: Would it be a bitcoin? What do we got? Dark web. Where are we?


Tajanna Mallory: You know, for most people, we do auto charges to their card just like any other membership, your Netflix membership or whatever, right? Sometimes I had to like,I’m going to be at a conference. Let me see you then and I’ll just get your cash payment that day.”


Jeffrey Boedges: Yeah. I’ll take the briefcase.


Rick Kiley: Alright.


Tajanna Mallory: Sometimes I had to be a little like, you know, but generally we only do that for clients that we know and trust and have been working with for a long time.


Rick Kiley: Right. They drive up with like the Brinks security truck.


Tajanna Mallory: Not like that. No, no, no.


Rick Kiley: It’s going to be solid.


Jeffrey Boedges: Yeah.


Rick Kiley: How many times do people offer to pay you in product?


Tajanna Mallory: That has not happened.


Rick Kiley: Really? Okay.


Tajanna Mallory: Mostly because I’m not in a, first of all, I can’t pay my light bill on product.


Rick Kiley: No, of course not but I’m just saying…


Jeffrey Boedges: Yeah. You’re in Florida.


Rick Kiley: You’re always going to say no. I, of course, would say no too but how many people offered. That’s my question.


Tajanna Mallory: Not that many, actually.


Rick Kiley: All right.


Tajanna Mallory: Well, also, it’s probably because I’m in Florida. Maybe if I were in like California or whatnot.


Jeffrey Boedges: We can go down to Ybor City and make some money on a Friday night. I’m just saying. Just keep that in mind.


Rick Kiley: Yeah. Well, it’s funny…


Jeffrey Boedges: That place is crazy.


Rick Kiley: When you were talking at the beginning, I had this idea of like a Dave Chappelle or Judd Apatow comedy where you were like the executive assistant, but they all started asking you to like deliver weed to people on the side. And that’s how you got in the industry as just an alternative story for you, if you want to run with it.


Tajanna Mallory: That might be a good one, actually.


Rick Kiley: Yeah. And it’s just like, “Wow. Now, I’m going to start.” Like, think about Michael J. Fox’s Secret of my Success combined with like one of these other movies and I think you got like a script on there. I can see the pitch.


Tajanna Mallory: Well, I will tell you. If any producer wants to reach out to me about starting a reality show of assistants in this industry, I got some stories for days.


Rick Kiley: Oh, man.


Jeffrey Boedges: Oh, wow. I like that.


Tajanna Mallory: And I can tell you that I have – but honestly, I have stories for days about working as an assistant in like corporate America.


Rick Kiley: I’m sure. The stories are always crazy. Executive assistant stories are nuts.


Jeffrey Boedges: Yeah.


Rick Kiley: Ask me to drive to the car wash with the bag of money, turn around three times, and then walk away. And when I got home, I had a fresh bottle of $250 tequila. I don’t know. Like, there’s weird stuff that happens.


Tajanna Mallory: Do you guys watch Succession? Have you seen Succession at all?


Rick Kiley: Oh, yeah.


Jeffrey Boedges: It looks too creepy for me. It scares me.


Rick Kiley: There’s just no one likable in the show. That’s the problem.


Tajanna Mallory: I’ve never considered that until you said it. You’re right. There is nobody likable on the show but somebody cannot stop watching it. But do you know who my favorite characters are? The assistants. If you watch the show again, pay attention to the assistants and like the number of things that they take those women through, I’m just like, “Oh, my God.” Like, literally, I don’t want to give away too much of the show but the things that they have seen on the show.


Jeffrey Boedges: Yeah. There’s probably a few shows because I think Mad Men, the assistants also really had a rough ride.


Tajanna Mallory: I haven’t seen that one but I should start that because I’ve heard that the assistants have an important role.


Rick Kiley: Yeah.


Jeffrey Boedges: And they’re always, yes. Well, they’re usually kind of like kind of pulling the strings which we always joke about with our own folks. We know who’s really running the shop.


Tajanna Mallory: Exactly.


Rick Kiley: All right. Let’s get back on track here because we’re coming near the end of time. I got a couple more questions. I think you talked about this a little bit but I was curious about the career path of people who are virtual assistants. And so, you clarified some of this that most people are like running their own business. Ultimately, for most people, is that the aspiration that they themselves are entrepreneurially minded? They’re going to start and their own business will flourish? Is there anyone who you think is looking to like become the executive assistant to the CEO of like one of the largest cannabis companies in the world? Like, what’s the path?


Tajanna Mallory: Unheard of any of those passions coming through yet where people are like, “My primary goal in life is to be this.” I think that similar to myself, by default, I think a lot of people have come into the role of being a business owner as a virtual assistant because what they wanted out of their career didn’t exist either with the company they were with or on the path that they were on. So, really the trajectory is different for everyone. A virtual assistant who primarily works with like YouTube or social media channels, they might have a goal of having a cannabis marketing agency. I talked to another woman and she was passionate about cannabis, could do administrative work but she actually wanted to be a doula, so she was kind of also going through training for that. So, really, it just kind of depends. A lot of different people have different aspirations, this might just be a check stop for them kind of along the way. They might need, you know, I have an assistant who, literally an assistant on our team, she is in an RV like her and her family sold their home, and they’ve been moving around in an RV for I think almost a year. And she homeschools her kids and she also does administrative support for one of our clients in the PR space. So, it’s just different for different people of what their goals are in doing this work.


Jeffrey Boedges: That’s my goal. That one you just said, the RV.


Tajanna Mallory: Just bring in an RV.


Jeffrey Boedges: Yeah. Just driving around.


Rick Kiley: Or maybe making deliveries along the way too.


Jeffrey Boedges: Getting an adventure.


Tajanna Mallory: Awesome too. She’s so good. Half the time I’m like, “You’d be in what? You guys were driving from Wisconsin to Colorado? What? And you were working all the time like wow.” But, yeah, they’re great. So, everyone has a different goal about what it is that they want to do. Some people start off doing this and eventually just want to learn as much about the industry as they can to move into a corporate position. But they need help identifying what that is. So, they want to come into the industry and start working, bringing their skills, and they’re scoping it out. Either way, my goal is to help you be better than you were before you came to us. So, yeah, obviously we need you to bring some skills because we have clients that we want to work with them and partner with them and help them but I also want to help people achieve their goals in this industry.


Jeffrey Boedges: That’s great. That’s very noble. Yes.


Rick Kiley: Yeah. And then ultimately, what’s next for you? You’re going to continue to grow this business? World domination? Like what’s the endgame here?


Jeffrey Boedges: Secretly controlling the entire cannabis industry in the States.


Tajanna Mallory: Behind the scenes.


Rick Kiley: Yeah. You want to be the puppet master for all the Fortune 500 CEOs you can or…


Tajanna Mallory: That would be – and then it’s like a secret tribe of us like a secret…


Jeffrey Boedges: See, this is where the movie gets interesting. It’s like it goes from being kind of like a comedy to being like when you’re like the dark lord of cannabis.


Rick Kiley: Yeah, but was it your idea for Elon Musk to buy Twitter? Is that how that happened?


Tajanna Mallory: That was actually not my idea. I would have preferred for him to write me a check, but that would have been something more along the lines of what I suggested. You know, it’s so funny you say that because we already kind of have that a little bit like some of our assistants helping other assistants. And so, we don’t always like tell clients who some of our other clients are. And so, we kind of get behind the scenes on Slack and I’m like, “Hey, I’m on this call and so-and-so is trying to reach your guy. Like, are they available on Tuesday? And if they are, let me just throw it out there.” So, we do a lot of that kind of puppet mastery behind the scenes already, which we love. And we do want to continue to collaborate together in that way to be able to continuously support and be a resource on the teams of some of these professionals. But for me specifically, I think I just want to continue to coach and train assistants, help them be as best that they can be.


I think the thing that set me apart and eventually my team, as I started to grow it and develop it, is the level of professionalism that we can also bring to this industry, right? So, yeah, as a business owner in the cannabis industry, you can light up on a call and be as high as you want to be knowing that your assistant is still running everything. And now you’re in your creative space to like talk about the next business development idea that you have and you’re not worried about it. So, those are the kind of things that we want to keep doing.


Jeffrey Boedges: Sorry. I cut you off, Tajanna. Go ahead.


Tajanna Mallory: No, you’re fine.


Jeffrey Boedges: Yeah. I was going to say that part about being able to light up on a call is I remember like when I’m old enough to have gone in an interview at Marlboro out of college at Philip Morris and I remember, yeah, we were smoking cigarettes in the interview. That was bizarre. But in wine and spirits, I can honestly say I don’t know that I’ve been to a lot of meetings where somebody cracks open a bottle of scotch during the meeting. It’s like, “You know, I’m going to go ahead and have a couple of fingers of this during the meeting.” It’s different.


Rick Kiley: Yeah. But what’s interesting, I don’t know, but I bet the executive assistant dynamic, there’s probably a lot of consumption behavior that happens in the person that they’re assisting. And at least just in this industry, it’s just out there and in the open.


Jeffrey Boedges: Yeah.


Tajanna Mallory: I would agree with that. I will say to you, though, this industry is very different and it’s not just different in like the way we operate kind of like perfect “professional etiquette.” It’s different in the way we do business. I mean, I’ve seen people in cargo shorts and flip-flops in like the cheesiest cannabis socks do multimillion-dollar deals and you’re just like, “That guy? Like seriously?” So, you know, this industry you can’t like when they say, “Don’t judge a book by its cover,” I think this is especially true in this industry.


Rick Kiley: Right.


Tajanna Mallory: And so, I come from corporate America. So, some things are just habits that are hard for me to break. I was just recently at the Benzinga Conference and I like try my hardest and I was glad I did this particular day because that’s the capital conference. So, a lot of those guys came in suits and they were a little bit dressed more professionally. But any cannabis company I’m going to, I generally have on a blazer. And I have felt so out of place. Every single conference that I’ve gone to, I’m like, “You were just really dressed up here for no reason.” And similar, it was less at Benzinga but, overall, the whole culture of this industry is just totally different.


Jeffrey Boedges: We should get you a blazer with like a lot of little canna plants on there and it would be subtle, but still stylish.


Tajanna Mallory: It would be subtle but maybe I should just wear those cheesy cannabis socks so I can do multi-million-dollar deals.


Rick Kiley: Yeah. Go full-on something. Yeah. Go full-on something. That would be great.


Tajanna Mallory: Yeah.


Rick Kiley: Spectacular. So, if someone because they need a CannAssistant wants to reach out to you, how best should they go about finding you?


Tajanna Mallory: You can email me at tajanna@cannassistants.com. You can visit our website,  CannAssistants.com. You can find me on Instagram @iamtajanna, LinkedIn, Facebook, CannAssistants, all the things. We’re where all the cool kids are except TikTok.


Rick Kiley: Wait. There are no cool kids on TikTok or you’re just not…?


Tajanna Mallory: I said we’re where all the cool – I’m not on TikTok.


Rick Kiley: Oh, got it, got it, got it. I was like…


Jeffrey Boedges: Yeah. That’s when we start doing like the secret confessions of assistants. That’s where that goes.


Tajanna Mallory: You know, that would be a good series. Actually, let me write that down.


Jeffrey Boedges: We usually give away free really moneymaking idea.


Rick Kiley: The other like you were talking about the assistants who pull the strings, I was thinking they are like the Illuminati. You could call them like the Assistanati.


Jeffrey Boedges: Oh. That’s good.


Rick Kiley: Just do it.


Tajanna Mallory: Assistanati.


Jeffrey Boedges: Yeah. That is good, Rick. I like that. And you would talk about a team-building thing. Like, if you want to join, you got to be an Assistanati.


Tajanna Mallory: Yeah. We are about to launch a – I’m actually working on launching a CannAssistants community and we will have a lot of powwows like that.


Jeffrey Boedges: Don’t forget to invite your friends who are on the ancillary. Yeah.


Rick Kiley: That’s really cool. Well, listen, we’re at the end of our time here. One question we close with and I’m not sure how close you are to this but we are sort of loosely charting cannabis’s march toward federal legalization. We’re curious if you have any thoughts on when you feel it might be legal federally or even in Florida.


Jeffrey Boedges: When can I buy in Florida?


Rick Kiley: What’s the deal in Florida? Is it ever going to be legal in Florida?


Tajanna Mallory: Florida’s medical. I feel like, you know, how we have like the Florida Man headline like I think it’s going to start coming into like the Florida cannabis like constantly on a headline. Florida, honestly, I feel like recreation or adult use is going to I would say here in Florida, we’ll give it the next 2 to 4 years or at least I’m crossing my fingers. And I would say federally, I don’t think it’s going to be the next term.


Rick Kiley: Okay.


Tajanna Mallory: Maybe the following, depending on who’s in charge, depending on what’s happening. But I don’t know when. I’m just saying it’s not going to be next term. That’s not in the next four years or whatever number we’re on.


Jeffrey Boedges: Right. Okay, cool. Well, we got you on the big board. The winner gets a free trip to, you know.


Rick Kiley: Yeah. We’ll see what comes first. We hire your virtual assistant company or cannabis is federally legalized. I’m willing to bet it’s the former. So, Tajanna, it was really nice speaking with you today. It sounds like you have a great thing going on.


Tajanna Mallory: Thank you for having me.


Rick Kiley: Love hearing from you. A lot of fun. We’ll talk to you soon.


Tajanna Mallory: Thank you so much.



Scroll to Top