Interview With Ashley Verrill

Man I’m pumped to introduce you guys to one of the most bad ass chicas I’ve ever had the pleasure of meeting. She is a REAL, live, completely self-made CEO of an international events & entertainment company…sorry friends just calling yourself a CEO, does not actually make you one. She’s an unbelievably creative artist who just recently started putting her paintings out there for the world to see. We met wayyyyy back in another time and world, of 2001 when we were both in high school, and strangely haven’t seen each other since. Our friendship blossomed about 9 years ago with a random message to her when she asked about help with her business…it was a simple solution from me, and since then she’s become one of my go-to business friends. We’ve hit many of the same roadblocks in business and personal life and live by many of the same moral and ethics codes…she’s obviously much more saintly than I am though lol. 

I’d like everyone to meet Ashley Verrill, CEO of After Dark Events & Entertainment. Thanks so much for taking a little time to switch from us talking on Facebook to us talking through email Ash! Why don’t we just kinda start with your initial journey into entrepreneurship and being a business owner, and eventually becoming a CEO. 

Hi Nick! I’m honored that you reached out to have this chat. We’ve certainly seen each other through some crazy professional adventures (and life adventures too)! I’d love to elaborate a bit on my journey and my road to entrepreneurship.

Since we’re throwing it so far back to when we officially met, I feel like even as early as high school, I’ve always been someone who loathed being told what to do. I rejected the whole notion of “taking orders” from someone above me, especially if I could see a better way of doing things. At that time, it reflected in my competitive cheerleading career and come to find out, it later spilled over into my professional career in a big way.

So, where to start? Directly out of college I moved from Buffalo NY to Baltimore MD to work as a Regional Manager for a travel agency in the area. That same year, as a result of hard work and a very high sales volume from my cubicle, I was promoted to become the Program Director for their Cancun student travel program. I traveled to Mexico regularly, and during my time there I saw the opportunity for significant growth within the agency I was working for. There was a white space that hadn’t yet been filled in the event industry and it just seemed like the obvious next step. When I pitched my idea to my boss at the time, I specifically remember him blatantly laughing in my face. Within seven days, I had quit my job, sublet my apartment, and moved to Mexico to see if I could fill in that white space myself… fast forward a couple months, I did it!

Needless to say, I learned rather quickly that I was not meant to work for someone else. I wanted my potential for success to be in my own hands. I wanted to motivate myself and answer to only myself. My goal was to create a career that allowed me to LIVE my life every day however I chose to. So, yes, I left my 9AM-5PM grind living as a young professional in the US and ran away to Mexico where I spent the next six years of my life becoming fluent in Spanish, learning huge life lessons, and building my professional empire. I am now a proudly bi-lingual entrepreneur, a business owner and the CEO of my own LLC.

I appreciate you mentioning my art as well! That journey came as my “pivot” when the pandemic temporarily shut down travel and I needed to find a way to sustain my overhead and keep myself sane. I am technically trained and hold a Bachelor’s Degree in Fine Art but before this year, I would simply paint to fill my empty walls. Whenever friends or family would see my artwork, they would ask when I was going to start selling it. My answer was always that I was too busy I didn’t have enough hours in the day (as any fellow entrepreneur can relate to). Well, as you may have heard time and time again, life is too damn short, so I took a really difficult time and tried to find an opportunity in it. Travel is coming back now and I’m so grateful but as a result of the insanity that was 2020, I also see how important it is to diversify your streams of income because someday the rug can be swept from under you and you’ll need to flex to survive. Just one of life’s many lessons I hold near and dear!

Aww I’m not sure anyone’s ever used honored to describe anything to do with me lol. It’s interesting to see how people’s journey’s really do tend to parallel each other. We face so many of the same challenges just disguised differently to one another.
Loathing being told what to do is a common trait amongst us entrepreneurs…I think a lot of people struggle and bounce around jobs because they’re entrepreneurs at heart. I’ve also known you long enough to know that you do often find a better way of doing things, it’s helped get you where you are now. 

I used to think of myself as a control freak. My Mom often called me a “bull in a china closet” growing up and man, how that would offend me. Now, I see that it is actually a positive trait. Yes, I have a presence. I’m not shy or quiet. You know when I’m in the room. I don’t let things happen TO me, rather I take hold of the reigns and manage to navigate the path myself. Love it or hate it, I’m better for it and I attribute a lot of my success to crashing into a few walls on my way out the door.

I actually think the “control” thing is just all part of the entrepreneurial personality. Fear of the unknown or lack of control in a situation was always a driving factor of my anxiety…but I’ve taken that same exact mindset of not letting things “happen” to me anymore. Shit happens to everyone, honestly I think if we each delved deep into one another’s stories across the board we’d find a lot of similarities in situations and feelings attached to them. It’s the reaction that separates the helpless, from the good, from the great, from the unstoppable. I recall us both going through similar personal issues back in the day and I really drew strength from the way you approached it rather than the way I was approaching it. I realized looking back I made myself a victim when really, plenty of other people have been in similar situations and came out on top…why couldn’t I?

I think all entrepreneurs (even those that don’t know they’re entrepreneurs yet) have that similar mindset. You must have it in you to take the leap, risk it all, self-reflect, accept defeat and get up kicking and clawing until you ultimately have a breakthrough. Once you’ve “made it” you’ll probably fail again…. and again… but those lessons are the most important ones. You cannot control what happens around you, but you CAN control your reaction to it, and THAT my friend is an important thing to remember. Fail your way right to the top and keep on keepin’ on!

And wow, to be laughed at by a superior for an idea could have easily derailed your entire career…instead it fueled an entire life for you. 

Moments like that are hard, they’re embarrassing, and it would be easy to bow your head and let it defeat you. He will never know how pivotal that moment was to me. Publicly laughed me right out of his office and into a new adventure that I’d later be forever grateful for.

It’s quite the amazing story to go from little Oriskany to turning your life upside down in a different country. We’re you on your own at that point in your life, where it was a “simple” decision to just say, screw it, I believe in myself enough to give this a shot? It’s funny to hear some people say they “can’t” do something like start a business when there’s plenty of proof in people like you that have thrived after dumping the 9-5 life. 

I was on my own. I had no strings attached to where I was living, or anywhere really at that time. I can’t say it was necessarily a “simple” decision to have left my country and taken on that kind of risk with literally no money, but I remember that I didn’t hesitate. I was so busy DOING that I didn’t question myself once. I was fearless at that time in life. Maybe it was confidence, maybe it was ignorance? I’m not sure but I’m certainly glad I did it!

Well I put “simple” in quotes for that exact reason…no strings attached, no other humans feelings or life to worry about at that time. It was sort of the perfect storm to be able to follow your dream at that time. And isn’t it funny how confidence/ignorance can sometimes be interchangeable? haha. They say “ignorance is bliss” for a reason. How did others in your life react to your relatively split second decision to dump the life as you knew and become Mexicana? Parents, close friends, other family members? We’re they extremely supportive or did they think you were out of your mind?

That’s a great question. I think at first, the person I was most nervous to tell was my Dad, but not very surprisingly, he was SO SUPPORTIVE. He shared with me that ever since I was little,  growing up in a cushy comfortable life in my small hometown of Oriskany NY, he would worry that I may not branch out… see new places… make myself uncomfortable in order to push myself.. yet there I was saying “hey Dad, I think I’m going to move to Mexico in a few days and try and start this ambitious business.”. He basically said; Do it, you have nothing to lose and everything to gain. He was right. My Mom and Dad both work for the airlines and they’ve always traveled for a living, so I don’t think it was as big of a deal to them as it would be to most parents.

As far as my friends go, mostly supportive, some judged and talked about me behind my back (those ones are no longer friends, because real friends don’t do that to you). The thing is, I didn’t give myself time to care what anyone thought. I just went full speed ahead and somehow landed on my feet. This kind of move weeds out the toxic people in your life. As a result, the friends I hold near and dear to date are THE BEST. I only surround myself with those who uplift me, and I return the favor unconditionally.

So when you say you “did it” by filling that white space, what exactly are you referring to? And obviously this didn’t come without fighting tooth and nail with giant competitors, and my favorite, unscrupulous Mexicans who thought they could pull one over on the tall blonde American girl…. oh little did they know hahaha. Like bringing a knife to a gun fight. Some of my favorite stories involve some speaking Spanish under their breath to you and you bust out the fluent Español! Did you naturally have the confidence to deal with these types of people and companies or is it something you built along the way? 

Well, when I arrived in Cancun, I remember I had $740 dollars in my pocket from my last tax returns. I had no idea where to start. I mean hell, I went to art school and there I was trying to start an international event agency with zero capital to invest. I used my contacts to find leads who would produce a customer base and eventually I formed a relationship with a small travel agency in Canada, then another small travel agency in France, etc. They would send me their Cancun travelers and I would set them up at the clubs. After a few solid months and a heap of positive reviews, word spread and I began generating my own direct client base.  

You’re right that the Mexico side of it was a bit trickier. Luckily, I had contacts in place from my previous time spent in Cancun so I knew who I needed to talk to in order to secure working contracts at all the major venues. That said, knowing who they are and getting an actual sit-down meeting with them are two different stories. Back at that time, Mexico was (and still is in a lot of ways) full of that macho sexist mindset where women “can’t be” leaders, “can’t” run businesses and “don’t deserve” the same respect professionally. There was one Director of Sales specifically that refused to meet with me. He happened to run the accounts for the biggest clubs in the entire city of Cancun so I had to find a way. After weeks of reaching out the old-fashioned way and being snubbed, I decided I would sit outside of his office and wait until it was time for him to leave for lunch. Eventually he came out and on his way to his car, I forced our first meeting as I trailed behind him not taking no for an answer. It wasn’t as easy for him to say no to my face, so I got the sit down and ultimately made the deal. To be honest, I look back at that moment and I think “How in the actual hell did you find the nerve to sit outside that man’s office uninvited? How did you have the balls to follow him until he agreed to meet with you? You’re a crazy woman, woman!” Full disclosure, 10 years later and he still looks the other way when I walk by, but I now run one of the most well-known vacation event agencies in Cancun, Puerto Vallarta and Cabo San Lucas so it is what it is. Don’t let one single person road block your success, no matter how hard they try.

That story is freakin fantastic and I’m picturing the movie….he looks like Pablo Escobar

Who is playing Ashley in the biography of your life? He comes out of his office and there’s this tall blonde American girl speaking Spanish, asking him if he’d like to extend his car warranty. Can you remember the exact conversation you had with him? This is sales(wo)manship at it’s finest. You used the regular channels of communication, and being ignored certainly isn’t a “No”, at least not in my book haha, so you just randomly show up at his office. Did he have a secretary at the time? 

He did have a secretary, two actually, but there was a glass wall separating them from me. When I walked up there was randomly a single chair sitting outside, so I planted myself there and what I do remember like it was yesterday are the nerves I had in the pit of my stomach sitting there and waiting for my moment.  

To answer your question, if anyone is playing me, I’d like it to be Blake Lively because #GOALS.

And aren’t those feelings in your stomach crazy when you’re doing this for yourself? Like you could puke but would totally do it again like a rush of adrenaline.

We often hold ourselves back because of that pit in our stomach but we shouldn’t let it stop us. How will you grow if you don’t make yourself uncomfortable? The simple answer is you won’t. Butterflies are a positive thing when it comes to your love life, right? What makes your professional life any different?

People have a much more difficult time ignoring someone in person than they do through email or phone calls. Sometimes it’s just that next step you have to take in sales to get what you need/want. When I have people ask me, how do I get more sales, or more often it’s someone just starting off and asking how do I get sales…I’ll tell them, I literally make a list of close to 100 people and I then message them…people balk at the idea. I think back to when I started at the tv station, which was only 10 years ago now, and I was going through the PHONE BOOK to make a list of prospects that I would then DRIVE TO in my suit and tie and drop off a business card…..that entire friggin sentence is dated and disgusting to me lol. So I can empathize with you sitting outside an office and waiting for someone to be there…however not in a foreign country where I was also looked down upon because of my gender haha. 

When you first started did you use your ex boss as a motivating force? I know when I first started out so much of my motivation came from wanting to simply prove my previous employer wrong about firing me years back. I don’t think it’s motivation that can be sustained long term because if you reach beyond what they’ve done, now you need to find new motivation…but I feel like a lot of business ideas are born out of “pain” or trauma and the feeling of “what do I have to lose?” 

YES, I did. Gotta love that revenge-driven success. My favorite moments in the beginning were when the same guy that laughed me out of his office traveled down to Mexico and saw my team (which was often bigger than his own) manning our section full of happy clients at the clubs. I couldn’t care less about him now but you’re right, that is the beauty of it. His mockery drove me to prove him wrong. Once I did, and once I saw how incredible my business, and quite honestly entire lifestyle, had become as a result, I look back at the once mortifying moment with gratitude and amusement.

And Blake is a lovely choice. Love her in Accepted and Savages!

Blake Lively's Preserve: An Obituary | Vanity FairMay be an image of 1 person

She’s such a boss, isn’t she? On an unrelated note, I’d also love to own her shoe collection… hey, a girl can dream.Blake Lively Shoe Collection news | Glamour UK

I think your art is a super important part of your journey…a passion that you were more or less nervous to unveil, but 2020 with another example of, sorry about your plans, butttt how well can you adjust type moment.  You took the pivot as gracefully as you could and tried to turn things into a positive. Of course 2020 is difficult to look at as a whole from a positive perspective, I think it helped people find new ideas to survive. And you’re absolutely right, it’s those streams of income that differentiate you from most of our peers. I learned growing up, you got a job and you just lived. Wasn’t until a few years ago I learned that those little streams of income, tend to lead to even bigger bodies of water. 
With travel coming back, what’s your focus on now? After Dark had started to make great progress in Cancun and you also added Cabo and Puerto Vallarta to destinations you can provide entertainment option to guests…Will you continue growing that while also building out your new venture? 

That’s right. 2020 taught me a lot. It was NOT easy to accept that my bread and butter business was going to suffer for a bit and there was very little I could do about it. Depending

 on the government (barf) to assist to keep my doors open wasn’t going to do it, but neither was accepting my role as a “victim” in the situation.  So, I used the time as wisely as I could. I spent a great deal of time enhancing After Dark’s website and beefing up our offers for when travel started to thrive again. I also began to monetize my artwork and my husband and I dove into real estate investing a bit! To answer your question, yes! I have an awesome team working alongside me, specifically my incredible assistant, and as a result of that I have full confidence that I can continue to do it all. Who needs sleep, anyway right?   

I think you prove a great point with what I’ve seen from most of my clients and friends is that the “unstoppable” ones took 2020 and went with the flow. Every single person in 2020 could have easily found a reason to be a victim or to take the year off or to blame someone else. People I look up to all took the appropriate amount of time to “grieve” the loss of the lives we had prior to the pandemic and then adjusted. The ones that stood by waiting for the government or for help from outside sources, floundered or failed. I will never forgive any government that forced small businesses to completely shut down operations without fully compensating them. The big corporate companies were allowed to remain running while the smaller folks struggled, that part was horribly mismanaged and crushed millions of people’s dreams. How long into 2020 did it take you to say, ok the realist in me says, yup this is going to suck, but what now? I think I was in a fog for about 3-4 weeks of the shut down until my mind finally decided that this is gonna go for a while, it’s time to figure out a plan of attack for not only myself, but for clients too.

Man, it’s so true. It took me about 8 weeks if I’m being totally honest. I felt really sorry for myself for a hot minute. Then I tried the optimistic mindset; “This will be over soon”. When it turned political and I saw the world go into an actual uproar, I buckled in for the long haul. I knew we were in for a bumpy ride. I just didn’t know how bumpy it would get. So much to unpack there…. but I digress. A topic for another day, I suppose..

I think we could talk 2020 for hours on end, from benign to the crazy, but I want people to understand that the initial trauma was certainly common for many people, but again it came down completely to reaction! First way didn’t work, next way nope, finally the realist in you sets in and you turn to problem solving. 

Our world is always changing. We’ll never be able to stop flexing and 2020 showed us this hard and fast. Stay ready. Stay on your toes. Have a plan, and a backup plan, and a backup plan for your backup plan.

I’m grateful to have learned about passive income and how to make money from the online space as it’s become the necessity rather than the option now. Building up all these revenue streams is truly the only way to become wealthy. How many different revenue streams have you opened for yourself now? Obviously you have After Dark, your paintings, expand a little on your real estate stuff (are you buying and flipping, leasing, air b&b’ing)? Do you do any investing in stocks or cryptocurrencies? I used to think growing up, that’s all you needed to live was a “job”, but life is really changing for many, and it has been for a long time. The pandemic I believe is going to speed along automation, robotics, and AI and even more people are going to lose their “job”, so I think it’s good to see what other successful people are doing to sort of safeguard themselves from any kind of repeat of 2020. Some of my passive income involves starting my online shop through Zazzle, setting up a partnership with an IT company to handle client hosting and I get a percentage from them. I do affiliate sales through Utica Hemp and receive 15% from them for sales I generate. My crypto portfolio is up over 50% since starting. My goal is to never let anything in life crush me to the point of business non-existence, or to be too reliant on one source. 

Well, After Dark is now in Cancun, Cabo and Puerto Vallarta. I also recently started another branch of the business called The Trip Planning Experts. I’ve hand-picked some amazing team members from my After Dark crew and we now offer full fledge trip and event planning with a focus on celebrations within the US. The world hasn’t haulted, people are still having huge life events and they deserve to be honored. So, whether it’s a bachelor or bachelorette party, a weekend road trip, a full-on wedding or even a small baby shower in their own backyard, we take it on and make it unique, creative and unforgettable. I actually get incredibly excited whenever I am working on anything related to The Trip Planning Experts because this is where I thrive. I love planning the perfect getaway or an event that people will talk about for years to come. I could ride that wave all day and night!

Outside of the tourism and event space, I have my artwork, real estate and diversified investments. I haven’t jumped on the crypto currency train but I’m so glad to hear that it has been successful for you! There is no one size fits all when it comes to investing, I just do what works for me based on my circumstances. For those reading, Dave Ramsey is a great starting point for someone looking to invest for the first time.

I agree with you whole heartedly that passive income is the real MVP, which brings me to real estate. Long story short, my husband and I bought our first home when we moved in together in Florida and when we moved to Texas this year, we decided to try out the short-term vacation rental strategy with our Florida home. There are so many ways to invest in real estate. Everything from REITs to BRRRs, to flips and the list goes on. Real estate is not a get rich quick investment, trust me. It takes time and patience and as fun as it can look on HGTV, my best advice is to tread lightly, talk to other people who have done it before you and don’t over-extend yourself. The guys at Bigger Pockets have some awesome, easy to digest podcasts that really take away the intimidation that comes with the world of real estate!

Real estate is one of the initial passive income thoughts people pursue as it’s one of the most trusted and you can become quite wealthy…but boy that doesn’t come without risk and annoyances haha. Other passive income ideas to pursue for people include writing ebooks, teaching an online course, selling your knowledge or experience in any number of ways. Is there a way people are able to book your place in Pensacola? 

Sure is! Linking here: – Pensacola is an incredible hidden gem on the emerald coast of Florida’s panhandle. The beaches have been voted #1 in the entire US and Downtown Pensacola literally has something for everyone; from history to shopping to local cafes, restaurants and bars galore!

I’ve learned a whole lot in the last 8 years working with business owners and deep down were all so similar. I’ve attributed so much of my growth recently to reading self help and entrepreneurs books along with listening to a couple of great podcasts, The Mike Dillard podcast and RealAF with Andy frisella which used to be the MFCEO…hearing stories from truly successful people and how much their stories and struggles mirrored my own, that really helped guide me more towards helping others. Helping others is one thing I can fully control and it almost always makes me feel better. 

I’m the same way, I’ve finally reached that comfortable level with my decision that I look back at that time as a great experience that put me on the path that I am now. How could I possibly be angry anymore about it? Same for you, not like youd be angry and want to still work there. Success means not too much time for grudges and regrets. 

That initial fear of acceptance from whoever it is in your life also seems to be common. I remember telling my parents what I wanted to do basically with no notice. Said I want to quit the tv station and get back into doing graphic design. They were extremely supportive even though I’d be lying if I said there weren’t times of struggle where I was fairly asked if this was worth it…it is and always will be to me. 

Friends are difficult for sure. I’ve noticed that some people truly can’t understand just the mental toll business ownership takes on someone unless you do it. I’ve had a couple of different types of jobs. Hourly jobs, salary jobs, commission jobs…owning a business is something entirely different times 50 because not only do you have to strive to make sure your product or service that you specialize in is near perfect, you have to somehow learn alllllll the other aspects of owning a business. Your brain never stops. When 5pm rolls around I used to leave work at the office and fuck off. Now I still fuck off, but my mind is almost always in motion with ideas or song lyrics haha. It was hard to find genuine friendships with people that really understood everything I’m trying to do.

They say you are a product of the 5 people you surround yourself with most, so level up! Dream big, work hard and keep your circle dynamic!

You’ve taken a fantastic approach to this…you started off VERY micro in the sense that you gave people the perfect CANCUN vacation experience. Then you’ve slowy added new locations over the last few years and now opened up the opportunity to plan party trips for the entire US…that micro approach to JUST Cancun helped you really become a true expert in the nuances of travel and especially international travel, now outside of obtaining the audience, planning the trips opens you up to so much more…do you think if you had done this in reverse you’d have the same success or the macro approach to the entire country would have been harder? 

I tell people ALL THE TIME, do not rush your success. Start small, perfect what you do well and grow slowly. I wouldn’t have even known where to start if I did this in reverse. I saw the path for After Dark in Cancun, and I mastered that before expanding elsewhere. Now, I can confidently say no matter where you are going, I got you. My talented team and I will meet and exceed your wildest expectations. If you’re coming to Mexico, After Dark holds a five-star reputation for a reason: – If you’re looking to plan an amazing trip or unmatchable event in the US, we’ve truly earned our title of “planning experts” and we’re here to help you:  

I think we need to let folks know about your art and the types of pieces you’re looking to do for people. I’ve seen your simplistic woman themed art you’ve done and I think that can be a great idea to keep pushing for all the strong women friends out there. I’d love to help you get some more pieces to add to your collection! 

I appreciate it, Nick. Through my creative work, I hope to express empowerment, appreciation and feeling above all else. Emotion is what makes art powerful. If you profoundly feel my artwork, I’ve done my job as an artist. My website can be found here: and my Instagram here:

Ash I can’t thank you enough for taking some time to do this and help me build out my blog. Eventually a podcast will be born and I hope you’ll be one of my first guest so everyone can continue to follow along with your awesome journey. Can you drop some links to where people can reach you for any trip planning to Mexico or within the US now, commissioning you for art pieces or even ask you about your rental properties?  Rock on boss lady and keep kicking ass!

Thank you for having me. It’s always fun talking with you and I humbly hope my story can give someone the courage to take their own leap of faith. Consider me on standby for that podcast!

After Dark Events & Entertainment: /

The Trip Planning Experts:  /

ART by Ashley Verrill: /

AirBnb Pensacola Vacation Rental: