Crystal Esquivel and Alessandra Thomas are longtime executive assistants who co-founded the Cleverly newsletter, where they love to curate resources for the EA community, create tools and downloads to share, and encourage positive, confident workstyles.

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In this episode, Crystal and Alessandra share a bit about their experience as assistants and give us a glimpse of what it’s like to work as a team. Of course, they also let us know all about what Cleverly is!


No one is useless in this world who lightens the burdens of another.

– Charles Dickens

If you don’t ask, the answer is always no.

– Unknown

Crystal Esquivel and Alessandra Thomas

Alessandra started her career in finance, took a sharp right turn into non-profit fundraising, then decided to find a flexible role that played to her strengths and her love of setting others up for success. She entered the world of virtual EAs, where she hired, trained, and managed EAs at all levels and led a Client Success team.

She has since cultivated her own successful virtual EA business supporting incredible executives. Alessandra loves details, databases, and automations. She lives in Charlottesville, VA, where she, her husband, and her dog spend much of their time chasing their twin toddlers.


Crystal’s roles over the years have ranged from Director of Client Services to Chief of Staff, from Executive Assistant to Executive Producer—all with the common threads of mentorship, organization, and collaboration. She has organized and managed chefs, photographers, and cocktail experts, led weeklong food events in multiple cities, has authored two books, and now works directly with executives as a virtual EA.

Crystal loves helping others, all things food, and nerdy word puzzles. She lives in Austin, TX with her amazing husband and her little black cat.


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Crystal Esquivel 0:00
Hi, I’m Crystal Esquivel, and today’s leadership quote is, no one is useless in this world who lightens the burdens of another and Charles Dickens.

Alessandra Thomas 0:10
Hi, I’m Alessandra Thomas and today’s leadership quote is, if you don’t ask the answer is always no. Leader assistant podcast exists to encourage and challenge assistants to become confident, Game Changing leader assistant.

Jeremy Burrows 0:30
Hey friends, thanks for tuning in to Episode 139. You can check out the show notes at Before we jump into today’s interview, just wanted to encourage you to check out our upcoming live events. Some of them are online live and some of them are live in person, to check out the full schedule of events for Game Changing leader assistants like yourself, professional development, training and networking with executive assistants, chiefs of staff, administrative assistants, executive business partners, whatever your title is. If you are a growth minded leader, Assistant, we would love to have you join us at an upcoming event. So check out for the event schedule. And we will see you at a leader assistant live event soon. Hey friends, thanks for tuning in to The Leader Assistant Podcast. It’s your host Jeremy Burrows. And today I’m very excited to be speaking with Crystal Esquivel and Alessandra Thomas. They are the cofounders of cleverly, a workstyle newsletter for executive assistants, administrative assistants, and all the assistant leader assistants in the world. How’s it going crystal and Alessandra? Great.

Crystal Esquivel 1:58
Thanks so much for having us.

Jeremy Burrows 2:00
So let’s start with crystal. So crystal first. Welcome back to the show.

Crystal Esquivel 2:06
Thank you. Good to be back.

Jeremy Burrows 2:08
Can you catch us up on what’s happened since episode 12? I believe it was episode 12. We’re on in the hundreds now. We’re on episode 12.

Crystal Esquivel 2:18
That’s amazing. Yeah, so basically the pandemic happened. And I was working at a software company before with software for executive assistants. And as the pandemic hit, there were cuts made and my position was cut. So it was pretty bad timing, you know, to be without health insurance or a job. But thankfully, I have an amazing husband that helped me pull through it and really great friends. I got some picked up some EA clients from an agency that I worked with before. And those clients turned out to be really awesome. And we now work directly together. So now I have an EI client that I’ve had for so almost seven years now. And I’m also an executive producer of another podcast called outlier Academy. So kind of moving from one end to the other of EA and executive producer, and then co founding cleverly so definitely has been ups and downs, but it’s all up at the moment and just really grateful to be here.

Jeremy Burrows 3:24
That’s awesome. Well, what, uh, what can you tell us about the podcast that you’re part of?

Crystal Esquivel 3:30
So it is okay. It’s called outlier Academy. It is hosted by Daniel Scrivener Who is he has been CEO, a designer and investor. He’s done a little bit of everything. And he interviews other investors, founders, and just people who can give masterclass interviews on deep subjects. So, there’s a lot that I’ve learned about investing over the last year that I had no idea about before. But the part that I do is basically all of the operations. So it’s been just me and Daniel for a year now, I guess. And we just now hired like a social media person and a designer and an assistant. And yeah, so it’s growing. It’s it’s a lot of fun. It’s a weekly podcast, and it’s gonna grow into some membership and products and other things as well.

Jeremy Burrows 4:21
Nice. So do you think? Did you kind of get that opportunity through your Promote executive assistant work?

Crystal Esquivel 4:30
Yeah, it started with Daniel needing he wasn’t sure what he needed, I think. And so he kind of was like, Maybe I need EA help. And then it turned into how about this one project? And I think once he saw what I could do, was beyond just EA work. He kind of was like, Okay, let’s do something different. You know, here’s this podcast, I want to run. Can you create it and do it so and it turned out like it’s so much fun. It’s a lot of what an EA does anyway, but you know, it’s just Project Management almost like event management. So yeah.

Jeremy Burrows 5:05
Awesome. I love hearing stories about EAS kind of stepping in and taking their roles because they can like anything. Yeah. All right, well I’ll Sondra thanks for joining us. What part of the world are you in today?

Alessandra Thomas 5:22
So I am in Charlottesville, Virginia. But next week, I am moving to Austin, Texas. So Russell and I will be in the same city for the first time in our friendship. And we’re like, beyond excited for all the things so Austin meet up in the future.

Jeremy Burrows 5:43
Yeah. Sweet. Well, Austin is the place to be apparently, so. So tell us a little bit about your career. And kind of how you transitioned or ended up as an executive assistant.

Alessandra Thomas 5:55
Yeah. So I’ve had a lot of jobs, we’ve moved a lot. Since I graduated from college a long time ago, and a lot of jobs doing a lot of different things. It’s been a very windy path. I started my career in finance, actually, and then moved into nonprofit fundraising. And I really noticed that the key thing I loved with those jobs was setting up others for success. So I loved the operations, the efficiency, the details, really making things happen. And I’d like to be the person on the team that everybody could count on to get stuff done, if there was a problem that needed to be solved. If there was, you know, the someone’s like, I need something done, and I can’t figure out how they could come to me, and they would know that it would happen. So we were prepping for, I guess our fourth or fifth move in like seven years. I knew I had to stop getting new jobs. Every time we moved, it was getting exhausting. And I wasn’t really growing. And so I decided to pivot into the virtual EAA space. And it has been, like a dream come true. It’s been the perfect job for us, we’ve continued to move a bunch and I’ve been a full time freelance EA since then, which has been great. And now that we’re moving to Austin, I don’t have to quit my job again. And I can just take my job with me. And I get to work with the best clients. I love getting to basically handpick the people that I work with.

Jeremy Burrows 7:31
So do you speak in a pan picking? Do you find your own clients?

Alessandra Thomas 7:36
I do. And Crystal and I often have conversations about how I could possibly take on more clients. Because, you know, one client refers to another person who refers another person. And next thing I know, I have, like seven or eight people who want EA support and I personally can’t do all of that. And crystal has to remind me that it’s okay to say no to certain opportunities, which is very helpful to have that person in your life. So I’ve been very lucky, it’s been very organic and referral based, which has been great. But it’s also allowed me to have opportunity to say no, if something wasn’t a good fit. So just as important as it is to interview for a job. You know, you’re also interviewing the people that you’re working with. And I’ve been able to, to navigate that pretty successfully, which feels like a dream.

Jeremy Burrows 8:30
That’s awesome. So okay, so this is questions for both of you. What’s one thing that excites you about the assistant profession?

Alessandra Thomas 8:40
Yeah. Okay, I’ll take this one. Um, so I’ve been thinking about this a lot, recently, and, you know, time and just came out with their most influential people. And you see write ups about amazing startups in TechCrunch. When you see people like Crystal’s client who runs a podcast, and all of those people on those magazine covers, and in the New York Times, articles, generally are supported by EAS like there’s usually someone behind the scenes who is making the big meetings happen, is reminding people to send thank you notes and follow up emails, planning the big events, organizing the catering, impressing the teams. And I think that’s really awesome that there are these secret superheroes who are working behind the scenes to get everything done and just make it look really, really effortless. And what a cool role to have. I think it’s extremely unique and in no other company. You know, is there this one person who basically makes all the magic happen?

Jeremy Burrows 9:52
Yes, I agree. I agree. That’s why I love being an assistant. Okay, so let’s talk about how you guys met and start with crystal, how did you meet in? What made you want to work with Alessandra?

Crystal Esquivel 10:08
Yeah, so we both went into actually, I went into the virtual EA world a little earlier and met at the agency that we worked at before. Eventually, I moved on. And Alessandra took my role, we both were Director of Client Success. And we loved mentoring other EAS, and just kind of providing that education and leadership for them. And then we both kind of went out on our own and found each other again, we’ve always kind of been friends, but hadn’t, you know, talked really, like often. And then we just found each other and became best friends again. And we’re constantly sharing with each other ideas and resources and things. And we just were like, Why? Why does Why isn’t this exist? And how about we create it and let’s just do this thing for fun together. And it’s, it was easy for me because when I first met Alessandra and saw how she was working with her client, I remember actually telling my husband like, this girl is amazing. Like, I’m gonna learn so much from her. And I’ve been an EA longer like she’s just amazing at what she does. It’s just she’s, she gets stuff done. And she pushes me to be more brave. I am the one who’s cautious and like, let’s slow down and let’s make it perfect. And Alessandra is like, let’s just do it. So it’s also really great in what we do. Because we before we started, I made a list of all the tasks that we thought we’d need to happen for cleverly, and which ones we loved and which ones we hated. And there was just a line down the middle, thank goodness that everything I loved and she didn’t and everything she loved. I didn’t. So it worked really well. She’s great at sales and networking at all of the partnerships. She likes numbers and I don’t so it’s it’s, it’s been a really great partnership. And she’s because she’s passionate about being NEA, it makes it really easy for us to come together and figure out what we want to send out each week. And also, she’s just a loyal friend. So it’s pretty easy to work with her.

Jeremy Burrows 12:14
Nice Alessandra. What’s one of your favorite parts about working with crystal?

Alessandra Thomas 12:18
This is like a giant love fest. This is great. Yeah, Crystal, man. She’s just really, really, really thoughtful. Like, when people talking about being an empath. Krystal like truly is that person, she just really cares about her clients and the people around her. And so I know that if she’s going to do something and say, Yes, she’s going all in 100%, which has made it really fun and easy to work together. Because we’re both committed to what we’re doing and pretty honest about where we’re at with it. And as Crystal mentioned, I’m very like, let’s just do it. Let’s go, go, go. Let’s try this. Let’s put this out there. Let’s see what happens. And crystals like, Okay, I like it. But let’s, let’s like think about this for a second, let’s make it look really good. Let’s proofread it, let’s double check, which has been helpful because we are really trying to make cleverly something special and create a really curated brand that we felt really proud of. And so having crystals, you know, I for design and and the cohesive brand and cohesive picture has just been awesome. I’m not that person crystals, right? I’m, I’m the one who manages like the Excel spreadsheets and the automations and the data. And so it’s really helpful to have that design person. I think doing this alone would wouldn’t be impossible in our scenario. And just as Crystal said on top of that she’s just a really fun and amazing person. I’m going to plug her cooking stories on Instagram that she used to do all the time, during the pandemic. She’s the most soothing voice. So if you ever need to go back and watch her old Instagram Stories of her cooking live in her kitchen, it’s incredible. And I just love that we get to basically talk every day. We never run out of things to talk about which that’s a pretty unique scenario.

Jeremy Burrows 14:19
Yeah, sounds like a great friendship and great partnership. So tell us about cleverly. What’s the what’s the elevator pitch? What is cleverly and what how did you come up with that name?

Crystal Esquivel 14:31
Yeah, so the name oh my gosh, we had so many possible names. And I think Alessandra just kind of threw this on there. And we both liked it. And then we looked up, you know, what could we get as far as URLs and, and user names and that worked out really well. And we just felt like, every time we thought of the word clever, it was like it’s something you know, you hope someone says to you like oh, that was so clever. And then like, we like foxes, Clever Fox it just all kind of fits so cleverly at the moment is a workstyle brand basically focused on executive assistants and the general admin world, because that’s our knowledge base. And that’s what we like to talk about. So we have a weekly newsletter that goes out every Thursday, and it has helpful links and reviews of tools and apps, any new products that we come across, we feature workstyles of EAs including Jeremy’s thank you so much. We share work music playlists, we have free downloads every month. And so the newsletter is just basically all the things we want to share and create jammed into a newsletter and sent out every week. We also share tips and tricks on our social media, we have a small Etsy shop with some downloads and wallpapers and printables that we’re adding to. So as far as what it is, it’s what we’ve kind of told each other is we do whatever we want. When we want, we make the rules and we just figure it out. This sounds fun this month, let’s make that and share it. And it’s kind of just a way for us to share all the things in our brain with people who understand and have the same kind of mindset that we do.

Jeremy Burrows 16:15
Awesome. Alessandra, did you want to share like your elevator pitch your version of it? Or did she pretty much crystal pretty much take care of it?

Alessandra Thomas 16:23
Yeah, I think I think Crystal covered a lot of it. Just wanted to have everything that we learned in one place. And also, every time someone asks me for like, my favorite tool, or my favorite, whatever, I can just send them to cleverly, which

Jeremy Burrows 16:37
is great. Yeah. Okay, so what’s your three year plan? For cleverly?

Alessandra Thomas 16:46
So Chris, and I were joking about this, leading up to our conversation today, because sometimes we feel like we barely have a one month plan happening. Because we both worked full time as well as EAS, there’s a lot of fringe time for cleverly, which is both good and can be a little bit stressful. But when we sat down and originally planned the ideas that we had, we knew we wanted it to be something really big and great. So our main focus for the next year or two is really to grow the newsletter and the community. So be providing content that is useful and helpful. It isn’t just like being mailed in. And then we have a lot of ideas for the future. We wanted to continue to grow the Etsy shop and have more things that you can purchase both downloads, and physical products. So things that, you know, we’ve searched for that we haven’t been able to find the perfect thing, the perfect planner, the perfect pen, the perfect notepad, maybe we’ll get to make that someday. Maybe we’ll dabble in courses or memberships. But I think the biggest thing is getting feedback from the cleverly community and from our readers to help shape what they need. Because ultimately, we can make a lot of different stuff. But we want to make something that everyone feels like is useful, versus just something that we think is cool.

Jeremy Burrows 18:18
So crystal, there are a lot of assistant resources out there assistant, you know, maybe email this or websites or resources, what what do you think makes cleverly different?

Crystal Esquivel 18:35
I think there’s several things I mean, it is what we were looking for and couldn’t find. And so that is something that’s really well curated, something that is up to date and modern in what it recommends. And what you know, it teaches you about, there’s the latest app, it’s not you know, here’s the basics of Microsoft again. So it’s people who are, you know, movers and shakers are making this and it’s also run and written by EAS. So we’re not going to share something that’s completely unhelpful to others out there in the same role. So I think it’s different in that it’s written by EAS for EAS, we are super, super picky. And we curate things really well from every link to every tool. It’s also I must say beautifully designed. So you don’t find a lot of that out there. And it’s just really pleasant to look at Pleasant to read. Hopefully, it’s something positive in your inbox that you can just kind of, you know, scroll through and find ideas or find a new playlist or just something that makes you smile. So I think it’s for us. It’s just, it hasn’t been made yet. It hasn’t. There hasn’t been a modern and well designed, really helpful resource out there for the people out there that are like us executive assistants and admins.

Jeremy Burrows 19:57
So you’re saying that my emails texts that are text only text only emails aren’t designed for you.

Crystal Esquivel 20:06
Yeah, maybe we should talk later about your design.

Jeremy Burrows 20:11
That’s awesome. All right, Alessandra, what makes an assistant a leader?

Alessandra Thomas 20:16
Yeah. So 99% of the time, you can assume that the EA is making the recommendations that the leadership team is coming up with. So if the leadership team is like, we’re having this retreat, and we’re staying at, you know, XYZ place, it’s probably because an EI picked it, you’re probably eating the food that the EAA picked, you are probably looking at a event brochure that the EAA created and executed. And all of those micro decisions, all of the pieces that make something great, whether that’s a meeting, or a big event, or a gala, or just a simple trip, plane travel, an EA probably got it done. And I think that people often credit, you know, the CEOs, the people at the top the faces with making all the quote unquote, hard decisions, and they probably, you know, make a lot of hard decisions, but the day to day decisions, those are being led by pas who are getting their execs to those outcomes. And I mean, I think that’s incredible. I I love sitting in that seat. That’s the type of leader that I want to be I don’t need to be on the cover of Time. I’d love to be like mentioned at the bottom of the article, maybe but you know, being that behind the scenes person who’s leading their executive or their clients to, to the decisions, I think makes assistants, incredible leaders, and I’m probably under appreciated maybe if I if I daresay

Jeremy Burrows 22:03
Yeah, well said, Crystal, I had somebody email me or send me a LinkedIn note the other day, saying, Hey, I just started as an assistant and I don’t know where to start. Where would you point someone who reaches out to you and says, Hey, I am a brand new assistant. What do I do?

Crystal Esquivel 22:23
Okay, this is gonna sound really trite. But two things, one, subscribe to our newsletter. Read Jeremy’s book. And I am not kidding. I actually wrote a blurb but for the front of Jeremy’s book, because it was so good. There are other books out there, but Jeremy’s is just really good at describing why you’re doing what you’re doing. And you know why you should make the decisions you’re making, why you should be thinking how to think ahead. Yeah, I think both of those are great resources. And hopefully in the future, we’ll have some more courses and things for you to take.

Jeremy Burrows 22:57
Awesome. Well, thanks for the shout out. And for those listening, I did not tell her to say that were that that was that was not premeditated.

Alessandra Thomas 23:08
I think that as well.

Jeremy Burrows 23:10
Awesome. Well, Alessandra, and crystal, thank you so much for Yeah, sharing a little bit about your story. And thanks for just taking a risk and starting cleverly. And I’ve enjoyed following you guys since your launch and just, you know, checking out your newsletter every week. And how can people listening? Find out more in how can they subscribe to your newsletter?

Crystal Esquivel 23:41
Yep, so you can just head to our website, which is the You can also find us on Instagram and Twitter at the cleverly CO and it’s really easy to subscribe run on the website. And we really like giving things away. So when you subscribe, you automatically get wallpapers and principles, access to our ultimate guide to the best di software with discounts. And then of course, our lovely newsletter every week.

Jeremy Burrows 24:08
Perfect. And I will link to all of those in the show notes. So everybody can find your quickly and I’ll even link to your LinkedIn so people can connect with you too on LinkedIn. But yeah, thanks. Thanks again. And best of luck to you and cleverly and I always appreciate talking with fellow assistants who are also kind of jumping into the whole side hustle world. So yeah, thanks for being on the

Crystal Esquivel 24:36
show. Thanks for having us. Thanks

Alessandra Thomas 24:37
so much, Jeremy.

Jeremy Burrows 24:39
Thanks again, Crystal and Alessandra for a great interview. Please tune in to the show notes at to check out links to connect with Crystal and Alessandra and we hope you enjoyed this episode and we’ll see you next time.

Speaker 1 25:05
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