Creating a Supportive Work Culture for Families

Megan Dalessandro, a content producer, creative director, and self-described creative Swiss Army knife, discusses the importance of creating a healthy work environment for all employees, the impact of gender roles on career progression, and practical advice for freelancers managing their finances.

Host Kaila Sachse also speaks with Meg Dalessandro about the challenges of balancing a career and personal life. Meg shares her journey of navigating career setbacks, redefining success, and finding a supportive work culture at Wistia. The conversation emphasizes the need for empathy and understanding in the workplace, especially for parents and those facing personal challenges.

More About Megan Dalessandro

Megan Dalessandro (most people call her Meg) is a content producer, creative director, and brand marketer who has spent most of her career trying to figure out what balance actually looks like and whether it really exists.

For a long time, she believed the next title or promotion would finally bring the security to start living the rest of her life: traveling more, getting married, maybe starting a family one day. As the kid of a single mom, she was determined to build a steady foundation, no matter what. But after she broke her ankle in three places and got laid off in the same season, she realized no amount of ambition or planning could protect her from uncertainty.

That pause forced her to rethink everything. She started her own business, learned to trust her instincts, and decided it was possible to build a career and a personal life side by side without feeling like she was failing at one or the other.

Today, she has found that sweet spot at Wistia where the culture actually backs up its promises. People really do take time off, and parents (and non-parents) are supported in a way that feels genuine, not performative.

Outside of work, she’s usually roller skating at the skatepark, leaving voicemail newsletters about creativity, or taking too many photos of her cat, Noodle. She lives in Oregon with her husband, James, and is still learning how to let work be just one part of a bigger, more interesting life.

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Transcript

Kaila Sachse (00:02.371)
Hello from the Bringing Up Business podcast, where we talk about business and parenting. I'm your host, Kaila Sachse, owner of a creative and marketing agency called Yumari Digital that specializes in websites, marketing campaigns, and branding to help small businesses grow. I am also the mom of a very energetic two-year-old. So if you're watching this on YouTube and I look tired, please don't tell me that I look tired. Just know that I am.

However, I have plenty of energy to chat with today's Meg D'Alessandro, who is a content producer, creative director, and self-described creative Swiss army knife. Meg spent most of her career trying to figure out what balance actually looks like and whether it really even exists. For a long time,

She believed the next title or promotion would finally bring the security to start living the rest of her life. Traveling more, getting married, maybe even starting a family one day. As the kid of a single mom, she was determined to build a steady foundation no matter what. But after she broke her ankle in three places and got laid off,

in the same season, she realized that no amount of ambition or planning could protect her from uncertainty. That pause forced her to rethink everything. She started her own business, learned to trust her instincts, and decided it was possible to build a career and personal life side by side without feeling like she was failing at one or the other. Today, she has found that sweet spot at Wistia.

where the culture actually backs up its promises. People really do take time off and parents and non-parents are supported in a way that feels genuine, not performative. Outside of work, Meg is usually roller skating at the skate park, leaving voicemail newsletters about creativity or taking too many photos of her cat, Noodle. She lives in Oregon with her husband, James, and is still learning how to let work...

Kaila Sachse (02:18.945)
be just one part of a bigger, more interesting life. Today, we're going to dive into what a healthy work culture looks like so that if you, dear listener, are an employer, you can provide better support for your team. Meg, I'm excited to chat with you today and welcome to the show.

Meg Dalessandro (02:40.878)
Thanks for having me. I'm really excited to have a chat with you too.

Kaila Sachse (02:43.5)
Yeah, yeah, so before we get into it, I need to know what is a voicemail newsletter?

Meg Dalessandro (02:50.018)
Yeah, so it's kind of like voicemail newsletter podcast. I post monthly on Substack. so with Substack, can do like a newsletter blog. And so was doing that. But then I have come from the world of podcasting and has always been really drawn towards the audio format. And so as a content producer, podcast producer, I started this by thinking, what if I started a publication?

with a voice note and then let that feed into the newsletter and kind of design something that could fit both use cases. That way it could kind of feed off of my creative motivation in the moment with whatever voice note is kind of popping in my brain and also keep myself on like a monthly kind of scheduling, post scheduling schedule. That doesn't make much sense, but.

Kaila Sachse (03:35.757)
No, no, no, I get that. get that. It's like, I have a hard time like staying on a schedule of pushing out content. And so it's cool that you found something that holds you accountable. So I'm trying to wrap my mind around this. Okay. Like, is it a podcast or is it like, what format does it live in? Oh,

Meg Dalessandro (03:53.14)
Why not both? So it does live on wherever you can find your podcasts like Apple or Spotify or YouTube or things like that. But it is mainly on Substack where I post both the audio file and the like transcript, which is like the blog post. But that if you subscribe, get sent to your email. So it's kind of like a triple whammy of, know, you can see it on the blog on the website, you can hear it in your ears and your podcasting app, or you can get it in your inbox.

Kaila Sachse (04:19.924)
cool, okay, always learning, always growing. I love it. Okay, so walk us through your journey. You started at a company called Privy and then what? You told me this story before and it was so cool. Now you just have to share it, it's so good.

Meg Dalessandro (04:22.743)
Yeah.

Meg Dalessandro (04:37.698)
Thanks. Yeah. It's funny because I originally went to art school at MassArt in Boston and I studied graphic design and user experience design. And so getting out of college, I was really looking for that entry level design position, which is where I landed at Privy as a marketing designer. And at the time, Privy was an e-commerce, like marketing software with probably about 10-ish employees. So about seven or so developers, the founder.

and one marketing person who was my boss and me. And so it was really cool to join a team when it was at such a small stage and then also be with them for a few years and watch them grow because I really got to learn about marketing through osmosis. Like I remember vividly my boss, Josh, at the time, he was talking about the marketing funnel and I was just looking at him and he's like, you look confused. And I'm like,

what is this funnel everyone keeps talking about? Like, what is this funnel? And like, what does that have to do with anything that I have to design? And so I think it was that conversation and me also kind of asking like, why are we making national pancake day graphics? Like, what is this doing for the business? I think that's where my marketing and design brain kind of started to sprout. And so I was working at privy for a few years. From there, I actually went to a venture capital firm called OpenView, which is also in Boston.

And there I joined their marketing team to grow their thought leadership program. So like their, their lead investors would have like video series or podcasts or things all over on LinkedIn or YouTube. And by building their personal brands, we built the trust. then that way founders, when we're reaching out to them for funding, they trust us more. They want to talk to us. They know that we're real people. And it was really fun to be in a new space that was really kind of buttoned up.

And really I got the opportunity to make things more fun and push the boundaries a bit about what does VC content look like. But in both of those interactions, I would say I learned so much, but it was also so fast and so like all encompassing. And I think that was partially just because of where, like, you know, where I was early in my earlier in my career as my early twenties. And I was just prone to burnout. Like I was just basically like, I want to keep

Meg Dalessandro (06:54.062)
working as hard and fast as I can to build that stability for myself and for my future. Cause like, I'm going to get it no matter what. Like I have like been like motivated by not even like spite, just like pure, like I'm going to do it whether you like it or not. And I think that mindset made me, you know, burn out a lot and kind of get in the cycle of burnout, which it brought me to really great places. Cause I made really great work, but it wasn't super sustainable. And so was interesting after being at OpenView for a few years,

Kaila Sachse (07:07.903)
Yeah.

Meg Dalessandro (07:23.726)
I, after I think, yeah, three years, I ended up breaking my ankle, like exploding it in all the different ways. Took some medical leave and really had to like, was forced to take a pause because I couldn't do my work. I couldn't walk, took like six months to learn how to walk again, like this whole journey. And then I got back and then the company, the firm decided that it was like winding down. So nothing to do with like my performance or anyone's performance necessarily. It was like some sort of like logistical thing where they were like.

we just have to shut down the firm and we're gonna give everyone severance and so that way we can support you in whatever you do next. And so it was like, I finally got through this journey of this really hard, really challenging time, both mentally, physically going through this injury, coming back to work and then having, you know, feeling like what am I doing now? It was just like another sign from like the universe being like slow down. Like.

Kaila Sachse (08:16.262)
Mm-hmm.

Meg Dalessandro (08:16.942)
Because I was already thinking about like, all right, like I'm gonna get back to work. I want to work on X, Y, and Z. And then I'm reach out to this person and do that. And I'm gonna write this. And I was already feeling myself like ramped back up into that unrealistic expectation of myself even before I got back to work. And so I think, yeah, going through both of those at the same time was definitely challenging, but it was kind of what I needed to force myself into thinking, what do I really want? What does balance really look like? And especially at this point,

Kaila Sachse (08:29.649)
Mm-hmm.

Meg Dalessandro (08:44.43)
I was engaged. And so I was thinking about that next stage of life. Okay, I'm getting married in the next year. And, eventually my husband and I want a family. Like what sort of career and job will set me up, not only financially, but also for like the life I actually truly want to live. Like, am I going to be on my deathbed wishing that I sent more emails? Like, no. Or like, why did I made another podcast episode? Like, no. So just thinking about what is that true value? And I feel before earlier in my career,

Kaila Sachse (09:02.782)
Yeah.

Kaila Sachse (09:06.255)
Mm-hmm. Yeah.

Meg Dalessandro (09:14.626)
the value was so much more on money and the title. Like I was so like dead set. Like I need to have a director title before I'm married and have kids. like, you know, you always hear about, you know, women like, like your career takes a swan dive once you have children time away. And like being a feminist, I'm like, no, like it doesn't mean it's not going to like women and like, I like,

Kaila Sachse (09:19.529)
Mm.

Kaila Sachse (09:32.89)
Mm-hmm. Mm-hmm.

Meg Dalessandro (09:44.546)
while that's coming from a great place, it was also coming from like an unrealistic expectation of like, I need to accomplish everything in this super short time, otherwise I'm never gonna get to it. And that's just unrealistic. And I think that's maybe just me in my twenties, just thinking I have to get everything done before a certain time. And I'm sure a lot of people can relate to that.

Kaila Sachse (09:51.91)
Yeah.

Kaila Sachse (09:55.709)
Yeah. Yeah.

Yeah. yeah. It's not it. I think it's also like important to consider too how culturally we are raised with parents who were able to afford homes in their 20s. Not saying that people can't afford that now, but it's a it's much more challenging. I mean, that salary, that salary to home price ratio is just so much different now.

Meg Dalessandro (10:21.475)
Yes.

Kaila Sachse (10:28.004)
And also the expectations, especially on gender roles for parenting, raising a family, know, typically, you know, the age old story, like man goes out and hunts for the money and the woman stays home and raises her babies. And that's just how everybody accepted society as it used to be. And now, so we've we were raised with this idea that like, okay, we can do the things we can buy the house and then we can have the babies and like.

Meg Dalessandro (10:28.29)
Totally.

Kaila Sachse (10:57.713)
everything's picture perfect. There are all these milestones to hit, but this day and age is just, it's different. It's just different. And so I can understand and empathize how you are so hard on yourself and wanting the title and wanting that, that bigger salary. And it also doesn't help to that you and I are the same. are both extremely motivated. We just want to take over whatever it is that we set our minds to. And so.

I get it. I get it. just, just want to like extend some empathy to you in that. And also any listeners who can relate, which I'm sure there are a ton, we are all in this boat together. Like you, you know, you're not alone.

Meg Dalessandro (11:41.134)
Thanks, I really appreciate you saying that. Because I sometimes do feel like, people say, oh, you're so ambitious. Even at my wedding, the speeches from the best man and maid of honor, everyone's like, oh, Megan and her ambition and all this and everything. And it almost made me reflect on, is that a bad thing? Is it too much? Is it almost ambitious to a fault? is it like, it kind of made me rethink

Kaila Sachse (12:01.276)
Mmm. Mmm.

Meg Dalessandro (12:10.656)
about how I view ambition. I think it's so great that I love that people think I'm ambitious, because they know I'm the lady that can get stuff done. But it's, yeah, I think my relationship to the idea of being driven and ambitious has changed a bit. I think I am always trying to now find the balance, not just with ambition, but with rest. And true, true rest, not like, I'm resting while I do something that's also productive, because I'm also very guilty of that. I'm like, my rest also needs to be productive, though.

Kaila Sachse (12:14.832)
Yeah. Yeah.

Kaila Sachse (12:29.799)
Mm-hmm.

Kaila Sachse (12:35.462)
Yeah.

Kaila Sachse (12:40.235)
Yep, just, I felt that, yep. I struggle with that too. If anybody out there has an answer to how to do that, or do you have an answer for how to truly rest and get off the grid, like please share, because I'm still struggling on how to do that.

Meg Dalessandro (12:55.596)
I mean, it's so hard. I really struggle. I'm a person who will like, I'll be like, I need a break from my big screen, my computer. So like, let me go on my little screen while I watch a different screen and watch TV and also be on my phone. And then it's like, sometimes, you know, that can be really enough to like disconnect. And it's like kind of good to be like, semi absorbing all these different screens and like, you know, you're mellowing out. But other times it's like, you don't realize the toll that like,

Kaila Sachse (13:07.931)
Yes!

Meg Dalessandro (13:22.51)
that's taking by like being on your phone and watching TV and like listening to something and how multitasking, even though you might be trying to do it as a way to relax, it might actually be causing your brain to be spinning when you don't even like realizing it. I don't know if you've experienced that.

Kaila Sachse (13:35.906)
Yeah. Yeah. And then you add in a toddler who's like, mom, mama, mama, like wanting all the things. And it's, it's just overload. Like the inputs, my, my inputs can get fried by the end of the day. And you know, I realize, you know, by the end of the day, if I am that fried and I find myself like starting to get reactive and the best thing for me is to just like take a beat.

go step away into another room and like leave the phone, leave all the devices and just go rest. You know, maybe I go out to my garden and go water some plants for 10 minutes or however much I can muster, you know, just to like recharge. Yeah.

Meg Dalessandro (14:12.27)
Yeah. Yeah. I would say for me, change of scenery and yeah, doing something physical is so big. Like that's honestly my relationship with roller skating is largely trying to build in that like very present minded, like relaxation time. Even though it's like a physical activity, like it feels so relaxing to me because I have to be focused. Otherwise I'm getting, otherwise like I can get hurt or, you know, like there's so many things that can happen. So it like forces me to be super present.

Kaila Sachse (14:33.465)
yeah.

Meg Dalessandro (14:41.878)
And it also forces me to change my scenery. And when I was hurt, when I hurt my ankle, I realized that like, that was my biggest, probably like coping mechanism that I had for rest. And then once I couldn't use that, like, know, coping mechanism for rest, I started grasping around like, my gosh, like, how do I actually rest when I can't like move my body? And so I actually got really into like collaging and coloring.

Kaila Sachse (15:01.391)
Yeah.

Meg Dalessandro (15:05.622)
Like I would try to like just like work with like physical media because in all of the content production, design and video stuff I do is mostly all digital. And so I'm usually on a screen. I'm usually like hunched, know, hunched over my computer. And I like, I just find that working with physical media and like putting the phone away, maybe I have music on, maybe I don't, but I think like literally just coloring. Like I have like a Hello Kitty coloring book my friend gave me that I have been like jamming on lately. So if I get into that mode of where I'm like...

Kaila Sachse (15:15.118)
Mm-hmm. Yep.

Meg Dalessandro (15:33.166)
kind of want to watch something, but not really, but I want my hands to be busy and I don't want to go on my phone because that feels like an energy suck. I'll sit down and I'll color while I watch TV because it kind of gives me that like fidgety fix of like doing something, but like it feels it feels productive and it's like not it's like actually restful. So I feel like people have always like, I don't know coloring books are not anything new, but I have like come back around to them and I've that's been like my latest hack recently for like, okay, I don't want to be on my phone.

Kaila Sachse (15:45.766)
Thanks.

Yeah.

Meg Dalessandro (16:01.282)
but I do want something else to do while I'm watching something.

Kaila Sachse (16:04.487)
That's a fantastic idea. You know, one of my go-tos, this is an old go-to that I wanna re-amp into my life, is gouache paint. So gouache is a water-based paint, and that would be safe around my little one, because if he were to, I don't know, get it on him, it's not toxic, and also if it spills on something, I'm sure I could wipe it up. I don't know. I don't know. I'm sure that could be clean. That's a great, oh, I'm so inspired now. I wanna gouache paint while I'm...

Meg Dalessandro (16:23.714)
Yeah.

Meg Dalessandro (16:27.437)
Yeah!

Kaila Sachse (16:32.624)
watching TV or whatever, yeah.

Meg Dalessandro (16:34.368)
say, another good thing that if you're into collaging, but you're like, like, I just need all the things because I'm a person very much I need my, like, if it's, if it's, can see it, it's accessible, and I'll do it. But if it's like a craft that I put in my closet, I'm like never gonna see it or do it again. But I've been doing these monthly, like vision board collages where it's like, the beginning of every month, I sit down and I think about like, what do I like want to like get out of this next month, I want to like eat my favorite foods or like go do this or that. And so I've been doing them.

Kaila Sachse (16:49.114)
Mm-hmm. Yep.

Meg Dalessandro (17:03.978)
this year is the first year I've done them but it's like I have like, January is like, went to Hawaii and I bought like a lamp for my bedroom and like so it's like things that are not like sometimes they're really exciting like going to Hawaii but other times they're just like I want to like hang out with my cat and play video games and like go on a fun date. Yeah, so what makes these so I have all of them so I'll show you I have like a bunch of them. This is my my July one which is very fun. Going to a friend's

Kaila Sachse (17:06.982)
I'm gonna see when.

Kaila Sachse (17:21.498)
I love that! How fun!

Kaila Sachse (17:31.513)
Bye.

Meg Dalessandro (17:32.16)
child's like first birthday party, thinking about houses and all this fun stuff, going to the beach, eating peaches, you know, all the good stuff. And so what I found was, thanks, what I found was so made that like accessible was they have these books now that are literally just collage books. You literally just have like, this one's kind of a weird one, but I have a different one. Yeah.

Kaila Sachse (17:40.857)
That is so fun.

Kaila Sachse (17:56.368)
For everybody listening right now, Meg is flipping through a book of just full page imagery. And it looks like a bunch of little graphics or full on backgrounds that you can cut from. that is so fun.

Meg Dalessandro (18:05.196)
Yes.

Meg Dalessandro (18:15.006)
So each book has just like this one, I think is just things to cut out and collage. So there's not really much themed, but you can say like, oh, I'm looking for vintage signs. And it's a whole sheet of vintage signs that are all cut out so that it's easier to cut them out. Or there's flowers or animals or so when I go in to make these, it's not like I feel like I'm starting from scratch. It kind of just feels I don't know, it just makes it so much more accessible. And I feel like the more you can make those like restful things seem accessible.

and actually restful, not sneakily productive. That's where I find the sweet spot of true rest and balance.

Kaila Sachse (18:45.286)
Hahaha

Kaila Sachse (18:50.917)
That is so inspiring. Okay Meg, thank you. That's the end of our show. We've learned how to rest everybody. No, I'm just kidding. We have more to dive into. So you...

Meg Dalessandro (18:54.67)
Yes.

saying, I don't have children, so that's also a whole other, I don't have children yet, so that's a whole other thing. It's like I have different time schedule as other people with other family and obligations. So that's something that I also just highlight as well.

Kaila Sachse (19:10.297)
Yeah. Yeah.

Yeah, no, and that's an important point. So if there are any parents listening who are like, okay, hold on a second. I don't have time to collage. I don't have time to gouache paint. I get it. I completely understand. I will say that the first two, maybe like year and a half of my kid's life was absolute just, I was consumed with survival. It's like either feeding him, feeding me, making sure.

Meg Dalessandro (19:22.455)
Yeah.

Meg Dalessandro (19:39.01)
Mm-hmm.

Kaila Sachse (19:43.299)
The house isn't just completely on fire. Like dishes aren't piled up and all that, which they still are. They are forever piled up at this point. But learning to be okay with that. But once like that beginning stage of getting through the newborn infancy, you kind of get your bearings as a parent and start to fall into some rhythms and rest does become possible. And in order to make it happen,

Meg Dalessandro (19:49.998)
Yeah

Meg Dalessandro (19:53.644)
Yes.

Kaila Sachse (20:12.194)
you have to prioritize it. You just have to. And I found that the easiest way to prioritize it, there are two different ways. If you have a partner, have your partner watch your kid while you alone go rest. Or if you don't have luxury of a partner, try to implement your kid, try to involve your kid in with the activity. So for example, my kid and I, he,

He loves to garden. I love to garden. And so what do we do? We go out into the backyard every evening and that's what we do. It's a full like 30 minute ritual. I give him the hose. Yes, everything gets muddy. He is covered in mud. But guess what? It washes off. I just spray him down before we get back inside. And then I toss all this stuff in the washer. Like it's fine. He'll be okay. But that seems to be the key as to either involving my kid.

Meg Dalessandro (21:03.491)
Mm-hmm.

Kaila Sachse (21:08.111)
or asking somebody to watch my kid while I have my own pure alone time. And then when I have that pure alone time, it's like what Meg says, go do something that's actually restful and it will actually restore your soul. For me, it's getting down the street to a Pilates class, a bar class, a yoga class, like something like that. It's moving my body too. That's what makes me feel connected.

But yeah, and part of that is experimentation too and figuring out like what works for you. So I don't know. That's just like my tips and tricks for younger parents. Like take it easy on yourself. Do know that there is light at the end of the tunnel. Like the infancy stage will pass and sure you will have time for yourself soon. yeah, anyway. Okay, so let's move on. So you were talking, you had broken your ankle, you got laid off.

Meg Dalessandro (21:42.062)
Mm-hmm.

Kaila Sachse (22:04.151)
Then what? How did you manage that? Because I can only imagine at that point in your life, that must have been so overwhelming and disheartening for somebody who is so ambitious. Like, how did you reinvent yourself? What did you do?

Meg Dalessandro (22:17.644)
Yeah, that's a good point of like reinvention is because that's truly what it felt like leading up to that year. I like that year I was doing 365 days of roller skating and so I was on day 222 when I hurt my ankle and it was such a bummer because it was like, my gosh, like, like, it was like I remember sitting in the hospital bed, you know, in a lot of pain, but like, really like just like the waves of like,

Kaila Sachse (22:32.983)
No, so close.

Meg Dalessandro (22:47.502)
true sadness and disappointment coming over me of like, I'm not going to reach this goal I set for myself. I had a vacation planned. I was like, that's not happening because I can't even walk or do anything. So was like that. And then it was also like, oh my gosh, now I have all this stuff at work. Am I going to be able to work? If I can't work, am I going to lose my job? It all escalates from there. And so it was really tough. think I eventually, I first had my surgery because I had to have

Kaila Sachse (23:00.13)
Meg Dalessandro (23:17.142)
urgent surgery after it all happened, I dislocated and broke everything. So they were like, girl, you need help. And so thankfully the surgeons did a fantastic job and everything, but it was still like two months before I could start physical therapy. And so I had to just be on the couch, unable to move for that long, which was truly the hardest time. Cause it just felt like no progress. And as someone who's ambitious, progress is like how I equated my worth and value. And so I felt really awful about myself and also just feeling I was asking so much of my partner.

Kaila Sachse (23:21.61)
haha

Kaila Sachse (23:39.168)
Mm-hmm.

Meg Dalessandro (23:44.29)
because he was doing everything from the groceries to the laundry to the cleaning to literally helping me shower and helping me do like everything and also trying to keep my spirits up because he knows how down I am. And so he was really holding down the fort for both of us. And I am just like so appreciative to have had a partner that could have helped me through that. And so once it became clear, I tried to go back to work and it was like my mental state was just getting so much worse and I had to prioritize my mental health.

Kaila Sachse (23:50.402)
Thank

Kaila Sachse (23:56.62)
Yeah.

Meg Dalessandro (24:13.398)
and realize like, I am more like depressed than I've ever experienced in my life. It felt like I was wearing a weighted blanket on my brain, like physical, like true physical depression. And I've battled depression in my past and anxiety and things like that. But this was like truly like an all encompassing overwhelm. And that's where I had to make the decision of like, I need to take medical leave and like actually prioritize getting like extensive physical and mental therapy and like help myself through this. And so that's what I did. And I was so lucky that I worked for a company that

Like, you know, mean, like legally they have to let me take the medical leave, but they also like emotionally were like very understanding, very there for me. didn't make me feel like judged or anything like that. And, like extra fragile, you know, like no one was treating me like walking on eggshells or anything. It was just very much like, Meg's going to take this time off to heal and we're going to talk to her when she gets back. you know, just like let her be while she works on this and then we'll get back to her. So I felt really grateful for that at least. So.

Kaila Sachse (25:08.267)
Yeah.

Meg Dalessandro (25:08.398)
Honestly, once I made that decision, it was a huge weight off my shoulders, because I was battling that for the first few weeks of being injured. And then once I had all this time, because I wasn't working, and I had, you I in lot of physical therapy and like talk therapy, but I had all this time. And so then that's what really let me reflect and be like, all right, like, let's say I didn't work at OpenView anymore. Like, what would I do with this time? And so that's when I started thinking about like, what would my next role be?

Like I had always thought about it just being full time. and so when I got out of, when I got laid off, you know, it came back from my injury, got laid off. And then I was thinking about what's next. I was applying to places left and right and just hearing crickets, like just nothing like 50 plus applications hearing nothing. But then I'm also like, you know, hearing like a lot of people are reaching out to me on LinkedIn asking me for freelance work. And I was so hesitant because I was like, I don't want to do the business thing. Like, I just don't think I can do it. Like I just.

Kaila Sachse (25:52.01)
Oof.

Meg Dalessandro (26:02.678)
like as ambitious as I am, was just like, the whole money piece of it just seemed so overwhelming and so like I was just going to mess it up somehow. And eventually I kept applying to places and applying to places and I started taking on freelance work here and there for people I knew. I that would treat me really well, like people who I knew like could kind of handhold me through this, like first free like, you big freelance endeavor, excited freelance in the past, but didn't make it like an official LLC business or anything.

Kaila Sachse (26:29.62)
Yeah.

Meg Dalessandro (26:29.848)
And so eventually I was doing that for a few different clients, writing my newsletter. And I actually landed my first retainer client through my newsletter by doing like a guest post on their newsletter and then swapping. So that was kind of like one of my first aha moments of like, Hey, wait, like the stuff that I'm doing on my own is actually starting to resonate with other people on that in services that I could provide. And then the person that I collabed with, you know, it was like, would you ever come work for us in our agency as a creative?

like specialist or something. And I was like, yeah, that'd be awesome. So I started doing that. And then once I got my dip my toes there, it was like, pretty soon after I was getting other retainer clients, other kind of one off projects. And I was like, all right, now that I have like, pretty much a full plate, I should think about making this a real business. And so then I formed my LLC here in Oregon, you know, officially made my website, did all of that. And then yeah, I was freelancing from beginning of 2024 through the end. And it was actually in, I think,

near the end, like fall of 2024, I saw there was a Wistia job posting for video producer. And my one of my mentors, Jay Akunso, he sent it to me saying like, Oh, I thought of you for this. that alone, like made my day, like made my week. I was so like, Oh my gosh, you think I could be good enough to work there? Like their videos are so good. And like, I had always looked up to them for both their like thought leadership and just like

Kaila Sachse (27:43.348)
Hmm. Hmm.

Kaila Sachse (27:49.44)
Hmm.

Meg Dalessandro (27:56.024)
brand strategy, but also just like the pure like aesthetic and like visual quality of like everything they make is just stunning and also so differentiated because it has like true like human personality behind it. And I've always found that to be really cool for like business to business marketing. And so I was like, my gosh, that's a dream. And so I wrote this cover letter that was basically like, dear stranger, thank you so much for making my entire week by posting this job listing like, you know, and I like had my little spiel like who I was and all this stuff. And it was just like,

Kaila Sachse (28:06.496)
Yeah.

Meg Dalessandro (28:24.194)
thank you for making my week, even if you didn't know it by like, you know, posting this. Like it made my week to think that I could even possibly work here. And so they got back to me and they're like, well we actually need someone in real life, like near the Boston area to be able to come into the office to film. So this is not gonna be like a good fit. And so I was like, well, I'm okay. But then they're like, we're actually thinking about scoping this other role that we think you'd be a really good fit for.

Kaila Sachse (28:28.511)
Hmm.

Kaila Sachse (28:41.235)
Mm. Mm.

Meg Dalessandro (28:49.358)
And so I was like, okay, let me know. And they're like, all right, it's going to be a couple of months because they were figuring stuff out. And I was like, perfect. I'm getting married and going on my honeymoon. So peace out. And so that was nice. I like had some more clients during that time. And then by the end in like November, December, they reached out to me with the role. did the interviews, got the role, and then ended up being full time at Wistia since yeah, 2025. And it's been so fun. It's, I feels very surreal to work somewhere where people genuinely.

Kaila Sachse (28:57.726)
Yeah.

Meg Dalessandro (29:16.694)
like truly enjoy not only their jobs, but like everyone they work with. Like I have had meetings with people who have been there for five, 10 plus years. And they have like, they couldn't say anything greater about the company and how much they've been supported through like different phases of their lives. And I've just noticed that a lot of the people on the team are younger parents or just like younger folks or like, you know, older folks with children. And it's just so nice because it's truly the first company that I feel like

Kaila Sachse (29:19.967)
Mm.

Meg Dalessandro (29:45.932)
has just gone above and beyond to truly understand the parenting experience and provide support in that way. And so it was kind of like a happy accident. I truthfully probably would have taken this job because I've been such a fangirl of Wistia for so long that I probably would have taken it even if they didn't have this like amazing parental leave policy and support. But then joining and then finding that out, it was like, yes, it's exactly what I like was hoping for was like some sort of environment that would actually be.

Kaila Sachse (29:51.923)
Yeah.

Kaila Sachse (30:04.573)
Yeah.

Meg Dalessandro (30:14.434)
like very supportive for all seasons of life and all types of people. And yeah, I just am like so happy and feels very, still feels very surreal that I get to say that I work there.

Kaila Sachse (30:22.035)
That's so beautiful. That's so beautiful. What are some of the practical policies that they have that support their culture? You know, mentioned a parental leave policy. What does that look like? Are there any other benefits that they offer? What does it all look like?

Meg Dalessandro (30:40.3)
Yeah, so at a glance, it's, I believe, for four months of parental leave. So for the birthing or non-birthing parent, and then you can decide how you want to split that up. So you can do the first four months altogether, or maybe do two and a half, three, and then some later, once potentially the other, maybe you're doing some sort of situation where one partner is going back to work before the other, or maybe before you're going to daycare or something like that. So it's really flexible, which I found to be, that seems to be really considerate, just based on like,

I don't know, everyone's different. Everyone has different like work, life balance and styles of parenting and everything. So I just feel like it's so nice to have that flexibility. so that was one thing. And then the other thing that I really love is they have a, Slack channel and it's just like parenting. And it just seems like I'm not, I'm not included in it I don't have a child yet. They offer, they were like, you can definitely like observe if you want, but I was like, I'm good for right now. But you know, eventually, hope to join that channel, but it just seems like people there, really have like useful discussions around.

Kaila Sachse (31:16.754)
Yeah.

Kaila Sachse (31:30.162)
Yeah. Yeah.

Meg Dalessandro (31:39.02)
like, like, did you notice like this was closed? Or like a lot of people live around a certain area. So it'll be around like different closings or things like that. Or did you see this story or just getting like a sounding board of other parents? Or if they're planning like we had a giant offsite in Denver, Colorado, so that we all as a remote company can all come together and hang out for a few days. And so as they were planning that, I know that they reached out to the parenting Slack channel to get a lot of feedback on like, will your families be joining us? Like, could we provide?

Kaila Sachse (31:48.018)
Yeah.

Meg Dalessandro (32:05.91)
other accommodations or recommendations for them to do things while you're doing, you know, the work stuff and just like really considering like, not just the person that works there, but everyone who supports the person that works there, like their whole family, which I find so kind. And even just like my very first meeting that I had like my first day was with an HR person. And she was like, I'm sorry, like, I have my daughter here with me. Like she might like pop in to the video every once in a while because

of whatever. And it was just like, so casual, so nice. And it wasn't like, you know, it was just, she felt so comfortable being able to do that. And it just gave me the sense of ease of like, okay, it's not like people have to like hide their children here or act like their lives aren't impacted by these like little beings that make up so much of their like, life. And it just made it seem like parenting is possible because kind of like you were saying before, like parenting back when it was our parents generation.

seemed more possible because you could buy the house, you could do the things, you could hit all the milestones where I feel like a lot of people nowadays, even if they want children, it's really hard to make it seem possible to give them the support. And I struggled with that for a long time because I never, because of my growing up single mom, like a really tough financial situation, I just never thought I would get that for myself. I always like wanted a family and everything, but I just never thought.

Kaila Sachse (33:12.85)
Yep.

Meg Dalessandro (33:27.534)
it could truly happen for me that like I would actually be in a place where I could support not only me, but like another person or multiple people. So it feels very surreal. Even I feel very lucky to be able to do that because there's so many people that don't and it's really hard because it's a systematic issue that I don't know the answer to.

Kaila Sachse (33:42.651)
Mm-hmm Yeah, yeah, no, I there's we have an episode with Nikolai Paquin He's a freelance designer super talented and he dives into that how he and his partner are struggling with planning for the future it because they want kids they want the house they want all the things and the the expenses of life are making that feel utterly impossible and so it's just it's it's it's so

It's so, challenging. Zooming, okay, so zooming back over to Wistia, how big is the company? You know, it sounds like they don't get caught up on people having kids. And so it's okay to be full on human beings. you know, back to like original question, like how many people are at the company and how do you think they're supporting the family culture behind the scenes?

Meg Dalessandro (34:41.9)
Yeah, so the company is about, I believe, we're a hundred and between a hundred and sixty to a hundred and eighty people. So less than two hundred people, but still large and we're spread out across the United States. And so I think The main way that they're supporting the parents at Wistia and even non-parents is that they actually have like a parent advisory board. So they actually have like a group.

of volunteers from the company who will kind of, who not only manage that parenting kind of Slack channel, but also will meet and kind of get a gut check of how people are feeling. What are we, do we feel like people are feeling supported? Is there more that we can be doing? Are things we were doing that we were doing actually still useful or should we change them? And so that was, again, the first time I've ever heard of a company having anything like that. And it was just really eye-opening because it was just, it just really inspired and invigorated me.

like you're just saying, just, makes it seem possible. and it's also like, you see, have like a every week or at least like every week, the marketing team has like a recurring slack thing. It's like, Hey, like what did it, it's three things, like what did you, it was a highlight from your weekend to what do you work out this week? And three, like, are you going to be out at all? And it's like a prompt that you can like choose to say, like, you don't have to reply to it. It's just like, if you want, can. And like every week is so nice. Cause people will post like, you know, a highlight from their kids, like dance recital or like something. And it's just like,

Kaila Sachse (35:40.901)
Yeah.

Meg Dalessandro (36:06.806)
so nice that people feel also very comfortable sharing their families with each other. And everyone kind of gets to know the personalities of everyone's kids and families and pets and everything. And it just makes everyone feel also very much appreciated. Because even as someone who doesn't have children, and I have a cat who I love very much, but I haven't felt the parent-non-parent divide either. Because I feel like that's another kind of thing you can kind of fall into, whereas people who

don't either want children ever or don't have them now feel like, like this company is only a time accommodating if it's for children. And which is like, that's great that they are. It's like at the same time, we should be respecting everyone's time and everyone's family, whether their family is just them and their roommates or their cat or just them. Like we should be respecting everyone's time.

Kaila Sachse (36:51.834)
Yes.

Kaila Sachse (36:55.482)
Yes. I'm so glad you said that. I feel like there's so much pressure, especially on women in their 20s and 30s and sometimes even like young 40s who are just getting bombarded with this messaging that if we don't have children, we're not providing value for some silly reason. It's ridiculous. And that's just the stigma that comes with being

Childless and so I'm so glad that you bring that up because as an employer, it's not only our duty to Lift up and support people with families, but also to lift up and support everybody who May not want a family or who isn't in that realm It's it's all okay. It's all okay because at the end of day like everybody needs to be treated like a team member a part of the culture and that also reminds me of a time when I

Meg Dalessandro (37:51.704)
Mm-hmm.

Kaila Sachse (37:53.787)
I was pregnant or my husband and I found out we were pregnant and we had a shared client, older male, and we felt the need to not disclose that we were pregnant despite like this ongoing contract that we had, partially because we were so afraid of how we were going to be treated now that we were expecting a kid. And I would maybe not even treated, but yes,

Meg Dalessandro (38:17.152)
Mm-hmm.

Kaila Sachse (38:22.329)
Yeah, I was definitely worried about maybe not even treated, maybe be perceived as not as hardworking. I didn't want to be perceived as distracted, uncaring about the work because none of that was true, right? It just now we have an additional role, an additional thing to balance. And, you know, looking back, I wish that we were forthcoming about that information because that would have reduced so much pressure.

Meg Dalessandro (38:28.636)
Mm-hmm.

Kaila Sachse (38:51.866)
But you know, like no matter how you spin it, maybe it would have been crazy. Who knows? Who knows? I think at the end of the day, like we need to treat people as the people that they are. That's it. Just like care about the person, care about the human, not get so caught up in the person's life, but just support them wherever they're at. You know? I don't know. I feel like that's like so airy-fairy, but it's important.

Meg Dalessandro (38:52.408)
Mm-hmm.

Meg Dalessandro (39:06.648)
Mm-hmm.

Meg Dalessandro (39:17.314)
Yeah, definitely.

No, I think that is really important because I feel I felt that way even just when I was applying to Wistia and I had just gotten married and like, you know, I, you know, I feel like a lot of people assume if you're getting, you know, you know, the old stigma or old way of doing things was like, you get married, you get the house and you have a baby and things like that. And so even in the back of my head, I was a little self-conscious of like, should I tell them I just got married? Like,

Kaila Sachse (39:44.152)
Mmm.

Meg Dalessandro (39:45.078)
If I say that I just got married, are they gonna be thinking, okay, nine months from now, you're gonna be taking time off or things like that. And so I've even dealt with that, even not even being pregnant or anything yet. And so I think that's something that a lot of people think about. And especially, I even see TikToks about it where it's like hiding my bump on my Zoom review or my Zoom interview because I think that it'll help my chances of getting the job. And it's so sad because it is, I mean, it's just...

Kaila Sachse (39:49.336)
Mm-hmm. Yeah.

Kaila Sachse (39:57.614)
Yeah.

Meg Dalessandro (40:11.274)
so true and it's I understand when there's like software companies or companies in general that are hyper growth you really need your people there etc but I noticed at least at Wistia like people you know multiple people from my team are you know could be expecting and taking time off at the same time and there's never any sort of like weird energy or like guilt around like

could you have planned this better so you guys aren't both at the same time? like, could you like, you know what I mean? Or like just weird like, like it's gonna be a stressful time because they're gonna be out. Like there's none of that. And it's so nice. Like it's just like, everyone just feels like, nope, we know when everything's gonna happen. Everyone feels really supported. We're gonna get backup support while they're out. Like we're all so good. We're so excited for you. And like, that's what it should be. And I think like realizing that also gave me another sense of like ease of like, okay, like not only do like,

Kaila Sachse (40:35.596)
Ugh.

Meg Dalessandro (41:01.494)
once you already are kind of in that scenario. But like once, you know, their policy is like, know, once you feel comfortable, you can let us know about like if you're expecting a kid and then you can kind of kick off the process from there. There's no like, tell us at this time so we can plan back this many months in advance or anything. So overall, holistically, I feel like Wistia takes a really good and like very human approach to becoming a parent because there are so many nuances in it. And it's like, all we can do is be human to each other. Like there's no like playbook.

Kaila Sachse (41:26.233)
Mm-hmm.

Meg Dalessandro (41:31.392)
There's no hack. There's no like perfect strategic way to go about being a parent and running a business or being in a business. And so I feel like we all need to be more realistic about.

Kaila Sachse (41:43.201)
Yes, yes. And newsflash for anybody listening who is concerned about hiring a pregnant person or hiring a parent. Just hear this. My team is almost entirely comprised of people who have children. And guess what? Company is still running. Company has been great. I've had people take maternity leave. I've had people who've had to step out for indefinite.

indefinite amount of time because they have something that they've got to take care of no matter what The company still runs right? I think it's it's more about how you're Implementing your internal practices to ensure that the company continues to run no matter what happens to who right? So if you have an issue with somebody stepping out I think the issue is really within yourself as the leader right you you have to look internal and say okay, I

What stigma am I attaching to this person for having a certain type of life? A. And B. What am I not doing within my business to help make it more sustainable in case somebody were to step out? Right? Because if you're totally relying your business on a certain somebody and then they step out and your business implodes, you have a much bigger issue. The issue isn't the person stepping out. The issue is your business leadership and the way that you've structured everything.

Meg Dalessandro (42:54.551)
Yeah.

Meg Dalessandro (43:03.479)
Yes.

Kaila Sachse (43:09.912)
Period.

Meg Dalessandro (43:10.316)
Yes. Yes. So snaps for that. Because I feel like it's so true because I think that often it's like as soon as you get hired, it almost feels like it's on you as the employee to have figured that out. Whereas if you took even a day out or an afternoon out, you're like, it feels like the whole company is going to collapse, which like realistically it never will. And if it does, then that's not

Kaila Sachse (43:13.973)
You know?

Meg Dalessandro (43:34.702)
really your problem. It's kind of like the person who started the business, their problem for sourcing it that way. So I think that's a really good point. Kind of a random tangent that just got me thinking on this is like thinking about parents and parenthood and things like that. Another reason that I know a lot of people, you know, take time out or rethink their careers is for taking care of their parents. And I think that's another really huge issue with like, you know, work life balance and even, you know, in past roles, I've, you know,

Kaila Sachse (43:40.44)
100%.

Kaila Sachse (43:54.806)
Mm-hmm.

Meg Dalessandro (44:03.448)
people I know have had to take time away to care for their parents and then they feel like, all right, this is me swan diving my career because I am prioritizing the people that matter most to me when, even if it is the highest point of your career or the most momentum you've ever had. And people will try to almost make you feel a little guilty about it of like, are you sure? Could you find another resource for them or something? But I think that's another part of the...

balance, like work, business, life piece that doesn't really get talked about much is like, not only taking care of parents, but also like when a parent passes or things like that. Like, that's, I don't know, like those are all like the human conditions that we can't just ignore.

Kaila Sachse (44:47.095)
Yes. Oh my gosh. Preach. It's so important. It's so important. Especially, you know, I think about how, and then we'll go into a little feminist tangent for a moment because this is important. I know you are. I know you are. That's why I'm indulging. So studies have shown that women make less than men. Surprise, surprise, right? And the dips tend to happen after having children, after taking care of

Meg Dalessandro (44:59.694)
I'm always here for it.

Kaila Sachse (45:16.663)
Parents and and why is that because women tend to be the ones to take the time off step away from their careers to do the things right whereas This this one blows my mind men end up making more money when they become parents there's I think it's just the way that we view men and women right we we view women as expected

Meg Dalessandro (45:35.137)
It blows my mind.

Kaila Sachse (45:43.231)
to take on those roles, whereas we view men as being the heroes for stepping up into those roles, being the babysitter of their own children. You know, so it's just, I don't know, that whole thing is mind boggling, but at the end of the day, if you are a business owner, it's really, really important that you evaluate how you are paying your team across the board. Are you?

Meg Dalessandro (45:49.698)
Yeah.

Meg Dalessandro (45:53.4)
Yep.

Kaila Sachse (46:11.367)
Unknowingly because sometimes people aren't aware of these biases that we have right? Are you are you unknowingly paying your your male team? More than your female team. Are you paying them more now? Are you giving them the the pay increase now that he's a dad and are you accidentally reprimanding the the pay of your your mother's the mothers who are on your team?

Meg Dalessandro (46:16.162)
Totally.

Kaila Sachse (46:38.26)
You know, maybe take an honest look at how you are handling that and pay is just one thing, know, time off is another thing, benefits are another thing. So I think it's really important to take a good, hard, honest look. If you, if you care about creating a culture that people want to stay in and work for, then these are the hard questions that you have to ask. Period. Period.

Meg Dalessandro (46:44.727)
Okay.

Meg Dalessandro (47:03.436)
Yeah, definitely.

Kaila Sachse (47:06.23)
That also reminds me, I want to a quick story. So I was, I think I was like 20, 23, 24. I was going on my first ever international vacation with my boyfriend at the time. And I, it was a big family vacation. I had asked my boss six months in advance if I could take the time off. And it really wasn't me asking her, it was me giving her the grace and telling her like, hey,

Meg Dalessandro (47:18.766)
Thanks.

Kaila Sachse (47:34.422)
In six months, I'm going to be taking this vacation. Just a heads up. And the instant response was no. Right, right, right, right, no.

Meg Dalessandro (47:44.418)
What? What, you can't plan six months ahead of time?

Kaila Sachse (47:48.72)
And so like I bring this up because we were just talking like if somebody is that pivotal to your business and they can't step out, there's an issue that that is a highlight right there. I mean, if she like wasn't able to do that six months in advance plan that far ahead, that's that's bananas. That is absolutely bananas. So that's just like one other way that we can support our team, right, is allowing them the time off just to recharge, even if they don't have anything.

Meg Dalessandro (48:08.664)
Yeah.

Meg Dalessandro (48:17.474)
Totally.

Kaila Sachse (48:18.545)
important to do like taking care of family members. Maybe people just need to relax. I don't know.

Meg Dalessandro (48:25.678)
Yeah, I mean, we already spend what, like 80 % of our lives working or some crazy statistic like that. It's like, we should be able to enjoy that other 20, 30 % and maybe even make it a little bit more.

Kaila Sachse (48:35.637)
Yeah, yeah, yeah, exactly. So, you know, okay, I do want to dive into your your freelance journey just a little bit. So it sounds like wrapping your arms around the money of it was was daunting, understandably. So how were you able to manage it over over that time? Because it sounds like you were running that freelance side hustle or business for what, a year or so?

Yeah, yeah. What did that money management look like by the end of it for you?

Meg Dalessandro (49:05.304)
Yeah, about a year.

Meg Dalessandro (49:10.946)
Yeah, I think in the beginning I was really disorganized. was taking invoices through PayPal and just doing that because it was like easiest fastest way to like set things up or like Venmo or whatever. And then after the first couple things, once I like started landing like a retainer client, I was like, okay, like I need to get like a legitimate like invoicing system set up. And so that's where I was like, all right, like how do I become a business? And so I actually used a platform called Zen Business.

And they helped me kind of just set up all of the LLC frameworks or like, you know, the paperwork and all of that. And it's like a very easy kind of software that just guides you through starting an LLC or whatever you need to do. And so that was one thing that really helped me make moves on it because I was talking to an ex colleague slash friend about when I was like, yeah, I think I might start this LLC. Like I'm getting all this, like, you know, I'm getting way more traction with this freelance work than I am trying to apply to these job listings where I hear nothing back.

after so many applications. And so my colleague friend told me about Zendesk, which is the one thing that I think really, really helped me out. And then once I got all of that paperwork sorted out, I went to Bank of America and I was like, all right, I want to open a business bank account. And I sat down with a very nice woman and she kind of set me up with everything and a business credit card and walked me through and I asked all of the dumb questions of like, okay, why do I need a savings and a business checking account?

And why would I also want like, why would I want like a business credit card? Like, how can I make sure my business expenses, I'm able to write them off easily. And I think for me, like separating my business money into a separate bank account really helped me stay on top of all of my taxes and everything ahead of time. And I decided to do like an account with ADP, which is like, you know, like a payment or payroll software where I could basically

I would get paid into my business bank account through like an invoice or whatever. And then from there, I would use ADP to like pay myself as an employee. And so I would take the taxes out of it before it would go into my personal bank account. And so that made it a lot, made me feel a lot more confident that I was one, charging enough so that way, you know, the taxes were getting taken out of it were like still leaving me with enough money to support myself and continue on. So it was keeping me.

Meg Dalessandro (51:33.12)
in check with like, my prices where they should be? And then also, it just made sure that at the end, when I did do my taxes, it was so much easier to collect all the information since it was in this separate bank account of like, all of my business expenses are on this card. So I can just export that as a sheet, give that to my like turbo tax person, and then they can kind of sort it all out. And then that's another thing I did is I used turbo tax to do my taxes with like a like a live person. And so because I had never done

small business taxes before ever and also had some, what was it? Like, you the company was kind of paying us after we got laid off. So some of those payments and I had a lot of different kind of incomes kind of coming from different places. So that was also really helpful. So my advice would really be to look for like systems and people that you can ask really dumb questions to. And I feel like you always feel like it is going to be a lot harder than it really is because

Kaila Sachse (52:30.281)
Yeah.

Meg Dalessandro (52:30.784)
Now that I think about it, I'm like, that whole process really wasn't that hard, but it is really confusing to know how to navigate it at first. And so I even, before I went into using Zendesk, I would ask ChatGPT, like, so like, how does someone set up an LLC? Like what forms would I need? Like, are there services that could help me do this? Or how, like where else can I learn more about why I should have a separate bank account? Or like, what do I do with my PayPal invoices at the end of the tax season?

things like that. Obviously you always just like double check those things, but I like using ChatgypT as a way to like ask my dumb questions to then help me think of smarter ways to ask the question. So that way it gets me to the right resource one way or another.

Kaila Sachse (53:13.074)
That is the coolest advice, chat GPT for getting those initial questions out. When I started my business, there was no chat GPT. I barely had a smartphone at that point. Yeah, that was a whole thing.

Meg Dalessandro (53:27.192)
Yeah.

Kaila Sachse (53:38.936)
separating out your funds, that's also really important. I co-mingled my funds for the longest and the bookkeeping was so much more intense than it had to be. All I had to do was like open up a Business Make account. I don't know why I was so stubborn on doing that, but anyway, after I ended up

Meg Dalessandro (53:50.189)
Yes.

Meg Dalessandro (53:55.758)
Because going to the bank is so annoying. It's like they're open for like two hours out of the day and it's like, it's ridiculous.

Kaila Sachse (54:00.306)
It's It's so true. opening, you know, I think what it was too is that opening a business bank account, usually they almost always charge a fee unless you have a certain minimum. And that was just annoying to me. Like I didn't want to have to worry about or think about, it's just more moving parts, you know? But eventually like opened up the business bank account and it's like kicking myself for spending all of the extra hours on bookkeeping when I didn't have to.

Meg Dalessandro (54:15.308)
Yes.

Meg Dalessandro (54:27.086)
you

Kaila Sachse (54:30.233)
You also mentioned forming as an LLC. It sounds like because you were doing payroll and they were taking taxes out ahead of time, were you an S-Corp as well? Did you elect as an S-Corp or were you just doing payroll? No. Yeah. Yeah. Okay. Okay.

Meg Dalessandro (54:30.593)
Mm-hmm.

Meg Dalessandro (54:46.19)
No, it was just straight up LLC with payroll. Yeah, with like me as a solo employee I try to keep it as like simple as possible And it was like every time I got a call with like whether it was a bank person or a tax person It was just like I made this money by doing this thing. How do I do it without going to jail?

Kaila Sachse (54:54.183)
Yeah, yeah.

Kaila Sachse (55:04.39)
Yeah, I love that. Yeah, I asked that question because obviously I am not a CPA. Ask someone who is much smarter than me at tax law and all that. if you elect as an S-Corp, you have the opportunity of using, well, you have to, you have to use payroll, but you have the opportunity of not having to pay as much.

Freelance, what is it called? Self-employed tax. So your tax liability is actually a lot lower if you're an S-corp. Now the caveat is, yeah, yeah, but the caveat is that you do have to go through payroll, which some people don't want to incur that extra expense and that extra step. And you want to elect as an S-corp only after you're making a certain income. Otherwise it just doesn't really make sense and you don't really get the benefit of it.

Meg Dalessandro (55:35.715)
Yeah.

Meg Dalessandro (55:48.782)
Yep.

Kaila Sachse (56:00.284)
That's just like a little like fun fact for anybody who's like thinking about forming their business and how to form it. That would be a question to bring to a CPA or maybe chat GPT. Although I think I'd prefer a real human who has some, some skin in the game. Yeah, I'd go to a real human, but, but ask them like, Hey, like how should, how should I form my business? This is what things are currently looking like. This is where I predict to go in the future. And.

Meg Dalessandro (56:14.986)
Yeah, I'd go to a real human for that one.

Kaila Sachse (56:29.603)
Here's the thing, if you ask somebody a quote unquote dumb question and they respond with a snarky answer, they're probably not somebody who you want on your team, that would be a good filter, right? But if they respond with kindness and they walk you through, they hold your hand, keep them, they're a gem. Yeah.

Meg Dalessandro (56:43.63)
Hopefully.

Meg Dalessandro (56:50.158)
Mm hmm. And people want to help you a lot more than you think. Like, I remember the service that I use ADP for the payroll. You know, some of it was a little confusing because I was like, never used a software like this before. And they had people constantly like checking in on me. I mean, at one point it was a little annoying. I was like, stop emailing me. But it was like they were checking in to be like, hey, like, because, you know, sometimes I'd run payroll, like, you know, once a month, sometimes it's like twice a month, kind of depending on like the flow of projects and work that I'm coming in. So they were checking in to be like, oh, like,

Kaila Sachse (57:01.551)
Yeah.

Meg Dalessandro (57:19.886)
Do you need help with anything? And it was just like so nice because I could again ask them really dumb questions. And they were like, no, that's actually a really good question. And then be able to like handhold me through it in a way. And so it was kind of nice to also, even though at some points it did feel like an extra hoop to go through for the payroll, it did end up giving me because I was just like a solo business person just thinking the stuff on my own. gave me like a sounding board, which I appreciated. So it's like it had its perks and its annoyances, but I overall am happy I did it because it did make my tax season a lot easier for me.

Kaila Sachse (57:34.523)
Yeah.

Kaila Sachse (57:41.606)
Yeah.

Kaila Sachse (57:45.071)
Yeah.

Kaila Sachse (57:49.425)
yeah, I made the mistake of not, so I didn't elect as a, as an S corp and I didn't use a payroll. So I didn't have my taxes set aside. And so I made that, that age old mistake that a lot of freelancers make and even new business owners make where I wasn't prepared for the, upcoming tax liability bill. And so that is another piece of advice. Like if you don't.

Meg Dalessandro (58:02.136)
Okay.

Kaila Sachse (58:18.03)
go through payroll and have that tax money accounted for. Make sure you have that savings account which you pretend doesn't even exist that you put money into every month or every couple of weeks, however often you are collecting on your invoices, and make sure that your tax liability is off to the side. So do a little research. You can ask Chad GPT this, what's my...

probable tax bracket. Again, a CPA would probably be better, but yeah, make sure you're prepared for that. Have that money set aside.

Yeah, yeah, but um, yeah. So Meg, where can people find you? You are currently working at Wistia. Are you still doing any like stuff on the side or no? Is that just completely off?

Meg Dalessandro (58:53.624)
Definitely good advice.

Meg Dalessandro (59:08.042)
So I have done a couple of projects just for like recurring, like I have like a

an author who I've worked on his personal brand a few times. So I updated a template for him or things like that. But I've generally just kind of wound down my freelance design video marketing business for now. You can go see my work at creative blob.com. That's the business website. And so I kind of have it just like open for later in life, but I'm not taking projects right now. But you can find me over on LinkedIn. I'm sure you'll share my links.

Or on Instagram, I post a lot of my roller skating stuff there. Or really on Substack is where you'll probably get the most me, I would say. Is once a month I send out one of those voicemail newsletters that can go to your inbox or you can just find it online and that's where I'll be.

Kaila Sachse (59:55.011)
That sounds so cool. I will definitely link everything in the show notes. Meg, thank you so much for sharing your thoughts with us today. I am so excited for how this is going to inspire employers in taking care of their team and new freelancers, business owners who are looking to start their own thing. So yeah, thank you so much for your time today.

Meg Dalessandro (01:00:16.354)
Yeah, thank you for having me. This was so fun.