Getting Time Back with The Squared Away Workforce with Michelle Penczak

Startups get the party. Startups get the party started. Startups get the party. Startups get the party started. You want tech and tacos, tacos and tech you know we got tacos and tech is on smash border green guacamole keeper countins counting beans Contador Quentan frijoles found us trying to raise some queso la vida San Diego school of rappy rapping fire tortillas round jalapenos in these modern times a crappy beer and coffee My coding yoga posse fold the body origami we be surfing coronado eating tacos El gordo, the taco stand in pesto lucha libre and sombrero Got a shout out to cost angels by the ocean watch the sunset la Hoya shores Entrepreneurs trying to get funded When San Diego Startup Week is popping in the summer Oceanside, the Tijuana esti be full of hustlers from couch surfing to penthouses right on the beach Tech leaders who believe stars are within reach we interview and founders who be shooting for the Moon SDTechOS with your host Neil Bloom. Startups get the party, startups get the.

Welcome to the Tacos and Tech podcast where we discover cutting edge San Diego technologies and the builders making it happen. I'm your host Neil Bloom, San Diego's tech ambassador and together you're going to put a face to the name of today's tech leaders with our own blend of local lifestyle. This segment is brought to you by Cox Edge. Our longtime partnership with Cox business has helped their engineering teams develop new tech products for small businesses and startups. Cox is investing in Edge capabilities and working with developers and engineers across the ecosystem to deliver ultra low latency compute solutions, helping customers to improve application performance and to reduce cloud transport and on premise infrastructure costs. Interested in hearing more about Cox Edge? Please visit coxedge.com and mention Neil Bloom or freshbroodtech.com for our partner discount. And welcome back to the Tacos and Tech Podcast. I'm your host, Neal Bloom. I am thrilled to have Michelle Penczak on the podcast, CEO of Squared Away. Michelle, thanks for being on.

Thanks for having me. It's good to be here.

Yeah. Not just be on the pod, but welcome to San Diego. I feel like we get to have a bit of a coming out party introducing you to the community. I know, I think I reached out to you on Twitter when I saw that you were here coming to town. Is that how we got connected?

I think so, yeah. I'm not a huge tweeter so I was like absolutely. New friend in town. All about it.

Love it. We're excited to hear a bit of that story, but do you want to give us a quick overview of what Squared Away is?

Yeah, absolutely. So Squared Away is a team of just over 200 military spouse, Chief executive assistants. We are all over the world. We have assistance from Japan to Poland and everywhere in between. And we essentially give people their time back. So anyone from a CEO of a major company to an independent consultant or just a mom who needs more time in their day, we are there to give our people their time back.

We love it. Time is the most valuable currency. So I think we're going to hear. Hopefully we'll get some tips out of you on this.

Yes.

But I am a new user of Squared Away, so I've been having a great experience with Taylor over the last few months. So thank you for building it for me to get my time back.

Of course.

But how did this start? Like, where are you from originally? And I want to hear the genesis story a little bit around this.

Oh my goodness. Well, it starts off like a bad country song to be honest. I grew up in eastern North Carolina. That actually comes into play because I swore I would never live there again, but grew up in eastern North Carolina, went to college in Tennessee, ended up in D.C. working as a personal assistant. And that's when the story gets really fun. Met my husband who is a Marine aviator and the never moved back to North Carolina came into play. He got orders to Jacksonville, North Carolina and I was like, great. Going to being a military spouse with arms wide open, going to embrace this new lifestyle and nobody wanted to hire me. I had all this great experience from working in D.C. and was very confident in my abilities, but kept getting the door slammed in my face. I couldn't even get a job answering phones at a law firm just because every time they heard military spouse it was like thanks Sia. No thanks. They wanted someone who was going to be with them long term. The interview would inevitably go really well and as soon as they heard that, they knew. I did not move to Jacksonville, North Carolina for the scenery. It was definitely for my husband's career. It was extremely frustrating. I job hunted for about eight months after moving there. I finally found Zirtual, which is another virtual assistant company. I began working for them and I worked with them for about two years and it was great. I became a manager. Loved what I did. I had phenomenal clients. And then in this is where the really Bad country song portion comes into play. In August of 2015, my husband had just deployed two weeks before. We were three months pregnant with my first little boy. And Xerchol literally shut down overnight. So I had a team of about 13 assistants who also didn't have a job. I was extremely upset because I didn't know what to tell my team, didn't know what to tell my clients. I had some clients who wanted to work with me outside of Xerchool. So they started working with me at that point in time because I wasn't going to let that beat me. I'm too stubborn for that. And I worked with them, literally. My husband says, until, you know, I put I would got that epidural for my son to come along. I took two weeks off from my clients and to become a mom. I know, I'm insane, right? I kept working with them and kept building up my clientele. And from there my husband came home in true Marine Corps fashion three months after having our little boy and said, get ready, we're moving to Hawaii this fall. So I had at that point in time about eight clients of my own that I had literally built from the ground up and was like, wait, hold on, you want me to move my east coast company, six time zones to Hawaii? You bumped your head, my friend. This is never gonna work again. I'm stubborn and would not let time zones beat me. Took a week off from my clients, told them I was moving, definitely did not tell them where because I didn't want to spook anybody and moved to Hawaii with my 10 month old and my husband. The only difference is when I went back to work, I was getting up at 3:00am and not 7:00 clock in the morning. But it actually worked out really well. I was working with my clients on the east coast from 3 to 11 Hawaii time every day. So I had all afternoon to play in the Hawaii sun with my baby. So it worked out really well.

It was just you at that point?

It was just me at that point. A lot of caffeine on board, not even gonna lie. But then one of my clients at the time, he was also building his company and about six months in to doing this crazy schedule, he called me and said, hey, I'm growing my company, I also need you to grow as well. And I was like, hold on my friend, I have a baby who's just over a year old and I'm already working crazy time zones. Like I don't know if I can do this. And I told him I'd call him back, thought about it for a few days and said, you know, What? I have plenty of friends who tell me all the time I want to be able to work, but nobody will hire me. But I've been able to bring this company, my own company, from North Carolina to Hawaii. Why not have them be the ones to help grow this? Calling back told him I was also crazy and would jump on this ship. And that's kind of where the roots of Squared Away were formed. And I said, if we're going to do it, we're going to do it with military spouses.

I love that. So he was saying, in a sense, you're supporting me, but I need more of more team members from you to support more of my team. In a sense, it was asking to staff up. Okay.

And I was like, I have no idea what building a company looks like, but I'll give it. I'll give it a shot. We'll see how this goes. And he kind of just put it all in my court and said, okay, let's see how you do it. And four months later, I brought on the very first assistant, Kelsey, who is now our director of operations.

Okay. The superstar that we know, Kelsey. So take us through a little bit of, you know, what was that like scaling? Because you'd managed the team before, right? So it wasn't like, brand new in a sense, in that regard. But now it was your baby. Right. So what was. How different did that feel?

Terrifying. To be honest, I didn't want to let anybody down. Number one, they were all invested in this idea with me. And it's a lot different when it's like you said, it's your baby and you want to see it succeed. So, you know, there was a lot of changes. You know, if something failed or something wasn't working, I always had that mentality of, if it's not working, we need to know so we can fix it together. Because I can only see one side of it. You guys can always see other pieces. So let's come together and figure out what's not working so we can change it. So there were a lot of changes at the beginning, even from, you know, looking back now, almost four years later. We changed so much to get to where we are now. But every piece was super important at the very beginning to make those tweaks.

I know working with my admin and many other people like Slack is a godsend, right? So we should be able to communicate. Have you been on. Have you built on Slack since the very beginning? In a sense, yes.

We have been on Slack from literally the very first, like, first handful of Squared Away assistants. We've all been on flag together.

Yeah, it's amazing to be able to build. Build a whole team, run a Run multiple companies just through it. Take us through a little bit, like, some of the stories you've heard from military spouses having opportunities, you know, through.

Squared Away, the biggest ones that come to mind actually happened at the very start of the pandemic. There was a family, this was in North Carolina. Before I ever left. I heard about this family. She had five kids, and she lost two of her kids to a very tragic ATV accident.

Oh, terrible.

And I was pregnant with my first little boy at the time. And I remember saying, I can't even imagine what that feels like. And my heart just goes out to her. And I remember saying so many prayers for her and her family over the next few months. And I never forgot about her. She would pop up occasionally just because the marine Corps is a very small community. And two years ago, right before the start of the pandemic, she applied to work with Squared Away, but I remembered her name. She actually applied and she didn't have a resume. I told Kelsey, I was like, just have her put one together. I want to see. I just want a glimpse. Because I believe that resumes are only a snapshot anyway. But I said, I just want a glimpse of what she's done previously. I did my interview with her and she was like, I just want an opportunity. I've never had an opportunity where someone has just given me the shot at just busting my tail to, like, give them everything that they needed. I hired her because I was that person I wanted. I was that person that was like, please just give me a shot to show you, like, I can kick tail, kick butt, or kick whatever you want me to. To just show you it's worth it. So I hired her in February. And three months later, she had done such an immaculate job with her client, he brought her full time on board with his company as his director of operations. And the impact on her and her family. And she wrote a whole post about it, but it was just. It was like. It just came full circle. And it was amazing that Squirt away was able to be a part of that and just watch something grow and blossom that I had never even dreamed could happen. And it was amazing to be able to see. And we're still in touch with her, like, even almost two years later after her client brought her on board. So things like that happen all the time, and it's incredible.

Yeah, I got goosebumps hearing that. That's awesome. So a few things related to that. You know, you're building a business. You're kind of building a marketplace. You got to find talent, and you got to find demand. How do you throttle and scale that at the same time? You know, like, how do you. What do you have an influx more of right now?

First of all, actually, we are pretty much always teeter tottering with clients and assistants. We have been incredibly blessed. We haven't had to market a whole lot for either one. Squared away kind of tells its own story on both sides of the house. I mean, you, Neil, as a client, have had a great experience as a client. So you want to tell people about squared away. Our assistants on the assistant side of the house talk to other military spouses and say, hey, this is not a legging or face facial company. That is an mlm. Like, you can totally build a career with them. So we have the best setup in the world. I feel like we have the clients telling our story for us. We have the assistants telling our story for us. We haven't really had a crazy marketing demand that we've had to do, but we actually have an abundance of both right now. So we're kind of always teeter tottering. It's a good problem to have on both sides, I think.

Yeah, definitely. But there's also this feeling of, I'm hiring the best, but the best could get hired away, which is great, right? It's a great story, but then you lose some of your best talent. Like, how do you plan for that?

So we definitely have processes in place, and we definitely want to celebrate the fact that assistants like Tiffany do get to be bought out and brought on board with those companies. But we also want to prep our clients for that happening and say, hey, you know, yes, Tiffany is leaving, but we have someone else in the pipeline. Because whenever there's the potential for that to happen, we start automatically looking internally and saying, okay, who do we have? Who are we bringing on board? Who is in our assistant pipeline right now that could potentially be a match if it were to, say, be a potential. And we have someone in the pipeline, but they're not someone we would want right now. We could delay that buyout process so that we could get them on board to fully be where they need to be before transitioning them out.

Okay, got it. So me being a client, I don't know if you. You want to answer this question, but how many assistants. How many clients would assistant be working on?

An assistant is capped out at four total. They are always capped out at four. Our assistants on average have two to three.

Okay, got it.

Yeah, we, we never have them overloaded. And I'm actually the reason behind that rule because I had, at my peak, I had 13 clients of my own.

Oh my God.

Yeah, I know I told you insanity over here. But I definitely had processes in place for each. And not everybody had the same demands. And there were clients that I only heard from like once a month kind of deal. But it's so that they can focus on formulating and building those four max relationships. Because you can't, you can't consciously put 10 people into great relationships. You can consciously focus on four good relationships.

Totally. What are some telltale signs that like an entrepreneur or a family like is ready or needs needs to help?

If you ever consciously think to yourself, oh my gosh, my to do list is crazy, or how am I going to get this done? Anything of that sort of. You can definitely delegate something to somebody. I always tell people, track your week. One of the things I get a lot is, well, I don't know if there's anything I can delegate. I have so much to do, but I don't know if I can delegate anything. Track your week. What are actual tasks that you're doing? Inbox management, scheduling, planning, Podcasting is something that a lot of our assistants work on. Project management. A lot of our assistants work in venture capital. Just helping with deal flow management and that kind of thing. So literally, if you can chat about what is on your plate, you can probably delegate a piece of it.

Interesting. Okay, so over the last year and a half, pandemic wise, gotta imagine needs have changed. What are any kind of interesting trends or interesting asks that you hadn't seen before?

We definitely had a lot less travel going on. We've had more people focused on self care and mindfulness and family life and, you know, how to be more present with their kids and how to time block better and how to be more present, you know, when they are working from home. I tell people all the time, you know, we work from home before working from home was cool. So there's all kinds of tips and tricks that we have like for working from home with your kids, working from home with your spouse. My husband still has not mastered what it's like to work from home with me. So there's all kinds of things like that we like to share with our clients.

Yeah, super helpful. Take us through coming to San Diego, which first of all, I think it's surprising it took you so long to come Here being there's a marine station here. But you know, take us through with that experience. How long ago, how have you been here and how's it been?

We actually landed in San Diego the day the Bonhomme Richard got set on fire in the harbor. So that's actually what we landed to was seeing the boat on fire in the harbor. Welcome to San Diego. And so we've been here just over a year. In the middle of pandemic. Moving with a 1 year old and 4 year old is very interesting. They like to touch and lick everything as much as possible. But I don't feel like we've fully experienced San Diego yet, even though we've been here for a year. My kiddos are in preschool and my 5 year old started in kindergarten this year. So it's been interesting. We have got to do a few things here and there, but I definitely feel like we haven't had the full experience yet.

Okay, well, to be determined a bit, we may be able to help there as well. From the audience, giving you some ideas of things to do.

A Padres game is definitely on my list.

Well, that just ended yesterday, the season for them, I heard. But if you're into soccer, San Diego loyal. They're playing through the end of October, so worth seeing, worth catching.

I will definitely have to look at that. My 5 year old is very into soccer right now.

Oh yeah. And they're in the hunt for the playoffs, so it's going to be fun. October is a good time. I think the season ends end of October. So San Diego loyal. Hopefully this episode goes out before then so that this is relevant. But. So 200 assistants now, where are you headed? Like has it been steady growth and where do you think you'll be a year from now?

Yeah, steady growth. We transitioned all of our assistance over this, the beginning of the year from independent contractors to employees. So everybody's an employee. It's a crazy process, especially with as many states as we're in. Hopefully this time next year we will have about 100, 150 more assistants. Fingers crossed. And then that many, if not double the clients. That's hoping. I'm a horrible guesstimator, but that would be my ideal. The sky's the limit. I just want to keep having us employ as many military spouses as possible because we're changing so many people's lives every single day and giving so many opportunities. I just want to keep that going and happening and giving everybody the opportunity to do what they want to do in life.

Yeah. Well, the employment piece is huge. You're giving even more stability now right on top of everything else. So keep building, keep building a great company for a lot of people. So congrats on that.

Thank you. We want to be around for a lot longer.

Absolutely. It's needed, that's for sure. So question San Diego question. Favorite taco spot. Do you have one yet? Have you been, have you found anything you like?

I do not. I've been to a few different places, mostly suggestions. I'm always up for them, but I don't have a favorite so far.

It's a very personal question. It's very controversial. Everyone's got a local favorite. I'll give you some tips of here's how to frame it out. So first of all, there's the right taco for the specific time of day. There's your breakfast taco spots, there's your midday quick lunch spots, there's high end dinner kind of taco spots and then there's late night drunk taco spots. So there's a whole bunch and everything in between. The safest bet is anything that ends in Alberto's usually fair game. We're talking Rigobertos, Aliberto's, all them. You'll get a pretty good taco or a California burrito app.

Okay.

We have a taco database that we have compiled for every guest we've interviewed on this podcast now. So we'll send that to you.

Oh my gosh, that's incredible.

Yeah, we're just starting to data mine and start to show the top five favorites. But I know one that just comes to mind all the time is the taco stand. They've got a number of locations around San Diego. There's always a line though. So some of our, if you listen to some of the episodes, they've got some secrets of how to jump the line a little bit. Call ahead or something like that. But yeah, taco stands. Probably one of the top most mentioned one, if not people using the cop out, that is going down to Tijuana and getting tacos there too, which that's fine. It's true. They have some pretty good tacos there too.

Yeah, I would love to check that out. I'm going to have to hop on this database there.

Yep, we'll get you a link for sure. But Michelle, thanks so much for sharing your story for building a company that's impacting so many on both sides, helping me, the business owner, but also helping so many families stay connected and employed. So thank you. Appreciate it.

Thank you very much for having me. It's been such a pleasure.

Likewise. Thanks for joining us on the Tacos and Tech podcast with Neil Bloom. Thanks again to Cox Business for helping make this possible by expanding the reach of the San Diego tech ecosystem. Big shout out to School of Rap for our rad intro music and this podcast is edited and mixed by Patrick Norton at citizenrecording.com you can find Neil Bloom on Twitter eelbloom and on LinkedIn as well as well as fresh brewed tech and tacos and Tech Pod on Twitter too.

Party started. Startups get the party. Startups get the party started. You want decking tacos, tacos in tech, you know we got it.

Hey.