EA Delegating w/ Michelle Penczak: Founder of Squared Away - Military Spouses becoming Top Tier Virtual Assistants
Today, my guest Michelle Penczak is teaching us everything there is to know about executive assistants (EAs) and how to better delegate so you can make the most of your time.
Michelle, with previous podcast guest Shane Mac, co-founded Squared Away, which provides EA services to companies and individuals. The company is unique in that they exclusively hire military spouses and provide flexible and remote employment opportunities.
I’ve recently hired an EA -- one of the highest leverage things I have ever done. I am on a mission to learn and share how to become a better delegator and how to build a better partnership with an EA. Michelle shares how Squared Away got started and talks all things delegation and EAs during our conversation.
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Here’s what I learned from the episode:
Squared Away is a full-spectrum support system, helping clients with everything from high-level C-suite tasks to everyday household management tasks.
They serve a wide range of clients, VC firms, Startups, and Professional Services.
About 25% of Squared Away’s clients have never worked with an EA before.
The highest volume of tasks EAs help with are research, travel planning, and scheduling.
Making the most out of hiring an EA is not just about being able to delegate, it’s really about building an effective partnership for both the client and assistant.
When to get an EA? If you are thinking about work more than your family when at home, it may be time to get some support.
If you are just getting started with an EA, it is best to start small. Being a delegator is a learned skill. Starting small gives you the least amount of risk and the most bang for your buck.
The best clients are great communicators.
The unemployment rate for military spouses is at 38%. During the Great Depression, the country’s unemployment rate was 24%.
Hiring EAs for a company is an awesome perk for employees.
The most challenging thing for Michelle when she switched from being an assistant to being CEO was learning that she didn’t have to do everything herself. (Irony!)
A lot of people don’t realize how much time goes into small tasks (like checking email.)
Military spouses are extremely resourceful and have a supper supportive and far-reaching community.
Learn more about Michelle Penczak:
Additional episodes if you enjoyed:
Episode Transcript:
Michelle Penczak: Track yourself one day, checking your email. Every single time you check your email, track how much time you spend checking your email and add it all up and say, holy cow, I spent four hours in my email today. I could have given this to an assistant and saved myself four hours.
Eric Jorgenson: Hello again, my friends, and welcome to Jorgenson Soundbox, the sandbox of sounds. Here I try to share absolutely everything that I learn that might become useful to you. In the past year, I have hired a full-time EA, that's an executive assistant, and it's been one of the highest leverage things I have ever done. And now I'm kind of on a mission to learn everything I can about how to become a better delegator, a better user of EAs, learn everybody's EA playbook, all the high leverage tasks that they're delegating. And that's what this conversation is all about. Michelle Penczak is the co-founder and CEO of Squared Away, which provides EA services to companies and individuals. They're unique and interesting because they work on the assistant side exclusively with military spouses and provide this wonderful, flexible employment, which makes a wonderful fit with a remote assistant lifestyle. If you love this conversation and want to be a part of this community that thinks a lot about leverage and how to accomplish more and achieve more, we talk about this stuff all the time. I write about it. I’ve got a course about it. Just go to ejorgenson.com. Join the newsletter. You'll get everything you need. And I hope you enjoy this conversation, take something away from it, and feel a little bit more confident experimenting with leverage, delegation, and EAs in the future. Thank you for listening.
We'll return to the show right after two quick messages. I want to tell you first about one of my favorite discoveries of the past few months, the Founders Podcast. David Senra, the host, is a biography reading machine. He's read hundreds of entrepreneurs’ biographies from all across history. And his podcast is him talking about everything that he's learned, his notes, quotes, and key insights from each book. He was masterful about pulling these key insights out, connecting them to other biographies. That's my favorite aspect. He's made connections between Steve Jobs, Nolan Bushnell, Charlie Munger, Andrew Carnegie, Lucille Ball, and these far, far reaching biographies that he has read. He is an encyclopedia of knowledge. And if you don't have time to read the thousand-page biography that Walter Isaacson writes every three months, learning from David's high quality recaps that he does in one or two hours are absolutely the next best thing. This is a paid podcast, and you'll get access to the whole back catalog with hundreds of episodes, I think about 250 right now, for $99 a year or lifetime access for $299. I've listened to a dozen episodes by now and just last night finished another one, the General and the Genius, which is about the partnership between Grove and Oppenheimer which made the Manhattan Project successful, birthed the atomic bomb, ended World War II, and create the atomic age. It was very interesting, something I knew nothing about. It was a very efficient and interesting story that David took us through. Learning through biographies is something that two heroes of mine, Charlie Munger and Mark Andreessen, both advocate constantly. It's something I love to do. And Founders Podcast is a great way to get those lessons in a high signal way. Go to founderspodcast.com to learn more and sign up. You can listen to 30-minute sample episodes there or purchase the paid feed. Again, founderspodcast.com. And it's the first link in the show notes. Thank you so much for supporting the sponsors who help make this show possible.
Another way to support the show, have some fun, and be a part of the action in our lives is to invest alongside me and my partners in startup and early-stage tech companies. I started an early-stage investment fund this year called Rolling Fun with two of my most talented and trusted friends. We've been angel investing for years and managed to fund a few billion-dollar companies along the way. And now we've started a fund which lets us work with you to invest your money alongside ours into some of these companies. We will be investing in the most promising early-stage tech companies we can find all around the world. So far that has been stuff like a demand layer for e-commerce, a robotic drone AI company for building walls and structures, and – what was the most recent one? – oh, a water management rights company. Super interesting. We've got podcast episodes about these. If you love sort of thinking about early-stage technologies and how to deploy your capital more efficiently, you can check that out. We've got podcast episodes with me and Bo and Al where you can learn more about Rolling Fun. I’m always taken meetings with investors, and I'm honored that many of you listeners have already joined the fun as co-investors. You can learn more at rolling.fun, which is linked in the show notes, and accredited investors can apply and invest with us through Angel List today. I'd love to talk to you if you have more questions or just want to learn more about it. Now, on with the show.
Michelle, it's so nice to finally meet you. Thank you so much for making the time to do this. I've heard of mountains of good things about you, and it's a pleasure to finally talk.
Michelle Penczak: Well, thank you so much, Eric, for having me come on board.
Eric Jorgenson: I have an infinite appetite to learn everything there is to learn about EAs and delegation and getting better leverage for our time. And I feel like you’ve got to be one of the smartest people in the world about that, and so I'm very excited to have you here to like brain dump on us and tell us all the things that we're doing wrong or not doing or could be doing to be like delegating and EAing and everything better.
Michelle Penczak: Well, I am happy to share the knowledge. I don't know that I am the most- one of the most smart people on the planet, but I'm happy to share what I know.
Eric Jorgenson: Okay. So, well, give us some context. You are the CEO and co-founder of Squared Away, which is- how would you present that?
Michelle Penczak: We are a team of military spouses. We are based all over the world. We can pretty much handle anything from high-level C-suite executive assistant tasks to personal administrative assistant tasks, everyday household management tasks, just things you want to take off of your plate that you want to delegate and give away, and pretty much everything in between.
Eric Jorgenson: So personal and professional. Is there any separation from your perspective between those two things or are you just kind of like anything we can do to help the busy people give it to us?
Michelle Penczak: Pretty much anything we can take off of your plate and make the whole client less busy.
Eric Jorgenson: Got it. Okay. A very holistic whole lifestyle approach. I like it.
Michelle Penczak: We are a holistic support system.
Eric Jorgenson: Beautiful. And how many military spouses are a part of Squared Away now?
Michelle Penczak: We are just shy of 300 right now.
Eric Jorgenson: That's awesome. That is huge.
Michelle Penczak: I am amazed every single day at how far we've come over the past four and a half years.
Eric Jorgenson: Four and a half years, yeah, that is a lot of growth. That's remarkable. And it's got to feel incredibly good to provide all those jobs.
Michelle Penczak: I have to pinch myself every single day. I mean, based on my background, I always wanted people to take a chance on me, and we've been able to take a chance on almost 300 military spouses, which is incredible.
Eric Jorgenson: That's amazing. So, is it fair to say that there's also 300 clients? No, you've got more clients than that, right? Because it's one employee supports multiple people.
Michelle Penczak: Yeah, our assistants don't support more than five clients. We have around 700 clients right now, give or take.
Eric Jorgenson: Also amazing. Potentially even more amazing than- yeah, in four and a half years. So, you've got this perch kind of over hundreds of relationships between founders, executives. How would you break down your clientele? Like, who do you support the most often?
Michelle Penczak: Honestly, we see a lot of CEOs of startups, individuals who are consulting, we see a lot of high-level CEOs of all types of businesses from very small e-commerce platforms to, oh my gosh, I can't even think of all of them off the top of my head. There's just such a wide dynamic. Venture capital firms, we're supporting them internally, just helping them with their due diligence process, which is absolutely incredible, something I never saw our team really focusing on. And then, they're also handling project management for companies and teams for smaller companies as well. It's really interesting how dynamic the support systems are.
Eric Jorgenson: Yeah. That is incredible. I mean, it's got to be as many individual roles as there are clients; everything ends up super, super specialized.
Michelle Penczak: 1000%. There are pockets of clients and then it's even more individualized in the pockets.
Eric Jorgenson: I mean, how do you prepare your staff for the potential of doing a completely unique job for each client being different?
Michelle Penczak: So, the way we kind of break it down high level internally is we give them an idea of the type of client they're supporting. For instance, I'll pick on VCs just because it's fun to pick on VCs a little bit.
Eric Jorgenson: Oh, yeah. That's half of Twitter.
Michelle Penczak: But take working with VCs for instance, they could be doing due diligence or companies that are potentially being pitched to them. They could be organizing decks. They could potentially be viewing decks. They could be looking into founders on LinkedIn. They could be tracking all of that. They're scheduling meetings. And that's at a high-level, generalized aspect of what a lot of our assistants are doing. But then on the flip side of that, each VC that they're supporting also has potential personal tasks, travel, and a multitude of other things that they're being supported on that we don't know exactly because that's those partnerships that are between them and their assistant.
Eric Jorgenson: All right, Michelle, what are some of the highest leverage tasks you've seen? I know you get this amazing view of all of these things kind of put together and I'm hoping you can tell us what are the things that we're not doing that we should be from a delegation perspective.
Michelle Penczak: Yeah. So, some of the highest volume of tasks that I'm seeing are planning, research, travel planning and scheduling. Those are the three biggest things that I'm seeing, but I'm also seeing forward planning. So that's something I like to break down as seasonal planning. And as a parent, what I see is, for instance, it's April right now, so parents are planning for summer. You have summer vacation, you have summer break from school. Kids are out, you have to plan for camps. You have to plan for fall, if kids are going to a new school. We support a lot of military families. So, they're traveling from different duty stations, so they're looking at new schools. A lot of them are going to be looking into activities for their kids. So, while the assistant is also supporting the client professionally, they're also supporting them on the personal side as well. So, they're helping them keep a lot of that organized.
Eric Jorgenson: Yeah. That future planning I feel like is something that people don't think they can outsource very effectively and might be surprised to find out, I mean, how much research there is, especially in this case where you're moving around a lot or where you're traveling or increasingly as people are sort of nomadic or working remote, like there's so much that goes into that, so many logistics.
Michelle Penczak: I think a lot of the issue is most of us, myself included, will get in the mindset of this is such an important task, this is something I personally really need to focus on for my family or for me personally, and I really just can't outsource that to anyone else. But if you have someone doing the groundwork for you, then you've effectively removed 50% of the choices that don't even apply to you. So, you can really focus your time on the choices that do apply to you and your family.
Eric Jorgenson: Yeah. How do you coach people through that? I imagine that's a lot of the job, especially on the client side, like even once you sell someone on like, hey, I need an EA, getting them to use it and trust someone else to contribute to their life.
Michelle Penczak: I think it's all in the approach to working with an assistant. So, with working with someone from Squared Away, it's really not just delegating to someone, it's really building an effective partnership. Someone who is your right hand, they might not be in the same state as you, or even the same country at some point. But really being able to say, oh my gosh, my life might feel like it's falling apart right now, but I can message my assistant and say I need this by the end of the day, please help me. And you know it's going to happen. And you know that you're going to get someone who truly cares about you and your experience. You might not get that from another service, but our assistants, one of the things that is really important to us in building that relationship is you're building a relationship. This is someone that you want to get to know. They're not just a task on a to-do sheet. They are someone that you really want to form a professional relationship with and be with long term because you don't want a relationship where you dread going to work every day, you dread receiving tasks from them every day. And you do want an effective partnership on both sides of the coin.
Eric Jorgenson: How long do you see the typical relationship between an assistant and a client?
Michelle Penczak: The average relationships at Squared Away are around 18 months.
Eric Jorgenson: Oh, that's amazing. So, you really do- It's not like you're getting rematched with somebody all the time and it's not like you're throwing tasks into this kind of pool of people who are willing to help but changing context all the time. Like you work with the same person week after week. Interesting. So, how much- I imagine that is tough context switching on the assistant side to work with you said they support up to five people.
Michelle Penczak: Yeah, not everybody supports five clients though. We have assistants who are supporting, I honestly think there's only a handful of assistants who support five clients, and they're very much plan levels, but most of our assistants are supporting around three.
Eric Jorgenson: And just kind of working five to ten hours a week for each one?
Michelle Penczak: I really wish I had a good average or an assistant in front of me. But it's so varied because our assistants, the minimum that they work with us is about 75 hours per month, which is very part-time. And then we have assistants who work with us full-time. So, it's very much varied within those 300 assistants.
Eric Jorgenson: Okay. That makes sense. So, talk me through bringing a client on. Like how does someone know when they're ready to be working with an EA?
Michelle Penczak: When you find yourself feeling overwhelmed. If you- and just speaking from personal experience, I'm a mom. I have two boys. When you find yourself thinking about work more than your family in the evening, when you find your boundaries, which I firmly believe in having family and personal boundaries between work and family, when you find yourself thinking about work when you should be thinking about your family, when you find yourself feeling frazzled and overwhelmed, you need support. As much as everybody wants to be Wonder Woman and Batman, not everybody can do it by themselves. It took me such a long time to realize as much as I wanted to do everything myself, I couldn't, and that's a hard pill to swallow. But once you do, it's so amazing, even if you want to give away five hours of tasks per month, even if it's just saying here, reorder my last Instacart every single week for me and help me do that. It's so empowering just to be able to say, you know what, I have this time back, and now I can focus on something that is more appealing for me.
Eric Jorgenson: Yeah, I imagine that's a very interesting- like something that I like about Squared Away is the ability to start small. It's an intimidating thing to start working with an EA. You're not sure how to start and you're not sure what to- how to build trust, what tasks to give first, if you're going to be any good at delegating at all. Like it is a skill that both sides have to build. Even if you're working with an experienced assistant, you need- on the client side, I had to learn how to do this and what things I could delegate and how to be a good delegator in the first place. So yeah, this ability to kind of start small. I mean, do you see that often? Is that the journey that people kind of start with, 5 hours a month and then go to 20 and then go to 50?
Michelle Penczak: Yes. I tell people all the time, if you have no idea where to start, please start small. It is such a journey and a learned experience. Being a delegator is a learned skill, and it's not something that everybody comes equipped with right out of the gate. Being able to delegate doesn’t mean you are fully equipped to give away an entire task. It might just be one piece of one part of a task. And I had this conversation with a client a few months ago because he was feeling like, oh, I don't feel like I can give anything away. And I was like you don't have to give the whole task away, just give a piece of it. Because that one piece is going to help you complete the entire pie. So, if you look at it in blocks, then eventually you are going to complete the house kind of deal. And I love analogies, so I apologize in advance. But starting small is going to give you the least amount of risk, and it's going to give you the most bang for your buck, in all honesty. You're not going to waste time or money.
Eric Jorgenson: What do you see as the behaviors that like what you would call a good delegator has? Like how do you know a client is going to be great to work with for an assistant and successful at using Squared Away versus somebody who's like, oh, this is going to be trouble?
Michelle Penczak: Communication, a great communicator. And by great communicator, I don’t mean being able to make every call all the time. I mean someone who is just very consistent in saying, you know what, I'm putting a call with you for 15 minutes on my calendar every single week just to brain dump what is living in my brain and what is stressing me out at night. That's a good communicator. Hey Michelle, I've got to tell you this is what kept me up last night, here's all my tasks, help me prioritize them. That's a good communicator, because number one, you're letting me know what's happening in your life and what I can take off of your plate. And then I can help you prioritize that moving forward. And being consistent with those meetings or each week, those calls every week means that you're a good communicator with me and we can work up from there.
Eric Jorgenson: Let's talk about like the peak delegators. Who are the very best? What are they delegating? What are some of the most complex tasks that assistants are taking on?
Michelle Penczak: Oh, my goodness. We have clients who are going through fundraising rounds and who definitely- as founders. They need support from their assistants to keep them organized because they're doing another full-time job on top of their full-time job. And they need someone to help keep the documents organized. They need meetings done instantaneously almost. They need LinkedIns pulled, the whole nine. So, all that goes into a fundraising round, they need that support on the backend. So, our assistants are assisting with those. That’s the most complex I’ve seen.
Eric Jorgenson: Yeah, and that is a very high trust environment. I mean, you've got private data. You've got schmancy people. You've got fast moving environments, and you do not want to go into a meeting with the wrong prep or the wrong numbers. Yeah, every digit counts when you're sending that paperwork around.
Michelle Penczak: Absolutely. It's incredibly high stress for the client. It's incredibly high stress for the assistant doing the support, and everybody just has to come together and breathe during that process. I think that's the most complex and intricate one I've seen our assistants work on.
Eric Jorgenson: Okay. And that, I mean, it goes with a variety of clients that you have. What are the other things that come to mind, like process wise? Who are the clients that you see with the most hours or the most support from their assistant? Like, how far does that go?
Michelle Penczak: I can speak to delegation. We have some really good delegation tools that our assistants are working with. So, a lot of our clients will work with Asana schedule, deadlines, that kind of thing. Those are the top tier delegators that I've seen who will have-
Eric Jorgenson: That have a project management tool already that they kind of use.
Michelle Penczak: Yep. They have the project management tool, they have feedback that they're ready to give their assistant, they have that scheduled call where they'll go through the task list together, and then they'll give feedback on tasks. And I would say those are the master delegators that I see. And quite a few clients will come up with that when they're ready to get started. But then we'll also get the ones that are like, oh my gosh, I have no idea where to get started, can you please just fix my life right now? And then that's when we'll suggest and recommend tools to get started with.
Eric Jorgenson: And you like teach them to use Asana on the client side and you're like here's what the best people do, why don’t you get organized this way?
Michelle Penczak: And then some clients will also say I'm not tech savvy. Can we use like Google docs, just collaborate on Google docs together? A lot of it is preference, like what's going to work best for you. And I'll pick on myself and my husband. I love Asana. My husband cannot figure it out for his life at the moment. That's why we personally use Trello as a family. So, I mean, it's to each their own.
Eric Jorgenson: Yeah, absolutely. How often does that burden fall on like the assistants? Do to the Squared Away assistants come in with like a background in this and knowing that they're going to have to kind of train their client to use them? Or is that something that like you take on as Squared Away and be like you do not have to have this experience, we will sort of forge the connection between you and make sure that this is a smooth partnership?
Michelle Penczak: So, that's kind of something that we teach our assistants as part of being proactive at Squared Away. Through training, we will teach our assistants a lot of times your clients won't know how to delegate. They won't know how to stay organized, offering them different platforms, different ways to stay organized. You can offer them- ask them their preferences. What do they like to see? Do they like end of day breakdowns? Do they like Google docs? Do they like phone calls? Do they prefer Zooms? It's all in that first phone call with your client where it's basically an interview of them saying, okay, this is me getting to know you. This is our professional dating moment. And I'm going to get to know you, and now I'm going to work with you moving forward and see what's going to be best in supporting you.
Eric Jorgenson: That's super interesting.
Michelle Penczak: It’s really not PC, but it’s definitely like professional dating.
Eric Jorgenson: Yeah, it is an apt analogy. And as you say, if you're the master of analogies, that is a good one that we can all relate to. I've enjoyed some of the blog posts that you guys have written, too, about how to become a better delegator and separating good from bad. And it talks about some of the same things that I talk about in building more and more personal leverage. There's a clip from, I can’t remember the name of the post. I think it is how to become a master delegator- How to Become a Bad-Ass Delegator, even better title, but the quote is “It's not whether or not you can complete the task on your own, but to ask yourself, what's the return on investment by doing so.” That's so like just training people, which I had to do myself and it sounds like you did too. Like pull out the I can do it from the is it the most important thing to do, and learn to- just because it needs to be done doesn't mean you have to do it and telling yourself over and over again is this the highest and best use of my time. Who else can do this work other than me? Which is so hard for- I bring the Midwestern work ethic of whatever it is, I can do it. I can fit it into today. I can fit it in tomorrow. Like I'll get everything done. And it's just so much more rewarding- so much more relaxing to know that you have some help and have somebody else bringing you along. And when you realize you're creating a job for somebody who needs one and loves doing it, it's not like you're just making work for other people to do for free and asking for favors all the time. Like people want to help you and you want to be helped. And if you can afford to pay them for that help, it is a wonderful mutual win-win that we should all be excited about.
Michelle Penczak: Absolutely, and it's so funny that you say that because we had a manager call internally last week, and one of our team managers, she was talking about how awesome it was to have her husband come home from flying. He's a pilot in the Navy. And she was like it was so cool to be able to say, hey, guess what I helped my client with today and how bad ass is that. By the way, that's way cooler then you going flying today, I'm sorry. It's amazing that we're able to do that because 10 years ago when I met my husband and we got married, that just was unheard of for military spouses to be able to work remotely in that capacity. So, we've kind of changed that narrative a little bit.
Eric Jorgenson: Absolutely. In doing my research, I found that – I think it was on your site, so I'm not telling you anything you don't know – but that military spouse unemployment is at 38%.
Michelle Penczak: 38%, yes.
Eric Jorgenson: That is insane.
Michelle Penczak: I agree. It is.
Eric Jorgenson: That is so brutal. And you said 24% pre COVID, which you would think that equalization of remote work would make it easier to kind of close that gap, but that is unbelievable. And yeah, I mean, the fact that this company and everybody who's a customer of it is helping to kind of eliminate that is hugely meaningful.
Michelle Penczak: 100%. To kind of put it a little bit in perspective and share a little bit more, the unemployment rate during the Great Depression as a country was 24%. That hit and hurt.
Eric Jorgenson: Extremely rough. Did you struggle with this before starting Squared Away? Like is that what drove the creation of the company?
Michelle Penczak: It played into it a lot. I married my husband in 2013. And we were in North Carolina, which is where I'm from. So, I felt like I had a leg up. I knew the area. I was in a great setup, for the most part, for being able to find a job. And nobody wanted to hire me. I went on probably 30 interviews. They would all go great until I got the question, what brings you to Jacksonville, North Carolina? If you're from the area, I guarantee it's not the scenery. And my husband's a pilot at New River. Oh, that's cool. And it would instantly do a 180 and I wouldn't hear back. And it wasn't like I wasn't qualified for the positions either. I had a really great resume, and I was qualified to answer phones at a law firm. So not hearing back didn't make sense to me. And then once I started learning a little bit more about the military spouse community, it was very obvious that it was because I was a spouse, and I was only there temporarily.
Eric Jorgenson: The concern is that they hire you and you get forced to move away in 6 to 12 to 18 months, and they're back where they started.
Michelle Penczak: 100%. They wanted someone long-term.
Eric Jorgenson: Yeah, brutal. And yeah, I mean, the rise of remote work hopefully helps that massively. So, it's a perfect position. So, when did Squared Away become a real company and a mission for you?
Michelle Penczak: Squared Away came a few years later. I was extremely fortunate and I started working with [inaudible 30:55] in 2013. So remote before remote was cool.
Eric Jorgenson: Hipster remote.
Michelle Penczak: Yes. And I worked with them for about two years, made it to a manager position. And I was there when the bottom fell out in August of 2015. And that's when my sad country song story starts. I was three months pregnant with my first little boy and my husband had deployed three weeks previously for six months. So, it really is a sad country song. So that's when I was like I really have this opportunity to take my clients and continue to work with them, and they agreed to do so, and we had that option. So, I kind of took that opportunity and ran with it. And worked up until my husband says I put up my out of office email when they were putting in the epidural kind of deal. He might not be wrong. I took a grand total of two weeks off to become a new mom. Don't recommend. Do not recommend at all to those who are listening. And then I worked remotely with my clients, and it was hard. It was extremely hard. It was just me. That's the reason I took two weeks off was because it was just me. And a few months later, my husband came home and said, hey, we're moving to Hawaii, thanks Marine Core. Most people would be excited. I had a moment. We're on the East Coast and my business at that point had 13 clients and it was just me. All were east coast based. So, a little bit scary, but I kind of made up my mind that I wasn't going to let time zones beat me, so that wasn't going to happen. So, I tell my clients, I was taking a week off to move. I did not tell them where because I did not want to terrify them. And I moved to Hawaii and started waking up at 3:00 AM, sponsored by coffee.
Eric Jorgenson: They have great coffee in Hawaii.
Michelle Penczak: They do. It is phenomenal. Shout out to Kona. I worked from 3 to 11 everyday Hawaii time. And that's when, after about six months, that's when the idea for Squared Away was born.
Eric Jorgenson: And how did it turn from you doing octopus work from the middle of the night and like servicing 13 clients by yourself to- I don’t know, would you think of it as an agency today or a company? I guess I don't know how you'd classify, but turn into a like okay, no, I'm going to grow the team, I'm going to match with other people, I'm going to build a real business out of this, not just a solo shop?
Michelle Penczak: So, my co-founder Shane called me one day. I believe he was at South by Southwest, and he said to me, he goes, “You need to scale because I'm scaling.” And I was like, “Yeah, I have a one-year-old, Shane, call me later. I don't know if this is a good idea.” And then he called me back later and we had a conversation about it, and he was like, “No, this is great. You're a good assistant. You could scale and do more” kind of deal. And I said, “Well, let me think about it.” And I had friends who had asked me for a few years at that point like how can you work from home? This is something that I would love to do, how do you get into that? Well, this was a good idea for them to get into that at that point. So, I called him back and I said, “If we're going to do this, we're going to do it with military spouses in mind. That's going to be the focus.” And that was March of 2017.
Eric Jorgenson: Whoa. That's awesome. And Shane had been a client of yours for the run-up, for the past few years or past few months. So that was how you guys got to know each other and yeah. And you scaled together.
Michelle Penczak: He’s been an amazing mentor.
Eric Jorgenson: Yeah, and to me too. This is this Shane Mac that we're talking about, who is also a previous episode on this podcast and who I've learned a lot from in business and life and more particularly in crypto. We spent most of that episode talking about crypto and not enough talking about Squared Away. So, we're here to balance the scales and talk about more of this. But I know that has been a key piece of Shane's life and how he's managed to be an investor and a founder and a country music star all at the same time, which is a unique life. So, yeah, that's remarkable. What was sort of the division of labor in the beginning of the company? How did you guys work together and what was the zero to one moment or one employee to ten employees?
Michelle Penczak: So, in the beginning, it was more Shane was helping me kind of drive the idea for bringing on clients, supporting military spouses kind of deal. That's how we got from like one to ten. It took us about a year to get from one to ten. But then when we officially launched in November of 2017, there was only two employees. It was just me and Kelsey, our Director of Operations now. So, at that point, I think we had about eight clients, if I'm not mistaken, in 2017. So, it took us about a year to bring on ten people, ten employees.
Eric Jorgenson: Yeah. And then just keep- add a new client, add a new assistant, two new clients, two new assistants. Try to keep everything balanced.
Michelle Penczak: It was very much a teeter-totter effect.
Eric Jorgenson: When you're panicked about one thing, the other one's fine.
Michelle Penczak: Exactly. It was very much like, okay, we're going to panic over here for a second, now it is time to go panic over here. That playbook of the first year, I don't know that I could write it effectively for what it is worth.
Eric Jorgenson: Super interesting. And one of the other interesting things that is unique about Squared Away, just looking at the homepage, is that it's really focused, at least on the client side, on being a company perk, which I've looked at a lot of EA companies and I have not seen anybody else really hit as hard as you guys do on really selling to whole companies or whole executive teams all at the same time. And this is a drum that Shane has beat for a long time that I think is really wonderful. It's such a great perk to give people parts of their life back and help them unlock valuable hours to spend with their family or stop thinking about work when they should be thinking about family, to reference your boundaries again, because that is just so, so important. And I'm curious where that came from and how it came about and how it's maybe unfolded for you.
Michelle Penczak: So, Shane actually implemented this when he was CEO of Assist. And I was actually the company perk because I was the assistant that was supporting Assist when his team was growing. But when that was implemented, everybody had such a great response. It was like, oh my gosh, this is great. Like one of his team members had me book a Disneyland trip for her and her kids and book doctor's appointments and things like that so she could focus on sales and that kind of thing. So, it was really great. There was a wonderful response from the Assist team when that was implemented. So, coming from the backside of that and actually working on it, the team responded really, really well to that.
Eric Jorgenson: That's fantastic. I mean, I remember Shane talking about how impactful that was for recruits and everything. It's just, in an era of like ping pong tables and stuff, that is just so much more employee focused and employee friendly.
Michelle Penczak: It was really cool to watch in all honesty because when people were onboarding at Assist, they had an onboarding process, and then part of the onboarding process was they got to chat with me and learn about how I can support them. And it was really just cool to meet everybody and say, hey, here's all the cool things I can do for you that is not work related. So it was really neat.
Eric Jorgenson: Yeah. Do you still use that like menu of options or procedures or things you can offer?
Michelle Penczak: Yeah, it's actually part of our delegation guide that we share with all of our new clients at Squared Away. It's been built into that. So, a lot of Shane and my collaboration has been built into Squared Away in that regard. It's been really cool to watch.
Eric Jorgenson: Is that public anywhere, or is that that's just for clients?
Michelle Penczak: It is shared with our clients, yeah.
Eric Jorgenson: All right, keep your secrets, keep your secrets. So looking back at- I mean, from you literally being the first big company perk to now 300 assistants all over the world, which was the hardest chapter of company growth, maybe the biggest step?
Michelle Penczak: The learning that I didn't have to do everything myself, teaching myself what I taught other people to do all the time. That was the hardest piece I think.
Eric Jorgenson: Changing all your instincts.
Michelle Penczak: It was very much, and this was something that Shane and I chatted about a lot, it was changing my narrative and changing my mindset because I was going from the doer to being the CEO and knowing how to teach as opposed to do. And that was a really hard shift internally. But I'm such a doer anyway, I'm very type A, got to do it myself. I guess that’s what made me a really good EA. But now teaching others to do that now and having those same instincts has been really, really rewarding, especially to watch our own assistants grow into their roles.
Eric Jorgenson: Yeah, it’s so hard to teach something you haven't done. So, to have to like force yourself to go through that metamorphosis in order to bring others along and teach them to do the same thing, on the client side probably especially, but internally, I'm sure, creating more leaders and more assistants. How has the job of CEO changed as you've grown? I mean, you went from a small company to quite a big one now, and I imagine your day-to-day is quite different.
Michelle Penczak: It is. I've given a lot in my role previously away, which I'm told or I have learned is what you're supposed to do.
Eric Jorgenson: It doesn’t make it easy though.
Michelle Penczak: It does not make it easy whatsoever. Client calls, I'm not doing a lot of sales calls, that kind of thing. A lot of what I had been doing all along has been given away to other Squared Away leaders who are growing beautifully in their roles. It's hard to watch my babies grow and leave the nest, so to speak, but it's also extremely rewarding to see them doing so well. I don't know. It's hard to formulate that into words because something that I've worked on for essentially 20 hours a day for almost five years is doing really, really well internally. And it's like what am I supposed to be doing right now? Like I haven't taken a lunch break in four and a half years. What do I do now?
Eric Jorgenson: Yeah. Like letting the- I’ll struggle for the analogy, but letting a kid grow up and realizing that you don't have to hold it every single minute of every day when it can walk and go to school and drive itself.
Michelle Penczak: Exactly, exactly. That is it. It's like empty nester without being an empty nester.
Eric Jorgenson: And I mean, four and a half years is really fast for the company to grow that big and to change so much of your role and your instincts and your identity. Like that is a hard way to have to do that so quickly. It's not even like you have time to adjust in between. Your role changes massively every year probably.
Michelle Penczak: Oh 100%. We definitely have. I can honestly say that all of the changes that we've made have been nothing but for the good of our assistants and for our clients. So, we are extremely proud of everything.
Eric Jorgenson: Can you put Squared Away maybe in the context of some of the other offerings that are out there. I don't know how much you know about similar companies in the space or similar offerings, but how do you see yourself sort of fitting into all the other options all the way from hiring a full-time like high dollar EA down to like working with somebody through one of the marketplaces like Upwork or something like that.
Michelle Penczak: Somebody asked me that, something similar. And I honestly don't know that we fit in the mold of any of them. We are a virtual assistant service, but we are also not independent contractors. All of our assistants are W2 employees, and we do offer professional development. We offer mental health days for our team every year, 401k, the whole nine. We pay more than any other EA service that's remotely in the world. We have such a great pool of resources internally for military spouses. And even outside of Squared Away, we have an amazing pool of resources for military spouses. I honestly don't know what arena we fall in right now, but I would say somewhere in the middle of being a full-time internal hire and maybe above like Boldly Belay.
Eric Jorgenson: Yeah, your packages go or offerings go all the way from 5 hours a month up to 75. So, it's not quite a hey, this is a substitute for hiring someone full-time, but you also pair them for the long run. So it's way different than like relying on Fiverr or something, which you can't really do some of these like high trust email and scheduling tasks without really that context and training.
Michelle Penczak: And I think an important piece, too, is like having an independent contractor versus an actual employee. You don't really have that, I don't want to say control, but that understanding and that trust piece of the contractor versus employee.
Eric Jorgenson: Yeah, it is an extra piece of accountability.
Michelle Penczak: And security.
Eric Jorgenson: So, something that I- when we went back, going back to like the most common things and the high leverage stuff that you see delegated, the scheduling, the research, the travel, the planning, those are kind of like basically typical common kind of EA jobs, and I feel like a lot of people maybe underestimate how much time goes into those. They're not super hard, but they are personal preference driven, and they get nervous about outsourcing them, but at the same time, massively underestimate the amount of time they spend on it. And I wonder maybe about some of the stories or experiences you get with people who have taken this step for the first time. And is there a tipping point that you see after a client has been like I don't know if it's one month in or six months in where they're kind of like I had no idea how much this would change my life, or if they're really kind of like, oh no, they take care of my scheduling and books and travel and like that's cool, but it's not- cool, but not like life-changing.
Michelle Penczak: We hear from our clients pretty regularly after two weeks or a month saying, oh my gosh, my assistant has been amazing. I had no idea how much I needed support. She's already done X, Y, and Z, and thought about blank. So, I regularly get almost that templated response from every client. It's pretty awesome. But one thing that I will challenge people to do is those tasks that a lot of people say, oh, it'll take 30 minutes to look into researching X, Y, and Z kind of deal, I would challenge people to look at it yourself, like track your own time doing a similar task or doing that task yourself on your phone or on your computer or whatever, just track it yourself, and see how long it takes you to do it.
Eric Jorgenson: Just start your stopwatch or whatever.
Michelle Penczak: Do a stopwatch, do a timer, and then just track it and then say what could I have done for X, Y, and Z amount of time if I'd have given that away. And another thing, too, is like with inbox management. Track yourself one day checking your email. Every single time you check your email, track how much time you spend checking your email one day and add it all up and say, holy cow, I spent four hours in my email today. I could have given this to an assistant and saved myself four hours.
Eric Jorgenson: Is there a tool for tracking that?
Michelle Penczak: Yeah, we use Harvest internally, and they have a free platform that you can download if you ever get curious or ever want to consider where all of your time is going.
Eric Jorgenson: Oh God, I don't know if I want to- I do want to know, but I'm afraid of the knowledge.
Michelle Penczak: I challenged my husband to do it while he was deployed. He just got home about six- about a month ago and he was like, “Oh, my Lord, I checked my email for nine hours one week.” Like you know where to go for that, right? It's really interesting when people say, oh, well, it doesn't take me that long. Well track your own time and see where your time is going and then where you can delegate.
Eric Jorgenson: It's one of those things that like if you had to guess whether you're underestimating or overestimating it, like no one is underestimating it- or no one's overestimating it. Everyone is spending more time on this stuff then they think they are and would benefit more from help than they think. That has been my experience for sure. So one other comparison, I mean, I feel like one option people have when searching for an EA is whether they go domestic or abroad for lack of a better term. Like, do they use someone who is maybe culturally or natively American, wherever they are in the world, versus somebody who's in maybe the Philippines or India. Do you see a lot of people kind of struggling with that decision and how do you decide what's the correct decision for them?
Michelle Penczak: Yeah, I am definitely seeing people kind of look at those options. It's definitely cheaper, not even going to lie, to find someone abroad. The really cool thing about working with Squared Away is being a team of military spouses. Let me just tell you about military spouses. We are resourceful beyond resourceful. Internally, we have, like I said, almost 300 assistants. We very much operate in a beehive mentality internally. So, if somebody doesn't have an answer after Google, X, Y, Z, they're coming internally saying, oh my gosh, Eric just asked me to find this green rhinestone shirt. I cannot find it. Can somebody point me in the right direction? If nobody has an answer, we have military spouse groups in pretty much every state on Facebook, Instagram, you name it. We're going to our groups, I can pretty much guarantee it, and saying, hey, can somebody find me this shirt? I guarantee you there's a spouse somewhere in this world that will be able to find this green rhinestone shirt. So that sisterhood, brotherhood of being a military spouse, that helpfulness, that tenacity and grit is by far unmatched in our community. And it's really cool to see. To this day, I still do that myself.
Eric Jorgenson: Yeah, it's very cool. And it's nice to know that like the assistants have their own sort of social group and support system and network and it's not like you're just getting the help of one person but this whole sort of network of people who are all supporting each other, which is another perk for certainly the clients but also the assistants I think of working with Squared Away and the benefits of the whole team.
Michelle Penczak: Oh 100%. That's one of the things that we talk about internally all the time. One person doesn't always have the answer. The assistant doesn't always have to have the answer. But we will find it together. And it's absolutely okay to say I don't know, but I promise you, we will find you an answer together.
Eric Jorgenson: I love it. One more quote maybe as we wrap up from another one of your amazing blog posts that I thought was helpful like good thinking and good to share the onus between the assistant and the client is “Successful delegators act as quarterbacks, throwing a task to the delegatee with a touchdown in mind. When a lousy pass is thrown, it ends up causing strife for the entire team.” Did you write that, master of analogies?
Michelle Penczak: I did now actually. I think credit for that one goes to Kelsey. She is also mistress of analogies, so shout out to her.
Eric Jorgenson: I thought that was excellent. And back to where we started with like delegation is a skill and being a great assistant is a skill, but so is being a great client and continuously learning to over-communicate and delegate good tasks and delegate as much as you can, trust and lean on your team to support you. I think all of that is a very, very helpful component and helpful for those of us thinking about working with an EA for the first time or expanding or hiring. I actually imagine a lot of- how often do you notice that working with Squared Away is the first time that a client has managed someone directly or hired someone full or part-time to help grow their business?
Michelle Penczak: I would say about 25% of the time clients have never worked with an assistant before, so it's a new relationship for them, and we're kind of teaching them the ropes along the way.
Eric Jorgenson: Do you like doing that?
Michelle Penczak: I do actually. It's really fun because I love clients who come in and say this is how I like to work. We can absolutely work with that. But it's really cool being able to teach someone to be less stressed and how they can de-stress themselves and their entire lives very simply just by communicating with their assistant and saying, hey for 15 minutes every week. And it's really cool to kind of watch that blossom.
Eric Jorgenson: I love that. Where would you send people to learn more about Squared Away and about you and to take a next step if they feel like they're ready for that?
Michelle Penczak: If people are ready to get started with us, they should email info@gosquaredaway.com, and we will get them Squared Away, all the puns intended. If they want to learn more, they can check out gosquaredaway.com.
Eric Jorgenson: And you have great posts on your personal medium about delegation. Even if you work with someone totally different, or you're just thinking about doing it for the first time, the Squared Away publication and blog are great. Anything else you want people to know? Any final words you'd share?
Michelle Penczak: Even if you're curious about Squared Away, you don't have to get started, please feel free to reach out. We're happy to answer any questions anytime.
Eric Jorgenson: Low commitment, right? It's not like you got to sign up forever.
Michelle Penczak: Oh no, absolutely not.
Eric Jorgenson: Okay. Give it a try. Thank you so much for teaching us everything that there is to know about delegation and how we can be less stressed, and we can help solve military spouse un- and underemployment. It's been a pleasure to talk with you and I'm so excited to see what Squared Away has done and appreciate you taking the time to teach us all.
Michelle Penczak: Well, thank you so much for allowing me to join you and chat, and I hope to join you again sometime in the future.
Eric Jorgenson: I appreciate you hanging out with us today. Thank you so much for listening. If you want to learn more about Squared Away, I encourage you to do so. If you want to learn more about the co-founder Shane Mac, I've got an episode with him previously on the podcast. We talk a lot about crypto in there, but you also get a sense for how Shane gets so much done by listening to the leverage that he gets from his EAs from Squared Away. And I encourage you to check out the supporters of the show, thefounderspodcast.com. You can also support the show by investing with me and my partners through Rolling Fun. Links to both are in the show notes. And if you'd like a free way to support the show, you can leave a very quick review or text episode to a friend or coworker you think would enjoy it. Thank you so much for spending some time with us today. I hope you learned something and will apply it to your life. That's the greatest compliment we could receive. Thank you. Have a great one.