Shows
Beyond OrdersTaylor Lingerfelt: Leading with Heart as a Military Spouse and Team LeadTaylor Lingerfelt is a proud active duty Army spouse, mom of two, and Team Lead at Squared Away. She began her journey with the company in 2021 while at home with her kids, seeking a way to reconnect with her own identity. Over the years, she’s held multiple internal roles, growing her skills in leadership, client success, and remote team management. Today, Taylor is passionate about finding balance between family life and career, leading with empathy, and embracing the beautiful chaos of military life. Her story is a testament to the resilience, adaptability, and leadership that military spouses bring to...2025-08-0937 min
Beyond OrdersBeyond the Bar: Libby Jamison’s Fight for Military Families and Policy ReformThis week on Beyond Orders, we sit down with Libby Jamison, a powerhouse attorney, policy strategist, and unapologetic advocate for military families. With nearly 20 years in law, government, and grassroots organizing, Libby has worked everywhere from the Department of Veterans Affairs to the West Wing, where she served as Senior Advisor to Joining Forces, Dr. Jill Biden’s initiative supporting military families, caregivers, and survivors.
As former President of the Military Spouse JD Network, Libby helped drive licensing reforms across more than 40 jurisdictions, opening professional doors for spouses nationwide. She has earned national recognition, including Military.com's Sp...2025-08-0448 min
An Army of Normal FolksMichelle Penczak: Binders Full of Military Spouses (Pt 1)Military spouse unemployment is 21%, which is 5 times the national average, often because employers don't want to hire people like Michelle Penczak who move every 3-4 years. So Michelle started a virtual assistant company called Squared Away where location wouldn't be an issue. And it's skyrocketed to employing 400 military spouses who serve 1,000 clients! Support the show: https://www.normalfolks.us/premiumSee omnystudio.com/listener for privacy information.2025-07-2943 min
An Army of Normal FolksMichelle Penczak: Binders Full of Military Spouses (Pt 2)Military spouse unemployment is 21%, which is 5 times the national average, often because employers don't want to hire people like Michelle Penczak who move every 3-4 years. So Michelle started a virtual assistant company called Squared Away where location wouldn't be an issue. And it's skyrocketed to employing 400 military spouses who serve 1,000 clients! Support the show: https://www.normalfolks.us/premiumSee omnystudio.com/listener for privacy information.2025-07-2936 min
Beyond OrdersMeagan Eskew’s Inspiring Story – Single Mom, Breast Cancer Survivor, LeaderMeagan Eskew started as a virtual assistant with Squared Away in 2020 and worked her way up to become our Director of Client Connections. A single mom who battled, and beat, breast cancer, Meagan didn’t just climb the ladder, she built her own. Now, she’s stepping into a full-time role with a client buyout, proving what happens when grit meets opportunity.
She homeschools her kids, leads with heart, and shows exactly what betting on yourself looks like when life throws everything at you.
If you’ve ever wondered whether it’s possible to go from sur...2025-07-2744 min
Beyond OrdersMilitary Spouses Make Great Leaders & Jessica Ryan Proves ItWhat does it take to grow from a virtual assistant to a trusted executive leader, all while proving that military spouses are some of the strongest leaders in the workforce?
In this episode of Beyond Orders, Michelle Penczak, CEO of Squared Away, interviews Jessica Ryan, the company’s Chief People Officer. Jessica started in 2020 as a virtual assistant and steadily rose through the ranks, from Team Lead to the executive team, by leading with empathy, consistency, and quiet strength.
Jessica shares how she built trust, supported hundreds of military spouse virtual assistants, and helped shape Sq...2025-07-2146 min
Beyond OrdersFrom Virtual Assistant to COO: Sara Brooks-Glover on Leadership, Growth & ReinventionIn this episode of Beyond Orders, host Michelle Penczak, CEO of Squared Away and military spouse, sits down with Sara Brooks-Glover, Chief Operations Officer at Squared Away, to talk about career growth, remote leadership, and scaling systems in a mission-driven company.
Sara shares her inspiring journey from starting as a virtual assistant to rising through the ranks as Director of Finance and Compliance, leading Talent and Development, and now serving as COO. She offers insights into how she built scalable operations, aligned cross-functional teams, and leaned into reinvention every step of the way.
Whether you're...2025-07-1448 min
Beyond OrdersFrom Grief to Grace: Tiffany McCawley’s StoryIn this deeply moving episode of Beyond Orders, host Michelle Penczak sits down with Tiffany McCawley, a military spouse and mother of five whose faith and resilience leave a lasting impression. Tiffany became part of the Squared Away team in 2020, but her journey began long before that.
In 2015, Tiffany endured every parent’s worst nightmare; the loss of two of her children in a tragic accident. What followed was not a neatly wrapped healing journey but a raw, honest walk through grief, anchored by her faith and a quiet strength developed through lived experience.
Tiffany sh...2025-07-061h 01
Beyond OrdersBeyond the Resume: Leadership, Life Lessons, and Starting OverIn this episode of Beyond Orders, host Michelle Penczak speaks with Rachel Hornbeck, the Director of Talent and Development at Squared Away, about her journey from being a stay-at-home mom to a leadership role within the company. They discuss the supportive culture at Squared Away, the challenges of imposter syndrome, the importance of community, and the personal stories of adoption that have shaped their lives. Rachel shares her insights on leadership, accountability, and the hiring process, culminating in a reflection on the theme of reinvention and personal growth.
Real leadership starts when we stop waiting for permission to...2025-06-2945 min
Beyond OrdersRooted at Last: How Squared Away Became Jordan’s Steady GroundIn the inaugural episode of Beyond Orders, host Michelle Penczak sits down with Jordan Streetman Cole, Chief Experience Officer at Squared Away, for a powerful conversation about the realities of military spouse life and the unexpected opportunities that can come from uncertainty.
Together, they unpack Jordan’s journey from applying to Squared Away out of sheer desperation to growing into a key leadership role within the company. Along the way, they explore themes of reinvention, resilience, and the deep need for stability in a life shaped by constant change.
This episode dives into the unique st...2025-06-2139 min
American PotentialMilitary Spouse. CEO. Job Creator: How Michelle Penczak Built a Business That Moves With YouIn this inspiring episode of American Potential, host David From sits down with Michelle Penczak, a Marine spouse who turned rejection, resilience, and resourcefulness into a thriving business that now employs over 400 people—most of them military spouses just like her.
Michelle shares how she faced over 20 job rejections simply for being a military spouse before finally landing a virtual assistant role that changed everything. But when the company suddenly shut down, she didn’t give up—she kept her clients, built her own company from the ground up, and began hiring other military spouses who needed remote...2025-06-0533 minAmerican PotentialMilitary Spouse. CEO. Job Creator: How Michelle Penczak Built a Business That Moves With YouIn this inspiring episode of American Potential, host David From sits down with Michelle Penczak, a Marine spouse who turned rejection, resilience, and resourcefulness into a thriving business that now employs over 400 people—most of them military spouses just like her.
Michelle shares how she faced over 20 job rejections simply for being a military spouse before finally landing a virtual assistant role that changed everything. But when the company suddenly shut down, she didn’t give up—she kept her clients, built her own company from the ground up, and began hiring other military spouses who needed remote...2025-06-0533 min
American PotentialMilitary Spouse. CEO. Job Creator: How Michelle Penczak Built a Business That Moves With YouIn this inspiring episode of American Potential, host David From sits down with Michelle Penczak, a Marine spouse who turned rejection, resilience, and resourcefulness into a thriving business that now employs over 400 people—most of them military spouses just like her. Michelle shares how she faced over 20 job rejections simply for being a military spouse before finally landing a virtual assistant role that changed everything. But when the company suddenly shut down, she didn’t give up—she kept her clients, built her own company from the ground up, and began hiring other military spouses who needed remote, flexible work that c...2025-06-0533 min
Security Halt!From Military Spouse to CEO: How Michelle Penczak Built a Business Empowering FamiliesLet us know what you think! Text us!Military spouses are often the unsung heroes of service—balancing life, family, and identity while navigating constant change. But what happens when one turns that challenge into a thriving business?In this empowering episode of Security Halt!, host Deny Caballero sits down with Michelle Penczak, military spouse, entrepreneur, and founder of Squared Away, a virtual assistant company that’s revolutionizing how military spouses find purpose and employment.Michelle shares her inspiring journey—from facing the challenges of frequent moves and identity loss to launching a compan...2025-03-2846 min
Business Brain – The Entrepreneurs’ PodcastDiscounting Our Own ExperiencesThe episode of Business Brain features Dave Hamilton and Shannon Jean discussing productivity, mindset, and business strategies. They open with lighthearted Hitchcock-related jokes and discuss the unpredictable nature of the South by Southwest conference. The main discussion revolves around productivity methods, particularly the concept of a “reverse to-do list” or “to-did list,” where one focuses on what has been accomplished rather than what still needs to be done. Shannon shares his preference for using reminders instead of traditional to-do lists, explaining how he frames tasks as things he wants to do rather than has to do, which keeps him motivate...2025-03-1216 min
World's Greatest Boss198. Executive Assistants: How to Effectively Hire and Onboard Yours to Lighten Your Load with Michelle PenczakNo more headaches with trying to manage your global workforce, compliantly hire and pay employees with Deel https://bit.ly/4dSWQXDIf you’ve ever felt overwhelmed by your to-do list or struggled with effective delegation, you’re not alone, and this conversation is just for you! Today, I have the pleasure of chatting with Michelle Penczak, an expert in hiring assistants with a wealth of knowledge to share. We’ll dive into the vital importance of hiring an assistant and how the right support can truly elevate your productivity and enhance your overall peace of mind. Michel...2024-10-2929 min
Professionally SpeakingEmpowering Administrative Professionals: Candid Insights with Lois WilkinsLet us know how you like our podcast or if you'd like to join us as a guestIn this spicy Episode of Professionally Speaking, Beth welcomes Lois Wilkins, Director Breedlove Entrepreneurship Center at the YWCA Metropolitan Chicago, IL. With over 30- years of experience supporting C-suite leaders across diverse industries, Lois offers invaluable insights into the evolution and significance of the administrative professionals role. Beth and Lois explore the pivotal role of administrative professionals in the modern workplace, in this spicy conversation with a seasoned expert .From traditional administrative tasks to strategic support functions, thi...2024-08-2740 min
Hitting The MarkSquared Away: Michelle Penczak, CEO & FounderMichelle Penczak was my assistant for 3 years. Today she runs a 400-people strong brand employing military spouses that made #297 on the Inc 5000 last year. Squared Away is rooted in a mutual bond between people and philosophies and is doing what I keep advising most everyone to be doing: The brand is highly niche-focused, was born out of a personal necessity, and came with a tribe in-tow.
2024-04-0539 min
Driven To Win290 | How This Military Wife Paved Her Own Way to SuccessIn this episode, Chaz Wolfe engages with Michelle Penczak, a successful entrepreneur and military spouse. They explore her business journey, motivations, and the value of partnership in entrepreneurship. Michelle shares her key performance indicator, business resources, and advice to her younger self. She also discusses balancing work and family, and the role of entrepreneurs in employee development.
On today’s episode of Gathering The Kings, Michelle Penczak, the tenacious CEO and Founder of Squared Away, joins us on the queen’s stage. With an incredible 95% of their workforce comprising military spouses, Michelle has built an empire out of a prob...2023-07-1242 min
WeAreLATech Los Angeles Startups Podcast, hosted by Espree DevoraRemix: Cole Mora, Rachael King, and Michelle Penczak: WeAreLATech Startup SpotlightDon't miss out on the next WeAreLATech podcast episode, get notified by signing up here http://wearelatech.com/podcastWelcome to WeAreLATech's Los Angeles Tech Community Spotlight! “Remix: Cole Mora, Rachael King, and Michelle Penczak”WeAreLATech Podcast is a WeAreTech.fm production.To support our podcast go to http://wearelatech.com/believe To be featured on the podcast go to http://wearelatech.com/feature-your-la-startup/Want to be featured in the WeAreLATech Community? Create your profile here http://wearelatech.com/communityHost,Espree Devorahtt...2023-01-0412 min
#ChitShowEp. 94 Interview with Michelle Penczak with Squared AwayIn this episode, I interview Michelle Penczak from Squared Away. They are empowering military spouses to build meaningful careers, be your trusted assistant, and work from anywhere. Can't wait for you guys to hear this interview! Check out Squared Away! Instagram- @awaysquaredTwitter- @gosquaredaway.com Facebook- Squared Away www.gosquaredaway.comSmells Like HumansLike listening to funny friends discuss curious human behavior.Listen on: Apple Podcasts Spotify2022-12-1428 min
Startup RenegadesBecoming the CEO with Michelle Penczak, Founder of Squared AwayNamed Marine Corps Base Kaneohe Bay Military Spouse of the Year 2019 and MCAS Miramar Military Spouse of the Year 2022, Michelle Penczak is a virtual assistant by trade and a military spouse by love. Her husband Sean is a pilot in the Marine Corps, and through multiple relocations and deployments, Michelle built a vibrant, thriving independent virtual assistant business for herself. This grew into the business that is Squared Away today.In this episode, you will hear:How Michelle turned her thriving freelance business into a scalable startup companyWhy she never planned on being a C...2022-08-3024 min
WeAreLATech Los Angeles Startups Podcast, hosted by Espree DevoraRemix: Michelle Penczak, Kyle Harris, and Cole Mora: WeAreLATech Startup SpotlightDon't miss out on the next WeAreLATech podcast episode, get notified by signing up here http://wearelatech.com/podcastWelcome to WeAreLATech's Los Angeles Tech Community Spotlight! “Remix: Michelle Penczak, Kyle Harris, and Cole Mora” WeAreLATech Podcast is a WeAreTech.fm production.To support our podcast go to http://wearelatech.com/believe To be featured on the podcast go to http://wearelatech.com/feature-your-la-startup/Want to be featured in the WeAreLATech Community? Create your profile here http://wearelatech.com/communityHost,Espree Devorahttps...2022-08-1713 min
The ChangeupMichelle Penczak, CEO of Squared AwayThis week’s guest is CoFounder and CEO of Squared Away, Michelle Penczak.Squared Away is a team of trusted assistants who span across the nation. They help businesses and people scale by offering virtual assistance to get busy executives organized. They also have a really compelling hook: they are all military spouses. We talk about the origination of the concept, her journey from executive assistant to CEO and how she scales the team. 2022-06-1043 min
Smart FriendsCreative EA Delegation, the Corporation of You, and Personal Leverage with Robert Hayes and Chris Ho of AthenaTopics:(4:56) - Chris’ background and work at Athena(6:53) - What does a Chief Client Officer do?(10:20) - Robert’s background and work at Athena(17:00) - Robert recruiting Chris to Athena(20:20) - What distinguishes Robert as an operator(25:02) - Robert’s first year with Athena and how the company has scaled (33:39) - Chris’ decision to join Athena(37:28) - Creating a great experience for both clients and the EAs(46:17) - What people use their EAs for at Athena(50:28) - How Athena focuses o...2022-05-172h 03
Smart FriendsEA Delegating w/ Michelle Penczak: Founder of Squared Away - Military Spouses becoming Top Tier Virtual AssistantsThe sponsor for this week’s episode is Founders Podcast. David Senra, the host of Founders Podcast, is a biography-reading machine. If you don’t have time to spend 40 hours reading the full-length biography of some gilded-age entrepreneur, listening to David’s high-quality recap is the next best thing.The Founders Podcast is a paid podcast that costs $99/year or $299 for lifetime access. Subscribing gives you access to more than 200 episodes including the back catalog with episodes about Anthony Bourdain, Arnold Schwarzenegger, Elon Musk, and many more.Visit founderspodcast.com to subscri...2022-04-1958 min
Beyond 8 FiguresDelegating Tasks To Sustain Success with Michelle Penczak, Squared AwayBusiness owners often find it difficult to delegate tasks because they feel like they have to do everything themselves. Michelle Penczak has a message for you: you don’t! Michelle is the co-founder and CEO of Squared Away, a virtual assistance provider that solely employs military spouses. In this week’s episode of Beyond 8 Figures, she shares what her inspirational journey of building and sustaining a business (alongside long stints of solo parenting while her husband is away on deployment) has looked like!About Michelle Penczak:Michelle’s successful career as a virtual assist...2022-04-0627 min
Life After The MilitaryLife After The Military - Michelle PenczakAre you a military spouse looking for meaningful work? Are you a military spouse who wants to work from the comfort of your own home?Are you a military spouse with great organizational and creative skills? Are you a military spouse who can juggle many balls while building trusted relationships?If you answered yes to any of these questions, you’ll want to listen to/view this week’s episode of #LifeAftertheMilitary podcast with military spouse and entrepreneurial business owner of Michelle Penczak Executive Assistants, Saavy Spouses, and Squared Away: Michelle Penczak. 2022-02-1753 min
Tacos and Tech PodcastGetting Time Back with The Squared Away Workforce with Michelle PenczakListen on Apple, Google, Spotify, and other platforms. Michelle Penczak is CEO of Squared Away, a full-service virtual executive assistant company that hires military spouses to help run operations for its clients. The team of more than 200 assistants gives companies, teams and venture capital firms their time back so they can focus on the things that matter most. Michelle grew up in eastern North Carolina, and left home for college then found work as a personal assistant in Washington, D.C. There, she met her husband, a Marine, and returned to North Carolina for his dep...2021-11-0223 min
Sketchy IdeasSketchy Ideas Episode 34: A Team of Delegators with Michelle Penczak0:39 Intro
Intro/Opening remarks
The topic is: Team of Delegators with Michelle Penczak
1:30 Sponsors
SPEARity (SPEARity.com)
Cream City Marketing (creamcitymarketing.com)
2:35 The origin of SquaredAway
Michelle Penczak is today’s guest
Her background story:
1. Can’t get hired
2. Took a temp job
3. Deployed husband
4. Pregnant
5. Employer goes bankrupt
6. Crazy business partner
7. Growing a human and a company
8. Move base to Hawaii
9. Woke up early (3 am Hawaii time to work with EST clients)
10. Do it again…
Business origin story, “Failure + an idea that’s crazier than mine” -Michael
Sometimes it takes someone with a crazier idea...2021-03-1934 min
Modern WitchThe Nephilim Special Prt 2: EvolutionS9E2 The Nephilim Special Part Two: Evolution The Nephilim are an intricate part of several occult traditions and are credited as the progenitors of the Witch Power but still remain little known figures for many practitioners. We invoke them into our circles, call upon them to bend fate, but do you really know who you are asking to come to your aide? On this episode of the Modern Witch Podcast, I am joined by three of my favorite occultists, Jason Miller, Michelle Bellenger, and Christopher Penczak, for a no-holds-bar discussion on who t...2021-02-051h 13
Lunch Pail Daily#33 —📄 You need a coda docTalking about coda which I feel doesn’t get enough love in the no-code community. In the coming weeks planning on moving some of Lunch Pail’s systems from Notion to Coda. Here’s a really great read on the power of Coda https://coda.io/@michelle-penczak/no-code-just-a-coda-doc-how-squared-away-saves-a-thousand-hours2021-01-2805 minModern WitchThe Nephilim Special Prt1: Inappropriately Touched by an AngelS9E1 The Nephilim Special Part One: Inappropriately Touched by an Angel The Nephilim are an intricate part of several occult traditions and are credited as the progenitors of the Witch Power but still remain little known figures for many practitioners. We invoke them into our circles, call upon them to bend fate, but do you really know who you are asking to come to your aide? On this episode of the Modern Witch Podcast, I am joined by three of my favorite occultists, Jason Miller, Michelle Bellenger, and Christopher Penczak, for a n...2021-01-191h 07
Women in Tech Podcast, hosted by Espree DevoraMichelle Penczak of Squared Away, Military Spouses Personal Assistants: Women In Tech CaliforniaDon't miss out on the next #womenintech podcast episode, get notified by signing up here http://womenintechshow.com. Be featured in the Women in Tech Community by creating your profile here http://womenintechvip.com/“Michelle Penczak of Squared Away, Military Spouses Personal Assistants”#womenintech Show is a WeAreTech.fm production.To support the Women in Tech podcast go to https://www.patreon.com/womenintechTo be featured on the podcast go to http://womenintechshow.com/featureHost, Espree Devorahttps://twitter.com/espreedevorahtt...2021-01-1828 min
WeAreLATech Los Angeles Startups Podcast, hosted by Espree DevoraMichelle Penczak of Squared Away: WeAreLATech Startup SpotlightDon't miss out on the next WeAreLATech podcast episode, get notified by signing up here http://wearelatech.com/podcastWelcome to WeAreLATech's Los Angeles Tech Community Spotlight! “Michelle Penczak of Squared Away”WeAreLATech Podcast is a WeAreTech.fm production.To support our podcast go to http://wearelatech.com/believe To be featured on the podcast go to http://wearelatech.com/feature-your-la-startup/Want to be featured in the WeAreLATech Community? Create your profile here http://wearelatech.com/communityHost,Espree Devorahttps://twitter...2021-01-1829 min
Software SocialBootstrapping a Company to 130 EmployeesMichele Hansen 0:00 Hey, welcome back to Software Social. I'm Michele Hansen.Colleen Schnettler 0:04 And I'm Colleen Schnettler. Michelle PenczakAnd I'm Michelle Penczak, the CEO of Squared Away.Michele Hansen 0:09 We are so excited to have Michele with us our guest, another Michelle. She. So she said she's the founder of Squared Away, which is a company that employs mostly military spouses to be virtual assistants. And they have over 130 remote virtual assistants working for them. So Colleen and I are super pumped to have us joining our virtual table...2020-10-1339 min
Embrace the Pivot with Dr. Cheryl RobinsonEpisode 21: Michelle Penczak shares how she created jobs for military spousesMichelle Penczak was forced into a pivot. Instead of making it a negative experience she turned it into an opportunity to create a company that employees military spouses. Squared Away not only provides job security for military spouses but it also gives them a chance to define their own identity. Squared Away is a virtual assistant company that assists corporations around the world.
Michelle’s story is sure to inspire!2020-09-3025 min
Women's Wealth: The Middle Way®Empowering Military Spouses Through Meaningful Work with Michelle PenczakMichelle Penczak, CEO of Squared Away, knows firsthand the challenges that military spouses face to find employment and help provide for their families. She is the mother of two young boys and the proud wife of an active-duty Marine Corps pilot. Michelle launched her firm in 2017 and now employs over 100 military spouses and veterans. Listen in as she shares what she is doing to empower military spouses to build meaningful careers. Join us every other week on Women's Wealth: The Middle Way®, a radio show aimed at helping women navigate questions about work, money, and family. You can find us on...2020-09-3012 min
Women's Wealth: The Middle Way®Empowering Military Spouses Through Meaningful Work with Michelle PenczakMichelle Penczak, CEO of Squared Away, knows firsthand the challenges that military spouses face to find employment and help provide for their families. She is the mother of two young boys and the proud wife of an active-duty Marine Corps pilot. Michelle launched her firm in 2017 and now employs over 100 military spouses and veterans. Listen in as she shares what she is doing to empower military spouses to build meaningful careers. Join us every other week on Women's Wealth: The Middle Way®, a radio show aimed at helping women navigate questions about work, money, and family. You ca...2020-09-3012 min