By Rick Haney and Kaleem Clarkson
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The podcast currently has 99 episodes available.
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In this episode of the Remotely One podcast, co-hosts Rick Haney and Kaleem Clarkson sit down with Chicago-based entrepreneur Sam Rosen, co-founder of Deskpass, to explore his unconventional path to success and the future of coworking and flexible workspaces. Sam’s journey, full of twists and surprises, exemplifies resilience, innovation, and a sharp instinct for recognizing the shifting needs of the modern workforce.
Sam’s career didn’t follow a traditional route. His unique backstory as a "three-time college dropout" is a label he proudly embraces. Rather than viewing it as a setback, Sam sees it as an essential part of his identity as an entrepreneur. His success story proves that a college degree is not the only path to achievement—what really matters is passion, resilience, and adaptability.
Sam’s first major business venture was One Design Company, a digital design agency he founded from his spare bedroom in 2005. At a time when businesses were just beginning to navigate the digital space, Sam found himself in a unique position—acting as a translator between generations familiar with the internet and those who were not.
In 2008, Sam’s entrepreneurial instincts led him to co-found Chicago’s first coworking space, The Coop. At the time, the coworking movement was still in its infancy, with only about 300 spaces globally. His inspiration for The Coop came during a visit to Brooklyn, where he struggled to find reliable internet while working remotely from his girlfriend’s cramped apartment. After an unsuccessful attempt to work from a local café, Sam discovered coworking through a space called "The Change You Want to See." He was immediately drawn to the community-driven atmosphere and knew he wanted to bring this model back to Chicago.
As Sam’s career evolved, so did his business interests. By 2010, he had developed proprietary software to manage The Coop’s operations, including billing and scheduling. This software became the foundation for his next company, DeskTime, which he eventually sold. However, DeskTime was just a precursor to what would become his most successful venture to date: Deskpass.
Deskpass, the platform Sam currently helms, is designed to meet the growing demand for flexible workspaces. Remote and hybrid teams can use Deskpass to find coworking spaces across the globe, giving them the flexibility to work from various locations. Unlike traditional coworking companies like WeWork, which tie members to specific locations, Deskpass operates as a marketplace, offering a wide variety of workspaces without owning any real estate.
Today, Deskpass plays a pivotal role in the evolving landscape of remote work. The platform not only connects users with coworking spaces but also provides businesses with a way to offer remote and hybrid work options to their employees.
Sam’s story is a testament to the power of innovation, resilience, and the ability to forge one’s own path. His ventures—from One Design Company to Deskpass—highlight his forward-thinking approach to business and his deep understanding of the evolving needs of today’s workforce. As the world of work continues to shift, Sam remains at the forefront of the coworking and flexible workspace revolution, offering solutions that cater to both companies and individuals!
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In this engaging episode of Remotely One, co-hosts Rick Haney and Kaleem Clarkson sit down with the multi-talented Kendall Wallace, Founder and Lead Facilitator at Executive Offsites, to discuss her transformative career, her approach to building strong team connections, and her insights into customer and user experience. With a career spanning leadership roles in customer experience, user experience (UX), and remote team facilitation, Kendall brings a wealth of knowledge to the conversation.
Hailing from Richmond, Virginia, and a proud University of Virginia graduate, Kendall began her professional journey in sales before transitioning into the tech world. Her first significant role came at Park Jockey, a startup where she eventually rose to become the Global Head of Customer Experience. It was in this role that she realized the power of user experience in creating more intuitive and efficient digital platforms. One of the key takeaways from Kendall's journey is her passion for building meaningful team connections, especially in the context of remote work. As the founder of Executive Offsites, Kendall designs and leads in-person retreats aimed at fostering communication, trust, and collaboration among distributed teams.
Her retreats emphasize the importance of blending work-related goals with opportunities for personal connection, helping remote teams build stronger relationships and tackle the challenges of maintaining trust and communication.
A highlight of this conversation is the in-depth look into Kendall’s transition from customer experience to UX, a move driven by her role at Park Jockey. As the head of customer support, she noticed recurring issues that could be solved through better UX design. By identifying patterns in customer inquiries, she saw how user-friendly digital experiences could prevent problems from arising in the first place.
Kendall shares her confidence that remote work is here to stay and reveals why in-person retreats are set to play a pivotal role in shaping the future of distributed teams. She dives into how these offsites can build trust and connection, emphasizing the need for personalized approaches rather than one-size-fits-all solutions. Expect valuable insights on designing meaningful team experiences that truly impact dynamics!
Her passion for fostering meaningful relationships in both personal and professional spaces shines throughout the episode. Kendall’s mix of vulnerability, leadership wisdom, and enthusiasm makes this a must-listen for anyone navigating remote work or looking to strengthen team dynamics. Whether you’re leading a remote team or simply navigating workplace challenges, Kendall’s story offers valuable lessons on growth, self-awareness, and the power of human connection. With her holistic approach to team-building, Kendall provides a roadmap for creating stronger, more resilient teams in an increasingly remote world.
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Join hosts Rick Haney and Kaleem Clarkson for a lively and insightful chat with Iwo Szapar, the CEO and co-founder of Remote How. Together, they dive into a conversation brimming with humor, camaraderie, and deep insights into the ever-evolving future of work. Iwo, a trailblazer in remote work advocacy and an expert in AI integration takes us on a journey from his hometown of Gdynia, Poland, to becoming a global thought leader. With a resume boasting over 3,000 companies—including heavyweights like Walmart, Microsoft, and ING Bank—Szapar has been at the forefront of helping businesses navigate the complexities of remote and hybrid work.
Iwo reflects on his international adventures, which began with a work opportunity in Austin, Texas, and blossomed into a nomadic lifestyle that has seen him living in 15 countries across Asia, Europe, and beyond. His travels, driven by a passion for experiencing diverse cultures and broadening his perspective, have deeply influenced his approach to remote work. From the vibrant streets of Vietnam to the serene landscapes of Colombia, he has witnessed firsthand the global shift toward remote work, a trend that surged during the COVID-19 pandemic.
The spark that ignited Remote How in 2017—a time when remote work was still gaining traction—was fueled by the growing demand among millennials for work flexibility and the challenges companies faced in attracting talent. Remote How was born with a clear mission: to empower individuals and organizations to fully embrace the freedom that remote work offers.
As one of the early adopters of the digital nomad lifestyle, Iwo shares his insights into the unique challenges and rewards of this way of life. He also traces the remarkable evolution of Remote How and its significant impact on the remote work landscape. From its inception with the Remote Future Summit—the largest virtual conference on remote work at the time—to the launch of the Remote How Academy, the world’s first certification program for remote workers, Iwo has been committed to equipping individuals and companies with the skills and knowledge necessary to excel in a distributed work environment.
Now the Remote Work rocket continues to soar and the intersection of AI and remote work becomes increasingly inevitable. For Iwo, AI is set to reshape industries, emphasizing that AI should be seen as a tool for empowerment rather than a threat. But despite being a visionary, Iwo remains grounded in the reality of uncertainties surrounding the future of work, particularly with the rapid advancement of AI. Traditional career paths, like software engineering, which were once considered secure, are now being challenged by the rise of AI.
This must-listen episode is perfect for anyone interested in the evolving landscape of remote work, the challenges of organizational change, and the transformative potential of AI. Szapar’s unique insights and experiences offer valuable guidance for navigating these complex and rapidly changing environments. Whether you’re a remote work enthusiast, a digital nomad, or simply curious about the future of work, this episode is packed with knowledge and inspiration to help you embrace the future with confidence and creativity.
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In this lively episode of the Remotely One podcast, hosts Rick Haney and Kaleem Clarkson chat with Sacha Connor, founder of Virtual Work Insider and a seasoned expert in remote work. Get ready for some valuable insights as Sacha takes us through her professional journey, marked by her pioneering role in remote work long before it became mainstream. Her story, deeply influenced by her Philadelphia roots, is one of resilience, innovation, and a commitment to redefining work in a distributed environment.
Sacha's career took off in brand marketing after she graduated from Lehigh University. She worked at various advertising agencies, including the prestigious Goodby Silverstein & Partners in San Francisco. But her desire to get closer to the products she was marketing led her to The Clorox Company in Oakland, California, where she managed iconic brands like Hidden Valley Ranch, Kingsford Charcoal, and Brita Water Filters!
A pivotal moment came when Sacha decided to relocate to Philadelphia after the birth of her first child. Not wanting to leave her role at Clorox, she boldly asked to work remotely from the opposite coast—a groundbreaking idea in 2010, long before remote work was widely accepted. Clorox agreed but with significant caveats. However, despite these limitations, Sacha embraced the challenge and became one of the early pioneers of remote work, navigating the steep learning curve during a time when the tools and technologies we now take for granted were still in their infancy.
As Sacha's remote work experiment at Clorox evolved, she effectively led distributed hybrid teams. Initially, the company viewed her remote work arrangement as a temporary experiment with strict boundaries. Still, Sacha's success eventually paved the way for a broader acceptance of remote work within the company.
Turning 40 became another turning point in Sacha's life. Contemplating the next stage of her career, she decided to establish Virtual Work Insider. Virtual Work Insider offers training programs aimed at developing virtual leadership skills and equipping leaders with the tools they need to manage hybrid, remote, or geographically distributed teams.
They also assist organizations in developing "team working agreements" or "team charters," which are foundational documents that clearly define how teams will operate in a distributed work environment. These agreements cover aspects like meeting times, communication norms, and how to accommodate team members in different time zones, helping to overcome some of the challenges that come with flexible work arrangements.
Sacha’s experiences and insights provide a valuable perspective on the ongoing evolution of work in a post-pandemic world. As companies continue to navigate the complexities of hybrid work, clear communication, effective coordination, and strong leadership skills are becoming more critical than ever. Through Virtual Work Insider, Sacha is helping shape the future of work by providing the tools and training necessary for teams to thrive, no matter where they are located!
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In our latest episode, Rick and Kaleem chat with the brilliant Adam Horne, co-founder of Open Org, for a captivating discussion you won’t want to miss. Dive into Adam's remarkable journey, the complexities of today's workplace culture, and the inspiring mission behind Open Org.
Adam, who also was co-founder and Chief People Officer at Scout, has helped over 60 companies hire around 1,500 people. Named a LinkedIn Top Voice in HR communications, his insights are invaluable, especially given his introverted nature and preference for a quiet life outside of work. This intriguing mix of public professional persona and private nature sets the stage for an in-depth exploration of his professional philosophy.
Adam stirred up a buzz with his recent LinkedIn post likening company culture to processed food, coining the term "ultra-processed culture." He explains how companies often present glossy facades to lure talent, much like processed foods use flashy packaging to entice buyers.
This conversation highlights the importance of genuine transparency in company culture. Adam believes open communication and realistic expectations are key. Companies that share handbooks and maintain detailed knowledge bases tend to retain employees better and foster a healthier work environment!
The trio discusses the impact of remote work on company culture. Adam notes that remote companies must excel in communication and transparency, as they can't rely on physical proximity to manage their teams effectively. When it comes to communicating work culture effectively, Adam stresses the importance of honesty and transparency. He suggests that companies provide a balanced view of their work environment, highlighting both positives and challenges. Drawing on insights from Brian Adams, an expert in employer branding, Adam underscores the value of clear and honest messaging about what it's really like to work at a company. This balanced perspective allows candidates to make informed decisions and ensures a better fit between employer and employee.
Adam's insights reflect a profound understanding of evolving workplace dynamics, emphasizing the crucial role of transparency from employers and the necessity for job seekers to be diligent in their research. His focus on clear communication and resource accessibility aligns perfectly with Open Org's mission to support HR and people-focused professionals worldwide. Adam’s advice serves as a comprehensive guide for both job seekers and employers navigating the complexities of modern work environments. Whether you're looking to understand workplace culture better or improve it, especially in the era of remote work, this conversation is a must-listen!
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Welcome again to Remotely One’s Not Safe For Remote Work, where employees at all levels share their most outrageous moments while working remotely!
In this episode, we chat with Kristin Bass, CEO of AbstractOps, a company that eliminates the stress, uncertainty, and financial risk of state compliance. From Kernersville, North Carolina, now living in Auburn, Alabama, Kristin shares her wild journey from fintech to startups and her rapid rise to CEO. Hear about her adventures managing payroll tax compliance and scaling back-office operations.
Tune in for hilarious stories involving her loyal Labs, Duke and Dixie, a shotgun scare that'll leave you laughing out loud, and a memorable sales call interrupted by some unexpected behavior. Don’t miss this fun and unforgettable episode with the charming and resilient Kristin Bass!
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Join us for an engaging new episode of Remotely One, where hosts Rick Haney and Kaleem Clarkson welcome Ben Kvalo, a seasoned professional in the gaming and entertainment industries, and the Founder of Midwest Games! His impressive journey from Portage, Wisconsin, to his current residence split between Los Angeles and Green Bay is not only outstanding but also fascinating. Ben's career trajectory is remarkable, with roots in sports management influenced by his family's football legacy. His entrepreneurial spirit emerged early, starting a radio station in college, which led to a brief stint in professional radio before making a significant transition to the gaming industry.
Ben chats about his pivotal career move to 2K, where he contributed to the success of major franchises like Borderlands, BioShock, Civilization, Xcom, Mafia, and NBA2K. His role at 2K provided him with comprehensive insights into the gaming business, igniting his passion for supporting creatives with his operational expertise. Ben shares his initial culture shock when moving from Wisconsin to San Francisco, contrasting the lifestyle differences and the booming tech innovation of the 2010s.
Interestingly, Ben transitioned from games to the film industry with Netflix, before circling back to the gaming world. The differences between the gaming and film industries are significant, with Netflix's revolutionary approach to technology and streaming standing out. Ben discusses the global accessibility of Netflix, which democratized content consumption and catered to diverse viewing habits.
What took Ben to the next stage of his career? His decision to start his own company, Midwest Games, stemmed from his passion for remote work. This ignites a desire among individuals seeking flexibility and a better work-life balance. Midwest Games embraces remote work, fostering a culture that supports underrepresented developers and prioritizes innovation and creativity, letting people control their own destinies.
Not only are Ben’s ideas technologically revolutionary, but they are also groundbreaking in another way: his decision to focus on underserved populations in his hiring practices. Ben explains that the traditional concentration of the video game industry in expensive cities like LA, San Francisco, Seattle, and Austin excludes many talented individuals from other regions. A study shows that two-thirds of the U.S. video game industry is concentrated in these areas, despite the high cost of living and the lack of necessity for physical presence in the digital age.
His journey from Netflix to founding Midwest Games underscores the transformative potential of remote work and the importance of creating flexible, inclusive work environments. By challenging the traditional geographic concentration of the video game industry, Ben is not only building a successful company but also contributing to a more equitable and diverse industry landscape. Join us for this insightful and inspiring episode to hear more about Ben's remarkable journey and his vision for the future of remote work in the gaming industry. Thank you for the amazing chat, Ben!
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Get ready for a fun-filled and insightful NSFRW episode! Hosts Rick Haney and Kaleem Clarkson chat with Beckie Jones, the CCO of Reef. This time, Beckie recounts her most outrageous remote work experience that involves a high-stakes client meeting and an unexpected event! Listen in as Beckie shares how she kept her cool amidst the chaos, proving that anything can happen when you're working remotely.
But it's not all mishaps and mayhem—Beckie also dives into her role at Reef, the multi-award-winning app that's revolutionizing remote and hybrid work by connecting teams with laptop-friendly venues across the globe. Discover how Beckie's innovative work helps enhance remote working lives and why good Wi-Fi and a kid-free zone are now at the top of her meeting requirements!
Packed with laughter, surprises, and valuable insights into the world of remote work, this episode is a must-listen. Beckie's resilience and adaptability will inspire you, and her story will remind you that even the most unexpected situations can have a sweet ending. So, grab your headphones and join us for a delightful episode filled with cake, chaos, and career highlights!
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What a lively and insightful episode! Hosts Rick Haney and Kaleem Clarkson chat with Tegan Bukowski, the innovative co-founder and CEO of WellSet.
Tegan's unique upbringing set the stage for her extraordinary journey, beginning with her formative years living on a 34-foot powerboat in Puget Sound, Washington. This unconventional lifestyle, which Tegan humorously refers to as her first remote working job, fostered her independence and adaptability.
Her transition from life on the boat to a successful career in Los Angeles is marked by impressive academic and professional achievements. Her dedication to social impact became evident through her nonprofit work, leading projects worldwide, such as designing a photovoltaic field in Rwanda and conducting art therapy with children affected by conflict. This work has received recognition in prestigious publications like The New York Times, Time Magazine, and Vogue.
Our guest transitioned from architecture at Zaha Hadid, where health challenges led her to explore holistic health, creating WellSet, the first holistic health platform for teams to combat burnout. Her decade-long journey saw wellness evolve from niche to necessity, driven by her personal health struggles. Becoming a yoga instructor, she used yoga, meditation, and diet to manage her condition, teaching globally.
Key achievements include wellness activations for companies like Samsung and Lululemon, often through organic opportunities from her rooftop sessions. Co-founding WellSet with Sky Meltzer in 2018, they pivoted from in-person sessions to digital offerings during the pandemic, with the Stay at Home Wellness Festival attracting 45,000 participants. This success transformed WellSet into a digital studio with diverse daily classes.
Tegan's journey through wellness, entrepreneurship, and remote work encapsulates the evolving landscape of holistic health and the profound impact of the pandemic on work and wellbeing! Her story is a testament to resilience, adaptability, and the enduring importance of community and holistic care in navigating modern challenges. Thank you for joining us this time, Tegan!
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In our latest episode of Not Safe for Remote Work, Rick and Kaleem had the pleasure of chatting with Jamie Jackson, who wears multiple hats as the Chief Meme Officer at Humorous Misery, LLC, and co-host of the popular HR Besties podcast. Jamie brought her trademark humor and wit, sharing delightful anecdotes from her experience working remotely.
Jamie quickly touched on her role as a "personality hire" within her workplace, where she infuses humor and light-heartedness into the corporate culture. Beyond her work anecdotes, Jamie has a thriving online presence! She manages several favorite meme pages, including @humorous_resources, @millennial_misery, and @parody_parenting, each showcasing her talent for blending humor with relatable content.
Tune into HR Besties for more laughs and insightful discussions on HR topics.
Thank you, Jamie, for the infectious energy and engaging storytelling! This episode is a delightful peek into the lighter side of remote work, illustrating how unexpected and humorous moments can foster camaraderie and strengthen workplace relationships.
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