“To create a fantastic work culture, establish a fun culture where laughter, games, and banter is incorporated into everyday interactions” with Ryan Roff of boldSOCKS

Jason Malki
Authority Magazine
Published in
17 min readDec 3, 2019

Establish a fun work culture where laughter, games, and banter is incorporated into everyday interactions. For example, every year, sales significantly increase during the holidays leading to longer hours and additional responsibilities for all of our employees. The Wednesday before Black Friday, to help keep morale high throughout the season, we kick off the Holiday Games (a mix of Fantasy Football, Chutes and Ladders, Camel Up, and just about every other board game you can think of). Every employee drafts 4 socks that they think will sell best during the holidays and then I tabulate the scores daily and move everyone forward on a whiteboard track. We also play a game each day, sock themed of course, that provides bonus opportunities to move on the board. To keep things fun, we also play games like four square, office basketball, Mario Kart, life-size foosball, cornhole, darts and more.

As a part of my series about about how leaders can create a “fantastic work culture”, I had the pleasure of interviewing Ryan Roff. Ryan is a social entrepreneur with a passion for using business to create measurable change and social justice. He is an owner of boldSOCKS and the co-founder of Statement Sockwear (a sock brand with a social enterprise model). Ryan represents the creative and marketing side of boldSOCKS. He currently oversees the strategic and creative development of the brands under the boldENDEAVORS umbrella (boldSOCKS.com, boldSOCKS, boldSOCKS Retail and Statement Sockwear) and casts the long-term vision as the CEO of the company.

Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

boldSOCKS started as a competition between friends to see who could wear the boldest socks. The water cooler sock discussions turned into brainstorm sessions for how to start a retail site that could bring all the best socks and brands together online and a site was born: boldSOCKS.com. My business partner, Ryan Preisner, stayed at his corporate job until the second year of business when sales exploded. He could no longer keep up with the pace of two full-time jobs so he made the jump to entrepreneurship. Following my experience at the same corporate company where Ryan and I met, I went on to a marketing agency to broaden my horizon and advance my skills. It quickly became apparent that for boldSOCKS to grow, I too would need to jump in full-time and lead our creative and marketing. As time went on, we hired 6 employees and I eventually took over as CEO to help manage the team and cast the vision for the company. I currently serve in this capacity today.

Can you share the most interesting story that happened to you since you began leading your company?

Since starting our business in 2011, we’ve been a growing, “up-and-to-the-right” company. Years and years of growth put us at the top of the market and the top of our game until this past year when we experienced a sudden drop in organic traffic, and thus a drop in revenue. It was sudden, and it was dramatic. We scrambled to identify the root cause, worked to improve our site, and hoped to turn it around immediately. That didn’t happen.

My pride and ego were crushed. For the first time in my career, I couldn’t fix it or solve it. Every potential solution left me drained seeing little to no progress and anxiety slipped into my everyday consciousness. As a social enterprise company, the idea that our donations to 20 Liters (a clean water organization we support) could dry up or people could be laid off haunted me and kept me awake at night.

I share this story because through every hardship, companies, and more specifically those casting a vision for companies, experience transformation. As my back was against the wall, I was able to see with new clarity exactly what needed to change in our company and perhaps more importantly, how important our team was to our future growth and success.

Without a second thought, Ryan and I decided to forego our paychecks to protect the health of the company and keep the momentum we’ve spent years creating, moving forward. We are undoubtedly in the best place we’ve ever been as a company. We may not have the same revenue we once had, but our team is collectively moving toward common goals and is committed together to a clear mission. We see a much broader view of our business and our potential.

Are you working on any exciting projects now? How do you think that will help people?

We are currently working on expanding our custom sock offering with new, innovative solutions. Anytime we bring in a new solution, the entire team is necessary to pull it off. This past year, we introduced a new lineup of products that allows customers to fully customize a pair of socks with a name, message, design or even a face. The new line creates an opportunity for our team to think like entrepreneurs and gives them ownership of the results.

We see e-commerce changing as companies try to differentiate themselves and offer one-of-a-kind products and services. The market is flooded with low-priced goods and big box stores offering similar national brands so to stand out it is imperative to find a niche offering.

At boldSOCKS, we do this by manufacturing and retailing our own brands, Statement Sockwear and boldSOCKS, and allowing customers to further customize or personalize those products. We take our work a step further than most retailers by adding in a service like printing on socks and labels or packaging sock gift boxes and groomsmen kits in order to provide a boutique-like experience. This personal touch combined with our unique story as a social enterprise that utilizes ethical manufacturing gives us a unique value proposition.

Ok, lets jump to the main part of our interview. According to this study cited in Forbes, more than half of the US workforce is unhappy. Why do you think that number is so high?

The marketplace is changing and with it, the workforce. Traditional values that guided a generation towards loyalty and security no longer create the same value proposition for the next generation. We spend a significant portion of our time at work and thus, a significant portion of our energy. A separate, siloed approach to work and life creates constant, opposing tension. Finding the appropriate balance often comes at the expense of the other making it necessary to lookout for the best interests of one’s self, not the organization.

Compounding on that tension, as stated in the study highlighted by Forbes, is distrust in management and feeling as though the blood, sweat, and tears poured into the job doesn’t translate into tangible results or recognition for the work completed.

Essentially, employees are faced with a concoction of compartmentalized work stress, a lack of time and energy at home, a distrust in or resentment towards management, a disconnect between work output and value, and lack of communication or affirmation from superiors. It is no wonder the workforce is unhappy. It is a disastrous recipe.

We believe it is our responsibility to foster a work environment where work and life can work in harmony with one another, not opposition. We believe we need to find the intersection points and overlapping areas that create the greatest meaning and growth for employees.

At boldSOCKS, this looks like ongoing affirmation and feedback, connecting employees to the outputs and value of their work, communicating often about relational, environmental, and financial energy, and establishing an open and clear line of communication with everyone, including management.

Based on your experience or research, how do you think an unhappy workforce will impact a) company productivity b) company profitability c) and employee health and wellbeing?

An unhappy employee, or worse yet, an unhappy workforce, has a cascading effect on the rest of the organization. In an environment where positivity is the norm, an unhappy person, openly or quietly, affects everyone. It is like water seeping into the cracks of a road; eventually it will freeze and then fracture the asphalt beneath, creating potholes. Although the potholes can be fixed temporarily, the damage now affects the entire road as water finds new pathways and drivers compensate, worsening the entire road.

We are all interconnected and our happiness, and more importantly, our fulfillment, are obvious to those around us. If an organization fails to create a happy workforce, retention plummets, costs increase, and the overall success and profitability of the organization declines.

Unhappy employees often lack the necessary drive, especially in a small business, to follow through and complete projects, stimulate creative ideas, stay engaged at work, and communicate well with team-members. Complacency and disinterest guide everyday interactions and goals making it very difficult to be productive and create momentum.

Unhappy employees are especially detrimental to sales and customer service where interactions with customers make-or-break a company like boldSOCKS. One quick scan of our reviews and you can see how important positive interactions are to retaining customers and loyalty. According to a study in The Happiness Advantage, happiness created a 37% increase in sales and increased accuracy by 19%. To keep our customers happy, we have to first keep our employees happy or our profits will decline.

Productivity and profitability are closely linked during an employees tenure, but turnover is especially detrimental and often a hidden cost for most businesses. The constant change of employees affects morale, burdens employees with additional responsibilities, and adds recruitment and onboarding costs that add up very quickly.

That’s why, for us, we really see the health and well-being of employees as a core initiative. Sustaining morale and joy at work, while it may cut into immediate productivity to play a game or banter a bit, it actually saves our company in the long run. Unhappy employees affect happy employees, but the reverse is also true. Creating a positive work environment contributes to the overall health of employees and provides an opportunity for us to gain momentum as a company.

Can you share 5 things that managers and executives should be doing to improve their company work culture? Can you give a personal story or example for each?

  1. Establish a common purpose that provides greater meaning for the organization and everyone involved. The purpose should have a clear vision and employees should see the tangible connection between their work and the greater good it creates for society. Our mission, simply put, is to do good with socks. This looks like creating an ethical supply chain (which costs us 3–4 times more), providing clean water in Africa, donating our time to mentor local students, and treating every customer with dignity and respect. Example: The biggest initiative for our team is certainly clean water, but a few years ago it was hard for our team to understand the vision of our social impact. We spent a lot of time training our team and even brought in a filter to learn about the technology and teach customers how it works, but we realized, without going to Africa, it is hard to see the impact. So, we decided to launch some local initiatives that the entire team could support. We brainstormed ideas and decided to mentor students at an underserved school once a week. We all hop in a car together during the workday and spend time with students to get them caught up and establish positive role models in their lives. We’ve been able to see how important this initiative is for both the students and our employees.
  2. Foster a culture that celebrates flexibility and a positive work/life balance. Strict corporate policies and schedules that fail to acknowledge the goals and objectives of each individual create tension and disconnect between leadership and the employees. In a changing work culture, it is imperative to adapt to employees that value wholistic fulfilment most. Example: We do not have a strict start or end time and employees have the opportunity to flex schedules based on ideal work times and needs at home. We want boldSOCKS to work around our employees’ lives, not have their lives work around boldSOCKS. Story: As better explained below in the quote section, my business partner and I take mini-sabbaticals every year to reset our rhythms and cast vision for the future. Taking a step away from the business helps creatively dream about the future and understand the bigger picture in life. Not everyone on our team has the financial means to take extended time away, but we do strive to provide great vacation time benefits to encourage the same personal growth and grounding.
  3. Encourage and affirm the personal growth and development of each employee. Beyond just recognizing an employee’s contributions at work, affirm how they’ve grown as an individual and support and dream with them to help them achieve their goals. Example: Our standard for growth is that employees are better today than the day they started at boldSOCKS. The more I interact with our employees and dream with them, the more I understand my role, as a CEO, is not just to provide vision for the company, but to also help them create vision for their life. We conduct quarterly one-on-ones where we discuss their relational, environmental, financial, spiritual, and health goals.
  4. Listen and communicate transparently to employees and customers. Relationships create trust and provide autonomy while breaking down the harmful and often misleading assumptions between employees and management. Story: This past year, after we saw a significant drop in organic traffic, we knew it was important to provide immediate clarity around how it might affect our employees personally and what our plans were to recover the traffic. We knew that communication was extremely important when operating outside of the norm. In addition to providing a State of the Company and monthly update meetings, I also shared how the drop in traffic affected me personally. I shared a sort of manifesto that detailed my own learnings, failures, and opportunities for growth. Knowing I get to help provide guidance to our employees, admitting my own faults and failures helped us see new levels of transparency and growth.
  5. Establish a fun work culture where laughter, games, and banter is incorporated into everyday interactions. Example: Every year, sales significantly increase during the holidays leading to longer hours and additional responsibilities for all of our employees. The Wednesday before Black Friday, to help keep morale high throughout the season, we kick off the Holiday Games (a mix of Fantasy Football, Chutes and Ladders, Camel Up, and just about every other board game you can think of). Every employee drafts 4 socks that they think will sell best during the holidays and then I tabulate the scores daily and move everyone forward on a whiteboard track. We also play a game each day, sock themed of course, that provides bonus opportunities to move on the board. To keep things fun, we also play games like four square, office basketball, Mario Kart, life-size foosball, cornhole, darts and more.

It’s very nice to suggest ideas, but it seems like we have to “change the culture regarding work culture”. What can we do as a society to make a broader change in the US workforce’s work culture?

The very first thing we need to do in regards to change as a nation is make sure each individual is supplied with the necessities to thrive regardless of their job. Healthcare, retirement plans, extended maternity and paternity leave, increased paid time off, and a higher minimum wage are all things that either most of us wish for or take for granted. A lot of people in our society are struggling to survive and that should be addressed by those of us who are in the position to have the conversation of “how can we make things better.”

The happiest countries in the world all have in common that they enjoy universal health care, low to no tuition cost, subsidized parental leave and quality public services for all. Most of them are also environmentally conscious and moving towards Their basic needs are met, allowing them to pursue fulfillment at a higher level.

Once we address the workforces’ basic physiological and safety needs with a livable, smart and functional system, then we, as employers, can focus on their higher needs that lead towards flourishing. Until basic needs are met, we will continue to see a disconnect in society and the workforce will need to continue to make sacrifices to just scrape by in a job that does no more than pay the bills.

How would you describe your leadership or management style? Can you give us a few examples?

I strive to be a servant leader with a democratic and visionary management style. It is my conviction that to be a good leader, I must identify and meet our employees needs. Although I will not be able to solve everyone’s problems, I hope to prop up others in the organization before myself, equipping them to be their best, even if I, in return, will need to sacrifice a bit. I hope to listen before speaking, ask questions before inserting my opinion, identify conflict and look for reconciliation, seek accountability and trust versus power and authority, and lead by example not by words.

One way to identify and meet our employees’ needs is to find out what challenges they face on a daily basis. A few years ago, we added a number of employees and didn’t have enough parking spots for everyone downtown. With a limited number of spaces, we gave everyone the choice to walk in from a few blocks and receive additional compensation or to keep their current compensation and park in the ramp nextdoor. We realized there was a potential that we, as owners, would not be able to have a parking spot downtown, but we thought it was important that everyone had the opportunity to choose.

We also want to be the first line of defense financially so when revenue dropped a bit, we knew it was important to forgo our paychecks before asking anyone else to make a sacrifice.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

In eighth grade, my youth pastor, Jer Swigart, pulled me aside and asked if I would like to meet for coffee once a week to talk about life and share experiences. Those meetings turned into a lifelong friendship and mentorship that continues to shape who I am today.

Jer is the co-founder of The Global Immersion Project. His radical approach to peacemaking challenges my willingness to approach conflict and mend the divide and brokenness in our society. He’s inspired me to approach business and relationships with a unique perspective that acknowledges our shared experiences and value in this world.

About ten years ago, Jer shared how his daughter was learning what it means to host and serve others. He explained his parenting philosophy and how he hoped to invite her to serve a greater purpose and come along for the journey. The conversation identified a bit of my own inner turmoil and how I wanted to do something greater with my life than just punch a clock. The conversation, and subsequent conversations thereafter, set me on a trajectory to find a way for my commitments (like work) to also incorporate a mission for social change. Many of those same principals guide my life and this business today.

How have you used your success to bring goodness to the world?

Our story, like so many other social enterprises, started after an experience that disrupted our norm.

We participated in a filter build five years ago to create clean water for people in Africa. By the end of the night, we built 450 sand and membrane filters to be distributed to families that lacked basic access to clean water. A few days later, we received an email explaining that we needed to raise $100 per filter to get the water filters from Grand Rapids, MI to a village in Rwanda. The filters, despite being built and ready to be distributed, were likely going to sit in a warehouse until the end of the year when 20 Liters received enough donations from their year-end giving campaign. How could we be so close to providing life changing technology and yet so far?

We wanted to help.

In 2014, we launched Statement Sockwear with the goal of providing 100 days of clean water with every purchase. Over 300 sock designs and 32 million days of clean water later, our goal to create sustainable funding is becoming a reality and socks are making a sustainable difference in the world.

While we continue to dream about and realize the lasting impacts of clean water, we understand it cannot end there. We know we can’t hurt one society while trying to help another.

Globalization continues to change commerce, and more specifically for us, the fashion industry. Fast fashion demands cheap goods fast and often overlooks how these goods are manufactured. Everyone deserves to be treated with dignity and respect, and we know it is crucial to partner with the right supplier that values people over profits.

We found a vertically integrated manufacturer in Colombia that aligns closely with many of the same values we aspire to. We know we are paying three to four times what we’d pay in Asia, but to find a partner that develops high quality, ethically made socks is, in our opinion, worth the investment.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Ruthlessly eliminate hurry in your life.”

Four years ago, I made the leap from working the long hours of two full-time jobs (as I moonlighted my entrepreneurial gig with my secure, agency job) to the vast unknown of entrepreneurship. My days were no longer configured by someone else, and I had the unique opportunity to establish new rhythms and a new lifestyle. I set out to learn about my optimal self and do the soul keeping I so desperately needed as I teetered on burnout for so long.

Before settling into a new norm, I took a one-month mini sabbatical in Denver, CO with the goal of a complete refresh. Every day, for the entire month, started with meditation, reflection, devotion and admiring the sunrise and concluded with the same practices in the evening and the sunset. During the day, I worked during my most productive hours (8am-12pm and 8pm-10pm) and set out to explore the mountains the rest of the day.

During that trip, I read a book called Soul Keeping by John Ortberg that captivated my attention and reshaped my goals and objectives. In the book, John Ortberg asks how to properly care for the soul in a fast-paced life hinged on commitments and hectic rhythms. Dallas responds “You must ruthlessly eliminate hurry in your life.” I couldn’t shake those words as I reflected on my journey and the trip. To eliminate hurry meant I needed to slow down. I needed to take a deep breathe and recognize where I was going and how I was getting there. It caused a hard reset.

The separation from the business paired with the natural beauty inspired vision, creativity, and passion that set the company, and me personally, on a new trajectory.

I now take a “Soul Keeping” trip (mini sabbatical) once a year and build in many of the same practices and rhythms from that first trip into my daily life.

If you’d like to hear more about this journey, you can listen to this Podcast:https://www.buzzsprout.com/191092/781680-7-ryan-roff-bold-intentionality-designing-life-and-the-importance-of-soul-keeping-trips

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Leverage your business for good.

For most entrepreneurs, we recognize the opportunity and success as a gift knowing the challenge to launch a new idea and disrupt a market. We also recognize that at any time, the demand could shift or the market could change. The world, economy, and technology is moving incredibly fast, and we are more connected than ever.

Now is the time to make a contribution to the world. To use companies as a platform for social or environmental change.

Our connection to clean water began because we participated in a filter build several years ago. After building 450 filters, we were eager to learn about when they would be distributed and how they would transform communities lacking basic access to clean water.

Instead, we discovered it would take another round of fundraising (about $100/filter) to get them to Rwanda and until 20 Liters raised the funds, they would likely sit in a warehouse collecting dust.

It troubled us that despite the community’s efforts to build the filters, without sustainable funding, organizations are unable to adequately serve their purpose. We decided to leverage our own business and have now contributed over 31 million days of clean water.

It is our deep conviction that businesses, when oriented towards good rather than just profits, can make a profound impact on our world.

Thank you for these fantastic insights. We wish you continued success!

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Jason Malki
Authority Magazine

Jason Malki is the Founder & CEO of SuperWarm AI + StrtupBoost, a 30K+ member startup ecosystem + agency that helps across fundraising, marketing, and design.