What you’ll learn from Chris’s story
The importance of building a personal network
Meet Chris
Hi, I'm Chris Ryan, a 29-year-old digital marketing entrepreneur based in Denver, Colorado. Since 2021, I've called Denver home, enjoying the stability of being a homeowner and the flexibility of remote work.
What I do for work
I run Kismet Marketing LLC as the owner and chief strategist, leading a small, yet powerful, digital marketing agency. We specialize in social media management, full-service video production, SEO and digital branding.
The majority of our clients are in the financial services and real estate software sectors, however, my goal for the coming year is to branch out, working more with small and creative businesses within Denver, Colorado and Bend, Oregon.
My corporate background in digital marketing and multimedia production has been invaluable, allowing me to combine marketing strategies with content creation. This dual expertise is a key strength of Kismet, enabling us to create content that is not only visually compelling but also strategically deployed for maximum impact. My role involves managing client relations, finances, production tasks, strategy calls, and much more, ensuring that I'm involved at every stage of our projects.
As a business owner, my work hours fluctuate with the demands of the business. Some weeks are intense, clocking 60 hours or more, while others are more relaxed. The key is riding these ebbs and flows effectively. Initially, I balanced Kismet's growth with a full-time corporate job, working late nights to build the business. Now, Kismet is my main focus, allowing me to dedicate my time and resources solely to its growth.
Financial transparency
Financially, running a marketing agency offers limitless potential, though it's not a guaranteed path to wealth. Many freelancers and small agency owners make between $40,000 to $60,000 USD annually. However, with diligence, expertise, and maintaining strong client relationships, it's possible to scale up significantly. For instance, I've been able to achieve low six-figure earnings since Kismet's start, growing year-over-year except in 2023, which was a year of maintaining rather than scaling, due to my increased corporate responsibilities.
Join me for a typical work day
A typical day for me starts around 6 to 7 am. I aim to be an early riser to make the most of my day, but I also enjoy the routine of starting my mornings in a relaxed way. My partner and I both work remotely, and it has become part of our daily ritual to explore different coffee shops together. This has become a hobby as well as a crucial part of my work routine. We look for unique, local cafes with a good atmosphere and reliable Wi-Fi.
From about 8 am to 11 am, I’m at the coffee shop. This time is dedicated to handling emails, client communications, and outreach. I find that the change of environment helps me stay focused and inspired. During these hours, I also communicate with my team of part-time contractors, making sure everyone is on track with their tasks.
Around noon, I head back home for meetings. The most common times for my meetings are between 12 pm and 2:30 pm. These meetings can be with clients, team members, or potential new clients. I prefer to conduct these from home where I have a more formal setup and fewer distractions.
After my meetings, I take a quick lunch break and then dive into production tasks in the afternoon. This might include preparing for upcoming shoots, editing content, creating graphics, or tracking analytics. I like to keep a close eye on the performance of the content we produce, ensuring that we can demonstrate tangible results to our clients.
I try to wrap up my workday around 5 pm. I believe in maintaining a work-life balance, so I schedule my evenings for personal activities. Around 6 pm, I attend a yoga class, which helps me unwind and stay fit. After that, I either cook dinner or go out to eat with my partner. We both enjoy trying new restaurants and cuisines.
Even though I aim to finish work by 5 pm, my laptop is always within reach, and I often find myself checking emails or finishing up minor tasks until around 8 pm. I believe in being responsive to clients, but I'm also working on setting boundaries to avoid burnout.
My life outside of work
Balancing the unpredictability of finances as a business owner with personal responsibilities, like managing a mortgage, is another aspect that can limit the freedom of remote work.
Although my partner and I don't travel extensively at the moment, we enjoy local trips and have the flexibility to attend important events like weddings without needing to take time off. We love to explore Colorado's diverse landscapes, from the Rocky Mountains to the vibrant city scenes in Denver. Weekend camping trips are a favourite, offering a refreshing break from work and a chance to immerse ourselves in nature. These trips help rejuvenate our spirits and inspire creativity.
We're in that stage of life where many friends and family members are getting married so weddings have become a significant part of our travel schedule. This season alone, we have several weddings to attend across different states. The flexibility of remote work allows us to extend these trips, turning them into mini-vacations. For instance, we might spend an extra few days in a wedding location to explore the area, try new restaurants, and even visit local coffee shops for a change of scenery while working.
Challenges of remote working
Remote work and travel present unique challenges. One notable instance was managing work across three time zones, which initially affected the quality of my output while I was in Spain in 2023. I was juggling a company based in Australia, another in Denver, while working from a coworking space in a small Spanish town. The time differences made it difficult to balance client meetings and deliverables. I had to attend a community hike, rush back to shoot a TikTok video, and then hop on a meeting—all within a short timeframe. I made sure that I was still available as if I was back in the US which meant I sometimes had meetings in the middle of the night - I probably won’t put myself in that position again.
Focusing while working remotely can also be a challenge. The freedom to work from anywhere sometimes means distractions are plentiful. At home, I could be tempted to watch TV, do household chores, or browse the internet. To counteract this, I spend a lot of time and money at coffee shops. The change of environment helps me stay focused and productive. However, it’s not always easy to find the perfect spot with reliable Wi-Fi and a comfortable atmosphere, which can be frustrating.
Balancing the workload and avoiding burnout is another significant challenge. There are weeks where the workload is overwhelming, with multiple shoots, editing projects, client outreach, and administrative tasks piling up. During such times, it’s easy to work long hours without taking breaks, leading to burnout. I have learned the importance of setting boundaries and taking time to relax. However, it’s a constant struggle to balance being available for clients and taking care of my well-being.
Additionally, managing a remote team of contractors has its own set of challenges.
Coordinating across different time zones, ensuring consistent quality of work, and maintaining clear communication can be difficult. There are times when misunderstandings or delays occur due to the lack of face-to-face interaction. I have to make extra efforts to ensure everyone is on the same page and that projects are progressing smoothly.
Less to do with remote work, but another major challenge is the financial uncertainty that comes with running your own business. Unlike a regular paycheck from a corporate job, income as a business owner can be unpredictable. This financial variability can be daunting, especially with responsibilities like a mortgage. There have been months where finances were more tight, and I had to dip into my savings or work harder to secure new clients. This uncertainty requires careful financial planning and a solid emergency fund.
How I got started
My journey into freelancing began in June or July of 2020, during the height of the COVID-19 pandemic. At that time, I was living in the Bay Area, working full-time as a multimedia producer for an education technology company. The pandemic had a significant impact on daily life, especially in California, where restrictions were particularly strict. The Bay Area was completely shut down, and there was little to do outside of the home.
I was living with a roommate in downtown San Jose, and we found ourselves with a lot of time on our hands. The city, usually bustling with activity, was eerily quiet. It was a stark contrast to our expectations of city life, and it felt somewhat depressing. We were city boys for the first time, and the inability to explore and engage with the city was disheartening.
In this context of isolation and downtime, I decided to make the most of the situation by exploring new opportunities. One day, I came across a LinkedIn post from someone I had attended college with. She posted a call for someone with a marketing background who also played flag football. She worked for a large national brand and was looking for freelance help.
I decided to respond to her post. We connected, and she explained that her company needed help with SEO, creating articles, infographics, and long-form content to drive traffic to their websites. Their usual in-person events were cancelled due to the pandemic, and they needed to pivot to digital marketing strategies.
This became my first freelance client and them being a large national brand was incredibly fortunate for me. It provided a great portfolio piece and allowed me to start my freelance journey with substantial work. Initially, I pitched myself at $40 an hour, thinking it was a reasonable rate for someone starting out. However, the client recognized my value and offered to pay me $75 an hour. This generosity set a new standard for my rates moving forward and taught me the importance of advocating for fair compensation. I now do the same for my contractors, ensuring they are paid equitably.
At this point, I was still working full-time as a multimedia producer. Balancing my full-time job and growing freelance business was challenging but exhilarating. I spent my days working for the education technology company and my nights and weekends building Kismet Marketing. The demand for digital content was high, and I quickly found myself managing multiple projects.
As my freelance work grew, I took on more diverse projects. My first client, the large national brand, started asking me to create videos and handle social media coverage for their events as restrictions began to lift. They also asked for referrals for additional video work, which allowed me to expand my network and bring on other freelancers for larger projects.
During this period, I also took on small business clients in the San Jose area. Although they weren't as profitable as my larger client, they provided valuable experience and helped me build a diverse portfolio. I was handling everything from SEO and content creation to video production and social media management.
Despite the growing success of my freelance business, I was still working full-time. I moved to a new company, seeking leadership opportunities and greater challenges. During the interview process, I was upfront with the CEO about my freelance work. I made it clear that I had ongoing freelance commitments and didn't want to drop them. I positioned it as a positive aspect, demonstrating my entrepreneurial spirit and ability to manage multiple responsibilities. This transparency allowed me to grow my business without secrecy or conflict.
For several years, I balanced my full-time roles with growing Kismet Marketing. At one point, I was managing six to eight Kismet clients alongside my full-time leadership role at the new software company. This balancing act was challenging and led to a bit of burnout, but I was determined to keep both career paths moving forward.
How I managed to convince my boss to let me work from Spain
One of the most significant turning points in my remote work journey was convincing my boss to let me work from Spain in January 2023. This opportunity came about somewhat unexpectedly. I had come across Sun and Co, on Instagram, a co-living and co-working space in Spain. Intrigued by the concept, I reached out to them with a proposal: if they provided me with free housing for a month, I would help them improve their website. I want to preface that this was very unlike me; I'm not a person who goes by chance, I'm very methodical and pragmatic.
To my surprise and excitement, they accepted. This meant I now had to pitch the idea to my boss. At the time, I was working full-time in a critical role, leading a rebrand for the company. This was not an easy time to step away physically.
I scheduled a one-on-one meeting with my boss, who was the CMO at the time. In preparing for the meeting, I made sure to anticipate any concerns she might have and came ready with solutions. I approached the conversation with a clear and detailed plan:
Assuring Commitment: I assured my boss that I would not miss a single meeting and would maintain Denver hours despite being in Spain. This meant working from 3 pm to midnight Spain time to align with my team in Denver.
Demonstrating Value: I highlighted my consistent performance and how I had exceeded expectations. I shared the successes my team had achieved under my leadership and how my presence, albeit remote, would continue to drive those results.
Presenting the Opportunity: I explained the opportunity at Sun and Co. and how it aligned with my personal and professional growth. I emphasised that this experience would enhance my skills and broaden my perspectives, ultimately benefiting the company.
Detailed Plan: I provided a detailed plan of how I would manage my workload, ensuring that all projects, especially the critical rebrand, would stay on track. I outlined specific tasks and deadlines, showing that I had thought through the logistics.
Contingency Plan: I also presented a contingency plan for potential challenges, such as internet connectivity issues or time zone conflicts, demonstrating my preparedness for any obstacles.
My boss took this proposal to the CEO, and after a discussion, they approved it with the understanding that I would meet all my responsibilities without any disruptions. This approval marked the beginning of a new chapter in my remote work journey.
Discovering the Possibilities of Remote Work
My experience in Spain was a wake-up call to the possibilities of remote work. Before this, I had only stayed in hostels during international travels, which are not conducive to working. At Sun and Co., I met people from all over the world, each bringing unique perspectives and experiences. This diverse community, gathered in a small beach town in Spain, was eye-opening. It demonstrated that remote work could mean more than just working from home; it could involve travelling to different countries and fully immersing oneself in new cultures.
Inspired by this experience, I began to see the potential of co-living and co-working spaces as a business model. I even considered turning my own property into a co-living and co-working space. This concept aligns with my long-term goals and reflects my passion for creating flexible and innovative work environments.
Back to my story
A year and a bit after returning from Spain and still while working as a director at my full-time job, I faced a pivotal decision. Either double down on my corporate career or fully commit to my own business. Despite the security of a director’s salary, the prospect of working for myself and building my own success was far more appealing.
To be completely honest, I wanted to have an even bigger financial safety net but I had still been preparing for this since the start of the year. I had been paying ahead on my mortgage so I was several months ahead and had also saved up a chunk of money to get me by for quite a few months. This all gave me some breathing room, but in hindsight more would have been better.
In mid June 2024 I made the leap and for the first time after a short grace period, Kismet Marketing became my full-time endeavour.
My message to the world
For those looking to start a social media marketing agency or become a freelancer, my advice is to first gain experience. Many people jump into this field expecting quick success, hiring virtual assistants or relying on AI tools to cut corners. However, producing high-quality content requires a solid foundation of skills so I recommend getting a few years of experience with an employer first. This helps you learn important skills like interpersonal communication, how to set meetings, business and email etiquette, and how to manage expectations.
Building a network is also crucial. All of my contractors have been personal friends or former colleagues. My main contractor was my intern in 2019, and we have continued to work together and grow since then. I've also collaborated with people from college and other full-time roles. Maintaining relationships, treating contractors fairly, and paying them above market rate ensures loyalty and high-quality work.
What’s next for me
Before I jumped into Kismet full time and left my corporate job, I made sure to have a 1-year, 3-year, and 5-year business plan. This plan outlined what my numbers would look like to maintain the business, bring on staff, and scale effectively. In the next year, my primary goal is to get my full-time income from Kismet to a level similar to what it was when I had both a full-time role and Kismet. Right now, I am about halfway to where I need to be to maintain my current lifestyle. I'm doing a lot of outreach, cold emailing, and list building to source new business.
Within the year, I would love to go on one or two co-living/co-working trips. However, Denver will remain my base. My goal is to bring on one or two employees, including a full-time video contractor and an account manager to handle client outreach, maintain relationships, and manage admin work. As I build my team and they start to take on more responsibilities, I will then have the opportunity to pursue new ventures and expand into surrounding communities.
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