We recently connected with Michael Keelen and have shared our conversation below.

Michael, thanks for joining us, excited to have you contributing your stories and insights. Are you happier as a business owner? Do you sometimes think about what it would be like to just have a regular job?

I have mixed feelings about running my own firm, but mostly I really enjoy it, and the benefits certainly outweigh the drawbacks. For example, I previously worked 10 years as a high school teacher, and the level of freedom afforded by that work is very low. I woke up very early to begin teaching very early, and a whole decade was spent doing high stakes, high stress work from bell to bell to bell, and then usually into the evenings. Work like that has tremendous value for students, communities, and even teachers, but the toll from teaching can feel enormous, and the highest levels of pay require lots of expensive education and decades in the field for what will ultimately be higher-stakes, higher-stress positions for pay that is still supremely subpar given the importance of the work. I am happy and proud of the work I did as an educator, but 10 years was as much as I could give that system.

Working for myself for nearly two years has been different and better than expected in several ways. For starters, I wake up when the sun or my body tell me it’s time, not when the alarm wakes me up in the dark. As long as no matters are pressing in the morning, I have the luxury of leaning into my workday slowly, working at a comfortable pace, and taking long or short breaks when needed. I can’t overstate how good and different that aspect feels on the mind and body.

I also have the pleasure of working with professional, talented, and hard-working content creators who understand the importance of building bodies of digital work about topics they care about with the goal that their contributions to either moments in time or to the culture at large will resonate with people in specific ways. These creators provide real value through their work, like honest product reviews and recommendations; makeup, haircare, and skincare tutorials for beginnings and those who are more advanced; and perhaps most importantly, real-life models for young people who themselves may be trying to navigate and strike balances between the demands of school, work, home life and, if there’s time left in the day, something else they really care about and may want to speak out about. Traditional education provides immense value in ways that I think are increasingly underappreciated, but it’s equally important that young people can connect with others who share their interests and values, who make them feel seen and heard, and who show them viable paths toward, for example, their own creative and financial freedom. And if it’s not that deep, then at they very least these creators make fun videos that many people love watching at the end of their long days. Being able to provide management to creators who offer these kinds of value to hundreds of thousands of people just through their social media posts means a lot to me and the creators I represent.

But like any line of work, this one has a couple minor drawbacks. For example, almost all of my interactions are conducted via email with people I’ve never met, so I don’t really have any coworkers, and that can make the workday feel pretty solitary. This decentralized way of working with people and entities all around the world also tends to slow the process of negotiating a deal, producing deliverables, and getting paid. Instead of showing up to a location for eight hours to work with a team of colleagues who are all focused on completing the same project, this job requires lots of emailing, waiting, and following-up, so seemingly small jobs often take weeks or months to complete. There are lots of moving parts between multiple entities, so just getting the job done usually requires a lot of patience and persistence. The solitude and slowness of the pace of production are not features I’m not accustomed to or fully adjusted to yet, but these are small complaints really.

Another drawback of the decentralized nature of this type of work is that the industry feels more ad hoc than any other that I’ve worked in. For example, instead of managing employees who understand an organization’s missions, procedures, and rules, every creator is an independent contractor with the freedom create their own way of doing things. Each of them operates differently for different purposes and attracts different audiences and interest from brands, so understanding each party’s needs and interests in each situation requires a level of adaptability that working within the structures of a corporate environment might not always require. Not only is working with each creator different, it’s also true that every brand operates differently. Some brands have 2-page contracts that require no edits, while others send 20-page contracts filled with legal landmines, and some don’t have contracts at all, so I end up writing them for them. Some brands present paid work opportunities with very little notice to decide, tight parameters and deadlines, and arguably semi-predatory contracts that don’t match the terms negotiated in email, then have no qualms about paying invoices late. On the other end of the spectrum are brands could not be more easy to work with and somehow manage to pay invoices within days of receipt. These variables and others can make the work a little more challenging in some ways, but they are all part of the calculus, and really none of this is much to complain over.

All of that is to say this: I don’t have to wonder what it’s like to work for others, because I worked for others my entire life. My goal now is to grow Millay Media into an elite talent agency, and that will take a lot of hard work on my part and on the parts of the creators I represent. Hopefully in time I will be able to hire employees who can take some of the tedium off my plate and help me to tackle more projects for more clients, but in the meantime, I don’t mind doing the hard work at all–in fact I enjoy it–and I am still far happier today reading contracts alone in my pajamas than living by the tyranny of the alarm and school bells!

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

For the past 25 years I worked in retail sales and management, market research management, very briefly in finance and logistics, and eventually in education for a decade. This diversity of work combined with my post-secondary education gave me a range of skills that can be applied across lots of fields.

Millay Media was born several years ago because a content creator I knew was receiving terrible management from someone who, in the end, was also stealing large sums of money from her. In her search for new management, she and I realized that all of the services the old manager was supposed to be providing could be provided more effectively by me and without the risk of theft, so I simply applied the skills I had learned in my previous work to this new line of work. For example, skills and experiences like managing large and long-running projects, managing large groups of coworkers and then students; negotiating; higher-order reading, writing, and editing, and others lend themselves naturally to many different lines of work. Learning some of the nuances of this work and applying certain skills has been a combination that has gotten Millay Media at least this far. That said, I am still learning every day, so I’m excited about any collaboration or new ideas that will make our work better, more efficient, and more lucrative.

In terms of the day-to-day, the bulk of what I do is the boring stuff most content creators don’t want to do or may not be experienced in doing: responding to emails, negotiating rates and deliverables, arranging shipments, reading and editing contracts, invoicing and collecting payments, and a lot more. I also help obtain invitations to parties and events so the creators can mix with other creators and brand reps and learn about product launches before anyone else. Part of my work involves going to these events too, which is usually a lot of fun! Sometimes I facilitate contact between creators and other media outlets like magazines and TV shows who are interested in their work, and I also help land them modeling gigs from time to time.

I also offer general consultation and strategy to the extent each creator needs or wants it, but mostly I free up their time to do what they do best, which is to create valuable and fun social media content for their followers! The creators I represent depend on me to do what I think is important work for them, so it means a lot that they trust me to play this small role in the building their respective careers.

Can you talk to us about how you funded your business?

One of the major benefits of representing and managing content creators is that the business itself requires almost no capital to begin. My initial set-up costs were minimal business start-up fees with the state, the purchases of a new laptop and iPhone, and the small amount I paid a website builder to create Millay Media’s website.

My ongoing monthly expenses include cell phone and wifi bills, fees from banks and payment platforms, web hosting charges, some office supplies, and occasional other incidental things, but of course all of these expenses and even my home office are tax deductible.

Thankfully I do not require retail space, inventory, or employees, so my overheard is practically nothing. This doesn’t mean more capital wouldn’t be extremely helpful to my business, but in terms of start-up costs and ongoing operating expenses, I can’t imagine too many businesses that requires less.

Can you tell us about what’s worked well for you in terms of growing your clientele?

My clientele are both the creators I represent and manage as well as the brands who pay us to create promotional content for them, and both clientele lists should be cultivated and grown with equal care.

To grow the talent list is to stay in business, so it is important that I provide honest and effective services to those I currently represent. In so doing, I can feel confident asking any prospective client I might interview to reach out to these clients for feedback about their experiences working with me, and this positive feedback can give sometimes nervous creators the confidence they need to take a leap of faith into a management relationship with someone they don’t know personally. If a creator feels confident taking that leap, then it’s all about delivering for her.

To grow the list of brand clients, it’s important that I represent creators who post good content, first and foremost. Good creators will attract large followings, generate higher engagement on posts, and receive greater interest from brands who may want to pay them to make promotional content. When those bands reach out, it becomes imperative that they immediately feel like their needs and goals are understood, are important to us, and will be met. The result is that brands usually express a real gratitude that we make the business end of their creative marketing endeavor as smooth and successful as possible. Ultimately our goal is that our final product meets the brands’ creative and marketing objectives and performs as well on social media as we can possibly control. Because we tend to deliver, we get a lot of return business from multiple clients, which we are always incredibly thankful for!

Contact Info:

• Website: https://www.millaymedia.com
• Instagram: https://www.instagram.com/millaymedia/
• Other: https://www.tiktok.com/@millaymedia

Image Credits

in bathtub is Grace Debetaz aka @debetaz on IG and @shakespearesidechick on TT
on couch is Daria Afshar aka @dariaafshar_ on IG and @dariaafshar6 on TT
creator with shimmer is Sammy Shields aka @sammy_shields on IG and @sammyshields_ on TT
creator wearing black shirt is Alisa Molina aka @flwrmamii on IG and @flwrmami on TT