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Founder or Freelancer: How to Succeed in Business as a Solo Act

Just because you’ve started a company — or gone freelance — doesn’t mean you know anything about how to actually make it work. Sarah Brown gets advice from the pros on how to hone the hustle and set yourself up for success.
Illustration by BoF
  • Sarah Brown

NEW YORK, United States — We are in the age of the entrepreneur, big and small. Whether starting a company or striking out as a solo act, people are doing business for themselves more and more, leaving corporate America or avoiding its confines altogether from the get-go. It's risky, it's rewarding. It requires persistent self-advocacy, savvy negotiation, collaboration, creativity, critical decision-making — constantly — and surrounding oneself with the right advisors. Just because you are talented at your craft doesn't mean you know anything about business (yet). Here, a group of entrepreneurs who have made it — and are making it, daily — weigh in on how to set yourself up for success in today's topsy-turvy, exciting, terrifying, and ever-changing climate. Consider it the new playbook, as written by the players.

1. Be Your Own Advocate

For anyone going into business for her or himself, you are now selling something: you. That can be an adjustment in itself: permanent sales-mode for many of the previously un-sales-y.

"You have to be your own self-advocate, and early on, with clarity," said Kim Vernon, who launched her strategic consulting firm, the Vernon Company, 12 years ago after serving as a vice president at Prada and chief marketing officer at Calvin Klein.

Be bold, communicate your worth and your services — and be able to back it up.

"A website is a really good tool to justify the work and your rate, and to give people a clear definition of what you do," said Jen Brill, founder and creative director of Brill Brill Studio, a creative agency that works with clients like Proenza Schouler and Nike. "Show your value and how you can elevate what a client is doing. There are a million people who can do it at any rate, and you are an expert in your field. Show case studies of your past work so they can say, 'she's done X and Y and Z for these brands, and look at the return.'"

You have to be your own self-advocate, and early on, with clarity.

When it comes to defending her rate during negotiations for brand collaborations and influencer programming, Jen Atkin — the celebrity hairstylist who founded Mane Addicts, a digital platform for the hair-obsessed, in 2014, and the hair care line Ouai in 2016 — approaches discussions like a lawyer preparing a case. "I will do the work and have the facts behind me," said Atkin, whose 2.8 million Instagram followers regularly see her styling clients Kendall Jenner and Bella Hadid, and on vacation with friends Chrissy Teigen and John Legend.

“I will call and say, ‘Here is my media value. I have looked at Tribe Dynamics and Dash Hudson. I know how much my posts are worth. If you would like to be part of it, let’s talk about it.’ Remind people in a positive way of your worth. You can’t be afraid to do that,” she said.

2. Make It Business

One of the biggest challenges of being a gun for hire is navigating the nuanced gulf between catching up over coffee, having a meeting (or two), and moving things to a place where you are getting paid for your time and your talent.

It would be nice if everything were as easy as just shouting Kate Moss's mantra, "No Fee, No Me" (literally the icing on her recent birthday cake). But, generally, before a real working relationship ensues, there is a prerequisite back-and-fourth with potential clients, almost like deciding if you want a second date where someone has to actually pay for dinner.

If you start to think, 'I need to be compensated for this time,' you probably do.

"Business development" is one way to characterise this period where broad ideas are exchanged and a relationship is explored, said Julie Gilhart, who left her role as fashion director at Barneys NY in 2011 for a stint advising Amazon, and now focuses her consulting business on sustainability and emerging talent. The thing is, when ideas are your currency, and your time is what you're selling, this "dating" period can get uncomfortable at a certain point.

“If you start to think, ‘I need to be compensated for this time,’ you probably do,” said Gilhart. “It’s setting a boundary — and you do have to set boundaries.”

“There’s a certain balance between showing up and putting in the time, showing a client you’re inspired and that you care, and then walking away and leaving the rest up to them,” said Brill. “If they want to make it official, they will.”

3. Set Terms ASAP — and Get Them on Paper

So how does one gracefully set boundaries and move to the place of in fact being compensated for one’s time, advice, and services? At the close of a productive exploratory meeting, immediately offer to send a proposal, said Richard Koenigsberg, CPA, a partner at Spielman Koenigsberg & Parker who advises clients across the media and entertainment industries. (Including me.)

This turns any conversation — no matter how casual — into real business. “The proposal implies that you need to be paid. And then they’ll decide,” he said. “You’ll spend a lot less time spinning your wheels and people will respect you more when you set the terms of your engagement at the outset of your conversation.”

Vernon views establishing a “scope of work” for any project as “the most essential tool,” as it lays the groundwork for everything that follows. “You need to approach the client having a clear understanding of what’s expected,” she said. “As quickly as possible, get a scope of work together you both can edit. It usually means drafting it yourself, and who better to draft what you’re going to do than you? You can insert your experience there. It gives you an advantage to say, ‘I’m going to be able to do all these things,’ and takes the ambiguity out of it. Really general scopes can cause confusion and missed expectations on one side or the other. When you’re specific, what is not in the scope is very clear, and that’s an advantage, also.”

Setting a scope also helps determine the rate. “You can attach a dollar amount because you can tell how much time it’s going to take and you know there’s a baseline amount of work you’re going to do,” said Vernon. If a client pushes back on a proposed fee, “you start reducing the scope until you both feel comfortable that you’ll have a certain level of results and time,” she said.

When determining your rate, look at the industry standard and consider where you fall on the experience spectrum and what you are bringing to the table. Also, ask trusted colleagues for advice. “You don’t want to price yourself out of something, where you’re so far above it that they turn around and hire someone else,” cautions Vernon.

The important thing is that before beginning any work, “you need to have things buttoned up,” said Koenigsberg. Contracts are helpful in that they set clear terms, to avoid surprises. For example, “If you’re doing something potentially open-ended or over the course of time,” said Vernon, “you’ve got to structure your agreement to address those points: If you go beyond the scope, it’s written in stone.”

To be selling your own expertise is not as easy as having a big brand name behind you.

Contracts cover your bases to help ensure you are not being taken advantage of, even unintentionally. “Many times I find myself in a company’s business deck,” said Gilhart. “You should know that — if someone is putting your name and picture and bio in their deck. It’s like you’re blessing that project, in a sense. You should include that in your contract: Your name, etc. is only used with your permission.” Indeed, your own equity is part of the value you bring to a project, and it is part of what a client is paying for, especially if they wish to use your halo for their own marketing purposes and to establish legitimacy in a particular area.

4. Get Comfortable Talking About Money

This can be the most awkward part of negotiating on one’s own behalf. Talking actual dollars can feel grubby and inelegant (at first), but it shouldn’t, and it’s something that we — women, especially — need to get over. Is there anything else in the world you would attempt to buy and then be surprised when the seller brought up the price?

“To be selling your own expertise is not as easy as having a big brand name behind you,” conceded Vernon, but, “that part about feeling like you’re sticking your hand out — that’s the wrong mindset. It takes realising that the world you’re in, you’re for hire.”

In addition to being able to simply broach the topic of rate structure without cringing, becoming truly versed in finance gives one the tools to negotiate creatively and with confidence.

Even in a post-Lean In, post-Girlboss moment, it's not unusual today for women to feel uncomfortable talking about money. In many cases, it's just not how we were brought up. "I think about imposter syndrome pretty much all the time. It's so real, and figuring out how to neutralise it is imperative," said Moj Mahdara, an entrepreneur who built and sold two companies prior to co-founding Beautycon Media in 2014.

Beyond all the PR halo moments of feminism, it's time to do the work of understanding,

“Men have had generations of institutional knowledge passed down to each other; they have cultural references and codes,” explained Mahdara. “We are the first true generation of women who are actually trying to achieve entrepreneurial sameness as our male counterparts. Sadly, there is such a lack of financial literacy between us. It’s cool we’re all empowered now, but what happens when the first thing we ask for doesn’t work, when what you want isn’t available? There is a male literacy of being able to work through it.”

“Beyond all the PR halo moments of feminism, it’s time to do the work of understanding,” said Mahdara. “It’s one thing to ask for what you want, it’s another thing to negotiate from a position of understanding,” she said. “Guys like to negotiate — it’s fun for them. We have to decide that if we’re going to be in business, we should enjoy the process, too, instead of it being miserable for us. We have to talk to each other, beyond the broad strokes, about the technical execution of it all. If someone is going to offer you options, do you even know what this stuff means?”

5. Understand Equity

“Many times, start-ups will offer equity because they use their stock as currency rather than having to come up with the cash to pay you,” said Koenigsberg. When accepting equity — as part of an advisor or board member agreement, or in combination with a reduced cash fee or salary — here’s what to know, and what to ask:

Very simply, “you’ve got to equate that equity to something,” said Koenigsberg. “When a number of shares are offered, you have to know the value of those shares. What percentage of the company do they represent? What is the value of those shares today when granted to me, and how does that compare to the value of the service I’m offering? If it’s a start-up, the value is close to zero, so do I think the company has potential; am I willing to roll the dice? What, ultimately, do I think they’ll be worth? Shares don’t pay your rent initially.”

Studying a company’s capitalisation table — the schedule of all of the shares that have been issued, the various classes of stock, and the value of cash investments that have been made — helps provide this picture.

“You need to ask for the cap table so you understand what the shares are valued at, how many shares are out there, and where you stand in the waterfall of payment,” explained Koenigsberg. I.e. if the company sells for a certain ballpark amount some day, will your slice be enough to buy you a house — or a pack of gum? “Any time you’re granted shares you should be getting the cap table,” he said.

6. Build a Team of Advisors Around You

In Mike Monteiro’s viral career advice lecture “Fuck You, Pay Me” (…Google it), the San Francisco-based graphic designer declares, “you are at the point that you need a lawyer when you have decided to be a professional.”

You want to bring on your advisory team as early as possible.

Indeed, part of being a good businessperson is recognising that there are even better businesspeople out there, specialised in their given field and armed with expertise and experience you do not have. They are guardian angels — on retainer.

“You want to bring on your advisory team as early as possible because you can pay now, or pay later,” said Koenigsberg. “The cost of not structuring yourself properly at the outset far outweighs the cost you will incur.”

“What’s helped me most is having a good business manager,” said Gilhart. “You need somebody to be that nuts-and-bolts person. A business manager will help with the numbers, put you on a budget and advise you about what you’re doing with your own money. They understand how much you need to live on, how much you need to save, and do you want to take two vacations a year? Lawyers are great and you need them, but a good business manager can read a contract and is with you daily, or part-time. That’s been invaluable.”

Outside advisors can also take certain responsibilities off of your plate, so you are free to focus on that which you excel, and enjoy. Brill, for example, engages IMG to handle her firm’s financial negotiations with clients. “It never feels sexy when you’re talking about creative and your job is to inspire, and then you have to discuss money,” she said. “It makes relationships really complicated, bogs me down and keeps me from the creative. I like having that not in my space.”

Hire people who will protect you.

Koenigsberg compares the outsourcing of certain services to the billing person at a doctor’s office: “When you go to the doctor, the doctor never discusses the cost of the service; you meet the businessperson in the office once you’ve decided to use him or her. You are now the doctor and that’s the part you are going to concentrate on, and you’re going to turn it over to your advisors to discuss the business terms,” he said.

“Hire people who will protect you,” said Atkin, who credits her lawyer, agent, and business manager with “working tirelessly to make sure I’m getting what’s fair.”

Once you’ve got your advisors together, introduce them. “If you can get them where they know each other, that’s amazing,” said Gilhart. “When something comes up, you have a team you can talk with together. That’s given me a real feeling of security.”

7. Like Who You’re Working With

“Before I go into business with someone, I want to make sure I really, really like them and that there is some thread to the same values,” said Gilhart. “I only want to work with people who are going to have a positive impact on the planet. It may be in a big way or a small way, or that they have potential. You have to set some criteria for yourself. It’s about searching for the quality of people, not just the names of the companies, that are asking you to do business. If you don’t have like-minded values, every step is going to be a lot harder.”

When something doesn’t feel right, said Brill, don’t be afraid to walk away: “I heard something the other day that really resonated with me: ‘Go where it’s warm.’ If I get a vibe I don’t like, I generally don’t gravitate toward those projects,” she said. “I’m really transparent with my collaborators and I expect the same. A lot of things happen between A and Z. It’s important that everyone gets what they need and that you are upfront and honest about it.”

If you don't have like-minded values, every step is going to be a lot harder.

That goes for partners within your own business, too. When fashion editors Meredith Melling and Valerie Macaulay left Vogue in the fall of 2013 to start their consulting and styling business, La Marque (they would go on to launch the direct-to-consumer apparel company, La Ligne, in 2016), they felt confident forming a business partnership because they already knew how to work together.

“We were colleagues before we were friends,” said Melling. “We had experienced each other in the workplace before, so I knew a lot of Valerie’s strengths, and they compensated for some of my weaknesses, and vice versa. Going out on your own is a massive undertaking. It can ruin friendships unless you approach it the right way: ‘This is not about our friendship; this is about our business.’ We can be on different sides of an issue, come to resolution, and then go have a drink.”

8. Keep Evolving

A final word of encouragement to all embarking upon business ventures large and small: “All the rules are being broken now,” said Brill, brightly. “Creativity is being found everywhere and it’s far more democratic. The fuddy-duddies who are masters have competition; all the rule-breakers can do something special. I’m not scared. I’m inspired by what’s happening,” she said. “The things I like — my taste, my collaborators — are constantly changing. As long as you’re not sticking to one form and you keep evolving, you will do just fine in this climate.”

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The Business of Fashion

Agenda-setting intelligence, analysis and advice for the global fashion community.
State of Fashion 2023
© 2022 The Business of Fashion. All rights reserved. For more information read our Terms & Conditions and Privacy policy.
State of Fashion 2023