Starting a Company of One—My Story
SO FAR THIS BOOK HAS covered a lot of stories, data, and studies on why growth should be questioned in the quest to run and maintain a company of one (or really, any business you’d like to sustain long-term). Now we can move our attention to the final piece of the puzzle—what exactly we can do to go from zero to start for a company of one.
For this chapter, we’re going to focus on what it looks like to start something on your own, even though we now know that a company of one can flourish within a larger organization. I hope that the material presented in this book has shown you that this counterintuitive approach to work can benefit both your wallet and your overall enjoyment of work, and that working for yourself can make a lot of sense. Now let’s see how to put it into practice—how to build something that’s too small and resilient to fail. I’ll start with my own origin story.
In the mid-1990s, I was at the University of Toronto, studying computer science and artificial intelligence—which, given the current trends, seems like it would have been really useful to stick with. But I hated it. I would finish studying and completing school assignments as quickly as possible so I could focus my efforts on what I was really curious about: this new thing called the internet, and building web pages on it with design and code.
One site I created, a dictionary for slang words (words that otherwise wouldn’t be in “real” dictionaries), began to get a lot of press and notice. The attention came not just from publications that found the internet interesting and exciting, but also from design agencies that figured their clients could benefit from having websites—and they could benefit from being paid to build them.
As a result, I dropped out of school and went to work full-time at an agency in Toronto, designing and building websites. That work went well for a while, but eventually I wasn’t happy with the “love ’em and leave ’em” attitude at the agency, which focused on the quantity of work more than the quality of relationships. After a year and a half of seeing that the agency wasn’t keeping clients for multiple engagements, I figured the job wasn’t right for me and quit to find a job at some other agency where my purpose would be more aligned with theirs.
Then a funny thing happened the day after I quit. I was all set to go to the library to figure out how to write a résumé (since I hadn’t ever written one and the internet wasn’t the vast resource it is now) when the phone began to ring. Clients from the agency I had just left were calling because they had heard I was no longer working there. It turns out that they had noticed my desire to deliver more value to each project and wanted to bring their business to whichever company I landed at.
I then had a thought I’d never had before—perhaps I could work for myself and build the exact type of business I wanted to run, matching my purpose with the work I was doing. Instead of going to the library to write a résumé, I went to the library to figure out how to start a business. And so began my work of almost twenty years, working for myself.
I didn’t call it a company of one at the time, but in effect, that’s exactly what I was doing.
In the beginning, I made far more mistakes than progress, so by telling my story, I hope I can save you a bit of heartache and the kind of real financial loss I incurred early on.
BUT FIRST, SOME CAVEATS
It seems as though every article on the internet about working for yourself extols the virtues of casting off the shackles of full-time employment to become free and happy working on your own from various beaches across the globe, with a laptop on your lap and a mai tai in your hand.
We’re constantly getting the message that working for ourselves is the answer to all our problems and the only surefire way to get ahead. In fact, even though I’ve worked for myself longer than most people, I still don’t think it’s the best option for everyone. Not because some people aren’t talented enough to start their own company of one, but because it just doesn’t make sense for everyone. It all depends on what you want to do and how you want to do it.
When you’re the boss of you, there’s no HR department to handle payroll, benefits, and training. There’s no accounting department to handle payables and receivables or to chase after folks who haven’t paid you yet. There’s no sales and marketing team drumming up new business leads for you. On top of the main skill you use to make money, you’ve got to do all the other jobs as well. Some folks are fine with doing this kind of work, but it may not be how others want to spend their days. The people I know with their own company of one spend approximately half of their time, or less, doing their core skill (writing, designing, programming, etc.). They spend the rest of their time on the business—chasing leads, doing their books, communicating with clients or customers, marketing, and so forth.
With all this “Work for yourself! It’s better than whatever you’re doing now!” messaging out there, people often end up falling in love with the idea of working for themselves without understanding the actual day-to-day work required to be their own boss. Or as Austin Kleon cleverly puts it, “People want to be the noun without doing the verb.” They want the job title of founder or CEO, or a business card and a fancy website with a new logo, but they forget or overlook the daily rigors of running a business of their own. Having a brilliant idea or a passion to build a successful business is not enough. Ideas and dreams are nice, but they’re also cheap and meaningless if you don’t take action and do the work to make them happen.
The harder—much harder—part is making the dream happen every day. Some days you’re buried in accounting spreadsheets; other days, you’re on the third round of revisions from a client, or dealing with an irate customer. The daily slog is what separates wannabe business owners from those who make it a reality.
Working for yourself requires ego and purpose in equal measure. I started working for myself because I figured I could foster client relationships better than the agency where I worked. That became my purpose—not to be the best designer (which I’m not even sure is possible), but to run a business focused on client relationships. So ego is involved, not in a bad way but in a “I know I can do this better” sort of way. If you don’t think it’s possible to do better, or you don’t care if it is, there’s no point doing your own thing. In that case, it’s fine to work for someone else—they’re already established and have people handling the jobs you probably don’t want to be doing anyway.
Purpose is required in that you have to have a north star that will drive you long-term without blinking out. A desire to get rich quick or achieve business fame isn’t going to motivate you for long, since neither is quickly possible, regardless of who you are. There are much easier ways to make money or become famous in the world. Why do you want to work for yourself? What will drive you to keep going when things get rough or take longer than you hoped they would? What will make it worth it when you’re stuck in the day-to-day minutiae of running a business?
For myself, I happen to like choices. I like that I can choose to make less money by saying no to a project or a client or a customer I don’t think is a good fit for me. I like that I can choose to unplug for three months at a time and go on camping road trips across American deserts with my wife. I like that I can pick what I work on next, rather than have work handed down to me. I like that I can work on Saturday if I want, and go hiking on Wednesday. This freedom of choice is my north star. Yes, it’s taken some time to get here, and I had to be okay with not having nearly as much freedom in the beginning as I do now. After all, bills need to be paid and sometimes the best client isn’t the best fit but he’s the one who’s here right now and willing to pay you this month. Still, even in the rough patches, my purpose—my freedom of choice—is what’s driven me forward.
I don’t mean to give you a downer of a message—only to challenge your idea of wanting to work for yourself, just as you should challenge the notion that all growth is beneficial. If you’re like “Yes, I’m in,” then that’s awesome—I hope this book gives you a bit of a roadmap to building your own company of one. But if it doesn’t make sense for you right now (or ever), that’s okay too. Perhaps your path is becoming a company of one at the organization you’re part of and building a brilliant and resilient career there. I would never say that there’s one singular path to business success and enjoyment for everyone to take.
Let’s say I had to start my business tomorrow from scratch, with no existing clients or following. How would I build an audience? How would I attract customers?
This is how lots of people start businesses every day: knowing how to do something well (their craft), but without an existing group of people eager to work with them. Where do you begin?
With my skill set, I’d start by listening to people who are looking to hire web designers or have already hired web designers, since that’s the most marketable skill I’ve got. How are these potential clients conducting their search for a designer? Where are they searching? What questions do they have about the process? If they’ve had a bad experience with a web designer, what went wrong? What do they wish they’d known before starting a web design project?
Then I’d offer to help with their questions. Is there anything in particular they want to know? Do they want a second set of eyes to look at something? Do they want to brainstorm on what to do next? Do they want a second opinion? Is there anything they want to know about the industry? I would add small bits of helpful advice without offering my own services or charging them. More important, I wouldn’t be pushy about it—I’d just look for folks who have questions I have answers to.
This free help I offer wouldn’t be a month of work or a redesign of their whole website, but rather emails and chats, either in person or by phone or Skype. Basically, I would offer a free consult or a project roadmapping session. In this way, I’d learn the key factors involved when people are thinking about hiring a web designer and gain insight into why and how they end up choosing to hire one.
Just like Alex Franzen in Chapter 4, I’d start by finding a single person to offer my knowledge to. Then another. And another. I’d talk to as many people as possible, until I start to notice definite trends where people are having issues or not understanding things. And I’d do all of this without pitching or selling myself once. I’d simply offer help or advice to anyone who wants it.
Talking to people this way would do two things. First, it gives me be an opportunity to share my knowledge with the type of people I want to work with (without asking for anything in return). Second, I’d learn what my future audience is looking for, where they’re getting hung up in projects in my field, and how I can communicate with them effectively to help solve those problems.
Long before I’d start selling anyone anything, I’d be building relationships with the people I’ve helped in some way. I wouldn’t build this following so I could “promote” or sell to them later. I’d build and foster relationships with these people so I could continue learning from them. And these would be mutually beneficial relationships: they’d receive my help and I’d receive their knowledge.
Most important, I’d do this fact-finding/mini-consulting while I was working somewhere else, probably at a full-time job. I wouldn’t dive headfirst into building my own company from the ground up, because I wouldn’t know yet if it was an idea that I could execute well enough to make into a sustainable living.
From there the path could go several ways. Through a blog, I could write publicly about what I learned and eventually compile my posts into a book—full of insight into common client issues and how they can be resolved (as I did in writing a previous book). Or I could use my newly acquired knowledge to create my own services, since I’d know where my potential audience needed the most help. I’d probably do both things, with confidence that the people I’d been helping would promote what I came up with, and with no need on my part to constantly promote/sell at them.
And this is the key—the people I’d helped would help me precisely because I had helped them (although I would never expect it of them). In my own company of one, every single business I consulted with or roadmapped for wanted to hire me to execute the plan I’d helped them come up with. Even when I was charging good money for consulting, I’d still be at the top of each client’s list to hire. Being helpful proved to be a great lead-generation funnel.
My new business would be based on helping others first, with a contract for web design or design consulting coming later. I’d do it this way not because I frown on capitalism and want to sit around a Skype video-call singing “Kumbaya,” but because I know this is how you build a loyal client base and following.
Many people would view this approach as advice for building a charity or aiming a business only at your close friends—it couldn’t possibly be applied to a business that makes enough money to put clothes on the children, keep food on the table, and pay the rent. But this is precisely how I built a business that, for over a decade, has had a waiting list of four to five months. It’s how I released books that have sold tens of thousands of copies. It’s how I’ve approached my entrepreneurial work for years. I’ve simply used my skills to help others, because I enjoy doing it. And I’ve offered this help for free, in small doses at first, and then later for good money in larger doses.
This approach mirrors the mind-set of a company of one, in that you can start right away, without investing a ton of money in resources, tools, or automation software. You can hit your MVPr quickly by offering services first, then products as demand increases for those services. To get started, you need a computer and an internet connection, and that’s it.
The best thing about gearing your business to make money now rather than spending money now to maybe make more money later is that profit happens faster. You don’t need investors, or investment on your part, or investments from venture capitalists. There’s no need for a certain hardware or software, and no need to use secret tactics or strategies. All you need is to be a decent human being with a valued skill set and a willingness to share what you know with people who’ll listen.
My own company started this way, after I decided not to find another agency job. At the time I was still a teenager, living at home and working in my parents’ basement on a computer I had built myself out of cheap parts. I focused on the work I could do immediately in order to make enough money to cover living expenses once I moved out (which I did quickly, heading west) and then to not only make a living but save as much as I could.
The traditional way to establish a business is to start by getting an investment (from the bank, from a rich relative, from a VC), then work hard for a long time to create a perfect product. This way of working, however, has a lot of drawbacks. You have to make a ton of assumptions about the market, your positioning, and your customers, and then, before launching, you have to spend a lot of money and then just wait for the results to come in.
Taking the opposite approach, the company-of-one approach, can work just as well, if not better. Being able to launch your business without any investment (other than a tiny bit of your own time), you don’t have to make as many assumptions about the market, your product, or your potential customers. You can start your company of one simply by making your business idea as small as possible, then launching quickly.
For example, Creative Class (my own first online course) started out as an idea for thirty lessons, which would have taken me four to six months to create. I also wanted to develop course software to run it (another four to six months of work). I resisted the urge to spend four to six months writing lessons, however, and instead started with seven lessons and existing software; this way I could launch in a month instead of a year. The quick launch enabled me to see what worked and what didn’t with an actual audience, and then I could adjust, iterate, and improve. After starting with seven lessons, I added seven more, based on the feedback I received from students. With the second round of seven lessons, I was able to get my course out quickly, have it generate money, and then adjust it based on real feedback from paying customers. By the sixth version of the course, it was making enough money to sustain me.
While obviously the company-of-one method is to start with as little as possible and then grow it slowly or as needed, there are still some factors that need to be considered.
Too often businesses focus only on revenue. For companies of one, expenses are just as important, since the sooner you can reach MVPr the better.
Let’s look at it this way. If you offer a service for $1,000 and your monthly expenses are $2,000, then you need at least three clients per month to be profitable. If you need $4,000 to cover your expenses, then you need at least five clients to be profitable. Honestly consider two questions: In the beginning, can you reduce any of your expenses so that you can do less work to be profitable each month? And how likely is it that you’ll get the number of clients or customers you need each month to be profitable? If acquiring three clients seems doable but having five would stretch you too thin, you’ve got to either reduce your overall costs or raise your rates. Consider how long it takes to find a client, court the client, work with the client, and then finish up each client’s project. Is there enough time in a month to do that five times? Or even three?
The same questions need to be asked of a product business. If you price your product at $50 and your costs are $30, then you don’t need to sell 40 products ($2,000/$50 gross = 40 units) to reach $2,000; rather, you need to sell 100 ($2,000/$20 in profit = 100 units). Again, if your expenses are $4,000, you need to sell 200 units. How likely is that?
Another factor related to money is how you spend your time. Every day you spend developing a product is a day you aren’t really making money from it, unless you’ve done preorders or crowdfunding. How can you get an initial version of your product to market quickly to start building revenue?
Money is why a lot of companies of one begin as side projects: their path to MVPr in order to cover the founder’s expenses can take a bit of time. I offset my own living expenses at first by living at home with my parents (hey, I was only nineteen), and then by taking a few years to slowly transition fully from services to products—and not until the products were routinely making more than what I was charging for services.
Small businesses can be taken advantage of, ripped off, or screwed out of money they’re owed—sometimes by larger businesses, but sometimes by businesses the same size. This is why having legal systems in place right from the start is important.
You need to ensure, first, that your business entity is set up properly for the country and region you’re operating from, and second, that your business is removed by one layer from you personally. In other words, your business should be its own legal entity—a corporation in most countries or an LLC in the United States. That way, should anything go wrong in your business, it is your business that is liable, not you personally. All money should go into your business directly, not straight to you, and then you should be paid out, by salary or dividends. There are so many different ways to structure a business—based on your needs, what you provide to clients or customers, and where you’re located—that you probably need a lawyer (and an accountant sometimes) to help you set up the right business for you.
Next, after you’ve separated your company of one from yourself personally, you need to prevent your company from being taken advantage of. With service-based businesses, this means having contracts between your business and your clients. In the beginning, you can source contracts fairly cheaply online. Eventually, it makes sense to enlist the help of a lawyer who’s familiar with both your area of practice and how laws work in your geographic location and who, of course, can make sure that your contract is sound. For a product-based business, this means having users agree to your terms of service before they pay you for what you’re selling.
The reason for having a business lawyer—and one who’s on contract, not an employee—is not so that you can sue everyone, but so that lawsuits rarely happen. I pay my own business lawyer a small yearly fee as a retainer so that I can ask him a few questions now and then, as a preventive measure. He makes sure not only that the threat of my business being sued is as small as possible, but that the need for my business to sue anyone else is as small as possible too. Having to take someone to court, or being taken to court, would put a lot of stress and strain on the daily operations of my company of one.
The best lawyer for a company of one is one who understands the type of business you do and is happy to work with a business of your size. And in general, I’ve found out the hard way that it’s never a smart idea to be either the biggest or the smallest client of anyone you hire for their professional services.
I’ve always believed that good accountants should save you more money than they charge. This belief may be misguided—I have no studies or data to back it up—but nevertheless, my own accountants definitely do this.
To find the best accountant for your company of one, look for a firm or individual who has knowledge of your type of work and familiarity with businesses of your size. My own business needs a firm that understands how online business works, and how to deal with revenue that comes from selling digital products primarily in the United States (in U.S. dollars) while my business is in Canada (operating in Canadian dollars).
An accountant is not just a person you talk to at the end of your business year when you file your taxes. You can use an accountant as an adviser on all things related to government requests, on how to stay up to date with financial laws (so you don’t inadvertently break them), on sound ways to pay yourself and pay your expenses, and on how best to structure your business to pay the least amount in taxes.
I talk to my own accountant every few months—whenever I’m thinking about making any changes, adding a new product or partnership, or anticipating a new and large expense—or anytime I get a letter from the government to my business (since those typically aren’t written in understandable language). I also have my accountant audit my bookkeeping to ensure that everything is done correctly and nothing is missed. I would rather focus on making money than have to figure out the convoluted details of how much I owe the government, so I gladly lean on my accountant for this service. Again, I hire accountants as independent consultants, not as employees, as a company of one doesn’t need a full-time accountant.
As I mentioned in the legal section, you need to make sure your business is separated from yourself, and to this end, the first thing you need to do is open a separate bank account for your business and then, from that account, pay yourself either a dividend or a salary. Since revenue from my work can sometimes be inconsistent, I’ve always figured my base salary as the average I’ve made in profit (not revenue) for the last twelve months, minus 25 to 30 percent (to set aside for taxes). Before raising my salary if my profits increase, I also take into consideration the minimum amount I need each month to live on and be comfortable. With my twelve-month average profit in mind, and not going too far past my minimum living expenses, I can set myself a fairly steady salary. Obviously, you can change this up if you find you need less money—or more—but keep in mind that the more money you take out of your business, the more it’s taxed.
The biggest thing to consider when you work for yourself is that even if you’re paying yourself the average of the last twelve months, there’s no guarantee you’ll make the same profit moving forward. That’s why it’s important to have a “runway buffer”—a bit of savings to cover yourself and your expenses if there’s a slow month or two. Because I like to play it very safe, I have a six-month runway buffer of liquid assets that I can easily and quickly access if I need to. Other people I know are comfortable with a three-month buffer, so just decide yourself what works for you. Personally, I wasn’t even willing to start working on my own full-time until I had a runway buffer saved up.
Another factor in how much you pay yourself is how much time off you’d like. If you want to take four weeks a year as vacation, then you’ll need to set aside a month’s worth of extra savings (on top of your runway buffer). Unless you’ve got a recurring income stream (like recurring revenue from monthly software licenses), if you aren’t working, you may not be making money.
Having a runway buffer of liquid savings also helps when unexpected events come up. A family member falling ill or passing away can require you to take time off that you hadn’t planned for. In this event a recurring income stream and runway buffer can be a great help at a difficult time.
Alongside a salary and a runway buffer, I truly think companies of one should invest as much money as they can save up in passive investments like index funds. If inflation is approximately 3 percent per year, then you’re losing money on any assets you’ve got that aren’t making at least 3 percent per year in returns. This applies, by the way, to all the money in your bank account, since checking and savings accounts pay barely any interest.
Since I don’t have an employer putting money into a 401(k) or Registered Retirement Savings Plan, created by the Canadian government for Canadians like me, I’ve got to consider how I can make the most of being in the prime of my earning potential and save for the future, when that might not be the case. And just as I do with my salary, I have an automatic withdrawal set up to transfer money from my bank account into my investment account each month—in an amount that’s high enough to matter long-term but low enough not to affect my liquid assets.
The goal here is to work your money in small steps. First, ensure that your company of one is making enough profit to cover your living expenses. Second, make sure you’ve got enough of a runway buffer built up to work full-time at your company of one, even if things get slow. Third, with your salary and runway buffer covered, you can reinvest money in your company; if things are going well, you should be able to get a better than 3 percent return on such an investment. Alternatively, if you don’t need to invest more in your company—maybe your business costs are covered and you have no reason to grow them—you can invest any extra money in something like index funds.
I use a robo-investor with very low management fees and keep my money in index funds that require no upkeep on my end. Once a quarter, I check in on my investments, and if I have questions I talk to someone at the company. But since these investments are long-term, I’m not worried about daily or even monthly losses or gains. I just want to see my money grow over decades.
Depending on the country you live in, medical coverage and insurance can be a huge factor in deciding if you’re going to go on your own and start a company of one.
Jonnie Hallman, the founder of Cushion (which offers scheduling software for freelancers), found that the number-one reason his fellow Americans don’t venture out and start their own companies is their worry about the cost of health care. Insurance can definitely cost more when you aren’t part of an employer or group plan, so shop around before you make your choice.
Luckily in many other countries, like Canada, basic health care is available to every citizen. Canadians only have to worry about obtaining extended medical insurance, critical injury insurance (in case they’re injured for a long period of time), and life insurance. But in the United States, health care coverage continues to be an issue. As a company of one, you’ll definitely find it worth your while to do some outreach to see where you can obtain health and life insurance.
Regardless of where you’re located, there are usually groups you can join to take advantage of bulk savings, such as professional associations, chambers of commerce, and business groups.
And now, with the nitty-gritty of money and insurance coverage out of the way, we can turn to the question of the lifestyle you want your company of one to allow you to have. Regardless of the type of work you do, how you work is always going to involve a lifestyle choice. The benefit of a company of one is that you can build your lifestyle around it, optimizing for both profit and your own happiness.
The first step is to develop a consistent, healthy monthly revenue to cover costs, your runway buffer, and investments. Once you take care of those considerations, a beautiful thing happens: you’re presented with choices. You can choose to make more money, if that’s what you want, or you can choose to work the same and make the same amount. If you make the latter choice, you can then start to prioritize. Do you want to spend more time with your family? Do you want to explore the world? Do you want to spend more time experimenting with new business ideas and opportunities?
By removing the hurdle of having to consider scaling up in all areas at all times when things are going well, you can open yourself up to investing in enjoying your own life. You will have the freedom to enjoy the benefits of having figured out how to make “enough.”
And then, if our goals are similar, I hope to see you out hiking on the trails in the wild Pacific Northwest one day soon.
BEGIN TO THINK ABOUT:
· Your purpose or reasoning in starting your own company of one, and whether it will hold up over time
· How you could start your own company of one right now, with some first version of what you want to do
· What you need to do to set up your company of one correctly and responsibly, both legally and financially