Why does a person shirk the relative reliability of a job to start a business?
(And don’t tell me about how jobs are just as unreliable. Of the 100,000 people who will read this post, how many have made more money, and more consistent money, with less stress, with their startup than with their day jobs?)
- Be my own boss
- The chance to make lots of money
- Work my own hours
- Even if it’s more work, at least it’s mine
- Change the world
It’s not just high-tech startups either (except the arrogant desire to mold the daily lives of all people). From journalist Jon Milward’s research on prostitutes — another sort of freelancer:
When I asked the 30 escorts what the benefits of the job are, the main one (27 mentions) was money, followed by being their own boss (22) and the working hours (20).
Another thing they have in common:
I find most high-tech startup founders are software engineers enamored with the idea of waking late, sidling up to a coffeeshop table, pecking away at an IDE, getting into the zone for hours at a stretch, and doing what they love — coding something of their own invention.
But the real life of a startup founder isn’t that at all. How many people have written to me about their “startup” which can’t produce enough revenue to shrug off the yoke of W2’s and consulting work, exactly because the founder is only interested in banging away at TextMate instead of crafting the home page, testing the adverts, building the social following, toiling through customer development (even though you think you already know the answers), thrilling a potential customer over tech support, struggling with server uptime in the middle of the night, keeping the books so the IRS doesn’t nail you in three years, tuning email and to-do processing techniques to squeeze out more productivity, keeping healthy (or suffer) with food, exercise, sleep, and mental well-being, to operate at peak performance and avoid burn-out, staying on top of the trends and language of the industry media that customers are reading, fretting with lawyers over a nit in a vendor’s Terms of Service, messing about with purchase orders, and so on.
Never mind managing consultants or employees! Get eight of those and you’ll be lucky to be in the coding zone once a month.
Not to worry, the escorts don’t love the work either. Continuing from Jon’s article:
The sex ranked dead last with only 8 women including it as a positive. Of course, there’s no reason that should come as a shock to anyone. How many people, after all, could say that they do their job first and foremost because of what it is and not what it pays?
Startup founders want to say that, though. They want to say they love the work and hope it also pays off in the long run. Even if it’s not really true day-to-day.
So what do they love, if it’s not the work, and not the pay?
To me it comes down to that phrase that both high-tech startup founders and UK escorts rank so highly: Be my own boss.
I’ve said that too. But are you really your own boss? What does that mean?
Does it mean you decide what to do every day? Yes, except you’re a slave to the realities of running a business capable of throwing off even $10,000/mo in profit to a single founder. You can’t just “decide” to avoid working on sales and marketing and still have a business that you can rightly claim is more stable than a job.
Does it mean you decide your working hours? Yes, except you’re working more hours, and more stressful hours, than you’ve ever worked before. Sure it’s fulfilling, sure you “own” it, but is that a sensible sacrifice to the altar of “your own boss?”
Does it mean you make all the decisions? Yes, except you can’t imagine how draining it is to make 100 decisions a day, 1000 days in a row. But yes, in the words of Ben Horowitz, “Some employees make products, some make sales; the CEO makes decisions.” And more ominously, “the CEO must have the courage to bet the company on a direction even though she does not know if the direction is right.” I know, you’re a founder, you want the responsibility and the power both. But years of constant daily decision-making is harder than you think. And don’t forget it also means you must “decide” that you have to fire someone even though you like them personally and you know they have a family with a spouse who doesn’t work and it will be hard for them to get another job. Must, you understand, even though you’re “deciding.”
Does it mean no one can tell you what to do? Yes, except if you don’t listen to what customers are telling you to do, you’ll build a product no one wants to use. If you have a co-founder, are you not responsible to her as well? If you take a seed round, are you not responsible to your investors? If you hire employees, are you not responsible to them?
Today I run a 60-person organization, plus investors and a board. Never do I feel like I’m my own boss. I’m responsible to my executive team to support them, empower them, feed them, sometimes corral them, and often to get out of their way. I’m responsible to everyone at WP Engine to maintain an environment that’s happy, fun, open, honest, and yet productive, where we’re as proud of the quality and quantity of our work as we are of how we treat each other. I’m responsible to our 10,000+ customers to fulfill the promises we make around service and product. I’m responsible to the board and the shareholders (which in our case includes 100% of our employees!) to maximize the long-term value of those shares through solid financials, healthy SaaS metrics, and growing as fast as possible (but not faster). I’m responsible to my wife and daughter, because I refuse to sacrifice my relationship with my soulmate and best friend, or to not bear witness to the miracle that is a child growing from a tangle of reflexes to a thoughtful citizen.
I spend literally all my time working to fulfill my commitments to others. Am I my own boss?
It would be arrogant and even dangerous for me to have the mindset of being “my own boss.” I certainly would never want to work for — or with — a person accountable to no one because “I’m the boss.”
Still, perhaps you’re reading this and thinking “Screw all that! That sounds horrible. I do want to be the boss.” How do you go about legitimately “being your own boss,” without all these shackles?
- Single founder. Co-founders are a two-edged sword. Most successful, large companies have multiple founders (yes that’s from real data). But, “founder break-up” is also a leading cause of young companies failing. Two founders means double the work-output and an accomplice for the emotional roller coaster. But it means you’re accountable to someone else, as an equal, and you’re already not your own boss.
- No employees. An employee isn’t just a contractor with health benefits. This is their career. They have dreams of what they’ll build, how they’ll grow, what it means for them to give up half their waking hours to this organization, and what the company does in return besides sign paychecks. If there’s not enough money for payroll, they get paid first. If there’s not enough money for them either, how do they feed their families? The responsibility on you is enormous. If you want to be your own boss, you shouldn’t be anyone else’s boss either.
- No tech support. (Or almost.) High-quality tech support is one of the few advantages of small business. Then again, it ties you to a real-time inbox, and ties you to interrupt-driven event-processing. It’s OK to have little-to-no tech support, especially on an inexpensive product, or at least to set expectations that support questions might go unanswered for days. This might sound like I’m advocating for a terrible customer experience, but consider that many products that people love and use daily are accompanied by zero tech support (GMail, Twitter, Facebook, Instagram, Vine).
- Nothing real-time. If it matters that your hosted product works 24/7, then you’re a slave to uptime. If it’s a bad customer experience unless they can contact you at a specific time and day, then you’re a slave to your customers’ calendars. If it matters that your product send an email precisely when another event happens, you’re a slave to technology that has low tolerance for failure.
- No investors. Money is never free. Even if you take money from your dentist, he’ll still want to know how things are going, ask for favors now and then to help a friend with their website, etc.. Advisors are good. Investors have skin in the game.
- Focus on profitability, not high-growth. To control your destiny you need consistent, reliable cash-flow. Otherwise you’re not your own boss; you’re a slave to whatever will actually give you money. Also, the other bullet points above are generally contrary to high-growth companies. Rather, focus on creating something that people will pay money for, today, and much more money than it costs to acquire or serve them. You’re optimizing for your own freedom, not for highest-growth or even highest-total-revenue.
One final word of caution. Don’t think for one minute that the bullets above are easier (or harder) than the path I’ve chosen.
I executed exactly these bullet points at Smart Bear for over two years. It worked out well, but it was just as difficult and just as much stress as WP Engine is now. There is no easy road.
So, how badly do you want to be your own boss? What does that mean to you? Let’s keep the discussion alive in the comments.