Escorts, Startups, and the questionable promise of being your own boss


Why does a person shirk the relative reliability of a job to start a business?


let go

(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?)

Common answers:

  • 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.

For every micro-business single-founder success story like Marco Arment or Rob Walling, there are a thousand others who aren’t generating enough profit to sustain themselves.

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.


40 responses to “Escorts, Startups, and the questionable promise of being your own boss”

  1. great post – forget where i first saw it (your blog, someone else’s?) but the org chart upside down – with all the management team at the bottom and people who take care of customers and coding and whatnot at the top, seems apropos. In particular, the CEO/founder at the bottom of that “tree” (inverted hierarchy) serving all of those above them doing your best to allow them to be successful and productive.

    As soon as BP3 stopped being a 2-man show, even when we took on our first contractor, we started feeling responsible for doing the best we can to provide for the team. And when you’re bootstrapping, the big money is always “next year” or further out because every year you have a really good reason to put most of your profit back into the business to grow it, rather than take it out to buy nice things or invest in the stock market.

  2. Good list, but for me the important points were ‘control’ and ‘the ability to choose who to work with’ (and more importantly ‘who not to work with’)

  3. Being your own boss doesn’t have to mean doing whatever you want regardless of the consequences. It isn’t just about being your own boss. It may be about succeeding with your idea by creating something that matters, ala what people like Seth Godin or Jason Fried talk about.

    In that case, being your own boss might simply mean less BS and more leverage to do what you have to do to succeed. I have worked with 7 startups to date. I founded 4 of them, had 2 happy acquisitions, an IPO, 2 failures, and 1 still very much on the path (one of those single founder Marco Arment things and its working very nicely, thank you).

    Of the 4 I founded, the 2 happy acquisitions and the 1 still running are in that group. Could be as much as a 75% success rate. Of the 3 I joined, I got 1 IPO. Great gig, but financially, less successful than the 2 acquisitions. Only a 33% success rate.

    The 2 failures I joined are what convinced me to quit working with VC’s and bootstrap my own company. They were both unforced errors meaning the marketplace didn’t reject us, but they were seriously mismanaged by investors and those pesky bosses. The 1 failure on one I founded was a market judgement. It is radically easier to be judged by the market than by your own team’s failure to perform.

    In terms of the other things you mention, see 37Signal’s writing for all those burnout hours (they don’t advocate it and built their company on less than 40 hours a week per founder in the beginning) and on the money, no comparison. I’ve worked for a number of big companies and while the salary is nice, it’s a drop in the bucket compared to what you can make running your own show. Even my current 1 man SaaS company startup is paying more than I can get as CEO of a raw startup:

    So take heart, it’s not as dismal as some make it out to be. Get started on your own business.

  4. Good post. I do like “being my own boss” and agree with you that this is a loaded statement but if spending an entire Saturday and Sunday away from administrative crap and building my product is something I view as a “great weekend” then I have to disagree with you and say I do love the work. It’s tedious, stressful, and keeps you questioning yourself at every turn but in the end conversations with customers and potential customers give me the energy to view the work as a great use of time because I’m building something people want. Don’t you agree that layered beneath all of the administrative BS there’s a core product value that gets founders up out of bed everyday? If you employ lean startup practices and vet that there is demand for what you believe to be awesome (and tweak your product accordingly), isn’t there such thing as a healthy, legitimate passion for your core product?

    Also, curious to hear your thoughts on how long one can remain a single founder? With ASmartBear or WP Engine did you start out as such then prove the concept, monetize it profitably, and then hire executives who were co-founders in name? Eventually you have to take a co-founder to incentivize the right people, no?

    • RE: “Don’t you agree that layered beneath all of the administrative BS there’s a core product value that gets founders up out of bed everyday? ”

      Yes, that’s exactly my point. That the core of what excites you generates the energy required to get through all of the stuff you actually have to do. You wouldn’t need to “spent Sat and Sun away from admin crap” if you didn’t have so much admin crap in the first place.

      You can remain a single founder forever, of course. There’s lots of examples of that in practice. There are lots of examples too of taking on someone later in the company’s life — 3-5 years in — who behaves in every way as a “co-founder” and thus deserves title and comp accordingly None of these are “required” for success, just different sensible things that happen.

  5. Interesting points and valid all. I think a key point to the large startup founder equation, at least the ones that are successful at being founders, is that they want to change the way something is done. The drive to make that change and find best paths to that change through thoughtful experimentation creates an incentive as well as a path for that potential success. That willingness to sacrifice for a great idea and the potential for a nice exit, in my opinion, can offset the difficulties you present.

    Again thanks for the great articles Jason, as always fun an informative to read.

    • I agree “changing how things are done” is a major point.

      The bootstrappers just want to find any number of people who agree “this is better.” The fundraisers take this to the next level of intensity and say they want to “change the world.”

  6. Well put Jason…and actually, I am one of the few people who DO love their work too..but then again, I doing everything you listed above…<3 thnx

  7. Being your own boss means:

    – not spending time again and again discussing the same topics every week in boring meetings
    – not being told to do meaningless work
    – not seeing idiots being promoted

    – not seeing the company losing marketshare year after year even if they still say “next year we will gain marketshare again”

  8. >For every micro-business single-founder success story like Marco Arment or Rob Walling, there are a thousand others who aren’t generating enough profit to sustain themselves.

    I think ‘1 in a thousand’ is an exaggeration. I have run my own 1-man software business for the last 8 years and I know quite a few others that do as well.

    I follow all of the bullet points you list for being your own boss, except ‘No tech support’. I reply to customer emails 364 days a year. Taking a laptop on holiday seems a small price to pay for having your own business. I guess the customers are my boss. But as I have thousands of customers I am not beholden to any one of them and have plenty of freedom.

    • BTW, Andy, if you do ever get sick of tech support, consider Sarah Hatter’s company, It might be worth it to you someday.

  9. > Why does a person shirk the relative reliability of a job to start a business?

    I would add “to challenge yourself” to the list of reasons to ditch a job to start a business. If you’re not challenged by your job, building a business is certainly a way to make things more challenging. Almost always more challenging than anticipated though.

    I’d also add “the thrill competing” to the list. I’ve played competitive sports all my life and translating the competitive drive into my work has been fun. You can certainly feed the need to compete as an employee, but the rewards of outdoing your competition are far less and thus the motivation.

    > 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.

    Didn’t you have employees at Smart Bear though?

  10. >>You’re optimizing for your own freedom, not for highest-growth
    or even highest-total-revenue.

    This is the key point most people pursuing “freedom” start with, but soon forget.

    If you consume startup podcasts, blogs, conferences, etc… it’s almost impossible not to find yourself getting sucked into the tactics and strategies that funded/high-growth companies are pursuing such as: offering a free plan, attacking ideas that can only be profitable “at scale,” not charging from customer #1, going after two-sided markets, pursuing the TechCrunch launch, etc…

    If you are optimizing for your freedom, print out Jason’s sentence and stick it on your monitor (or your cat). Because the startup world will do its best, almost daily, to make you forget it.

  11. what a *great* post!

    it’s comforting to know I was right in my feeling that I’m a prostitute or glorified plumber/sparky to my clients

  12. This was a great early warning of what life is really like “behind the curtain of self-employment”.

    Although I tend to guesstimate that the people who most need this early warning will not even find it, nor read it, nor learn the lessons.

    As humans, we frequently take action based on some illusional utopia of what things will be like. Most advertising plays into this concept. But without the illusion, we probably would not take the risk if we can’t imagine the reward.

    Usually we won’t heed good advice until we fail and then need to search for reasons / meaning & solutions. Many times well intentioned advice turns out to be just plain wrong.

    I see you are on Clarity. Does the content of this blog post come from conversation you’ve had with dreamers who are just starting out, or is it after they are in deep water that they call for help?

    The concept and freedom imagined by “being your own boss” speaks loudly about the current problems with “work” and “jobs”. But some workplaces are transforming themselves into more of a contractor / customer situation where as an employee you are acting with more internal drive to accomplish goals to help your boss / company, instead of just being told what to do like an automaton.

    The real difficulty (which applies even more during self-employment) is persuading people to “see things your way” and getting them to do it the way you want (the typical role of a salesperson). Lacking that ability makes any “job” difficult because you have no control, which leads to feelings of unhappiness, depression, then not caring about your “job” performance. Without this ability in your own business, you won’t be able to get paid.

    Still, self-employment is one of those things you have to try to see how you will like it. And depending on your personality, risk acceptance, and recovery speed, your success will depend on preparation, internal thoughts (optimist / pessimist) and agility to correct problems as they unexpectedly appear. It’s like 1 big optimization loop, forever.

    I’m effed because I can never go back to working for someone else, after experiencing the near-death thrills of the highs and lows of self-employment. So I must make this work.

    • I do speak with a lot of entrepreneurs, but this article is just from my own heart and experience. Of course this is the sort of thing where everyone needs to find his own path. Hopefully my musings will not be used to persuade, but rather to encourage introspection.

  13. So, to stretch your analogy a bit… You’re saying investors are pimps. :)

    Seriously though, I have “been my own boss” for 15-ish years. I get your point that, in giving up a day job, we trade one physical boss for what seems like a hundred others but even in my J-O-B days I put in more than any sane employee would. I didn’t do it for my boss. I did it because it’s who I am. I did it because I don’t know how not to.

    So today, I still put in more than any sane person would but now I’m fine with it if people think I’m just trying to impress the boss. Because I am. All 101 of them. And that is what makes me happy.

  14. > the alter of “your own boss?”

    Should be “altar” I think.

  15. Thanks for sharing your thoughts from the CEO’s chair. It reminds me of a great quote I heard recently: “If you want to be free to sail the 7 seas, you must be a slave to the compass.”

    • Excellent quote, The major definition, wide and complex, not too hard to understand to the few words people. Thank you.

  16. Maybe it’s not being your own boss… maybe it’s being able to choose your own bosses?

  17. I don’t know why being one’s own boss is so popular; I don’t actually want that. I guess I’ll never be a hooker

  18. It’s not easy to find a job that you like as an employee either, and nowadays it’s not easy to find a job at all.
    Moreover if you want to grow as an employee in most cases you have to become a manager which is as stressfull as being your own boss. Therefor for the same stress i prefer being my own boss.
    It’s sad but it’s true that being your own boss does not mean write all day the code you like, but only few weeks in a year maybe. Anyway if you can afford being 3 years without a salary i think it’s somehing everybody should try at once, at worst you go back being an employee and you learned something new: “admire and respect the next company that gives you a job because you learned how hard is to create a profit when your boss was only the market”

  19. Being my own boss sounds horrible. I like the idea of being responsible for as much as possible.

  20. >> “You’re optimizing for your own freedom, not for highest-growth or even highest-total revenue.”

    Businesses that are not optimized for freedom can develop entangling relationships that make it difficult for you to “be your own boss.” Rather than constructing the relationship in terms of boss and subordinate, I like to think of it as, “Who are my stakeholders? Who has a vested interest in my business?” The more stakeholders I have, the less freedom I can enjoy. Investors, Customers, Suppliers, and Employees all bring their own interests into the mix.

    The goal is to make a product that is self-sustaining, so that others do not rely on your continued effort, but rather the quality of the product you have made. At least that’s what we’re trying to do at

  21. Wow, what an awesome post. I couldn’t decide which point stood out as more important than the other – probably because they all carry so much weight. Thinking about it as “optimizing for freedom” is interesting – and easy to forget. It’s stressful and scary making decisions but the drive is to imagine saying one day “I did it!” and “be free”. What that means will only become clear to us if we reach that point, I’m sure! And there will probably not be as much freedom as we though when we started :)

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