Not sure what type of poverty he's talking about, but I certainly cant afford to fly off to Thailand at the moment...
How does that work? Do those people have giant savings accounts, and am I just dumb with my money? Or do they do freelance work on the side?
I have decent savings etc., but having followed the path of college -> grad school (where I worked as a research assistant) -> startup, I have never been to Asia/South America because I either have the time but not the money, or the money but not the time. My getaway has been driving to Santa Cruz for the Sunday once every few weeks.
I feel like I'm missing out on something here- and I'm not ashamed to say that I'm a bit jealous of those people and that I wish I could do the same. Coding on a Thailand beach between a scuba diving session and an afternoon of surfing sounds pretty nice.
They won't, however, understand that they could have had exactly the same life if they had chosen to delay the 'fun' just a few years. Guess how I know ;)
All it takes is for you not to buy this one car today at age 30 and the money will compound into a life of exotic beach vacations for all your grandchildren and beyond.
Edit: And for the people who don't have a trust fund, like me, you can always take a job with remote teams, which is what I just did.
Also depending on when you fly, and with some little research, you can get fairly cheap tickets.
If you know you will be in a precarious or idle situation for X weeks, you can balance the cost of staying here (US/Canada) for those X weeks (food, accommodation and some activities) vs flying there and saving a ton on food/accommodation/activities.
It seems odd but it's completely true.
It also helps that I don't have a mortgage to pay.
I've even met some of the guys coding on beaches in Thailand or Bali, they are quite laid back and zen. I'm not sure I could do it though, I'm still very much an American (meaning, puritan/work ethic roots), and would feel uncomfortable being out of the office for too long.
From my count, he has had 3-4 jobs in 3 years. Why would you want to hire someone who can't even stick with his own company?
So, this isn't a parable to apply to entrepreneurs in general. It only applies to quitters.
What's more, the design industry runs on freelancing. Consequently, direct-to-fulltime positions rarely open up for non-management positions, since most design firms have a cadre of long term contractors already waiting to make the jump. My wife was laid off from a design firm, and had 2 interviews in a year for full time positions. The rest of the time, she contracted. I had 3 interviews last week, and 2 this week and 3 more next week, with several companies in the wings.
At the same time, since it's a freelance industry, there are always people trying to farm out contract opportunities, which suggests that the author isn't interested in finding paying work, just in finding a paycheck.
Finally, even more than in software, you are your portfolio. It's really almost anyone cares about. If the author can't find >any< work, he should look there first.
Finally, I call bullshit on 'any good employee will leave'. It's a very design culture thing to think that professional relationships are inherently competitive rather than cooperative in nature.
The author of the book I quote is trying to elucidate the point that you should hire people who are better than you. Don't be afraid that they might leave. He drives that point home with the rule that anyone good will leave, so go ahead and hire 'em anyway.
Constructive criticism: I think the author's difficulties are probably more about his overall positioning than his history of entrepreneurial pursuits. For better or worse, positioning can mean the difference between getting lots of job offers and getting none.
The first thing I noticed in looking at the author's LinkedIn profile, which is the first result when you Google his name, is that it tells me more about what he's done than what he has actually accomplished. That's not helpful because prospective employers don't just want to know where you've worked, they want to know what you've achieved. If I were the author, I would rewrite my job descriptions to focus on the tangible benefits realized by my contributions. Right now, I can't figure out what value the author has created for his companies/clients/employers because it's simply not described.
Also, certain red flags simply aren't likely to be overlooked. Examples of these red flags include:
1. No full-time roles.
2. A history of job hopping (i.e. most/lots of stints under 18-24 months)
3. Jobs with overlapping dates.
4. Unexplained gaps in employment history.
5. No discernible career "path" (i.e. being all over the place in terms of what you've done).
6. Lots of moving around (geographically).
7. Bizarre job titles.
8. Job title progression that is inconsistent with a traditional development path (i.e. a jump from an entry-level job title to a senior-level job title in less than a year is likely going to be questioned).
9. Public musings in which you paint yourself as financially strained, burnt out, confused, etc.
Obviously, you can not and should not lie about your work history, so when these sorts of red flags exist, there might not be an easy way to deal with them. But I don't get the impression that the author has really looked at his CV and made an effort to argue compellingly that he brings a lot to the table. So blaming his entrepreneurial past for his failure to find a job is, in my opinion, misguided.
Finally, the author can't expect a good outcome if he's not where the jobs he's interested in are. If, say, I was interested in meeting the author for lunch next week to discuss a job opening, I would be unable to do so because he's in Thailand. And I, like most other employers, am not going to wait until "mid-September" for the privilege of interviewing him.
Coming to work on time and staying with a company for at least 2 years is a competence in itself. Job hopping is absolutely justified for use as discriminatory criteria.
Yes many of us have had a 6mo to 1 year job. One such job on a resume won't kill it. Neither will 2. But if you have a 5-7 year work history of 1 year jobs, that's not so impressive.
Candidates have to be realistic: most employers can't thoroughly evaluate every candidate, so certain red flags are going to be used as filters. Have a bunch of red flags? For better or worse, a recruiter or prospective employer is going to assume that where there's smoke, there's fire, probably without even talking to you.
At the end of the day, if you're looking for a job, it's up to you to sell yourself effectively. Far too many people assume that because they're competent, their competence will be evident to others. But hiring managers or recruiters generally don't see more than what you put in front of them.
If you're not strategic about how you position yourself and/or you're too lazy to put together a convincing "pitch", prospective employers will have no way of seeing the real you. And even if the supply of obviously good technical candidates is often limited today, the risks of a bad hire are generally too high to warrant taking a chance on someone who was incapable of presenting a compelling CV or "story" in the first place.
You typically run into two scenarios. The first is a manager --your would-be boss-- who, upon seeing what you've done feels threatened. A CTO might not feel good about hiring an ex-CTO as a rank-and-file engineer. The second scenario is that of a business owner who, upon learning about your entrepreneurial experience is concerned about hiring someone who might come in, learn the business and potentially become a competitor.
Yes, there's also the concern about someone pulling anchor early to go off on their own in an unrelated direction. It costs a lot of money to bring someone onboard.
My conclusion at the time was that in this fashion entrepreneurship can be a curse. It can be nearly impossible to land a "regular" job because of it. In my case, after much frustration I decided that my only path was to run my own show again and off I went.
If you limit yourself to teams with a product that has "moat", your entrepreneurial streak won't threaten them. (Although the churn concern remains, so a lot of talk is needed to see how visions and plans for the future collide.)
Brooks, you sound like you were made for sales. Maybe try catering your resume towards those positions?
Anyway, I'm an unfulfilled critic, so I don't know if your reading this, but here are the things that made my head spin about your post.
1) You editorialize a third party synopsis of your life into a headline without any indication that you're making a parody or something. "One accidental entrepreneur is finding it hard to" (This reminds me of someone during a manic episode)
2) You build your story out of clichés, but they seem incompatible with each other. (described as both "accidental entrepreneur" and "serial entrepreneur")
3) Totally ignore all important or interesting details that might indicate something about you or what your experience is. (leaving company i started for all the 'normal' and uncomfortable reasons? What?)
4) Generally weird stuff. Give me a job? If you're an entrepreneur, you'd know you wouldn't hire anyone with that attitude! Jetsetting in poverty?
Anyway, best of luck. I'm sure you'll find somewhere you fit in. You sound like you're made out of enthusiasm, and that rocks. It'd be interesting to know more of the facts of your story- I think sometimes the more specific detail of a thing you can share, the more powerful it can be. (I bet one uncomfortable thing that happened to you would be cooler for me to read about than a two paragraph synopsis of the last few years of your life even!) Also I want to know how much money your parents give you =D
I'd describe myself as an "accidental" and "serial" entrepreneur as well. The first bit means that you never expected to work for yourself. As for the "serial" part, if the companies you start aren't complete successes but aren't complete failures, it is easy to spend years trying to bootstrap multiple ideas. After you struggle along for several years regular employment starts looking pretty good (salary! vacation! benefits!), especially as you get older and want to start a family or buy a house or something.
As for the rest, I agree with the parent poster that it is harder to get an institutional job after years of self-employment. Part of the problem is that entrepreneurship is like a black pool -- what people see in it is mostly the reflection of their own prejudices. I suspect this is actually one of unstated reasons there is such an emphasis on getting funding, finding accelerators, etc. and why there is such aversion to the idea of bootstrapping. At the least, people who make their businesses as institutionally respectable as possible and collect salary from investors during the process are rarely berated for taking a vacation before starting a new job! :)
