Limited Life Experience + Overgeneralization = ADVICE
The argument posed by the author looks good so long as he selectively chooses his examples (dropbox in this case). There's far too much chaos in startups to ever know what the best possible outcome is, so a founder can never come to the proposed conclusion of mediocrity (in fact, there's so much gray area that any conclusion is really just a reflection of founder confidence).
Seriously though, I'm not saying you need to worship everything that these kinds of posts say. I'm just saying that one shouldn't go to the opposite extreme.
So we gave our shares to the last guy, and he's still running the company today - 9 years later. We've gone on to do other things, which are arguably more exciting, while he still sits around with two employees and tries to squeeze every penny out of the business while going nowhere.
Leaving was one of the best decisions I ever made. Leave or shut the company down if it enters a quagmire.
I do not think he would still be doing it after 9 years if he would totally hate it. I know people that do relativly mediocre jobs with mediocre pay but they still enjoy life and dont really want or need to improve their job situation.
If you want to do it that bad you'll think of something.
I recently handed in my resignation. I finish in 2 weeks. I don't have any new work to go to (yet), and my savings+overdraft will only get me through 1-2 months at most. The idea is that I'll do contract work to build up some reputation, then hopefully land some bigger projects and build a team. Perhaps give me the flexibility to work on personal projects that might go somewhere. I was like you, I kept saying I'd start a company when I had a good idea. In the end I realised it wasn't the lack of idea holding me back, it was the fear of failing. I decided that failing wasn't something to be afraid of and if I didn't try I'd eventually regret it.
[Obviously I can't say if it's gone well or not yet, but I've made it past the paralysis. Ask me again in 6 months if it was a good idea]
I would say a better test is if you are still having fun
Has anyone a better measurement for knowing when it is mediocrity and when it is perseverance?
 Funnily enough, both acquisitions freed up the respective founders to do bigger, better things: Evan Williams to Twitter, and Tom Preston-Werner to Github.
"If no new or current users/advertisers/customers/etc care about what you're doing, and no one in the company has a plan (or, more commonly I think, a desire) to fix it, you are probably in bad shape."
This sounds like a pretty high bar, but there are lots of startups in this position. Mine was when I folded it up - my cofounder had just left for business school, we'd been rejected by YC 3 times, we had basically no users, and I had run out of ideas for how to get users. I've met other founders in their mid-30s who've been working on their "startup" for the past 10 years, and are still in this position.
In contrast, Blogger and Gravatar both had thousands of happy users, and were growing, and had attracted the attention of some fairly important people (Dan Bricklin, anyone?) They weren't smash hits, but they were clearly on the right path in the dimension that matters - do people want what you make?
This is the hardest part about entrepreneurship and as Ben Horowitz puts it in one of his posts - no amount of pattern matching can help. These decisions can only be made from the gut - and basically need to align the entrepreneurs longer term motivations with 'his' understanding of the individual merits of the business.
They had a lot of users, and more importantly lots of people cared about the services. You can always tell if people care by the volume of complaints when the service fails.
I don't know enough about Gravatar to comment on that case sensibly.
It's not perfect, but this is somewhat a function of the person's knowledge of history and the current landscape of both competitors and technical tools.
This comment is somewhat ironic because I'm with Dropbox now. It really is a great company.
Tipjoy had to be shut down by its financial nature. Other sites can stay up on autopilot for a long time. Anyvite grew after its founders moved on, enough so that they recently came back and gave it more attention. Snipshot is one I think could enjoy a rebirth if they made it work on the iPad.
snipshot guys are at facebook kicking ass -- also relevant here I guess
> The reason mediocrity sucks more than failure is very simple: Failure lets you move on, mediocrity stalls you and keeps you from reaching your potential.
If Drew had carried on working on the test prep idea, it would have probably grown into something bigger within the broader education market, which seems to be popular with a lot of startups now.
To achieve huge success with Accolade, the product would have to expand out into new areas, unlike Dropbox, where the basic product itself caters to a huge market.
The rest have an incessant daily struggle to pay the rent and staff wages.
Also it's like quitting your present job for a possibly better opportunity. If you had the opportunity to gamble a small business for the opportunity of an explosive startup, would you do it? Should u do it?
Most importantly though, I was not sure how big of an opportunity it was
The market for SAT preparation is limited to students sitting for SAT in a given year in the US. The market for Dropbox is everyone with a computer and internet. Yes, the online storage market is super-competitive, but when it's that big it increases the likelyhood that chasing it is worthwhile.
It's not out of context at all. I'm not misleading anyone with my comment, or putting words into the OP's mouth. My comment fairly represents what the OP said about the competitiveness of the SAT prep market.
My intent was to indicate that the online storage market is also highly competitive. It wasn't to present a point by point analysis of the full post.
Differentiating and all of that don't matter a whit if there's no business to be had, but yes, you're right, it's hard to compete in a crowded marketplace. The thrust of the quote was more specific than that, though.
I think the worst startup founders are the ones who go from one idea to the next without really thinking about what went wrong or what they need to do differently in order to improve their chances of winning. They think mere repetition is going to make them lucky.
Conversely, I think the best startup founders are the ones who are persevering and determined enough to not stop taking chances, but they're also continually investing more time in training and improving themselves to get an edge. Failure for them is a great learning experience. Max Levchin had four failed ventures before PayPal.
You won't often find these types of posts from people or about people who aren't wildly successful already.
Chris Dixon had thoughts on this in an earlier posting:
The goal now is to continue to work towards the best idea. The original idea got us here, now we need to keep growing it and pursing it - not get comfortable where we are. It's important to put goals to see where we'll be a year from now to take the company from here to great.
Web design is service based, so your profits and costs increase linearly.
OTOH, a single piece of software can be sold multiple times, so the profits don't have the same relationship to costs.
I don't think that makes your business mediocre - just a different kind of business.
I'm a fan of building profitable, sustainable startups. I don't consider that to be mediocre at all.
(Preface: Coder at a major financial company, first job out of university)
That stings me because my current job is exactly what you describe but without much personal development OR software development. I often wonder how much harm it will do as a career move to just outright quit(I've been having trouble getting another job lined up) so I can get better at my craft and get a better position elsewhere.
Leaving there was the best decision I've ever made. I activated my professional network and had another job lined up in under 24 hours. Now, this job is about as meaningful, and I will leave it at the end of my year-long contract... but it's been a good change of pace, it doubled my pay, and I got to move to a new city and meet new people.
I'd encourage you to take the plunge. It's easier if you have a professional network in place, but even if you don't, unemployment is a powerful motivator. If you're single and you're not living paycheck to paycheck... do it.
I have a decent amount saved up with no dependents. Maybe I'll make the move sooner than later.
Also, I suggest listing to Dan Benjamin and Merlin Mann's Back to Work (http://5by5.tv/b2w). Best podcast ever for this sort of thing.
Just saying, your on the right track as long as you keep interviewing.
Otherwise, I am in the same situation as the grandparent comment, I've certainly lost more than I've learned at the present job. (But my CV looks better for what I planned to apply for next, which is the point.)
Its part of life. Realize that you've gotten too comfortable and get out of there.
The lowest risk way of doing that is to keep interviewing for jobs you want. This will force you back into learning what you need automagically.
I'm trying a new method - trying to start a company. You'll have to ask me in a year or two whether this is as good a solution :) ...
There are so many languages and frameworks and design patterns and whatnot that it'd be surprising if you WEREN'T constantly running into stuff you haven't used before. Don't underestimate your abilities to pick up new stuff.
That said, if you're dissatisfied, better to take a risk sooner rather than later.
I've quit every job I've ever had. Six were without written notice, though they were prefaced with talks with managers over several months indicating that I wasn't happy and why -- so I don't think in any situation it ever came as a surprise. In no instance did I ever have another job lined up. This is because I knew exactly what I wanted in a change, so I was ready to act on it.
Reading further down in the thread, it seems that you're not working on things you like. Tell a manager this, tell them what you'd like to work on, and see if there's opportunity within the company to do that, or if they're willing to make that happen.
Your feeling of "atrophy" seems to be that you're falling behind current trends. This happens in most organizations. Don't let anyone - even here - tell you otherwise. Places working with newer technologies that are better tailored to specific needs are in the minority due to politics, shortsightedness and a myriad of other reasons. The only way around this is to find these organizations that are absolutely exceptions -- The places that want to always use the best tool for the job, even if they have to spend the time to evaluate the new tools and learn it up front. Cardboard Box Co., BigOl Wholesaler Inc., or J. Random Fund-of-Funds are rarely those kinds of organizations. Why? No one wants to put their neck on the line politically in case they made a mistake. People are too busy looking out for themselves rather than the organization as a whole.
You will probably need to change jobs, but see if the current employer is willing to make things work for you. If no, it's a matter of when. I'd say at least come up with a big list of places you're going to apply to if you're going to quit. And if you've come up with the list, start applying.
Unless you want something else. Regardless, you're not going to act until you know what you want. So figure that out, and then you'll find you make progress rather quickly.
For you, sure. What about someone with two kids?
That said? Yeah, you do right by your kids, and you stay in that shit job, and you give them as much stability as possible.
A less persistent set of founders may have closed up shop and simply said, "Great technology, but the business around search just isn't there outside the context of a portal".
Google incorporated in late 1998, and by 2000 were powering the search results for Yahoo (the biggest website on the internet at the time). They were being paid (and paid well) for that too.
It was the same year (2000) that they implemented search advertising.
Given it only took them 12-18 months (of explosive growth) before they were powering the biggest site on the internet and making money I thnk it's hard to argue they were ever mediovre.
So there was a period of time they viewed the company as a mediocre investment. And at this point they were just Ramen profitable. But they powered through it, and legend has it, that it was one of the Yahoo co-founders that helped convince them to really make a run of it.
My point, what others may look at and call "mediocrity" and say they won't pay $750k for today, may end up in a few years being the fastest growing company in the history of the world.
Check out what these guys did, and follow the link to their product: http://siegetoys.com/post/4743188690/con-que-con-lasers-or-h...