For several months now, Tumblr has apparently been a victim of its own success. What used to be known as a super-popular, well-designed, streamlined blogging service with lots of internet-famous blogs hosted on it, is increasingly known as all that and also as a flakey, unreliable service. Folks who host their blogs on Tumblr are up-in-arms about the frustrating error-proneness and downtime of the service.

My primary product, MarsEdit, is a desktop blogging client that interfaces with Tumblr, among dozens of other types of blogs. The reduced reliability of Tumblr, and in particular of its API, has meant a deeply compromised experience for our customers in common. This means that I also suffer some pain in the midst of Tumblr’s flakiness, because I have to support an unreliable service and explain to customers that MarsEdit is affected by Tumblr downtimes as well.

Some of Tumblr’s greatest assets are the deeply respected bloggers who trust Tumblr to host their writing. They serve as implicit spokespeople for the service each time they publish an entry, and more explicitly so when participating in Tumblr’s own social network, raving about the site on Twitter, at conferences, etc.

As flakiness continues, the tone of endorsements is turning negative. I regularly see sarcastic snipes against the service in my Twitter feed, and even on blogs that are hosted by Tumblr itself. Garrett Murray’s frustration peaked yesterday when he posted a sarcastic revision to Tumblr’s increasingly famous “downtime” graphic. Steven Frank of Panic fame chimed in today on Twitter:

It occurs to me that Tumblr is also growing exponentially with no apparent income source. I should look for a new home, pre-dickbar.

Tumblr has a problem. Since late 2010 and for all of 2011 they have been suffering enough downtime and flakiness that a growing chorus of users is lambasting the service. Without judging whether that’s fair or justified, let’s accept that what used to be a widely lauded service is becoming a widely criticized one.

But how big of a problem is it if, as Steven Frank suggested in his tweet, the service continues to grow its membership by leaps and bounds? My theory is Tumblr’s continued success in signing up new customers is both thanks to and at the expense of their influential early adopters. Folks who helped to build Tumblr’s reputation over the past several years are now suffering, presumably because of Tumblr’s ravenous ingestion of new users. If this keeps up, the influential “power-bloggers” will quit Tumblr and move on to more reliable services. Tumblr will be left with millions of users, who I’m sure are perfectly nice people, but who don’t exert as great an influence in the web world.

What should Tumblr do? If the failure to rein in performance and uptime issues is connected to success in signing up new customers, then they should stop signing up new customers. Sound foolish? In Tumblr’s position I would do whatever it takes to bring back the level of service that users enjoyed before the “great downtime of 2010.” Happy, influential customers paved the way for Tumblr’s success, and bringing back that enthusiasm is the best way to perpetuate success far into the future.

If Tumblr turned off new user registrations today and added a “notify me when more new users are being accepted” sign-up form, it would provide breathing room to focus on fixing the experience for current customers. Framed correctly, it would also make those customers feel cared for and important, something they probably aren’t feeling so much at the moment. Yes, for prospective customers it would be a slap in the face. Nobody wants to feel shut out. But if given a choice, protect your existing, not future customers. Web services build buzz all the time with limited, invitation-only beta testing intros. It would be a step backwards for Tumblr, but it would also re-establish a sense of exclusivity that would pay dividends after issues are resolved and open enrollment returns.

It’s easy to armchair-quarterback another business when you don’t know any of the details. I’m sure the challenges at Tumblr are diverse and hard to pin down to my convenient diagnosis of “too many users.” But if you’re bailing out a sinking boat, the first thing to do is stop admitting new passengers.

I hope Tumblr figures out a way to solve this for the long run. My customers depend on it. Their customers depend on it. And the longevity of the company itself depends on it.

Some of my Twitter friends are buzzing about Alex Payne’s arguments on what constitutes a respectable entrepreneurial pursuit. In case you want to catch up on the pre-reading, it starts with a post by Justin Vincent, basically promoting the idea that indie “mom-n-pop” businesses are a reasonable alternative to massive, venture-funded pursuits. Payne responded with a snarky comment, provoking a heartfelt defense from Amy Hoy. Finally, Payne posted a retraction and clarification, the nut of which was set in bold for emphasis by Payne himself:

We should endeavor to improve the lives of as many people as possible in a lasting and significant way, making the most of our own skills in the process.

Should we aim to affect as many people as possible? My heroes have tended to please themselves first, and to please everybody else by accident. When Steve Wozniak set out to invent the Apple personal computer, he did it for himself, and perhaps to show off for a few nerdy friends at the computer club. Noam Chomsky wrote generally about languages and grammars, and was allegedly annoyed when his research happened to lay the groundwork for major fields of computer science. I doubt many of history’s great advancements happened according to the plan of the geniuses who were responsible for them.

As a self-employed business owner, I want to improve the lives of my customers. And, yes, I would like to have a lot of customers. But Payne’s measure of success is too lofty. Rather than aim incompetently and uncertainly for a massive impact, I focus on a small area that I understand and that I care deeply about. I please a small subset of all people, but I please them greatly. Focusing on what I know and appreciate is the balance that keeps me self-funded, intellectually stimulated, and productive. Who knows, maybe I’ll turn out to be an accidental genius, as well.

Ambition to influence or change the world is, on its own, relatively useless. Pursuit of truth and understanding, on one’s own terms, is the noblest of endeavors. If you’ve found something you can work on all day for weeks, months, or years, don’t let anybody tell you it’s not worth doing.

I enjoy running my own business. One of the things I find most interesting is learning about business mechanics from a completely hands-on perspective. While I would not classify my education as nearly complete, in the several years I’ve run Red Sweater I have a learned a few objective truths about all businesses, and many subjective preferences about how my business should be run.

One of the most important questions any business deals with is how it will be funded. If you’re thinking of starting a business, you should probably decide how you want to be funded early on, so you can orient your business towards being successful in the context of that funding.

Broadly speaking, a business will either be “bootstrapped” or funded by outside investors.

The goal for a bootstrapped business is to come up with your initial funding, be it in the form of cash, free time, raw materials, or some combination, and parlay these resources into a service or product that generates revenue from customers. Once the revenue from customers pays for the founders’ initial investments and sustains the recurring expenses of the business, theoretically including your salary as a founder, the company is profitable and poised to grow. The huge benefit to bootstrapping your own business is that, once the company is profitable, you retain 100% control of the business’s strategy and resources.

Another method of starting a business is to seek outside investment in the form of angel funding or venture capital. You give up some clearly specified percentage of the company’s ownership in return for cash, guidance, and social connections. From here, the goals are basically the same: to become profitable, but at the end of the day you end up with a smaller stake in your own company than you would have if you bootstrapped it yourself.

I think there are good arguments for both approaches, but I am strongly disinclined to seek venture funding for my business. When friends ask for my opinion, I almost always strongly discourage them from seeking it as well. Why? Because venture capital doesn’t speak to our priorities, and is unlikely to build the kinds of companies we want to run.

I was listening to the always-inspiring This Week in Startups podcast when an interview with Tony Conrad led to a perfect synopsis of why venture capital is not right for me. Jason Calacanis and Tony Conrad were discussing the state of venture capital in the technology world, and observed that consumers are spending a ton of money online, but there is a “risk” that the money is being distributed among too many companies. In a nutshell, they said, the online business world was becoming more like “Main Street,” with too many small businesses, and not enough “Walmarts” to pay back the massive returns.

This, Tony Conrad said bluntly, was his “biggest fear.”

Venture capitalists would rather fund a single billion-dollar company than a thousand mom-and-pop million-dollar shops. I can’t say that I fault them for this, but it cuts to the core of where their priorities lie: they gamble on high stakes, massive returns, while shunning the concerns of any business that wants to maintain a mom-and-pop Main Street business ideology. Personally, I prefer the Main Street shopping aesthetic to Walmart, and I know which part of town I want my business in.

If you want to be Walmart, by all means seek venture funding: you’ll need lots of it to stand a chance at succeeding. If, on the other hand, you want to build a company guaranteed to preserve your values, fund it yourself and maintain control. You’ll own something to be truly proud of while helping to scare the crap out of venture capitalists.

I just read a piece by Mike Monteiro of Mule Design, mostly about choosing clients who you can stand behind, but hinging on an anecdote about interviewing a prospective employee:

I asked him if he agreed with how they made their money. He replied in the negative — he’d just done the design. I told him we didn’t take on any projects that we couldn’t ethically stand behind.

And here I’ll quote him: “Must be nice.”

And that’s when I decided not to hire him.

Almost 15 years ago I was working my ass off at Apple as a junior engineer in the System 7 software updates team. I was trying to make a reputation in my new career, but also doing my part to make sure we shipped on time. In a historical sense, most what we built is hard to get excited about these days, but we were doing the exact same thing that Apple does today: iterating to give our faithful customers a reason to stay faithful.

In a group that was primarily oriented around fixing bugs, my colleagues and I were especially susceptible to a problem that plagues many developers: once you’re on the tail of a bug it can be hard to stop hunting until the issue is resolved. Some days we worked short hours. A hard-won victory at 4PM might be grounds for calling it an early day. But other times, stumbling onto a glimmer of hope with an impossible bug that “had to be fixed by next week” was cause for camping out until the wee hours of the morning.

One of these marathon bug-hunting sessions had a coworker and myself working until 2 in the morning, bleary eyed, but desperate for a solution. Usually I would recommend rest and resumption when it comes to this point, but we felt sure we were on the verge, and this was an important, difficult bug. We had a breakthrough, and spent another couple hours verifying a fix, testing it, and checking in the code. We went home exhausted but jubilant.

I collapsed at 5AM and slept until 11, conscious that the bug-busting marathon was not over. My boss, my boss’s boss, and for all I know, his boss’s boss were all aware of what we had done. It was a significant win for the team, but there was plenty more to do.

When I got into work after noon, my colleague was already there. He was talking, in the common area of our floor, with a humorless, long-time employee who worked in an administrative role with our team.

“Where have you been?” she asked contemptuously. “We need to ask you about the blah blah blah.” I’ve forgotten the specifics.

“Sorry, I was here late last night and only got in a few minutes ago,” I said.

“Must be nice,” she answered tersely. Her words stung. I was young, trying to prove myself, and had just returned to the fray after helping with an important victory. She had left at 5PM the previous night and had a long, restful night’s sleep. Or at least, that’s what I assumed she did.

What irked me most about her “must be nice” comment was how profoundly void of empathy it seemed to me. I hated her for years because of this. In part because of her, I have since been extremely sensitive to these pithy, jealous expressions: they jump out like smarmy little diamonds. But when words like these occasionally get lobbed at me, I am not nearly as hurt as I once was. I tap into my own empathy reserves, imagine what a crappy life they me struggling with, and try to wish the best for them.

It’s not so nice to be a person who says must be nice.