Venture Capital’s Biggest Fear

March 1st, 2011

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.

Must Be Nice

February 25th, 2011

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.

MarsEdit 3.1.7

February 24th, 2011

MarsEdit 3.1.7 is now available for direct download and from the Mac App Store.

This release fixes a bunch of annoying little quirks, and some rare crashers:

MarsEdit 3.1.7

  • Restore ability to collapse libraries section in Media Manager
  • No longer beeps when attempting to save an already-saved local draft
  • Improvements to further reduce RAM memory usage
  • Fix an issue where media manager folders were not auto-refreshing content
  • Fix the displayed items count in Flickr and Published media sections
  • Fix to support detection of rel=”shortcut icon” style favicons
  • Fix occasional crashes while reloading media items
  • Fix non-image files were inserted into post with image markup
  • Fix crash when attempting to add enclosure without URL
  • Fix possible blanked content when opening a post in external editor
  • Fix crash when inserting Technorati Tags in extended area in rich mode

What Is Blogging?

February 23rd, 2011

In response to my comment on Twitter about wanting to commission a good entry-level web site for aspiring bloggers, Ian Beck experiments with nailing down exactly what blogging is. Obviously, it’s many, many, things. Like chess, you can teach the ground rules to somebody, who then has a practically limitless number of choices about how they deploy with those rules.

Some of Ian’s remarks are inspiring, and may encourage you to blog more even if you already know what blogging is. I particularly like the simplicity of:

Blogging is sharing something you have created online. And then doing it again tomorrow (or next week, or next month, or next year). And again.