Someone posted an interesting “Ask YC”, asking:

“How to start becoming an entrepreneur while still being an employee?”

Having done this twice (started a company that eventually turned into a full-time startup), I settled in to reply. Before long, it was clear that my response was long enough to justify a blog post.

I’ve done two part-time-to-full-time startups (one resulted in a startup the sold, the second is RescueTime– currently a YC-funded company– cross your fingers).

At the end of the day, I think Paul Graham is right when he says:

“The number one thing not to do is other things. If you find yourself saying a sentence that ends with “but we’re going to keep working on the startup,” you are in big trouble. Bob’s going to grad school, but we’re going to keep working on the startup. We’re moving back to Minnesota, but we’re going to keep working on the startup. We’re taking on some consulting projects, but we’re going to keep working on the startup. You may as well just translate these to “we’re giving up on the startup, but we’re not willing to admit that to ourselves,” because that’s what it means most of the time. A startup is so hard that working on it can’t be preceded by “but.”"

In the beginning, however, it’s not always practical to dive in full-time. And sometimes when your idea is off-the-wall and also easy to build a prototype for, it’s smart to whip something out just to see if what you’re building is as cool as you think it might be before you take the plunge.

So if you’re too poor or too unsure to do the right thing for your business and dive in full-time, here are a few things that seemed to work for us when we did it part-time:

1. You need a co-founder and some cheerleaders… If you can’t find 2-3 friends who are really excited to be beta testers for what you’re building, ponder changing your direction. The arguments for a co-founder are many and varied. For a part-time effort, they are essential to keep you on-track and working. At some point, you’ll hit a motivation wall… If you have a partner who is depending on you, you find a way past that. If you don’t, you’ll often lose interest and find something else to entertain you.
2. Pick a day or two per week where you ALWAYS work, ideally in the same room as your co-founder(s). ALWAYS, no exceptions. We did 1 weekday evening and 1 weekend day. That doesn’t mean we weren’t working other days, but having a fixed schedule helps you through the phases of the project that might not be so fun.
3. Have a boat-burning target. What will it take for everyone to dive in full-time? 5,000 active users? 10,000 uniques a week? Funding? That should be a shared understanding. You don’t want to have one founder ready to go full-time when another has reservations. This is easy to gloss over, but you should really nail it down. I’ve lost 2 co-founders to this issue (they weren’t ready to dive in full time and I was). It wasn’t fair to them and it wasn’t fair to me.
4. Pick an idea that is tractable. Every business is a theory. If your theory is, “we can build a better web-based chat client”, that’s something you could test quickly. If you’re theory is “we can build a car that runs on lemonade”, that’s just not going to work as a part-time effort. The scarcity of available time should force you to distill the idea to the absolute essence that is necessary to test the theory. No extraneous features!
5. Understand that your v1 ia probably going to suck. Read David of Weebly’s post on persistence. It’s a long road. My first startup was a ridiculous fluke (2 months and then sold). 99% of the overnight successes you read about were slogging in the muck for 5 years before the night in question. Be prepared for a long journey and be surprised if your startup is an immediate hit. So with your v1, look for the tiny little flicker than you might be on to something to motivate you to make it better. Every week, make it better than last week and see if that flicker of light can be fanned into a tiny flame.
6. If you’re going to screw off at work (everyone does), spend it getting smarter about the stuff you don’t know. If you’re a coder, read a few design/usability blogs. Read up on what motivates angel investors. Research competitors and write down what they do well. Get brilliant at SEO (it’s not hard). Write a LOT more (blogging helps). Think about virality and research the heck out of it. This is all more valuable (and hopefully just as fun) as looking at LOLcats on Reddit. All that being said, be aware of the fuzzy line between using your cool-down time at work for your startup and stealing time/resources from your employer. If you’re paid to do a job, you need to do it.
7. [edit: Thanks to Ivan in the comments] Be sure you own your startup. I’ve had the fortune to work in places and companies where there was very clear ownership of “after hours” work. If ownership of your personal IP is not clear, do NOT rely on the good will of your employer. Greed can do funny things to people, even if they were initially big supporters of your startup.

At the end of the day, you want to prove whatever you need to prove as quickly as possible, so you can dive in full-time. Near as I can tell, there are plenty of startups that have started as “hobbies”, but you need to take it out of that phase as soon as you can. There is nothing that drives a team forward like the fear of public failure, debt, and starvation. Leap off the cliff and start building the airplane on the way down and you might be surprised with what you can pull off.

Big release for RescueTime today. I have no time to write about it (and probably oughta write on the RescueTime blog if I did have time… which I promise I’ll do).

If you’re a RescueTime user, check it out and let us know your thoughts!

Everyone with a fine liberal arts education should be familiar with Zeno’s Dichotomy Paradox (props to Steve Leroux for helping me remember his damn name).

“Suppose Homer wants to catch a stationary bus. Before he can get there, he must get halfway there. Before he can get halfway there, he must get a quarter of the way there. Before traveling a quarter, he must travel one-eighth; before an eighth, one-sixteenth; and so on.”

I can think of no better description of software development releases (or product development in general). At some point you have to say “fuck it”, fall forward, and confound Zeno. Throw caution to the wind and ship too early and you ship crap– and your users know it. Aim for perfection and days stretch to weeks as each day brings you asymptotically closer to greatness (which sucks the life out of any team, IMO). I know teams who literally have worked for a year or more without shipping anything to anyone. I don’t know how they can do it.

But, any way you slice it, those last few days before a release feel like you’re wading through rancid molasses.

There has been a lot of chatter lately about alternatives to Silicon Valley. There is no denying that Silicon Valley produces more startup success than any other town. But is it cause or effect? Does SV add some secret sauce to the startup recipe or is it simply a place where a lot of geeks tend to congregate?

For starters, it’s a good idea to read Glenn Kelman’s outstanding post on Seattle as a startup hub, inspired by the New York Times piece on the same topic. TechCrunch fairly quickly blew the post out of the water, causing Glenn to post a solid (and humble) response. And, causing Alan to point out that Arrington is “being a wanker”. Fun stuff! I I’m a big Arrington fan, but I’ll second the sentiment… It’s easy to crap on an upstart. Windows people have been doing it to Mac people for years. “You’re so far behind, why are you even trying? It’s almost pathetic,” they say. Strange that you don’t hear that too much anymore from the Windows camp. Never count out an upstart!

As a founder who is currently hip deep in the YCombinator experience in Silicon Valley, my initial inclination was to return to Seattle in March. I’m currently rethinking that sentiment (but haven’t made any sweeping decisions). The purpose of this post is to publicly run through some thoughts on this and get some feedback.

As mentioned by just about entire world, Silicon Valley births more startups than anyone. By a huge margin. It’s ridiculous how far it is ahead of upstarts like Boston, Seattle, Austin, etc. It’s obvious to me that there are many more startup PEOPLE in SV (which is a big reason for the number), but are there factors there that make startups more successful? I’m going to run through the thing I think are critical for a startup and how I think SV adds to them. Call me out if I’m wrong or if I’m missing anything:

• First and foremost, a startup needs to build something people want. I don’t think SV really helps here. In fact, the “echo chamber” effect might cause founders to thing that people around the world actually think and behave like the geeks in SV. If you buy the argument that SV people are smarter/better than other folks, then maybe SV would get an edge here.
• A startup needs a great team. People who destroy problems. People who prioritize the right problems. SV certainly has the edge here in supply, but it’s difficult to determine how the demand effects that availability of these people. I will say that, while I have been pretty damn impressed with the people in SV, I don’t think they are any better than the best people in Seattle (but there sure are a lot of ‘em). And they tend to be more motivated, more monomaniacal, and more mercenary. Again, it’s hard to gauge supply and demand here– there are plenty of startup nuts in Seattle. I’m tempted to give the edge here to Silicon Valley because that’s what people smarter than me have concluded in the past, but that seems like a lousy reason to do it. It comes down to this– if I spend 6 months trying to build a small kickass engineering team, would I get a better team in SV? Or is the competition too fierce?
• Startups need to work their asses off. This seems to be one of Arrington’s main points: That Seattle-folk frolic on hiking trails and in kayaks instead of working on their startup. I think that’s pretty ridiculous. Passion and dedication aren’t geographically bound. There are plenty of SV people who bounce from party to party and conference to conference when they should be coding or slinging pixels. This is a personal trait, though you could argue that SV attracts more monomaniacal folks. Again, however, there’s no denying SV has the edge in supply– but does the demand outstrip it? Does more = more who are available?
• Startups need money and time. And, oftentimes, money can buy you time. Here, Silicon Valley bitch-slaps any of the upstarts. Anecdotally, it seems that funding in SV happens quicker (allowing founders to get back to building products). It also seems more available for early-stage companies. For companies who can’t bootstrap their way to a 12-18 month runway, this is huge consideration. This is also a big deal for companies without an obvious revenue model (Twitter?).
• Startups need blog and press coverage. SV wins here, too– by a healthy margin. I’m tempted to break out my “marketing is a tax you pay for being unremarkable” quote (I wish I could recall who originally said this). I firmly believe that you’ll get coverage if you’ve made something exceptional that people really want. There’s no arguing, however, that that you’ll probably get more if you go to the right parties and conferences, and manage to chat with bloggers like Scoble or Arrington.
• Distribution and deals. Technologists can often be snarky about the idea of bizdev, but it can be damn powerful. At the end of the day, many of the people you want to be doing deals with are probably in the Valley, and deals happen better if you can meet face to face ( and meet often, if necessary). There’s something inherently more comfortable about doing a deal with a company down the street. SV wins here, hands down.
• Lawyers and accountants. SV has more specialized services folks, but I’ve literally never heard of a startup who died from lack of a great startup lawyer. I think there is a healthy supply of these in any of the upstart hubs. Am I being naive here?
• People who buy startups. Acquisitions are like any other deal. They oftentimes happen because of face-to-face meetings and are probably likelier to happen if you are right down the street from your potential suitor. Seattle has Microsoft and Amazon. SV has just about everyone else who buys startups, notably Google and the ailing Yahoo(soft). Your mileage will vary, depending on your startup. A financial software startup might have a better chance of getting bought in NYC.

It’s probably safe to say that each of the above points carry different weights for different startups. A company like mine might not care much about great startup lawyers, but a company like Avvo might. A company like Twitter clearly cares an awful lot about funding– it’s a big play with a ton of upfront expenses and no immediate way to make a pile of money. But for a company like mine (which, ultimately, is probably going to live or die based on the value we can provide to businesses), will living in Silicon Valley give us enough of an edge to justify the expense and distraction of moving?

I just posted what I thought was a pretty darn interesting post about Google’s dominance in my life. By my count (and, with RescueTime, my count is pretty damn accurate), 13% of the time I spend in front of my computer is taken up by Google products.

Note that this is COMPUTER time– not just my online time.

Check out the post!

I don’t imagine too many people who read this blog would be terribly interested in this, but I have to crow about it anyway. Joe (cofounder and roomie) and I figured that the move to Silicon Valley was an ideal time to adjust our diet and shave off a few pounds.

Since arriving (Jan 4), I’ve lost just over 9 pounds or (as I like to think of it) 36 sticks of butter. This is all with only nominal excercise and eating just about as much as I want. Joe (always the showoff) has lost 15 pounds.

If anyone cares, this was done with a “lazy” South Beach diet. Lots of veggies, plenty of lean meat/fish, and functionally zero sugar/simple carbs.

Joe, Brian and I have arrived in Silicon Valley unscathed, despite the monsterous storm blanketing the region. The trip was rainy, but thankfully the snow was fairly painless except for about a 10 mile stretch at the Oregon border.

We’ve settled into our furnished apartment and have shuffled it around to be dramatically more office-centric.

Not a lot of people know this, but RescueTime was built in a part-time way– generally evenings and some weekends from time to time, on top of day jobs and/or consulting gigs. It’s a testement to technologies like Ruby on Rails and MySQL that we could pull this off. I am incredibly excited to see what we can pull off now that we’re working full-time on this thing with zero distractions. The good news is that we’ve literally had thousands of feedback emails from our users– so we’ve got a pretty good sense of where to go.

Stay Tuned!

Been a while since I’ve posted. I’ve been absolutely slammed and had a few scheduled trips smack dab in the middle of some of the busiest work time I’ve ever experienced.

Today I’m organizing a batch of pictures for a Flickr upload session and found a gem from Halloween. I was attending a Murder Mystery Dinner (something I was fairly skeptical about, but we had a great time!)– Alex was an insane dentist and I was the “Prince of Dimness” (the Prince of Darknesses dim-witted little brother).

I’ve posted a lot more detail and accompanying thoughts over at the RescueTime blog… To summarize:

• RescueTime has been funded by YCombinator, one of the most prestigious seed-funding outfits that’s out there (in geek circles, anyways). If you aren’t familiar with it, here’s a bit of info. YC was founded by Paul Graham (startup guy, writer, and crazed Lisp advocate) and have been funding very-very-early-stage startups for just a few years. Since they spun up, they’ve funded dozens of great companies including Xobni, Loopt, Reddit, Justin.TV, Scribd, TextPayMe and more (scroll down for a list).
• Part of the YC program is that the founders must relocate to Silicon Valley for a period of 3 months (starting Jan 08). During the three months, there are weekly dinners with assorted Valley luminaries. At the end of the three months is Demo day (now, by popular demand, spread to 2 Demo days), where you pitch what you’ve built to a big room full of early-stage investors.
• The financial part of the funding is such that we’re still effectively bootstrapping. So please don’t call trying to sell me expensive services of any kind.
• We just got coverage on TechCrunch. Neat!

I can’t express how excited I am about the opportunity. RescueTime started as a hobby project to “scratch an itch” that we had. With incredible enthusiasm from our users and a handful of advisers, we’ve been happily dragged into taking RescueTime to the next level.

I’ve been running WordPress for this blog since the beginning. It’s a great platform. I’ve officially been drinking the Kool-Aid. I tell my friends about it. I heard Matt Mullenweg speak (at SXSW last year) and I rave about that.

So when it made sense for us to spin up a little blog for RescueTime (my fledgeling time management software business), Wordpress got the nod. Rather than host another WordPress blog, I opted for a hosted WordPress account. WordPress offers barebones options for free, but I opted for a few premium options, making me a paying supporter of WordPress. It felt good.

The other day, I got an email from a few strangers telling me that the PowerPoint deck I had posted on my most recent blog entry (“DIY Web Marketing: 16 Resources for SEO, Social Media Marketing, & Viral Marketing”) was a dead link. It HAD been working (I know several people who downloaded it). No big deal, I thought. Tech glitches happen. As a guy who runs a SaaS biz, I’m quick to forgive on such things. It was inconvenient timing though– I’d just had a speaking engagement at Seattle Tech Startups and the PowerPoint deck in question was my deck for the presentation (I’d promised at the end to make it available– which is why I was getting peppered with emails).

My first step was to log in to see if I could fix it myself. No go. In fact, I couldn’t even log in. It told me my account was suspended.

I dutifully researched their message board (I know how expensive support is, so I figured I’d try to help myself) and found that random/accidental suspension issues were occuring as a result of a recent bug. Ahhh– that made me feel a bit better. When I finally got an email response, I was dismayed.

Your blog was suspended because it violated our ToS.
Basically, we don’t allow blogs created solely for commercial purpose,
or for Search Engine Optimization purpose.
I’ve temporary unsuspended your blog, so that you have a chance to review our ToS,
and clean it up a little bit…

www.wordpress.com/tos

Trying to keep my cool, I replied:

What?

It’s a blog about a tiny web service with 8 or so posts (so far). It doesn’t have any advertisements or any revenue generation capability whatsoever. I mentioned SEO in my last post because I did a little presentation at SeattleTechStartups.com a few weeks back– but RescueTime (http://www.rescuetime.com) has nothing to do with SEO (and, at present, isn’t even remotely a commercial enterprise). I reviewed to ToS fairly carefully and see no violations.

Are you SURE it was purposefully suspended? I’ve read several threads (covering the last few days) that seem to indicate there is a bug going around:

http://en.forums.wordpress.com/topic.php?id=16792&page&replies=5

http://en.forums.wordpress.com/topic.php?id=16787&page&replies=10

It seems a heckuva lot more logical to me that I’m a victim of this bug… I assume that if someone shuts down a blog for a breach of ToS that it would have some sort of note attached to it (to discriminate it from a bugged account)?

Several days have passed with no response. I have no idea if my blog is temporarily not suspended, if it was a bug, or if there truly was a breach that I’m not aware of. The blog is a simple product blog (I know a lot of startup guys who have such a thing– presumably that doesn’t count as “commercial purpose”?). I understand that suspending blogs is something WordPress has to do to be vigilant in the fight against spam, but would an automated notification hurt, citing the ToS clause in question? Given that I was actually a paying customer (not just freeloading off of their free offerings), would it kill ‘em to respond to my last email?

For the record, the blog gets VERY little traffic (thousands of uniques a month is all).

WordPress will continue to be my blog platform of choice– I’m too darn used to their fabulous interface. But (if nothing changes) I won’t be spending money with them again and I certainly won’t be recommending them as I have in the past. As they say, “customer service is the new marketing“.