John Cook over at TechFlash was nice enough to ask me to do a guest post on bootstrapping. This one is on how much runway you need to get your business over the hump.

“The single biggest enemy of an indeterminate amount of time needed for success is a deadline. And nothing gives you a deadline [...]

I wrote three posts over the past while:

A new definition of “lifestyle business”.
The reality of your life as a founder once you take VC
Your odds of making money if you take VC

Thanks to Rajat for pointing me to this video of DHH giving a talk last year. It’s not that I didn’t know the guys [...]

The fantasy goes something like this:

come up with an idea
take venture money
align with the VCs to grow the business as best you can with the firm target of an exit
hold on to enough equity so that when the exit comes you and the VCs both get rich
maybe some of your employees hang on to enough [...]

…albeit I haven’t said it nearly as well as well as Georges van Hoegaerden over at Venture Company.
I’ve been saying, by the time many venture funded startups have gone through their rounds of funding, even the founders are lucky to make any money. And that’s in the rare case that they actually make it to [...]

Conan was interviewed in the New York Times about his shift to the Tonight show. The following quote is about entertainment, but I think it applies to any creative endeavor, or possibly, any human interaction:
“In entertainment, you have to stake out what you think is right, you have to put out that signal, make sure [...]

One of my favorite things about working at Jackson Fish Market is that we don’t have performance reviews. I suppose it’s easy cause there are three of us and we’re all founder/owners of the company. But i believe that even once we do have more traditional employees we won’t have performance reviews. Mainly because [...]

The popular and prolific Malcolm Gladwell writes about underdogs in the New Yorker:

“What happened, Arreguín-Toft wondered, when the underdogs likewise acknowledged their weakness and chose an unconventional strategy? He went back and re-analyzed his data. In those cases, David’s winning percentage went from 28.5 to 63.6. When underdogs choose not to play by Goliath’s rules, [...]

Lifehacker linked to an article on the top workplaces in Australia:
“A recent poll in Australian business magazine BRW set out to find the 50 best workplaces, and while the results are Australia-specific, one thing stood out: Companies with great perks consistently topped the list.”
When you’re a part of the tech startup community it’s commonplace to [...]

So funny. I saw this blog post titled:
“Who Cares About Majority Ownership Anyway?”

We’ve always insisted on strict control of our business which is why we constitute a majority of ownership of our company - roughly 100% majority. However, I don’t think our way is the only way.
I thought the gist of the article would be [...]

David Heinemeier Hansson over at 37 Signals re-picks up the torch for people annoyed with the term “lifestyle business”. Their original post was back in 2005. Our twitter-sized definition was posted last month. Some goodness from the latest post:

“When the lifestyle card is pulled from its tired deck, it’s usually meant as a pat [...]

Red Gate, a software company, has issued a challenge looking for small (or “micro”) ISVs to purchase. I think that’s great. If we had a bunch of cash lying around we’d probably buy some cool tiny software enterprises as well.
That said, I did catch this little nugget in their announcement. Among the criteria of what [...]

In many ways, our aspirations for Jackson Fish Market are modeled after Pixar. Pixar isn’t the biggest in its industry, but it is among the best. It stays focused, it tries to do what it knows best, it worries primarily about creating something loved by its creators (as opposed to its demographic). Pixar also slowly [...]

Our little firm was founded with a healthy dose of engineering and design DNA. And it’s not as simple as pairing up an engineer and a designer. Walter loves creating beautiful usable things, and Jenny loves the power of software. We have shared values around a balance between tech and design, and we try to [...]

There is a simple lesson that all conferences should learn from TED. It’s not to charge thousands of dollars. It’s not to bring celebrities to your conference. And it’s not to only have one speaker at a time. Those may or may not be good things to emulate, but they’re not the most important lesson [...]

The way the term “lifestyle business” is bandied about has bothered me for some time. I’ve decided to try and come up with a new definition. Twitter friendly version:
“Lifestyle business” is the patronizing term for businesses unwilling to grow at the expense of the quality of their product or workplace.

Twitter unfriendly version:
“Lifestyle business” is the [...]

Paul Graham publishes a series of essays, and i often find myself agreeing with them or inspired by them. His latest talks about the characteristics he thinks startup founders must have.
“I was writing a talk for investors, and I had to explain what to look for in founders. What would someone who was the [...]

What is it about some big companies that once they get successful, they immediately forget how they got there (innovating, meeting customer needs, moving quickly), and start engaging in all sorts of brand-suicidal tactics that usually involve lawyers.
This TechCrunch post shows correspondence from Intuit to Mint (and back) with Intuit lawyers basically calling Mint liars [...]

A few months ago we wrote about (and were quoted in) an article in AdAge lamented the lack of support for branded apps (and widgets) from big advertisers. Here at JFM we have always believed that brand sponsors, looking for engagement, will ultimately realize that software is the single most cost-effective way to engage users [...]

There’ve been countless posts on how trying to make something perfect usually ends up not only with nothing perfect, but often with nothing at all. In my limited experience, this “common sense” is not so common. I love when this precept is illustrated so plainly:
“The ceramics teacher announced on opening day that he was dividing [...]

I caught this article in Slate, and thought it was a good wake-up-call for anyone starting their own small business — especially in industries that are oft-romanticized. Like, say, cozy cafe’s or consumer tech startups.
“The dream of running a small cafe has nothing to do with the excitement of entrepreneurship or the joys of [...]

We’ve already shared our thoughts on what bootstrapping means, but when I read this piece on bootstrapping I couldn’t help but share since I think it’s pretty much on:
“When you decide to bootstrap, you commit to fund primary development and growth through internal cash flow from real-life customers. You — the founder — and a [...]

I was having a discussion the other day with a friend about old media transitioning to the new world — a process that the current economic situation will (i believe) hasten. I have long believed that the main thing hampering newspapers, record labels, etc. is their premise that when the transition is complete they need [...]

I really have no clue what’s going to happen with the economy. I read all the same reports that everyone else does. And I do have this sense that human beings are really good at predicting that things will be kind of similar to the way they were in the past. (Which means of course, [...]

I’m not entirely sure that I’m qualified to comment on this issue as I run neither marathons nor sprints, and while our little startup here is progressing nicely, I wouldn’t claim we’re (yet) something to model your business after. That said, I feel the need to comment anyway. (Big surprise.)
Jason Calacanis sent out e-mail with [...]

In November we will reach the our second anniversary as an official business. (We didn’t get really going until the following spring when Jenny and Walter arrived.) It’s kind of interesting, when you’re starting a new business there’s a literal ton of information on the web, at bookstores, etc. to help you. And yet, there [...]

I know that many people have complained about the Seinfeld/Gates ads, but I liked them. In fact, I would watch a sitcom every week starring Jerry and Bill. I think it’s funny. But i really like Seinfeld and I really like Bill. So I suppose I’m biased. Also, there’s a third ad I believe which [...]

Here’s the thing: I wouldn’t have written the post that John Casasanta at taptaptap wrote about the VCs that are approaching him, but as Chris Rock would say — I understand.
A sample from John’s post:
“The vultures are out and and they taste blood. The iPhone’s one of the hottest things around right now and there’s [...]

From dictionary.com:
boot·strap, noun, adjective, verb, -strapped, -strap·ping.

–noun
a loop of leather or cloth sewn at the top rear, or sometimes on each side, of a boot to facilitate pulling it on.
a means of advancing oneself or accomplishing something: He used his business experience as a bootstrap to win voters.
–adjective
relying entirely on one’s efforts and resources: The [...]

Noam Wasserman on his Founder Frustrations blog does great analyses (like this one) of startup founders and how they fare in different startup exit scenarios. It’s interesting to see the reality.
I’d love to see a study that compares venture funded tech startups to bootstrapped tech startups. Specifically I’m interested in:

What are the relative success rates? [...]

“Who believes a brand’s elaborate web of often conflicting messages, when ten thousand connected consumers agree that the company behind the brand sucks?” (PDF)