In Paul Graham’s classic essay “How Not to Die”, PG described success at a startup like this:

If you can just avoid dying, you get rich. That sounds like a joke, but it’s actually a pretty good description of what happens in a typical startup. It certainly describes what happened in Viaweb (the startup he sold to Yahoo!). We avoided dying till we got rich.

This “figure out how to survive and you will succeed” concept is phenomenal advice - simple yet powerful - and the entire post is worth reading. However, there’s a problem. I talk to founders/potential founders all the time who have internalized the “just keep swimming” mantra and I have realized they largely don’t understand what “surviving” means. In most situations, survival has less to do with the stubborn perseverance most people seem to automatically associate with “not dying” and more to do with the brutal destruction of bad...

Scaling hurts. For the first time in my life, I’m scaling a startup with significant hype from funding/launch to prodictable, measurable growth. The only way to do this is with a killer team, and with building a killer team comes hard questions about compensation and equity. I’ve believed for a long time that everyone at an early stage company shouldn’t just get equity - they should get a LOT of equity. I think it’s good for the company because I believe people with significant equity do dramatically better work. However, in all discussions about equity for new hires the question has to be asked: what makes you so sure that people with more equity do better work. As I was pondering an answer to this question yesterday, the perfect example of why you should give engineers more equity played out right in front of me.

Before founding Knox, I helped start Coffitivity.com, a popular ambient...

Today, Jessica Livingston and Y-Combinator announced the Female Founders Conference, a conference designed to help female founders be better prepared to build successful startups. This is is presumably somewhat a response to some of the bad press (misleading though it may have been) Paul Graham recently got in response to some statements he made about female hackers, although I would not be surprised if this is something Jessica and Paul have considered doing for a while now.

Predictably, people on Hacker News immediately started in on the same argument one hears every single time a “women only” event is introduced. “This is gender discrimination,” they say, “if we had a Male Founders Conference, would THAT be acceptable?” The presumption is of course, that the male version of the “Female Founders Conference” would be the “Male Founders Conference” - a conference focused on improving...

The easiest way to raise your next round of funding is to start it out with money from your existing investors. This is why in almost every Techcrunch Series B funding announcement you see “participation from existing investors” somewhere in the article, unless the original investors were priced out of the round. There are several reasons for this: existing investors already believe in the product, if things are going well they want to protect their past investment from not receiving funding for poor reasons, and they are able to ensure the new funding doesn’t do anything to screw over their previous investments. As a founder, this means the ideal composition of a new round of financing consists existing investors + new strategic partners. But what if you’re not raising a Series B - what if you’re raising you’re first seed funding? How do you get the magic that is “existing investors”...

The Anatomy of Frank is the best band in the world right now.

“But Tommy - you haven’t HEARD all of the bands in the world, how can you say that so confidently?”

Well you’re right friendly reader - I have not heard all of the bands in the world, so I can not be 100% sure that the Anatomy of Frank are the best band in the world. However, do me a favor: go here and listen to Blurry Part II through Blurry Part III with headphones on. Give it the full 11 minutes it deserves. If you prefer something more update, listen to Bill Murray through Hey SATAN! Your choice.

Now tell me: do they deserve to be in the conversation? Yes, the do. They are incredible. Further, my usual go-to choices for “best band in the world”, Radiohead and Arcade Fire, have both been making the worst music of their careers lately. FURTHER - I have heard a few of the tracks that will be on the Anatomy of Frank’s new...

For all the talk that 2013 was a disappointing year in tech, I tend to agree with Om Malik and Paul Singh: some big, big things happened in 2013, they just weren’t obvious. After years of observing the payments space and spending the last few months working in it directly, it’s become clear to me that 2014 is going to be the year that the payments revolution finally arrives.

We’ve been waiting for a true revolution in payments for a long time now. I would argue that payments have followed the Hype Cycle almost perfectly: an early recognition that the Internet would change things, some early productivity (PayPal), a ton of hype that wasn’t realized (NFC, mobile payments, etc.), followed by a “Plateau of Productivity” in which we currently find ourselves. How do I know we’re in the “Plateau of Productivity”? First, companies like Stripe are growing as fast as companies often do during Y...

Yesterday, a YC company called Coin launched an amazing convenience product to let people with multiple Credit/Debit cards manage them all on one physical, bluetooth enabled smart-card. It is an awesome piece of technology that allows consumers to simplify their financial life without asking merchants to adopt anything new. The internet, and I, were thrilled.

I just wanted to take this opportunity while it’s on everyone’s minds to remind you all of something near and dear to my heart: when you make a payment with a credit card, your merchant is losing between 1%-8% in fees, depending on the size and location of a transaction. Even if you primarily use your debit card to make purchases, if you make them online, you are still making the merchant pay “Card Not Present” fees that are typically $.30 +2.75-2.9% per transaction. That means, if you buy something for $10 online, you’re paying...

Me: “Wait, $1,500,000 divided by 25 is $60,000. Why couldn’t they use that money to hire new teachers? Am I missing something?”

Eva: “You’re not missing anything. Just wait”.

This past Monday, I spent my first night attending Municipal Government meetings at Richmond’s City Hall. It was, in a word, enlightening. On a night that featured a contentious City Council meeting featuring discussions about alcohol and gay rights (two things I care deeply about), I decided to let my good friends Matt and [Callie](http://twitter.com/calliegotclass handle the City Council meeting while I attended a meeting of the School Board.

Since I was 15 years old, the Richmond City Public School system has kept me up at night. It inspired me to start a run for Mayor in 2008 (which I, regrettably abandoned to work for another campaign) when I was 18, and despite a tumultuous and eventful life since then...

The term “Minimum Viable Product” has become almost a religion to the startup community. The idea of a “Lean Startup” is gaining popularity, several high profile companies have exited only after “pivots”, and the “launch fast and iterate” mantra is nearing ubiquity in startup circles. I have noticed, however, that the term is as misunderstood as it is pervasive. Entrepreneurs are constantly pushing back against the concept, arguing that they need a fully built product to launch, that they need a professional designer to get attention, etc. etc. I believe this is driven largely by fear, namely the powerful fear of sucking. After working with entrepreneurs for the last few years, I’ve found that the only way to rid yourself of urge to resist lean techniques is to replace the fear of sucking with another fear: the fear of wasting your life.

The problem most entrepreneurs face is that they...

“Good enough for government work” - we’ve all heard this mildly satirical phrase uttered when work crosses into that grey area where it can be loosely be called “finished”. You may even, as I have, heard it used in reference to ACTUAL government work. When I was 18, I spent the summer as a janitor for the Chesterfield County School System, “working” 10 hour days 4 days a week in a school with no kids. As you can imagine, there were lots of *good enough for government work*s going around THAT summer.

Turns of phrase like “Good enough for government work” may wrench the stomach of the American people, but they exist because they reveal an kernel of truth: if you work for or contract with the government, that shit is GUARANTEED. Your bills WILL be paid, your job is unlikely to go away, and you’re unlikely to be fired for anything short of extreme incompetence (and even then, you’re...