So you have a YCombinator interview coming up?  Congratulations.

You’d like some advice from a YC alum (S ’11) about how to prepare?  Happy to help.

If your startup is interviewing with YC, you’re probably all set on the product side and you probably have a great team.  That’s the foundation for a good interview.  You need to make sure you can explain what your product does in plain, clear, concise language and explain the value and expertise that your team brings to the table in the same way.  The YCombinator partners may have questions for you about either of those topics, but if you’ve been offered an interview, you’re probably capable of discussing those. You don’t need my help there.

Where you might struggle is when they start asking about your users.  My advice to every startup preparing for a YC interview is to know your user and to be prepared for a user-oriented line of questioning.  You might know your product inside and out and you certainly know why your team is awesome, but do you know your user?  Really?

Here’s an example of the sort of user-oriented questions that I see trip up many of the startups that ask me for YC interview advice.  You need to have answers for these.  You might not get asked them (I was asked them during my interview), but if you do, be prepared.

• Who is your user?
• What problem are you helping them with?
• Why is this a problem for them?
• What do they use to solve that problem right now?
• No, what do they really use to solve that problem right now?
• What do they like about this solution?
• What do they not like about this solution?
• What do they wish that solution could do for them?
• How is your solution better?
• How much better is your solution?
• Why would they switch to your solution?
• What do you know about these users that no one else knows?
• How many of these users are there?
• How many do you have now?
• How did you get them?
• How will you get more?
• How many more will you have in 3 months?
• What do these users currently pay to have this problem solved?
• Would they be willing to pay more for something better?
• Why are these users good users to try to solve problems for?
• What other kinds of users could you go after once you get all these users using your software?

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This sort of customer drilldown can be disorienting at first if you’re not ready for it.  Most of the startups that ask me for YCombinator interview advice can’t answer more than a few of these when put on the spot.  This is understandable.  As an early stage startup founder, you have a lot of code to write.  As you write that code, it is very easy to get bogged down in the details, focusing on what your app can DO rather than the needs of the person that’s going to USE it.

But if you want your startup to be great, you need to know your users.  You need to be relentlessly empathetic.

Paul Graham has written that good startup founders are relentlessly resourceful.  This is true.  The best companies from my YC batch are run by founders who could find their way home in a few months if you airdropped them into a foreign country unexpectedly.  They can find a solution, even a crappy one, to any problem you put in front of them.

But another quality that the best startup founders have is that they tend to be relentlessly empathetic as well.  Oftentimes, this comes down to a single founder being the “user guy/gal” who makes it his or her job to talk to users all day, and in an empathetic way.

It’s very easy to talk to users without empathy.  I do this often and have to catch myself.  When you talk to a user without empathy, you’re looking for confirmation of your own beliefs and assumptions rather than actually listening for what their problems are and what kind of help they’re looking for.  Just listening isn’t enough.  You have to listen empathetically to learn things that will help your company take over the world (Peter Thiel refers to these sorts of strategic insights as “secrets” in a lecture he gave last year).

When talking to YC companies during office hours, PG often references how Airbnb CEO Brian Chesky flew back to New York City every week during his YC session so he could talk to users and stay at apartments listed on Airbnb in NYC.  Airbnb had a critical mass of listings in NYC at the time, so it meant he needed to be there, not in San Francisco, even though it required a lot of obnoxious travel during YCombinator.  The reason this was so impressive and memorable is because it was a display of relentless empathy, the kind of empathy that eventually helped Airbnb build a great product that million of people love.  By spending time in New York, dogfooding his own product and talking to users, he was able to learn things that made their business better.  (Did you know Airbnb thought the “breakfast” in Airbed & Breakfast was a crucial part of their product experience at one time?  A lesser startup would have persisted in this assumption for too long.  By talking to their users relentlessly, Airbnb was able to learn that no one cared about the breakfast, ditch it, simplify their product and make it better for it.)

So as you prepare for your YCombinator interview, ask yourself, do you know your user?  Are you able to drill down into the minutiae of their pains and the tools they currently use to ease them?  How deep can you get into the questions I posted above before you hit your first “I don’t know?”

Are you bringing relentless empathy alongside your relentless resourcefulness?

If so, you’re in good shape!  Good luck!  If not, it’s time to start sending more e-mails, setting up more customer phone calls, and having coffee with A LOT of potential customers.  If you can’t get inside your user’s heads, your software is never going to get inside their hearts.

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Brad Flora is co-founder and President of Perfect Audience.  A former journalist, he started Perfect Audience to help make programmatic advertising and retargeting something that companies of all shapes and sizes can benefit from.  He likes dill pickles and recently took first place in the Star Cup at 150cc in Mario Kart 64.

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Matt Watson’s first startup, VinSolutions, sold for $150 million—not bad for something he says was “completely bootstrapped.”

Now he’s taking lessons learned from his first company and funneling them into his latest venture, Stackify. In fact, the idea for the company grew out of frustrations Watson encountered at VinSolutions. Stackify provides tools for software developers to monitor their applications using a mix of server monitoring and remote access.

At VinSolutions, 40 software developers worked for Watson. “We literally had people lined up at our door for half the day who needed help doing things because we were the only ones who could do them,” says Watson, Stackify’s founder and CEO. “Other people didn’t have access to all the production servers because we didn’t trust them. So our solution allows us to give them a certain amount of access that they can’t cause any harm, but is the amount of access they need to do the troubleshooting they need to do.”

The Kansas City-based startup was founded in January 2012 and now employs about 15 people. Since the product’s launch in January 2013, about 300 users have signed up for the service, including a “handful” of paying customers, Watson says.

Although there a few differences between VinSolutions and Stackify (namely, the former’s initial lack of funding), Watson still prizes the ability to execute innovative marketing stunts with a quick turnaround to draw in potential users.

“The biggest difference is just having the funding,” he says. “The original company was completely bootstrapped, so we never had the money to do anything the right way.”

Stackify, which is funded by Watson, has been able to do more advertising, hire a salesperson, and funnel more resources into R&D than VinSolutions, which didn’t have an advertising budget until four or five years in, he says. “We cut every corner we could before and struggled forever because we didn’t have the money to do anything the right way. But ultimately we ended up being successful. It’s just a very different road.”

And while this time around Watson can afford to try different approaches to advertising (specific websites have been great; print mags, not so great, he says), it’s some of his reactive and spur-of-the-moment marketing techniques that have garnered Stackify positive attention.

Recently, Watson seized Valentine’s Day as an opportunity for playful outreach: He crafted a tale of forbidden love between Dev and Ops. (“Relationships are always hard, and they know they can solve most of their problems with a reboot, hotfix, or patch cable.”) The short post attracted 3,500 visitors to the site.

“We’re just trying to take advantage of things we can take advantage of and get our name out there,” Watson says.

Watson is big on looking for opportunities and then running with them, which he says is an advatage of working with a smaller company. For example, when Microsoft Windows Azure’s SSL certificate expired, it took down a handful of services, including Stackify’s. “We circled around and realized that there weren’t really good ways to get notified that SSL certificates expire, so we actually, over the weekend, created a free service,” he says.

Stackify put out press releases, and Watson did a few subsequent interviews. “Being very agile is really important,” Watson says. About three hundred people signed up for the service, CertAlert.me, within the first week.

“The other big difference was when we started (VinSolutions), we never had a salesperson for the first probably two or three years because all of our customers were a referral or people who found us on the Internet, kind of more organically,” Watson says. “It’s nice to actually have salespeople and a marketing budget.”

For now Watson is focusing on building more functionality into Stackify’s service. He says it’ll take three or four years to achieve his “grand vision.”

In the meantime, the startup veteran recommends reaching out to and networking with others who can act as mentors.

“My advice for most people is to do everything they can not to actually take the money,” Watson says. “We’re in a different place because I’m funding it. So I’m not dealing with other business partners or things like that, I’m not chasing money around. A lot of these guys spend all their time chasing money and not focusing on the product. You’re better off just focusing on the product and building a product that creates revenue instead of chasing money. If a product can’t create revenue, then it’s not typically a worthwhile business.”

The way Wade Foster tells it, there’s no big mystery as to why his startup Zapier, which allows users to easily connect web services, has grown to process 100 million API requests per month.

“A lot of startups have this thing where they build something and they realize nobody cares about it or they have to iterate over a couple different things,” says Foster, Zapier’s CEO and co-founder. “It was never like that with us because we knew from the get-go that there were a lot of people who could use a product like this. So whether it was useful or not never really was a question.”

Foster attributes Zapier’s success to what happened before the company was even formed: He and co-founders Mike Knoop and Bryan Helmig identified a real problem and came up with a useable solution. Now they concentrate on constantly fine-tuning the user experience for their customer base, which is “well into the tens of thousands,” Foster says. Read more »

The fine folks over at FBPPC.com let me guest post a guide to what NOT to do with your Facebook retargeting campiagns.  You can read it there or here below:

So you’re advertising on Facebook Exchange and want to make it rain conversions?  Real-time bidding is a complicated, messy process with dozens of variables at play. Here are 5 to-do items that are a good start for pointing you in the right direction.

1. Stop retargeting users who already converted.

Retargeting the right people is half the battle in creating a successful campaign.  Sometimes, identifying those people can be tricky, but other times it’s crystal-clear.  Those people who just signed up for your offer? Those are the wrong people to retarget.  Stop doing that. Create a cookie list that captures recent converted users, then exclude the users in that list from your campaigns so you don’t spend any more than you already have advertising to them. This will save you dollars so you can spend them getting more conversions. Read more »