Rabois recently resigned from Square, where he was serving as COO in January after an employee accused him of sexual harassment. Square accepted his resignation but has so far backed Rabois and he joined Khosla Ventures in February. Vinod Khosla said in an interview at the time that he was consistently impressed with Rabois’ business expertise, and said he heard from entrepreneurs that Rabois was one of the most sought-after advisers in Silicon Valley.

During the Founder’s Showcase event on the future of investing on Wednesday, Rabois didn’t break a lot of new ground, but here were five things he told us:

His “Spidey Sense” tells him the Series A Crunch is probably real

Various people have written about the Series A crunch, and Rabois said he thinks it’s probably not just hyperbole. It is actually getting harder for companies to move from raising a seed round to raising a Series A round, especially with crowdfunding platforms like Kickstarter making it easier to get in the game.

“My spidey sense is that there is a real change,” he said.

Half the battle for startups lies with people

“Capital is one of the resources you need to build a real business, but people are the other. And people are incredibly scarce,” he said.

Party rounds are not that effective

“When you do that, no one really cares. They won’t wake up in the morning and think about your company. Most of the people will return your call and try to be helpful, but it’s very different having a partner and having an investor,” Rabois said of party rounds, which are investment rounds involving a large number of people where no one has a substantially larger stake.

When dealing with the press, be honest

Having worked on communications teams for a variety of startups, Rabois said honesty is the best policy and it’s not worth taking short-term gains if you think you’ll be around for a while. This gets harder if a reporter hears that you raised funding that you’re not ready to announce, but he said he’s always tried to give more than a “no comment.”

Being a good VC is an art, not a science

In response to questions about metrics he looks for or benchmarks he wants to see in companies he invests in, Rabois said metrics are important to an extent, but anyone can look at numbers and make a call. Being a successful venture capitalist is about the art of recognizing unique founders or market opportunities.

“It’s pretty much a commodity skill to look at numbers. It’s not a real skill,” he joked. “Investment bankers can look at metrics.”

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“We’re known for big bets and bold swings, and not being like a traditional venture investment firm,” said Vinod Khosla, founder of the firm and who Om feels is one of the Valley’s “super VCs,” in an interview discussing Rabois’ addition.

“We look for people who’ve earned the right to advise entrepreneurs. So we look for people who entrepreneurs look out for and who say, ‘I want you on my board, I want you as a mentor,’” Khosla said. “And Keith, as I did my reference checks in the Valley, he was really at the top of every CEO’s list.”

Rabois’ next move has been a topic of interest among the technology community, considering his past expertise at companies like PayPay, LinkedIn, Slide, and others. His addition to Khosla was suggested by Kara Swisher at AllThingsD this past weekend, after The Wall Street Journal wrote that he might join Airbnb.

“I love Khosla Ventures’ vision and passion for assisting the next generation of entrepreneurs,” Rabois said in a statement. “The Khosla team encourages entrepreneurs to be bold. And the team’s legendary work ethic ensures that entrepreneurs will receive the best possible assistance.”

In January Rabois stepped down from Square, where he was COO, after allegations of sexual harassment by a fellow employee. Square strongly backed Rabois, and the executive wrote in a personal blog post that he had engaged in a relationship with that employee but that it had been mutual. Khosla Ventures did not comment on Rabois’ legal issues. Khosla serves on Square’s board, as Square is one of the firm’s portfolio companies.

“I couldn’t be more excited to see two of the top entrepreneurs I know, join forces at Khosla Ventures to support and coach the next generation of entrepreneurs the world over,” said Square founder Jack Dorsey in a released statement.

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Square confirmed the report, saying in a statement:

The first we heard of any of these allegations was when we received the threat of a lawsuit two weeks ago. We took these allegations very seriously and we immediately launched a full investigation to ascertain the facts. While we have not found evidence to support any claims, Keith exercised poor judgment that ultimately undermined his ability to remain an effective leader at Square. We accepted his resignation.

In a post on his personal blog on Friday, Rabois wrote:

In May 2010, I met someone via mutual friends. With increasing frequency, we hung out, drank wine, and I helped prepare him for interviews with tech startups. As our friendship deepened, we spent more time together, and our relationship became physical. … Several months after our relationship began, I recommended that he interview at Square. He went through the interview process and was ultimately hired. I had no impact on his potential success at the company. At no point did he ever report directly to me, and I have seen his work product less than a handful of times.

Rabois denied the allegations:

I realize that continuing any physical relationship after he began working at Square was poor judgment on my part. But let me be unequivocal with the facts: (1) The relationship was welcome. (2) Square did not know of the relationship before a lawsuit was threatened; it came as a complete surprise to the company. (3) He never received nor was denied any reward or benefits based on our relationship. And (4), I did not do the horrendous things I am told I may be accused of. While I have certainly made mistakes, this threat feels like a shakedown, and I will defend myself to the full extent of the law.

He said he “decided to resign from Square so my colleagues could continue to do great work without the distraction that a lawsuit would most certainly bring.”

Square appeared ready to back Rabois in the suit. Richard Curiale, outside counsel for Square and Rabois, told AllThingsD, “I have not as yet found any conduct that is illegal and therefore there is no adverse relationship between Keith and Square. We don’t pay for claims that have no merit to them, because it amounts to extortion.”

Square, a Silicon Valley-based startup that allows vendors to accept credit card payments from mobile phones, was cofounded by Twitter cofounder Jack Dorsey in 2009. The company has raised over $340 million in funding, with a reported valuation of $3.25 billion.

This story was continuously updated Friday afternoon as information became available.

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According to AllThingsD, and supported by statements from Square and Rabois himself, the investor and executive has decided to part ways with a company that’s considered one of the brighter stars in the Silicon Valley constellation. Led by Dorsey, Twitter’s co-founder, Square has captivated small businesses with an easy-to-use credit-card payments system, and Rabois has been one of the more vocal proponents of Square’s approach to mobile payments.

It’s not entirely clear at this point what Rabois might have planned for the future, but AllThingsD points to “disagreements” between Rabois and Dorsey over the future of Square.

Rabois spoke at our Mobilize conference last year, and a video of that session follows below.

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These deals don’t really tell the story of Gurley. I first met him when he was a former Wall Street analyst and our relationship began with me questioning his analysis. He switched teams and joined Benchmark at the height of the first Internet bubble. Gurley, who in the past used to write the Above the Crowd column for C/Net, took a step out of the limelight. Of course, that is par for course, investors at white-shoe firms tend to be less public than analysts, so our interactions decreased overtime.

When I moved out to San Francisco almost a decade ago, we touched base again, and since then have made it a point to see each other at least once every quarter. He has a very unique point of view about Silicon Valley, the technology industry and the kind of companies he likes to invest in. Polite as he is, he doesn’t sugarcoat anything and has given me advice over the years that was a bitter pill to swallow at the time, but in hindsight, turned out to be exactly what I needed. The only thing we don’t agree on: his love for sports that don’t make sense to a short, somewhat rotund guy like me, basketball and college football — the American kind.

Last year Chris Albrecht and I did a lot of documentary style interviews with folks such as angel investor Chris Dixon, Square COO and angel investor, Keith Rabois and Zimbra co-founder Satish Dharmraj, but this year I took a step back, mostly because I wanted to regroup and rethink whom I wanted to interview. I wanted to bring fresh insights from people whom I respect and believe have something interesting to say. I couldn’t find anyone better than Bill Gurley to kick off this occasional series.

In this interview, Gurley talks about a whole bunch of things including the craft of being a VC, the changing VC landscape, and most importantly, his thesis around reinvention of everything local. The interview was 45 minutes, so we have made it simpler by creating six chunks for easy consumption. We will post the entire interview later. Enjoy the videos.

What it takes to be a VC.

What is the role of a VC? Questions every entrepreneur should be asking.

How network effects reshape local commerce.

What it takes to survive downturns.

Beyond the obvious: What are the opportunities in venture capital?

On Above The Crowd [Slight audio issue here.]

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Some of the more poignant thoughts from our Mobilize speakers exemplify this theme, so here are a few I thought worth sharing:

• Don’t count out HTML5 just yet. Mark Zuckerberg may not have been happy with HTML 5 for Facebook, but Spencer Rascoff, CEO of Zillow said, ”In my mind, we’re moving more towards a world where apps are basically bookmarks for mobile websites.” Native apps will surely have a place in the future — and its users are more highly engaged, says Rascoff – but mobile web technology is still improving.
• The “point of sale” is now everywhere. While near-field communications (NFC) payment methods haven’t yet taken off significantly, alternative solutions that align more with traditional payments are becoming popular. Square COO, Keith Rabois noted that “35 million unique Americans have paid with Square,” or roughly 11.1 percent of the 314 million population in the US. Take into account that a number of the total population is too young to actually make purchases and the adoption figure rises even higher. Coincidentally, I had my first Square experience on the way to Mobilize; my taxi drive used it with his Galaxy S III smartphone to process my fare from airport to GigaOm HQ.
• Video is becoming a primary mobile activity. The granddaddy of all video sites, Google’s YouTube, is now delivering 25 percent of its content to mobile devices and the figure is likely to rise in tandem with mobile broadband subscriptions. In Korea, for example, which has 91 mobile broadband subscribers for every 100 people, YouTube’s mobile delivery is closer to 50 percent, said Shiva Rajaraman, YouTube’s director of product management. This means we’ll see a greater need for faster mobile broadband, offline playback support and improved video compression technologies in the future.
• Connected homes will only appeal if the solutions are simple and add value. As a do-it-yourselfer, my own connected home is a mishmash of networks, protocols, products and interfaces. “Most consumers really, really, really don’t want to be integrators,” said Bill Brown, GM of converged consumer solutions for Motorola Mobility. Watch for more plug-and-play modules that talk seamlessly with each other instead of more complex, centralized home servers for connected homes.
• Developers need to consider the broadband their software needs. Third party apps that eat through gobs of mobile broadband could passed over for similar apps that use less data. “You want an app that does 50 miles to the gallon, not 10,” suggested T-Mobile CTO, Neville Ray. As our mobile software gains more complex functionality, it’s important that developers temper the need for cloud access and even consider offline use-cases if possible.

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“We’re in the software business, so we produce technology that substitutes for human beings,” Rabois said at GigaOM’s Mobilize conference in San Francisco, noting that the physical Square reader sells itself through physical stores that use the product. “When I go to the coffee shop, I see it, when I get in the taxi, I see it,” he said.

Rabois commented on the partnership with Starbucks, noting that one of the biggest benefits for Starbucks stores and customers is that the national chain will be able to better recognize local customers and treat them the way a local coffee shop might.

“75 percent of Starbucks payments are anonymous, and paying with Square allows you to forge a relationship with everyone who makes purchases in your store. I go to my neighborhood bar because they know what I like to drink,” he said. “We can do that at scale for every business in the United States.”

The company is increasingly facing competitors looking to get into the mobile payments space. Just this week, Groupon launched Groupon Payments, and PayPal has a similar product as well.

Unlike Square, PayPal has a sales team, but Rabois didn’t seem threatened.

“They’re going to need it,” he said.

Check out the rest of our Mobilize 2012 coverage here, and the live stream can be found here.

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Intuit, for example, has been linking its GoPayment mobile payment service to its QuickBooks Online accounting software, making it easier for its 8 million existing software customers to go mobile. Now, it’s taking another key step by integrating its QuickBooks Point of Sale product with GoPayment. That means that the 200,000 customers who use QuickBooks POS hardware and software will have an easy way to combine a traditional POS experience with a mobile payment service.

For business customers who take advantage of this combo, that means they can have workers taking payments in the aisles of stores or out at trade shows or events, with all the transaction data, inventory and analytics handled by one system on the back end. The mobile app can be populated with inventory items pulled automatically from QuickBooks Point of Sale. By offering both options, Intuit gives companies more flexibility to grow from a simple mobile-only retailer to a bigger storefront merchant. Between QuickBooks POS and GoPayment, Intuit is currently processing $6 billion annually and reaching 23 million consumers, the company said.

Trevor Dryer, Intuit’s Head of Product Management, Mobile Payments & Point of Sale, told me Square and its Square iPad register are appealing products for very small businesses and merchants getting started. But he said as businesses start to grow with more inventory, employees and more locations, they’re looking for a bigger system to handle not just payments but the entire suite of services including demand generation, engagement, loyalty, inventory, analytics, accounting and other needs.

Dryer said QuickBooks Point of Sale and GoPayment offers a more robust set of features including traditional hardware such as a barcode scanner, barcode tag printer, receipt printer, credit card reader and cash drawer. Intuit’s system can handle thousands of inventory items and has better options for grouping products and customer tracking, he added. When combined with QuickBooks’ deeper inventory and accounting software, he insists it makes more sense for many businesses.

“Square and Square Register, they’re very light solutions,” said Dryer. “It might be great for a small business starting out, but as the business grows they need more functionality.”

In my recent interview with Square COO Keith Rabois, he said the start-up already has a set of tools for customers that is lifting sales by double digits. But he also said there’s still a lot more work being done to build out Square’s features.

This is one area that competitors feel they can exploit. PayPal and Intuit are bringing a set of existing tools to bear on small businesses while VeriFone is relying on a more open approach for its SAIL mobile payment product, allowing merchants to plug in their preferred tools. The race will be on for Square to build up its offering as it goes up market before its rivals can cut it off with their own products.

QuickBooks POS will start at $1,099 for a basic version of the software and $1,499 for the pro version. With hardware, the pro version costs $1,899. The pro multi-store software sells for $1,799 and $2,299 with hardware. That’s much more expensive than Square Register, which is free but requires an iPad.

But Intuit is highlighting where the battle is going. Mobile payment is still just getting underway for many merchants and there’s a lot of room for growth for companies like Square and others on the low end. But the competition will really intensify as everyone converges on bigger merchants with more transactions.

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Even with growing competition from some well-funded companies, Square hasn’t slowed down at all. It is now processing $5 billion on an annualized rate. The company is up to 300 employees and has taken over an entire floor of the old San Francisco Chronicle building, giving it room to add another 150 people. And it’s reportedly raising $250 million at a possible $4 billion valuation.

But the rivals keep circling, looking for ways to eat into Square’s growth. PayPal launched PayPal Here, while VeriFone rolled out SAIL, even going so far as to copy wholesale portions of Square’s user agreement. Groupon is reportedly testing a payment tool that undercuts Square’s fees while Intuit, SalesVu, PayAnywhere and others are also looking at putting the squeeze on Square.

I sat down with Square’s chief operating officer Keith Rabois to talk about where Square is now, where it’s headed and how it expects to compete as the competition closes in. He talked about how the company is not interested in a piecing together a solution, nor is it looking at hiring a sales staff anytime soon. And it’s not making any immediate moves to address the online sales channel for merchants. He said Square is lifting sales for businesses by double digits and a lot more in some cases. And to all the competitors, he said, it takes more than just a press release to compete.

This interview was edited for clarity and space.

Ryan: How do you feel now that Square is walking around with a target on its back?

Keith: There are more and more people obviously in financial services and in technology who are interested in what Square is doing because we have had a lot of market traction. We’ve established a high affinity brand and we’re helping merchants. That obviously attracts interests. That said, what we do is complicated and to do it well is incredibly complicated. It’s not as easy as saying we’re going to cut and paste various things and you have Square.

Ryan: Are you planning to target medium or large-sized businesses in addition to smaller merchants?

Keith: If you’re a sole proprietor who opened a business because you have passion about a craft and because you like the relationship and dialogue with your customers, you can’t throw a person at IT. There’s no one to install these terminals. There’s no one to look at your bank statements, study them and optimize them. At some level of scale, a business has enough professionalization that they subdivide so they have a separate HR professional and you have a separate IT professional and you have a separate finance professional.

Below 100 employees, you generally can’t allocate people that way, so we have we have an immense value proposition. Over time, I suspect we will innovate for large businesses, too, but today that’s a pretty big market. For example, I believe if you look at the U.S. commerce department they estimate that sales for businesses with 20 employees or less is about $22 trillion a year.

Ryan: With all the things you need to do, how do you prioritize? Deals, loyalty, discovery, all of the above?

Keith: We think there is one narrative, one story. We don’t think of them as separate. It’s how do we make life better for business people, entrepreneurs and really look at what are the sources of friction on both sides of the counter — so, consumer friction as well as merchant friction, and how do you eradicate them. You’re right, we can’t do them all at once. We have to sequence some things, but there is a consistent narrative, which is reinventing commerce to make the commercial experience better, more human, more enjoyable and delightful.

Ryan: Your competitors all think there is something they can do better. They’ll concede that you’ve been successful but that they’re going to cut you off at the pass. What do you think when they take aim at you and feel that they will have a faster path to a more robust set of tools, whether it’s in house, or buying a bunch of companies or opening up with APIs?

Keith: I’ve yet to see in technology a company following someone else’s strategy that jumps ahead. Ultimately you have to have a vision of what you’re building and a proprietary approach. Leveraging a competitive advantage and just following what other people do never yields success. A reader is a small piece of what we do. Square can’t be distilled by cutting and pasting or doing a Zynga clone of our website.

Ryan: Other competitors will argue they have more tools, like better analytics, business software or deals and loyalty. Do you feel like you can do this all in-house?

Keith: Yes, absolutely. I think there’s strength in crafting an entire experience. You can optimize it. You don’t have these component misfit problems. Generally, any time you put together component pieces, you are imposing friction on your users. If you’ve bought an audio system for your house, trying to set that up is a major deterrent. Trying to figure out which component goes with which component, it can deter people from actually buying the best new systems. If you craft an experience end-to-end, it just works out of the box.

Ryan: I hear from other companies who say they’ve gotten Square converts because they offer more tools.

Keith: Let’s be real! Is there a PayPal Here user in America that’s live? If you’ve found one, let us know. Ask any of those people for actual users you can talk to. It’s really easy to put out a press release and say, hey, we’ve got some new features. The market will speak for itself.

Ryan: How long before people have these tools? It seems like you have the beginnings of a lot of them, but the depth isn’t there yet.

Keith: I think the tools are pretty compelling. You should talk to our users. They will tell you how it’s improved their business, how it’s increased their sales. Increasing sales by 15 percent for a business is the difference between paying rent and not, or being able to hire a new employee or not. So, we’re already doing that. We’re already lifting sales by double digits across the businesses that adopt Square and sometimes, it’s greater than double digits.

Ryan: Are the reports that you’re raising $250 million accurate?

Keith: All I will say is that there are a lot of people who invest for a living who have always been interested in Square.

Rabois at Square’s San Francisco office

Ryan: Going forward, what’s the relationship between Pay with Square, your cloud-based payment app, and the main Square experience? Are you going to be more of a consumer brand or more of a B2B tools company.

Keith: I think it’s both. Apple is a consumer and an enterprise brand. There’s no inherent tension between the two. Pay with Square is a consumer application that powers merchant success. People who pay with Square come back to your business more frequently. And we have a directory that exposes businesses to be discovered and that generates new customers, so it’s both a value proposition for the consumer and a great business tool for the merchant. In my ideal world, using Square to accept payments is just as easy as using Facebook. Actually, it should be easier because the privacy setting complexity isn’t part of it.

The vision of Pay with Square is simply a one-click experience for the real world. So imagine you have an iTunes account that allows you to go everywhere and allows you to buy things because you can afford them and you don’t focus on the mechanics of paying at all. You say put it on Ryan or put it on Keith. And so you have this invisible account in the background that just takes care of things.

Ryan: When I look for places to Pay with Square, it still seems limited.

Keith: We are a little like Yelp or Open Table, where obviously, the more merchants you have in a geographic region, the better it is for consumers. That’s not surprising. I think you will find in most NFL cities, the cities with NFL teams, increasingly you see Pay with Square merchants everywhere.

Ryan: What is your plan to accelerate that? Is there a sales team?

Keith: We do not have a sales team. I think what we found is that Square is such an amazing experience that when people tried it in the real world, they’re actually really impressed. And they actually ask for it. “What is that and where can I get one?” So that’s the best set of customers you can have. They actually proselytize for us. We’ve invested a lot in retail so we’re now available for sale in over 20,700 different locations in the United States. From Apple to Best Buyto Walmart, Target, FedEx, Staples and Office Depot, and that’s important.

Ryan: But people who use a mobile wallet — they want to use it at small stores and big stores. Is your retail network at this point too incomplete to be really useful to consumers?

Keith: Most Americans use multiple forms of payment every week. I don’t think Pay with Square has to be replacing all forms of payment immediately. But the macro trend is once you try the product, you’re going to want to use it in more and more places, and you’re not going to go backwards toward paper, and so our first job and mission is to get as many people to try it. And that they’re delighted and stick with it, sort of like Facebook engagement. Facebook has this massive engagement compared to every other website because people use Facebook and they really enjoy the experience. Pay with Square needs to work the same way.

I think secondly, when I have that experience, I’m going to go into the bigger businesses and ask, “Why the hell don’t you take Pay with Square?” It’s like how people do with American Express. There are a lot of people who prefer to use their AmEx card. That is why large retailers pay a higher discount rate to AmEx because there are Americans who prefer to use their AmEx card. As long as Americans prefer to use Pay with Square, larger businesses will definitely start accepting it.

Ryan: Will Square be in-store only, or do you have online ambitions as well?

Keith: Increasingly many business are at least selling some of their wares through an alternative channel. So that’s a macro trend. However, we started in the real world. We believe in the real world, which still accounts for 95-96 percent of retail commerce, compared to the online world, which is roughly 5-6 percent. So, I think the focus of Square is correctly in the real world.

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Paige Craig’s photo courtesy of Venturebeat.

BetterWorks, one of the most well known startups to emerge from Los Angeles seems to have hit an air pocket. The company which was started by super angel, Paige Craig (along with Zao Yang and  George Ishii) is said to have laid off close to thirty people, a very credible source of mine tells me. The company is said to be looking at making some dire choices. I left voice mail for Craig and emailed him and am awaiting a comment from him.

I emailed his lead investor, Satish Dharamraj of Redpoint Ventures, who is offline for family reasons and pointed me back to Craig. My attempts to reach some of his other investors in the company have drawn a naught as well. Dharamraj is the lead investor in the company which raised a whopping $8 million in August last year. Forbes put the estimated valuation of the company at $100 million and recently called it one of the 10 startups changing the world.

Craig, who dodged my phone calls and repeated requests told Pando Daily:

The outside sales model is a big risk. When we were on-boarding early adopters, the signals were that it was working. Once we got past the early adopters, the real numbers didn’t justify the cost.

To that I say, keep spinning dude!

Other investors in the company include Jeff Clavier of SoftechVC and Ron Conway’s SV Angel. The company also attracted angel dollars from well known angels such as Naval Ravikant of Angel List, Keith Rabois, COO of Square, Michael Jones ex-MySpace, Brian McClendon, VP of engineering at Google and Yishan Wong, a director of engineering at Facebook.

BetterWorks describes itself an employee perks program. The idea was just as Google and Facebook offer a variety of perks (meals, coffee, gym, etc.) to their employees, startups (and others) could use BetterWorks’ platform to offer perks to their employees. And because it can aggregate a lot of employees, the company could get better offers for the employees and the whole process could be managed through its web-based interface.

Update: I used exclusive in the headline, but later was told by Erin Griffiths that PandoDaily beat me to the punch. Apologies to them and to the readers. 

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