Some good discussion in this thread at Hacker News about how to evaluate people with a business skillset if you've got technical skills already.

I reckon "a knack for getting money" is probably the most key thing to look for in a businessperson. Some people have a knack for getting money.

All the business skills in the world without the knack for getting money doesn't fly. Well, maybe for employee #7,632 once a company's made it. But not for starting something up. You need to hustle and get money of some form real fast early on. A business guy who can't get money is probably worse than useless - if he wasn't on board, you'd be worried about solving the money problem yourself. But since he's supposedly the business guy and seems to be doing business guy stuff, you think things are cool. But things aren't cool. Go long enough without money, you die.

That's bad.

So, where do you get a knack for getting money? We're not born with it. It's acquired through action somehow. What's it take?

Well, let's look at Judd Weiss.

If you want to get a feel for what someone with a knack for getting money thinks like, you should probably read Judd's About Page (warning: bad language. worse than me, even). It starts:

Success and failure, they are separated mainly by those who try, those who don’t, and all the subtle levels in between. To try means to move your ass, get out there, and hustle. The whole fucking world is open to you. Everything you love in this world that nature didn’t deliver to you was created by a hustler. By those who try. All the billions of people on this planet, they each need help with almost every detail of their existence. You can certainly be of value somehow. That’s what we’re going to focus on a lot here at Hustle Bear. Hi there, I’m Judd.

Continuing -

I’m 29. I’m a hustler. The last steady salary job I had was scooping ice cream at Coldstones at 17; since then I’ve been winging it and hustling, fortunate to learn how to thrive without a steady salary. I had 9 odd jobs when I started college (sold knives (cutco), sold phone service, computer consulting , math tutoring, sold Rolexes, etc.); became a millionaire by 24 at which point I bought a large modern house in Bel Air; got ranked among the top 10 Commercial Real Estate agents in California and the top 20 Commercial Real Estate agents in the World at Remax Commercial for 2005 and 2006; started my own Commercial Brokerage before witnessing the complete total death of Brokerage; prompting me to start new companies in fields I knew nothing about and had no network of contacts (like Parking) and rapidly bring these companies to success. Every business endeavor I’ve devoted myself to I’ve made a success. Mostly because I’m a maniac.

Go read the whole thing when you're done with this - there's an education in there.

What's most key to getting a knack for getting money? Me, I don't have it. Well, I do more than a lot of people, I've done alright for myself, but not like Judd.

Where's the knack come from?

I don't think it's particular skills. Anyone smart enough can learn the basics of negotiating, and plenty of people who've learned on negotiation still don't have the knack. Oh, it's good, I totally recommend you learn how to negotiate. Everyone should. But by itself, it doesn't translate to a knack for getting money.

Is it effort, a willingness to fail, and the ready-fire-aim/look-before-leaping approach?

Well, you definitely could use some of that, yes. But think about it - I bet you know someone that does a great job at executing and doing difficult things for a nonprofit, charity, religion, or some such, but can't get money for themselves and their own projects.

(Note: I think that's bad, and think that building and getting resources for yourself is good if you're a virtuous person. If you're a regular here, you probably feel the same way. If you're stopping by, let's skip the hand-wringing about different priorities for now. We're talking about where a knack for getting money comes from here.)

Okay. So, skills alone doesn't get you there. Negotiation, accounting, probability, general social skills, industry-specific skills... these are good and help, but don't directly translate to a knack for getting money.

Action-taking, effort, willingness to fail - these might be necessary, but aren't enough alone to get money.

Heck, I love the word "hustle", but hustling alone isn't enough. There's people that can absolutely hustle and work the phones and shake hands in order to work for a social cause, but would fall apart if they were tasked with getting money in order that their for-profit business doesn't go broke and die.

What is it then?

Well, let's look at another guy who has the knack for getting money.

It's worth reading 50 Cent's Wikipedia page - here's the Non-musical projects section:

Jackson has established himself in a variety of fields. In November 2003, he signed a five year deal with Reebok to distribute a "G-Unit Sneakers" line as part of his G-Unit Clothing Company. He provided the voice-over as the protagonist in the video game, 50 Cent: Bulletproof, which was released for PlayStation 2, Xbox, and the PlayStation Portable. Its sequel, 50 Cent: Blood on the Sand, was released in early 2009. He worked with Glacéau to create a Vitamin Water drink called Formula 50. In 2007, Coca-Cola purchased Glacéau for US$4.1 billion. Forbes estimated Jackson, who owns a stake in the company, earned $100 million from the deal after taxes. He has teamed up with Right Guard to launched a body spray called Pure 50 RGX Body Spray and a condom line called Magic Stick Condoms, in which he planned to donate part of the proceeds to HIV awareness. Jackson has signed a multi-year deal with Steiner Sports to sell his memorabilia. In 2005, Jackson made a cameo appearance on The Simpsons episode "Pranksta Rap", in which he makes light of his legal troubles. The same year, he starred alongside Terrence Howard in the semi-autobiographical film Get Rich or Die Tryin'. He starred in the 2006 film, Home of the Brave, as a soldier returning home from the Iraq War, traumatized after killing an Iraqi woman. Jackson is working on a role as a fighter in an Angola State Prison in Spectacular Regret alongside Nicolas Cage, and starred opposite Al Pacino and Robert De Niro in 2008's Righteous Kill, a movie regarding a police death. He also started the film production companies G-Unit Films in 2007 and Cheetah Vision in 2008. In August 2007, Jackson announced plans to launch a dietary supplement company in conjunction with his movie Spectacular Regret. In August, 2005, shortly before appearing in Get Rich or Die Tryin', Jackson published an autobiography entitled From Pieces to Weight: Once upon a Time in Southside Queens. In it Jackson explores the cultural and economic forces that led him to sell cocaine and crack, details his entrepreneurship as a drug-dealer and then as a rapper, and reflects on his own ethos and on society. On January 4, 2007, Jackson launched his G-Unit Books imprint at the Time Warner Building. He also co-wrote The Ski Mask Way, a novel about a small-time drug dealer who attempts to rob his employers, which is to be turned into a film. Jackson said he read Robert Greene's The 33 Strategies of War and worked with the author on a book titled The 50th Law, an urban take on The 48 Laws of Power. In May 2008, Jackson met billionaire Patrice Motsepe to forge a joint venture selling 50 Cent-branded platinum. In 2008, Jackson started a reality television show on MTV titled 50 Cent: The Money and the Power; the winning contestant, Ryan Mayberry, won a $100,000 investment from Jackson. In 2010, Jackson's film company Cheetah Vision landed $200 million in funding.

By far, the #1 thing for a knack for getting money is not having hangups about getting money.

Look at Judd -

"The last steady salary job I had was scooping ice cream at Coldstones at 17; since then I’ve been winging it and hustling, fortunate to learn how to thrive without a steady salary. I had 9 odd jobs when I started college (sold knives (cutco), sold phone service, computer consulting , math tutoring, sold Rolexes, etc.); became a millionaire by 24... [the real estate crashed caused the] death of Brokerage; prompting me to start new companies in fields I knew nothing about and had no network of contacts (like Parking) and rapidly bring these companies to success. Every business endeavor I’ve devoted myself to I’ve made a success. Mostly because I’m a maniac."

Judd hustles and gets money. Sold knives, phones, fixed computers, taught math, sold watches... got into real estate as a broker, bought and sold properties... got out of it when it's not viable and now owns a valet parking company and various other things.

He's got skills. He's got drive. He works hard.

But lots of people have skill, drive, and work hard without getting much of anywhere. No, the biggest thing is Judd has absolutely no hangups about getting money. If he sees opportunity to create some value and get some of the value, he gets in.

Look at 50 Cent - he's sold around 40 million records... I don't know what his cut is per album sold, but he probably made more money from the Glaceau Vitamin Water deal than he has from records.

He's got skills, he's got drive, and he works hard. But lots of musicians have skill, drive, and work hard. What sets him apart is that 50's got no hangups about getting money.

How many platinum selling artists are willing to go shovel snow for 100 bucks?

Probably the biggest thing that holds people back from getting money are hangups about it. How do you get over that?

Practice? Philosophy? Desperation?

Probably all of them. But I'd bet on the guy with no hangups about getting money and a little drive getting more money faster than someone with tons of skills but hangups about it. There's silly amounts of opportunity all over the place. The menus at the place I eat breakfast in Saigon are worn out and cheap-looking. I know the top printshop in the city and they've done work for me.

I could offer the owner to give him a full set of new menus for a few bucks when I'm on my way to the printshop anyways, and then drop them off the next morning at breakfast. In fact, I'm going to do that tomorrow.

Hey, he might say no. Takes 5 minutes though, maybe I can pick up $20 or $50 out of it. I'm just going to ask, "How much will you pay for 10 new menus, really nice quality?" Will take one menu with me if the number is high enough. The design documents at the print shop for 10 bucks for good quality.

Yeah, a knack for getting money. Skills, drive, work hard, start without thinking too much... but especially kill off your hangups about getting money. You look at people with the knack for getting money, they killed off any hangups about getting money.

I'll drop a line to Judd and 50, if we're lucky if we can get their takes.