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Jason Goldberg, who co-founded the online recruiting startup Jobster in 2003, was one of the more colorful characters in Seattle’s startup community. I always got a kick out of interviewing the brash, upfront and (some may say arrogant) CEO of the heavily-funded startup, and to this day I still remember losing a very competitive ping-pong match to the entrepreneur at the company’s offices along the Seattle waterfront.

Goldberg is now in New York, running a daily deal site called which he tells GeekWire is absolutely “crushing it.”  The 39-year-old former T-Mobile manager and White House aide in the Clinton administration was just interviewed by Digg founder Kevin Rose, telling some great stories about the early days of Jobster. (The portion of the video below starts in minute six).

“It was a good idea before its time. It was before LinkedIn, before Facebook,” said Goldberg, adding that it proved to be a solid education for a first-time entrepreneur.

“I made every mistake in the book,” said Goldberg, who burned through $48 million at the helm of Jobster. “I … basically got educated on that $48 million on how to start companies.”

He continued:

“One of the biggest things I learned was the importance of the product. Everything is about the product. The thing that I look back on my Jobster days, and I said I would never repeat again was, on day two of Jobster I was no longer the product manager. I was kind of this general manager/CEO. And it just killed me ever since then that I wasn’t able to kind of manage what was actually going to be our product, our user experience. And the focus was on building the team, building sales and all of this stuff…. I said that I would never do that again. Product is my passion, and the user experience I think, especially in a Web-based business …, it is all about what is the product that I am interfacing with. And it really became this thing where I think the CEO needs to own the product, and put their personal touch on the product, much like say Steve Jobs does.”

Goldberg also takes some time to explain what it was like raising capital from Ignition Partners and working with former Microsoft employees. In 2003, he said that no one was investing in consumer Internet companies, but Ignition saw something special in his idea.

“(Ignition) heard about the idea and they said: ‘we will do whatever we can for you to not to take this to the (Silicon) Valley. We want you to build this in Seattle. We are all about building Seattle companies.’ And they believed in me, and … they gave me what was the equivalent of seed money…. But also I was pretty naive at the time. I didn’t know what I was doing. I didn’t know anything about how to bring founding teams together, so they brought my founders to me. And they were all a bunch of Microsoft guys. And they married me with these Microsoft developers, and said let’s go build this product….

There was this naive, nervousness about building a first company, and I was like, ‘alright, let’s do it.’ And they are all good people. It was just the little things that you have to get right from the beginning that we didn’t. But one of the lessons learned was, obviously pick your founders really carefully…. You need to have a good conceptual sense of what you want to do, or at least an understanding (on) your team of how you are going to figure that out together. Whereas, we were just kind of like: I had an idea, social networking for recruitment. Put 10 guys in a room and let’s see what happens. I didn’t know at that time how to lead that.

But one of the other lessons that I learned from that was that we hired a development team, and it was like 12 guys out of Microsoft. And we basically built product the Microsoft way back in 2004 which is that we spent a year building the first version of the product, and then shipped it to our customers. And, ahead of shipping it, we signed an ungodly number of customers in a conceptual phase. It was like 1,000 customers signed up, enterprise companies to use our product before we ever launched. Invariably, you spend a year to build something and then you spend six months getting customer feedback, the cycle was just too long. Right? Meanwhile, during that year that we were building LinkedIn took off or started and at the same time Facebook was being incubated and all of this sorts of stuff. And it was just the way of building it was just (too slow). We also got way  too caught up in sales. One thing I learned was, obviously you need sales to drive revenue, but have a great product first. We sold 1,000 companies on something that we just couldn’t deliver on.”

Absolutely fascinating stuff. The interview continues with more nuggets, including why he built his next company to be the “anti-Jobster.”

Love him or hate him, one thing about Goldberg is that he talks openly about his experiences. He also assembled a pretty deep bench at Jobster. Many of its alumni have gone on to start their own companies, including Feedjit’s Mark Maunder, Urbanspoon’s Patrick O’Donnell, Ethan Lowry and Adam Doppelt; Bacon Salt’s Dave Lefkow and Justin Esch; Valuevine’s Neil Crist; and RescueTime’s Tony Wright and Brian Fioca.

After watching the video, I asked Goldberg today whether he missed anything about his time at Jobster,

“Learned a lot from it, but no, don’t miss it,” he said. “Each experience builds on the ones prior.”

Here’s the full 37-minute interview:

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