Personally the first Startup Grind event I ever attended, complete with Cash Money Records music, free pizza, and great networking. I was lucky enough to see one of the legendary VCs from Silicon Valley, Jeff Clavier. Throughout this interview he goes over a variety of topics any entrepreneur will still find valuable today such as how to get a meeting with SoftTech VC, how to perfect your pitch, and what NOT to do when trying to get a VCs attention.

[00:00:05.20] QUESTION: What about this thing right now, are you seeing, there’s been a lot of talk of, that just there’s all these companies that were funded at the angel level, they’re now coming in for a series A, not able to get that funding. Are you seeing that with your companies that you’re having, or not you specifically but companies in general, that is this a real trend that’s happening that companies raised angel round are now struggling to raise series A, maybe because they shouldn’t have deserved an angel round or some other reason?

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One of the first big interviews Startup Grind ever hosted was with Jason Calacanis. Jason was kind enough to take time out of his busy schedule during his meetings in Palo Alto to come and speak  to small intimate group at the Startup grind offices. Watch and learn more about Jason’s early entrepreneurial ventures during Web 1.0, what catches his eye in an entrepreneur and how to perfect your pitch.

[00:02] DEREK: On that note, let me introduce Jason; he needs no introduction, he’s worldwide.

[00:08] JASON: I’d like one.

[00:09] DEREK: Well then let me give it.

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In one of the earliest Startup Grind interviews, David Cowan from Bessemer Venture Partners joined us to discuss a variety of things going on in Silicon Valley. From what VCs are really looking for, seeing potential in the right entrepreneurs, and being on the board of one of the most successful app developer, Smule.

[02:34] DAVID: OK. I didn’t mean to get involved in the technology industry, it was an accident. I loved computer science and studied it in college. I had some friends that worked with me in the Science Center and we were called Terminal Watchers. They told me when I graduated that I had to interview with a company called Oracle. I didn’t know what it was or care, I was all set to get a job at some investment bank or management consulting firm; that was more glamorous back then. My friends urged me to go to the interview so I did. Back then, Oracle was hiring like crazy and didn’t know who I was, just that I was a computer science major.

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Our Dave McClure interview is easily one of the most memorable Startup Grind interviews ever. Dave came to the stage and talked about everything from farting unicorns to expanding out to international cities with 500 Startups. Watch and learn how to get the right VC’s attention, expand into new markets, build a great product, and get a meeting with the pirate VC himself.

[00:01:22.08] QUESTION: Welcome to the Startup Grind. We like to start these things out by just getting to know you a little bit, hear about your background. Tell us a little bit about where you grew up tell us about –

[00:01:30.26] DAVE: I know I’m really hard to find on the web, so it’s all a big secret.

[00:01:37.25] QUESTION: We’re going to dive deep, man, we got handkerchiefs, we got everything. We expect the tears to flow. So, tell us about West Virginia, tell us about your family and tell us all about it.

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