Seth Goldstein broke his advice for entrepreneurs down into 140-character bites. 

Seth Goldstein, investor, serial entrepreneur and chairman of Turntable.fm, prefers to tweet his advice. He gave the crowd at KANEKO his top 10 tips for entrepreneurs in under 140 characters — plus this more lengthy challenge to create something different. “I think your ideas should be strange and weird and nonsensical,” Goldstein said. “If everyone agrees with it and thinks it’s a good idea, you’re probably doing something wrong.” Read on to hear the rest of Goldstein’s advice for Big Omaha 2012.

1. Anything worth doing is worth doing badly.

Don’t wait for the right moment or until you know you can do it well. If there’s a market, just do it, Goldstein said. This mindset separates entrepreneurs from entrepreneurial people, and even if you don’t have all the pieces, it’s worth starting. “There’s no putting your toe in the water,” Goldstein said. “You’re already in, you’re swimming, you’re gagging and you realize it’s too late to go back, and that you might as well just keep going.”

2. Leaders believe it before they see it, managers need to see it to believe it.

Goldstein says entrepreneurs know their ideas are good but are surrounded by people who need to see it to believe it. The role of a leader is vision, Goldstein says, and you need to convince people that your vision is inevitable. Managers, even with a different mindset, will help you get there. “We need managers,” he said “because they help us prioritize, they help us focus on what’s important, and they help us execute.”

3. Dress British, think Yiddish.

Or, in other words, look conventional, but think unconventionally. “It makes me smile when I say it,” Goldstein said. “For startups, I think it’s really important to have a good brand.” He also said you can have a great-looking and effective brand without spending a lot of money.

4. Scale a single, social gesture.

Goldstein said that building a social gesture that scales is “the billion-dollar challenge.” The most powerful features and the most desirable companies focus on social gestures — Path, Foursquare, Instagram, etc. Investors look for social ideas that will scale well.

5. Hire slow, fire fast.

“Too often we do the opposite,” Goldstein said. “We hire someone to fill a role so we can focus on the next hole in our team.” He says often we put on beer goggles when hiring, so a ‘B+’ developer looks like an ‘A-,’ but corrodes the work culture and brings the ‘A’ players down to ‘B ‘territory. “The ‘B’s never become ‘A’s,” he said. “They just don’t.”

6. Have difficult conversations.

Goldstein says we avoid tough conversations because they’re hard — but they will never be convenient. “Take a moment and think about the issues that are hard to express,” Goldstein said. “What you want to talk to your partner or your co-founder or your boss or your friend about that hasn’t been easy to bring up. And don’t wait for them.”

7. What is going up and to the right?

Every startup has a metric that’s going up and to the right — and it’s not always number of users. Focus on whatever is growing and use that as the metric to evaluate where you stand. “People are going to judge you no matter what you say,” Goldstein said. “But you have control over how they judge you.’

8. Raise money when you can, not when you have to.

“The number one reason startups fail is because they run out of money,” Goldstein said. But it’s much easier to raise money when you don’t need it. And when the “nuclear winter hits,” you’ll be glad to have a reserve.

9. It’s hard to bring an investor in, it’s 10x harder to get them out.

Investors are important. “We think you just need him or her to write that check for $500,000 or $5 million and all our problems will be solved,” Goldstein said. “But we put on our beer goggles again. We don’t do our diligence.” Make sure an investor is a good fit for your team before bringing them on board.

10. It’s not about the money, it’s about the money.

Goldstein says the decision profitable startups have to make is whether to take the eight-figure exit, or wait for the big, billion dollar-exit — and investors always want you to go for the big one. “We are being fattened like cows by our venture capitalists for the big exit,” he said. But the chances of a billion-dollar exit are slim. Don’t be too proud of a company to sell when the right time comes.

For real-time coverage of Big Omaha on Thursday and Friday, including a live stream of all 14 speakers, visit siliconprairienews.com/live.

Credits: Photo by Malone & Company / Big Omaha.

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