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Believe it or not there was a time when Apple did not dominate podcast subscriptions.

In these early days of podcasting there were a bunch of applications that fought to be the first choice app for finding, subscribing to, and reviewing podcasts. Among them was Odeo, a clean and relatively popular app that had all the necessary chops to compete with Cupertino but whose founders could see the threat that the iTunes ecosystem posed to its smaller rivals.

And so the founders gathered the Odeo team together, explained the challenges they were facing, and gave them two weeks to come up with an idea that could keep the company going.

After a day-long brainstorming session the company transformed from Odeo, the ‘just-another-podcast-app’ company, to Twitter, the global social media juggernaut now valued at more than $7 billion.

Odeo’s change of direction from podcasting to Twitter represents one of the most successful pivots in recent years, but it’s far from the only successful pivot. Indeed, some of today’s highest profile companies are the result of substantial pivots early on in the company’s evolution.

The Point, for example, pivoted from socially-conscious fundraising to discount couponing and became Groupon.

Game Neverending pivoted from online gaming to photo storage and sharing, reemerging on the other side as Flickr.

And Burbn was a cluttered, check-in-slash-gaming app before it was slimmed down, began to focus on photos, and became Instagram.

But identifying successful pivots in one thing.

Knowing when to pivot is quite another.

Here are five signs that you should look out for so you can pivot in time to keep your entrepreneurial dream alive.

Your staff are leaving.

You made some great hires early on, your team really gelled, and you started making progress. Everyone was on board and motivated to hit those first targets and the promise of bigger things to come kept your people coming in every day ready to crush it.

“If those same early hires are now spending their lunch breaks browsing Angel List and LinkedIn it’s a sign your original mission is no longer enough to keep people on board,” says DOZ CEO Anji Ismail. “If your staff are thinking about leaving it’s a sign your current direction might need to change.”

The company culture is changing.

When you were getting started the company culture was easy to define. Small team, fast moving, sharing ideas and solving problems together, and everyone knew everyone else. But as your company grew the company culture evolved, too, and now instead of fast-moving free-thinkers you realize you’ve got cubicle drones and clock watchers on your payroll.

HR expert Renee Sylvestre-Williams explains that when you can hire good people but not keep them it could be your corporate culture that’s to blame. What’s more, a changing corporate culture means your original purpose is being diluted – maybe it’s time for a pivot?

You’re making more excuses, more often.

“There’s nothing wrong with the product, it’s the customer.”

“We just need one good month and we’ll be fine.”

“Sales were down again, but it’s a seasonal thing so let’s push through it.”

Sure, any of these could be true. But there’s also a good chance that they are what they sound like: excuses for things not going to plan. If you find that you’re making more and more excuses and if the blame is more often on people who don’t buy your product than the person (you!) who is trying to sell that product, it might be time to reassess and consider a pivot.

Your customers like you, but…

VC and Angel Investor Barry Libert explains that there is a big difference between having your customers ‘like’ you and having your customers ‘love’ you. If you’ve developed a product that people like that’s a great first step, but it might not be enough to compete in a world where brands and businesses succeed when customers ‘love’ their product.

Keep the Odeo/Twitter example in mind here. After all, Odeo was a good podcasting app and had an audience of users who liked it. But could it really compete with the ‘love’ that users felt for iTunes? No – hence the pivot. 

Investors lose their enthusiasm.

Those early meetings with your investors went so well. You were enthusiastic and so were they, and with their support you built the beginnings of a business.

Now, though, things seem to have changed. Meetings are more tense, there are more pointed questions, and your investors are starting to reassess their stake in your business.

Entrepreneur and Convene founder Chris Kenny explains that this is normal and is a chance to pivot. “Create opportunities to earn back your credibility by resetting goals and expectations,” he advises and get those investors back on your side.


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