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What the Founder of Travel Site Trippy Can Teach You About Entrepreneurship

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After two successful exits landed him a fat $85 million paycheck, veteran entrepreneur J.R. Johnson is continuing to hustle and innovate with his latest travel-centric startup: Trippy.


As founder and CEO of Trippy, which pegs itself as the "Pinterest-like social travel planner," Johnson has been able to raise the company's profile through building community, strategic partnerships and landing some notable celebs as investors including Jason Mraz, Tim Ferriss and Rachel Zoe. It's been 12 years since he launched his first company at age 28, but Johnson remembers those early lessons-learned vividly.

Here, Johnson shares some of those lessons, along with advice on how to break through from idea to startup success:

Q: What's the biggest lesson you've learned over the years?

A: There is no substitute for hard work. I don't care how good the idea is, that's less than 10 percent of the battle. The other 90 percent is in the execution and execution takes time. We hear about the YouTubes and the Instagrams which have an exit within a couple years, but from what I've seen any new business is a five- to 10-year project, and that's if it's successful. You can fail much faster, of course. And when you succeed, everyone will think you're an overnight success.

Related: How to Ease Acquisitions from the Acqui-Hired Founders

Q: What's the biggest mistake you see young entrepreneurs making today?

A: Again, it takes a lot of time to build something meaningful. You need to enjoy the process of building something. Many new entrepreneurs are too focused on the exit and not the journey. If you don't enjoy the journey, you won't make the exit.

Q: How do you know when a business idea is worth your time?

A: Ask yourself if you will use the product. I mean really use it. It's easy to always say, "This type of person will LOVE what we are doing and that is our customer." But when you do that, you are making a lot of assumptions. If you wouldn't become your own most-enthusiastic customer, that's when you should look for a new idea.

Related: How to Know When to Start Your Own Business (Infographic)

Q: Any tips for raising money?

A: Be prepared for how time consuming it will be. It's a full-time job in itself, so if you're trying to do it while building the business, something is going to fall through the cracks.

Q: Is having the backing of celebrities important?

A: Depends on the business. For our business, I will say that having advisors is more important that celebrities. They need to be using the product and giving feedback. That's so valuable to us and our advisors are all very engaged and active like that.

Q: What's your advice on building an effective team and going out to market?

A: Find people who want to "eat your own dog food." If your team isn't going to be a customer, it will be difficult to get collaboration from them as you develop new products or iterate on your existing one.

Related: How to Hire the Right Employees for Your Startup

Q: What do you wish you knew then that you know now?

A: It's better to have a team around you. I didn't raise any professional money on my first company. I didn't have an outside board of advisors or directors. Now I'm seeing the importance of surrounding myself with as many smart people that I can find -- and listening to them.

What's the best advice you've heard from veteran entrepreneurs? Let us know in the comments section.

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