These entrepreneurs are on Business No. 3 - at least

• Name: Polina Raygorodskaya, 26
• Current business: Co-founder and CEO of Wanderu, Boston
• Successful companies: 3

I started my first company, Polina Fashion, as a sophomore in college, it was a beauty and fashion public relations firm. I ran that business for seven years, and only stopped when I started my third company, Wanderu, a travel site that coordinates bus and train travel.

In between I also started Boutique Week, a company that organized semi-annual discounted sales at boutique stores across the country. It was definitely my biggest failure, but I also learned so much. I had bootstrapped Polina Fashion 100% and that's what I thought we would do with Boutique Week.

We grew really quickly; we had 100 boutiques participating in four cities and just two of us doing the work. We needed more people and more resources. At the same the time my partner and I weren't getting along, our personalities didn't mix.

After two seasons we decided to separate and shut the business down. When I started Wanderu, my new business partner and I bootstrapped the prototype and we were working with no salary because we believed in the product.

Related: What I gave up to start my business

But we also knew that we needed funding to grow as quickly as we wanted. Our initial funding helped us hire the rest of our team, there's now eight of working full-time and four part-time. We're still in our beta phase, which is just covering the Northeast, but we plan to be in the U.S., Mexico and Canada by the end of the year.

NEXT: Best advice: Keep money in the company