Francis Adanza e-mailed this interview in today. Ryan Gilbert will be joining us at a future Bootstrapper Breakfast to talk about his experiences in more detail.

Today, I was able to sit down with Ryan Gilbert, a serial entrepreneur who is most recently recognized for taking his company PropertyBridge from idea to exit. PropertyBridge is the leading provider of electronic payments for property managers and real estate owners in the multifamily housing industry. PropertyBridge was founded in 2003 and acquired by MoneyGram International in 2007.

As a entrepreneur and member of the Bootstrappers Breakfast, I thought the group might benefit from Ryan’s lessons learned. In addition to this blog, Ryan will be joining the round table discussion as a featured guest speaker on Friday, May 22nd at the Bootstrappers Breakfast in Mountain View. Come join us, engage in serious conversation, and ask Ryan your own questions.

Below is a short Q&A conversation where Ryan’s shared his PropertyBridge experience with me.

Q: Was PropertyBridge your first entrepreneurial endeavor?

No, my first startup was Orange Technologies, which I founded in South Africa. We acquired licenses from US software companies to resell their products in South Africa. It was through these vendor relationships that helped me develop a track record of success with US based corporations. Eventually, Orange Technologies was acquired by our largest vendor, allowing me to relocate to the United States. In total, I have been through five startups.

Q: How did you come up with the idea of PropertyBridge?

At the time, I was working for Wells Fargo in a business development role. I noticed that banks only offered horizontal solutions to vertical problems. Each vertical market had its own specific needs and feature sets. For example, integration with accounting systems, special reporting for enforcing legal rules/policies, and banking requirements. The need was clear, and it was a question of which vertical market to attack. The property management industry collects over $147 billion in residential rent payment every year, and most payments are made by check–the market was ripe for electronic payments.

Q: How many co-founders did you have? How did you find your partners?

We had a five person founding team. Each founder contributed a mix of capital; money, time, expertise, and resources. The partners knew each other from previous start-ups or socially. I fundamentally believe that the success of a company depends on how well the founding team can communicate, compromise, and work together. It can be very challenging to start a business with folks you are working with for the first time.

Q: What advice would you give to others, so that they can avoid any of the challenges you encountered in your experiences? Any words of wisdom, tips, gotchas?

PropertyBridge’s biggest challenge was speed and revenue. Since our revenue was generated by taking a fraction of a percent per transaction, it was critical that we acquired thousands of customers quickly. We focused on marketing and end-user adoption programs to ensure that as many potential renters as possible chose to pay their rent through PropertyBridge.

My top five tips include:

  1. Truly understand the problem and the market. Make sure you know who your customers are and how they buy.
  2. Don’t wait until the product is perfect. Get out there and sell.
  3. Find, motivate, and compensate good people. The power of good ideas is nothing without people who can actually execute them.
  4. Take VC funding when you get the chance. Unless you can truly afford to go without it, when someone makes you an offer, take it.
  5. Be decisive and look ahead.