A couple of weeks ago, I had the chance to interview a long-time Chicago bootstrapper, Ryan Coon founder of Rentalutions.  Ryan was very candid about his lessons learned and I appreciate his willingness to share and help others.

Theresa: Please tell us briefly about yourself?

Ryan: I have always been an entrepreneur at heart, but after undergrad I worked at an investment bank for about three and a half years. I got tired of the corporate world and talked to my co-founder, who’s a great friend from undergrad, and we decided to start Rentalutions. Rentalutions is the one go-to place for landlords and property managers to efficiently manage their rental units.

We launched our private beta about three weeks ago and we’re getting ready to launch our public beta in about two weeks.

Talking to small property owners we saw the lack of one resource that helps them throughout the entire rental cycle.  Rentalutions helps users find and screen tenants, create custom lease agreements, manage security deposits, collect rent, track maintenance requests and prepare financial reports.

Theresa:  Can you share a couple lessons learned?

Ryan:  One is that, to be successful, I think that you’ve got to be able and be willing to step outside your comfort zone.  I think that a lot of what we do as founders and as Bootstrappers doesn’t necessarily come naturally, but to be successful you’ve got to be willing to do whatever it takes.

Another big lesson is that there are so many resources available, and you’ve got to be able to synthesize how you’re going to spend your time and recognize the resources that make sense to take advantage of.  I think Bootstrappers Breakfast is something that has been invaluable for me.

Every day founders are forced to make decisions about which resources make sense to utilize. In the early days, it is more about how you spend your time. You must be able to prioritize and recognize that you’re going to have a never-ending to-do list, but that you’ve got to spend what precious time you have on the top three or top five things that really truly matter.

Theresa:  What was the biggest surprise?

Ryan:  As I mentioned earlier, it’s been just how much there is to do.  Another big surprise was the importance of a co-founder; I can’t imagine doing it alone. I looked in my personal network and said who can I trust and who’s going to work just as hard as me, and found one of my good friends. Laurence and I share the same passion for starting a business.

Theresa:  Can you think about one key assumption that you made that turned out to be incorrect and really caused you a lot of grief?

Ryan:  Most entrepreneurs start businesses thinking that they understand exactly what product makes sense and will sell. We realized quickly that this is not the case and adopted the ready, fire, aim mentality. This meant we could get the product in users’ hands a lot quicker than we initially expected.  The truth is that no matter what, there is always going to be refinement and iteration. One release of the product is never going to be perfect.  Once you realize that, you can move on and say, all right, I’m going to get a product out in the marketplace and make changes later. Since we are willing and open to accepting early feedback, actually getting a product out there was easier than I expected.

Initially, our product was in response to listening to friends and family who own rental properties voice the constant pain that they have with managing those properties efficiently. As we spoke to more property owners with fewer than 100 units, we discovered a lack of property management tools that addressed their needs at affordable price points. For large property owners, there are enterprise level solutions that exist. They have all the bells and whistles, but also come with an enormous price tag.  We felt like there was an underserved market that wanted to replace Excel spreadsheets with a better solution. We thought we could fix that. But rather than take the Steve Jobs approach of telling people what they wanted, we listened to our customers. I don’t think we’re smart enough to tell people what they want and what they should rush out and stand in line to buy. So in response to customer feedback, we developed our initial product.

Theresa: I know you and your partner are business background rather than a technical background. Do you have any advise to others in a similar situation, as far as dealing with technical help?

Ryan:    Our focus has been, “We’ve got a business issue that we need to fix.  We can bring in technical help.” We also bring a general openness to learning. One critical piece of advice is that it’s important to love your developer and appreciate them. We have a great team that is willing to help us. It’s important to find people who will work with you. Sometimes things you want to do just don’t make sense from a programming perspective.  Occasionally we must be willing to pivot and to do things slightly differently than we would normally do them.

Theresa:  Thank you for your time and good luck as you follow your passion.  It is clear that you love what you do.