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Chelsea
Founder & CEO
·
4 mins read

The Mistakes That Nearly Broke Me (And How We Run Things Differently Today)

You couldn’t pay me to work with me 20 years ago. Here's the messy truth behind property management startups.

Almost 20 years ago, I was in the midst of listing and selling mostly REO (Bank Owned) properties, coordinating maintenance, evicting previous owners and navigating asset manager expectations. I thought it would be a simple decision: add property management as a service to our real estate business.

The real estate market had shifted, and my clients couldn’t sell their homes. They trusted me, so when they asked if I could manage their properties as rentals, I said, “Sure, how hard could it be?”

Spoiler: It was hard. Really, really hard.

Looking back, it’s embarrassing how naive I was. I thought I could just tack on property management as a little side gig while running full throttle in the real estate world. I was dealing with banks, asset managers, buyer approvals (or let’s face it, denials) managing distressed properties, navigating reimbursements, price reductions and showings. Approvals took ages, clients cried, my phone rang constantly and cash flow was a nightmare. But, hey, I figured managing a few rentals on top of it couldn’t be that different.

What Could Have Gone Wrong and What I learned

  • Cash Flow Nightmares: The delay between paying for maintenance and waiting for reimbursement from both REO and rentals made cash flow unpredictable. I had moments where the concept of a shell game is the understatement of the year.
  • Legal Landmines: Idaho’s tenant laws? I learned them the hard way. One lease mishap or late repair could have landed us in serious legal trouble.
  • Burnout on a Silver Platter: I was the owner, the accountant, the maintenance coordinator, and, let’s be real, probably the one relighting the furnace after convincing the gas company to leave the service on because I couldn’t meet them on time. The lack of boundaries was brutal.
  • System Chaos: Everything was manual. I’d lose track of maintenance requests, forget to follow up with tenants, and scramble to keep things straight. There were limited software systems, and a lot of sticky notes and prayers.
  • Vendor Management Madness: Some were great, some were awful. Learning the difference on the fly in the middle of the night is not my idea of a good time.

What We Do Now That We Didn’t Then

These days, Urban City Property Management is a well-oiled machine. We’ve learned—sometimes painfully—how to build a property management company that not only survives, but thrives:

  • Pro Systems & Processes: From tenant screening to maintenance, we have documented, automated systems that ensure nothing slips through the cracks.
  • Financial Mastery: We use advanced property management software that tracks every dollar, keeps our clients informed, and ensures consistent cash flow—even when some reimbursements take time.
  • Clear Roles & Responsibilities: We’ve built departments so that everyone can specialize and our team of professionals handle their roles with precision.
  • Compliance First: We stay on top of Idaho’s ever-changing rental laws, keeping our clients and tenants protected and mastered the art and science of negotiation. Fortunately, we’ve always been able to negotiate rather than evict in our company saving legal and damage expenses.
  • Vendor Partnerships: We’ve developed strong relationships with trusted vendors, who give us exceptional service and terms, ensuring maintenance is handled efficiently and cost-effectively.

Looking back, I realize how lucky we were. I also see the power of persistence, grit, and being willing to learn from mistakes. The reality is, I wouldn’t trade those early struggles for anything, but if given the choice as a real estate investor today, you couldn’t pay me to work with myself back then.

We’ve been through the fire, refined our processes, and come out the other side as one of Boise’s best property management companies. And we couldn’t be more grateful.

I don’t ever forget how close we came or how hard it was and that’s why we do what we do, with passion, precision, and a lot of hard-earned wisdom.

P.S. For those of you who have been with me since the early days, I thank you so much for your continued trust and perseverance right along side me.