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Welcome back to The Property Management Show podcast, your go-to source for all things property management, entrepreneurship, and marketing. This podcast is proudly brought to you by Fourandhalf, a leading digital marketing agency specializing in property management. Fourandhalf has been instrumental in helping residential property managers generate more leads and attract quality property owners since 2012.

Our hosts Marie Tepman and Brittany Jones recently welcomed Courtney Wolf, founder of RentWise Property Management in Idaho, to their show to discuss Courtney’s journey to successfully creating a hands-off business.

Courtney runs a thriving property management company in Boise that she has gotten to a point of running itself. When asked to expand on the steps she took to make this dream a reality, Courtney shared that it started with big dreams that were broken down into “biteable, doable, and reachable goals.”

She explains that her process involved getting an excellent business coach to hold her accountable and provide guidance, as well as buying in critical team members like her operations manager Carly. Together, they methodically worked backwards from their vision to establish micro-goals that they could tackle over the years to get RentWise to where it is today.

Starting Out Overwhelmed and Doing Everything

Running a property management company is an extremely demanding job. You have to coordinate maintenance, place lockboxes, do showings, answer all phone calls…the list goes on. It’s not uncommon for property managers to experience total overwhelm trying to juggle it all.

Courtney knows exactly what this feels like. When her Idaho-based company first launched, Courtney was a basically one-woman show doing absolutely everything needed to keep things running. Courtney knew something had to change for the business to be sustainable and for her to have any sort of work-life balance.

The Genesis: A Small Business Handling Every Task

Courtney started RentWise property management as the sole employee, handling all aspects completely on her own:

• Placing lockboxes


• Conducting showings


• Checking on maintenance issues

At the same time, her eventual Operations Manager, Carly, would work at the office answering all calls and managing day-to-day relations. The lean team worked hard but constantly felt overwhelmed and overburdened trying to self-manage everything.

The Catalyst: Facing Employee Burnout

Courtney shares the catalyst for taking her business virtual was Carly approaching her, feeling completely burnt out and ready to quit. Carly felt she had no freedom or work-life balance between her full-time job and demands at home.

Facing losing her right-hand employee, Courtney realized if she wanted to retain top talent long-term, she needed to rethink how she structured her business.

Working Backwards to Make the “Hands-Off” Vision a Reality

Courtney’s first step was engaging an experienced business coach. She needed someone who could hold her accountable to goals and break down her big-picture virtual vision into smaller, tactical steps.

Together they mapped out:

The Big Goals

• Create a 100% virtual property management company


• Design systems and processes for complete freedom from day-to-day operations

The Path to Make it Happen

• Determine company values to guide decisions


• Build the right in-house and outsourced team


• Map all processes in extreme detail


• Utilize technology for efficiency

Setting this strategic foundation with her coach gave Courtney clarity and confidence to systematically build her virtual model.

Assembling the Right Team

A key component enabling Courtney’s shift to virtual was curating the right staff across her organization, specifically:

Leadership Buy-In

Getting complete support and dedication from her operations manager Carly was essential. Courtney focused on aligning their individual visions for the business and what lifestyle they wished to create.

Outsourced Support

Courtney offloaded tasks like property inspections and maintenance via her side company Taskmasters. Being able to outsource redundant or specialized work freed her core team to focus on high-level management.

Systemizing Everything Through Detailed Processes

Courtney credits clearly defined processes as central to her eventual hands-off role. Here are the key benefits she experienced from comprehensive documentation:

Enables Delegation

By detailing procedures to a “five-year-old” level of simplicity, Courtney could easily hand off tasks to virtual assistants and Taskmaster employees without extensive training.

Creates Consistency

Highly specific checklists and protocols allowed both in-house and outsourced staff to seamlessly meet expectations and performance standards.

Identifies Improvements

Steps that created bottlenecks or redundancy jumped out clearly when every facet was scripted. Courtney could then refine or automate these areas to fill gaps.

Sets Team Up for Success

With all guidelines compiled in one place, Courtney’s staff always knew the exact requirements for any task or scenario, letting them operate confidently.

Provides Leverage

Once all critical activities were documented, Courtney could remove herself completely from day-to-day operations. Her priorities shifted fully to growth vs putting out fires.

While tedious, Courtney made writing full standard operating procedures foundational before looking to outsource or automate.

Adopting Emerging Technology

In addition to systems and staffing, Courtney credits technology as the third component allowing her to go virtual. When launching RentWise, solutions like self-showing lockboxes and inspection apps were just hitting market.

Being open to trying these emerging platforms (even when they seemed a “hard sell”) meant Courtney’s systems integrated cutting-edge tools from day one for maximum efficiency.

Spawning a Side Business with Taskmasters

In addition to RentWise Property Management, Courtney founded a complementary business called Taskmasters. Taskmasters offers outsourced property management support services tailored to assist busy property managers.

Humble Beginnings

Taskmasters began organically when Courtney realized performing routine site visits herself was an ineffective use of her time and capacity. She started training her existing handyman to conduct inspections to her exact specifications.

Once the handyman demonstrated consistent success inspecting based on Courtney’s guidelines, she considered turning this outsourcing solution into an actual business venture.

Gradual Growth Fueled by Industry Shifts

Initially Courtney deliberately kept Taskmasters small, serving just her inner circle of property manager connections. However, over time as more property management companies embraced outsourcing for supplementary services, interest in Taskmasters picked up.

Seeing tangible results from delegating tedious property visits gave Courtney inspiration that formally offering these type of outsourced field services could benefit numerous property managers facing similar capacity issues that she once did.

While still focused on gradual, organic growth for now, Courtney has bold plans to eventually scale and franchise the Taskmasters model into new markets nationally. Her first-hand experience identifying gaps as a property manager owner enables her to craft solutions uniquely tailored to this industry’s needs.

The Power of Community Connections

At multiple points in the interview, Courtney emphasizes the importance of building strong networks and surrounding yourself with the right community to accelerate success.

Specifically regarding the property management industry, Courtney highlights NARPM as an invaluable network that has facilitated much of her growth and enrichment over the years.

Overcoming Challenges Through Shared Wisdom

Courtney shares that initially she struggled for three years trying to “do things the hard way” before discovering NARPM. Connecting with this network helped her identify solutions already in existence rather than attempting to reinvent wheels.

Having a communi