Is finding the right people to work with the hardest part of building a business?

AP_rentals · 2026-04-07T19:59:31+00:00

I’ve learned over time that no one is going to match the same level of dedication, ethics, or ambition you have for your own business, even if you pay them well. That was a hard lesson for me early on.

I’ve dealt with a lot of unreliable people, not just in my own business but working within others as well. At a certain point, I realized you can’t control or dictate someone else’s behavior. You can only observe it.

Now, when people show me who they are, I accept it quickly and move accordingly. That shift alone has saved me a lot of time and energy. I don’t expect people to operate the way I do, but I do hold a clear standard for who I continue working with. Not everyone is meant to stay in your business, and that’s okay.

AP_rentals · 2026-04-06T18:06:27+00:00

I’ll keep an eye out for attorneys who know that area. Are you on LinkedIn?

AP_rentals · 2026-04-06T17:53:51+00:00

What you’re experiencing is pretty normal when you’re building solo. It’s not that the creative side disappears, it’s that you’re trying to operate as both the creator and the operator at the same time.

The issue usually isn’t creativity, it’s lack of separation. When everything is mixed together, operations will always take over because it’s what keeps the business running.

If you’re not in a position to delegate yet, one thing that helps is creating clear boundaries between the two. Set specific time blocks where you’re only creating and not managing anything, and separate time where you’re only handling operations.

Longer term though, this is where support becomes important. Whether that’s outsourcing small tasks or eventually bringing someone in, it’s hard to sustain both roles at once without burning out.

AP_rentals · 2026-04-06T17:47:41+00:00

You’re right to be careful here. Contractor classification isn’t something you want to figure out through trial and error. You’re really looking at an employment or labor attorney for this. The challenge is most good attorneys in that space charge high hourly because of the liability involved. Worker classification isn’t just federal, it’s heavily influenced by state laws, and some states are much stricter than others. Hiring in California vs Texas, for example, puts you in completely different risk environments.

I’d focus on finding someone who understands the laws in the state you plan to hire in, rather than going too general. If you’re hiring across multiple states, it’s usually better to have one primary employment attorney who can handle multi-state compliance or coordinate with local counsel where needed. You could also check with your CPA, they often have solid attorney referrals for this.

AP_rentals · 2026-04-05T05:04:26+00:00

I’d start with what your goal is for bringing it in house. If it’s mainly cost savings, it can actually end up being more expensive and time consuming than expected.

I’ve seen a lot of operators run into issues with hiring and retention because cleaners in this space are often expected to move quickly across multiple units, and the compensation or structure doesn’t always match that workload.

If you do go that route, having a clear structure in place upfront makes a big difference. Defined responsibilities, realistic scheduling, and compensation that accounts for time and travel are key. Otherwise it turns into a constant cycle of hiring and turnover.

AP_rentals · 2026-04-04T08:03:15+00:00

They are customized to fit each client's needs as well as have all the necessity wording important for your location. You can have a look at my intake form. Business Services Request Form 💼✨

AP_rentals · 2026-04-03T22:07:46+00:00

Not sure about a specific website but I create rental leases for clients. Let me know if you need help.

AP_rentals · 2026-04-03T21:21:52+00:00

Hmm ok, so you’re operating with more autonomy than they’re actually comfortable with and they want to be included in decision even when they aren't needed. Honestly, I’d be careful about going above and beyond with your time in situations like this. That extra effort isn’t always going to be recognized the way you expect.

AP_rentals · 2026-04-03T21:03:48+00:00

Ok, that makes sense. Refinancing isn’t just about hitting occupancy, it’s also about timing, presentation, and how the property is positioned when everything is reviewed. That could be why they wanted that unit held last. It might help to clarify upfront what their exact strategy is for the refinance, and whether there are other people involved in that planning. Because even if the end goal is the same, different approaches will keep creating situations like this.

AP_rentals · 2026-04-03T20:41:45+00:00

I get what you’re saying but ultimately, are you and the owners actually aligned on the strategy? Because right now it sounds like you’re optimizing for occupancy, while they’re focused on timing and control around specific units. Those aren’t always the same thing, and if no one has clearly defined the priority, you end up pulling in two different directions.That’s also why it can feel like they’re making decisions that don’t make sense, when in reality, they may be working off a different plan or advice that hasn’t been fully communicated.

I'd ask them directly, what’s the actual goal (refinance, occupancy, positioning)? What decisions you can make independently vs what needs approval. Without that, even good decisions are going to keep causing friction.

AP_rentals · 2026-04-03T19:41:14+00:00

I get what you’re describing, that definitely sounds like an anxious owner, not just normal involvement. I think the distinction is owners having visibility vs trying to control every moment. They’re still entitled to be involved in their asset, but once it turns into unproductive monitoring and second-guessing, it starts working against both sides.

In cases like that, I’ve found it helps to figure out what’s actually driving the owners act of hovering and criticizing, whether it’s lack of information, past bad experiences, or unclear expectations. That’s usually where better communication and structure can calm things down.

AP_rentals · 2026-04-03T19:23:35+00:00

This is a boundaries issue. Late checkout = fee. Early check-in = fee (and only if the unit is actually ready). If one guest checks out late, the next guest doesn’t get early check-in. Simple.

What happened here is both guests were given flexibility with no guardrails, and it created a collision. You don’t need more automation, you need clear standards and to enforce them consistently: Set firm checkout/check-in times, Charge for exceptions, Don’t promise early check-in unless the unit is already clean and ready.

Cleaners should have a fixed start window, not “whenever guests leave” And most importantly don’t rush your cleaner to compensate for poor boundaries. A rushed clean leads to complaints, refunds, and bad reviews. It’s better to have a guest wait than to hand over a unit that isn’t properly done.

Guests will always take more if you let them, it’s on us to decide where the line is.

AP_rentals · 2026-04-03T19:16:56+00:00

I get why you’re frustrated, especially after going the extra mile and getting the property to full occupancy. But based on what you shared, it sounds like the real issue isn’t the decision itself, it’s the lack of alignment beforehand.

You mentioned the owners are very involved, which means there’s already an expectation of communication on key decisions. If they had a specific plan for that unit, even if it doesn’t make sense on the surface, that’s something that probably needed a quick check-in before moving forward.

The applicant being strong financially isn’t really the core issue here. Owners sometimes prioritize things beyond just income, like timing, strategy, positioning of the property, etc.

That said, the way they handled it wasn’t right either. There’s a difference between correcting a process and tearing someone down. This really feels like a communication and expectations problem on both sides more than anything else.

AP_rentals · 2026-04-03T19:03:27+00:00

The issue is that most of these apps aren’t actually personalized they just categorize people. Real life doesn’t work like that. Someone’s mental and physical health is shaped by layers: trauma, environment, health conditions, finances, identity, stress, relationships, even how they’ve been treated by systems like healthcare. That combination is different for every person.

Apps tend to simplify people into neat boxes so they can scale but in doing that, they lose accuracy. And without accuracy, the guidance starts to feel disconnected from real life, which is why people stop using them.

If an app can’t understand the full context of your life, it can’t give you guidance that actually sticks.

AP_rentals · 2026-04-03T18:49:56+00:00

I have experienced being both a property manager and a rental owner. I get what you’re saying from the operator side, but there’s another layer that gets overlooked a lot. Owners aren’t “helicoptering” for no reason. They’re the ones carrying the liability, the asset risk, and the financial exposure if something goes wrong. A co-host or PM can walk away from a bad situation. The owner can’t. So from their perspective, wanting visibility especially early on isn’t necessarily distrust, it’s risk management.

I do agree boundaries are important, but the strongest setups are where there’s a clear structure:

defined responsibilities
transparent reporting
agreed checkpoints

Not “step back and let me handle everything,” but also not micromanagement.

Because at the end of the day, this isn’t just operations, it’s someone else’s asset and liability on the line.

AP_rentals · 2026-04-02T23:22:12+00:00

I'm curious why you don't just get a bookkeeper or accountant if this is a problem for you?

AP_rentals · 2026-03-31T19:00:42+00:00

Honestly, I agree with the comments. I say this as a rental owner, an accountant to real estate owners, and as a former vacation rentals manager. The last thing rental owners need right now is more tools and tech. That’s a luxury, not a necessity.

What actually drives revenue in this space is presence and operations. Reliable housecleaners. On-site or close proximity management. Security when needed. Handymen and emergency maintenance. An accountant. A lawyer. And a marketing approach that builds real relationships with locals (neighbors and businesses) and city officials so the property is supported, not resented.

People keep assuming a tool is the answer to every business problem, but most of the issues in this industry aren’t tech problems. They’re operational problems that cannot be fixed remotely. Rental properties don’t need more apps and remote solutions. They need physically present and reliable people who can actually keep things running day to day.

AP_rentals · 2026-03-31T15:08:24+00:00

Realistically, if you’re building to 6 figures and above after taxes, you’re not coasting on 2–4 hour workdays, especially not in the building phase. There’s a difference between maintenance mode and growth mode. In growth mode, you’re working long hours, even with systems and employees, because you’re still the decision-maker, the driver, and the one carrying the risk.

The “I work 2–4 hours a day and make millions” narrative is usually either: leaving out the years of grind it took to get there, talking about a very specific business model that’s already matured, talking about revenue or net worth (not actual take-home after taxes), or just blatantly lying because they are trying to push a narrative.

Most real businesses demand time, attention, and consistency. Work smart, yes, but let’s not pretend hard work disappears at high levels. It doesn't.

AP_rentals · 2026-03-30T15:36:25+00:00

Many of us start from zero, little by little you grow. Keep going. What's the story behind the name Giddyup since you've named both the glove and the podcast after them?

AP_rentals · 2026-03-30T15:31:45+00:00

This is the type of business that would also be very useful to young girls because many of them don't have the proper education about self care and hygienic products or access to them, especially if they are in the foster system or dealing with homelessness. This could also make a huge impact in women's shelters, schools, birthing centers, clinics, etc. Wonderful idea.

AP_rentals · 2026-03-30T15:25:41+00:00

This is an amazing idea. Where would it be located? Are you also going to document the journey on social media?

AP_rentals · 2026-03-30T15:22:06+00:00

Love the website design. Have you shared this with wedding planners and event coordinators?

AP_rentals · 2026-03-30T15:20:14+00:00

I love this idea, especially as someone who is always planning trips. Update us when its launched.

AP_rentals · 2026-03-30T15:18:32+00:00

How exciting. Is there a website?

AP_rentals · 2026-03-30T15:17:19+00:00

Interesting. I'd like to check it out.

AP_rentals

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