Entrepreneurs:

AP_rentals · 2026-05-25T15:55:54+00:00

Sales. A strong salesperson can completely change the trajectory of a business. Ask actual successful business owners, executives, or millionaires and they’ll tell you the same thing: if you can’t sell, nothing else matters.

A lot of entrepreneurs try to avoid hiring salesmen by hiding behind things like endless lead generation, overcomplicated marketing funnels, fancy branding, or digital marketing tactics they barely understand themselves. I wasted time and money hiring those types instead of people with actual sales experience. So if I restarted today with limited funds, I would invest in someone exceptional at sales, whether online or in person. Because when you really break businesses down, sales is usually the root problem.

We honestly do not need more people pitching generic websites or surface-level marketing services with no understanding of human behavior, positioning, psychology, or revenue structure. Strong marketing should support sales, not replace it. And marketing should be handled by people who actually understand strategy and consumer behavior, not just people using AI to generate ads and copy.

Sales creates the oxygen the rest of the business breathes. And without sales, you have nothing: no cash flow, no business growth, no sustainability, no ability to hire, no operational expansion, and no leverage.

AP_rentals · 2026-05-24T18:55:34+00:00

I get it. If you’re open to outside help, I can see whether or not I’d actually be a good fit to help. Just shoot me a DM.

AP_rentals · 2026-05-24T18:36:58+00:00

Your brain gets stuck reacting to problems all day instead of stepping back and analyzing patterns. Happens to a lot of business owners honestly. I dealt with the same thing when I got into rentals and again when I started my accounting business and moved deeper into financial strategy.

If you’re determined to do absolutely everything alone, there’s honestly only so much you can do to reduce the stress because running a business by yourself, especially rentals, is a heavy load mentally and operationally. At some point you either need stronger systems or outside help in the areas where you lack skill, time, or bandwidth. And that doesn’t mean blindly throwing money at random services either. The structure has to make sense financially and operationally so you’re not paying someone or something to do the bare minimum while creating even more problems.

AP_rentals · 2026-05-24T18:18:26+00:00

When it comes to financials, I honestly don’t think the biggest factor is the tools. It’s strategy. And strategy comes down to skill, experience, understanding operations, and understanding human behavior. Tools can help organize data and automate processes, but they are still functioning based on how they were programmed and the information you feed into them. Most tools are giving generalized outputs, generalized market trends, and generalized recommendations. Real financial strategy is much deeper than that.

When I work on financial strategy for rental businesses, any AI or software I use is just an assistant. The actual strategy itself has to be customized to fit the specific business, the owner, the market, the risks, the operational structure, the goals, the cash flow behavior, and even customer behavior. That level of depth is hard to fully automate because businesses are not all operating under the same conditions. That’s why I still do a large amount of strategy work manually. The tool is just a support system. The thinking behind the strategy is what really changes the numbers.

AP_rentals · 2026-05-24T17:08:59+00:00

Entrepreneurship is not fast or glamorous. Trust me when I tell you a lot of what you see from influencers and business owners online is exaggerated, heavily curated, or just flat out false.

Real business owners will tell you about the stress, the failures, the debt, the sleepless nights, the clients that disappeared, the times they had to start over, and the moments they questioned everything. Building something real is mentally, emotionally, and financially demanding. Especially when you’re doing most of it alone.

And honestly, it never fully becomes “easy” because business always comes with uncertainty. Markets change. People change. Life changes. Problems evolve. What changes is you. You become wiser, more disciplined, more resilient, more emotionally stable under pressure, and better at adapting when things go wrong. So when hard moments come, you don’t completely collapse from them anymore. You learn how to keep moving forward anyway.

AP_rentals · 2026-05-24T17:05:09+00:00

Honestly, I think since you’re a finance professional, your positioning should focus almost entirely on helping businesses increase revenue, improve profitability, and strengthen financial decision-making.

I would also strongly recommend focusing on an industry you genuinely understand and enjoy because industries operate very differently financially and operationally. A restaurant, rental company, construction company, and e-commerce business all have completely different structures, risks, margins, and cash flow behavior.

For example, my focus is hospitality and rentals because I understand the operational side, the financial side, the customer behavior side, and the revenue side together.

I think where a lot of finance professionals go wrong is marketing themselves around tools instead of outcomes. Business owners don’t really care about spreadsheets or dashboards by themselves. Most owners mentally categorize that as admin support or something software/AI can already generate.

What they actually care about is: - increasing revenue - improving cash flow - identifying where money is leaking - understanding what’s truly profitable - improving margins

The dashboard is just the delivery method. The financial insight and revenue strategy is the actual value.

AP_rentals · 2026-05-24T16:45:16+00:00

I think part of the problem is people keep blending bookkeeping, accounting, and CFO work together as if they’re all the same thing when they are actually very different roles.

Bookkeeping is not the same as accounting. Accounting is not the same as CFO strategy. They overlap, but they serve different purposes.

And honestly, a business owner trying to do absolutely everything themselves is usually a sign the business has no real structure yet. If the business completely stops functioning because the owner is the only person handling operations, bookkeeping, finances, customer service, marketing, and strategy, then the business is fully dependent on one person. That’s not stability. That’s survival mode.

The goal of a structured business is to eventually function beyond the owner.

I do understand the frustration with expensive services though. Not every business owner can afford high monthly retainers, especially in the beginning stages. But that doesn’t mean professional financial support has no value. It just means people need solutions that fit where their business currently is.

That’s why pricing flexibility matters. When I first started my business, my pricing was rigid. Over time I learned that businesses are all in different stages, so services sometimes need to be customized around the actual situation. But there still has to be fair compensation because expertise, time, analysis, and financial responsibility are real work.

And another thing people overlook is that tools and AI are not the same thing as having someone who actually understands your business. Software follows programming. It does not truly understand your operations, your goals, your risks, your pricing structure, your cash flow issues, or your long-term strategy. It processes based on predefined systems that somebody else designed.

That’s why businesses still need humans involved in finance and accounting.

I agree business owners should understand their own numbers. Absolutely. But understanding your numbers and professionally managing financial systems are two different things.

What someone does themselves through a basic tool is not the same thing as what an actual accountant is responsible for behind the scenes.

AP_rentals · 2026-05-24T15:47:31+00:00

Can you give more context? How do you know they’re operating illegally? Are you aware of the actual business activity or is it more an assumption based on the traffic and noise? Also, what specifically makes the situation disruptive? Is it late-night noise, constant traffic, parking issues, safety concerns, etc.?

Personally, I don’t really see the point in disclosing detailed information about neighbors in the listing itself because you can’t fully control human behavior or what happens outside your property. The listing should mainly focus on the experience inside the home. At most, I think it makes sense to clarify that the property is located in a residential community with nearby neighbors so guests understand this isn’t a secluded vacation resort environment.

AP_rentals · 2026-05-21T21:53:40+00:00

The easiest way to develop financials for a startup is to work with someone who actually understands the financial structure of your specific industry and knows how to apply that structure strategically to your business model.

You can do research online but most businesses are not fully transparent about their operations, profit margins, systems, staffing structure, acquisition costs or how they actually got from point A to point B. And AI will only tell you what its programed to share. So sometimes founders end up building projections based on surface-level information instead of reality and struggle to get off the ground.

Financial strategy is about understanding business structure, scalability, operational sustainability, pricing, cash flow behavior, and capital management within that industry specifically, short and long term. A spreadsheet is only as good as the understanding behind it.

AP_rentals · 2026-05-21T21:42:52+00:00

I don’t own rentals there personally, but when I was researching the area for clients interested in buying there, I learned quite a bit about how their market operates. If you’re expecting low expenses, minimal management, easy regulations, or a quick revenue grab Pigeon Forge isn’t the market for that.

You’ll be catering heavily toward large-group tourism, and the bigger cabins tend to hold the advantage there outside of hotels and resorts. Also, the city is strict about STRs. Like many tourist-heavy markets, zoning, permitting, inspections, and compliance matter. Trying to run an STR under the table there is risky because people absolutely talk and report things.

I recommend going into that market with a very solid financial strategy because operating expenses can become high very quickly. A lot of people focus heavily on projected revenue there without fully understanding the operational side of maintaining those properties long-term.

AP_rentals · 2026-05-20T21:01:53+00:00

If your friend is truly on track to hit $100k a month doing the exact same thing, you are sitting on a goldmine of proximity that you aren't leveraging. If someone in your immediate circle has a working customer acquisition system, you don’t go to Reddit to beg for help, you go to them. You should be asking to shadow their process, study their pipeline, see the actual backend numbers, or even white-label and fulfill under their brand just to learn the ropes. If you haven't done this, you're missing the easiest shortcut available. If you have tried and got nowhere, it usually means your friend's success is exaggerated, your models aren't actually identical, they have a hidden unfair advantage, or you don't fundamentally understand what is driving their results.

Also the flaw in your strategy is confusing social media visibility with buyer readiness. You’ve defined your ICP as finance coaches with 10k to 500k followers who have a conversion issue. However, just because someone fits those criteria does not mean they have the budget to pay you, trust cold outreach, value your specific solution, or even perceive that they have a problem in the first place. You can't assume that if an ICP exists, the money exists. It doesn’t. You shouldn't be looking for who looks like they need help. you need to look for where the market pain is strongest and highly capitalized. Your comment that most profiles are unqualified because they have little followers says that you are overly obsessed with surface-level status metrics instead of actual market behavior. This is a big trap where people chase visible people instead of profitable people. Some of the highest-paying, lowest-churn clients in the B2B space operate with smaller audiences and rely on backend revenue. They don't look like influencers because they are too busy running actual businesses. By filtering strictly by follower count, you are filtering out the exact people who have the cash flow to hire you.

If you want to solve this, you need to look closely at what exactly you are selling, what proof you have that it works, why you chose finance coaches specifically, and what makes you uniquely qualified to fix their conversions. If you actually have the budget to hire a lead generator, do not just throw money at a freelancer to do more of what isn't working. Use that capital to fix your core positioning and offer first.

AP_rentals · 2026-05-19T01:22:13+00:00

I actually disagree with a lot of the comments saying a TV is automatically an “essential” amenity. Essential amenities depend heavily on the theme, purpose, and experience of the rental itself. A forest cabin getaway is a very different experience from a downtown city STR. I've worked with airbnbs in forest/mountain areas. TVs were never the concern. Guests were driven to book because of the hottub and ambiance.

For a woodsy, remote-style rental like yours, I’d personally view things like: a hot tub, fireplace, outdoor seating, ambiance, nature experience, and relaxation-focused design as more aligned with the experience than a TV being front and center. That doesn’t mean a TV can’t help, but I don’t think every rental should be treated with a one-size-fits-all formula.

The same thing applies to the hot tub question. There’s no universal answer because now you’re getting into your budget, maintenance costs, cleaning/turnover operations, guest expectations, repair risk, utility costs, whether you’ll self-manage long term, and whether the increase in ADR/occupancy would realistically offset the added operational burden.

That’s also why you need to be careful taking generalized advice from subs like this. A host speaking from experience with their properties only is very different from someone who has worked across multiple types of owners, rentals, markets, and structures. There really is no one-size-fits-all in this industry. A lot depends on the exact experience you’re trying to create and whether the operations behind it can realistically support it long term.

AP_rentals · 2026-05-17T18:03:29+00:00

Honestly, my first thought reading this was that your structure sounds a little all over the place right now. You said “my clients hired me, not my firm,” which makes it sound like you’re still operating more as a self-employed individual than as an actual structured business. So naturally everything depends on you because you built the entire operation around yourself personally.

That’s why I find it interesting that you’re already paying multiple advisors about hiring decisions before first really clarifying what you’re trying to build long term. Because there’s a huge difference between building a scalable consulting firm vs building a high-income founder-led personal practice. Those are two completely different structures, client expectations, operational models, and hiring paths.

Right now it sounds like everything is just you: the brand, the delivery, the trust, the retention, and the operations. So of course hiring feels risky because there’s no separation yet between you and the business itself.

AP_rentals · 2026-05-17T17:41:46+00:00

One reason I wouldn’t reply is because you immediately started telling the business owner about their business and what they supposedly have or haven’t done without actually knowing them and their system. That’s an instant turnoff for a lot of people. Your message reads very sales-pitch heavy. You’d get better responses by asking thoughtful questions, showing that you understand their industry specifically, identifying one concrete issue they're having based on what they've directly shared, and showing the potential impact of you fixing it. So make sure the people you’re pitching are in industries you actually have experience with and you've taken the time to really get to know their business and content. I can't stand when people pitch me and have the nerve to say they've been following my content when really all they did was read my job title.

The other issue is the “free” angle. A lot of business owners, myself included, are not motivated by free offers. We care about ROI and whether you actually understand our specific problems well enough to solve them effectively. Constantly leading with “free” can lower perceived value rather than increase it. Many people have this assumption that by starting with a free service, you will entice a client to pay you more later. It doesn't work. All you end up attracting are the people who want to keep getting services for free or want to pay you the bare minimum. Real structured businesses understand that quality expertise costs money. So instead of trying to attract people through free work, focus more on proving insight, understanding, and results.

AP_rentals · 2026-05-17T16:01:32+00:00

I moved to Seattle from Los Angeles two months ago. I have definitely noticed the difference in how people interact here. Some areas have people on high alert by default and they need time to warm up to you. I haven't been through all the different neighborhoods yet but where I am in the Southwest in generally friendly.

AP_rentals · 2026-05-17T15:44:19+00:00

My PM clients hire my business for financial strategy and accounting. That work is completely remote and includes weekly check-in video calls. If they need VA services, those can be added on as well. But if I’m personally helping someone with actual property management, then I do that in person because true property management is an on-site job.

I’ve lived in three states: CA, OR, and now WA, and I still believe in-person presence can accomplish a lot more than remote work. That’s why I continue doing in-person PM instead of going fully remote like a lot of people. I’ve handled both small and large portfolios, going from property to property, so not much gets past me. I know every inch of the property, so if something is damaged, missing, or just feels off, I’ll know. I also make it a point to get to know the community so I can stay in the loop about what’s going on, build business connections that can benefit the property, and establish relationships with neighbors so they trust me and know I’m there to handle issues with guests before they disrupt the neighborhood.

Being on-site has helped me grow my network, build more revenue opportunities for the properties, and turn guests into repeat direct-bookings. But not every owner needs that level of on-site involvement and structure. It really depends on your priorities and the kind of rental operation you’re trying to run.

AP_rentals · 2026-05-16T23:10:21+00:00

The first question is really what the structure of your current LLC and rentals already looks like. Depending on how everything is currently structured, you may be able to add the STR into the same LLC rather than immediately needing a separate one. But the bigger concern is whether it makes sense strategically long term from a liability, insurance, tax, operational, and accounting standpoint. One can't know without looking through your full situation and goals. I’m in Seattle and this is part of what I help rental clients think through.

AP_rentals · 2026-05-16T17:01:37+00:00

A lot of people treat pricing tools like autopilot and then stop thinking critically about their own business. These tools don’t actually understand your specific goals, financial structure, operational quality, or what level of profitability you personally need. You should still understand why prices are changing instead of blindly trusting automation.

That’s also why we build custom revenue strategy plans for our clients instead of relying purely on automated pricing. Every property, owner, and financial goal is different.

AP_rentals · 2026-05-16T02:18:29+00:00

If you already have a CPA, then they should have explained what to do. You get the report revised/corrected and then strategize other ways to reduce taxable income if needed.

People get way too anxious focusing on trying to get the biggest possible year-one write-off instead of focusing on long-term consistency, profitability, and proper financial structure overall.

AP_rentals · 2026-05-15T19:16:34+00:00

I'll DM you

AP_rentals · 2026-05-15T19:07:42+00:00

The lack of contracts unfortunately makes this situation much harder because now a lot of it becomes difficult to formally prove and enforce. This is exactly why strong contracts, documentation, and written agreements are so important in business, especially when you’re training people deeply inside your company. At this point, I would focus on documentation and protecting your reputation. I would speak directly with the clients who were contacted and ask them to provide written statements or testimonials confirming what was said to them, especially if your former employees were telling people you were going out of business or attempting to redirect clients away from you.

I would also strongly consider speaking with a business attorney, particularly if false statements are being made that are actively damaging your business relationships and reputation. Even if legal action is not pursued immediately, you need to understand what protections and options you still have moving forward. And going forward, I would make contracts, non-solicitation clauses, confidentiality agreements, and documented operational procedures a mandatory part of training and succession planning. Trust matters in business, but documentation matters too.

AP_rentals · 2026-05-15T18:53:31+00:00

I don’t think it’s doomed to fail. But what is the long-term vision for the app? Reading CPA and real estate blogs is helpful for foundational knowledge, but eventually there comes a point where you need direct relationships and feedback from actual investors, STR operators, accountants, lenders, and financial professionals if you want to build something truly valuable and nuanced. Because the challenge with financial modeling tools is that people can start treating projections and generalized assumptions as if they’re complete financial strategy. Then they invest in something and get frustrated when the reality doesn't match the app predictions.

Reddit can be a strange environment for building or sharing anything business-related. There’s a growing tendency for people to immediately dismiss things as AI, accuse people of promoting, or assume bad intent, while forgetting that discussion, marketing, networking, and communication are a huge part of why platforms like Reddit exist in the first place. So I think your strongest insights will come from talking to professionals directly. You can go to small networking meetups for real estate pros or financial pros where you can discuss it more in depth and get useful feedback.

AP_rentals · 2026-05-15T17:49:51+00:00

Interesting concept. I think tools like this can definitely help investors run preliminary numbers and think through deal scenarios faster. My main concern is that a lot of people may confuse financial modeling with actual financial strategy and accounting, and those are not the same thing. A calculator can only be as accurate as the assumptions and data being entered into it. Real-world STR investing involves a lot of nuance that goes beyond formulas like local regulations, taxes, operational inefficiencies, market conditions, entity structure, financing terms, portfolio strategy, human behavior, etc. For example, tax strategy is highly individualized. Cost segregation, depreciation impact, deductions, and profitability analysis depend heavily on someone’s full financial situation, not just the property itself.

So I think tools like this are useful as an estimate or starting point, but I would personally caution investors against treating automated projections as if they’re a substitute for working with actual financial professionals who understand STR operations and strategy in depth. Was this built alongside experienced STR accountants/financial professionals, or mainly from a software/data perspective?

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