TechbroSTRs is for tech professionals who invest in short-term rental real estate to diversify beyond equity comp and reduce their tax liability. How to pick a market, how to underwrite a deal, how to launch the property, and the tax concepts to review with your CPA. Built by product managers, data scientists, and engineers from tech companies who have done it themselves.
No pitch and no package. We apply the full walkthrough to the market or deal you are considering.
Two reasons drive nearly every buyer we talk to. Most are motivated by both.
Unvested RSUs, ISOs, ESPP. Most of your wealth is tied to one company's stock price, and it vests on someone else's schedule. A short-term rental adds a real asset that does not move with your employer's shares and can generate income while you hold it.
It is the simplest reason on this page, and for many buyers it is the whole reason.
Above $400k in W-2 income, there are few levers left. Short-term rentals come with specific tax concepts worth understanding before you buy: cost segregation, bonus depreciation, material participation, and the 7-day rule. These are concepts to review with your CPA, not promises. See the tax section below.
Understand them before you buy, not after.
Four markets live. One more on the way. We only discuss places where we have done the work.
Home market. We own and operate short-term rentals here, so the numbers we share come from our own properties.
The Catskills and Hudson Valley. We have completed full underwriting work there and can walk through both markets side by side.
Live now. Market research is underway, and video walkthroughs are available.
Live now. Strong demand, research underway, and video walkthroughs available.
The Bay Area. We lived there for years, and video walkthroughs are available now.
Five steps, in order. This is the process we follow ourselves, built from our own properties in Austin and the underwriting work we have done in other markets.
Define the guest before the property: families, business travelers, groups, couples. Different guests need different homes. Then verify demand with rental data: does that guest actually book here, and is the market undersupplied for what they want.
Write down your criteria before you shop: guest, market, size, revenue multiple, down payment, setup budget. No real deal passes every filter. The buy box tells you which exceptions are acceptable.
Decide with a spreadsheet, not a feeling. Screen quickly with a revenue multiple, then model three scenarios: conservative, base, and aggressive. If the base case requires everything to go right, pass.
Line up cleaners, pricing, photography, and systems before the first booking. The first 30 days set your review trajectory.
Keep timestamped records from day one: hours worked, expenses, stays. Your CPA will need them, and reconstructing later is unreliable.
These are the concepts high-earning buyers ask about most. Educational only, not tax advice. Your CPA makes the final call on everything here.
An engineering study that classifies parts of the property into shorter depreciation schedules, moving deductions into the early years of ownership. Often discussed alongside bonus depreciation. Whether it applies to you is a CPA question.
When the average guest stay is seven days or fewer, the activity is treated differently from a long-term rental under the tax code. Track average stay length from the first booking.
One common test is 100+ hours per year on the property, more than anyone else involved. Contemporaneous time logs matter. Your CPA determines whether you qualify.
Educational content only. This is not tax advice. Talk to your accountant.
Not advisors. Operators who have done this.
Brent is an accountant and short-term rental owner in Austin. Ariel works in sales and has walked this path alongside him. Together they are product managers, data scientists, and engineers from tech companies who have done this themselves.
We have worked through the local and federal headaches: multi-state tax filings for W-2 income, RSUs, and early exercise, including RSUs granted in one state while living in another. California, New York, and New Jersey included.
We have run cost segregation studies, taken accelerated depreciation, built ADUs, set up LLCs, and kept the logs your CPA, or your favorite AI assistant, will ask for. We have found the furnishing and Airbnb discounts, the handymen, and the photographers. And we have sat through the accountant and financial advisor meetings where they did not quite get it.
Thirty minutes, focused on your situation. We walk through the market or deal you are considering and give you a straight read on whether the numbers work.
Send a message and we will confirm a time. Tell us the market you are looking at so we can prepare.
Message to bookReplies within one business day.
Answered directly.
Nothing on this page. No course, no coaching package, no upsell. This is the walkthrough we wanted when we started, and the consult is a conversation, not a funnel.
No. We explain the concepts so your CPA conversation is productive. The final word is always theirs.
Use the booking section above to send us a message. We will confirm a time, usually within one business day.
Yes. The process is the same everywhere; only the numbers change. We have completed full underwriting work in the Catskills and Hudson Valley, so we can talk Austin, upstate, or both.
Coming soon. We lived there for years. The walkthrough still applies, and video is easy in the meantime.
Tech professionals with high W-2 income who are considering short-term rentals in Austin, the NY area, Boston, or Miami. If that is you, the walkthrough applies directly.
A market or listing you are considering, and a sense of your goals: diversification, tax planning, or both. We will bring the framework.