Jeremy Bollinger and Ian Grove break down one of the most misunderstood corners of real-estate taxation: passive vs. active treatment and material participation. Why are rentals default passive? How do the 500-hour, "substantially all," and 100-hour + no one more than you tests actually work? What happens to those juicy depreciation losses if you don't qualify as active? The guys walk through the rules, the traps (hello, property managers + no time logs), and the planning moves that keep you out of penalty land and focused on real wealth building—not clickbait.
Jeremy Bollinger and Ian Grove stay on the myth-busting train to tackle a viral claim: "How the rich use LLCs to hide assets and avoid taxes." Short answer? They don't—at least not legally. This episode breaks down what LLCs are actually for (liability shielding and risk siloing), why "hiding" is just another word for tax fraud, and how sloppy structures and commingled cards can pierce the corporate veil and put your personal assets back on the hook. They also cover the reality behind: Foreign accounts and crypto disclosure questions on your 1040 Why more entities ≠ more savings (often it's more compliance, more fees) When expenses are business vs. personal (ordinary & necessary, facts & circumstances) Car write-offs, mileage tracking, and the limits of "wrap it = 100% business" Estate planning as a legit use of entities (valuation discounts, gifting) that doesn't "solve" income tax The guiding mantra: risk vs. reward—and why clickbait "one size fits all" advice flops in the real world
In this fiery and funny episode of Nailed It: The Construction & Real Estate Finances Podcast, hosts Jeremy Bollinger and Ian Grove hammer into one of the most abused tax topics on social media — the almighty S-Corporation election — and the wave of clickbait "tax gurus" who promise magical savings with LLCs, trusts, and shady entity setups. Jeremy and Ian pull no punches as they unpack why "copying the rich" is bad advice, when an S-Corp actually makes sense, and how to spot BS tax planning before it costs you big time. From the infamous claim "no one's ever lost an audit" to the dangers of taking $400-a-month "reasonable compensation", this episode dives deep into the math, risk, and logic every business owner needs to understand. Expect sharp insights, a few choice rants, and even a hilarious detour involving Taco Bell chalupas and broken bones (literally). It's part education, part comedy roast — and all truth for contractors, real estate investors, and small business owners tired of social media nonsense.
In this fiery episode of Nailed It: The Construction and Real Estate Finances Podcast, hosts Jeremy Bottlinger and Ian Grove sling some playful shade at the tax profession while breaking down three tiers of tax pros: average, good, and exceptional. With their gritty humor, they explain that average pros ensure accurate financials, good ones save you taxes in the current year (like catching missed bonus depreciation), and exceptional ones plan years ahead to slash future tax bills—think QSBS exclusions or entity restructuring. Don't settle for muddy books or "stupid tax"; demand a pro who's got your back! Disclaimer – played at 3x speed: This recording is strictly educational in nature and shall not be considered tax, investment, or legal advice. DO NOT attempt applying any of these ideas without consulting your tax, investment or legal professional. --- Hosted by Ian Grove and Jeremy Bollinger
In this jam-packed episode of Nailed It: The Construction and Real Estate Finances Podcast, hosts Jeremy Bottlinger (aka Dr. Bot) and Ian Grove break down the critical concept of basis with their signature banter, dodging "mister" titles and deep-fake Dodge Viper dreams. They explain basis as your investment's cost—think stock purchases or real estate—adjusted for contributions, depreciation, and liabilities, using examples like Adobe stock and HVAC replacements. They highlight how tangible property regs can save taxes by avoiding depreciation recapture, and warn how poor basis tracking can lead to overpaying on distributions or company sales. Stay sharp, or you'll be crying over taxable distributions! Disclaimer – played at 3x speed: This recording is strictly educational in nature and shall not be considered tax, investment, or legal advice. DO NOT attempt applying any of these ideas without consulting your tax, investment or legal professional. --- Hosted by Ian Grove and Jeremy Bollinger
In part two of this Nailed It: The Construction and Real Estate Finances Podcast episode, hosts Jeremy Bottlinger and Ian Grove dig deeper into project fades, gains, and sandbagging, with a Wedding Crashers-style zing. They explain how project gains (extra profit) boost working capital by reducing overbillings, helping contractors secure more bonded work, while fades shrink margins and hurt financials. With their irreverent humor, they stress leaking gains gradually to avoid tax hits and financial waves, urging contractors to work with savvy CPAs to dodge "stupid tax" and optimize returns. Don't let fades sink your ship! Disclaimer – played at 3x speed: This recording is strictly educational in nature and shall not be considered tax, investment, or legal advice. DO NOT attempt applying any of these ideas without consulting your tax, investment or legal professional. --- Hosted by Ian Grove and Jeremy Bollinger
jjIn this punchy episode of Nailed It: The Construction and Real Estate Finances Podcast, hosts Jeremy Bottlinger and Ian Grove dive into the contractor's world of project fades, gains, and sandbagging with a nod to Wedding Crashers. They define a fade as a job coming in under expected profit (e.g., 30% margin drops to 25%) and a gain as exceeding it (30% to 35%). Sandbagging? That's when savvy project managers hold back profits to avoid getting chewed out later. With their signature humor, they stress leaking gains gradually, not all at once, and tease part two on tax and financial impacts. Disclaimer – played at 3x speed: This recording is strictly educational in nature and shall not be considered tax, investment, or legal advice. DO NOT attempt applying any of these ideas without consulting your tax, investment or legal professional. --- Hosted by Ian Grove and Jeremy Bollinger
In this contractor-focused episode of Nailed It: The Construction and Real Estate Finances Podcast, hosts Jeremy Bottlinger and Ian Grove unpack the critical topic of over and unallocated indirect costs. They break down direct costs (labor, materials, subs) versus indirect costs (equipment maintenance, supervisor salaries) and overhead (admin, rent), explaining how misallocating indirect costs can tank bids or profitability. With their gritty humor, they highlight how overestimating costs might mean missed jobs, while underestimating can lead to financial ruin—especially in today's high-interest, competitive market. Tune in for data-driven tips to keep your construction biz humming! Disclaimer – played at 3x speed: This recording is strictly educational in nature and shall not be considered tax, investment, or legal advice. DO NOT attempt applying any of these ideas without consulting your tax, investment or legal professional. --- Hosted by Ian Grove and Jeremy Bollinger
In this data-driven episode of Nailed It: The Construction and Real Estate Finances Podcast, hosts Jeremy Bottlinger and Ian Grove break down the nitty-gritty of over and under billings for contractors. They explain how percentage of completion accounting smooths out financial waves, matching revenue to expenses using cost-to-cost metrics. Overbillings—sitting pretty as liabilities—signal a job's going well, while underbillings, listed as assets, often spell trouble unless justified. With their usual wit, they stress strategic planning to avoid tax pitfalls and cash flow woes, urging contractors to bill smart and keep those financial dashboards humming! Disclaimer – played at 3x speed: This recording is strictly educational in nature and shall not be considered tax, investment, or legal advice. DO NOT attempt applying any of these ideas without consulting your tax, investment or legal professional. --- Hosted by Ian Grove and Jeremy Bollinger
In this lively episode of Nailed It: The Construction and Real Estate Finances Podcast, hosts Jeremy Bottlinger and Ian Grove, fresh off surviving a hurricane-induced hiatus, dive into the "Lazy Man's 1031 Exchange." They explain how this savvy workaround skips the rigid 45-day identification and 180-day closing rules of a traditional 1031 exchange by selling a property, buying a replacement within the same tax year, and using cost segregation to offset gains with accelerated depreciation. With their signature humor, they highlight the flexibility to retain cash and avoid pricey intermediaries, urging listeners to plan smart with a CPA to dodge tax traps. No Dr. Seuss-level tongue twisters here—just solid tax hacks! Disclaimer – played at 3x speed: This recording is strictly educational in nature and shall not be considered tax, investment, or legal advice. DO NOT attempt applying any of these ideas without consulting your tax, investment or legal professional. --- Hosted by Ian Grove and Jeremy Bollinger
In this eye-opening episode of Nailed It: The Construction and Real Estate Finances Podcast, hosts Jeremy Bottlinger and Ian Grove dive into the wild world of property managers who might be fleecing you—or just clueless. They share horror stories of fraud, like a manager swiping $36,000 by fudging owner statements, and stress the mantra "trust but verify." From dodgy trust accounting to inflated lawn service invoices, they urge listeners to scrutinize statements, demand receipts, and lean on savvy CPAs to spot red flags. Don't let your beer money vanish—verify those numbers or cry over spilt brew! Disclaimer – played at 3x speed: This recording is strictly educational in nature and shall not be considered tax, investment, or legal advice. DO NOT attempt applying any of these ideas without consulting your tax, investment or legal professional. --- Hosted by Ian Grove and Jeremy Bollinger
In this timely episode of Nailed It: The Construction and Real Estate Finances Podcast, hosts Jeremy Bottlinger and Ian Grove geek out on cost segregation studies amid tax deadline chaos. They break down top methods like detailed engineering from actual costs (grab that schedule of values!) or estimates by real pros, versus sketchy cheapos that flop in audits—like getting tax tips from a vending machine. With casual jabs at fly-by-night providers and TikTok "experts," they stress: pay for quality or risk audit headaches and wasted time. Don't skimp, or you'll be unclogging more than toilets! Disclaimer – played at 3x speed: This recording is strictly educational in nature and shall not be considered tax, investment, or legal advice. DO NOT attempt applying any of these ideas without consulting your tax, investment or legal professional. --- Hosted by Ian Grove and Jeremy Bollinger
In this off-the-cuff episode of Nailed It: The Construction and Real Estate Finances Podcast, hosts Jeremy Bottlinger and Ian Grove tackle a listener's question about basis resets in a 1031 exchange, with their trademark wit and no-nonsense vibe. They break down how a 1031 exchange defers capital gains taxes by swapping one property for another, like a Delaware Statutory Trust (DST), but warn there's no basis reset unless you pay the tax or, well, kick the bucket. They also touch on UPREITs and passive income quirks, urging listeners to dodge TikTok tax myths and consult a CPA before making moves! Disclaimer – played at 3x speed: This recording is strictly educational in nature and shall not be considered tax, investment, or legal advice. DO NOT attempt applying any of these ideas without consulting your tax, investment or legal professional. --- Hosted by Ian Grove and Jeremy Bollinger
In this rollicking episode of Nailed It: The Construction and Real Estate Finances Podcast, hosts Jeremy Bottlinger and Ian Grove dish out unapologetic tax talk, diving into a slick strategy for real estate investors: pulling cash from your retirement account for short-term bridge financing. With their Monty Python-esque tangents, they explain how to withdraw from an IRA or 401(k) and repay it within 60 days to avoid taxes and a 10% penalty—perfect for quick flips or FHA fix-it reports. But beware TikTok traps and plan like a pro, or you'll be crying over spilt Dodge Viper dreams! Disclaimer – played at 3x speed: This recording is strictly educational in nature and shall not be considered tax, investment, or legal advice. DO NOT attempt applying any of these ideas without consulting your tax, investment or legal professional. --- Hosted by Ian Grove and Jeremy Bollinger
In this lively episode of Nailed It: The Construction and Real Estate Finances Podcast, hosts Jeremy Bottlinger and Ian Grove dive into cost segregation, the tax-saving superhero for real estate investors. They break down how cost seg studies accelerate depreciation, turning 27.5- or 39-year schedules into 5-, 7-, or 15-year chunks, turbocharged by bonus depreciation (100% in 2017-2022, now 40% in 2025). With their signature humor, they warn against cheap, shoddy cost segs and urge listeners to pick savvy providers—think contractors, not your CPA—to maximize deductions. Don't blow your savings on a Dodge Viper, though! Stay tuned for more tax hacks. Disclaimer – played at 3x speed: This recording is strictly educational in nature and shall not be considered tax, investment, or legal advice. DO NOT attempt applying any of these ideas without consulting your tax, investment or legal professional. --- Hosted by Ian Grove and Jeremy Bollinger
In this episode of Nailed It: The Construction and Real Estate Finances Podcast, hosts Jeremy Bollinger and Ian Grove tackle depreciation with their usual wit, breaking down this tax trick for construction and real estate pros. They compare GAAP's "let's keep it smooth" vibe to IRC's "slash those taxes" approach, explaining how to write off assets like trucks or buildings without tanking your balance sheet. Watch out for rookie mistakes like over-depreciating or tossing a $30 lamp on the books—yep, Ron Burgundy would love that lamp! They also tease a juicy cost segregation chat to save you serious cash. Disclaimer – played at 3x speed: This recording is strictly educational in nature and shall not be considered tax, investment, or legal advice. DO NOT attempt applying any of these ideas without consulting your tax, investment or legal professional. --- Hosted by Ian Grove and Jeremy Bollinger
There's a lot to cover when it comes to real estate tax strategies! Jeremy and Ian break down the first steps in exploring this topic. Tune in to gain valuable insights. Watch us on YouTube! Don't forget to rate, review, subscribe, and share! Disclaimer – played at 3x speed: This recording is strictly educational in nature and shall not be considered tax, investment, or legal advice. DO NOT attempt applying any of these ideas without consulting your tax, investment or legal professional. --- Hosted by Ian Grove and Jeremy Bollinger Produced by Jeremiah Isley, Crooked Path Productions
Learn to navigate entity selection with Jeremy and Ian. They cover tax vs liability purposes behind choosing an entity, explain why you need a rock solid operating agreement (not something off social media) and cover the pros and cons of S Corps vs. LLCs vs. C Corps, and so much more. Watch us on YouTube! Don't forget to rate, review, subscribe, and share! Disclaimer – played at 3x speed: This recording is strictly educational in nature and shall not be considered tax, investment, or legal advice. DO NOT attempt applying any of these ideas without consulting your tax, investment or legal professional. --- Hosted by Ian Grove and Jeremy Bollinger Produced by Jeremiah Isley, Crooked Path Productions
If you enjoy the podcast, I hope you'll take a moment to leave us a rating. That helps us grow our audience! Watch us on YouTube! Choosing a financial advisor, CPA, or attorney, needs to be done carefully and appropriately. Ian and Jeremy give you the tips and tricks of the trade. Ask good questions, such as what are their exact credentials. Learn the difference between CPAs, EAs, accountants, and someone who does taxes. Also be aware of 4 common ways that retained earnings get screwed up. Don't forget to rate, review, subscribe and share! Disclaimer – played at 3x speed: This recording is strictly educational in nature and shall not be considered tax, investment, or legal advice. DO NOT attempt applying any of these ideas without consulting your tax, investment or legal professional. --- Hosted by Ian Grove and Jeremy Bollinger Produced by Jeremiah Isley, Crooked Path Productions
Meet Ian and Jeremy! Ian has a background in banking, sales, and financial advising. He and Jeremy work to gether daily. Jeremy is a CPA and CCIFP, specializing in construction. He enjoys advisory as well as helping contractors identify and improve innefficencies in their business. He loves to teach, train, and educate. Don't get lost in the weeds. Crack open a beer and join Ian and Jeremy as they break down construction and realistate taxes for you. Subscribe now! If you enjoy the podcast, I hope you'll take a moment to leave us a rating. That helps us grow our audience! Watch us on YouTube! Disclaimer – played at 3x speed: This recording is strictly educational in nature and shall not be considered tax, investment, or legal advice. DO NOT attempt applying any of these ideas without consulting your tax, investment or legal professional. --- Hosted by Ian Grove and Jeremy Bollinger Produced by Jeremiah Isley, Crooked Path Productions