Rob Pasquesi, CPA

Financial planning for 2025, here is our calendar, by month, on important dates and items to consider to avoid any finance or tax surprises. Page 1 of 2

@TheRobertBshow So true…great post…was thinking about this as our daughter starts 1st grade tomorrow

You get 18 summers. Then they're visiting. You get 940 weekends. Then they have their own. You get 6,570 bedtimes. Then silence. Time is the only real currency of parenthood. Spend it wisely. You can't earn more.

Reviewing a prospect's business tax return. No one is perfect, but some of the items on the balance sheet is shocking - prior period adjustment, accrual accounts when the business is cash basis. Business owners - your tax returns may seem like compliance, but if not done correctly, they could have an impact later. It's important that you understand the numbers reflected on the tax return BEFORE it's filed. Meet with your tax preparer and have them walk through the tax return with you.

Congrats to @bluejlegal Rd D of fundraising - $122M. We're huge fans of the product - as a tax research tool, its one of the best on the market. Looking forward to future features.

I follow only a few on Substack, one of which I really like is Stoic Wisdoms. A post from them today about achievements vs. legacy is a good one. As you build your company or continue on your career path, think about if you were to leave - no LinkedIn profile, no awards, no recognitions - what would you leave behind? What impact would you have on the world? buff.ly/fQ5cDao

Is your business travel actually tax-deductible? How about those family trips? There is more to it, but keep to these four IRC 162 requirements that a lot of business owners get wrong: 1) Must be ordinary and necessary for your specific business; 2) Away from your tax home - that's your business location, not your residence; 3) Primary purpose must be business, not personal convenience. 4) Missing proper documentation? You lose the entire deduction. The IRS scrutinizes travel expenses heavily.

This is becoming increasingly common among do-it-yourselfers when it comes to retirement plans. I see this at least twice a year. Making direct Roth IRA contributions and not considering their AGI. There are other ways to contribute to a Roth IRA if your AGI exceeds the limits. Plan ahead and talk to your advisors before making any contributions.

I see this too often, but it usually comes in after the fact. New businesses often start without using a proper law firm for operating agreements, structure, etc. Tax compliance is due, but the owner lacks clarity on their entity type, tax classification, and other relevant details. It’s not just a formality—it impacts a lot. Take the time. Get organized. Own the outcome.

Some days, it’s great to take a break from work and enjoy a round of golf or another activity you love. That’s one of the perks of being a business owner! Had fun playing Conway today.

@CPATaxTeam Agreed…I started it last night and definitely exceeded my expectations…it’s great as well as the cameos

Happy Gilmore 2 is actually pretty funny. Great cameos and some good throwbacks to the OG.

Most people think personal finance is complicated. The truth is, it’s the basics that matter most—and they’re often the ones we overlook. If you don't understand how money flows in and out of your life—how you earn it, how you save it, how you spend it, and how you grow it—you’ll always feel like you’re playing catch-up. You don’t need a PhD in economics. You just need a clear foundation: live below your means, save first (not last), invest early, protect what you build, and make decisions based on long-term thinking, not short-term emotion. Master the basics, and everything else gets easier. Ignore them, and no amount of income or luck will save you. Personal finance isn't about being perfect. It's about being intentional.

Getting a lot of questions lately about budgeting tools (not a shock given the economy). Just came across Controol App (controol.app) — and it’s surprisingly solid. No bank connections (privacy win) Percentage-based budgeting — plan what you can spend Built-in AI to answer your money questions Super simple to use. Free to try, with extras for $1.99/month. Could be worth checking out.

Markets took a hit today... but that doesn’t mean your portfolio is broken. I just started reading A Random Walk Down Wall Street, and it couldn’t be more timely. One of the central ideas is the Firm Foundation Theory — the belief that each investment has an intrinsic value based on fundamentals like earnings, dividends, interest rates, and expected growth. According to this theory: The market might misprice a stock in the short term… …but over time, price gravitates toward its intrinsic value. So if you’re building on solid ground — companies with real earnings and durable value — you don’t need to flinch when prices dip. Volatility doesn’t destroy value. It just reveals who’s anchored. A crash tests conviction. A foundation holds steady. Stay calm. Revisit your fundamentals. Trust the process. This is how long-term wealth is built.

Another tax season behind, at least another April 15 completed. Overall, happy with what we accomplished by the due date. System and process improvements established earlier had helped. But today's debrief, which happens post-April 15, will uncover further improvements for next year.

@tryjasononline Where is Asana? Always been a huge fan and constantly adding relevant features.

5 years ago I was running a 40 person tax firm We’d invested 14 months, and more time & money than I care to mention into changing practice management systems. But after burning 14 months + $100k in costs, and signing a 3 year contract we were 2 months into, we came to an unbelievably difficult decision: We’d chosen the wrong platform. And now we were going to have to change again. Robes were torn. Teeth gnashed beyond recognition. Staff had left! But we had to start over. Because the right answer? It wasn’t 𝒯𝒽𝑜𝓂𝓈𝑜𝓃 𝑅𝑒𝓊𝓉𝑒𝓇𝓈 𝒫𝓇𝒶𝒸𝓉𝒾𝒸𝑒 𝒞𝒮. We were a 25 year Lacerte firm, and we’d gotten the bold idea to switch to UltraTax. But wouldn’t you know it, they’ll practically give you Practice CS for free the first few years if you sign a contract. Plus, it’s the only PM that integrates with your tax software! Sound familiar? Here’s what I wish someone would’ve told me at the time: 💡 No amount of integrations make crap software worthwhile. There are now profoundly better practice management systems available than what any tax software vendor has on offer. US tax software vendors are legacy companies who are decades behind the curve in every imaginable way. We buy tax software from them because we have no other choice. And our relationship with them should be limited to just that, tax software. Don’t just take my word for it. Make an argument for Practice CS in the replies and watch what happens next 🙂 It’s the greatest grift in modern accounting. Tax software co’s have brainwashed firms into thinking their 20 year old solutions are your only option. So repeat after me: I will not buy anything but tax (and fixed asset) software from my tax vendor. What should you buy instead? Well, in 2025 there are 39 practice management systems being advertised in North America 😵‍💫 But you should only be using one of these 9: Uku Qount Keeper Karbon Canopy Firm360 TaxDome Client Hub Financial Cents Now, was changing to UltraTax the right move? Tomorrow I’ll share my shortlist of the only tax prep platforms I recommend, and a couple new ones in the works that give me hope for the future. And consider reposting this, since most firms haven't heard the good news 🙂

@CPATaxTeam interested in virtual meet up re: financial services

@patrickdichter Huge fans of Holistiplan…year 3 using them

Small improvements we’re trying this tax season: 1. Sent personalized document checklists 2. Loom videos with some tax returns 3. Testing a tax planning software We’ll know by this summer where clients feel value or not.

@PeterRiefstahl Really like it…expensive though. Support has been lacking this year…but overall happy.

What does #taxtwitter think about Axcess? I need more multi state power than Drake and I'm in a pinch for getting this set up, like, yesterday. Help!

@cordes_tax Congrats Matt

Welcome Lilian Ruth! Born 3/17/2025 ☘️ at 6:19pm, thus not requiring an extension of time 😉. Mama is resting and doing well. Baby Lily has a healthy set of lungs. Lily is a perfect blessing from God.

@Codie_Sanchez So true. Focus is key. Ignore the noise.

Dear small business owner, You are not losing your mind. This running a business thing is way harder than anyone tells you, or than social media says. It's more expensive, it's more painful, and most people will never understand.

@JohnBuschVI @CrainsChicago Great write up John

My latest OpEd in @CrainsChicago: As 1871 exits the Mart, a need — and an opportunity — opens up. - - - Earlier this month, 1871 announced its departure from the Merchandise Mart, igniting debates about Chicago’s startup ecosystem. As a current founder and 1871 member, I know what many early-stage entrepreneurs need to succeed: focus and density. This shift is a pivotal moment for our tech scene. Entrepreneurship is glorified suffering. Work at it for years, make a thousand good decisions, time it right, and you might bring your vision to life — improving the lives of your family, team, investors, and customers. It might just be worth it. But to survive the brutal early days of ideation, launch, product-market fit, and fundraising, founders need other founders who get it — swapping investor tips, critiquing products in real time, staying late at the office, and nodding knowingly over the rollercoaster. Silicon Valley thrives on this in-person, high-talent density; Chicago must too. Virtual communities, generic co-working spaces, and monthly meetups don’t cut it — I’ve tried. At 1871, many founders I know felt our needs slipped from focus. It morphed into a broader ecosystem hub, juggling corporate programs, nonprofit partnerships, and university ties — worthy efforts, no doubt, but it no longer offers the strict founder focus a la Y Combinator. Now, Chicago must fill this gap with tight-knit, founder-first communities. Bright spots like @mhub for hardtech, Portal for life sciences, and, most recently, Density.Ventures, a founder-led collective for venture-scale software startups prove it’s possible, echoing the in-person focus 1871 once had. While ecosystem hubs like 1871 are still needed to connect stakeholders, our strength is heavily tied to the success of our early-stage founders. They’re the spark for our economic flywheel. To founders: Come join or build these vibrant spaces. To investors and exited entrepreneurs: Back them to fuel growth. To civic leaders: Partner with us — our fates are linked. Chicago tech’s future depends on keeping founders at its core. Let’s make no little plans — and rebuild the communities we need.