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

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.

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.

The Balance Sheet Tells the Real Story—Not the Income Statement Back in my auditing days at Deloitte and Grant Thornton, I learned a simple but powerful truth: if you know the balance sheet and can support the numbers, the income statement has already been audited. Now, as I work on tax returns for companies where we don’t do the accounting, I see the same pattern—all the errors are on the balance sheet. Numbers don’t tie, assets are misstated, liabilities are missing. And if the balance sheet is wrong, so is everything else. Yet, so many business owners focus only on the P&L, ignoring the bigger picture. Here’s why the balance sheet matters more: Cash Flow vs. Profitability – You can show a profit but still run out of cash. The balance sheet reveals how much liquidity you actually have. Debt and Leverage – Making money is great, but how much debt are you carrying? The balance sheet shows whether you’re overleveraged or set up for long-term success. Business Valuation – If you ever want to sell or raise capital, investors and buyers care more about assets, liabilities, and equity than just a single year’s profit. Long-Term Sustainability – The income statement is a snapshot. The balance sheet tracks your business’s financial strength over time. If you truly understand your balance sheet, you understand your business. Ignore it, and you’re flying blind. Know your numbers. Know your balance sheet.

One thing I've noticed each tax season, working on business tax returns for companies, is that a lot of owners don't review their financials frequently - monthly or quarterly. They tend to be accounting files that we don't manage. Before the tax prep process starts, it starts by reviewing the balance sheet, bank/credit card reconciliations, then payroll reconciliations, then the profit and loss statement. Owners may want to save money and try to do the accounting themselves, then maybe have a firm check it over right before the tax filing. It's not an efficient process and could miss errors that could have been found earlier. Business owners - outsource your accounting, but be involved by having your accountant review the financials with you. Don't wash your hands of the accounting - stay involved.

A couple of weeks into tax season, one of the items I see every year are younger families with kids not having a Will, Trust, etc. set-up. Some have used online tools for basic Wills. Similar to new business owners having basic accounting and tax 101 knowledge, I think it would be a good idea for new families to have Will/Trust education - just the basics and intros to estate attorneys. This goes back to the lack of personal finance education in school.

This is a great read. People in their 90s and 100s still preparing tax returns. They do it because they like it…keeps them busy and mind sharp. Some tax professionals keep crunching numbers at more than 100 years old. wsj.com/lifestyle/taxes-acco…

Last night, caught up on Landman and saw the Jerry Jones episode—his speech really hit home. He talked about how his greatest pride isn’t just in business or football, but in working alongside his kids. That stuck with me. Success isn’t just about what you build—it’s about who you build it with. It’s easy to get caught up in chasing goals, but moments like this remind me why we do it in the first place.

I wish new business owners have to have some sort of basic accounting/tax 101 - just the very basics - before they can start a business.

In the past two weeks, I’ve received four separate requests for CFO services. But after digging in, none of them actually needed a CFO. Often, when prospects reach out asking for CFO services, what they really need isn't always what they think. They might say they need a CFO, but after digging in, it turns out they need: Better bookkeeping – Their financials are a mess, and they need clean, accurate numbers before they can even think about strategy. Cash flow clarity – They don’t actually need forecasts; they need to understand where their cash is going right now. Tax strategy – What they’re really asking is how to pay less in taxes, which is a tax planning issue, not a CFO one. Profitability insights – They assume they need high-level CFO oversight when in reality, they need someone to help them understand margins and cost control. A CFO role is about forward-looking strategy, fundraising, M&A, and big-picture financial planning. But many small businesses think "CFO services" means fixing disorganized books, handling payroll, or answering tax questions. Before jumping into a CFO engagement, ask: What financial pain point are you actually trying to solve? Are your books even in good enough shape to use financial data strategically? Do you need a CFO—or just better accounting, tax planning, and reporting? Most of the time, it’s not CFO services they need first—it’s a solid financial foundation.

I'm seeing and hearing more and more people quit their corporate W2 job to start their business. It could be a solo business or a couple of friends seeing an opportunity to solve a bigger problem. The common denominator is people want to be happy at work, even if it means a lower annual salary. I spoke with a client last week that is leaving a $600K/annual salary to start a solo business - earning, at most $140K a year.

I just published 4 Personal Lessons from The Anxious Generation: A Journey of Understanding link.medium.com/C41Pdtw0wQb