Trevor McCandless, CPA

Happy Friday fellow nerds. You worked your tails off and it's time to enjoy a very deserved three day weekend

Tax deadline day. All returns complete, and 65 degrees this morning in Tuscany. Grateful to work with an amazing team and all star clients.

Manners and mentoring matter at every stage of life, and it starts from the top. Our younger generations need to witness and see first hand how we handle ourselves and treat other people.

Three new clients that all want to convert their Partnerships to C Corps this week. All good and we love meaty, impactful projects. Each of the conversions make sense and are better for them in the mid to long term, but oddly none of them truly had a legit law firm they were already working with... Hopefully that's not a trend. Also realizing I need more corporate attorneys to refer to

Whether you're taxed at 37% or 24% changes what a deduction is actually worth. A $50,000 write-off can save you up to $18,500 in your highest-rate year. That's the whole logic behind planning a spike year on purpose, not just filing it in April. I get into the moves that actually do this here: hubs.li/Q04wzk2Y0

I'm so glad @tbpn is back on. Glad y'all enjoyed your surfing and pizza but a mouse needs his tech news updates!

One of the things I love about the whole recruiting/interviewing process is getting to know more tax pros out there. There's actually quite a few friends I've made out of the process. While the stars didn't align at that moment, we didn't let that get in the way of a good hang

As an entrepreneur, there's nothing better than waking up on a Monday and looking forward to crushing the week with your team

We've been talking about RSUs a lot lately, and the planning conversation looks completely different depending on the company. If you're at a a high tech, privately held startup founded within the last 5 years, it's not a given that the company is going to be around in 20 years. The conversation there is about 22% vs 37% withholdings, whether to sell shares as they vest to cover the tax, or to hold onto as much stock as possible while the company's still privately held. Whereas, if you're at a company that's been around for 20 years with even more robust executive incentive packages such as deferred compensation plans where you reduce your salary now and get it years down the line when your tax rate might be lower. The RSU conversation may be leaning more toward diversifcation. More toward 37% and sell. Two very different RSU conversations at two different ends of the planning curve.

btw if you're tax team is emailing, calling you right now, it's probably a really good idea to pick up the phone. Time is of the essence.

One of our clients had used a Kaiser Permanente plan for years. The company covered the full employee-only premium, and employees could add family coverage at their own cost. That worked well while the whole team worked out of the same state. Kaiser is a common choice for employers in its home markets, but it’s a regional plan. As of 2026, it operates in eight states: California, Colorado, Georgia, Hawaii, Maryland, Oregon, Virginia, and Washington. Members generally need to live or work inside a Kaiser service area to enroll. Outside those areas, coverage is generally limited to emergency and urgent care. By the time this client’s team had grown across several states, only about half fell within Kaiser’s service areas. The employees living outside that footprint were paying into a plan that didn’t give them practical access to routine care where they actually lived.  The owner’s question made sense: if the plan didn’t cover those employees properly anyway, why not let them buy their own policy and reimburse the premium? It sounds like a simple fix, but it's actually much more involved. 🔗 We dig in here: hubs.li/Q04tGz3T0

In 2026, the line item keeping CFOs up at night is not payroll or rent, it is the AI bill. LLM token spend doesn't budget like the software you're used to. Seats scale with headcount. Tokens don't. Route the same task to a different model and the cost can swing a lot, and a pilot that runs a few hundred dollars a month can turn into a five-figure line item the moment it ships to the whole team. Most companies adopted these tools faster than they built the controls to watch them. The fix isn't complicated: code every software and AI dollar to a vendor and department, set a budget at that level, and review it monthly. In our latest piece, we break down the four-step playbook, and why at the small and mid-sized business level, it's usually the controller who runs it, not a CFO. 🔗 Read it here: hubs.li/Q04tjW8P0

If I were starting my company again today, I don't think I'd build it the same way. The last 15 years weren't wrong, it's just that the tools we use to build have changed. I've been using them to go through the business role by role. Me first, then team by team. Same process each time. Feed in meeting transcripts, SOPs, our old training docs, and ask the AI to poke holes in it and help build frameworks. What are we assuming that we've never actually tested? What does this process look like on paper / in theory versus what people actually do? I'm not throwing all of our old processes away, it's just the perfect time to modify and revise them.

22%. That's the default federal withholding when your RSUs vest. If you're in the 32%, 35%, or 37% bracket, and a lot of the equity comp clients I talk to are, that's nowhere near enough. Stock options can worsen the tax gap. Exercise NSOs and you generally owe ordinary income tax on the spread right away. Exercise and hold ISOs instead, and you may owe no regular tax at exercise, but the spread can still trigger the Alternative Minimum Tax before you've sold a single share. The tax planning and forecasting window is the quarter before your next vest or exercise, when withholding, estimated payments, and the overall equity strategy are still adjustable. We're having these conversations with employees at big public tech companies like Google and Spotify as well as pre-IPO unicorns like Anthropic and Anduril. If that sounds like where you are, let's talk strategy before the next vest, not after.

Winning is awesome

Atlanta just hosted eight World Cup matches, including a semifinal. Homeowners near Mercedes-Benz Stadium, in Midtown, and across the metro rented out rooms and whole houses at rates they'll probably never see again.⚽ Here's the best part: if you rented your home for fewer than 15 days this year, that income may be excluded from federal gross income. Not deferred. Not offset by deductions. Excluded under the Augusta Rule. Heard of it? Only issue is that the rule is more nuanced than most people think, and you gotta be precise about how many days you rented, whether the home qualifies as your residence, and even how a Form 1099-K is handled. I get into it here: hubs.li/Q04qh8Mk0

I'm passively in the market to buy a new car and my wife keeps asking me a very critical question. Why buy a car that can't drive itself?

This has got to be a record for least shots at a world cup final