Kindled Planning

05/31/2026

Excited to share something I have been working on, The Kindled Brief, a monthly newsletter from Kindled Planning focused on equity compensation and tax complexity. Whether you have RSUs, stock options, or a pending liquidity event, or you run a business and want to stay ahead of your tax situation year round, this was built for you. Think of it as an extension of what we do at Kindled Planning, practical planning insights to keep you informed all year, not just at tax time. Current clients are already subscribed and Issue 001 goes out tomorrow. If you want on the list visit

One email a month to help you keep more of what you earn.

05/27/2026

Kindled Planning is excited to be a sponsor of the 8th Annual Unified 5k, an inclusive road race and adaptive sports expo in Lancaster, MA this Saturday, May 30th. Participants can walk, run, or roll the 1 mile or 5k distance or join us for a kids fun run with the Railers and Woo Sox mascots. The event raises money for the AdaptX grant program that provides adaptive athletes with running prosthetics, sports wheelchairs, and the equipment that they need to accomplish their goals. We invite you to join us on Saturday at RFK Community Alliance in Lancaster for this impactful event.

04/24/2026

The most expensive phrase in the tax industry is "I wish I knew that sooner".

Ask any tax professional what they hear most often during the April filing deadline, and they’ll tell you it’s a version of that same sentiment. High-performing professionals and business owners often realize they left money on the table simply because they only looked at their taxes once a year.

The truth is, there is a fundamental difference between a Tax Preparer and a Tax Advisor:

📜 The Tax Preparer is the Historian. Their role is vital for compliance, they look in the rearview mirror to ensure your financial history is recorded accurately for the IRS. They are experts at documenting where you’ve already been.

👨‍✈️ The Tax Advisor is the Co-Pilot. We look through the windshield. Our job is to sit beside you during the calendar year, helping you "steer" toward savings opportunities and avoid tax turbulence before the window closes on December 31st.

Why having a Co-Pilot matters for your 2026 flight path:

🚀 For Business Owners: It’s the difference between losing money as a Sole Prop versus optimizing an S-Corp, or ensuring equipment purchases take advantage of 100% bonus depreciation rules.

📈 For Equity Holders: It’s about identifying "withholding gaps" on RSUs or AMT traps on ISOs before they turn into a massive April bill.

🏠 For Growing Families: Even if your situation feels standard, a co-pilot helps you maximize HSAs, time investments, and execute strategic charitable giving.

At Kindled Planning, we believe taxes are a year-round journey. Serving clients digitally across New England, we act as the co-pilot for the consistent check-ins that make a real impact. It’s not uncommon for these proactive strategies to save our clients tens of thousands of dollars over the long haul.

You don't need a "hack" in April; you need a Co-Pilot year-round.

04/23/2026

Sterling roots. Lancaster anchor. New England reach. 📍💻

If you recognize the name Nashoba, you know exactly where my heart is. I grew up in Sterling, went to middle school here in Lancaster, and spent my high school years just down the road in Bolton.

Opening an office in the heart of Central MA wasn't just a business move, it was a homecoming.

But I want to be clear about how we work: Kindled Planning is, and always will be, a digital-first practice. Our secure, paperless operations allow us to serve tech pros in Boston, founders across Massachusetts, and equity holders across all of New England with total efficiency.

So, why the office? Because some decisions are too big for a quick Zoom. I’ve reserved this space, The Strategy Hub, specifically for high-stakes, in-person deep dives:

🏢 Entrepreneurs: Mapping out a multi-year exit or S-Corp transition to save thousands in self-employment taxes.

📈 Equity Holders: Navigating the "Tax Traps" of a major RSU or ISO vest to avoid a massive April surprise.

We aren't a traditional "walk-in" tax shop. We fulfill your practice needs digitally by default, but we’re here in person when the strategy gets deep.

Virtual speed. Local roots.

04/22/2026

Emerging from the "Tax Fog" with a new perspective. 🌫️➡️☀️

It’s been a week since the filing deadline, and at Kindled Planning, we’ve finally caught our breath. Serving so many families and founders in our first full year was a marathon, and the feedback we’ve received has been incredible. Thank you to everyone who trusted us!

But as the dust settles, I want to share how we are evolving.
Most people see a tax pro as a historian, someone you hire once a year to report the past. That is a tax preparer. At Kindled Planning, we are Tax Advisors.

Why does this matter for you?
🚀 For Entrepreneurs: We focus on entity optimization and CFO-level strategy so you aren't losing money through inefficient structures.

📈 For Equity Comp Holders (RSUs/ISOs): We specialize in closing the withholding gap and managing the AMT traps that turn your hard-earned stock into a surprise bill.

💻 Digital-First | Locally Rooted: While we serve clients virtually from Connecticut to Maine, we’ve officially opened our office in Lancaster, MA for deep-dive strategy sessions.

The biggest savings don’t happen in April; they happen now, while we can still steer the ship.

Expect to hear from us daily this week as we share lessons learned from this past season to keep more money in your pocket.

03/02/2026

The Massachusetts March Tease is officially here! 🌷❄️

Anyone else still catching their breath after Saturday? That 50-degree sunshine was a beautiful gift, but Mother Nature decided we needed a reality check with these 30-degree temps today and tomorrow.

The Silver Lining: We just have to power through these chilly couple of days, Wednesday and Thursday are looking like highs in the 50s! In New England, that’s practically patio weather. ☀️

I’m using the "indoors" weather today to fuel up on extra coffee and bridge the gap between this cold start and that warm finish. March is always a marathon, not a sprint, whether you’re navigating the forecast or a stack of paperwork!

Wishing you all a week that feels like a 50-degree Wednesday in March. Hang in there, the thaw is coming! ☘️

02/27/2026

Supporting our local community is at the heart of what we do. We are proud to partner with Parents For The Artz to help these talented dancers reach the stage. We’re rooting for everyone during their upcoming performances!

* Silver Sponsor Spotlight *

PFTA is so happy to announce Kindled Planning as a Silver Sponsor this season! Kindled Planning, founded by Matt Curtin, CPA, is dedicated to helping families and businesses get organized, prepared, and confident about the future. With a thoughtful and personalized approach, Matt guides clients through important planning decisions with care, clarity, and professionalism. If you’re looking for trusted guidance and personalized planning services or tax preparation, be sure to check them out!

Thank you, Kindled Planning, for your commitment and support of PFTA and our dancers!

https://www.kindledplanning.com/

02/25/2026

The "Perfect" Tax Return? (Hint: It’s not what you think!) 🧭🎯

Taxes can often feel like navigating without a map, especially when life starts moving fast.

I’ve been chatting with a lot of you lately, and it’s clear we’re in the "Great Tax Divide." Some of you already have your refunds hitting your bank accounts (congrats on the spring bonus!), while others are just starting to hunt for that last 1099.

I often get asked: "Is a big refund a good thing?"

As a planner, my answer is: It’s all about intentionality. If you got a big refund, that’s your hard-earned money coming back to you. If you had a big bill, it means you kept your cash longer. Both have their perks!

But the "Goldilocks" goal, the one that’s just right, is landing as close to $0 as possible. Think of it as reaching your destination exactly on time.

Why is the "perfect" $0 so hard to hit? Because life is unpredictable:
1️⃣ A new baby or a marriage changes the math.
2️⃣ A mid-year promotion or an RSU vest shifts your bracket.
3️⃣ Market swings change your capital gains.

Landing at $0 is a moving target, and that’s okay! My goal for Kindled Planning clients isn't "perfection", it’s eliminating the surprise. Whether you owe a little or get a little back, the win is knowing it was coming.

If your result this year felt like a total mystery, let’s make 2026 the year of "No Surprises"!

02/13/2026

Between Friday the 13th today and Valentine’s Day tomorrow, there’s a lot of 'fate' in the air. 🏹 But when it comes to your taxes, we try to leave luck out of it!

Whether you’ve recently tied the knot, started a family, or your filing status changed this past year, congrats! Just a heads up: your heart isn't the only thing affected. A change in status can definitely add a few layers of 'it's complicated' to your tax return. 📝

If your filing situation feels more like a thriller than a romance novel right now, don't worry. That’s exactly what we're here for; powered by coffee and a calculator, making sure every deduction finds its perfect match. ☕️✨

Happy Valentine’s Day! Here's to making sure your tax return is as smooth as your holiday dinner plans. ❤️🥂

02/07/2026

The Sweet Spot of Tax Season (and a quick heads-up)!

Check your mailboxes 📬 Most W-2s and 1099s have likely arrived by now, but there’s often one important piece still outstanding: brokerage statements.

If you have investment accounts, consolidated 1099s aren’t required to be issued until February 17th this year, and many brokerages wait until late February or early March to avoid sending corrected versions later.

Why this matters:
1) Don’t rush to file. Waiting for final brokerage statements helps avoid amendments down the road.

2) Do reach out now. Even if one document is still pending, February is the ideal time to get on the calendar and talk through next steps.

A quick note on availability: I keep a limited client list so I can stay responsive and thorough. I expect to close new client onboarding toward the end of this month. If you’ve been following along and want to ensure a spot this year, now’s a great time to connect while the calendar is still flexible.

🔗 Book an intro call via the link below:
https://calendly.com/matt-kindledplanning/initial-consultation