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Lookout Outlook | May 2025 | Bookkeeping Newsletter

Published 6 months ago • 4 min read

Tax season is over... what’s next?

There are three types of people post tax season: those who filed their returns, those who extended, and those who are panicking…

If you find yourself in the panic crowd, we can assist with historic bookkeeping to get your 2024 financial reports together! Click here to get started.

If you’re in the first two buckets, you can’t get too comfortable!

One of the sneakiest tax deadlines of the whole year is the second quarter due date for estimated taxes—it comes just two short months after you paid your first installment in April!

June 16th (the Q2 estimated tax deadline) is coming up quickly, and May is a great time to get organized and avoid surprises. Missing a quarterly tax payment can result in penalties and interest (even if you filed on time in April!), so it’s always best to stay proactive.

Need help figuring out how much you need to pay next month? Having your bookkeeping completed is step one! If you're not completing that task, we are here to help!

Recommended Listening

​Sequestered Podcast​

This month I'm departing from my usual topics to bring you a little something different. Recently, I finished listened to the Sequestered Podcast—A Juror's Perspective on the Murder Trial for Jasmine Rice. If you're local to Chattanooga, you're most likely familiar with this case. The podcast was well done & takes you through the entire trial; I highly recommend you listen.

Chattanooga Entrepreneur Week!

The 2nd Annual Chattanooga Entrepreneur Week is Monday, May 5th — Saturday, May 10th, 2025. I plan to attend a few of the events — hope to see you there!

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This Month's Freebie!

Systems = Freedom.
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After helping dozens of business owners clean up their books and streamline their operations, these are the 3 vendors I recommend every time:
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✅ Gusto for stress-free payroll
✅ Relay Financial for a Profit First banking platform
✅ Anchor for seamless proposals and payments
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The right tools don't just make life easier — they keep you PROFITABLE.
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📈 Want to know how these tools fit into your business? Click below!

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In Closing...

I’ve got homework for you! Reflect on your most recent tax season using this quick survey and rate your experience from a 1-5 (5 being the best!).

  • How was the communication from my tax accountant? Did I feel like I truly understood my return or reason for extending?
  • For my business, were my books prepared in a timely and accurate manner to be used to prepare my tax return?
  • How happy am I with my current finance team?

If you got a total of at least 9 and up, it sounds like things are going pretty good! But if you're scoring your tax season experience lower, May is the perfect month to make a change!

If you're looking for a referral to a tax preparer — let me know!

Vendor Spotlight – Clockwork.ai

I'm extremely excited to announce I'm now offering Business Advisory Services, in addition to the best-in-class bookkeeping you already know we provide. A few of the services are listed below:

● Cash flow forecasting and financial modeling with CFO level accuracy

● Custom Metrics Dashboard to manage all KPIs important for your business in real-time

● Scenario modeling based on all your "what if" questions

● 24/7 access to custom metrics and reporting packages, plus monthly reporting

If you've been wanting to get more information from your numbers, see projections on cash flow, and put in scenarios to estimate what changes with income and expenses will do for your business, this is the answer!

There are three tiers of service within advisory & I'd be happy to chat with you in order to find which one is a good fit for you and your business.

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Looking for a DIY Solution?

Look no further than our Small Business Bookkeeping Tracker! For the start-up side gig who just has a few transactions a month, this tracker will be your BFF for tax filing. You can enter your transactions each month and this tracker will produce monthly and annual reports. The best solution for any business until you need to partner with a bookkeeper to provide done for you services.

$97.00

Small Business Bookkeeping Tracker | Lookout Bookkeeping

This Small Business Bookkeeping Tracker in Google Sheets helps you keep track of your business income, expenses and... Read more
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Cheering You On!

PO Box 2475, Chattanooga, TN 37409
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