Lookout Outlook | June 2025 | Bookkeeping Newsletter


Your Official Summer To-Do List

If you’re self-employed, part of a pass-through entity, or have other sources of income not subject to tax withholdings, mark your calendar for the Q2 estimated tax deadline on June 16th. If you'd like to add these tax deadlines and more to your calendar, feel free to grab my tax calendar here.

Pro Tip: If your income has grown in the first half of 2025 (yay!), your original estimated tax payments from April may no longer be accurate. If you have a safe harbor payment amount from your tax accountant, this can help you avoid underpayment penalties and interest. But, consider getting a mid-year tax projection to adjust to a more accurate payment and prevent a tax-time surprise next April!

Here’s what else smart business owners are focusing on this summer:

  • Make sure you have completed Form W-9s from all of the contractors you’ve hired in 2025. REMINDER: If you're a client, we are pro-actively asking for these forms or your vendor's email, so we can request the W-9 form on your behalf.
  • Ensure all of your transactions are accurately recorded, categorized, and reconciled through May.
  • Review cash flow projections to ensure you have enough cash on hand to meet obligations (especially if you normally have a summer slowdown!)

Recommended Reading

This month, I'd like to help you get a jump start on your W-9s. As a business owner, it's easy to forget to request those pesky W-9 forms from your various vendors. Head on over to my blog to learn more about how I stay on top of my W-9s throughout the year!


This Month's Freebie!

Who doesn’t want to keep MORE of their hard-earned money without working more hours? July’s freebie is all about actionable strategies to work smarter, not harder.


In Closing...

Feeling unsettled by changing tax laws, tariffs, and a turbulent economy?! I want to be your resource for all things finance: if you want more info on how these changes could affect your business, please respond to this email with your questions! If I’m not the right person to help you, I’ll work to put you in touch with someone who can.

Lastly, I want to touch on the summer slowdown (and the opportunity it presents to get your financial life organized!). While you’re flying overseas to Greece, road-tripping to Disney, or just lounging by the pool, I can be cleaning up your books and putting calm to the financial chaos.

If you’d like monthly bookkeeping services, cash flow forecasting, or want to hop on a call to learn more about how I can help you this summer, respond to this email and I’ll send you more details on next steps.

If you’re in a slower season, this is a perfect chance to focus on how to implement technology to make your systems run well for you. I’d love to help you head wrap up Q2 with confidence and clarity!


Vendor Spotlight – American Express

If you are looking to add a credit card to your business, I highly recommend American Express. They have a couple of options for business owners, and I have utilized both in my business.

The first option highlighted is the Business Blue Cash Card. The Business Blue Cash Card from American Express was my first credit card in business. There is no fee, and an introductory 0.0% APR for purchases in the first 12 months. You will earn 1.5% Cash Back on purchases in the form of a statement credit each month, too.

With the Blue Card, when you spend $5,000 in the first 6 months of card membership, you'll get a $250 statement credit.

DISCLAIMER: Program benefits may change at any time.

Full disclosure: By using this referral link, you will receive $250 statement credit when you spend $5,000 in the first six months of having the card. When you signed up, I will receive a $50 statement credit as well.

Please be wise when choosing to utilize credit for your business.

The second option highlighted is the Delta SkyMiles® Reserve American Express Card. If you travel and use Delta Airlines for your flights, the perks are worth the annual fee (currently $650). You will earn SkyMiles® with all purchases as well. This is the card I primarily use in my business now.

With the Reserve Card you'll get 125,000 miles after spending $15k in the first 6 months of card membership.

DISCLAIMER: Program benefits may change at any time.

Full disclosure: By using this referral link, you will receive 125,000 Delta Miles when you spend $15,000 in your first six months of membership. Highest bonus AmEx has offered with this card ever! When you sign up, I will receive 25,000 miles as well.

The above information is subject to change at anytime with American Express & does not constitute financial advise. Please be wise when choosing to utilize credit for your business.


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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