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The 1099 You Shouldn’t Send: The Summer Hiring Mistake That Follows You Into April

Jun 5, 2026 | Contracts, Documents, Independent Contractors, Risk Management, Small Business, Workers

Every summer, the same pattern plays out. Business picks up, the calendar fills, and the college student you know becomes your part-time social media manager. A retired professional takes on some overflow bookkeeping. A contractor handles the work your team...

Your Mid-Year Business Check-In: 5 Things to Review Before Summer (and One Deadline You Cannot Miss)

May 22, 2026 | Documents, Independent Contractors, Insurance, Risk Management, Small Business, Structure, Taxes

Mid-May is a natural pause point. Q2 is not over yet. Summer has not fully taken hold. You still have time to catch and fix the things that are easier to address now than in December. Here are five things worth reviewing before summer arrives. Your Estimated Tax...

Before You Load the Car: What Your Business Needs Before You Leave for Summer Vacation

May 15, 2026 | Documents, Risk Management, Small Business, Successor

The cooler is packed. The kids are arguing over the back seat. Your partner has already asked twice whether you remembered the sunscreen. You toss all the bags in the trunk, do one last check of the locks, and climb in. Somewhere between the driveway and the highway,...

Your Business Runs Because You Show Up. Here’s What Happens When You Can’t.

May 8, 2026 | Documents, Growth, Risk Management, Small Business, Successor, Taxes

For a few weeks every spring, tax season gives you more financial clarity than almost any other time of year. Now ask the question most business owners never think to ask during that window: What happens to all of this if you can’t show up tomorrow? Not because you’re...

The Agreement That Controls Your Business – Even If You’ve Never Read It

Apr 23, 2026 | Contracts, Contracts, Documents, Risk Management, Small Business

Whether you have an LLC with an operating agreement or a corporation with a shareholder agreement, the stakes are the same. The names are different, but both documents do the same essential job – and in this article, we’ll cover the principles that apply...

How to Recession-Proof Your Business: Strategies That Survived 2008 and 2020

Apr 16, 2026 | Economy, Risk Management, Small Business

You watched it happen twice. In 2008, businesses that seemed rock solid were suddenly gone. In 2020, companies that had been operating for decades shuttered in a matter of weeks. And in both cases, the owners who lost everything weren’t necessarily doing...
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Recent Posts

  • The Question Every Father Thinks He’s Answered (But Hasn’t)
  • The 1099 You Shouldn’t Send: The Summer Hiring Mistake That Follows You Into April
  • Who Would Raise Your Kids If You Couldn’t? (What You Don’t Know About the First 72 Hours)
  • Do You Know Your Q3 Number? Most Business Owners Don’t, and Summer Is Why
  • No One Warned Her About the Widow Penalty. Her First Tax Return Did.

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