Blog
My big take on economic things
It’s not just politics or headlines—growth has slowed, uncertainty is creeping in, and spending behavior is shifting. If you run a business, now is the time to plan carefully. In this post: hiring your kids, high-value marketing ideas, must-know deadlines, and what to watch in the economy for the next 18 months.
Should you hire your kids?
When is it time to put your kids on the payroll? If you run a family business, hiring your children can be a great way to teach life skills, unlock tax savings, and start building their retirement savings early. Here’s how to do it right—and what you need to know first.
When it’s time for the next chapter
If you’re considering stepping back from the business you built, this post shares a thoughtful resource from Andrea Carpenter to help you navigate the emotional and strategic sides of succession—whether your exit is years away or already in motion.
The drunken elephant in the room
From drunk elephant metaphors to a CRM Bootcamp and reclaiming joy at work—this newsletter has everything you need to kickstart your 2026 planning with a sense of humor and a solid foundation.
Make space for joy
Sometimes growth looks like strategy. Sometimes it looks like laughter at a Taylor Tomlinson show. This post is about both—plus one client’s path to the Inc 5000.
I’ll OBBB right back
A car accident, a tax bill that broke my heart, and a real week off changed how I’m approaching this moment. Here’s what small business owners need to know now—and why it’s okay to pause before planning.
Let’s go to the tape
Ten years, zero missed payrolls, and one life redesigned: Jill James shares what she’s learned from building a business that puts people first and why staying in the game is the greatest milestone of all.
Elvis liked boring rollercoasters
Ten years, zero missed payrolls, and one life redesigned: Jill James shares what she’s learned from building a business that puts people first and why staying in the game is the greatest milestone of all.
Oops, it’s my 10-year anniversary
Ten years, zero missed payrolls, and one life redesigned: Jill James shares what she’s learned from building a business that puts people first and why staying in the game is the greatest milestone of all.
A sparkly shared future
Your business doesn’t fit in a box—and your marketing shouldn’t either. Jill James explores why future potential doesn’t always conform to tidy positioning, and shares how her team supports founders through messy, meaningful growth.
My big take on economic things
It’s not just politics or headlines—growth has slowed, uncertainty is creeping in, and spending behavior is shifting. If you run a business, now is the time to plan carefully. In this post: hiring your kids, high-value marketing ideas, must-know deadlines, and what to watch in the economy for the next 18 months.
Should you hire your kids?
When is it time to put your kids on the payroll? If you run a family business, hiring your children can be a great way to teach life skills, unlock tax savings, and start building their retirement savings early. Here’s how to do it right—and what you need to know first.
When it’s time for the next chapter
If you’re considering stepping back from the business you built, this post shares a thoughtful resource from Andrea Carpenter to help you navigate the emotional and strategic sides of succession—whether your exit is years away or already in motion.
The drunken elephant in the room
From drunk elephant metaphors to a CRM Bootcamp and reclaiming joy at work—this newsletter has everything you need to kickstart your 2026 planning with a sense of humor and a solid foundation.
Make space for joy
Sometimes growth looks like strategy. Sometimes it looks like laughter at a Taylor Tomlinson show. This post is about both—plus one client’s path to the Inc 5000.
I’ll OBBB right back
A car accident, a tax bill that broke my heart, and a real week off changed how I’m approaching this moment. Here’s what small business owners need to know now—and why it’s okay to pause before planning.
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Running a company is hard. My weekly newsletter makes it easier. Each Wednesday, I write about strategy, general management, and finance issues and trends specific to the needs of you, the founder / CEO of a self-funded company.