Personal finance for people who want to be great with money — written by the friend who already is.
LLCs, S-corps, retirement plans, succession — the money side of running something of your own, without the guru varnish.
The framework
Every small business owner eventually discovers the same truth: the business only scales as far as the four back-office systems can carry it. Get these right early and the rest gets much easier.
The right structure at the right revenue quietly compounds.
Sole prop, LLC, S-corp. The wrong choice at $250k is a five-figure annual tax.
A real bookkeeper is the highest-ROI hire most owners make.
If you don't know your margin by category, you don't know your business.
Salary, distribution, retirement contribution — pick the mix, don't drift into it.
The IRS has strong opinions here. So does your future retired self. Reconcile both, on purpose.
Every business has an exit — planned or otherwise.
Sale, succession, wind-down, or hand-off. Deciding early makes every operating decision cleaner.
Voices on this desk
Joining soon
The CPA
Fifteen years at the Big Four, then five years running her own practice. Believes most people overpay taxes by five figures without knowing it.
Joining soon
The Family Office Advisor
Spent a career advising ultra-high-net-worth families. Believes the playbook translates further down the wealth spectrum than most people think.
Joining soon
The Entrepreneur
Bootstrapped two companies to seven figures. Writes about the money side of building something of your own.
On this desk
Jul 7
Issue #16
One number tells you the answer. Everything else is noise the internet added.
1 min read
Evergreen
Jun 18
Issue #17
For self-employed savers, the wrong choice quietly costs five figures a year in missed contribution room.
1 min read
Evergreen
Jun 9
Issue #28
The tax savings are real. So is the paperwork. The crossover point isn't where the internet says it is.
1 min read
Evergreen
The Desk Reads
Sources we track — not endorsements. The Smart Money reads widely and writes its own take. When a dispatch draws on one specifically, it's cited at the bottom.
Established sources
Program and rule changes.
Founder-shared numbers.
Founder interviews.
Bootstrapped SaaS economics.
Calm-company operating philosophy.
Mark J. Kohler — Main Street Business
The entity/S-corp/retirement-plan reference for owners.
State-by-state formation guides, free and precise.
SBA-partner templates and mentoring.
Small-business optimism and problem surveys.
Payroll, benefits, and owner-comp explainers.
Rising voices
Small Business Tax Savings Podcast
Mike Jesowshek — weekly tactical owner-level tax moves.
Taxes for creatives and solo owners.
Primary & data sources
The Seasonal Playbook source.
IRS Retirement Plans for Small Entities
Solo 401(k) vs. SEP rules and limits.
Follow just this desk
Just the Small Business Desk — the money side of running something of your own.
The weekly dispatch
The kind of financial advice you'd get from a friend who's already figured it out. No hot takes, no leaderboards, no affiliate hustle.