Agency build Active
We Insure Things
A modern insurance agency focused on making coverage easier to understand, faster to access, and less painful for customers and agents.
Founder file 001
Insurance operator. Systems builder. Problem collector.
I build insurance businesses, teams, practical tools, and training systems for the messy middle — the place where sales, service, compliance, technology, and real human problems all collide.
operator desk
On the desk · Aug 3, 2026Shipped the /thoughts page. Field log 01 — “Insurance is emotional before it is technical” — is live. Next up: field log 02.
operating log
> build agency systems
> simplify insurance language
> train better producers
> type 'help' and hit enter
The short version
I like building useful things in boring industries.
Especially when the boring industry is actually important.
Insurance is full of complicated forms, old workflows, confused customers, overwhelmed agents, and tools that somehow make the day harder. That is the kind of mess I like working on.
My work is part agency building, part sales operations, part training, part technology experimentation, and part “there has to be a better way to do this.”
Most of my best ideas start as messy problems customers, agents, or business owners keep running into over and over again.
Open case files
Things I’m building, testing, or thinking through.
Some of these started as a half-annoying customer problem, a clunky workflow, or a weird domain someone should have bought. These are the tabs I keep open.
Lead site Experiment
WeInsureShit
A blunt, trust-first lead-matching experiment: plain language, clear promises, less friction, and humor that earns trust instead of clicks.
Education Building
Free license school
Free licensing and study tools that help new agents understand the material instead of memorizing random exam questions.
Media Experiment
WiT Radio
Brand media experiments, show concepts, and insurance-adjacent content that is less boring.
Tools + ops Building
Tools for operators
Simple calculators, templates, knowledge bases, and cleaner handoffs for small businesses and agency teams that need clarity more than complexity.
Community Idea folder
Local ideas
Projects and concepts around local business, community improvement, transportation, and practical public problem-solving.
“The best systems feel obvious after someone finally builds them.”
That is usually the goal: take something confusing, turn it into a process, make it repeatable, then make it easier for the next person. In insurance, that can mean a better sales script, a cleaner form, a smarter training tool, or a customer experience that does not require a dictionary.
Field notes
Operating principles I keep coming back to.
Make the complicated part visible.
If nobody can explain the bottleneck, nobody can fix it. Draw the messy process first.
Train the human, then improve the system.
Bad process plus new tools is just faster confusion. Fix the workflow before adding more layers.
Plain language wins.
Customers do not need insurance theater. They need clarity, options, and next steps.
Useful beats impressive.
The best business tools are the ones people actually use when the day gets busy.
Build map
A career built in the field, not just on paper.
This is the résumé section, but rebuilt like a map: less corporate biography, more proof of what has been built and learned along the way.
01
Learned the work close to the customer.
A decade of retail and operations management — ending at Aramark, running multiple Starbucks locations with 28 direct reports. Sales, service, and leading teams under daily pressure.
02
Learned insurance from the sales seat.
A 1,300-client book as a State Farm sales associate, then life insurance production at a Williamsburg agency. The licenses, the objections, the real conversations.
03
Built an Allstate agency — then made it one of Virginia’s largest.
Grew sales from $2.8M to $7.6M through three acquisitions, a hiring and training system adopted nationwide, and a top-3% Allstate ranking — then sold the agency profitably.
04
Founded a modern insurance agency.
Built We Insure Things around broader access, digital-first workflows, practical advice, and a less painful customer experience.
05
Combining insurance, education, web tools, and media experiments.
Developing training tools, lead funnels, media concepts, and business resources that make insurance and operations easier.
Receipts
Proof without the corporate humblebrag fog.
Agency growth$2.8M → $7.6M
Sales at Wease Financial, the Allstate agency I built in Williamsburg, VA — then sold profitably.
Close rate15% → 27%
Nearly doubled by switching the team to value-proposition selling. Highest in the organization.
Allstate rankingTop 3%
Agency recognition nationwide — the Honor Ring plaques below are the hardware.
National keynote~1,300
Agents in the room when the hiring and training playbook was shared as a best practice.
Grew an Allstate agency into one of the largest in Virginia — through three acquisitions, one with no money down.
Built a hiring and training system that turned 15 new hires into $1M+ of revenue — adopted by agencies nationwide.
Reversed team attrition 75% in three months by fixing roles and workflows, not adding meetings.
Co-chaired a national advisory board and helped shape a Trusted Advisor dashboard rolled out enterprise-wide.
Created digital quote funnels and insurance web projects.
Turned weird internet ideas into practical business assets.
Field logs
Notes becoming essays, one at a time.
Field log 01 · publishedDraft 02
Draft 03
Draft 04
Draft 05
Draft 06
Open the thoughts page
Insurance is emotional before it is technical
People usually come to insurance because something changed, broke, grew, or scared them.
Read it →Training agents for the real conversation
The exam matters, but the customer conversation is where the work becomes real.
Why most agency websites are boring
And what happens when you make the customer feel like a human instead of a form submission.
Lead sites without the bait-and-switch
How to collect leads transparently without selling people into the internet blender.
Small business owners need simpler tools
Most operators do not need more dashboards. They need clearer next steps.
The weird idea folder
A place for concepts that sound ridiculous until the practical use shows up.
The lab
What I’m useful for.
Bring me the messy middle.
I’m most useful when a business has motion but needs better systems: sales process, training, accountability, lead flow, customer communication, or technology that should make the work easier but currently does not.
Agency
Growth and operations
Sales process, producer training, service workflows, accountability, and practical agency systems.
Tech
Insurance tools and automation
Quote funnels, internal tools, knowledge bases, cleaner forms, and better customer handoffs.
People
Training and communication
Making hard concepts easier to explain, teach, sell, and repeat.
Ideas
Weird but practical projects
Concepts that are memorable, useful, and more human than the default industry version.
Media kit
Need the polished version?
The rest of this page is the working file. This is the clean drawer: short bio, project links, and a simple way to start a real conversation.