He's had to
make payroll
Most interviewers are interviewers. Ryan is an operator who happens to hold the microphone, and it changes what gets asked. He knows where the bodies are buried in a P&L because he's buried a few himself.
He started in hotel accounting in 2000, at the bottom of the finance office, learning the business the way it is actually learned — by closing the books on it every month.
In 2003 he left to become CFO and owner of a manufacturing business in Simi Valley, California, which is a fast way to find out that the numbers on a statement are decisions somebody already made, and usually not the ones you'd have made.
Then back to hotels, and he stayed seventeen years. Assistant Controller and IT at the Chateau Marmont — one person, both jobs, because that's how it works at a property that size. Six years as Director of Information Technology at The Fess Parker in Santa Barbara before moving across the hall into finance. Then hotels at scale: the Hilton Anatole in Dallas, The Madison in Washington DC, and four years as Director of Finance at Hilton Dallas/Plano Granite Park.
He ran the systems a business depends on and the numbers it produces. Most people pick one.
In 2022 he became steward of a tax practice with forty years of history and founded Taxsmithing inside it. Today he runs four companies across tax, hospitality and software — and feels the consequences of every structural choice in his own cash flow.
The software came last and inevitably. He'd need something inside one of the businesses, go looking, find nothing good enough, and build it. That pattern repeated often enough to become Dayspring IdeaForge, his AI creation company. The first customer was always him, with his own money on the line, which is a very effective way to find out whether software is any good.
The short version
- Based in Allen, Texas
- Main Street Certified Tax Advisor (MSCTA)
- In hotel finance since 2000 — twenty years inside the industry
- Six of them as a hotel Director of Information Technology
- Steward of a 40-year-old tax practice since 2022
- Founder of Dayspring IdeaForge, four platforms shipped
- California Lutheran University
What he likes talking about
AI in small business — not as a topic, but as something you shipped on a Tuesday and had to fix on Wednesday.
How he interviews
Three habits that shape every episode.
He goes first
It's difficult to ask someone to be honest about a failure from behind a wall of your own highlight reel. So he opens his own books first.
He reads up
Your business, your writing, your last five interviews — specifically to avoid the questions you've already answered forty times.
He asks the second question
The follow-up that only occurs to someone who has actually had to live with the answer.
I've been wrong in my own books and had to fix it.Why the second question lands
Beyond the show
Unfinished Empires is one of several things Ryan is in the middle of building. The rest live here.
Accent Financial
The tax and accounting practice, since 2022.
The Taxsmiths
Taxsmithing — artisan tax strategy and planning.
Dayspring IdeaForge
The AI creation company. Four platforms so far.
Dayspring Hospitality
Because he got tired of watching good operators get served by people who'd never worked a night audit.
Got an unfinished empire?
Every application is read by Ryan personally, and you'll hear back either way.