“But as for me and my house, we will serve the LORD.”

Joshua 24:15, ESV

Before anything else, here’s my compass. I’m a dad and a believer, and I’ve been carried more times than I can count by God’s grace and the people He put around me. Now it’s my turn to hold the rope for someone else. Everything on this page starts there.

Lift others while we climb.

WinsAI for the rest of us. See the wins on hammerkeellabs.com (opens in a new tab)

Sarasota, Florida

Chris Naylon

Dad, numbers guy, building this one step at a time.

Faith, family, freedom.

Read my story Meet Chris Connect
Illustration of a rope running up a mountain ridge, with the words Hold the rope, lift while we climb

About

A Florida finance leader who puts family first.

Chris Naylon (Christopher Naylon) is a finance executive. Chris spent nearly two decades in corporate finance at Allstate and has spent his career since in finance leadership in Southwest Florida. A native Floridian, he was born in Hollywood, Florida, and lives in Sarasota.

Chris is a two-time graduate of the University of South Florida. He earned a Bachelor of Science in Biological Sciences from USF in 1997 and a master’s degree in business from USF in 2003.

On the side, he builds AI bot skills through Hammerkeel Labs. Read Chris Naylon’s full bio and career timeline, or his own story of the last 26 days.

At home, Chris is dad to four sons, including two boys who play football, Jack and his younger brother, and he sums up what matters most in three words: faith, family, freedom.

Chris Naylon
  • 1997–2016Nearly two decades in corporate finance at Allstate
  • 2016–nowFinance leadership in Southwest Florida
  • ’97BS, Biological Sciences, University of South Florida
  • ’03Master’s in business, University of South Florida

Career

Nearly 30 years in finance.

Nearly two decades in corporate finance at Allstate (1997–2016), then finance leadership in Southwest Florida.

December 2016 · Present

Finance leadership

Chris has spent his career since Allstate in finance leadership in Southwest Florida.

1997–2016

Corporate Finance, Allstate

Chris built his career in corporate finance at Allstate, where he spent nearly two decades before moving into finance leadership in Southwest Florida.

1997 & 2003

University of South Florida

Bachelor of Science in Biological Sciences (1997) and a master’s degree in business (2003).

Hammerkeel Labs · What I’m Building

An ecosystem of AI bot skills, built one step at a time.

Hammerkeel Labs is my new project: a growing family of AI bot skills, the everyday helpers I’m building for my own household.

On Thursday, September 24, 2026, I signed up to build my first AI bot. Since then I’ve been building helpers for my own home, starting with our finances, then personal business, then health. It’s a build in progress, and I work on it every day.

Visit hammerkeellabs.com (opens in a new tab)

What I’m building · About Hammerkeel Labs

My Story · 26 days

September 24 to October 19.

Just a regular guy finding out what this stuff can do when you point it at your own life, and writing down what happens, good and bad.

  1. Sep 24

    The drive home

    Long drive home from St. Augustine, talking it through with Grok. Somewhere on that road I decided to actually learn this AI stuff.

  2. Sep 24

    Downloaded the app

    Same day. Started on my own stuff: email, money, health. Hit the limits within 48 hours.

  3. Week 1

    One bot, then a team

    First bot just cleaned up my Gmail. Then a boss, then research, health, money and faith.

  4. Sep 28

    Daily check-ins

    Started checking in on my health three times a day. Sleep, training, food. Simple boxes.

  5. Late Sep / Oct 1

    Logging it all

    Every workout since late September, then every meal too. I talk, the bot writes it down.

  6. Oct 1

    Wrote it down

    Wrote down every supplement I take. Couldn't name half of them off the top of my head.

  7. Oct 2

    Weekly check

    Started a weekly body-comp check. Same scale, same time. Not chasing a number, just the direction.

  8. Oct 13

    Garmin back on

    Sat in my truck's glovebox for over two years. Charged it, put it on. On my wrist every day since.

  9. Oct 14–16

    Rather know than guess

    First full blood panel and a glucose monitor, same week. At 52 I'd rather know than guess.

  10. Oct 15

    chrisnaylon.com

    Put up my own website. First one I ever built, if you count telling a bot what I wanted.

  11. Oct 19

    About #4

    Search "Chris Naylon" and a California realtor owns the top spots. I'm about #4 now. Coming for you, buddy.

  12. Oct 19

    First find

    One of the bots found a bill sitting on the wrong card. Right in front of me the whole time.

Read the whole story · Full timeline

FAQ

Who is Chris Naylon?

Chris Naylon (Christopher Naylon) is a finance executive and the builder behind Hammerkeel Labs. He is a native Floridian, born in Hollywood, Florida, who lives in Sarasota. He is a two-time University of South Florida graduate. Chris spent nearly two decades in corporate finance at Allstate and has spent his career since in finance leadership in Southwest Florida.

More questions and answers → · Timeline →

Planning an event, panel or podcast? Chris welcomes speaking requests. Reach out on LinkedIn (opens in a new tab).

Insights

Recent posts from Chris

Short notes Chris has shared on LinkedIn, X and Instagram, and here.

More insights from Chris Naylon →

Family & Faith

Faith, family, freedom.

Faith and family are at the center of Chris’s life. He is a grandfather and the proud dad of four sons.

“Blessed and highly favored.”

Jack Naylon

#55 · Center

Cardinal Mooney Cougars

Committed to Lehigh

The little brother

Another football player in the family

Connect

Connect with Chris

Follow along for faith, family, football and finance.