Jonathan Duckworth
Problem Solver
Jonathan Duckworth
About Me
I take work seriously without taking myself too seriously — those are two different skills, and most teams do better when both show up at once. I’ve spent most of my career running or working inside small businesses: a pizza shop, a small coffee chain, various other ventures, and currently my family’s own investment operation. The common thread is that I genuinely enjoy moving good ideas from a notebook into reality, working with people in a way that respects the experience already in the room, and representing a brand the way I would want my own represented. I like solving problems that matter, executing instead of theorizing about execution, and leaving things a little better than I found them.
- Residence Anchorage, Alaska USA
- Email Contact@JonathanDuckworth.com
- Phone 1-877-878-2761
What I Do
Testimonials
The following testimonials are fictional. They are not endorsements, references, or evidence of sound professional judgment. They are included solely because life is short and a completely serious testimonials section felt a little too self-important.
Jonathan has proven to be an invaluable asset to our company. His innovation in creative accounting helped us unlock bold new financial possibilities that regulators had previously insisted were "not real." Thanks to his visionary work with special purpose entities, we were able to achieve astonishing paper success right up until the entire thing burst into flames.
Jonathan's strategic insight helped us stay focused on what truly mattered: the in-store movie rental experience. While others were distracted by fleeting trends like convenience, digital delivery, and the future, he encouraged us to double down on late fees and physical locations. That kind of commitment to the past is rare.
Jonathan brought a powerful understanding of customer needs to our organization. Under his guidance, we refined our staffing philosophy to ensure shoppers enjoyed the thrill of wandering the store with absolutely no help whatsoever. His ability to align operational decisions with long-term disappointment was nothing short of remarkable.
Resume
Experience
2022 - Current
Duckworth Holdings LLCDirector of Fiscal Strategy
For the last several years, I have been responsible for managing and growing my family’s assets (something I have done throughout my marriage, even if not in a formal incorporated capacity)— stock options, real estate, and the ongoing work of keeping our operating businesses healthy. It’s not as glamorous as it sounds on paper and about twice as stressful, because when the money you are allocating is your own family’s, the spreadsheets stop being abstract and start feeling like a 2 a.m. problem.
What I have learned in this seat is that patience and risk discipline quietly beat cleverness almost every time. The goal is not to produce exciting returns; the goal is to still be in a position to make good decisions ten and twenty years from now — which turns out to be a harder discipline than chasing the next thing.
- Capital Allocation
- Risk Management
- Real Estate
- Long–term Strategy
2023 - 2026
Duckworth Coffee LLCBusiness Owner (Multi–Location Cafe)
For several years I owned and operated multiple coffee shops in Anchorage. One shop is a business. Two shops, you quickly learn, is a completely different business. The habits that worked when I could keep an eye on every transaction myself — “I’ll just handle it” chief among them — stop scaling the moment there is more than one front door to walk through.
The main thing I took from the coffee business was the value of surrounding yourself with people who are better than you at the things you are worst at. A huge amount of what worked belongs to our Operations Manager, whose leadership is most of the reason the second, third, and fourth locations did not quietly eat the first one alive. Delegation is a skill you either learn early or learn expensively. I learned it in the middle.
- Multi–location Operations
- Delegation
- Team Leadership
- P&L Management
2019 - 2024
AK Pizza LLCOwner Operator (Pizzeria)
This was easily my favorite venture, and without question the most demanding. The first year or so was fourteen–hour days, seven days a week — which is, if nothing else, an incredibly thorough audit of every weak spot in a small business (and a few personal ones besides). By year five, the same shop ran on systems instead of heroics.
Most of the improvement came from unsexy work: simplifying the menu and recipes to protect quality and margins, building a direct online ordering platform to reduce our dependence on delivery apps taking 30% of every ticket, and standardizing the things that could be standardized. Standardization was the quiet winner. It’s not flashy, but it’s how you make a pizza someone loved yesterday taste exactly the same tomorrow — and that sameness is most of what loyalty is actually made of.
- Operations
- Menu Engineering
- Custom Software
- Standardization
TGM (Training General Manager)
Several years with Papa Johns in the Southeast, ending as a Training General Manager. The job was a front–row seat to how franchise restaurants actually work — which is to say, how they work beautifully on paper and then collide with real people, real schedules, and real Saturday–night rushes.
Training incoming GMs turned out to be one of the better teachers I have had. You cannot explain a system well if you do not actually understand it, and you find out very quickly which parts of your own playbook are real knowledge and which parts are muscle memory. It sharpened my ability to teach, diagnose, and spot the gap between “what the manual says” and “what the store is actually doing.”
- Franchise Operations
- Training & Development
- People Leadership
- QSR
Combat Medic
My time as a Combat Medic was, honestly, not my favorite chapter — but I walked out with a set of habits I still use every day. The big one is staying calm when the situation is not: being the person in the room whose pulse does not spike when everyone else’s does. That is a learnable skill, and the Army is a very effective, if not especially gentle, classroom for it.
It also gave me an early appreciation for making real decisions with incomplete information, fast, and living with the consequences afterward. My wife likes to tell people I developed something of a God complex during my medic days, which is probably unfair — but not completely baseless. Ten out of ten for character development. I would not do it again.
- Emergency Medicine
- Decision Under Pressure
- Triage
- Discipline
Random Jobs
Before and between the ventures above, I have worked in a wider spread of industries than any resume template really wants to accommodate. The range runs from cleaning toilets for the Kotzebue IRA while my daughter attended Nikaitchuat, to selling life insurance for Liberty Mutual, with several unrelated stops in between.
It’s not the world’s most linear path, and it’s most of the reason I can walk into almost any workplace and be useful in short order. A little bit of everything builds a particular kind of pattern recognition — one that notices what is actually going on in a business regardless of what industry it happens to be in. There is a specific kind of confidence that comes from having cleaned a real bathroom for a real paycheck, and I would not trade it.
- Adaptability
- Sales
- Customer Service
- Pattern Recognition
Projects
Blog
Welcome to the blog. Think of it as the lowest–friction way to get a read on how I actually think, without either of us having to commit to a long coffee meeting first. The posts here are the pieces of my thinking that don’t fit cleanly onto a résumé — opinions I’ve formed, lessons I’ve learned the hard way, and the occasional topic most professional bios quietly avoid. You won’t find a lot of hedging. You’ll find honest writing, the occasional firm view, and a tone that leans more conversational than corporate — which is, I’d argue, how people talk when they actually have something worth saying.
