2Bobs in Tuscany
Join David, Blair, six other business owners and their spouses for four days and nights of creative business exploration in an intimate countryside villa designed for long meals, deep conversations, and unhurried thinking.
Light programming, deep conversations
This is not a conference, mastermind, or sales event. It is a small gathering for thoughtful owners of creative businesses who want to think more expansively about work, life, and the role they play in both.
Each day begins with a beautiful breakfast sourced from the local countryside and an optional morning discussion. After that, the day is yours. Read. Write. Rest. Explore. Talk with the Bobs or the other participants. Bring your spouse and let the setting do some of the work.
In the evening, everyone reconvenes outdoors for dinner at a communal table. Afterward, the optional salon invites wider conversation on business, life, and the things that deserve more thought than our normal calendars allow.
Retreat or Advance. It's Up to you.
Use the free time to recharge and socialize or to dive deep with your peers into your most pressing business issues.
Breakfast
Each day starts with a catered breakfast shared at an easy pace.
Morning Topic
David and Blair lead an optional 90-minute discussion on one focused business theme.
Open Day
Relax by the pool, work on your book, talk with others, or explore the countryside.
Dinner + Salon
Chef-prepared dinner is the only daily commitment, followed by an optional evening salon.
Set and Setting
The villa gives the retreat its tone: private, generous, and quietly luxurious without being ostentatious.
Everything is handled once you arrive
$7,000 USDPer person
$8,500 USDFor couples
Accommodations, food, and beverages are included. You simply need to get yourself there.
- Four days and nights in a nine-room villa in the Tuscan countryside
- Breakfast each morning, lunch during the day, and chef-prepared communal dinners
- Optional morning discussions and evening salons with David and Blair
- Rooms with double beds and private bathrooms
- Participation for spouses, whether or not they work in the business
“You have as much to contribute as you do to learn.”
Owners with range
- You own a creative business and can contribute meaningfully to the discussion.
- You have interesting interests outside of work, perhaps even weird ones.
- You enjoy food, communal meals, and the culture of a place like Tuscany.
- You are comfortable with open conversation, including disagreement without theater.
- You can commit to attending for the full duration of the retreat.
An easy arrival from Rome
The ideal trip is to arrive in Rome on Monday, spend the night there, and then make your way to the villa on Tuesday. By rental car, the drive is about two hours if you go straight through, longer if you prefer to take your time through the countryside.
For guests who prefer not to drive, group transport will depart from Rome’s Leonardo da Vinci International Airport (FCO) at 2:00 PM on Tuesday, September 15, 2026, with return transport on Saturday, September 19, 2026, timed to reach the airport for 11:00 AM.
Request your place
Applications are considered in the order received. This is not a rigorous vetting process, but we do want to make sure each guest fits the spirit of the retreat. Once accepted, you will have 48 hours to pay for your spot. All sales are final, though if you need to cancel, we will try to fill your place and refund you only if we are able to.