Founders Retreat: What It Is, What It Costs and How to Choose One
By Byron Dempsey · 5 min read · Updated October 2026A founders retreat is time away from your business, usually a few days to a week, where founders step back to rest, think clearly about where the business is going, and spend time with people who understand what building something is really like.
The three kinds of founders retreat
Most retreats sold to founders fall into one of three camps. Each has its strengths.
Wellness retreats. Yoga, healthy food, massages and rest. Great for recharging, but the business barely comes up.
Business retreats. Strategy sessions, masterminds and workshops. Useful, but often everyone is on their laptop the whole time, so you never really leave the business.
Holiday-style retreats. Golf, quad biking, boats and big nights with other founders. That's still fun, but it's essentially a holiday with people.
In my experience the magic happens when a retreat does all three: it looks after your health, it works on the business, and it works on you as a person.
What makes a founders retreat actually change something
The difference between a retreat that changes someone and a nice week away comes down to three things.
The people in the room. You'll learn as much from the other founders as from any session, so who else is there matters more than anything.
The facilitator or host. Someone who has done this many times, knows how to hold a group, and can get people talking about what really matters.
What you actually do. Activities that push people a little and create real conversations, not just things to fill the day.
Is a founders retreat right for you?
Not everyone is ready for one, and that's fine. You're probably not ready yet if:
You're just starting out. In the first year or two, your time and money are better spent on getting the business working.
You're full of energy and crushing it. If you don't want time off right now, a retreat will feel like it's getting in the way.
You just want to relax. A founders retreat means doing personal development and business development. If you just want to switch off, a wellness retreat or a holiday will suit you better, and both will cost less.
What a founders retreat costs
Prices vary a lot. Community events and long weekends can be cheap or even free for members, while a week overseas with accommodation, meals and facilitation runs into the thousands.
What drives the price is how long it is, where it's held, the quality of the venue, how small the group is, and what's included. Check whether flights, rooms, meals and activities are in the price before you compare.
Questions to ask before you book
Look at the venue, but most importantly look at the people and the host. That's the most important thing.
Who is the host, and what experience do they have? How many retreats have they run, and how long have they been doing it?
Who are the other people going? Are they at a similar stage to you, and are attendees screened?
Who have they worked with before? Look for past attendees you can see, and what those people say about it.
What do their photos look like? Real photos from past retreats tell you a lot about the venue, the group and the energy.
Do they consistently fill their retreats? A host who runs them regularly and fills them has a track record. Ask whether it's a one-off.
How good is the venue? You'll spend a week there. It should feel like somewhere you can actually switch off.
How we run ours at Driven Young
Our Founders Retreat is built to do all three. Seven days in a private villa in Canggu with 20 founders in their 20s and 30s. Phones go away on day one. Mornings are breathwork, yoga, ice baths and the sauna. Days are business strategy, systems, AI and marketing, done with pen and paper around a table. There's a sunrise volcano hike, a private chef, and plenty of time to think. People leave with a clear 12-month plan and a group of founders who get it.
What past founders say
"Exactly what I didn’t know I needed. A reset, a push, and a room full of people who just get it"
"What you think your going to get out of this, multiply it by ten and you will come close to what this retreat will do for you."
"Life's too short, so you should be going for the Driven Young retreat so you can reclaim that lost time. It truly opened my eyes to the possibilities."
Frequently asked questions
What is a founders retreat?
A founders retreat is time away from your business, usually a few days to a week, where founders step back to rest, think about where the business is going, and connect with other founders. The best ones combine wellness, business and personal development.
How much does a founders retreat cost?
It depends on length, location, venue, group size and what's included. Community weekends can be cheap or free for members; a week overseas with accommodation and meals runs into the thousands. Ours starts at $4,999 + GST with everything included except flights.
What is the difference between a founders retreat and a wellness retreat?
A wellness retreat focuses on rest and recovery. A founders retreat should also work on your business and on you as a person, with other founders in the room. If you only want to relax, a wellness retreat will usually cost less.
Who should go on a founders retreat?
Founders who have an established business, have been heads down for a while, and are ready to step back and work on both the business and themselves. If you're just starting out, it's probably too early.
How do I choose a good founders retreat?
Look at the host's experience and track record, who the other attendees are, photos from past retreats, whether they consistently fill their retreats, and the quality of the venue.
How do I join the Driven Young Founders Retreat?
It is application only for established business owners doing $100K+ in revenue. Fill in the two-minute application, then we have a short call to make sure it suits you and the group.