Our entire industry has gotten turned upside down…

Creating opportunities like never before.

Are you ready to stake your claim and set yourself up for the rest of the decade?

Then I invite you to join me for a live event November 11-13, 2024, in the heart of historic Savannah, Georgia

Deep Dive Savannah is my 3-day in-person business (and life) experience where you will:

  • Get clarity on your business
  • Go deeper on where you are and where you’re going
  • Revel in this beautiful “Hostess City of the South” with new friends

This isn’t a total makeover, rebrand, or shift in a whole new direction (unless you want it to be). 

It’s more about some small and subtle changes you can incorporate into your current model.

“Great event, Steve! I definitely came away with clarity. I’d encourage other Cafe members to take you up on these gatherings. The in-person exchange of ideas really makes a difference.”


— Dave Rynne, Sales Enablement Writer, after May 2023 event in Boston

No matter where you are now, Deep Dive Savannah will help you create a more peaceful, profitable, and enjoyable business. 

 

A business where you bring people into your world instead of going into theirs. 

A world of your own creation unlike anyone else’s.

“I went for one reason: to meet Steve Roller in person. I came away with enough insight to move my business from Q2 2023 through 2025, at least! There’s something special about sitting in front of other people at a dedicated conference with like-minded business owners and Steve’s guidance as an advisor and business owner.”

— Steph Gonzales, owner of Broker Summaries, based in Portland, OR

It’s a fun (and very profitable) place to be!

Best part? You can learn these things over three days. Seriously. It may take longer for the mental shifts to sink in, and it will take some time to implement the ideas and start seeing results (weeks or months, not years).

But even if you proceed slowly, and even if you only incorporate one or two things you learn at Deep Dive Savannah, I promise you this:

Your business — and life — will change for the better. You will:

  • Discover untapped opportunities others aren’t even thinking of yet
  • Get clear on what you should and shouldn’t be doing
  • Let go of physical and mental blocks holding you back from your full potential (even before you head home from Savannah)
  • Define what “your world” looks like for you
  • Learn new ways to bring people into your world (both business-wise and personally)
  • Get on-the-spot feedback from me and your fellow attendees which many have told me is the most valuable part of the experience
  • Figure out what your exact next steps should be
  • Have an opportunity to share your plans and goals with a small group of people (including me) who will encourage you, help you, and keep you accountable
  • Make some decisions to put you on a new upward trajectory
  • Learn how to be seen and get paid as an Advisor

Sometimes we need to get away from the distractions of home to think clearer and map out an action plan. Deep Dive Savannah is the perfect place to immerse yourself in some deeper business and life planning.

Also, a side bonus: This is going to be a really sharp crowd! Seriously, there’s nothing like swapping ideas and rubbing elbows with fun, upbeat, intelligent creatives. That alone is worth more than the price of admission. You’re my kind of people.

“This was a super-connected and dialed-in group (Boston 2023). Everyone contributed. Each was willing to air their insecurities, offer their experience rather than their advice, and above all, stay positive and encourage each other on. This event formed a bond between the group that will undoubtedly reach into the future.”

— Alan Steacy, Copy Clean-Up Specialist

Yes, Steve, I'm in!

Join Us at Deep Dive Savannah

Who is Deep Dive Savannah for?

Anyone who wants to grow their business in a simple, straightforward way in 2024 and beyond. Anyone who realizes that what got us here won’t get us where we want to go. 

And…if you’d like to move into the realm of getting paid more for your ideas, advice, and counsel than for what you actually deliver, this is definitely for you.

This is the 18th live event I’ve hosted, and the second Deep Dive Savannah event in my new home state of Georgia. I couldn’t be more excited to have you!

Leanne Rumsey said this about the one she attended in Santa Fe:

“The experience with this small group was nothing short of a high-level mastermind or brainstorming event that other people would have paid tens of thousands of dollars to participate in and attend.”

Don’t worry, I’m not taking Leanne’s pricing suggestion (yet). The Deep Dive Savannah Early Bird price is still only $1,200. 

Why now?

I scheduled this for the fourth quarter so you can get situated at the end of the year and put together a fantastic 2025.

It’s also a great time to visit Savannah and make a vacation out of it. It’s after Savannah’s super busy month of October, so the crowds are gone and the weather is still really nice, great for exploring the historic areas of this very walkable city.

Why in person instead of a virtual event?

Something magical happens when you get together in person. The ideas take hold better, and the memories seem to stick. More than anything, the follow-through has a much better track record. For whatever reason, people actually act on the ideas and make them pay off. I take no credit for that, it’s just part of the experience. I absolutely love hosting live events, which is why I keep doing them! 

Gary Wright, a past attendee, said:

“The small size makes it easier to share our stories and create a bond that would be hard to replicate in a larger group. Steve’s relaxed style and willingness to give is evident through the whole retreat experience. I would definitely recommend it to those who are serious about improving their business.”

And I got this message from Anton Volney six months after he attended one of my retreats in Vermont:

“Happy story! I just landed a full-time Senior Copywriting position with Ramit Sethi at IWillTeachYouToBeRich.com. This puts me on track to AT LEAST double my income this year.

“As far as I’m concerned, the breadcrumb trail that led me to this position started with Steve’s retreat four months ago. I’m very happy I decided to come.”

Savannah info and event schedule

I picked Savannah for a few reasons. 

It’s one of my favorite cities in the country, and only a few hours from where I now live. It’s called the “Hostess City of the South,” and you’ll quickly see why it gets that nickname. The people are some of the friendliest I’ve ever encountered, and Savannah has a nice, relaxed vibe that feels much different than most big cities.

If you like history like I do, you’ll love Savannah’s Historic Landmark District. It’s highlighted by 22 park-like squares, 19th century houses, and historic landmarks dating to the Revolutionary War on nearly every corner. 

We’ll be at the upscale Planters Inn where I’ve secured a special room block rate (see below under Travel Logistics). The hotel is on Reynolds Square, where we’ll be only a few blocks from bustling River Street along the Savannah River and within walking distance of Forsyth Park, Bonaventure Cemetery, and everything in the historic district.

Photo credit: Planters Inn

We’re going to kick things off at 9 am on Monday, November 11, on the 7th floor of Planters Inn at 29 Abercorn Street. It’s a great space with a nice view, and we’ll be around an executive boardroom table befitting of the Big Ideas we’ll be generating!  

You’ll want to arrive sometime the day before (Sunday, Nov 10) to settle in and maybe see some sights before we get started on Monday. 

I’ll give you a detailed agenda when you arrive in Savannah. 

Please note: This is a full day more than the Boston event I did in May of 2023. I wanted to have more time to cover everything and more time to spend time together at a relaxed pace. We’ll take a two-hour break for lunch (on your own) and that evening we’ll have dinner together at a nice restaurant of my choosing. The evening will be social and fun.

We’ll get back down to business Tuesday morning at 9 am, go all day until 5 pm with a two-hour lunch break again, and have another dinner together, either along the Savannah River or somewhere in the historic district (walkable from our hotel).

Photo credit: Planters Inn

The style of the retreat will be part teaching, a lot of interaction and sharing of ideas, and some rolling-up-the-sleeves work knocked out on the spot. The style will be friendly and casual, with plenty of opportunities to ask questions, offer your own ideas, and receive feedback from others. You’ll also have some down time to process everything and think, as well as take in everything Savannah has to offer, either alone or with the group.

Feel free to explore the neighborhood on your own early in the morning, at lunchtime, and before and after dinner. (Both Wednesday and Thursday night’s dinners are included in your Deep Dive Savannah experience.)

On Wednesday, November 13, we’ll start at 9 am again and finish at 1 pm. We’ll work through a couple more key points, complete an exercise that some past attendees considered the highlight of the event, and give this phenomenal event a proper send-off.

But wait…there’s more!

I highly recommend staying for the rest of Wednesday and leaving either Thursday or Friday. If you can stick around and hang out with us, I have some good social and sight-seeing fun planned. 

You’ll get a detailed agenda when you arrive, and I’ll send you more information between now and then. 

Travel logistics

If you live in the Southeast within a few hours of Savannah, consider driving. There’s a parking garage right next to the hotel for $25/day ($30 if you add it to your room bill) and you probably won’t need it for the three days during the event. Then you can leave at your leisure and maybe see things on the way home. Georgia is gorgeous in early November.

Further out? Fly to Savannah (SAV), Atlanta (ATL), Charleston (CHS) or Jacksonville (JAX). If you fly into Savannah you won’t need a rental car. Just Uber or taxi in and out. We’ll be walking everywhere on Wednesday, Thursday, and Friday.

Atlanta probably offers the best flight prices, but it’s also 3.5 hours away. Jacksonville and Charleston are each about two hours away. You’ll need a rental car if you fly into any of those three cities.

My recommendation? Plan to arrive early on Sunday, November 10, so you can soak up Savannah a bit before we start on Monday morning. I have a room block at Planters Inn for the nights of November 10, 11, and 12 (Sun, Mon, and Tues nights) for $152/night + tax. If you decide to stay on Wednesday night or longer, they may give you the same rate if you book it early enough. Book your room by calling 800-554-1187 and asking for the Steve Roller room block rate.

If you’re flying back, either make arrangements for early or late evening on Wednesday, Nov 13, or stay longer to enjoy the city. Planters Inn is 10 miles and a 17-minute drive from the Savannah airport.

What’s included?

Included: The event itself at Planters Inn plus dinner on Monday and Tuesday evening. There are a few places you can grab a quick breakfast within a block of the hotel, and you’ll be on your own for lunch on Wednesday and Thursday. 

Also: Big Ideas! Clarity. Feedback. Camaraderie. Fun! Laughter. Long-lasting friendships forged.

Not included: Getting to Savannah, your hotel room, and any sightseeing you do.

11 more things you’ll get at Deep Dive Savannah

  1. A newfound shift in the way you position yourself and operate your business.
  2. Client Conversation ideas to help you “sift and sort” and bring people into your world.
  3. The opportunity to come to this inaugural event in Savannah! Since this will most likely be the first of many in my favorite city in the South, I’m pulling out all the stops to make it extra special.
  4. Fun! Intermixed among all the business stuff, we’ll enjoy our time together. Savannah is a really fun place and a destination everyone should have on their list. It’ll be a blast, and we’ll also get to know each other better. I know from past experience that these events are often the start of strong friendships.
  5. In-person interaction with other sharp, like-minded people. Live beats Zoom any day.
  6. Big Ideas (from me and other attendees) that you might not have thought of on your own. Too often we work in a vacuum. It’s good to get amongst people who are making things happen!
  7. A possible metaphorical shot to the head (see Ed’s testimonial below).
  8. A chance to see an amazing, beautiful, historical city. One of the reasons I moved to Georgia is to be closer to Savannah. I feel at home here.
  9. Answers to any questions you have and feedback on your ideas.
  10. Time with me and the rest of the group. I can’t emphasize this enough! There’s nothing like hanging out with fun, sharp, interesting people. This is going to be one for the ages.
  11. Inspiration. There’s nothing like getting away from the distractions of home, enjoying a dynamic new environment, and giving yourself time to think, plan, and get reinvigorated. You’ll get a short-term kick in the butt and uptick in business. Even more, what you experience at Deep Dive Savannah will stay with you for life.

Event size?

With 17 live events under my belt since 2013, I’ve found the social and business interaction works best with about 10-15 people. Any more than that and I feel like I don’t get to spend time with each person. I want this to be a special experience unlike anything you’ve ever been to. It will be.

I’ve seriously considered Leanne Rumsey’s (and other advisors’) advice to raise the price considerably, but I also want to make this accessible to everyone who can make the trek to Savannah and is willing to put in the effort to apply what they learn. I don’t want this to be a “listen, take notes, and learn”-type seminar. This is an action event! It’s a time to take stock of where you are and where you’re going and make some changes

If you’re willing to do that, I’d love to have you. 

Savannah info and event schedule

I picked Savannah for a few reasons. 

It’s one of my favorite cities in the country, and only a few hours from where I now live. It’s called the “Hostess City of the South,” and you’ll quickly see why it gets that nickname. The people are some of the friendliest I’ve ever encountered, and Savannah has a nice, relaxed vibe that feels much different than most big cities.

If you like history like I do, you’ll love Savannah’s Historic Landmark District. It’s highlighted by 22 park-like squares, 19th century houses, and historic landmarks dating to the Revolutionary War on nearly every corner. 

We’ll be at the upscale Planters Inn where I’ve secured a special room block rate (see below under Travel Logistics). The hotel is on Reynolds Square, where we’ll be only a few blocks from bustling River Street along the Savannah River and within walking distance of Forsyth Park, Bonaventure Cemetery, and everything in the historic district.

Photo credit: Planters Inn

What I got was some ideas, some support, and some camaraderie, and yes, some friendship…and on the third day, a metaphorical shot to the head. In two sentences, Steve both took me to task for what I was doing, copywriting-wise, and blindingly clarified what I was supposed to be doing.

It was suddenly clear to me what kind of writing I was supposed to be doing, what kind of clients I needed to go after. But more importantly, I knew INSTANTLY what and who I was NOT supposed to be pursuing. THAT’S what Steve's retreat can do for you.

Ed Estlow

There’s a spot with your name on it. I’d love to have you.

Come to Deep Dive Savannah in November and get clear on creating a more peaceful, profitable, and enjoyable business, from this point evermore. I look forward to seeing you there.

Yes, Steve, I'm in!

Join us at Deep Dive Savannah