Frequently Asked Questions

So, what exactly do you do?

Three things:

  1. I write books for myself and others.
  2. I help freelancers transform into successful business owners.
  3. I offer fresh ideas, advice, and counsel to a select handful of businesses who want to increase sales and impact the world.

See more at Cafe Back Room.

What's your expertise?

First of all, my expertise is very limited. I’m an excellent writer and copywriter, I understand people and why they do the things they do, and I’m really good at one-on-one communication and selling.

That combination has served me well, and it serves my clients well. When you get right down to it, that’s the essence of business, isn’t it?

The rest? We can outsource everything else, or Google it and quickly figure it out. You have to with the pace of change today anyway.

Bottom line: I can help you get more customers and clients, serve them better, and keep them on board longer.

Why should I listen to you?

Actually, you shouldn’t. Not immediately, anyway. I’m always going to say good things about myself. Ha. Instead, check out my testimonials, Amazon reviews (and here), and LinkedIn recommendations. See what others are saying, and see what results they’ve gotten from working with me.

We should all have a healthy level of skepticism until we get to know someone. I do.

Let’s have a conversation before deciding if we’re a good fit for each other. Email me at or text me at 608-628-2865 and we’ll set up a time.

Where do we start?

If you’re a copywriter or freelancer of any kind, start with my book, The Freelancer Manifesto: 11 Big Ideas to stand out and thrive. Take the Freelance Quiz™ to be sure you’re going down the right path. It’s possible you’re not, and your quiz results (and my book) could save you thousands of dollars and years of your life.

If you’re a business owner who’s trying to navigate this Wild West free-for-all marketplace we’re in, take a breath. Slow down. You might be surprised to find out it’s a lot simpler than what you’ve been told. I can help you “connect the dots,” make sense of your current situation, and show you where you could be with a few tweaks.

I may or may not be the person to help you. Let’s talk and find out. At the very least, you’ll come away with some ideas you wouldn’t have thought of otherwise.

What do you mean by "Live Large"?

To me, Live Large isn’t about ostentatious displays of wealth. It means not holding back in any way with your personal and professional ambitions. It means putting more of you into everything you do. It means going all out so you can serve the world in a bigger way. Nothing big ever happened by playing small.

Got any free stuff?

Tons! Besides a few hundred articles I’ve written that are floating around online somewhere, I’ve written a few hundred blog posts here. Lots of great business advice.

Since 2013, I’ve also sent out over 2,715 email messages with ideas, insights, and personal stories, plus tips on selling, marketing, and positioning. A lot of my subscribers and Back Room members tell me they keep a “Steve Roller” folder to refer back to the really good ones. I’m honored.

You can get my book for free (just pay $7.95 for shipping and handling) here.

I’m happy to give free information, and I also spend a lot of time talking with prospective clients. But information alone won’t help you build your business. It’s the implementation and ongoing operation that makes the difference.

That’s what I can do for you — help you take action from these ideas and profit from them, not just learn them.

Who isn't this for?

My methods aren’t for everyone. If you need instant overnight results, look elsewhere. If you want a look-alike, sound-alike copy of someone else’s successful business, you don’t need me. If you only need tech and automation help and not creative ideas, I’m not your guy.

On the other hand, if you’re thinking long-term, creative, and custom-made, let’s connect.

Want a profitable and sustainable business model that fits you? A framework that suits your style? A system that works with your audience in today’s marketplace? I might have some solutions for you.

The Beatles or the Stones?

One for the ages, and off the subject for a minute here. The Beatles, of course. They’re the greatest band of all-time, and the songwriting duo of Lennon & McCartney is the most brilliant in history. Their songs and lyrics are running through my head at many hours of the day, no device or Spotify account needed.

I’ll qualify and say this: The Beatles are the greatest pop band of all-time. The Rolling Stones are the greatest rock band.

I’ve seen the Stones in concert twice (1989 and 1994), and Paul McCartney once (2019). I was born three months after the Beatles last concert at Candlestick Park, and I was two years old when they played their last gig on the rooftop of the Apple Records headquarters on Savile Row.

Best album? Revolver, then Rubber Soul, then Let It Be.

How much does it cost to work with you?

Most of what I do is tailored exactly to your needs. I’d be glad to give you a ballpark figure on our first conversation, and specific numbers with two or three options on our second conversation. I use a two-call, original proposal-based process.

These days I typically work on one-time projects ranging anywhere from $5,000 to $35,000, and ongoing projects from $2,500 to $10,000 a month. Book ghostwriting projects typically start at $25,000 and can go as high as six figures.

If your budget is below that but you’re interested in possibly working together down the road, we can chat and I can direct you to the right place for now. I’ll also offer some guidance and give you some ideas you might not have thought of yet. I’m playing the long game, and many of my current clients started out with a conversation months or years prior. I’m glad to talk with anyone who has big plans.

Business owners who aren’t looking for further engagement with me are also welcome to schedule a one-time call for $300. This is the best choice if you need answers, direction, and ideas without needing anything more.

That option is also there for freelancers and solo business operators, but I also have something better for you…the Cafe Back Room.

The Back Room is my private community where we focus on business beyond copywriting. It’s a place to get higher-level, deeper, more detailed answers to your business-building questions, in a group setting and one-on-one from me, for the ridiculously low price of $75/month (and you get $1,550 in free bonuses when you join).

That price will be going up regularly (every 6-12 months), but you’ll lock in your price when you join, for as long as you want to stay.

Finally, my Cafe Roundtable is a private mastermind group of 5-10 people I work with each year. Membership is by invitation and application only. If you have a book project in mind or are building what I call a Legendary Legacy Business™, let me know and I’ll send you details before we put together the next cohort.

What is your process?

As I mentioned above, to start with, I use a two-call consultative process. During our first conversation I’ll find out about you and your situation, tell you a little more about me, find out if we might be a good fit, and give you a ballpark figure if we are.

From there, I’ll craft a tailored proposal based on your needs and my assessment of how I can help you. I’ll give you two or three options with prices and terms, and we’ll walk through all of it on our second conversation. I’ll answer any questions you have, direct you to which option might be best for you, and ultimately let you decide which one, if any, best suits your situation.

Once we decide to work together, we’ll nail down project deadlines and evaluation points along the way to measure progress and ensure we stay on track. I’ll let you know what information I’ll need from you, and we’ll discuss how often we should connect. For some projects, there’s very little needed in between starting and finishing. For others, weekly calls may be required.

Whatever the project details consist of, my aim is to help you grow your business in the near future and long-term.

When are you available?

I typically schedule clients 3-6 months in advance. Occasionally I take on clients and projects with more pressing needs if both our calendars allow it.

Can I see your client list?

I have lots of testimonials (over 75 on this site), but I don’t reveal all my clients. Some of them ask me to keep things confidential, others I choose to (businesses in certain niches and ghostwriting clients in particular).

If you and I work together, be assured that all your information will be held in the strictest confidence. Glowing testimonials and results you don’t mind me sharing publicly are always welcome, of course.

What is the secret of life?

Just kidding, this isn’t a Frequently Asked Question. No one’s ever asked me this.

But I love this scene from City Slickers, where Jack Palance’s character, Curley, tells Billy Crystal’s character, Mitch, that the secret of life is “just one thing.”

Curley: “Do you know what the secret of life is?”

Mitch: “No, what?”

Curley: “This.”

Mitch: “Your finger?”

Curley: “One thing. Just one thing. You stick to that and everything else don’t mean sh*t.”

Mitch: “That’s great, but, what’s the one thing?”

Curley: “That’s what you’ve got to figure out.”

In all seriousness, this is sometimes what I help people do. Figure out their one thing.

What is the quintessence of life?

I’ll stop after this one, I promise. Also not a Frequently Asked Question, but maybe it should be.

It’s from one of my favorite movies, The Secret Life of Walter Mitty. The main theme, “What is the quintessence of life?”, runs throughout the film.

Ben Stiller’s Walter Mitty character works for Life magazine, whose motto is “To see the world, things dangerous to come to, to see behind walls, draw closer, to find each other, and to feel. That is the purpose of life.”

That resonates with me on a deep level, and the film’s scenes of Greenland, Iceland, and the Himalayas (all shot in Iceland) remind me of the time I hopped on a plane to Greenland on a whim. I’ll tell you the story sometime. Life is to be lived! Lived large.

Do you have a DIY option?

Yes. My Business Beyond Freelancing course is designed to help freelancers build a consistent, peaceful, and profitable business once and for all.

It’s a proven methodology that completely sidesteps the masses of freelancers all jostling for position. It’ll help you get good clients you love, on your terms. You can go through the program at your own pace and on your own schedule.

Also, my books are the easiest and least expensive Do-It-Yourself (DIY) entry point into my world. I highly recommend (of course I do) The Freelancer Manifesto. It could be the best $20 you spend this year.

In between that and my $1,500 course, check out the Cafe Back Room private community. The doors are always open, and you’ll get a bunch of bonuses when you join. Quite possibly the best $75/month offer anywhere online. I know, I know. I’m biased. See what others have to say before you jump in.

How is your community different?

There are tons of free copywriting groups and paid membership sites. They all seem to focus mainly on the craft of copywriting. We’re all about business beyond copywriting.

The Cafe Back Room will show you how to transition from a copywriter-for-hire or freelancer-for-hire to building your own rock-solid business, where you bring people into your world, not the other way around.

I started my private Cafe Back Room community in 2015 when my Copywriter Cafe Facebook group got too big and unwieldy. I wanted to have a smaller, more intimate space where we could keep ideas and advice away from our clients’ eyes (which was happening in the very public FB group).

I wanted to be able to interact 1-on-1 with members, and go deeper on business concepts like positioning, selling, and advising.

My passion is to develop stronger relationships. I help members create consistent, peaceful, profitable businesses they can ride for the next 5-10 years or more. That’s what we do in the Back Room.

Do you have a physical location?

I do. My business address is 6350 Lake Oconee Pkwy Ste 110-65, Greensboro, GA 30642. My home is in nearby rural Georgia.

While I don’t see clients in my office, I do get out and about quite often. I meet up with my Back Room members in person whenever I can, usually over coffee or lunch. I also host live events in Savannah twice a year.

Any live events?

Yes! In 2021 I hosted the 3-day Cafe Roundtable retreat at the Strong House Inn in Vergennes, Vermont. I did two events called Business Beyond Freelancing Live! (BBF Live!) in 2022 and 2023, in Providence in Boston. Starting in November 2023 I’ll be hosting Deep Dive Savannah twice a year.

I started hosting live events back in 2013. As an alternative to the big, loud, 300-person guru speaker events/pitch-fests that were popular at the time, I offered more intimate, hands-on, business-building retreats in interesting locations like the Green Mountains of Vermont, Santa Fe, Chicago, and the north woods of Minocqua, Wisconsin.

They proved to be popular, and many attendees came back for a second, third, or fourth time. I’ve hosted 16 multi-day events so far, and have lots more planned. Virtual Zoom conferences just don’t cut it. There’s nothing like gathering in person.

If you weren’t doing this, what would you be doing?

I’d be a tour guide in Ecuador. In my spare time I’d continue writing my novel series, which I hope to see on Netflix or the Big Screen someday. I actually was a part-time tour guide for a couple years, taking groups of 15 people to Ecuador in 2018 and 2019. I had a fully booked tour lined up for 2020, but we all know what happened.

Now? I’m exactly where I should be.

Why do you do what you do?

I love people and trying to figure out why they do the things they do. I love developing long-term relationships with interesting, intelligent people who are excited about business and life . And I love selling. The combination of those things is very rewarding.

In my mind, selling is serving. We get people involved in products and services they wouldn’t have otherwise if it weren’t for our efforts and skills. We enhance their lives, personally and professionally. At least, I hope that’s what I do for the people I work with.

If you and I haven’t connected yet, let’s do so soon.

In 17 words or less, what do you do?

I help people navigate uncharted waters and find a clear path forward, in business and in life.