I Made $5M Self-Publishing Books Online—Here Are 7 Things I’d Do Differently if I Were Starting From Scratch in 2022

Here’s a cliché pile of vomit to start your day ?:

“What would you do if you knew you could not fail?”

Despite the fact that my eyeballs just got whiplash, I gotta tell you: I used to think this was why most people had a hard time with FoLLoWinG ThEir DrEaMs (you know that’s the sarcastic way to write it, right?).

I used to think most people were afraid of failure, but you know what I’ve learned in 13 years of online entrepreneurship, helping thousands of people build their own mini empires here on the blog?

It ain’t fear.

It’s indecision.

Most people simply don’t know what to do. They know they don’t want the current situation, but they also don’t know which alternatives are available, or how to get started. This is even more prevalent among people who aren’t a part of the online culture: someone who runs a blog, a newsletter, a podcast, an Instagram, a Tik Tok, or some other channel where they’re consistently creating content and posting their thoughts. Most people are consumers, not creators. Most people use the internet as entertainment rather than a tool. And therefore, it’s even harder for them to figure out their career options, because honestly?

You can’t see what hasn’t been shown to you.

And most people on this planet have only ever seen the standard options.

Job hunt.
Change companies.
Work your way up a ladder.
Get a misery wedgie.
Rinse and repeat.

There’s nothing wrong with that, but if you’re called to create? And you really want to make something but you feel like you’re spinning your wheels because you don’t know how?

Then it’s time to put some studs on those tires and DIG IN. ? (Wow, there’s actually a tire emoji. NO BRA EMOJI, but hey, you're covered if you’re texting with your mechanic. ?‍♀️)

Logistics can really mess with peoples’ heads: how do I get started? Where do I begin? How do I gain traction? Which tools do I need? Where do I focus my energy? What comes first, second, third? What mistakes should I avoid? Why are there so many options? Do I need social? Do I need a newsletter? What do I write on the newsletter? How do I get people to notice? What if nobody buys? What if nobody even knows I exist?


So, after selling $5M in books online, I thought I’d offer up the 7 things I would do if I were starting over today.

You ready for this hayride?

Let’s go!

  1. Start with a newsletter, not a website.
    Yeah, you’ll need a website. Yeah, you’ll need it to look profesh. Yeah, you’ll need a legit logo. Yeah, you’ll need a fresh AF color palette and typography and accent fonts and probably an aspirin. Yeah, you will need professional photos. Yes, you will need ALL SORTS of pages. Yes, you will need a blog. Yes, you will need a bio that sells. Yes, you will need to suckle the juice from the armpits of internet fairies. And you’re going to spend, like, 3 years trying to get all of that set up….meanwhile, you won’t be getting any traction and your anxiety’s going to get worse and then you’ll feel like something is wrong with you because time is passing and the world isn’t throwing you a parade yet when, in reality, you’ve hardly even set up your opt-in. Time invested does not correlate to traction gained: action does. And, it’s really easy to get lost in the complexities of stuff that doesn’t matter, especially when you’re diddling around with a website yourself, which is an almost certain death sentence. (Picture the joy of not being able to get the size right for the social share images, and trying to edit it 500 different times, and every time it keeps coming out blurry or cut off.) What you actually need is the OUTCOME of the website: and that’s an audience. So, using my rule of keep it fucking simple, I’d sign up for ConvertKit—I use them for all of my projects and that's my affiliate link where you can get started for free—set up a dead simple opt-in page like I did here, here, here or here (that’s their Hudson template), hook it up to a branded URL, and then I’d use that as my starting website where I can direct people for now. DONE.
  2. Sit down and write out 12 pieces of your best advice—the stuff you wish you knew starting out.
    What’s the BEST advice you have on your topic? Make a list of twelve things you live or die by—the most useful things you could ever tell your customers. If you’re making candles, I want to know the best ways to store candles, light candles, keep candles, make candles, burn candles, gift candles, buy candles, use candles for rituals, what kinds of candles you should never buy, which kinds of hidden ingredients go into candles—the works. If you’re into DIY home remodeling, I want to know the best way to measure your space, tear up tile, use a saw, knock down partition walls, pick colors, negotiate with contractors, buy materials, install lighting. What are the twelve pieces of advice you wish you knew starting out? What are the twelve pieces of advice your target audience needs to hear? What are the questions you routinely get? Do not hold back, do not offer bullshit advice. Give ‘em your best, most helpful, most AH-HA! moment kind of stuff. Every sale in the world starts with an AH-HA moment.
  3. Turn those 12 pieces of advice into 12 love letters of 2,000 – 3,000 words each.
    Here’s where things get fun: now, take those twelve pieces of advice, and flesh them out into twelve individual love letters to your former self—the stuff you wish you knew when you first got started. Each love letter should be around 2,000 – 3,000 words-ish (this one is ~ 2,500), and that’s for two reasons. (a) So you don’t get overwhelmed by the looming thought of writing a magnum opus any longer than that, and (b) So your eventual readers will actually get in the habit of reading your emails. Research shows that when you open an email and you get through it, you actually get a dopamine boost from having “checked off” something that you had “to do.” On the other hand, if you open a loooooooooong email and see a giant wall of text, you’ll likely think to yourself, “Eh, I’ll get to this later,” and then never get to it because #life—and then, the next time you get one from that sender, you won’t open it because you know it’s long, and then you’ll start to subconsciously associate those emails with failure since you aren’t able to “complete” them. You do not want that association. Keep ‘em smart as hell but easily digestible, without making it feel cheap & chintzy. (That’s where the “smart as hell” comes in: you need to give people something great to make it worth their time, without wasting their time.)
  4. Put those love letters on autopilot to send out 3x/week.
    Next, load those love letters into an automated email sequence in ConvertKit to go out 3X/week, so every single new subscriber is going to get YOUR BEST ADVICE, right up front, like clockwork, M / W / F. That’s important. Consistency is more important than unique genius, okay? Do not overthink it. Just write it, put it on a schedule and pull the trigger. That schedule should be 3x / week for a couple of reasons: (a) You need to show up as a leader—that’s what modern marketing is—so you need to be in people’s faces regularly (otherwise you’ll be a forgotten like a tiny little frog burp); (b) 3X a week is what’s necessary to build a habit of opening your emails and reading them and looking forward to them and remembering who you are; (c) If you send 3X per week, and you’ve got 12 emails in total, that’ll get you through your first month. Woo hoo! And that means that, for one solid month, you are showing up consistently and BRINGING THE HEAT. ? And, you only had to do the work once; thereafter, technology will go to work for you, forevermore, and replicate your efforts. It doesn’t matter if you then amass 300 subscribers or 300,000—they’re the work is done, and they’re getting the best of you. What a bargain! It’s the best way to package your knowledge into a smart container that will benefit everyone equally, rather than spending loads of time writing one thing, sending it out, and then starting from zero again in the morning. (Talk about spinning wheels.)
  5. Make an offer in exchange for money—and put that on autopilot, too.
    You’ve been building up trust, likability, and interest for the past 30 days…at that mark, they should get a promo sequence of emails that pitch your reader on a paid service / consult / digital product / ebook / course / membership / whatever you want to sell them. You should work on making this feel like an event: don’t just send out one meek little email with your tail between your legs that quietly whispers at the bottom, “Psst, sign up here…….” No, darling! You want to blow open those doors and make a grand entrance! You want to make ‘em say YESSSSSSSSS, I’M PAYING ATTENTION, I NEED THAT! You want to turn your sale into an event. As such, I would recommend no fewer than 6 sales emails: 1 on day one, 1 on day two, 1 on day three, and 3 on closing day: morning, afternoon, and night. I'd actually recommend more, but that's a good starting point. Many sales promos are longer than this, up to 3-4 weeks long, with hella more emails, but that depends on your price point. If you’re selling an ebook, that’s overkill, but if you’re selling a $2K course, that’s necessary hullabaloo, as it actually adds legitimacy to the project.
  6. Now that you’ve got your MONEY set, you can pursue FANFARE.
    Now you can start worrying about social media, pitching articles to editors, and even writing your own blog. Because now, you have somewhere strategic to tell people to go, once they engage. (Your newsletter. With strategic communications. Designed to build a relationship, offer value, and then sell something in exchange for real and actual money.) Now you’re not just spitting into the wind: you’ve got a solid system in place to capture leads, take ‘em by the hand, make ‘em fall in love with your ass (maybe literally), and then convert them into customers. Most people make the mistake of building an audience for 900 years and then procrastinating the sales part either because they don't know what to sell, or they don't know how, or it's scary or they feel slimy and weird. But, I prefer to sell fast and early, so you can iterate fast and early. You can start bringing in cash flow. You also get a giant boost of credibility from having your own product on the market, too—which is one of the reasons why I recommend creating a simple digital product in the form of a book to begin. It’s low-production, high value, and makes you look like a star. (So long as you aren’t using those CD-ROM mock-ups from the early 2000s, LOL.) Plenty of TikTokers and Instagrammers run into this problem: lots of eyeballs, no actual revenue. No business strategy. No idea how to monetize. There needs to be a thoughtful bridge—and you need to build it. But I’d recommend starting with the money, first, because if you know how you want to make money? You can shape your strategy to get there, and make sure your marketing builds up to the grand finale correctly. But, if you have no idea where you’re going, it’s really hard to pick the right road. (And you might end up in Arkansas.)
  7. And, finally? Learn how to write a damn good headline.
    A lot of great people and good advice get buried underneath vague & non-compelling headlines & article titles that, to a stranger, are NOT something they’re going to click on. So allllllll of your hard work is done in vain, and no one ever sees it. And, isn’t that a real kick in the crotch? HEADLINES ARE REALLY IMPORTANT. And you know what the best headlines start with? Need. What are people dying to know? What kinds of things are they already searching for? What kinds of conversations are happening in your industry right now? What’s timely? What’s important? What’s changing? What opinions do you have? What are they curious about right now? How can you show up and enter the chat? How can you put your content right in front of their cute little face? The answer: start with research. Start by researching what people are actually searching for online when it comes to your topic: then build your content strategy from there. (This is why it's a myth that you need to have an audience first. You just need to be well-researched.) This is the kind of content you want posted publicly, on your blog and in articles you’re writing around the internet, because this is what’s going to lead people to you. Don’t put this behind your newsletter: make it public, make it loud, spread it everywhere. You can see how this works: (a) Person starts researching your topic; (b) Person comes across article you’ve published or workshop you've given or podcast you've been on, either on your own site or that of a third party; (c) Person digs your perspective; (d) Person clicks on your call to action to subscribe to newsletter; (e) Person gets your smart AF emails 3X/week; (f) Person builds a relationship with you and respects you; (g) Person gets pitched your thing; (h) Person says HELL YES. The beauty is that 75% of that happens on autopilot, automatically, every single time, like perfection, because you designed it that way. The other 25%, however, is you figuring out what people are looking for, and then talking up a storm about it wherever you can publicly. One of the best tools I’ve found for doing this research easily and powerfully? BuzzSumo. Specifically, their “Questions” feature, which shows you the most popular questions being asked on any topic around the web (not just on Google, but in forums, too). It’s expensive, but they offer a trial and if you’ve got your sh*t together, you can do a ton of research in a couple of days, and then make a real nice spreadsheet for yourself containing all of the questions that are being asked, right now, about your topic. Obviously a subscription would let you keep the pulse and continually do this, but for now, just focus on getting the foundations in place. (You can also use free tools, but Buzz Sumo really is the shit—and that’s not an affiliate link.) Then, you can take those questions and turn them into killer headlines that clearly address what someone’s going to get out of reading your post. What’s in it for them? Ohhhhhh, only the answer to the very question they have. ? And voila, headline writing just got SO MUCH EASIER.

Okay, darling?

Do not overthink this. Do not overanalyze it all to death and whether or not you are doing it right. NO ONE’S DOING IT RIGHT. We’re all figuring it out as we go. Just start taking action without constantly policing your action. Let yourself learn as you go. Let yourself experiment, create, and make something beautiful! And helpful! And neat! And fun!

These are a few of the things that I’ve figured out, because I have trial and errored more online business strategies, tools, and methods than god. Eventually, you pick a few things up.

And, you will, too. But, this is not a test. This is all just art, and when you learn how to use technology to deliver your art in modern new ways?

It becomes money.

It becomes a new way of earning a living.

And it becomes an all-new world of options that didn’t exist for you before—until you made them.



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