Pioneer Nation is a gathering of internet creatives with a blog and a passion, committed to doing what they decided was their work in the world.

There’s this weird synergy at the convergence of authenticity, audience, and the Internet, where people can find a good problem to be solved and offer a solution to anyone who has this problem, anyone in the entire world.

Many of the workshops were taught by people who had found this convergence, people who crafted an offer and an audience that matched well enough to enable them to earn a good living by serving their chosen people. These teachers offered their own experiences as case studies in how the rest of us can find a spot at this convergence, too.

Throughout all the workshops and keynotes, the overarching message was that if you can resonate with an audience, and provide enough value to enough people, there’s a good chance of making a living doing what you love.

Many of the non-Instagram photos below were taken by Armosa Studios. Those with quotes on them were designed by me. Please share, but keep attribution if it’s there already.

First, a quick FAQ:

What’s the difference between WDS and PN?

The World Domination Summit is also hosted by Chris Guillebeau, and just completed its fifth year this summer. There were 3000 attendees last year, compared to Pioneer Nation’s 150.

I’ve been to both Pioneer Nations (you can read about Pioneer Nation 2014 – or how I broke my newsletter on the Hot Seat) and I’ve been to the last three years of WDS (I wrote about WDS 2015, WDS 2014, and day 1, day 2, and day 3 of WDS 2013.)

I hang out with a few other regulars of these conferences (like Steven Shewach and Tom Rooney) who compare notes with me year after year, and it seems that the big difference between WDS and PN is that Pioneer Nation is full of people who are already doing it.

WDS is great for inspiration, to break you out of your cubicle, and get you thinking about your unique service to the world. Once you’re out, and you’ve found it, and you’re looking to make this dream-job-entrepreneurial-website-thing actually work, Pioneer Nation is where you dive deep into studying the mechanics of how to do that.

Pioneer Nation begins. #pdxpioneer #mountain #entrepreneur #retreat

A photo posted by Caelan Huntress (@caelanmac) on

Everybody attending was genuine and helpful and interesting. The camaraderie among the attendees was very high, as is usual for these events, and everyone I talked to passed the role of coach and mentor back and forth with me, trading insights and ideas and tools at the high level of understanding that all digitally fluent entrepreneurs share.

Pioneer Nation 2015 Event Schedule

There were keynotes in the morning and evening, with breakout workshops in three sessions in between. The schedule offered exciting but somewhat vague descriptions of each workshop, and you had to select which one workshop you were going to attend, and the five you weren’t.

To complicate the selection process, the names of the presenters of each workshop were left off of our schedule, leaving us to make our decisions on the merit of the titles alone. Some of the titles and descriptions were accurate enough that I could tell which was the right fit for me; but in other cases, there were presenters that I really wanted to see, because I knew that they were the people from whom I was good at learning, and not having their names available to make my decision really frustrated me a couple of times.

I suppose the point of this was to keep the popular speakers’ workshops from being flooded with participants, and the other workshops from being empty, but a better solution to that could have been to not have so many multiple workshops going on at the same time.

Way Far Away

I didn’t know until after I bought my ticket that the event was not going to be held in Portland. The price of the ticket was already a huge stretch for me, and paying for lodging (and being away from my family) for three nights almost made me decide not to go. But in the end, I’m glad it was secluded, because it meant everyone in our digital tribe was sequestered on the mountain together for a few days, and enhanced the sense of community we felt for the brief period that the event lasted.

The small size of the event was great for culturing relationships. I’ve found that no matter what the size of the event, there are only about a dozen new relationships I can cultivate in a weekend, and maybe two dozen I can keep going. Since the proportion of presenters to attendees was abnormally high for this event, it meant I was able to get a stronger connection with some really fantastic people, many of whom were very successful and remarkably insightful about the process that landed them there. At WDS I’d be lucky to meet two or three speakers, while at Pioneer Nation I had great conversations with more than half of them.

In addition to livetweeting the event at #pdxpioneer, I also took lots of notes, during keynotes and workshops alike. Below are my biggest takeaways.

Pioneer Nation 2015 Speaker notes


Duct Tape Marketing | @ducttape

What I love the most about hearing John speak is the solid, long-term perspective you only get from doing something for a really long time. Since blogging is still relatively young (or at best adolescent), there are precious few sages in the space, and this man is one of them.


John has been running Duct Tape Marketing for 28 years, and during that time he has published 3297 blog posts and 601 podcasts. He’s been in marketing since before the Internet began, and has been navigating the experience of marketing to a global audience during the entire time that the Web has spread across our culture’s third eye.

He has a folksy, amiable earthiness to his character, which makes listening to him a joy in itself. The content of his keynote, as wise and insightful as it was, only amplified my enjoyment of his talk.

"Develop a methodology for how someone gets value out of what you do." – @ducttapemarketing #pdxpioneer #marketing

A photo posted by Caelan Huntress (@caelanmac) on

The picture he painted was of a customer in all the different stages that they get to know you. In these 7 stages, what he calls the ‘hourglass,’ a customer goes through a series of stages, during which you can (and should) communicate to them differently:

  • Know
  • Like
  • Trust
  • Try
  • Buy
  • Repeat
  • Refer

As your customer goes through this process, of getting to know you deeper and how your services can help them, you should constantly produce value for them along every stage of this progression.

It got me thinking about how our typical marketing messages only target customers at a particular stage or two, neglecting the evolving customers in many other stages.

If we can provide memorable value to them at one stage, when they evolve to a further stage they are much more willing to do business with you. If you focus on producing content that helps guide customers through that journey, John says, then people will expect to pay a premium for what you do. “Every element of your methodology should be worth paying for,” he said.

He was dynamite in the breakout session, the ‘Campfire Chat’ when Chris would moderate the morning’s or the afternoon’s speakers and take questions from the audience. When someone mentioned something about pricing, he punctuated his point with, “Does anybody like to compete on price? There’s always someone willing to go out of business faster than you.”


As someone who has produced a massive amount of content, John is now changing his own tactics. “How about we do less, but we do awesome,” he said with a smile. Sharing his own progression in his entrepreneurial journey, he realized that churning out such a volume of content wasn’t as effective as just producing awesome content, even if it takes longer to produce.


Portland Gear | @portland

Before seeing him onstage, I didn’t know who Marcus Harvey was, but I had been exposed to his works. Because like most of his demographic, I’m a Portlander that loves Portland.


Marcus turned the Instagram handle @portland into a big audience, by sharing and celebrating the many things there are to love about Portland. Then he turned this audience into a business. The name of his business follows the formula he described in his excellent branding workshop.

(Who you serve) + (What you do) = BrandName.

Marcus follows this formula with Portland Gear. He makes T-shirts and hats that have a Portland-themed logo or message on it. He sells gear to Portlanders about Portland.

The name Portland Gear isn’t cute, or clever, and it doesn’t take you a few moments to figure out what the heck it’s all about. His brand name is tightly defined, and he challenged us to define ours as tightly. (The project I came to Pioneer Nation to work on is called Father Fitness. I was glad to see that I’ve got it.)

What helped Marcus to gain such rapid growth in his business is a powerful tactic that is seldom done by on line entrepreneurs, but it can be huge when it’s done well:


Marcus had this vintage VW bus outfitted with his logo, and would send out a photo on Instagram: ‘Hey, we’re out at First Thursday selling shirts, the first 100 people here get a free t-shirt,’ and a whole bunch of people would show up.

People who already followed him and already shared his content on social media were happy to have the opportunity to get together and have a shared experience, to celebrate their love of Portland, and the Portland Gear brand sets the space for that.


These are the 4 questions he challenged us to ask about our own brands:

  • What makes me different?
  • Why are we cool?
  • Where do I find people who care?
  • How do I get in front of them?

He told us a story about a local beer that is high quality, and takes more money to produce, but customers wouldn’t pay fifty cents more at the tap. The solution, he said, is to “make the brand work 20% harder.”

As an entrepreneur with experience in apparel and physical goods, Marcus had some really great insights about products and upsells.

Tell the consumers what to buy, he says. Don’t give them options.

If someone is going to go in and experience your brand, give them the best experience, by curating your product.

Part of that curation is how you present yourself to them in a digital space. There are 3 tiers of content, he says: content that makes your brand worth more, makes your brand the same, or content that damages the brand. Looking back at your content stream, seeing what gets engagement and what falls flat, can help guide you to make content that increases the value of your brand.

Your customers will be very honest with you if you create an honest space for them to do so, he says. Creating tons of automated content, it doesn’t create an honest space.

Marcus has focused on creating shareable and relatable content, and he has done it so well, that now his customers make relatable and shareable content for him. They take pictures of themselves wearing his clothes, and help promote his brand, because they believe in it.

corbett-barr-header | @CorbettBarr

Corbett is one of those digital savants who figured out early on what works and what doesn’t online, and he’s been generously sharing his insights and his strategies for years.

I’ve known Corbett as a member of Fizzle, the online community of entrepreneurs he co-founded. Inside of Fizzle he has a ton of video courses on everything an entrepreneur needs to create, build, and scale a business, so his insights for this group were particularly relevant and valuable.

(Pioneer Nation was like an in-person concentrated dose of Fizzle. If you want to get that sort of knowledge and community all year round, do yourself a favor and get the Fizzle free trial.)

Corbett gave his keynote speech on his birthday, which has got to be a fantastic birthday present. (Lots of applause, your favorite stories, and a cupcake on stage, heck yeah!)

Since he has so much in-depth tactical information inside of Fizzle, he spent his keynote talking about the broader considerations that an entrepreneur has to develop in regards to their work and their audience. As the entrepreneur, he says, you have to set your priorities, and guard your vision.

I love that idea – that you must guard your vision, or the market, the audience, or the tools you are using can steer your business in a completely different direction. Only by guarding your vision are you able to stay on course.


Corbett shared some of his early failures as examples of how he was able to keep his vision on course by pivoting into different business models. He was one of the early bloggers to make blogging work, to realize that advertising was a waste of time, and to squarely focus on a problem to be solved, instead of what he wanted to say.

“Your business isn’t about you,” he said. “It’s about your customer.”

He brought up a picture of Yoda and Luke Skywalker, and challenged us with the same question his co-founder Chase Reeves challenged us with during last year’s Pioneer Nation: who is your business in this picture?


Your business is not the hero. It’s not Luke Skywalker. That’s your customer.

Your business is the sage the hero comes to when they need the tools to save the world.

This realization has been groundbreaking for me. Once I took off the mantle of the hero, and started to look instead for other heroes on their own quests to assist, my business started gaining traction.

If you’ve been an entrepreneur for any significant length of time, I’m sure you’ve hit this wall. You spend all your time, ideas, and resources to build something that you think is really fantastic, and then you launch to crickets.

After a few badly failed launches, I set about learning how to prevent it from happening again, and this perspective of helping the customer as the hero in their own story has been invaluable.

We’re all in new territory here, the Digital Pioneers, so it’s understandable that so many of us overlook this crucial (and subtle) perspective.


That makes it easier for me to go easy on myself, for not achieving success earlier than I have. I’ve been blogging seriously for six years, and while I had a good run as a web designer for a bit, I’ve never been able to get a solid blog underneath me to support me and my family.

Over the past year that I’ve been in Fizzle, it’s been really encouraging to believe that I can do it, once I get the mechanics right. It sure helps that there are friendly guides along the trail like Corbett to point the way.


Quiet Power Strategy | @taragentile

Tara Gentile always dazzles the audience with insightful questions that compel you to reframe everything you’ve been doing in your business. This might be because, as she says, Tina Fey is her spirit animal.

She used Tina to illustrate a really serious point: if someone ever tells you that you really, really must do something (as Tina described in Bossypants) you don’t really have to do it. Nobody says you “really, really must” deliver the baby. If it has to be done, it’s self-evident.

It disarmed all those FOMO fears we get because there’s so much to be done online – setting up social media profiles on new hot networks, writing new autoresponder campaigns, building new landing pages with this new plugin…all this stuff that everyone says you really, really must do, it’s really not that important. If it’s too much, just drop it and move on. Don’t overburden yourself with something that’s not going to keep the lights on.


In addition to her keynotes, I attended both of Tara’s workshops, because she is a fountain of relevant and useful information. She’s a business strategist who certifies others to be business strategists – her content is top-shelf. Out of the many pages of notes I took, here are the biggest lessons learned:


Finding our Quiet Place

We live in a really noisy world, and we have more sensory and intellectual inputs than our ancestors could have imagined. The way we combat this noisy world, Tara says, is to come back to our quiet place. The place of power where we don’t have to be loud.

She advocates for doing ‘Living Room‘ launches for a product, instead of a big, messy, tell-everyone-in-the-world scattershot method of promotion.

It’s not that the noise overwhelms us, she says, it’s the way it overtakes us. It keeps us from asking the questions that keep us aligned to our purpose, where we know what is true:

  • What do I want to create?
  • How do I want to connect?
  • What big thing do I want to have accomplished in 6-12 months?

If I’m overwhelmed by noise, then I can’t make my decisions from a place where these questions are guiding me, a place of quiet power.

"The way we combat our noisy world is to come back to our quiet place." – @taragentile #pdxpioneer

A photo posted by Caelan Huntress (@caelanmac) on

Marketing is connection, Tara says, and promotion is only a very small piece of that.

Cultivating a connection between a business and a customer is much easier if you treat your customers as progressions on a journey, instead of a static Ideal Client Profile. Customers are people, and they change. Like John Jantsch was saying, if you can use your content to guide them through their stages, they will value your words.


Tara got deep into the stages of the customer journey, and in keeping with the workshop-do-the-exercises attitude at PN, she had us define our customers in their various stages. I took the opportunity to flesh out the customer archetype for Father Fitness:

  • Curiosity – new dads are curious about having a baby, older dads want to know tips and tricks for doing it better
  • Frustration – dads are tired when they get home. Home is no longer a sanctuary.
  • Question – How can I endure when I’m tired? How do I stay interested in my kids when I’m tired?
  • Goal – Happy wife, quieter kids, easy bedtime.
  • Ultimate Goal – Dads want their kids to admire them as role models.

Using this framework, I had an idea for a completely new angle on Father Fitness, and a small product I could create that solves a relevant problem. Happy Homecoming – A workbook to help you enjoy your time at home with your kids.

Then we went into the customer’s actions. What are they: Saying, Doing, Thinking, and Feeling? By writing out these answers, I was able to get a clearer perspective on what is really driving the dad.

What really blew me away, though, was Tara’s 4 Levels of Awareness:

  • Completely Aware – your customer knows all about you, and they will buy anything you create.
  • Solution Aware – they know the solution to their problem, and just need to be convinced that your solution is the right one for them.
  • Problem Aware – they know what their problem is, but don’t know what solution they need.
  • Unaware – They aren’t aware that they have a problem, and need to be educated about the problem first, before anything else happens.

You can message these 4 different types of customers in 4 different ways. You really, really must do this. (See what I did there?)

In most of the marketing I’ve done in my life, we focus on one (maybe two) of these levels of awareness, and our messaging speaks to only those types of customers. Other types of customers are left to infer how it could specifically apply to them, and now that I see it this way, I realize it’s just bad marketing.

Tara challenged us to take the same message or idea, and rephrase it to communicate with people at each of these levels of awareness.


I sketched out a content map for Father Fitness that repurposes 5 messages across the 4 levels of awareness, and suddenly I have my first 20 blog posts mapped out. I focus on the 5 types of fitness a dad needs to be balanced (Physical, Financial, Emotional, Social, and Mental Fitness) and I can write about each topic 4 times, one for each level of awareness.

All 4 posts go into the same funnel, and they get there by using what Tara calls the hottest new trend in content marketing: content upgrades.

This is when you offer an expansion on your post, through a worksheet, spreadsheet, email series, or webinar that provides deeper insight on the subject of your post, and to access the content upgrade, you need to enter your email address.

I love the content upgrade tactic, because it provides a contextual value that is much more targeted than ‘Sign up for my email list!’ The first time I saw a content upgrade, I was floored at how smooth it was.

I was doing some research on customer interview questions, and I found this blog post by Customer Development Labs on why you should not talk about your product during these interviews. When I finished reading this rich and insightful article, by the time I got to the call-to-action for the content upgrade at the end, I was delighted to hand over my email address.

So now I have a lean, cohesive plan for content creation.

  • Create 5 workbooks on the 5 areas of fitness
  • Write 20 blog posts on the 5 areas of fitness across the 4 levels of awareness
  • Find 60 blogger dads to quote (3 for each article)

I went into Pioneer Nation with a vague idea for my content map, and plenty of directions available for me to take. By the time Tara’s workshop was done, my plan had crystallized into an elegant shape.

vanessa-van-edwards-header | @vvanedwards

Vanessa Van Edwards is an enthusiastic ambassador of happiness. Her presence onstage is electrifying, and her keynote focused on helping us to identify what will make us stand out to our audience and make them happy.

Vanessa investigates the mechanics of how this works through her website and her books, using psychological studies as examples that illustrate why people make the reactions and connections that they do.

1. What’s your WOW factor?

What is it about you that makes you impressive, amazing, and inspirational? That is the very thing that people are attracted to, what they will follow you for, and it can be the core around which you build your audience.

This WOW factor can be concentrated into a tiny, portable dose through a clever business card. I’ve long been a proponent of unique and outstanding business cards (mine is a wooden coin), and Vanessa gave us a thorough understanding of why this marketing tactic is successful: it triggers dopamine.

This makes me #happy. Literally. @vvanedwards #pdxpioneer

A photo posted by Caelan Huntress (@caelanmac) on

Dopamine is a chemical that our brain releases when we feel happy. How can you make someone happy when you first meet them? Your business card, your name tag, your opening line, these are all ways that you can introduce yourself to new people with a dose of joy, and remain memorable way beyond that first meeting.


2. Find your Why Story

When we tell someone a story, Vanessa told us, our brain and their brains align. This alignment causes all sorts of synergy, so instead of telling someone your Why, tell them your Why Story: the story that incites why you do what you do. This makes your Why much more relatable, and your listener will align with it on a deep mental level.

Every pitch is a progression of What, How, and Why, Vanessa says. “The Why is a hook. It invites people to be on your journey with you.”

That invitation is crucial, because people don’t like to join a journey because they are told they need to join it, or they feel obligated. By inviting them, and aligning with them, a customer will voluntarily join you on your journey, because they feel like they are a part of it.

3. Learn from your Numbers

Every week Vanessa does an “Awesome Audit,” where she looks at her Social Media Gold and her Traffic Sparks. She guided us how to go into Twitter Analytics and find our top tweet for the week – she said every week it surprised her, and I have to admit, I’ve been surprised as well. The Top Tweet is the one that gets the most engagement and exposure, and it is a clue into what is really gaining traction with your audience.

“The people who talk about you are your brand evangelists,” she said. These are the people who will spread your message of their own free will, because they have aligned with your message, and find your platform a convenient place to share ideas that they believe in.

Brand Evangelists remind me of the First Follower, who is a kind of brave leader that Derek Sivers posited could be even more important than the founder of the movement:

4. Finding your People

In addition to cultivating an audience, you also need to cultivate your core group of mastermind-level partners, the brain trust that can give you targeted, specific feedback on your goals and your progress. Vanessa calls hers an Awesome Club, and every month these 3-4 people share their answers to these five questions:

  1. What are you working on?
  2. What is your biggest success?
  3. What are your biggest obstacles?
  4. What is your one goal for this month?
  5. How can we help?


I like this mastermind format, because it is a vision-focused agenda. My own mastermind habit is to recite our Wins, Challenges, and Commitments (after reading Andrew Carnegie’s mastermind opening.) This touches all the important subjects: celebrating what’s going right, dissecting what’s going wrong, and deciding on what’s next. Vanessa’s formula expands on this by beginning with a recap question, and ending with an examination of available assistance, which is a really good idea.

5. Vulnerability is Sexy

Vanessa closed her keynote with the idea that is so frequently championed in WDS and PN circles, that the thing that makes you vulnerable is what makes you appealing.

The Iceberg Illusion, she says, creates the tendency for us to see the surface 10% of someone and assume that is the whole picture. There is actually 90% more depth underneath, and when we are exposed to it, we are exposed to the true breadth of the person we are dealing with.

I have to admit, I have developed conflicting feelings about this idea over the past few years. Vulnerability has been championed as the new authenticity, as the key to your strength and power, ever since Brene Brown’s landmark TED talk on vulnerability.

Personally, I have tried this out with underwhelming results. I’ve got lots of secrets to choose from, and stories I’m not ready to tell, so I tried exposing a handful of these vulnerabilities to my audience and my friends, and I can’t say that it has helped me in many ways. In some cases, I lost friendships and clients, because I was willing to be vulnerable and share what was beneath the surface. Some friendships grew closer, it’s true, but apart from distilling my tribe, I haven’t yet seen the benefits vulnerability is supposed to bring.


So while I acknowledge that vulnerability has been a hot trend in both marketing and personal development, I have my doubts about its effectiveness. Or sex appeal.


Armosa Studios | @armosastudios

How bad could it get? What happens when you really fail? That’s what Wes and Tera Wages came onstage to tell us.

They have been photographers for this community since it started. Their success is pretty impressive, and when they painted the picture of where they were in their career – shooting a big project with Marie Forleo, and flush with incredible shots for another client after three weeks of world travel.

During Marie’s event, there was a lot of talk about failure, and how you need to embrace it. Wes said he felt like he had never really felt failure, not the kind that affects his work or his clients…and then they got on a train, somebody helped them load their bags, and their camera bag was stolen in Italy.

"No matter what happens, you will survive." @terawages and @weswages at #pdxpioneer share a #business #horror story

A photo posted by Caelan Huntress (@caelanmac) on

The equipment itself, tens of thousands of dollars, was a mighty blow. But when they described the work they had been doing, and the photos they had on those cameras, and the effect these photos were having on their clients, we saw that what was really stolen was their work, snatched from the cradle, before it even had a chance to get beyond infancy.

Hearing them describe what this work could have been, it was clear that this was what really crushed.

Then they talked about how they picked themselves up, the calls they had to make to their clients, and what they decided to do to move forward.

Because that’s what really happens, after every failure: you move on.

You keep going.

Time doesn’t stop, so neither do you.

Now they are back at Pioneer Nation, taking great pictures, and doing it all while trading a baby in an ergo carrier. Things get better, no matter how badly you fail.

I love this message, because the failures in life are often what makes us strong. You only gain the fortitude needed to withstand the fires if you go through the forge of failure.

grant-baldwin-header | @grantbaldwin

Grant is a public speaker (who happens to play some real serious ping pong), and he has leveraged his speaking business exponentially by getting into webinars.

“Part of the challenge with public speaking is that it doesn’t scale well,” he said during his workshop. By it’s very nature, speaking is a high paying, manual labor job. By teaching weekly webinars, he’s found a fantastic way to scale.

Grant has hosted a podcast called “How Did You Get Into That?” for some time now, and in addition to being a fantastic excuse to get into conversations with people he wants to talk to, it has turned into a platform for him to drive traffic to his online course.

He does a lot of JV webinars with other people’s audiences, and after interviewing more than a hundred entrepreneurs, he’s got a rolodex of people with their own audiences to whom he can teach this webinar. During his first workshop, he generously showed us the mechanics behind his system, which has brought in hundreds of thousands of dollars in revenue since the start of this year.

At the end of last year, he had a launch that didn’t do so well. It was called the ‘Clarity Course,’ and it helped people get clear on what they really want to do. It doesn’t have the tangible benefit of Booked and Paid to Speak, so he dropped the Clarity Course and moved into this new product, because it taught a tangible skill that people were willing to pay money for.


What’s great about Webinars, Grant says, is that they scale. He can teach a webinar every week to a new audience – and it’s the same webinar, with the same content. The only thing that changes are the FABs – the Fast Action Bonuses he offers to people for signing up for his course in a specific timeframe.

Grant had plenty of advice on how to keep your audience happy, and people don’t like it when you change the price. If someone buys your course at one price, and they see it somewhere later for another price, they feel like they lost out. “Don’t change the price up and down, but change bonuses instead,” he advised.

By offering different bonuses (like a new workbook, or 5-7 minutes of audio from the interview that isn’t included in the podcast) you can constantly offer new, relevant incentives to your current audience, without giving your paying customers FOMO.

Every webinar, Grant gets on 15 minutes early and starts chatting with people. He asks a lot of questions, and encourages people to answer softballs right in the beginning – Where are you from? Whats the weather like there? Type it into the chat box. This gets them in the habit of participating, and sets a much different tone for the event.


Grant shared his webinar registration autoresponder sequence, and it goes like this:

  1. Welcome email – thanks for registering! Here’s the link and time.
  2. Did you get the link to the webinar? Here it is again.
  3. Survey
  4. Day before webinar reminder
  5. 7am morning of webinar reminder
  6. 1 hour before webinar reminder
  7. 15 minutes before – we’re live! Come say hi.
  8. 1 hour after – will send the replay link tomorrow, reminder of FAB
  9. 7am day 1 after – Replay link
  10. 7am day 2 after – Replay link and offer reminder
  11. 7pm day 2 after – Offer is closing at midnight tonight
  12. 7am day 4 after – payment plan offer
  13. 7pm day 4 after – cart closes at midnight tonight
  14. day 6 after – Started edition of program for $197
  15. day 9 after – survey

This is a really well-crafted autoresponder chain, and Grant has successfully used it to generate more than $250k in revenue. During his workshop he got into the details of why each message was where it was in the sequence, and other options that he could have used in each space, as well as the reasons he discarded them.

Simply put, this is a really polished sales funnel. I took lots of notes and subscribed to his newsletter, so I could study it in detail. If you’re into this stuff, I highly recommend you do the same.

Pre-selling your product

“The idea of having someone paying you for something you haven’t yet created is really weird to a lot of us,” Grant confides. But this is one of the most effective methods to create a course, because it funds the creation process, and enrolls your audience in the creation of it.

“Those early adopters are going to be your biggest fans,” he said.  By sending out regular surveys to his beta tester group, Grant has been able to ensure that he is making the product that they want. The early users also feel a sense of ownership over the product, so they are more likely to assist in promoting (and even championing) the course when it is done.

“I want to make money from this,” Grant admits, “I like to eat food and live indoors, but I really want to see people go through change.”

When people transform, that’s how you know your product has worked.

nathan-barry-header | @nathanbarry

Nathan is the inventor of ConvertKit, a fantastic email marketing platform used by many of the workshop teachers that I’ve written about in this post. That fantastic webinar registration pipeline that Grant Baldwin laid out for us above was only really possible because he used ConvertKit.

Nathan is a friendly guy who is really good at sharing what he’s learned. His excellent book Authority provides the basis for gaining credibility in a topic by doing the same thing.


At the moment our workshop started, he offered to move it outside. His was the last workshop of the weekend, and the sun was shining, so we all went out into the fresh mountain air to listen to Nathan talk about how to build an audience and a product, and how those two tandem tasks interact.

Building an audience always starts with a problem. Your product should solve a problem that lots of people have, and positioning your product as the solution to that problem is a clear path to successfully building an audience. Once you start talking about a problem, and offering solutions to that problem, the people who are actively searching for solutions will find you and follow you.

During the workshop he asked us to make a list of 10 people who have the problem we can solve and could by our product now. This exercise made my audience feel very tangible – it was just a grouping of these dads I knew, who all shared a specific set of problems.

The great thing about getting so specific is that you don’t need a massive audience to draw from. “If your product is solving a specific problem,” Nathan says, “your list doesn’t need to be that big.”

This made me realize that if the problem you solve is vague, you need a large audience to convert a small section of it. You can win bigger with a smaller audience, and a higher closing ratio, if you get really specific about the problem you solve.

Nathan recommends building an audience around a validated product first – then you know you’re building the right thing. And the only way to really validate your product isn’t to talk to people about your idea – it’s to ask them to pay for it.

Talking to someone will get you some enthusiastic feedback, and it might not even be authentic. But when you ask people to hand over their credit card, he says, then you find out what they’re really thinking.


In developing an audience, you don’t want to just build any audience – you want to build an audience that will buy your product. The best formula, Nathan says, is to teach a skill that makes money to people that have money. People will immediately see the return on investment if your product will make them more money; and if they have money already, they will be able to buy it.

You can find your audiences by figuring out where they already hang out. Go back to your list of 10 people, Nathan advised, and ask them two questions:

  1. What’s your biggest problem relating to this subject?
  2. Where do you go online to research solutions?

By asking these questions, you have your target audience do your research for you.

Write a blog post about the problem, Nathan said, and provide a list of all the places where the people with that problem hang out. Drive traffic from there, and your blog post becomes an information hub for people researching the solution you want to provide. It’s a fantastic, SEO-friendly way to build an audience, and to get goodwill from other websites in your niche (because you are providing them with backlinks and traffic).

Finally, Nathan closed with his Tiered Pricing revelation, which came as an offhand comment from Chris Guillebeau. “Tiered pricing has worked really well for me,” Chris said, almost in passing, and Nathan seized on it. He applied that idea to his latest product, a $39 ebook, and positioned a training module upgrade for $99 and a $249 top tier version, and his revenues went through the roof.

Pioneers on the Digital Trail

Just before the Pioneer Nation event, my kids took a field trip to the Barlow Road, a section of the Oregon Trail near the present-day Resort at the Mountain, where PN was held. This road allowed Pioneers to stay off the treacherous Columbia river for the final leg of their journey to Oregon City. There were historians camping out up there for a 10-day exhibit, eating the food that the Pioneers ate, setting up camp from the wagons, and demonstrating what life was like as a Pioneer.

It got me thinking about the similarities between the Pioneers on the trail more than a century ago and the life of a Digital Pioneer in the online world. Here’s what I’ve realized:

  1. The time on the trail is just a phase. Pioneers didn’t travel nomadically and live in their wagons indefinitely. They were heading somewhere, they had a goal up ahead, and when they reached that goal, everything changed. They just had to keep their wagon going until they made it.
    • A business in the startup phase only has to last until it reaches a level of self-sustainability. Until then, it’s a rickety wagon, following a map that others have laid out before them, and maybe it reaches its destination, maybe it doesn’t. A lot of it has to do with luck and resilience.
  2. The only resources you have on the trail are what you bring with you, what you can forage, or what another Pioneer on the trail can provide. You don’t have access to the resources of the promised land far ahead of you, not yet.
    • After leaving a job to start a business, you lose access to the insurance and benefits that came with your job, so stock up on dental visits before you leave. You can get things like funding and investors after you’ve made your business into a workable endeavor, but until then, you just hold on and make do with what you’ve got.
  3. Setting up a wagon is a costly endeavor. Families had to liquidate everything they owned, and buy everything they could possibly need from civilization, before moving out onto the frontier.
    • Setting up a business, while it can be done on the cheap, still requires a liquidation of time and energy, and a re-investment of your life in the new business. When you officially start, you can’t go back for supplies, you need to have them with you or do without.
  4. Pioneers survived because they worked together. They were all on the same grand adventure, and the small community they built allowed them to band together against the elements.
    • The greatest resource someone has in the startup phase of their business is the other people on the same journey.

Out on the frontier, the most reliable understanding you can get about the terrain doesn’t come from maps – it comes from the stories and advice of those who have made the journey and survived.

That’s why this conference was so full of actionable advice – it got us out of the wilderness of the Trail, and into the Trading Post where we could get some directions, supplies, and advice.

So, what did you think?

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