This is not the first time I’ve written this newsletter from a ski lodge :-)
(I’ll explain what I mean in a moment…)
But first…
Last night, I got back to Vermont after twelve days of travel in Austin, Texas…
And as you’ll see in a moment, my twelve days away were filled with takeaways and reminders…
(As well as pages and pages of handwritten notes …)
And after five back-to-back events…
A dozen different private dinners…
Six different presentations from stage…
(Not to mention nearly fifty hours of sessions participated in…)
I thought I’d share my biggest lesson from each day.
(Because I think you might find at least one of these helpful…)
So without further delay…
Twelve days.
Twelve takeaways.
Let’s dive right in…
1 | The last mile is the one that matters most. (Day 1 of 12)
I kicked off my trip to Austin, TX with an interview with my buddy Hal Elrod, whose newest book Miracle Morning After 50 releases this week! (Go out and grab your copy today.)
Hal invited me to be on his podcast to talk about my upcoming book, Return to Real and the core thesis behind it – which really impacted his thinking when I shared in a mastermind we’re both part of…
Now, we could’ve easily done this interview over Zoom.
But instead, I offered to travel 2,000 miles from Vermont to Texas so we could get together in person in the recording studio.
(After all, Return to Real…. right?)
The irony of making all this effort to meet in person – was that my Uber from the hotel to the recording studio was a “person-less” Waymo vehicle.
Have you been in one of these vehicles before? There is literally no driver. It is surreal.
We don’t exactly have these floating around the Green Mountains of Vermont – so this was my first time. Hence the nerdy thumbs up :-)
Making the big long trek from VT to TX was a reminder that in life:
The last mile is the one that matters most.
Like, when you’re speaking…
A solid talk is not enough. You’ve gotta stick the landing. Standing ovations happen in the last 60 seconds.
Or when you’re writing…
Most writing is “fine.” The last mile is all about obsessing over each word. People don’t remember books – they remember sentences.
Or with relationships…
You can have nine great touch points… but one sloppy “last mile” moment (e.g. relying on AI to write that email reply) erases the whole thing.
Which brings us to…
2 | You may be the average of your group. But a committed group will raise the average together. (Day 2 of 12)
Pictured here at Front Row Dads Live – with my Front Row Dads “Band” – whom I’ve mentioned in several past issues…
Spending time at Front Row Dads Live with my “band,” I was reminded of the adage we’ve all heard a billion times:
You are the average of the five people you spend the most time with.
But I think there is more to it than that.
If you pick an area of your life that you want to improve:
Being a better father.
Being a better investor.
Being a better writer.
And find a group committed to improving in that area of life or business.
While you may be the average of that group…
A committed group will raise the average together.
3 | If you can't laugh at yourself in public, you'll never survive being real in private. (Day 3 of 12)
After taking the stage to deliver my first keynote at FRDL…
If you look at the image above – and the screen behind me on stage, you may notice that they put two “bearded guys in flannel shirts” on stage on the same day…
I joked that I was the “Dollar Store version” of Cary Jack – or that maybe Cary was the “AI-enhanced version” of me.
(Cary has worked as a professional model in real life. I…. have not.)
It was a funny moment that got a bunch of laughs, but more importantly it was a reminder:
If you can’t laugh at yourself in public, you’ll never survive being real in private.
Which brings us to…
4 | Enjoy the mess, for one day it will be gone. (Day 4 of 12)
I have pages of notes from my days attending Front Row Dads Live and literally dozens of takeaways…
Like in last week’s issue of The Digital Contrarian, I wrote about your True Self vs. Strategic Self and the “Four Archetypes” we fall into for coping with our unmet needs as children.
Deep stuff.
(And we didn’t even begin to scratch the surface.)
But today, I’ll share a simple one that hit me hard:
One day the mess will be gone. The kids will be grown. And there won’t be anyone creating the messes anymore. Enjoy it now, for one day, you will miss it.
Enjoy the mess, for one day the mess will be gone.
5 | The AI Backlash is coming. Are you ready? (Day 5 of 12)
After Front Row Dads Live wrapped up, Joe Stolte invited me to stop by his Prime Elite mastermind AI Event for a fireside chat.
In our chat, I shared why I believe there is a growing argument for distancing your brand from AI-generated content.
When you follow the comments across social media online…
Outside of AI-fanboy communities, the general public already has an undercurrent of contempt toward anything AI-generated…
And next year, when we begin to see more AI-related layoffs (already 162K and counting in the US alone) – and people’s household incomes are impacted…
The last thing you may want to do, is to put your brand in the crosshairs of anti-AI protestors looking for an easy target to pick.
The AI Backlash is coming. Are you ready?
(BTW – Speaking of next year, stay tuned for my 2026 Predictions. I’m planning on hosting a Town Hall early next year after the holiday season. I’ll send an email to register as we get closer. In the meantime, keep your eyes peeled.)
6 | Hosting a dinner for friends will offer a better ROI than spending the same amount of cash on Facebook Ads. (Day 6 of 12)
The evening of Day 6, I hosted a private dinner for a group of entrepreneurs and founders – including both old friends and several new acquaintances alike…
Huge thank you to Brad Weimert for lending his team to help organize, and for making his lake house available for this.
It was a reminder that spending a little money to host a dinner like this that builds real relationships…
Offers a better ROI than spending that same cash on Facebook ads (or probably any form of online advertising, for that matter…)
A question to reflect on is this:
What’s your annual marketing budget?
And what percentage of that do you invest in hosting meals and gatherings like this??
7 | Heart. Humor. Humanity. And.... Hilarity? (Day 7 of 12)
I was invited by Justin Donald and Ryan Casey to deliver a keynote session at their annual Lifestyle Investor Summit.
And after Justin introduced me – with what was one of the kindest, most thoughtful introductions…
I promptly proceeded to roast him on stage to raucous laughter and applause.
(All in good fun, of course.)
After seeing Philip McKernan use humor so effortlessly throughout each of his sessions at FRDL – and how effective that use of humor was in delivering his message…
It’s inspired me to want to use more humor in the presentations I deliver as well.
I’ve always added a dash of humor in most every session.
But I’ve been under-seasoning.
And it’s an ingredient I want to more intentionally wield in 2026 and beyond.
8 | How to raise your kids to be multi-millionaires (Day 8 of 12)
The next day I was invited back on stage along with Ryan Thacker to lead a session on how to raise children to become investors…
I shared the four step plan Tylene and I developed 6 years ago, and are actively using to help our boys to become lifelong investors, starting at an early age.
Step 1: Learn by Reading – We started by reading aloud as a family, books like Rich Dad Poor Dad – when the boys were 5 and 7 yrs old.
Step 2: Learn by Playing – We then started playing board games like Rich Dad Poor Dad’s “Cashflow for Kids” and eventually “Cashflow for Adults” to learn the fundamentals of investing.
Step 3: Learn by Doing – We then helped the boys each make their first real estate investment, which generates about $167/month in passive income, each. It was their first of many investments.
Step 4: Learn by Forming Habits – The boys are allowed to spend 25% of their passive income, and are required to reinvest the remaining 75%. This has led them to each design their own diversified stock (& crypto) portfolios, which they add to each and every month.
(And this is just the beginning.)
Look, we’ve all seen the power of compound interest.
But have you seen the growth of Warren Buffet’s wealth?
Check it out…
The power of compound interest is profound.
This is true with money.
It’s also true with relationships.
Most people don’t have the patience to stick with anything long enough to get meaningful results.
Whether that’s investing money to build wealth…
Or writing a weekly email to build a relationship with your audience…
Most people start at the equivalent of Buffet at 14…
And give up at the equivalent of Buffet at 15…
And then when someone who sticks with it achieves something meaningful -seemingly overnight…
They wonder “what’s the secret…”
And if you think you’re too late??
Remember, the best time to get started was twenty years ago…
But the second best time is today.
(BTW – If you’d like to join our priority list to work with my agency to craft YOUR weekly “Source of Truth” email newsletter and build YOUR “Strategic Content Ecosystem” in time for our Jan 2026 new client cohort, you can fill out your application here.)
9 | This year: What's strengthened you? What's surprised you? Where do you need to evolve? (Day 9 of 12)
Speaking of investing…
On Day 9 I attended my Tiger 21 investment group meeting.
And while what we discuss inside these meetings is confidential, I’ll share with you a macro-economic infographic (available publicly) that we examined together as part of a discussion on where things are headed in 2026…
In addition to this discussion, in our meeting, looking back at this past year, we each explored (and shared our answers to) the following three questions:
- What’s strengthened you?
- What’s surprised you?
- Where do you need to evolve?
As we approach the last few days of the year, I think these are three questions worth reflecting on for all of us today…
What are YOUR answers to these three questions?
10 | $100M Business Lessons Learned: No deal goes in a straight line. (Day 10 of 12)
While catching up with my friend and fellow entrepreneur – Brian Moran (founder of SamCart) over breakfast…
We reflected on something I had written in my notes from my Tiger 21 meeting the day before:
No deal goes in a straight line.
By virtually any measure, Brian has built one of the most successful software companies in his industry.
He’s raised over $100M in funding.
He’s generated tens of thousands of customers.
And yet…
His story of success has been filled with harrowing near-misses…
(And perilously close calls…)
In fact, Brian took me through the rollercoaster ride he’s been on since he and I last caught up in person…
And it’s a story that is not for the faint of heart.
All to say…
It was a sobering reminder that the razor thin line between success and failure is often defined by a few pivotal moments that test your fortitude and resilience…
The same is true for all of us.
11 | If it requires daily discipline, it's a badly designed system. (Day 11 of 12)
My final presentation from stage was at the Lifestyle Investor “Tribe of Investors” event on Day 11 of my trip.
And it was on this day that I was reminded that…
The most successful people don’t just “try harder.”
They design their environment so they need less willpower in the first place.
This is what makes forming successful habits (in any domain) inevitable.
Simply put:
If it requires daily discipline, it’s a badly designed system.
Which leads to the question:
What’s one habit that’s keeping you small right now and no longer serving who you want to become?
This brings us to the final one for today, which is…
12 | A man admits when he makes a mistake. And even good dads screw up sometimes. (Day 12 of 12)
After being away for 12 days, I asked my boys what they wanted to do when dad got home:
Bradley: “Play the game Cashflow Quadrant!” (Really)
Henry: “Go skiing at opening weekend at (our local mountain)!”
(Hence why I’m writing this newsletter from a ski lodge, after getting in a few hours on the slopes earlier this morning…)
(In case you’re wondering, Tylene gets a much deserved day off after holding down the fort for nearly two weeks while I was away.)
Now…
If you read my newsletter from last week – [Issue #077] True Self vs. Strategic Self – and wondered what happened upon my return home with my son…
Well, I’m happy to report that my son and I had a really good conversation.
I apologized for what I said and how I handled things before I left. I explained that a man admits when he makes a mistake.
And that even good dads (and more generally, good people) screw up sometimes.
We hugged…. and cried.
And it was a beautiful moment.
* * *
So when I end each issue of this newsletter with the words:
“Remember to hug the ones you love….”
I really do mean it.
In fact, I’ll wrap today’s issue by asking you this:
Who do you need to hug today?
And who in your life might need…. an apology?
Be brave.
And don’t wait.
You never know if this is going to be your last chance. ;-(
* * *
Okay, I’ll leave you with that for now…
Remember to hug the ones you love…
(Really.)
And have a great weekend.
Until next week,
Ryan :-)
