The Digital Contrarian™

Ryan Levesque

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The Digital Contrarian™

Ryan Levesque

Issue #040

| The Digital Contrarian™

Make Your Move (Before It’s Too Late…)

What Happens When Cycles Collide: Understanding Why This Moment Feels So Intense & How to Make Your Next Move (Before It's Too Late...)

Ryan Levesque

14 min read

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Let me ask you something:
 
Doesn’t it feel like everything is moving so fast right now?
 
Markets shifting weekly. Technology evolving faster than we can process. Business models that worked at this time last year now suddenly obsolete.
 
If you feel a sense of pressure trying to keep up with it all…
 
It’s not just you.
 
And it’s not just random that this is happening now.
 
In fact, there’s actually a reason for this and the timing of it all – and it has to do with cycles.
 
More specifically:
 
What happens when multiple cycles collide like what we’re experiencing at this moment in history.
 
Let me explain…
* * *
As part of the research for my upcoming book, I’ve been doing deep dive research into Cliodynamics, Strauss-Howe Generational Theory, and more broadly….
 
The history and nature of financial, economic, and technological cycles.
 
And what I’ve come to appreciate, is that cycles don’t operate in isolation.
 
They move like coordinated waves.
 
And sometimes, when the timing is just right
 
The multiplied forces of these waves come together all at once in such a way that creates sudden, massive amplification…
 
Like when a bunch of people come together on a trampoline in a coordinated way to launch a single jumper 50 feet into the air like this insane YT video with over 37M views:
And that’s exactly where we are now.
 
In fact, if you have a business…
 
(Especially one that is currently generating at least six or seven figures…)
 
And if you have a desire to scale your company… sell your company… or segue into your next act…
 
And if you’re feeling a sense of urgency to make your next move before the seeming “window of opportunity” in front of you closes…
 
I can tell you from the conversations I’ve been having with my clients recently, that you’re not alone.
 
And your instincts are probably right.
* * *
In fact, this theme has been coming up so often in conversations over the last few weeks… That I’ve decided to host a free, live Zoom Meeting later this week that I’m titling:
(More on that in just a moment…)
* * *
But first, on this subject of “Cycles Colliding” – and how to make your next move before it’s too late – I think it’s important that we begin today’s discussion by exploring…

1 | The Physics of Resonance (and the Business of Collapse).

Now, if you remember from your high school physics class, when two waves with the same frequency align, they create something called constructive interference, which visually looks like this:
This is where instead of neutralizing each other, the waves combine to create even bigger waves with a higher amplitude. 
 
It’s the phenomenon behind musical harmonics, swing sets, and even catastrophic bridge collapses (like the famous Tacoma Narrows).
 
Now, I promise not to get too nerdy with this…
 
But here’s the important (and highly-relevant) twist: 
 
Human systems behave in the same way.
 
Economic cycles. Technological cycles. Market cycles. Cultural cycles. 
 
(Even personal energy and life seasons.)
 
They all operate in waves.
 
And when these cycles align?  
 
You get amplification.
 
(Like the trampoline example.)
 
When they conflict? 
 
You get collapse.
 
(This is the concept of “resonance” at work – for better or worse.)
 
 
“If you can learn how to spot the non-obvious patterns others aren’t seeing, then you can anticipate what’s coming before anybody else… It’s like being able to see the future in ways to which other people are completely blind…”
 
And as Strategic Advisor to a growing number of Private CEO Clients, I’ve started to share with these clients a pattern we’re seeing right now of overlapping cycles, which explains much of the turbulence we’re experiencing in the market (and which for some businesses represents a closing window of opportunity to take action…)
 
And it all has to do with…

2 | Three Cycles Converging Right Now.

The first of these cycles is…
 

Cycle #1: The AI Hypercycle (aka Schumpeter’s “Creative Destruction”)

In [Issue #033] The Coming Collapse?, we confronted the sobering reality that AI is putting virtually every white-collar profession at risk – perhaps far sooner than many predicted just months ago.
 
AI isn’t just a cool new piece of technology. 
 
It’s a full-blown technological revolution.
 
It’s eroding pricing power, eliminating middlemen, and automating foundational layers of value creation. 
 
And if you work with information for a living (e.g. as a marketer, coach, consultant, thought leader, educator, writer etc. ) or if you operate in a sector that “greases the wheels of capitalism” (e.g. accounting, legal, finance, etc.) you’re likely already feeling this.
 

What is Schumpeter’s “Creative Destruction” Exactly?

Creative Destruction – If you’re not familiar with the concept, (often associated with Austrian economist Joseph Schumpeter), is the uncomfortable truth that the greatest human progress doesn’t come from improvement. Instead, it comes from obliteration – as new technologies make old ways obsolete, not with a feather and a whisper, but with a wrecking ball and a scream.

 
Now, the AI wave and wrecking ball is undoubtedly powerful.
 
But it’s not the only wave hitting us right now.
 
Which takes us to…
 

Cycle #2: The Economic Tightening (aka “Juglar Cycle,” Late Stage)

 
According to economic cycle forecasting, we’re now likely in the “late expansion (approaching contraction)” phase of the medium-term Juglar Economic Cycle (which is a cycle that typically lasts 7–11 years).
 

What is the “Juglar Cycle?” 

The Juglar Cycle – If you’re unfamiliar with the concept, (which gets its name because it was first identified by the French economist Clément Juglar), is the boom-bust rhythm that drives modern economies: A mid-length cycle (7–11 years) where exuberant expansion is inevitably followed by a sobering correction – not because something broke, but because that’s just how the system operates.

 

What evidence supports that we’re in the “late expansion” phase?

 
Well, a few things…
 
Growth is slowing (e.g. US GDP slowed to 2.3% in Q4 2024, down from 3.1% in Q3). Credit is tightening (banks are pulling back on lending) and delinquencies are rising. At the same time, confidence is wobbling (Equity markets corrected by more than 10% earlier this month, indicating investor unease).
 
Additionally, earlier this week, the US Federal Reserve held rates steady for the second straight quarter, but quietly lowered its growth projections for 2025. Lending standards remain tight. Household and government debt levels are elevated.
 
Consumer demand is keeping things afloat – but just barely – and this is often the final leg of expansion before economic contraction.
 
The above mix represents classic pre-contraction conditions.
 
We’re likely in the “autumn” of the Juglar cycle – where growth is still visible but fragile, and early signs of contraction are beginning to surface.
Or in farming terms, we’re at the “harvest looks good, but the frost is coming” moment…
 
And here’s the rub:
 
This is all happening while the AI wave is still accelerating.
 
Which takes us to…
 

Cycle #3: The Long Wave (aka “Kondratiev Expansion Phase”)

At the same time, we’re likely in the early expansion phase of what’s known as the longer-term Kondratiev Wave, driven by the convergence of the AI, biotech, clean energy, and decentralization “Megatrends”, a concept we explored together in [Issue #031].
 
In contrast to the medium-term, 7-11 year Juglar cycles, the longer-term Kondratiev super-cycles span 40–60 years.
 
And according to some analyses, the post-2015 rise of agentic AI and synthetic media marks the beginning of a new “spring” season of this longer cycle – a time of foundational innovation and infrastructure build-out.
 

What is the “Kondratiev Wave?” 

The Kondratiev Wave  If you’re unfamiliar, refers to a long-wave theory of capitalism (proposed by Russian economist Nikolai Kondratiev) that suggests the entire economy moves in 40–60 year tides – not ripples, but massive swells – driven by clusters of breakthrough technologies that first ignite frenzy, then leave wreckage, then quietly rebuild the world.  

By most interpretations, we’re entering the 6th Kondratiev Wave, which you can see in the table below, kindly produced for us by ChatGPT:

 
Now, if this is true (that we’re entering the early expansion phase of this next Kondratiev Wave), then we’re likely entering an era of massive opportunity.
 
But only for those positioned to ride the wave.
 
The danger here is that short-term contraction (Juglar, 7-11 year cycle) can obfuscate the early-stage opportunity (Kondratiev, 40-60 year cycle) and cause businesses to make the wrong moves…
* * *
But all that said…
 
There’s one more cycle that doesn’t show up in the data.
 
A fourth cycle that’s arguably more important than all the rest…
 
Your internal cycle.
 
The cycle you’re living right now – not your business, not the market – but you.
 
Where YOU are in this season of life – and where you want to go next…

3 | The Next Phase of YOUR Cycle.

The CEOs I am working more and more with typically have a deep desire to:
 
  • Build a business that’s both financially successful AND deeply fulfilling…
  • Create something sustainable and meaningful in an increasingly AI-driven world…
  • Stand out authentically in an overcrowded digital landscape…
  • Future-proof their business against disruption…
  • Find ways to thrive that align with their values…
 
And in terms of their own personal cycle, they are typically in one of three phases of their journey:
 
  1. Scale
  2. Sell
  3. Segue
They’re either looking to…
 
  1. Scale their business – and want help with sales and marketing to squeeze as much profit from it as they can to maximize the window of opportunity in front of them…
  1. Sell their business – and want help navigating the process, and help both positioning and structuring their company to get the biggest payday possible before their window to sell closes…
  1. Segue into their next act – and want help making the shift to their next adventure in a way that balances their pursuit of meaning and the economic realities of their life…
And often times, it’s a combination of all three of the above…
* * *
Now, I feel incredibly fortunate to have gained a tremendous amount of wisdom and perspective navigating these three phases of this cycle myself in my own life personally, first-hand over the last few years:
 
Scale: Learning how to scale a 7x Inc. 5000 company from nothing – reaching ~$20M/year in top line revenue, and over $5M/year in bottom line EBITDA.
 
Simply put: I’ve learned what it really takes to scale a company from nothing as founder, business owner, and CEO, and how do it while generating a meaningful profit for the business.
 
Sell: Learning how to actually navigate the incredibly complex M&A process, working with investment banks and private equity – as well as bouncing back from losing two deals, including a $70 million offer – and still achieving a significant financial exit in the end, in a less than ideal macroeconomic environment.
 
Simply put: I’ve learned what it really takes to bring a business to market and what’s necessary to actually get your company sold, even when the market conditions are less than perfect.
 
Segue: Learning how segue into that next act. Stepping away from running a $100M+ business, and choosing to shift to a simple life on a farm built around family, immersed in nature – with work days spent writing and advising a handful of private clients.
 
Simply put: I’ve learned what it really takes to step out of the economic spin cycle so many get sucked into forever, and make that shift to that “Second Mountain” of life focused around meaning, purpose, and doing what you love spent with the people that you love.
* * *
Now, the reason I tell you all this is because as I mentioned at the beginning of this newsletter, this week I’ve decided to do something special.
 
I’ve decided to host a rare public session (free) where I’ll be revealing live…

4 | What I Wish Someone Had Told Me Before I Sold My Company.

I’ve decided to break the silence and share insights that I’ve never shared publicly before in a Live Zoom Session where I’ll be revealing:
 
  • The 3 things I now wish I knew before selling my business…
  • The mistakes to avoid if you want to maximize the value of your company before you sell (and when you need to make those moves.)
  • The Hidden pitfalls in the M&A process no one warns you about…
  • A $70 million dollar lesson learned – and how to avoid making the same mistake I made in your transaction…
  • What I’ve learned after stepping away from a $100M+ business and choosing a life built around “The Return to Real” – focused on family, purpose, and meaning…
  • And for those who might be interested – how to work with me privately – whether you’re looking to get help to scale, sell, or segue into your next act (or do all three…) and how to know if you and I are a great fit to work together…
 
 
Note: This is a LIVE session with a hard cap of 300 Zoom attendees. Because this topic is so specific – I have no idea if this is going to fill up or if five people are going to show up – but I highly recommend blocking off your calendar and showing up at least five minutes early just in case…
 
And by the way…
 
If you don’t have a business right now – you can sit this one out.
 
This session is NOT going to be helpful for you if you are still figuring out your market, your offer, or you don’t currently already have a six, seven, or eight figure business…
 
This is going to be an advanced session – and I won’t be slowing down to cover the basics.
 
That said…
 
If you’re at an inflection point in your business right now – whether you’re scaling, selling (or seeking to get your life back)…
 
And if you do have a six, seven, or eight figure business right now – I’d like to invite you to take one of the limited seatsfor this session…
 
This might be the only time I ever host a session like this (I haven’t yet decided) – and if you need to adjust your schedule to be there – I can promise you that this is one worth moving your schedule around so you can be on this Zoom call…
 
* * *
Okay, I’ll leave you with that for now…
 
Have a GREAT rest of your weekend…
 
Remember to hug the ones you love…
 
I look forward to seeing you on the session…
 
And in the meantime…
 
Until next week,
 
Ryan :-)
 

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The Great Sea Change

The Great Sea Change diagram from Return to Real