How Tim Denning Uses Vulnerability As A Strategy To Out-Earn "Perfect" Influencers
While Denning wins by sharing his struggles and failures, don't make the mistake of copying him without understanding what really drives his success
“Hey honey– say hi to Tim Denning.”
On vacation with family over the holidays, I had just finished my first successful writing challenge, and Tim Denning had invited me to a Zoom meeting.
Tim was relaxed, friendly, and at ease, inviting me to take the next step, from the 28-day writing challenge to working with a group of writers who were already taking their writing to the next level.
After three failed writing challenges, I finally made the leap from occasional, sporadic one-off posts to consistently posting 28 days in a row.
What was my secret? Having creator Tim Denning and his business partner, Todd Brison, in my corner.
Finding My Way
I had tried several other writing challenges, but always trailed off after a few good days.
And this one should never have worked. Coming through the end of November, I had every possible excuse– Travel, work, holidays. And yet with Tim Denning and Todd Brison’s structured approach and accountability, I succeeded.
And this was the first step in a set of deep mindset shifts in what was really “possible” with writing.
The consistent posting had exponentially spiked my LinkedIn following, and I started my Substack newsletter.
But it all came back to showing up and publishing something every single day.
Are You In, Or What?
And now Tim was inviting me to take the next step.
I was flattered.
I discussed it with my wife, as it represented more than I’d ever spent on a writing course.
And ultimately dived in for my first year of commitment to writing as part of Tim’s “Badassery Academy.”
As we’ll see, my experience learning from Tim and Todd for over a year gave me a front-row seat to watch how Tim actually succeeds, instead of what people think is the reason for his success.
Pay attention, because the difference is everything. Most people think Tim succeeds because he's vulnerable.
After a year inside his system, I learned something completely different.
Who is Tim Denning?
Here's the reality behind Tim’s approach, and why most people completely misunderstand who he is or what he does.
In the era of the carefully-cultivated “personal brand,” Tim Denning has built a seven-figure creator empire by doing the exact opposite: he leads with his darkest moments and failures.
While other creators post polished LinkedIn posts and curate perfect Instagram feeds, this Australian ex-banker has generated over 1 billion content views by weaponizing his vulnerabilities.
Tim’s partnership with ghostwriter Todd Brison has created a $1.8M+ annual revenue machine that turns their authenticity into a content and connection multiplier.
Reverse-Engineering The Authentic Guru System
My time learning as part of the “Badassery Mastermind Academy” allowed me to see, up close, how Tim Denning has revolutionized the creator playbook.
Let's take a closer look by reverse-engineering how Denning succeeds through the lens of Roger L. Martin's Strategy Choice Cascade to become what he calls "the most prolific personal development writer online today" and build his business.
Winning Aspiration: Freedom Through Radical Authenticity
Most creators want to be seen as successful, posing in front of yachts and Lamborghinis.
Tim Denning wants to be seen as deeply human, just like you.
“Winning” for Tim Denning means “creating lifestyle-first freedom while empowering 100,000+ writers to monetize their online skills and escape the corporate hamster wheel.”
Here’s what blew me away about Tim’s approach: He succeeds by openly sharing failures, gains authority by showing weakness, and builds a distinctive brand through intentional imperfection. Tim doesn’t overthink or stress the small stuff. This strategy works because Tim succeeds by doing what his target audience craves the most: transforming to a successful creator lifestyle while being their true selves.
Unfortunately, most creators write candidly and stop here.
But success requires more than just unfiltered thoughts on a page.
Where to Play: Writing the Way to Freedom
Tim doesn't try to serve “aspiring writers.”
He serves ambitious corporate professionals who’ve gained valuable knowledge but feel trapped and lack the frameworks to monetize it.
His mission statement reflects this strategic targeting:
"Each of us has a full-time income stuck in our heads.
Working a job is level 1.
Monetizing what's in your mind is level 2."
Platform strategy: Denning operates what he calls "extreme focus" on three primary platforms where "millions of people are," in priority order from “owned” (email list) to social media prospects and open outreach. Note how social media feeds email list growth and revenue:
Kit and Substack Email as the Main Hub: (400k+ subscribers): Segment audience through Kit and regular emails; manage his main "Unfiltered" Substack for his owned (and partly paying) newsletter audience.
LinkedIn for Professional Distribution and Outreach: (572,000 followers): Primary professional networking and lead generation
X (117,000+ followers): For continuous outreach, daily engagement, and community building
Denning posts daily across these three channels with distinct, targeted content strategies tailored to each platform.
How to Win: The Vulnerability-Volume Combination
Tim wins through strategic choices that seem contradictory: radical emotional transparency, together with a deep understanding of psychology to teach and build community.
Systematic vulnerability: While other personal development creators pretend they have it "all figured out," Denning openly shares struggles. This open sharing creates the "grade ahead" effect. If you’re struggling in middle school, you’ll learn more from a ninth-grader than from some “perfect” college student.
Sheer volume as competitive moat: Denning publishes more content in a week than most creators produce in a month. By consistently publishing 20 pieces a week while competitors are barely managing 3, you're not only increasing the odds of having something go viral, you're building a body of work that’s almost impossible to catch up to.
This comes back to the old “Can’t/Won’t” advantage: Other creators simply can’t, or won’t be able to keep up.
Premium community & pricing model: Rather than competing on price, Denning positions his “Bad-Assery Academy” as a premium offering with selective enrollment. Course enrollments are driven by scarcity, as they’re only open to 100 students at a time, for a few weeks per year. Denning offers a mix of annual subscriptions with monthly and even weekly options.
AI-Aware and Ready: Denning is already moving beyond traditional information products, anticipating AI's disruption of the info-product space:
"AI means we will buy less information. Don't sell information like a sucker."
Anti-niche differentiation: While every other creator advocates for naming and claiming a “niche,” Denning attacks that with his "anti-niche" approach:
"Niching down is stupid. We are multi-topic humans."
Tim covers banking, personal development, writing, investing, and entrepreneurship, then niches down with specific offers.
I personally think Tim has the luxury of not having to niche down because his offers are related to the writing practice at the very core of every niche.
Again, this is where you have to watch carefully what Tim does and what motivates people to buy.
Capabilities: The Partnership Multiplier Effect
Denning's capabilities are world-class: systematic content production, financial chops from his banking background, and an almost supernatural ability to transform personal pain into viral content.
But his partnership with bestselling author and ghostwriter Todd Brison creates capabilities neither could have achieved alone:
Tim: Vulnerability, content creation and posting volume, marketing, financial expertise, audience building, combined with a unique ability to “read the room” and write content tailored to each platform
Todd: Technical writing, structure, traditional credentials, five-star course-building, quality control, book publishing experience
Tim and Todd’s strengths complement and multiply each other’s effectiveness.
The partnership works because it solves the fundamental creator dilemma of trying to be both perfectly authentic and perfectly authoritative.
Tim provides the authenticity that attracts audiences, while Todd provides the authority that creates premium materials and instruction that justify the duo’s premium pricing.
Most creators have to choose one or the other.
Management Systems: Systems and Metrics That Matter
There are two areas of systems and metrics I see Tim focusing on to measure and continuously improve his business.
Content Systems: Structured writing schedule (Wednesdays and Saturdays) with systematic approaches to ideation, outlining, and publication across multiple platforms.
Business metrics that matter:
Spread revenue across more than seven active sources for diversification
Limit course enrollment to just 100 students per cohort to maintain quality and that “personal” touch
Watch and understand what affects students’ subscription retention at different timeframes and price points
Continuously monitor and keep course ratings and reviews in the 4.9-5 range
By focusing on subscriptions, premium pricing, and limited enrollment, Tim creates predictable cash flow with just three people.
Working lean like this enables Tim and Todd to focus on high-volume content and high-quality course creation while building actual wealth, not just revenue.
My Experiences Under Tim and Todd
But here's where watching Tim from the inside taught me something crucial about the gap between what he tells people to focus on and what actually drives success.
He sells courses, even though he says it’s for “losers.”
As a member of his Badassery Academy, I kept getting “cross-” and “up-sold,” and prices were continuously increasing.
Yet Tim’s income has skyrocketed due to one thing: Premium weekly memberships.
Tim and Todd charge up to $250+ a week to be part of a high-level community with greater access and more personalized coaching.
I get it – Investing in a weekly membership makes sure the person subscribing gets off their butt and actually does something.
But for someone with a full-time job, it would seem almost impossible to get the full value at those prices.
Uneven Success
As we saw with the “authenticity” piece, I’ve seen the less-successful students look at what Tim’s doing and base all their writing on oversharing without a clear point or goal.
They have areas of expertise, but it doesn’t work for them like it does for Tim because he’s selling the skill of writing itself.
The hardest thing for Tim’s students is coming up with a clear problem to solve and a person to solve it for who has the money to pay for it.
And then creating a product and an offer to solve that problem.
And then finding readers to read their content and establishing rapport and trust before naturally making their offer.
For Most Writers, Vulnerable Means Broke
No, most people stop at the candid thoughts.
To Tim and Todd’s credit, they do work hard with everyone to help them improve their writing and focus on the business aspects of sales and making offers.
But some people have a harder time converting their skills into an offer.
If you’re writing raw, unfiltered stories yet don’t know why you’re not getting readers or making any money, this might be your problem.
The Real Lesson: Follow What Tim Does, Not What He Says
What surprised me most was Tim's most successful students weren't the ones sharing their deepest traumas.
They were the ones reverse-engineering his business model.
The failed students thought Tim succeeded because he shared his struggles. The successful ones realized Tim succeeded because he turned his struggles into a systematic business model.
While people were pouring their hearts out and writing platitudes about butterflies and rainbows, the winners were quietly watching and re-watching Tim and Todd's sessions on what “selling” really means, writing compelling headlines, how to structure a content calendar to maximize writing effectiveness, and their offers and pricing strategy.
Vulnerable and Contrarian With A Purpose
They realized Tim wasn't just "being vulnerable."
He was using vulnerability to get readers to the top of a marketing “funnel.”
The students who never gained traction and gave up? They heard "be authentic" and started oversharing without a clear strategy. They missed that Tim's vulnerability works for him because it’s intentional, his stories are chosen for maximum learning value, and to entice people into his entire content and monetization flow.
Seeing who succeeded and who didn’t taught me the most important lesson about learning from any mentor: Don’t get distracted by the superficial part you think makes them successful.
Study what they really do.
What I Learned
My biggest takeaways I learned from Tim were how to write headlines, subheads, and hooks that worked together and reinforced each other, grabbing the reader’s attention and pulling their eye down the page.
And how to apply contrarian points of view in areas like strategy and product management that are typically shared based on an accepted set of standardized best practices.
Tim was also the first person from whom I learned about using Substack Notes to grow their newsletter.
And the importance of always making an ask, and selectively making calls to action for ways you can help your readers at the right time.
Because it’s not selling; it’s helping them because you know you can solve their problem.
Three Powerful Strategic Takeaways for Creators
After a year studying under Tim and Todd from the inside, here are the three insights that transformed how I think about creator strategy:
1. Use Contrarian Vulnerability and Transparency as Strategic Differentiators
Random emotional sharing won’t create a competitive advantage for you.
Because Denning's vulnerability is intentional and strategic, he shares specific failures his audience can learn from, to tell a story and make a point about how he can help you. It’s never a question of just sharing personal trauma for its own sake.
What It Means: Instead of trying to be better than competitors, position yourself as the opposite of what's wrong with your industry. Share how you see things differently.
His Philosophy:
"I price my products at an affordable rate, make them as valuable as possible, and simply ask people to tell their friends if they enjoyed them."
Here’s how you can do this yourself:
Audit industry pain points that competitors ignore
Deliberately choose the opposite approach even if it seems counterintuitive
Focus on an abundance mindset over scarcity tactics
Make transparency your competitive weapon while competitors rely on secrecy
Why This Works: Denning doesn't compete directly with other business educators, and in fact, collaborates with many of them. His anti-positioning creates a category of one where he faces minimal direct competition.
2. Study What Your Teachers Do, Not What They Say They Do
Most of Tim's failed students heard "be vulnerable" and started trauma-dumping.
But the successful ones paid attention and did something totally different.
What This Means: Don't just mimic what you see. Understand the underlying systems that make creators successful.
How I Applied It: Instead of just being “authentic,” or contrarian, I studied Tim's headline formulas, his content distribution strategy, and his monetization sequence. Authenticity is a vehicle to build rapport and trust, not the end destination.
When I studied Tim's content, I saw the underlying formula:
[Contrarian statement] + [Personal story] + [Practical lesson] + [Call to Action}
Most students failed because they only copied either the contrarian statement or the personal story part.
And hardly anyone makes the final Call to Action.
How you can do this now:
Map exactly how your mentor structures their content
Track their business model, not just their messaging
Watch how they make “Calls to Action” and what their exact “Offer” is
Copy the parts of their systems before adopting what you think is they’re trying to say
Focus on the results you achieve, and keep learning where you might be missing something
Why This Works: Most people copy the wrong things because they're easier to see. The real competitive advantage and business-building secrets lie in the systems and strategies teachers explain but might not always emphasize.
3. Apply The Multiplier Effect Through Complementary Partnership
The Tim-Todd partnership demonstrates how complementary skills can resolve tensions that individual creators face (authenticity vs. authority, volume vs. quality, creativity vs. systems).
What This Means: Find someone whose strengths make up for areas where you’re less strong, then structure the partnership so you both grow and win without stepping on each other's toes.
How Denning Applied it: Tim handles the vulnerable storytelling and audience building. Todd brings technical writing credibility, facilitation skills, and a structured approach to course creation. Neither could have achieved their combined revenue on their own.
Non-Obvious Implementation:
Look for potential partners based on strengths that cover your own areas of weakness
Create ownership boundaries that allow for flexibility. Tim predominantly owns audience and content creation, while Todd is the “voice” of the operation and owns course quality.
Structure revenue sharing and incentives to motivate both parties
Let each partner play to their zone of genius while allowing them to grow
Why This Works:
Most solopreneur creators try to be perfect at every part of the job. Tim and Todd’s success proves that complementary partnerships can reduce loneliness and burnout while allowing them to cover for each other when necessary.
Your Turn
I have nothing but great things to say about both Tim and Todd, and I gained a tremendous amount from being part of their community and learning alongside other great creators.
Tim and Todd built something remarkable, and I learned a tremendous amount from both. But the real lesson isn't about vulnerability or authenticity.
It's about paying attention to make sure you understand the complete system, especially the hard parts like sales and offers.
Not just the parts that look easy to copy.
Thanks Mike for the kind write up.
It's interesting that Denning's approach can be analyzed using the "waterfall" principle. However, it seems that he writes more out of his internal problems than because of a business model.
His productivity is not related to planning, but rather to an irresistible need to express himself.
But thank you for this perspective. It would be interesting to see how a "waterfall" based not on "where to win," but on "where not to betray oneself," would look.