Dan Cumberland 🚀

Fractional Product Marketing & AI Implementation

Kit (formerly ConvertKit)

Investor

Zencastr

Gumroad

UpsideBuilders

// B2B SaaS venture studio.  Shipped five products: VideoSnap, TrustScout, SpeedyReviews, GetClear, and SellSimple.

Highlights:
- Launched VideoSnap & TrustScout (see below)
- Oversaw the rapid iteration of product development, strategy, pricing, positioning, and funnel testing, informed by customer interviews in a fast-paced startup environment.
- Made data-driven decisions based on key metrics, identifying projects to prioritize for growth and those to discontinue.

Founder & CEO

VideoSnap

**An UpsideBuilders Venture (see above)**

// AI driven short form social video creation from long form content.  Make your Ted Talk into a TikTok.

Highlights:
- Led agile engineering, machine learning, PMs, and design teams, resulting in the acquisition of the first 100+ paying users within the launch period.
- Engaged in direct customer interviews and monitored the support queue to gain insights and develop clear personas, resulting in the incorporation of valuable feedback into the product discovery and development process. 
- Partnered with sales and marketing teams to develop effective product, pricing, packaging, and positioning strategies, resulting in increased revenue and market share.
- Utilized customer feedback and market analysis to develop a compelling roadmap aligned with business goals and customer needs. 
- Developed effective go-to-market strategies, pricing models, packaging options, licensing, and tiering.

Founder

TrustScout

**An UpsideBuilders Venture (see above)**

// B2B video testimonial collection and management for marketing and social media agencies.

Highlights:
- Successfully onboarded and served 500+ users, contributing to a seven-figure valuation at exit.
- Owned the product vision, product life cycle, roadmap, and backlog, aligning business goals with customer needs to maximize value creation. 
- Identified new use cases and harnessed the full capabilities of the product to drive innovation.
- Collaborated with sales to develop a highly effective webinar, consistently achieving conversion rates of 10%+ 
- Employed testing and rapid iteration to create multiple successful funnels, leading to a 4x increase in customer lifetime value (LTV).
- Iterated on pricing, packaging, and workflow automation, introducing a free trial funnel and an annual upgrade offer, resulting in reduced churn and increased LTV.
- Implemented support processes to capture customer feedback, hired a Support Lead, and guided the team in developing self-serve documentation and processes, leading to reduced support tickets and workload.

VideoRemix.io Video Personalization

// B2B video personalization platform that dynamically customizes video to be unique to each viewer via CRM data or social profile.

- Grew and managed a team of 23 including PMs, engineering, legal, sales, finance, HR, and customer success, while implementing streamlined processes and disciplined product sprints to deliver results.
- Spearheaded the creation of innovative products, resulting in $4.1M in revenue, a 214% increase in company value over 30 months, and a signed Letter of Intent (LOI). 
- Orchestrated and successfully executed a $1.2M product launch, driving a 10x increase in the customer base within 30 days. 
- Optimized pricing, packaging, and customer journey to match customer needs, leading to increased customer lifetime value (LTV). 
- Conceived, designed, and managed the development and launch of six 6 and 7 figure products, providing strategic direction to product, design, and engineering teams, gaining buy-in from internal stakeholders.

CEO & VP of Product

As a founder, I had done it all:

- Founded and sold multiple 7-figure companies
- Managed 11 SaaS products through their lifecycles
- Led cross-functional teams of 20-30 members
- Orchestrated multiple seven-figure product launches
- Doubled a company's valuation in just 24 months

Then I hit burnout.

Overworked and spread thin, I couldn't hold it together.
My love for the business was replaced by exhaustion.

After recovery, I knew I had to find a new way.
I leaned into better processes, automations, and AI.

Now, I help others avoid the painful lessons I learned.

If you're an overwhelmed business owner, you probably:
- Feel like you're drowning in busywork
- Struggle to focus on high-level priorities
- Dream of scaling but can't find the time
- Know AI could help, but don't know where to start
- Miss the passion that drove you to build your business

Here's why this matters:
Time spent on busywork is time lost on growth.
Your team feels the strain, and joy fades.
You have it all on paper - the title, the salary.
But it doesn't feel the way you wanted.

Don't let your dreams slip away.
You don't have to sacrifice passion or health to succeed.

I've been where you are. And I've found a way out.
You can too.

I'll help you scale with AI.
Over 90 days, we'll work together to:

- Reclaim 5-10+ hours of your week
- Build an AI strategy aligned with your values
- Increase productivity and efficiency
- Reduce stress and burnout
- Focus on what truly matters: growth and loving your life

Your decision:
A - Continue drowning in busywork
or
B - Partner with me to build your AI workforce and reclaim your time.

If you choose B - scroll up and book a time with me.

Let's transform your business and help you fall in love with it again.

Your business deserves your best self.
And you deserve the life you've been working for.

Let's build something amazing together. 🖤⚙️

Product and RevOps Consultant

43 hits different.

My wife saw it coming:
"Are you ready?  Birthdays hit you hard."

She knows my patterns.
(Spouses usually do 🖤)

At 23, fresh out of college, I thought I knew the path.
Then came 5 years of finding my way through dark spaces.
Leading youth ministry while administration drained my soul.

Then came my 30s— each birthday a tally mark for loss.
A reminder of how far reality found me from my idealistic dreams.
Each year brought a fresh wave of grief and loss of what could have been.

But something has changed.

As I've entered this midlife space,
I feel more centered than ever.
More settled.
More at peace.

I've been thinking about why.

Maybe it's the therapy.
Maybe it's parenting three wild ones.
Maybe it's having to let go of everything I built and start over.
Maybe there's something in the contrast that the dark and light together bring.
Maybe it's the slow humility of accepting my limits — in spite of limitless ambition.

Or maybe...
It's because every scar has a story.
Every setback taught me something.
Every "failure" brought me here.

Turning 43 today finds me grateful.

Grateful for the battles fought.
Grateful for the things I've seen.
Grateful for the hard earned stories I've lived.
Grateful for the people — especially you — who've been part of this.

I'm done trying to live any other life than my own.
I'm here to be awake to all of it.
The highs.  The lows.  And everything in between.

And if that resonates, then we're in the right place together.

Here's to the middle. 
Here's to being exactly where we're supposed to be.
Here's to the adventures ahead.

🖤

—
👋 Hi! I'm Dan Cumberland 🚀.

I'm building in public my path to 40k MRR as a creator and AI consultant.

I help founders authentically scale their voices and brands, without losing their souls.

Today's my birthday 🤓 🥳

AI Whisperer | Human Amplifier | Building AI Systems That Preserve Trust and Authenticity 🖤

My hand is bleeding today. Literally.

So is my business. Metaphorically.

My $5,000/seat AI coaching cohort was set to launch today.
My prospects list was solid. 11 perfect fits, actually.
But zero were ready to pull the trigger.
So I'm pushing it back 30 days.
And working hard to find the right people.

My hand is bleeding from kettlebell snatches.
And my MRR progress has dropped a full 10k/m.
I'm below 5 figures for the first time in a long time.

Not the outcome that I wanted.
And that can hurt.

But I know a thing or two about pain:
(this isn't my first rodeo)
It's not the enemy.
It's a signal.

We think business should be smooth.
We think growth should be easy.
We think progress should be straight.

But what if we're wrong?

What if the delayed cohort,
The ripped hands,
The missed target,
is exactly what I need?
The ripped hands grow new calluses.
The delayed launch gives me time to find exactly the right people.

What if the obstacle isn't a blocker?
What if it's the way?

This time, I'm not fighting it.
I'm pushing back the launch 30 days.
And finding 8 perfect-fit clients who are ready.

The thing about pain is this:
(here's the unexpected truth)

The events don't hurt.
It's our resistance to them that does.

In fact, who said this is "pain"?
Who said it's not supposed to feel like this?

What if this is precisely where you're supposed to be?
What if this is exactly how building a business is supposed to feel?

What if it's not pain? What if it's progress?

🖤

What "pain" are you resisting today?
How can you embrace it? Relabel it? And let it pass through you?

—
👋 Hi! I'm Dan Cumberland 🚀.

I'm building in public my path to 40k MRR as a creator and AI consultant.

I help founders authentically scale their voices and brands, without losing their souls.

"Entrepreneurship is a trauma response" - Gabor Maté

At least it was for me.

I hated the idea when I first heard it.
Then I looked closer at my own story.
(Surprise: maybe that's why I hated it?)

Fresh out of college, I landed in a role that broke me:
- Under-resourced
- Over-criticized
- Un-supported
- Set up to fail
- Alone

I push through day drowning in anxiety.
Growing sense of dread and depression.
Burnout hovering at the door.

At the time, I blamed myself.
Why couldn't I pull it together?

But that experience did something to me.
It planted a seed:
I never wanted someone else hold that much power over my wellbeing.

(Be careful with those never's)

That's when I realized Gabor Maté was right.
Many of us don't just "choose" entrepreneurship.
We're driven to it by moments that marked us.

These experiences push us toward something different:
- Our own terms
- Our own rules
- Our own safety

Some might see that as negative.
I see it as a gift.

The ones who win at this are the ones who have the drive to.
And that has to come from somehwere.

The pain doesn't have to define us.
Trauma might push us to start,
but it doesn't have to be what drives us forever.

Today, I'm here for the joy.
I'm building for the possibility.
I can't leave behind what brought me here
But I've build a new future out of it.

Maybe pain started it,
But it's not what keeps me going.

What's your story?
What moment pushed you to take control?
And what are you choosing to create from now?

🖤

—
👋 Hi! I'm Dan Cumberland 🚀.

I'm building in public my path to 40k MRR as a creator and AI consultant.

I help founders authentically scale their voices and brands, without losing their souls.

You don't need the latest GPT.
You need better context and data.
That's the real secret.

Here's what I learned running my AI Mastery Cohort:

Michelle went from hoping "AI would go away" to writing custom code.

How?

No prompts.
Not the latest model.
Just better context and strategy.

Maggie turned a 90-page health assessment into executive summaries.

Daniel saw an opportunity and is vibe coding a whole business.

Even our biggest skeptic (erh, Raj) found gold.

The secret?

They all stopped obsessing over:
- Magic prompts
- Special commands
- Fear of falling behind
- Keeping up with all the models

Instead, they focused on:
- Organizing thier data
- Spending time on context
- Teaching AI what they need from it.

When everyone has the same AI:
- Prompt tricks = 10% edge
- Unique data = 10x edge

As Julie said: "I think differently now. What are my context documents? I didn't have that fundamental understanding before."

That's the real edge.
Stop chasing the latest update.
Start building your context.

🖤

Want to learn how? Cohort 02 starts soon.  
Find me in the comments.

—
👋 Hi! I'm Dan Cumberland 🚀.

I'm building in public my path to 40k MRR as a creator and AI consultant.

I help founders authentically scale their voices and brands, without losing their souls.

📸 : Last week was our "closing ceremonies" for cohort 01.  Here's half our cohort and a few guests crystalizing learnings and celebrating how far they've come.  Thanks to all of you (plus the many others off camera!)

He was hiring into burnout.

The fix wasn't more people.

It's like a case study on the scaling trap:
More clients = more work.
More work = need more people.
Need more people = costs explode, complexity multiplies.

Now you're managing instead of building the dream.
The very growth you wanted drains you.

Let's talk truth about that grind. 🖤

Here's the story:

I worked with a founder recently in my cohort.
He runs a valuation company.
Smart guy.  Great team.  Leaders in their field.

But they were drowning.

In what?
Data extraction and manipulation.
Buried under mountains of dense legal and financial docs, manually pulling tiny numbers.

Necessary? Absolutely.
Soul-crushing? Yes.

It wasn't just slow. 
It was burnout inducing.

So, what did we do?

We built a precision trained tool and AI workflow.

Think of it like a specialized digital assistant.
Trained for this specific task.

It reads the complex docs.
Pulls the exact data needed for valuations.
Structures it. Perfectly. Every single time.
Zero fatigue. Zero friction.

The result?

Yeah, reports got faster. That's the table stakes.
But the *real* magic? What actually matters?

- Consistency increased
- The team feels more free and fun. They're doing more actual analysis.
- They gained capacity. 

The ability to take on more core work *without* immediately needing to hire more people for that specific grind.

THIS is operational leverage.
THIS is reclaiming time and sanity.
THIS is building a business you actually love, sustainably.

This isn't about replacing your best people.
It's about freeing them.

I teach founders, leaders, and consultants exactly this: practical AI implementation for real leverage. It's what we cover in my AI Mastery Cohort.

DM me "Cohort" for the details. Let's build smarter, not just harder.

🖤

AI doesn't kill authenticity. (But it could.)

I just checked my analytics.

My email list? Up 1,000 subs in the past 30ish day
LinkedIn following? Growing at 10+ a day
Website traffic? Doubled since February 🚀

But here's the wild part:
AI wrote most of it.

But not in the way you think.

I use AI as part of a content system.
I use it to think laterally.
I use it to move from concept to draft.
I use it to take the friction out of my process.

And it's working.

And people keep telling me:
"Your content feels is so authentic"
"This resonates so much with me"
"Thanks for the vulnerability"

The secret?

I taught AI to understand my voice.
And I use it to accelerate my process.
And increase the surface area of my content.

Most people use AI wrong.
They let it write generic content that sounds like everyone else.
That's why their growth is flat.

But when you use AI right?
It's like having a team of writers and editors trained on you.

Then your message reaches further.
Then your impact grows deeper.
Then your audience builds faster.

Next week I'm going through it all.

Next week, I'm hosting a free training:
"How to 10x Your Reach with Authentic AI Content"

I've literally done that (see the screenshots)
And I'll show you how.

I'll walk through:
- How I train AI to write in my voice
- My complete content workflow
- The tools and prompts I use
- Real examples of what works (and what doesn't)

But this isn't just about a training.

It's about something bigger:

When you stay true to your voice,
And use AI to amplify it,
Magic happens.

Your message finds its people.
Your business grows.
And you stay you.

The registration link is in my bio.

If you've ever felt restless and unsure.

Read this.

You were told to build.
An empire. A legacy. A career.

The path: more hustle.
More wins. More everything.
Stack it up! Achievements are the bricks.

Maybe you really crushed it:
Teams. Exits. Titles. Toys.

But the fire fades.
Ambition flickers.
A quiet dread enters.

Is this it? Is this everything?!?

The instinct is to double down.
Panic. Fight the fading.
Prove we're relevant.

Stop.

That fading ambition? That still small voice?
It's supposed to be there.
It's not a bug. It's a feature.

It's telling you: the building phase did what you needed it to.
You climbed a mountain.
You proved you could do it.

But now is different.
This isn't failure.
This is something new.

This isn't a crisis shutting you down.
It's a calling breaking you open.

Shifting from external validation to deeper meaning.
From proving your worth to discovering it.

The emptiness isn't a void. It's space.

S. P. A. C. E.

Space for the real work.

If any of this resonates.
There's only one path forward:
Don't fight it. Listen. Deeply.

This isn't the end.
It's the beginning.
It isn't a crisis.
It's a calling.

—
👋 Hi! I'm Dan Cumberland 🚀.

I'm building in public my path to 40k MRR as a creator and AI consultant.

I help founders authentically scale their voices and brands with AI, without loosing their souls.

👉 Why do I post stuff like this? 
Because I need the reminder. 
And someone else might too 🖤

The Levels of AI Mastery

Most people get stuck at #3

Level 1: You're not having it.
You're still worried about AI taking your job.

Level 2: You start to play with it.
You're using basic prompts and getting decent results.
You're using it for basic search and simple tasks.

Level 3: You're all over it.
Every task becomes an opportunity for AI enhancement.
You're learning & growing & can't get enough.

Level 4: It's just another part of the tool stack.
You've integrated it so deeply, it's just another tool – like your smartphone or email.

Level 5: You transcend it.
You stop thinking about "AI" and focus purely on outcomes.

Level 6: You orchestrate it.
You're conducting a symphony of AI tools & workflows that work together seamlessly.

Level 7: You innovate with it.
You're creating things that weren't possible before.

Most people get stuck at Level 3.

They never push through to the boring part (Level 4, where it becomes just another tool).
And that's where the real magic begins.

🖤

What level are you at? What's keeping you from taking the next step?

Generic AI prompts are dying.

Specific ones are pure gold.

Alex Lieberman just pitched "Stack Overflow for AI Prompts" as an 8-figure business.

Great pitch.
Wrong product.

(Stack Overflow is like Quora for devs:
Ask questions.  Share answers.  Upvote responses)

Here's why it would fail:

Stack Overflow works because:
print("Hello World") = print("Hello World")

But AI prompts don't work like that.

"Write me a cold email" ≠ "Write me a cold email"

The same prompt gets you wildly different results based on:
- Your voice
- Your market
- Your product
- Your customer
- Your EVERYTHING

It's like building a script library for tinder chats.
It might do something.
But not what you want it to 😬

Alex says 91M daily AI users need this.
But what they actually need is fundamentally different.

Here's what I we have to start understanding:

👉 The "perfect prompt" is a myth.

The real magic is in your approach.
It's understanding how to work with AI on and in YOUR specific business.

It's not sexy.
But it's incredibly powerful.

This is what we actually teach in my AI cohort.

No "magic prompts" 🦄 🌈
No copy-paste solutions.
Just real, business-changing systems.

In the comments: do you have any magic prompts?  I'd love to hear what makes them so special.

ALSO:
We're going live today with the first cohort to Show-and-Tell what they've been building.

Let me know if you want an invite.
Or if you want more info.


—
👋 Hi! I'm Dan Cumberland 🚀.

I'm building in public my path to 40k MRR as a creator and AI consultant.

I help founders authentically scale their voices and brands, without losing their souls.

P.S. Alex is 100% great.  I have a ton of respect for him.  I'd love to build something in this space with him if anyone has an in!

Bill Murray nailed it.

Someone asked what he did for a living.

His reply?
"I have fun."

Simple. Profound.

Most folks chase happiness.
Like it's a destination you finally arrive at.
Something over the next hill.
Etherial. Fleeting.

Murray chased presence.
Being right here. Right now. Always.
Collecting moments that felt *real*. Undiluted.

And maybe THAT is what meaning actually is.

Not some grand, complex strategy.
No perfectly optimized life plan.
No ikaigi (insert eye roll here)

Just emotion to remember.
That changes you.
The feelings.
Of a moment, fully lived.
The texture of being present.

(can't you almost taste that sentence?)

In our rush to build, to scale, to achieve, to stay ahead, to win.
Do you remember to collect those moments?
Or are you just checking boxes?

There's always something that pulls us away.
The endless tasks list. The admin.
The stuff that drains our soul.

But what if AI could handle that?
At least some of it?
Not to replace us.
Or our humanity,
To reclaim it.

Freeing us up for the presence work.
The juicy stuff only we can do.
The stuff that feels real.

I don't mind if you don't share my energy for AI.
But I hope you share my enthusiasm for human beings.
Fully alive. Making change. Making art. The real big magic kind.

Learning to use AI in this way,
As a tool for presence, for meaning, for getting back to your unique fire.
This is what we do in my AI Mastery Cohort.
This is what I do for you in my one-on-one engagements.

We build systems that automate the routine,
that free you from the mundane
so you can focus on the *real*,
the memorable stuff,
the meaningful.

Presence isn't passive.
It's the active choice to engage.
I hope you'll choose it today.
Go do it.  Do it fun. 
(Like Murray.)

"I've tried 14 different AI tools and nothing sticks," she sighed.

Today, 1 custom system handles what those 14 tools couldn't. 

The difference wasn't the tech...
It was the approach.

I see this all the time.
Leaders collecting AI tools like Pokemon:
"Gotta catch em all!"

It's 2025's shiny object syndrome:
Maybe the next one will end the chaos?

But here's what most don't get:
The path to leverage isn't about more tools.
It's about systems that match your business needs.

I watched this founder transform:

Before:
- Juggling multiple AI subscriptions
- Scattered workflows across platforms
- Hours spent experimenting with new interfaces
- Few consistent results

We stripped everything back.
We built one custom AI workflow.
We designed a thoughtful AI strategy.

It all aligned with her exact needs.

Now?

- Single system running smoothly
- Clear, documented processes
- 80% reduction in manual tasks
- Using and benefiting from AI daily
(and having so much fun doing it!)

The shift wasn't just in simplicity.
It was in her confidence.
Her focus.

Her ability to build on success instead of constantly starting over.
This is what strategic AI adoption looks like.
Not chasing every shiny tool.
But building systems that truly serve your vision. 🖤

What could you accomplish with one AI system that actually works? 

--
PS - If you're ready to move from tool overwhelm to strategic ownership, I'm taking applications for my next round of the AI Mastery Cohort.

It's a 90-day transformation where you'll build AI systems uniquely aligned with your business, your voice, and your vision.

DM me "FREEDOM" for details.

"I don't have time for AI" - Founders

But here's what I'm seeing in my AI Mastery program:

Members are saving 10+ hours per week.

Here are 5 real examples (some details changed for privacy):

1. Valuation Firm CEO was drowning in documents
- Now: AI extracts financial data from complex legal docs straight into their valuation models
- Time saved: 6-7 hours per valuation
- Bonus: Eliminated need to hire 2 new analysts (saving hundreds of thousands)

2. Ecom Owner's Google Ads were a mess
- Now: AI analyzes performance data and recommends optimizations
- Time saved: 3 hours/week
- Bonus: Better ROAS (Return on Ad Spend) - saving thousands a month on an ads analyst and increasing revenue

3. COO created project timelines, trackers, and knowledge bases for team
- Now: AI generates first drafts based on proven frameworks
- Time saved: 2-3 hours/week
- Bonus: More consistent planning, less friction, more team capacity

4. CEO needed company-wide AI access
- Now: Custom Slack bot gives everyone AI power
- Time saved: 1-2 hours per person/week
- Bonus: No expensive per-seat costs (saving hundreds of dollars a month)

5. Fractional Operations Consultant transformed her clients' content
- Now: AI helps draft social posts matching each client's voice
- Time saved: 2-3 hours per client/week
- Bonus: Saved clients $3,000/month in copywriter fees

And there are so many more!

The pattern?

Start small.
Pick one painful process
Let AI handle the heavy lifting.

Here's what's wild:

None of these required coding skills.
None needed expensive custom solutions.
All were built using accessible tools.

The real impact?
- A valuation firm eliminated $140,000 in hiring costs
- An ecom brand cut ad spend and ditched ad management team
- Multiple founders saved 10+ hours every week
- One consultant saved her clients $36,000 annually.

But here's the truth:
The technology wasn't the hard part.

These founders all had something else:
A framework for turning AI from a toy into a real business tool.

They were all members of my AI Mastery Cohort.

And on May 7th, I'm starting the next one.

Want to build systems like these in your business?
Let me know below.  I'd love to chat with you about it.

Space is limited. The last cohort sold out.

Your greatest work is waiting.

I loved this conversation almost as much as I love turning people into muppets.

Listen in for real talk on AI, meaning, and making things that matter 🖤

Owner & CEO | Leveraging Portfolios to Change the World

View Tim Meisenheimer, CFA, CFP®’s profile

The episode is real.

The AI-generated Muppet & Pixar smiles? …not so much. 😄🎬

Excited to share our new Wealth Beyond Riches interview with Dan Cumberland 🚀 is live on YouTube. We dive into calling, career transitions, AI, and what meaningful work actually looks like.

🎥 Now live on YouTube → https://lnkd.in/eSDaqaK5

#WealthBeyondRiches #DanCumberland #MeaningfulWork #AI #Purpose #PixarButMakeItVocational

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