I Grow & Monetise Podcasts | CEO & Founder of Voics | Podcast Host at Kickoff Sessions

Most people think scaling to $1M+ is about posting more, working harder, or hiring faster.

It isn’t.

It’s about installing a simple, repeatable Ecosystem:

• One painkiller offer
• One content engine that attracts buyers
• One sales system that scales without more work

At Voics, we help coaches and agency owners grow from $20K to $100K/month and beyond by building this exact system.

No spreadsheets.
No duct-taped tools.

Just a clear business and predictable sales.

The Ecosystem breaks down into three things:

Offer – Build something painful enough to sell easily
Content – Create assets that generate leads, not likes
Sales – Run a simple system that closes consistently

To date, we’ve helped 500+ coaches and agencies generate $30M+ in client revenue.

I’m also the founder of Aura, an AI-driven sales platform built to run this entire system in one place.

If you’re serious about scaling sales properly, you’re in the right room.

Darren Lee

In 2018, I failed at dropshipping.

In 2019, I failed to build a startup.

In 2020, I worked a soul-destroying 9–5.

In 2021, I created content that got no views.

In 2022, I was laughed out of a tech company.

In 2023, I bombed more sales calls than I’d like to admit.

In 2024, I grew Voics to hundreds of active clients.

In 2025, I scaled Voics to multiple seven figures & launched Aura.

In 2026, I'm scaling Voics to $1M/month and Aura to $1M ARR.

In the beginning, nothing makes sense.

In the end, everything makes sense.

If you feel lost right now…

Keep chewing glass.

Brighter days are coming.

I used a FAKE name to buy my friend’s coaching program…

My friend wanted to launch a coaching business.

He was terrified of what others would think of him.

What would his friends think?
What about his family?

He thought no one believed in him… but I did.

So that day, I created a fake email and a fake name…

And I bought his program.

(Paid in full, like all great friends do)

What happened next was wild…

After I bought it, he had the confidence to sell it.

Then scale it.

Now he runs a super successful coaching business.

To this day, he has NO IDEA I bought it lol.

The truth is this:

Everyone just needs ONE person to believe in them.

With that belief, anything is possible.

The rest is history.

I started my career like most people.

College degree. No real direction.

Out every weekend.

No idea what I actually wanted to do.

But deep down, I knew I wanted to achieve more.

By 23, I had already started and failed multiple businesses.

All of them went to zero.

Until I found content. That changed everything: 

1. Signed my first few clients

2. Built a simple offer around what I knew (content)

3. Doubled down on offers, content and sales 

From there, it snowballed:

Started managing some of the biggest YouTubers in the world.

Ran their businesses (sales, marketing, ops).

Scaled their backend.

Saw exactly how they grew, from the inside.

Scaled Voics into a media company, made my first $1M online. 

Then I started showing others how to do the same.

Fast forward to now:

- We’ve helped 600+ coaches / agency owners scale their online business

- Built a multi 7-figure company (profit)

- Launched a 6 figure software company 

- Spoken on stages around the world

And we’re just getting started.

This is the power of content.

This is what happens when you stop playing small and go for it.

At 19, I worked at Skechers.

At 29, I own a multi–7 figure business.

Back then, I worked two jobs to get through university.

Skechers by day, Apache Pizza (IYKYK) or some random job by night.

I hated working for other people.

(I was the worst employee lol)

So I built my own job.

Today, my business runs on three core pillars:

1. The Problem

In 2021, I started making content for founders.

Helping entrepreneurs make money with content. 

That agency still runs today 

(Growing more than ever actually thanks to my amazing team).

Now we’ve scaled into a media company and education business.

2. The Traffic Source 

Content is the reason everything worked.

Building online opened thousands of doors.

I just had to run through them as a delusional kid.

3. The Sales Process 

No formal training. Just 1,000+ calls.

Most failed. Many fell on my face. Some hit.

I listened, adjusted, and got better.

That system has now helped 500+ entrepreneurs scale using content, offers, and sales.

If a guy who started in Skechers selling kids shoes can do it, you can too.

-
P.S. What was the worst job you had that set you up for life afterwards?

Made it to 30 with a house full of love, calendar full of sales calls and a head full of hair🖤

I just hosted the largest mastermind in Bali.

Helping 40+ entrepreneurs scale to 7 and 8 figures in revenue.

But my first mastermind was in my kitchen…

Only a year ago.

Progress isn’t based on years of experience.

Progress is based on getting shit done as fast as humanly possible.

I went from running events in my little kitchen to renting out the Ritz-Carlton for $100,000.

How? SPEED.

Many of our clients have also hit their first $50K/month, $100K/month, and even…

$1M/month following the exact same principle.

If you want to get shit done, focus on getting the work done.

P.S. 
Want to attend our 5th mastermind with over 50 entrepreneurs in September?

Comment “Mastermind” and I’ll get you set up right away.

I just released a FREE 2-hour sales course.

It shows you how to:

- Book more calls
- Close more calls
- Fix a broken sales process
- Turn leads into revenue

Built specifically for coaches and agency owners.

Want the full training?

Comment “SALES” below.

Anyone who shuts down their coaching business is full of sh*t.

I know this because my business generated $500K/mo.

And the same guys who shut down their business are the same guys who preach:

“Work 2 hours a day.”
“I log off at 4pm every day.”
“I know something you don’t.”
"Sell from a Google doc."

It’s all virtue signalling and fake ‘unique mechanism’ marketing.

And honestly… it’s unethical.

Because they don’t live that life.

Here’s what I know to be true:

Building a business is tough.
Scaling is tough.
Hiring is tough.

Firing is even worse.

I will never tell you this is easy.

I chewed glass my entire 20s.
Blew up three businesses before 23.
Then became a liquid millionaire in my 20s.

This sh*t is hard.

But if you do the right things, for long enough, it works.

So don’t quit your business like all the guys who “found themselves” and started padel instead.

Chew glass.

Getting married in my 20s made me millions.

Before that, I was -$10,000 in debt, stuck in a dead end corporate hellhole.

I may as well have signed the papers to a lifetime of mediocrity.

But here’s how it changed everything:

(And created a multiple seven figure business [profit] in my 20s)

Getting married in my 20s...

The biggest lie you’ve been told online:

You have to struggle for years before it starts working.

Bullsh*t.

You can skip the 3 hardest years of trial and error by simply learning the right skills.

In 2026 isn’t about “waiting your turn.”

It’s about mastering 3 core skills:

1. Sales & Psychology

Learn how to sell, speak like a human, and close.

2. Offer Building

Solve a painful problem for a specific person. One offer is all you need.

3. Marketing (Content)

Organic or paid but you need a consistent traffic engine.

This is exactly how to go from $0 to $100K with nothing but skill.

Unpopular opinion:

It’s 100% acceptable to only create content for leads.

You started your business to become an entrepreneur.

Not to become a dancing monkey on TikTok.

You don’t need to be liked, you need to get leads.

(With your content and in life)

Here’s how you do it:

1. Solve a painful problem

Pick the largest TAM and nail one specific problem.

For Voics, we help coaches scale their revenue.

Problem: getting leads and closing clients.

2. Throttle volume

Content, at its core, does one clear job:

Show people you’re still alive.

That’s it.

Why?

Most people quit their business and vanish.

Time in the game, expressed through content, is an unfair advantage.

3. Show what you believe in

Info alone is a total waste of time in 2026.

Nuance is where the game is at.

I’m a strong believer in sales calls and building sales teams.

It’s a hill I’m willing to die on.

I even built a sales software around call funnels called Aura lol.

Rinse, repeat, and never give up.

How to get your next 10 clients without selling your soul:

(As an agency owner or online coach)

And… I used to make all these mistakes before building a $535K/month biz:

1. Positioning

You need to be the guy (or girl) in your niche.

What’s the one thing you can outshine everyone on?

Positioning isn’t thinking you’re better than everyone else.

It’s having belief and conviction in what you do.

That’s what makes you a category of one.

2. Offer Stacking

One funnel, one product and one offer is brutal to scale.

You’re constantly kicking people through a funnel.

Instead, pull them into your ecosystem with a series of offers.

This isn’t ‘more’ work, it’s more access to you.

People pay based on proximity and speed.

We help entrepreneurs make more money.

But how we help them is completely different.

- Some want us to do it for them
- Some want us to do it with them
- Some want to sit in my Bali villa and build it together

Everything is priced accordingly.

3. Simple Sales System

No one is coming to buy from you randomly.

I mean no one.

You have to go to them if you want to increase sales velocity.

For the past few years, I’ve been running lean sales teams.

The entire process, from content that generates leads to onboarding, gets smoother every month.

If you have a terrible sales process, your whole operation is cooked.

People must be able to enter your world and buy with ease.

Whatever gets you the result.

If you want the full Ecosystem Model we roll out for all our clients, comment ‘Course’ and I’ll personally send it to you.

Your next 10 clients aren’t far away.

How to sign high-ticket clients consistently:

Build a simple, scalable Ecosystem.

Right now, you’re pushing leads through a funnel.

Trying to out-market a terrible offer.
Trying to out-sell bad marketing.

But the problem isn’t your effort.
It’s the lack of a scalable Ecosystem.

Do leads trust you?
Do they feel you’re the right solution?
Do they believe your solution will work for them?

You need to be able to answer YES to all three to sign clients.

On March 26th, I’m running a LIVE workshop helping coaches and agency owners sign high-ticket clients consistently.

If 2026 has felt hard as nails, there’s a better opportunity.

A simpler opportunity.

And I’ll show you exactly how to create your own Ecosystem to sign more clients.

Register here:
https://lnkd.in/g-q4Kip4

See you there.

I was literally afraid of sales calls…

Genuinely, I was afraid the prospect would show up.

And I’ve seen this trend repeatedly with entrepreneurs.

People say they “hate” sales, but they actually just fear it.

Once you know the small things you need to track,

It becomes repeatable, enjoyable, and scalable.

All you need is a simple system to track:

1. Total calls

Is your lead volume increasing or decreasing?

2. Show rate

Are prospects showing up willing to solve their issue?

3. Close rate

Are you attracting the right buyers into your world?

4. Total cash collected & revenue

How much money are you actually making on these calls?

Knowing these numbers allowed me to hit multiple seven figures a year at Voics.

Now, at Aura, you can manage all of your sales in one central spot.

No more spreadsheets managing spreadsheets.

Simple and effective.

Unpopular opinion:

A-Players show themselves in the first 24 hours.

B-Players b*tch, complain, and quit before shit gets good.

It’s better to hold back an A-Player by the reins.
Than to try to motivate a B-Player to get out of bed in the morning.

(And put their pants on the right way...)

As a founder, focus all your energy on finding your A-Players.

Develop talent.
Invest in team coaching.
Call them at 5pm on a Saturday.
Buy them lunch and dinner occasionally.

Do whatever you can to acquire and retain talent.

Because 1 A-Player is worth 100 B-Players.

Trust me.

Unpopular ways I scaled my business to multiple 7 figures:

1. Moved to 100% in-office 

Shit just gets done in person.

That’s it.

2. Went all in on paid media

Organic content has a ceiling.

I’d prefer my lead flow not to be based on an editor’s feelings that day. 

I spent 6 straight months locked away learning ads.

Paid off (literally).

3. Built a large sales team 

I tripled the sales team and fired all B-players. 

I only hire 3+ years of sales experience now.

Voics interviews up to 50 people a month now.

4. Spread my focus

Voics is a media company (content agency and sales agency) and consultancy.

As well as adding Aura to the mix (sales AI software).

5. Build a leadership team

My COO runs all operations across every product.

My Chief Education Officer runs all consulting.

Everyone does their own shit.

6. Split the teams up

I broke our total company (20+ team members) into a series of ‘pods’.

This ensures we don’t mess with each other’s stuff.

Do your stuff at an excellent level.

Don’t ask the sales team about your thumbnails.

Here are the results:

250+ new high-ticket clients.

7 figures in straight profit.

Became a liquid millionaire in my 20s.

My ‘secret’ is simple:

Chew glass. 

Don’t whine.

Keep going.

Most digital entrepreneurs think they need:

- better content
- more offers
- more sales calls

But here’s the uncomfortable truth...

Your content might actually be pushing clients away.

Not because it’s bad.

Because it’s incomplete.

Every buyer must internally say three yeses before they buy anything.

1. Logical Yes
“Can this person actually help me?”

2. Emotional Yes
“Do I trust this person?”

3. Value Yes
“Do I like how they solve the problem?”

Miss one…

Sales calls don't close.

Miss two…

You get ghosted (the uncomfortable truth).

Most entrepreneurs accidentally build their content around only one yes.

Authority content - Logical yes only
Personal content - Emotional yes only
Sales content - Value yes only

So prospects receive mixed signals.

They like you.

But they aren’t convinced.

Or they believe you…

But they don’t feel connected.

Or they trust you…

But they don’t like your method.

So they hesitate.

And hesitation kills deals.

The businesses signing high-ticket clients consistently structure everything around generating all three yeses simultaneously.

At 30 years old, I run a consulting firm and a tech company.

But at 23…

I had three failed businesses.

I failed at events.
I failed in ecommerce.
I failed in software.

Then, in 2020, I slowed down.

It was time to listen and learn…

And I started creating content.

That’s when things snowballed.

I began consulting some of the largest brands and entrepreneurs on their content.

That’s how my company Voics was born.

What started as a simple agency…

Turned into a media company and education business.

We hit 50 clients.
Then 100.

Today…

Voics has helped 500+ coaches and agency owners scale their businesses.

Many to $1M per year.
Some to $1M per month.

Here’s how we do it…

Through a system Voics created called The Ecosystem.

It’s a framework designed to help businesses:

- Create offers
- Attract leads
- Close more clients

My mission is pretty simple:

Make business scalable, repeatable, and enjoyable.

As a result…

More coaches and agency owners are hitting record months than ever.

Today Voics generates $535,000/month with multiple seven figures in annual profit.

But I noticed something…

Even successful entrepreneurs struggle with sales.

Booking qualified leads.
Tracking numbers and reports.
Improving their sales calls.

Most businesses are duct taped together with Zapier.

And that’s why many never reach $1M/year or $1M/month.

So I built the solution.

My software company, Aura.

Aura helps entrepreneurs and sales teams:

- Book qualified calls
- Track performance
- Improve close rates

All in one platform.

Now Voics and Aura work together to help entrepreneurs scale.

If you want to see how this works…

I created a three-hour free course that breaks down the entire system.

How to scale your coaching business using the Ecosystem Model.

Comment “COURSE” and I’ll send it to you.

If you want to know the actual secret to scaling your business…

It’s not some magical funnel.

It’s this: scale your care.

That’s the real game.

Because most online business owners don’t actually care enough.

Not about the client.
Not about the result.
Not about what happens after the payment clears.

So what happens?

They sign clients.
They get paid.
Maybe even paid in full.

But the clients don’t stay.

They don’t get the result they really wanted.
They don’t feel understood.
They don’t feel deeply seen.

And eventually they leave.

After making $500K+ per month and working with hundreds of clients...

The difference between the people who stay small and the people who build something real is painfully obvious:

The ones who win actually give a f*ck.

They know their clients.
They understand the business.
They understand the pain.
They understand the actual desire underneath the surface-level goal.

That’s what allows someone to trust you.
That’s what allows someone to open up.
That’s what allows someone to stay.
And that’s what allows your business to compound.

Because the truth is…

If you don’t care about the result, you won’t get the result.

And if you want to make more money, you need to solve deeper problems for people.

That starts with understanding why you’re building in the first place.

If this hits home, watch the video below.

This is one of the most important pieces I’ve recorded in a long time.

Here’s the simplest path to $100K/mo:

The right product.
A working traffic source.
And a simple sales process.

I recorded a 46-minute masterclass with William Brown on scaling the right way to $100K/mo.

This is EVERYTHING you need to break out of the $30K/mo jail…

And build the easy path to $100K/mo.

We went back and forth on sales teams, ads, and multiple offers.

So you don’t have to.

Watch it here: https://linktw.in/wpgVuf

WHAT I DO NOW

I'm a Partner at Aragon Holdings, where I lead M&A — sourcing, evaluating, and acquiring profitable, founder-led agencies in the $500K–$3M revenue range.

We're not financial sponsors chasing quick exits. We acquire agencies to own and operate them over the long term, partnering with founders who want liquidity, reduced risk, or a path to succession without dismantling what they've built.

Every deal is structured around founder goals — full exit, partial liquidity, equity rollover, or operating partnership. I work directly with founders from first conversation through close.

WHAT I'VE BUILT

I'm also Co-Founder of Marketers in Demand, the operating platform behind Aragon's portfolio of B2B marketing agencies. That portfolio now includes a collection of agencies focused on helping small marketing teams at technology companies do more with less.

Before that, I co-founded 522 Productions and scaled it to the Inc. 500 before exiting. My early career was in consulting at Oracle, IBM, and PwC. I hold an MBA from the University of Georgia.

I'm a 3x Inc. 5000 agency owner and operator. 

IF YOU'RE AN AGENCY FOUNDER

If you're running a profitable agency and thinking about what's next — whether that's growth, partnership, or an eventual exit — I'm always open to a confidential conversation. No pressure, no pitch. Just a real discussion about whether there's a fit.

Hit me up here on LinkedIn or send a note to tristan.pelligrino@aragon-holdings.com

Tristan Pelligrino

If your agency does $500K–$2M in revenue, you're probably not getting a big check at closing.

I know that's not what the LinkedIn gurus selling "exit planning" courses want you to hear.

But here's the reality from someone who's been on both sides of these deals:

Buyers with real capital—the ones who could write a seven-figure check at close—aren't focused on smaller agencies. The risk profile doesn't make sense for them.

I've seen it happen:

→ Founder-led sales that disappear when the founder does
→ Two-person delivery teams where one resignation creates a crisis
→ Client relationships that exist in someone's head, not in systems
→ Revenue concentration that makes the whole thing fragile

These aren't dealbreakers. But they do change the math.

A buyer putting up significant cash upfront needs to de-risk that investment. At $500K–$2M in revenue, the operational vulnerabilities are just too high to justify loading cash at the front end.

So what actually works at this level?

Stop optimizing for maximum cash at close.

Start optimizing for the right partner.

The founders I've seen get the best outcomes from smaller agency exits weren't chasing the biggest number. They were looking for buyers who would:

→ Invest in growth instead of just extracting value
→ Structure deals where founder upside continues post-close
→ Bring operational resources that reduce the risks buyers worry about
→ Treat the transition as a partnership, not a transaction

Here's the rule I use when talking to founders in this range: If someone's promising you a big upfront payout for a sub-$2M agency with no earnout or rollover, ask harder questions. The math usually doesn't work—which means either the terms will shift, or the buyer doesn't understand what they're buying.

The better approach:

Find a partner who sees your agency's potential and structures a deal around growing together.

The real payday for smaller agencies usually comes after the close.

The hardest part of running an agency right now isn't finding talent. It's building a team that keeps up with how fast everything moves.

In the last two weeks alone:

→ Perplexity launched its "computer" product
→ OpenAI acquired OpenClaw
→ Claude rolled out cross-platform CoWork (both Mac and Windows)
→ Google dropped new Gemini capabilities and a bunch of other products (they do a bad job marketing their stuff)

That's one cycle. There will be another next week. And another after that.

Most agency owners I talk to feel this pressure but haven't changed how they hire or how they build culture around it.

They're still screening for skills that existed 18 months ago. They're still assuming training programs alone will close the gap.

Here's what I've learned: You can teach tools, but you can't train curiosity.

The people who thrive in this environment aren't waiting for a lunch-and-learn. They're testing new tools in the evening or on a weekend because they can't help themselves. 

They're reading release notes for fun. They're building workflows just to see what's possible.

This isn't about expecting unpaid work. And it's not a knock on anyone doing solid work today. It's about recognizing that the gap between "keeping up" and "falling behind" is now measured in weeks, not years. And that's an environment thing as much as it's a people thing.

As a leader, that means two things:

First, create an environment where curiosity is rewarded, not just productivity. Give people time and space to experiment. Make it safe to test things that don't work.

Second, hire for it intentionally. Here's what I look for now:

→ Do they have a personal project where they're experimenting with new tools & technology?
→ Can they tell me about something they tested recently that didn't work?
→ Are they naturally pulled toward learning about this space?

The agencies that win the next few years will be the ones that built teams of learners, not just executors.

I've said it before, the best marketers I know are the ones who are the most curious.

Partner @ Aragon Holdings | Acquiring Founder-Led Agencies | 3x Inc. 5000 Entrepreneur | Co-Founder @ Marketers in Demand

The line between software company and agency is blurring. And most agency owners aren't really paying attention.

For 20 years, the model was clear:

→ Software companies sold tools
→ Agencies sold services to use those tools
→ Clients paid both and hoped the outcomes followed

What's emerging is something different. 

It's something discussed more heavily on X and in some communities I'm in → Software Enabled Agencies.

Old model: "Here's a seat license. Here's a retainer. Good luck."

New model: "Here's the outcome. We own the delivery. Pay for results."

I've seen the shift firsthand:

An agency used to charge $8K/month for paid media management. Separate from that, the client paid $2K/month for reporting tools, $500/month for project management software, and $1K/month for creative collaboration platforms.

Four invoices. Zero accountability alignment.

Now? Agencies are bundling the software into the service. They're not reselling tools—they're building proprietary systems that make their delivery faster, more transparent, and harder to replicate.

In some cases, this requires custom internal software/tools. In others, it requires building on top of existing platforms.

The client pays for one thing: the outcome.

Here's what I think actually matters:

The agencies that win in the next 4-5 years won't be the ones with the best talent OR the best tech stack.

They'll be the ones who take the most accountability for results.

When you own the outcome end-to-end—strategy, execution, reporting, optimization—you capture value that used to leak out to five different vendors.

Across our agencies, we're building toward this. Custom dashboards clients can't get elsewhere. Automated workflows that eliminate handoff delays. AI-assisted delivery that lets us do in hours what used to take days.

Not to cut costs. To own more of the value chain.

Here's the rule I use: If a software tool is critical to your delivery, you should either build it, white-label it, or integrate it so deeply that clients see it as YOUR capability—not a third-party dependency.

Software and services are converging. That's just where things are headed.

Agencies that figure this out will command premium pricing and sticky client relationships.

Agencies that don't will keep competing on hourly rates while software eats their margins from both sides.

Running a video production agency for over a decade was the hardest thing I've done as an operator. I wouldn't recommend it. But I'd do it again.

Here's the thing about video production: nothing is repeatable.

Every project is a custom build. Different crews. Different locations. Different timelines. Different client stakeholders with different schedules.

Then add the variables you can't control:

→ Weather pushes your shoot by three days
→ The CEO's calendar shifts and now your entire production schedule is blown
→ The location you scouted falls through 48 hours before call time
→ Equipment fails on set with 30 people standing around billing hourly

You're not running an agency. You're running a logistics company that also happens to make creative work.

I've seen agency owners in other verticals stress about a delayed client approval or a missed deadline. And I get it, those things matter.

But when you've had to reschedule/reroute a 15-person crew because of a blizzard, your definition of "problem" gets recalibrated.

Here's what a decade of video production actually taught me:

→ Contingency planning isn't optional—it's the job
→ Systems thinking matters more than talent
→ You can't scale chaos, so you build processes that absorb it
→ Client communication under pressure is a skill you develop or you fail

Would I recommend running a 100% project-based video production company? No.

The margins are brutal. The stress is constant. The unpredictability never stops.

But if you want a masterclass in agency operations, project management, and staying calm when everything breaks? There's no better training ground.

I don't run a company that shoots large television commercials anymore. Our teams don't travel like they used to.

But every system I've built, every contingency I plan for, every client fire drill I handle...it all traces back to those years of solving impossible problems on set.

We just shipped something I'm really excited about.

We built an AI-powered chat layer into our content operations platform that lets you have a conversation with your entire content library.

Not a keyword search. Not a filter. An actual conversation.

Ask it "What topics do we write about most?" and it queries your structured content data (categories, publish dates, custom attributes) and gives you a real breakdown. 

Ask it "What's our perspective on ABM?" and it searches semantically across every blog post, article, and document you've ever published to synthesize an answer grounded in your actual words.

You might be thinking "Google Drive has AI search now" or "Notion can do this." 

Here's why this is different:

Before you can ask smart questions, you need smart data. Our platform actually ingests your content. 

We pull in YouTube videos and transcribe them automatically. We read PDFs, parse web content, and break it all down into structured, searchable data. Then we automatically categorize and tag every piece based on your organization's custom content taxonomy. Not generic labels. Your categories, your attributes, your content structure.

That ingestion layer is what makes everything else possible. You're not searching filenames or skimming document headers. You're querying thousands of content chunks that have been broken down, embedded, and organized before you ever ask your first question.

The part I'm most proud of is the routing layer. Every question gets classified in real-time and the system decides the best way to answer it:

• Aggregate questions (counts, trends, timelines) hit your structured database directly
• Content questions (themes, strategies, perspectives) use vector similarity search across your embedded content library
• Complex questions use both

This matters because not every question should be answered the same way. "How many posts did we publish last quarter?" is a database query. 

"What unique angle do we bring to demand gen content?" requires reading everything you've ever written.

This wasn't a weekend project. It was weeks of building the ingestion pipeline, embedding infrastructure, chunking strategy, and retrieval tuning to get answers that actually reflect what's in the library. Not hallucinated summaries.

The vision: every piece of content your team creates becomes searchable institutional knowledge. Not buried in a Google Drive folder. Not lost in a CMS. Available in a conversation.

We have so much more on the product roadmap, excited to keep rolling things out to clients.

Most marketing teams organize content by format. Blog posts in one folder. Videos in another. Social in a spreadsheet somewhere.

Then six months in, someone asks: "What content do we have for enterprise buyers in the consideration stage?" And nobody can answer without digging through 200 files.

We hit this wall with our clients enough times that we rebuilt how we think about content organization from scratch. 

And the way we think about it doesn't start with technology or AI. It starts with structure.

Here's the framework we landed on:

Three layers. Each one answers a different question.

👉Content Types answer "what format is this?"

Blog post, case study, newsletter, video script. Straightforward. But this is where most teams stop — and it's the least useful layer for strategic decisions.

👉Categories answer "what do we want to be known for?"

These are your content pillars — the topics and themes that define your brand's authority. They're the strategic bets you're making about how your market should perceive you. Every piece of content should reinforce one of these pillars.

👉Custom Attributes answer "who is this for and where does it fit?"

Target ICP. Buying stage. Industry vertical. Product line. These are the fields unique to each client's business — the metadata that turns a content library into a searchable, filterable strategic asset.

Without all of these layers, you can't answer the questions that actually matter:

- "What do we have for mid-market buyers evaluating competitors?"
- "Where are the gaps in our consideration-stage content?"
- "Which ICP segments are we underserving?"

The other thing we did: we made AI categorize everything automatically on ingest. Every blog post, transcript, or uploaded document gets analyzed and tagged across all three layers without anyone manually filling out fields.

When you have no data integrity, then it doesn't really matter how many tools you build or workflows you roll out. You'll be working from bad data.

Content ops isn't about making more content. It's about knowing exactly what you have, what's working, and where the gaps are.

Sometimes agency founders wait too long to bring in outside help. Then they overcorrect and hire consultants for everything.

Both approaches cost you.

I talk to 5-10 agency owners a week, and this question comes up a lot: "Should I hire an advisor for this?"

There's no universal answer. But here's the framework I use after years of hiring (and sometimes wasting money on) external help:

Ask two questions:

1. Is this obstacle big enough to block a meaningful goal?
2. Can my team solve it fast enough to matter?

If the answer is yes to #1 and no to #2, bring in outside expertise.

That's it. That's the filter.

I've used external consultants for financing, messaging and positioning, software development, HR issues, and legal matters. Every single one accelerated something I couldn't have figured out quickly enough on my own.

The value isn't just expertise. It's perspective.

Your team is too close to the problem. They have context, but they also have blind spots. A good advisor sees patterns across dozens of similar situations. They know where the landmines are because they've watched other people step on them.

Here's what actually matters when evaluating whether to hire help:

→ Speed: Will this person get you to a solution 3-6 months faster than figuring it out internally?
→ Stakes: If you get this wrong, what's the cost? High stakes = outside perspective is worth it.
→ Repetition: Is this a one-time problem or something you'll face again? If it's recurring, build the capability internally. If it's a one-time obstacle, rent the expertise.

The mistake I see most often: owners treat advisor spend as a cost instead of a trade.

You're not paying $10K for advice. You're trading $10K for 4 months of time you would've spent stuck.

The agencies that scale aren't the ones who figure everything out themselves. They're the ones who know when their own expertise isn't enough—and move fast to fill the gap.

Your best client is about to churn. The KPIs look great. You have no idea.

That's the problem with gut feel at scale.

Managing a handful of accounts, you can sense when something's off. Managing 75+? You need data for that. Both quantitative and qualitative.

I've operated various agencies with 10, 15 and even 30 engagements or projects going on at one time.

When running 15-20 accounts, we could stay close to every client. You pick up on tone shifts in meetings. You notice when someone stops responding to Slack as quickly. You just know.

That doesn't scale.

Once we crossed 75 accounts across our portfolio, we had to evolve how we track client health. KPIs and deliverables weren't enough. That only tells you what happened, not how the client feels about it.

So we started tracking both.

Every client meeting gets transcribed and scored for sentiment — positive, neutral, or negative. Automatically. No one has to remember to flag anything. We built this into our internal application and use a custom prompt to score the sentiment.

Now we can see the full picture:

A client hitting every KPI but trending neutral in meetings? Something's brewing. A client behind on deliverables but consistently positive? The relationship is solid — they just need better execution.

The quantitative data tells us if we're delivering. The qualitative data tells us more about the relationship.

We pipe it all from Fireflies into our company's application. We can also add manual transcripts if something happens with a specific recording.

At scale, the agencies that retain clients aren't always the ones with the best results.

They're the ones paying attention — with data to back it up.

P.S. - We are far from perfect. But I'm proud of our team. We all do every damn thing we can to evolve and improve the way we deliver for clients.

A lot of service businesses (agencies especially) run on duct tape.

Spreadsheets for tracking. Tribal knowledge for strategy. Manual reports that take hours. Deliverables built from scratch every quarter.

We decided to build something different.

Over the past year, we've been developing/refining/improving an internal operating system purpose-built for how a modern agency actually works. It has two core pillars:

Pulse — The Portfolio Command Center

Pulse gives leadership real-time visibility into every active contract across the portfolio. We have a collection of four agencies, so this helps aggregate data. It connects ClickUp, QuickBooks, and HubSpot into a single view and introduces a consistent "currency" that tracks what's been sold, delivered, and owed — down to the task level.

The key metric: points burden. Based on an internal points system, this metric tells us instantly whether a contract is on-track or off-track relative to billing.

No more guessing. No more stale spreadsheets. Management reports generate automatically with 90 days of delivery velocity, financial position, and AI-analyzed meeting sentiment per contract.

Compass — The AI Strategy Workspace

Compass is where strategy actually lives. Every contract gets a structured workspace that captures meetings, notes, competitive research, and deliverables — all connected through a knowledge base that compounds over time.

The real unlock: AI-powered context to drive key decisions. Compass assembles context from a client's entire history — past roadmaps, meeting transcripts, competitive intelligence, the agency's process library. This helps us craft deliverables at a much faster rate, with greater detail. Research reports. Strategic roadmaps. Channel-specific plans. Each one builds on the last quarter's work rather than starting from scratch.

When a strategist leaves, the knowledge stays. When a new quarter begins, the strategy evolves rather than resets.

Why does this matter?

Agencies sell expertise and execution. But most of the infrastructure for managing that work is generic tooling held together by manual processes. Pulse and Compass are our answer to what an agency operating system should actually look like — one that treats delivery tracking and strategic intelligence as the main driver.

We're not selling it. We built it because we needed it. And it's changed how we operate.

P.S. - screenshot below of one of the dashboards (taken from a presentation I gave last week to a group of agency owners)

Most agency M&A conversations go nowhere. And that's the problem.

The agency acquisition space is flooded with people who love talking about deals but never close them.

I've seen it from both sides—as a seller and now as someone who acquires agencies as my full-time focus.

Here's what actually happens:

A buyer reaches out. They're "very interested." You have three calls. You send financials. They ask follow-up questions. You answer them. Then silence. Or worse—they come back with an offer that reveals they never had the capital or means to get a deal done to begin with.

Meanwhile, you've spent 6-8 weeks on someone who was never going to close.

On the flip side, sellers do this too. They'll entertain conversations for months, get deep into diligence, sign an LOI—then get cold feet or reveal deal-breaking terms they knew about from day one.

Here's the rule I use: Qualify before you invest.

Before any serious negotiation—definitely before signing an LOI—verify three things:

→ Do they have the financial capability to close this deal?
→ Have they actually completed a transaction before?
→ Are they operating on a real timeline, or just "exploring"?

If you can't get clear answers to those questions, you're not in a deal. You're in a conversation that's burning your time.

Because once you sign an LOI, you're spending real money. Legal fees. Accounting. Diligence. Your own hours.

And if it falls apart? Those costs don't come back. You're restarting from zero—back to marketing the business, fielding new inquiries, rebuilding momentum.

I've seen founders lose 6+ months and $30K+ on deals that were never real.

The better approach:

Treat qualification like a gate, not a formality.

Ask direct questions early. Request proof of funds/financing before deep diligence. Check references on past deals.

The serious buyers and sellers won't be offended. They'll respect it.

The tire kickers will disappear. And that's exactly the point.

Most agency owners check their bank balance and call it financial management.

Then they're blindsided when cash gets tight or margins erode.

I've acquired and operated multiple agencies. The ones with real financial clarity aren't running complex dashboards or hiring fractional CFOs on day one.

They're following a simple cadence.

Here's the rule I use:

Daily: 5 minutes. Check cash balance, AR/AP, billings, collections, and sales activity (calls booked, proposals out, deals closed). No fancy graphics. Just context.

Weekly: Same metrics, plus a 13-week rolling cash forecast. This single report has saved more agencies from crisis than any P&L review. Cash problems don't surprise you when you're looking 13 weeks ahead.

Monthly: 1-2 hours of actual analysis. Compare actuals against budget, forecast, and prior periods. Ask three questions:

→ Are we hitting profitability goals?
→ Are we hitting growth targets?
→ Are we converting revenue to cash efficiently?

If the answer is no, the reporting tells you where to dig. Is it overhead creep? Production inefficiency? Customer acquisition cost? Working capital getting stuck in AR?

Quarterly: Zoom out. Are the fundamental choices—pricing, service mix, cost structure, growth investments—still right? This is strategic, not operational.

The agencies that struggle financially aren't usually bad at delivery. They're flying blind on the numbers until it's too late to course correct.

Simple and consistent beats complex and sporadic every time.

If you're running an agency without a 13-week cash forecast, start there. It takes 30 minutes to build and 5 minutes to update weekly.

That one habit separates agencies that scale from agencies that scramble.

Earlier this year I built a cash flow projection tool almost entirely with AI. I want to walk through exactly how it came together, because I think this is the future of how operators build internal tools.
 
The stack: Next.js (App Router) for the frontend. Supabase for auth, database, and row-level security. Recharts for data visualization. Vercel for deployment. Claude Code as the AI coding partner.
 
What it does: The app pulls in actual bank balances, then lets you map revenue and expense line items to specific weeks across a 26-week projection window. It calculates running balances, consolidates across multiple agencies, and renders everything in an interactive weekly grid and area chart.
 
The scenario engine is where it gets interesting.
 
Instead of cloning entire datasets for each scenario, I built a foundation + overlay model. Your base case is the foundation. The single source of truth. Overlay scenarios layer adjustments on top (new hires, lost clients, delayed payments) without duplicating data.
 
Changes to the foundation automatically ripple through every overlay. Negative line items serve as the override mechanism. Want to model losing a $10K/month client? Add a -$10K revenue entry in the overlay.
 
The weekly grid is a spreadsheet-style interface with inline editing, copy/paste support, drag-and-drop row ordering, and configurable row groups. Foundation rows appear as frozen (read-only) in overlay scenarios, with editable adjustment rows below a clear divider.
 
The dashboard shows all scenarios simultaneously on a single chart. The selected scenario highlighted in purple, others in gray. You can visually compare the cash impact of different decisions at a glance.
 
My takeaway: The moat for operators isn't going to be whether you can afford custom software. It's whether you know what to build. Domain expertise + AI tooling is a seriously powerful combination right now.
 
The app has been running across our agencies for months now. Happy to share more about the architecture or methodology if anyone is building something similar.

Most agencies can't answer a simple question: What is a contract?

I've audited dozens of agencies for acquisition. And one of the most common gaps I find isn't missing contracts—it's that nobody agrees on what a contract actually is.

Some teams count every email approval as a contract.
Others only count signed MSAs.
Most land somewhere in between, inconsistently.

This matters more than you think.

When you can't define what a contract is, you can't track revenue accurately. You can't forecast. You can't prove what was sold versus what was delivered. And when it's time to sell your agency, buyers will find the mess.

I spent years working federal government contracts before agency life. Say what you want about bureaucracy, but the feds know how to structure a contract.

Here's how I think about it. Every contract needs three things:

→ A unique ID that lives in one system of record
→ An original statement of work that defines scope, deliverables, and terms
→ A clear modification trail that links any changes back to the original

*Note - this follows along closely with how I built federal financial systems with purchase orders (POs) and modifications (MODs).

That's it. No unique ID? It's not a contract, it's a conversation. No original SOW? You're guessing at scope. No modification tracking? You have no idea what you actually owe the client.

The agencies that run clean on this aren't just easier to acquire. They deliver better, forecast tighter, and have fewer client disputes.

Your team needs to be trained on this. Your strategists, your PMs, your account leads—everyone touching client work should know exactly what constitutes a contract and where to find it.

If you're a $1M+ agency without a contract management system, then this will probably come to bite you before too long.

Agencies stay on the wrong CRM or PM platform for years because they're afraid of switching costs.

I get it. You've got years of data in HubSpot or Pipedrive or some Frankenstein custom project management setup. The thought of migrating feels like open-heart surgery.

But here's what I've learned after acquiring multiple agencies and inheriting several different types of CRM/PM configurations: 

The switching costs you're worried about are mostly fictional.

The real problem isn't the technology. It's that you haven't defined your data independently of the platform. You haven't broken down your business into components which can be transferred to other systems (and explained logically to someone outside of the agency).

Instead, you've built business logic inside the tool instead of building a framework you could take anywhere.

Think about your CRM. It breaks down into a handful of core components:

→ Contacts (the people)
→ Accounts (the companies)
→ Activities (emails, calls, meetings)
→ Stages (where they are in your pipeline or journey or engagement level)

Your project management data is similarly simple:

→ Contracts (the agreement)
→ Service types (what you're delivering)
→ Plans (when you're delivering it)
→ Processes (how you deliver it)
→ Engagements (the active work, tasks and deliverables)

That's it. Everything else is implementation detail.

When you define these components abstractly, switching from HubSpot to Pipedrive becomes a mapping exercise, not a business disruption.

You can move freely from ClickUp to Asana or whatever.

We've done this several times. The agencies that had cleaner data models migrated in days. The ones that let their CRM become a junk drawer? Weeks of cleanup.

Here's the rule I use: If you can't explain your data structure on a whiteboard without mentioning a software name, you're locked in.

The agencies that will have the most flexibility in the next few years aren't the ones on the "best" platform. They're the ones who built platform-independent thinking into how they operate.

This gives you flexibility to change out LLM models, plugin different agents, and take advantage of new technology.

Your tools should serve your business. Not the other way around.

We built our own marketing intelligence API.

Across our agencies at Marketers in Demand, we kept running into the same problem: every client engagement required the same types of deep research, audits, and strategic planning. 

But the sequence and emphasis always varied based on the client's needs.

So we built Master Marketer.

It's an API that lets us send in a payload of information about a client and their competitors and get back structured, ready-to-use output. It assembles competitive research, compiles SEO audits, constructs draft 90-day roadmaps based on our own process library/task list, crafts draft content plans,   and more.

Here's what makes it powerful for us:

It's modular. Each function does one thing well. A research report pulls from LinkedIn, YouTube, Moz, SpyFu, DataForSEO, and other live data sources — then synthesizes everything through AI into a structured document. An SEO audit crawls the site, converts on-page content to markdown, analyzes keyword gaps, evaluates backlink profiles, and checks AI search engine visibility. Each output is its own building block.

It's composable. Outputs chain together. Research feeds into a roadmap. The roadmap and an SEO audit feed into a content plan. We decide the sequence based on what matters most for a given client. Same core functions, different configurations.

It's consistent. Whether we're serving a SaaS startup or an enterprise B2B company, the underlying intelligence gathering and analysis follows the same rigorous process. The inputs change. The quality doesn't.

It's ours. We're not locked into someone else's workflow or limited by a platform's assumptions about what matters. We built it around what we know drives results for our clients — and we can extend it whenever we identify a new need. We can also test different data providers and APIs, there's no vendor lock in with the types of data we assemble.

The simplest way to think about it: fill out a form or send a payload, get back marketing intelligence you can actually use. No black box. No generic templates. Just structured output built on real data, shaped by how we actually do the work.

When you own the system, you stop adapting to tools and start building tools that adapt to you.

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