Jesse Futia

Writer and Co-Founder @ CRE Digital | Copywriting & social media management for the world's most innovative real estate companies

Creating content on social media is digital leverage for real estate professionals. 

𝗪𝗶𝘁𝗵𝗼𝘂𝘁 𝗶𝘁, 𝘆𝗼𝘂 𝘄𝗼𝗻’𝘁 𝘀𝘂𝗿𝘃𝗶𝘃𝗲 𝘁𝗵𝗲 𝗻𝗲𝘅𝘁 𝗱𝗲𝗰𝗮𝗱𝗲. 

You now have two choices:

1. Create content

2. Be passed by those that do 

My story 👇

Broke college kid turned 7-figure real estate investor and writer. 

I help 7-figure real estate professionals grow their brands and drive qualified leads on LinkedIn. 

--

Hit the 🔔 and follow along each day for free tips.

Ready to grow your brand on LinkedIn to drive more qualified leads?

𝗛𝗶𝘁 𝘁𝗵𝗲 𝗹𝗶𝗻𝗸 𝗶𝗻 𝗺𝘆 𝗳𝗲𝗮𝘁𝘂𝗿𝗲𝗱 𝘀𝗲𝗰𝘁𝗶𝗼𝗻 𝘁𝗼 𝗮𝗽𝗽𝗹𝘆 𝘁𝗼 𝘄𝗼𝗿𝗸 𝘄𝗶𝘁𝗵 𝗺𝗲.

Chief Executive Officer

Helping busy professionals build generational wealth and retire comfortably through passively investing in real estate.

AI just gave real estate investors a 1 million word memory.

That's not a typo.

One conversation. One million words of context.

Here's what that means for your capital raise.

Upload every OM, every financial model, every LP email, and every market report into a single AI conversation.

Then ask it anything.

"What objections came up most across my last 50 LP calls?" Answered in 30 seconds.

"Build a custom pitch for an LP who invests in Phoenix multifamily with $2M liquid." Done in 2 minutes.

"Compare my last 3 deals side by side and write the investor update." Done before your coffee gets cold.

Before this update, AI held 150,000 words. Enough for a few documents. Not enough for a real operation.

Now it holds your entire deal room. Every data point. All cross-referenced instantly.

And the second shift is even bigger.

AI doesn't just answer questions anymore. It executes. Builds documents. Runs research. Multiple agents working in parallel on different tasks.

We went from "AI helps you think" to "AI does the job."

→ LP research: 4 hours → 12 minutes
→ Quarterly updates: all weekend → 15 minutes
→ Outreach personalization: impossible at scale → fully automated

Most real estate investors have no idea this happened.

DM me "update" and I'll show you how to set this up for your raise.

Systems and Operations Expert for CRE Professionals | $30M+ Raised | 60+ Operators | Co-Founder @ CRE Digital

I run a marketing agency. Here's why I'm telling you the truth about AI.

Most agencies won't tell you this. I will — because it's how we stay ahead.

An AI tool now does in 11 minutes what used to take a full team a week.

I know because I built the systems that proved it.

Here's what AI replaces tomorrow:

1. Social media content
One voice memo → 5 LinkedIn posts, a newsletter intro, and 3 email subject lines. Written in your voice. Not a template.

2. Investor outreach emails
Paste 10 LP profiles. Get 10 custom first-touch emails referencing their actual portfolio, recent deals, and investment thesis.

3. Market research briefs
Ask for a multifamily market update in Phoenix. Get a full brief with data, comps, and talking points in 4 minutes.

4. Quarterly investor updates
Upload your financials and property report. Full draft in 90 seconds. Your voice. Real numbers.

5. CRM follow-ups
Upload your contact list. AI scores every investor by engagement and writes a personalized follow-up for each one.

Here's what AI does NOT replace:

→ Relationships
→ Judgment on which deals to pursue
→ The handshake at closing
→ Trust built over years

The agencies that win are the ones building these tools into their clients' workflows. That's what we do at CRE Digital.

What's the first thing you'd automate? Drop it below.

Systems and Operations Expert for CRE Professionals | $50M+ Raised | 60+ Operators | Co-Founder @ CRE Digital

6 months ago I was burning out running a marketing agency with 8 clients.

Working 70-hour weeks. Writing every post manually. Sending every email one by one. Building every report from scratch.

I loved the work. I hated the ceiling.

Then I went all-in on Claude AI. Not as a gimmick. As infrastructure.

Here's what changed:

Month 1: Replaced my content writing process. 5 posts per client went from 6 hours to 45 minutes.

Month 2: Built an AI outreach system. Personalized investor emails at scale. My clients' response rates doubled.

Month 3: Automated investor updates, meeting prep, and CRM scoring. Freed up 20+ hours per week.

Month 4: Started using those 20 hours to actually grow the business instead of just running it.

Month 5: Built custom AI skills for each client's specific workflow. Stuff that used to take a week now takes an afternoon.

Today: Same team. Fraction of the hours. Grossly more efficient at everything we do.

I didn't get lucky. I didn't find a shortcut. I rebuilt every system in my business around AI.

The tools are available to everyone. The gap is who's willing to rebuild their process from scratch.

Most business owners are still trading time for output. AI lets you buy back your time.

What's one process in your business that's eating all your hours? Tell me below and I'll tell you exactly how to automate it.

A real estate investor told me last week he's "waiting to see how AI plays out."

He's raising his third fund. Manually. The same way he raised the first two.

Cold calls. Personal emails. Conference handshakes. One LP at a time.

His competitor down the street just raised $8M in 60 days.

Same market. Same asset class. Smaller track record.

The difference wasn't the deal. It was the system.

His competitor had:

→ 2,000 qualified LP prospects loaded into sequences
→ Personalized outreach hitting inboxes at 6am every Tuesday
→ A 52-week nurture drip educating cold leads into warm investors
→ AI-generated quarterly updates keeping 340 existing LPs engaged
→ Content publishing 5x/week positioning him as the market authority

The "wait and see" investor is still sending the same pitch deck to 40 people.

This isn't about early adoption anymore. We're past that.

This is about whether you're building a capital raising machine or running a capital raising hobby.

The investors who built systems 12 months ago are on their second and third raise. The ones who waited are still grinding through their first.

The gap isn't closing. It's accelerating.

Which side do you want to be on in 12 months? Drop "machine" and I'll show you where to start.

$89/month. 4 tools. 500 LP touches per month on autopilot.

Most real estate investors reach 10-15 LPs per week manually.

One email at a time.
One follow-up at a time.
One "let me circle back" at a time.

That math doesn't work when you're trying to raise $5M+.

Here's the stack running right now for our clients.

Apollo scrapes LinkedIn for accredited investors matching your criteria. 2,000 prospects in 20 minutes. $49/month.

An AI writing layer analyzes each prospect and writes a personalized first-touch email. Not a template with a name swapped in. A real message referencing their actual portfolio. $20/month.

A sequencing engine runs a 5-touch drip over 21 days. Each follow-up adapts based on opens, clicks, and replies. Built into Apollo.

Publer schedules LinkedIn content that warms up prospects before the cold email hits. They see your name before you're in their inbox. $12/month.

Old way: VA + agency + CRM = $4-8K/month.
New way: $89/month. Same output. Better personalization.

The investors raising the most capital right now aren't working harder.

They built a system and let it run.

DM me if you want to build this in your company.

I recorded a 10-minute voice memo on my phone last Tuesday.

It turned into 2 weeks of content.

Not edited transcripts.
Not rough drafts.
Polished, ready-to-post content in my exact voice.

Here's the workflow:

→ Record while driving
→ Upload the transcript to Claude
→ Get 5 LinkedIn posts, a newsletter intro, and 3 email subject lines

Total time from voice memo to finished content: 14 minutes.

The recording was about a deal we just closed. One story. One experience. One conversation with myself in the car.

Claude pulled out the insights, structured them into frameworks, and matched my writing style.

Most real estate investors think content takes hours.

It doesn't.

It takes one voice memo and the right system.

DM me if you want to build this in your company.

Your deal is not why LPs aren't investing.

I've seen syndicators with incredible deals — 18% IRR, strong markets, proven operators — struggle to fill a raise.

Then I've seen mediocre deals close in 3 weeks.

The difference is never the deal. It's the system behind the deal.

The guys closing fast have:

→ 500+ warm LP contacts getting weekly value
→ Personalized outreach based on each investor's portfolio
→ Automated nurture sequences running 52 weeks a year
→ Objection responses pre-built before the first call
→ Follow-up triggers based on email opens and clicks

The guys struggling have a great pitch deck and a spreadsheet of 40 contacts they email manually.

One is a machine. The other is hope.

I've helped 60+ syndicators build the machine version. The pattern is always the same.

Before: 6 months to raise $3M with constant manual hustle.
After: 8 weeks to raise $5M with systems doing 80% of the work.

The deal gets investors interested. The system gets them across the finish line.

If your pipeline is slow, don't change the deal. Change the infrastructure around it.

Which part of your raise is still manual? Drop it below — I'll tell you how to automate it.

Most CRE investors use AI to write emails.

The smart ones use it to underwrite 10 deals before breakfast.

Same tool. Completely different ROI.

It's not about having AI. It's about knowing where to point it.

AI can now analyze a 200-page OM in under 90 seconds.

That used to take your analyst an entire weekend.

The firms using this aren't smarter. They just see more deals faster.

Speed is the new edge in CRE.

A syndicator told me he uses AI to write his LP updates now.

Not to replace his voice. To draft the first version in 3 minutes instead of 3 hours.

He reinvests that time into actual LP conversations.

That's the play.

AI won't replace real estate investors.

But investors using AI will replace those who don't.

The gap is already showing up in deal flow, raise speed, and LP retention.

12 months from now it won't be close.

Raised $30 MM in capital for real estate through LinkedIn and Guest Podcasting | Posts about Real Estate, Writing, and Audience Building

Most fund managers treat visibility like a campaign.

Raise.
Deploy.
Go quiet.
Raise again.

And every cycle starts from zero.

That model caps scale.

I work with growth stage real estate and private equity sponsors ($50M–$150M AUM) to build durable investor visibility so capital conversations don’t start cold and raises compound over time.

This isn’t about going viral.

It’s about building signal, credibility, and allocator familiarity before you need the capital.

If you're a $50M–$150M sponsor ready to build the visibility that compounds into your next raise, apply below.

Matthew Baltzell 🌴

Most people think AI is replacing jobs.

But that’s not the real shift.


Look at this photo.

In the 1940s, a “computer” wasn’t a machine.

It was a person.

Rooms full of people doing calculations by hand.

Then machines replaced that work.

Humans started using computers.

Now something strange is happening again.

Computers are starting to use other computers.

AI tools.
Agents.
Automation.
Software running software.

Work that used to require departments can now be handled by one operator with the right systems.

And it’s creating a new divide.

Not...

People vs AI.

But...

Operators with leverage
vs
Operators doing everything manually.

In real estate and private equity this is becoming very obvious.

The sponsors raising capital the fastest aren’t necessarily the smartest.

They’re the ones building distribution systems.

Content.
Investor pipelines.
Automated outreach.
Deal narratives.
Investor updates.

Things that used to take a team of analysts and marketers can now be done by one operator with the right tools.

Which means the next generation of sponsors won’t just raise capital with relationships.

They’ll raise it with leverage.

Matthew Baltzell

$20M+ Raised | Investor Visibility for $50M–$150M Real Estate & PE Sponsors | Capital Raising Systems for Serious Sponsors

I saw this chart and immediately thought of my mom.

She never paid full price. Ever.

Coupons. Sales. Negotiating at the register.

If she got a deal — it was a good day.
If something was expensive — it was a ripoff.

She wasn’t wrong.

She was playing the game she was taught. Perfectly.

I remember her driving 25 minutes to Costco to save $4.
Arguing over a $7 coupon.
Skipping the better option because it “felt expensive.”

And sometimes that worked.

Until it didn’t.

The cheapest option saved money.

It didn’t always save reputation.

Cheap isn’t a flaw.

It’s a survival skill.

It just stops working above a certain altitude.

This chart doesn’t show good people vs bad people.

It shows different rules for different environments.

My mom mastered hers.

What rules are you still playing by?

I drove home after visiting my grandma and felt sad. She's 92. I don't see her enough.

This Christmas my wife and I went to her assisted living home for their holiday party. 

Nothing fancy. Just showing up. Sitting with her. Talking to her friends.

When we walked in, she looked at us like we were the whole world. Her friends did too.

She still gets her nails done every week. 
Still wants to look pretty. 

92 years old and young at heart in every way that matters.

What makes her eyes light up isn't much. Just family walking through the door.

And I keep thinking about how many of those moments I've let slip by. 

Too busy. 
Too distracted. 
Too much in my own head.

I don't have a big lesson here.

Just a reminder to myself...

Show up. Not just physically — but in the moment.

Matt Damon said Netflix has to repeat the plot 3–4 times because people are on their phones (Now apply that to investors.)



If you think...

- “I already explained the deal”

- “They saw the deck”

- “We covered this on the last call”

You’re overestimating attention.

Investors are scanning, not studying.

They’re comparing you to 5 other deals this week.

They remember patterns, not paragraphs.

That’s why the best sponsors:

- Repeat the thesis

- Reinforce the why now

- Reanchor the risk story

- Restate the downside protection

Same message.
Different format.
Every touchpoint.

Call.
 Deck.
 Email.
 Podcast.
 Follow-up.

If Netflix needs repetition to keep viewers…
...You need it to move capital.

If your deal feels “obvious” to you,

it’s probably still unclear to them.

After 25+ conversations with real estate sponsors about raising capital, one pattern kept repeating.

When it came to capital…

It was feast or famine.

There was almost no middle ground.

Sponsors fell into two groups.

𝗧𝗵𝗲 𝗢𝘃𝗲𝗿𝘀𝘂𝗯𝘀𝗰𝗿𝗶𝗯𝗲𝗱

Their LP pipeline was already full.

Deals oversubscribed.
Investors waiting for allocations.
Capital ready when a deal appeared.

Blah, Blah, buttttt....

They were still looking for more investors.

Because experienced sponsors understand something most people miss:

The best time to raise capital isn't when you need capital. 

𝗧𝗵𝗲 𝗭𝗲𝗿𝗼 𝗣𝗶𝗽𝗲𝗹𝗶𝗻𝗲

Dry LP pipeline.

No consistent investor flow.
Starting from zero every raise.
Scrambling for investor conversations in hubspot at midnight. 

Every deal becomes a fire drill.

The stress.
The pressure. 
The cursor blinking at you waiting for your next email blast!

No bueno. 

The takeaway...

There were very few sponsors in the middle.

You either have:

A machine that attracts investors

or

You start from zero every time you raise and are left holding the empty bag. 

The sponsors in the oversubscribed category all had something in common.

They were building investor relationships long before they NEEDED capital.

The most common pattern I saw..

A podcast.
A strong LinkedIn presence.
A newsletter.
Consistent content documenting their deals, their thinking, and their process.

Not selling.

Just showing up.

By the time an investor discovered them, through a post, an episode, or a piece of content, they already felt like they knew the sponsor.

That's the difference between a cold ask and a warm conversation.

Raising capital isn’t something you switch on.

It’s something you build.

Alex Rodriguez made $441,000,000 playing baseball.

He parlayed it into $300M+ in real estate.

Here’s how he did it:

He LEARNED from the BEST.

• A-Rod didn’t just spend. He studied.
• Sat in rooms most athletes never see.
• Treated investing like a second career NOT a hobby.
• Learned underwriting, capital stacks, deal structure.
• Built a relationship with Barry Sternlicht (Starwood Capital).

That became the foundation.

He TOOK ACTION.

• Started investing in multifamily while still playing.
• Focused on cash-flowing assets, not headlines.
• Built A-Rod Corp as an investment platform.
• Partnered with experienced operators.

He transitioned from athlete…

To operator.

To allocator.

Most of us won’t sign a $275M contract.

But anyone can:

• Study capital allocation.
• Learn from serious operators.
• Binge watch Landman on the treadmill. 
• Build relationships above their weight class.

The shift isn’t talent.

It’s identity.

Income is temporary.

Ownership compounds.

P.S. The real question everyone wants to know?

Was the $252M Yankees contract…

Or the first apartment deal…

The better investment?

"When we had a deal."

That was their entire investor relations strategy.

They were raising $15M.

I audited 12 operators last month. This wasn't the only one.

Good deals. 
Credible sponsors. 
Empty pipelines.

The raises weren't broken. The systems were.

Here's what I saw:

→ No investor CRM (pipeline = inbox + memory)
→ No nurture engine (deal email → silence for 6 months)
→ Two had zero post close reporting cadence
→ Raising in 60 day sprints instead of building a 12 month engine

The real problem:

Raising $5M isn't about finding investors.

It's about becoming investable.

Operators at the $5M–$25M level don't struggle because deals are bad.

They struggle because LPs wire on:

→ They've seen you before
→ They trust your process
→ They respect your reporting
→ They've been hearing from you for months

Not excitement.

If you're raising $5M+ and have $25M+ AUM…

I'll audit your capital system.

Direct feedback.

DM me "AUDIT."

𝗣.𝗦. 𝗛𝗼𝘄 𝗺𝗮𝗻𝘆 𝗶𝗻𝘃𝗲𝘀𝘁𝗼𝗿𝘀 𝗶𝗻 𝘆𝗼𝘂𝗿 𝗽𝗶𝗽𝗲𝗹𝗶𝗻𝗲 𝗵𝗲𝗮𝗿𝗱 𝗳𝗿𝗼𝗺 𝘆𝗼𝘂 𝘁𝗵𝗶𝘀 𝗺𝗼𝗻𝘁𝗵?

Started learning guitar 6 months ago. Turns out being bad at something is good for business. Here’s why…

I decided to post proof.

This video confirms I’m still not good.

And that’s the point.

No leverage.
No shortcuts.
No AI saving my rhythm.

Just reps.

Most adults won’t start something new because they don’t want to look average.

In business it’s the same.

They over plan.
Over edit.
Overthink.

All to protect their ego.

Protecting your ego is the most expensive habit in business.

You focus on fundamentals.
You get fast feedback.
You improve.

Six months in, I’m not great.

But I’m better.

Sidenote: Background audio courtesy of two tiny humans who also don’t care that I’m a beginner.

What are you learning right now that you’re not good at yet?

An 18% IRR deal fell apart in 60 seconds.

All I did was paste the OM into ChatGPT.

It rewrote the deal in plain English.

That’s when the cracks showed.

• 18% IRR… assuming exit cap compression
• Rent growth projected at 2x the submarket
• “Value-add” mostly cosmetic upgrades

Nothing dishonest.

Just optimistic.

There’s a difference.

AI doesn’t get impressed by glossy decks.

It asks one question:

“What has to go perfectly for this to work?”

Great decks sell.

Great underwriting survives.

Big difference.

Most people say they want freedom.

But very few want the discipline required to get it.

That’s why most people stay employees.

Half of your LPs might never invest with you again.

And it probably has nothing to do with your returns.

Two operators.
Same market.
Similar returns.

One has 47% LP reinvestment.
The other averages 84%.

The difference isn’t the deal.

It’s discipline.

Low reinvestment operators:

• Update LPs when they need something
• Late reports
• Silence between raises
• Investor relations = reactive

High reinvestment operators:

• Monthly updates
• Proactive communication
• Clear forward narrative
• Investor relations = compounding system

The math:

50% re-invest = rebuild half your book every raise.
85% re-invest = replace 15% and scale.

Most sponsors don’t have a deal problem.

They have a relationship infrastructure problem.

If you don’t know your LP reinvestment rate, that’s the first red flag.

I’m running a Capital Raising Infrastructure Audit for sponsors actively raising $5M+.

We look at LP retention, communication cadence, visibility, and raise velocity.

Comment “AUDIT” and I’ll send details.

Everyone’s arguing about housing.

But almost nobody is talking about the real driver..

Capital.

Young buyers want cheaper homes.

Homeowners want prices to keep rising.

Politicians promise affordability.

But the housing market isn’t driven by hopes or politics.

It’s driven by capital flows.

Demographics.
Interest rates.
Credit availability.
Institutional money.
Government incentives.

When capital is cheap, assets inflate.

When capital tightens, deals stop penciling.

And right now we’re watching the system try to do something impossible:

Make housing cheaper...

...while protecting the trillions of dollars already sitting in residential real estate.

That’s not how capital markets work.

Asset values don’t reset politely.

They reprice when capital conditions change.

So if you’re under 40 and waiting for someone to “fix housing”…

Good luck.

Because the housing market isn’t a fairness system.

It’s a capital market.

The real move?

Understand how capital flows into assets.

Build skills that compound.

Create income that scales.

And get ownership exposure as early as you can, even if it’s uncomfortable.

Because the people who win aren’t the ones complaining about the system.

They’re the ones who understand how money moves inside it.

Agree or disagree?

I spoke with a 30 year operator managing $50,000,000 in assets who realized he couldn’t scale without visibility.

Great track record.
Strong returns.
Solid local reputation.

But he hit the Friends & Family ceiling.

And here’s the uncomfortable truth:

Most $50M sponsors aren’t stuck because of performance.

They’re stuck because no one outside their zip code knows they exist.

He knew he needed RIAs and Family Offices.

That requires trust at scale.

Not another lunch meeting.

We mapped the strategy.

Then it stalled.

Why?

Infrastructure.

No real investor relations support.
No systemized follow-up.
No capital discipline.

And the quiet fear:

“If this works… can we even handle it?”

Marketing feels risky when your backend is fragile.

Fragile doesn’t scale.

Visibility compounds.

But only if the machine behind it can absorb demand.

Otherwise, you don’t have a marketing problem.

You have an operator problem.

What’s harder:

Finding investors?

Or becoming the firm that can handle them?

I reviewed a 92 unit apartment deal this week.

On paper it looked great...

Nice looking property.
Good market.
Classic value add play.

The story was simple:

Buy the property.
Renovate units.
Push rents.

On paper, it all works.

But after looking at a lot of deals lately, I keep coming back to the same three things.

3 things I always look at now:

𝟭. 𝗥𝗲𝗻𝘁 𝗮𝘀𝘀𝘂𝗺𝗽𝘁𝗶𝗼𝗻𝘀

• The plan here was roughly $150–$200 rent increases
• That’s where most of the investor returns come from

But the real question is simple:

Will tenants actually pay those rents?

𝟮. 𝗗𝗲𝗯𝘁

• Interest rates matter more than people want to admit
• Refinance timing can change the entire outcome of a deal

A property can perform well…

…and still struggle if the debt is wrong.

𝟯. 𝗧𝗵𝗲 𝗼𝗽𝗲𝗿𝗮𝘁𝗼𝗿

This one matters more than anything.

• Leasing strategy
• Tenant quality
• Renovation execution

A good operator can fix a mediocre deal.

A bad operator can wreck a good one.

The more deals I look at, the more I realize something:

Most deals don’t fail because of the property.

They fail because of assumptions.

TLDR, 

When you look at a real estate deal…

What's the first thing you check for?

I’ve audited 3 capital raises last week.

The pattern is consistent.

Operators who close don’t rely on better decks.

They build better infrastructure.

Here are the 3 things that separate operators who close from operators who stall:

𝟭. 𝗧𝗵𝗲𝘆 𝗻𝘂𝗿𝘁𝘂𝗿𝗲 𝗯𝗲𝗳𝗼𝗿𝗲 𝘁𝗵𝗲𝘆 𝗻𝗲𝗲𝗱 𝗰𝗮𝗽𝗶𝘁𝗮𝗹

Sponsors who close fast started conversations 6–12 months before the deal.

Sponsors who stall?
First touchpoint is the deal email.

LPs don’t wire on excitement.
They wire on familiarity.

𝟮. 𝗧𝗵𝗲𝘆 𝗸𝗻𝗼𝘄 𝘁𝗵𝗲𝗶𝗿 𝗻𝘂𝗺𝗯𝗲𝗿𝘀 𝗰𝗼𝗹𝗱

Average check size.
Re-investment rate.
Time from first conversation to close.

If you can’t answer those in 10 seconds, you’re guessing.

Guessing doesn’t scale past $10M.

𝟯. 𝗧𝗵𝗲𝘆 𝘁𝗿𝗲𝗮𝘁 𝗶𝗻𝘃𝗲𝘀𝘁𝗼𝗿 𝗿𝗲𝗹𝗮𝘁𝗶𝗼𝗻𝘀 𝗹𝗶𝗸𝗲 𝗼𝗽𝗲𝗿𝗮𝘁𝗶𝗼𝗻𝘀

Monthly updates.
Documented process.
CRM with real pipeline visibility.

Most operators treat IR like an afterthought until they need to raise again.

The best ones treat it like asset management.

Across every raise I’ve looked at, the pattern holds:

Infrastructure beats pitch.

𝘐𝘧 𝘺𝘰𝘶’𝘳𝘦 𝘢𝘤𝘵𝘪𝘷𝘦𝘭𝘺 𝘳𝘢𝘪𝘴𝘪𝘯𝘨 $5𝘔+ 𝘢𝘯𝘥 𝘸𝘢𝘯𝘵 𝘢 𝘴𝘦𝘤𝘰𝘯𝘥 𝘴𝘦𝘵 𝘰𝘧 𝘦𝘺𝘦𝘴 𝘰𝘯 𝘺𝘰𝘶𝘳 𝘤𝘢𝘱𝘪𝘵𝘢𝘭 𝘪𝘯𝘧𝘳𝘢𝘴𝘵𝘳𝘶𝘤𝘵𝘶𝘳𝘦, 𝘐’𝘮 𝘰𝘱𝘦𝘯 𝘵𝘰 𝘢 𝘧𝘦𝘸 𝘤𝘰𝘯𝘷𝘦𝘳𝘴𝘢𝘵𝘪𝘰𝘯𝘴 𝘵𝘩𝘪𝘴 𝘮𝘰𝘯𝘵𝘩.

I thought the whole world was using AI already.

Then I zoomed out.

And noticed something nuts about this chart.

Do you see it?

Almost the entire thing is grey.

That grey represents billions of people who have never used AI.

Not once. Zip. Nada.

No ChatGPT.
No image generation.
No automation.

Nothing.

Meanwhile online it feels like the opposite.

Every day you see:

• a new AI model launch
• someone automating their company
• a teenager building a startup that tracks calories from photos

It creates the illusion that everyone is already miles ahead.

They’re not.

(Sorry, Aunt Debbie.)

Most people still think AI is:

“that thing that makes weird pictures”

or

“the robot that writes comments on LinkedIn.”

They’ve never seen what it looks like when AI becomes leverage.

The tiny corner of this chart?

That’s the group experimenting with it every day.

The builders.
The operators.
The people quietly compressing 10 hours of work into one.

Just out there making it happen.

And that’s where the real shift is happening.

Not in hype.

In workflow.

AI doesn’t have a competition problem yet.

It has an awareness problem.

Most of the world hasn’t even stepped onto the field.

Which means the edge right now isn’t technical brilliance.

It’s curiosity.

Open the tools.
Use them daily.
Experiment.

You don’t need to understand neural networks.

(Trust me… I don’t.)

You just need to be slightly earlier than the crowd.

And right now, the crowd is still figuring out what AI even is.

So the real question is…

Are you experimenting with AI in your work yet…

or still watching it happen from the sidelines?

Everyone’s debating whether this coffee shop’s AI surveillance is ethical...


Anna: 20 cups.
Olga: 3 cups.
John: Where is he?

Coffee. Customers. Company.  

Everything tracked by the minute. 

3.7 million people have opinions.

Meanwhile…

LPs writing $250K–$5M checks into $50M–$150M funds still get:

• Quarterly PDFs
• Retroactive performance
• Carefully worded updates

No real time visibility...
...No capital level transparency.

We can track barista productivity down to every Oatmilk Shaken Espresso.

But not investor capital down to the dollar?

Hmmmm...

The tech exists.

𝗧𝗵𝗲 𝗴𝗮𝗽 𝗶𝘀𝗻’𝘁 𝗰𝗮𝗽𝗮𝗯𝗶𝗹𝗶𝘁𝘆. 𝗜𝘁’𝘀 𝗽𝗿𝗶𝗼𝗿𝗶𝘁𝘆.

And the sponsors who close Fund II effortlessly?

They understand that visibility compounds trust.

P.S. Would you walk into a coffee shop that hides how it operates?

If I were a $50M+ sponsor using LinkedIn DMs to connect with investors, here's how I'd approach it.

𝟭. 𝗡𝗼 𝗽𝗶𝘁𝗰𝗵 𝗶𝗻 𝘁𝗵𝗲 𝗰𝗼𝗻𝗻𝗲𝗰𝘁𝗶𝗼𝗻 𝗿𝗲𝗾𝘂𝗲𝘀𝘁. 

A connection is a doorway, not a closing argument.

Most sponsors burn their first impression trying to explain the opportunity in 300 characters.

Serious operators build familiarity first.

𝟮. 𝗡𝗼 𝗽𝗶𝘁𝗰𝗵 𝗶𝗻 𝘁𝗵𝗲 𝗳𝗶𝗿𝘀𝘁 𝗺𝗲𝘀𝘀𝗮𝗴𝗲.

I'd start with positioning.

"Appreciate the connect. We're active in [strategy] and expanding relationships with investors aligned with that thesis. Are you currently allocating into opportunities like that, or mostly observing this cycle?"

That does three things:

• Establishes what you're building
• Signals growth (not need)
• Qualifies without begging

Positioning first. Question second.

Not the other way around.

𝟯. 𝗜 𝘄𝗼𝘂𝗹𝗱𝗻'𝘁 𝗺𝗮𝗸𝗲 𝗼𝘂𝘁𝗿𝗲𝗮𝗰𝗵 𝗱𝗲𝗮𝗹 𝗱𝗲𝗽𝗲𝗻𝗱𝗲𝗻𝘁.

If every DM is tied to a live raise, you're negotiating from urgency.

Serious sponsors build repeat touch points:

• Thoughtful content
• Market commentary
• Occasional investor updates

So when a deal is live, the conversation isn't cold.

𝟰. 𝗙𝗼𝗹𝗹𝗼𝘄-𝘂𝗽 𝗶𝘀 𝗻𝗲𝘄 𝗰𝗼𝗻𝘁𝗲𝘅𝘁, 𝗻𝗼𝘁 𝗮 𝗿𝗲𝗺𝗶𝗻𝗱𝗲𝗿.

Not: "Just checking in."

Instead, I'd add signal.

An update. A shift in thinking. A market observation. A closed deal. A deal we passed on.

Investors don't respond to pressure.

They respond to thoughtful operators.

Because capital doesn't move toward need.

It moves toward clarity, consistency, and conviction.

And here's the filter:

If you're uncomfortable reaching out to investors without a live deal…

You don't have a capital strategy.

You have a dependency.

The sponsors who scale capital treat outreach like a system.

Not an event.

If you're building that system and want a second set of eyes on your outreach DM me.

No pitch. Just a real conversation.

I went looking for a dive bar in Prague and ended up here...


Back in 2015 my brother got married in London.

After the wedding my family decided to extend the trip and visit Prague.

The group:

My grandma
My mom and dad
My Aunt Deb
And me, the young buck in his 20s

Day one we did the usual tourist stuff...

Charles Bridge.
Cinnamon strudel.
Cobblestone streets.

Then around 7 PM everyone went to bed.

Trip over.

I thought… there’s no way this is how Prague ends.

So like any guy in his 20s, I went searching for the coolest dive bar I could find.

After about an hour of digging through Yelp I found a place called Anonymous Bar.

The name alone hooked me.

Hidden.
Exclusive.
Mysterious.

(I’m game.)

I screenshotted the location on my iPhone 4 and headed out.

Started asking people.

Liquor store owner?
No idea.

Random locals?
Never heard of it.

Finally a hotel doorman pointed down a street and said in a thick Eastern European accent:

“Milstroff Street.”

Three minutes later I was walking down a dark alley under a massive stone arch between two dilapidated buildings.

No people.

Just a faint fluorescent streetlight on its last flicker.

At this point my gut instincts were saying…

This might be a bad idea.

But curiosity won.

Then I saw a guy wrestling wooden crates out of a rusted red hatchback.

I pointed and asked:

“Anonymous?”

He nodded.

Behind him were seven tea lights leading to a hidden door.

Inside?

A full 1920s speakeasy frozen in time.

Bartenders with waxed mustaches twisted to sharp points.
Candlelight flickering off copper fixtures.
Bossa Nova bleeding softly through the room.

The bartender handed me a DVD case.

Inside was a drink menu written entirely in code.

So, I pointed to something that looked like whiskey.

He made the drink with flames, smoke, and a full show.

Then he placed it in front of me…

Put a V for Vendetta mask on my face…
Pulled out a Polaroid camera…
And took this photo.

That photo exists because I went looking.

That’s it.
That’s the lesson.

Go looking.

P.S. What's the last thing you did just because curiosity won?

Floyd Mayweather made $1,000,000,000+

So why is he still chasing checks?

Because income isn’t infrastructure.

It’s about operators who confuse one big year with a durable system.

In capital raising, this shows up fast.

You close a $20M fund.
Fees hit.
Confidence spikes.

Then 12 months later…

Your “pipeline” was three warm relationships and a conference badge.

LPs invested… and forgot you exist.

Now you’re back in scramble mode.
Taking meetings you wouldn’t have entertained last year.
Stretching timelines.
Softening terms.

You weren’t compounding.

You were sprinting.

Raising capital without systems is like winning one fight with no camp.

Feels powerful.

Until the market punches back.

The sponsors who last don’t just close.

They:

Stay visible between raises.
Nurture LPs before they need them.
Build deal flow before they announce it.
Track capital velocity like it’s oxygen.

Because when you stop hunting…
…does money still move?

That’s the difference between a high earner
and a real operator.

Don’t celebrate the purse.

Build the machine.

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