Founder of Prowess Inc. // Investor // Writer @entrepreneur // Prvsly for @Forbes @Refinery29 @huffpost
Puerto Rico
Joined June 2012
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Ashley Crouch retweeted
UBS asked 215 entrepreneurs (combined revenue: $34.3 billion) what they're planning for 2026
1/ A big handover is coming...
32% want out of their business within 5 years
For the over-65s, it's 57%
How they plan to exit:
• 40% sell to a strategic buyer
• 23% pass it to the kids
• 13% sell to private equity
• 6% are aiming for an IPO
2/ But there are serious challenges
• 32% admit they didn't build enough wealth outside the business
• 42% plan to sort out personal wealth only after they sell
• So the exit is the whole retirement plan
3/ And entrepreneurs are worried
• 67% worry about prepping the next gen to handle the money
• 61% worry about doing it tax-efficiently
• Europe's the most tax-anxious (72%)
• Asia-Pacific's focused on keeping wealth in the family for generations
4/ Here's where entrepreneurs are getting advice:
• 69% will ask a lawyer, tax advisor or family advisor about succession
• 47% will ask their banker
• Only 23% will ask their own children
Ashley Crouch retweeted
Real Estate 2026
5 Key Themes for Family Offices
Here's the lowdown:
1. Residential real estate: cross‑border capital on the rise
• Cross-border demand is rising
• Dubai leads super-prime sales; Abu Dhabi, Qatar, Singapore and Hong Kong see upticks
• London softens on tax reform
• Southern Europe attracts lifestyle capital
• Housing shortages across Europe support rents and defensive income.
2. Commercial RE: turning a corner?
• Rate cuts in the EU and Switzerland support recovery; US/UK yields remain competitive
• Prime offices and retail outperform; secondary assets lag
• Offices, residential and logistics top 2026 allocations.
3. Logistics, hotels, data centers expand
• E-commerce drives logistics demand
• Hospitality remains strong post-COVID
• AI fuels data centre and energy infrastructure growth
• Defence spending creates niche real estate demand.
4. ESG still matters, especially in Europe
• Regulation and next-gen expectations sustain ESG focus, though historic assets pose retrofit challenges
5. Private equity returns
• Blackstone, Brookfield, Ares redeploy capital into discounted logistics, healthcare and public-to-private deals
• Generational capital sees opportunity in volatility
- Deutsche Bank, Wealth Management, 2026
Ashley Crouch retweeted
The Dubai International Financial Centre (DIFC) reported 1,289 family-related entities in 2025
An increase of 61% since 2024
The UAE has become a major hub for family offices
All the forecasts were positive
The UAE rode the wave of mobile capital and people, but will it cut both ways?
IQEQ: UAE, Key predictions for family offices in 2026 (22 December 2025):
Ashley Crouch retweeted
“It’s hard to overstate the peril for Dubai's economic model. The physical damage may be slight, and most of the pain thus far is psychological.
But Dubai's status as a safe-haven for expatriates and their businesses is in increasing doubt.
The longer the war continues, the more intense the search will be for alternative locations. Dubai needs this war to wrap up now. International capital is highly mobile.”
Jim Krane, fellow at Rice University’s Baker Institute
Ashley Crouch retweeted
You can still win bigger than you'd ever imagine.
Even with all the AI doomerism, you can just lock in for the next 2 years and set up your family for a generation.
Ashley Crouch retweeted
The richest people I know are doing one of 2 things:
Going all‑in on AI - building, and not sleeping while they try to understand what is coming.
Selling everything - cashing out and going to Europe, New Zealand, or off-grid.
Weird how few are in the middle.
Ashley Crouch retweeted
If I sold my company today, I'd start my next multi-million dollar business in 90 days using only AI.
Here's how:
I'd create 5 AI specialists that work 24/7 for a fraction of what a single employee costs.
Meet my AI dream team:
THE ANALYST
I'd upload a detailed vision document explaining my business model
I'd have it identify emerging market opportunities with hard data
I'd ask: "Find the top 3 underserved problems in profitable industries"
I'd demand specific research on customer behavior and spending patterns
I'd make it spot trends competitors are missing
THE GROWTH HACKER
I'd ask: "What's the fastest path to 10,000 customers with supporting evidence?"
I'd have it design rapid testing frameworks for every assumption
I'd make it identify the highest-impact growth levers specific to my business
I'd run every strategy through "What would break this?" analysis
I'd demand concrete timelines and success metrics for each test
THE SALES MACHINE
I'd never ask for generic sales copy - too weak
I'd build systematically: pain points → value props → objection handling → close
I'd force it to create sales sequences that convert strangers into buyers
I'd make it design irresistible offers that feel like no-brainers
I'd have it craft follow-up systems that turn one-time buyers into repeat customers
THE SYSTEM BUILDER
I'd make it map out every process needed to scale efficiently
I'd have it create detailed automation workflows for customer onboarding
I'd ask for complete operational frameworks that work without me
I'd make it identify bottlenecks before they become problems
I'd demand step-by-step scaling plans with specific resource requirements
THE BRAND BUILDER
I'd have it create 20+ pieces of authority-building content per week
I'd make it analyze successful competitors and find content gaps
I'd force it to create posts that position me as the obvious expert
I'd have it develop content that builds trust before anyone meets me
I'd make it test messaging until it resonates with my exact audience
AI without direction is worthless.
AI with basic direction gets basic results.
AI with elite direction builds empires.
While you're debating AI ethics, I'm building AI empires.
Come to my free masterclass on Tuesday, November 11th. I’ll walk you through the AI system that actually works: buff.ly/Er4k2EN
Ashley Crouch retweeted
Barriers to Setting Up a Family Office:
As per the latest Julius Baer & PwC Family Barometer 2025
• 40.8% cited cost as the primary obstacle to creating a family office
• 29.5% said complexity of management is a major barrier
• 28.3% said wealth not large enough
• 22.9% mentioned lack of perceived benefits
• 9.7% said everything already managed by a bank
“He had unfinished work. But he didn’t have unfinished business.”
Is there anything in your life you need to clean up?
Unreal.
Erika Kirk’s full speech at Building a Legacy: Remembering Charlie Kirk
@mrserikakirk
"I forgive him.” - @MrsErikaKirk
One of the most powerful things I have ever seen in my life.
I am shaken to the core.
Ashley Crouch retweeted
Where young people get their financial content
YouTube, TikTok, Insta, X, Reddit
The times, they are a-changin'
Ashley Crouch retweeted
Easiest path to 7 figures right now
1. Start an agency
2. Do it AI enabled around content
3. Pitch it on X
4. Save all receipts of wins
5. Use your posts as proof & ads
Ashley Crouch retweeted
You've just banked $50M, how do you manage it:
private bank, multi-family office, self-manage
This tweet got people talking
And we're taking it to the next level
We spoke to
→ UBS
→ The Whittier Trust
→ An individual managing $50M of family capital
🥊 REPRESENTING private banks
UBS
Mark Tepsich, Executive Director and Senior Strategist for Family Office Solutions
AUM: $5 Trillion
“So, the client doesn't have to and should not self-manage here, as the domains can be complex… What the client must be, however, is engaged and must spend the time to understand his or her complexity.”
🥊 REPRESENTING multi-family offices
Whittier Trust
Jeff Truet, Vice President, with assistance from Sam Kendrick, Portfolio Manager
AUM: $26 Billion
“Unlike publicly traded firms whose primary obligation is to shareholders, Whittier’s priority is our clients. As a trust company, we provide comprehensive, white-glove fiduciary services.”
🥊 REPRESENTING self-management
Mr. Name Withheld
AUM: $50 million
"After over 15 years watching ‘how the sausage gets made’, from custody operations to fee structures to actual portfolio construction, I knew I had to build something different for my own family capital.”
For the full story, look out for Friday's newsletter
Ashley Crouch retweeted
People don’t understand two things. Charlie is this generations MLK. Non-violent, faced mobs, hard truths, man of faith. More than half the US woke today & said enough.
BUT How do we fight cowards? who don’t debate, assassinate, wear masks? What do you do now? People need an answer.