15 Things I Wish I Knew Before Breaking Into Finance & Big Money
Hard-earned lessons from real deals, real losses, and real wins.
Last week, I got a call.
Some guy wanted to break into finance and big-ticket deals.
He had the drive. The hunger. The ambition.
But no idea how the game is actually played.
And I get it. Because I’ve been there.
I went from $Billion deals in investment banking and private equity…
…into the world of real estate,
Got burned by contractors,
Had banks pull out on me mid-deal,
And had to refinance multi-million-pound projects in less than 90 days to survive.
I made every mistake in the book.
Here are 15 brutal truths I wish I knew before stepping into the world of serious money:
1) YOUR REPUTATION IS YOUR FIRST ASSET
Before you have capital, your name is your currency.
One bad deal. One burnt investor. One missed deadline. And you’re done.
In finance, trust compounds - Positively or Negatively.
• If people trust you, they will back your deals
• If they don’t, you won’t even get a seat at the table
2) YOUR FIRST DEAL CAN MAKE OR BREAK YOU
The worst advice? “Just get started.”
No. Your first deal is your foundation.
A great first deal can open doors for decades.
A bad one? You’ll spend years recovering.
Want to avoid a disaster? Partner with experience. Protect your downside. Plan your exit.
3) YOU DON’T NEED MONEY - YOU NEED LEVERAGE
Finance isn’t about having money. It’s about controlling money.
The best players don’t risk their own capital – they use other people’s money (OPM).
• Banks, investors, and institutions will finance good deal-flow if structured well
• If you control the asset, the funding, and the terms, you control everything
4) CAPITAL RAISING IS THE #1 SKILL YOU NEED
Every private equity firm, hedge fund, and real estate mogul gets built on capital.
If you can raise money, you’ll never be broke.
Want to attract capital? Answer these:
• What’s your track record
• Why should investors trust YOU
• What’s the bulletproof upside
Weak answers = no money.
5) PEOPLE WILL WASTE YOUR TIME - LEARN TO FILTER
99% of people talk a big game and do nothing.
Real investors? Move fast.
Here’s how to filter:
• People with money talk in specifics
• People without money talk in theory
If they can’t tell you their exact investment criteria, timing,
…and capital availability, walk away.
6) PLAY WHERE YOU HAVE AN UNFAIR ADVANTAGE
The biggest players dominate niches they understand better than anyone.
Find where you have an edge, and go all in.
• If you have deep industry knowledge, find deals others overlook
• If you have capital access others don’t, negotiate better terms
• If you understand regulations better than others, exploit inefficiencies
7) NEVER RELY ON ONE BANK
Banks will shake your hand today and pull funding tomorrow.
I’ve seen banks:
• Approve financing – then disappear when the deal closes
• Pull out on developers mid-construction (happened to me)
• Call in loans when “market conditions change”
If you don’t have backup lenders, alternate capital sources, and emergency cash,
You are gambling your future.
8) IF YOU’RE NOT RUTHLESS ON EXECUTION, YOU’LL GET CRUSHED
Most people overestimate their ability to execute,
and underestimate how fast things can go sideways.
This game is about:
• Speed – Get deals done fast
• Precision – Avoid stupid mistakes
• Control – Own every variable possible
9) INVESTORS BACK PEOPLE - NOT SPREADSHEETS
A perfect financial model won’t save a bad deal.
Investors bet on vision, confidence, and execution.
• If you don’t believe in the deal, no one else will
• If you can’t sell yourself, the numbers don’t matter
10) IT’S A RIGGED GAME - UNTIL YOU RIG IT YOURSELF
The best deals never hit the market.
By the time a good deal is public, the insiders have already passed on it.
You need to be inside the right rooms before the opportunities exist.
11) DON’T CHASE SMALL DEALS - THINK BIGGER, SOONER
It takes the same effort to close a £10M deal as a £1M deal – but the upside is 10x larger.
• Investors want big, scalable opportunities
• Small deals won’t build real wealth
If you want to attract serious money, structure deals at a scale that gets attention.
12) IF YOU MESS UP, FIX IT FAST
Every top player has taken losses.
How fast you recover is what matters.
• Own your mistakes
• Fix them immediately
• Keep moving forward
Most people dwell on failures instead of correcting them.
13) YOUR NETWORK WILL EITHER ELEVATE YOU OR KEEP YOU BROKE
Who you spend time with dictates your opportunities.
• Broke people discuss problems
• Wealthy people discuss solutions
Find mentors, investors, and partners who force you to level up.
14) CONTROL THE DOWNSIDE - THE UPSIDE WILL TAKE CARE OF ITSELF
Amateurs focus on how much money they can make.
Professionals focus on how much money they can lose.
Every deal I do now gets structured to protect capital first, maximise upside second.
If the worst-case scenario still allows you to win, you’ve already beaten 90% of investors.
15) MOST PEOPLE WILL QUIT BEFORE THEY EVER WIN
Real wealth gets built by staying in the game long after others fold.
• The ones who last through the market cycles get rich
• The ones who panic and quit get nothing
Most people never build real wealth because they quit too soon.
FINAL THOUGHTS:
These aren’t theories.
These are my own battle-tested lessons from real deals, real losses, and real wins.
Most people will read this and do nothing.
They’ll think about it, nod their heads, and move on with their lives.
The winners will take action.
Which one are you?
If you’re serious about scaling into high-stakes finance and sustainable wealth creation -
You belong here.
My intention is to bring you massive value in future editions of Upgraded Investor by sharing my personal experience to date.
This is the place where I break down real deals, real strategies, and how we can all play the game at the highest level.
Why do I do this?
Because I believe that together, we can become a true force for positive change in our industry.
So until next time, let’s get back out there and build wealth with purpose.
Matt
Great article yet again Matt. This really resonates with me. Great work.