What I Wish I Knew About Money Before Making My First Million

The Unlimited Capital Implementation System

Sep 11, 2025

Let me tell you about the most expensive mistake I was making with money. Like everyone else, I was filtering every opportunity through my bank account balance instead of my actual capabilities.

Most people think money problems get solved by having more money. After six exits and deploying over $300 million in capital, I learned something different. The real breakthrough comes from understanding when you're not dealing with a money problem at all.

Let me explain how one interaction changed everything for me.

The Problem: You're Using the Wrong Filter

About 15 years ago, my business partner Peter Loewy and I were looking at an investment opportunity bigger than anything we'd tackled before. At Srilo Capital (I was the “Sri” and he was the “Lo”), my gut reaction was predictable: "I'm not sure we can afford this."

Peter stopped me cold. "That's the last time we should ever say something like that."

I was confused. And mildly irritated.

We literally didn't have enough cash at play for this investment. The math was simple: big opportunity, not enough money.

But Peter asked me something that rewired my brain: "Assuming we had all the assets we needed, would you still recommend we do this?"

"This is a no-brainer," I replied. "I'd do it seven times over."

We had a strategy call for the deal coming up that afternoon and I was curious how it was going to go.

During the call, when they asked about our investment capacity, Peter said something I'll never forget: "If the opportunity is a good fit for us, you can assume that we have unlimited capital."

Here's what Peter understood that I didn't. When you think about what you can afford, you immediately start thinking about not having enough money. While that might be true, it doesn't help you become a great investor.

And as a professional investor, let me tell you that it’s only a matter of time before you run out of money yourself.

He explained it perfectly: "Money solves the problem of not having money." But then he reminded me of one three-letter word that changes everything: How.

Instead of asking "Can I afford that?" we should ask "How can I afford that?"

The Framework I came up with to help me reconcile all of this: The Five-Asset Inventory

You're not limited by money. You're limited by thinking money is your only asset.

You actually have five things you can trade with:

Money – The obvious one everyone focuses on, but just one piece of the puzzle.
Relationships – Your network and the trust you've built with people who can open doors.
Time – Sweat equity and effort you can contribute when cash is tight.
Skill – Technical expertise or unique capabilities that add real value to deals.
Brand – Your reputation and ability to bring credibility or distribution power.

Most people get stuck because they only see the first asset. Every opportunity can be structured using different combinations of these five assets.

After building and selling multiple companies, and investing on over 100+ deals, I will tell you something confidently that you will not believe: Money is the easiest part of the deal.

If you go back to Peter’s line on the call:
If the opportunity is a good fit for us, you can assume we have unlimited capital.

When we asked "How can we afford to do this?" instead of "Can we afford this?" we found funding sources we hadn't considered, negotiated better terms, and got a more profitable structure than our original plan.

We didn’t get stuck in a logical, thinking constraint.

Why This Kinda Changes Everything

This makes you what I call an opportunity facilitator instead of just a capital allocator.

Instead of filtering opportunities through your wallet, you start filtering them through potential. Instead of asking "What's good for me with my current constraints?" you ask "What's the best version of this opportunity, and how can I contribute to making that happen?"

Sometimes that means you bring the money. Sometimes you're the connector. Sometimes you're the one doing the work. Sometimes you're the strategic advisor.

But you're never out of the game just because you're out of cash.

The Story That Proves It Works

Let me tell you what happened after that conversation. We needed to raise capital for a deal that was 3x bigger than our usual investments. Using the old approach, we would have passed.

Using the new approach, we mapped out what we brought beyond capital: deep industry relationships from our Goldman days, operational expertise from scaling companies, and brand credibility that could accelerate market entry.

We structured a deal where we contributed 30% of the capital but took a leadership role in operations and strategy. Our network helped close two additional strategic investors. Our expertise helped the company grow 400% faster than projected.

This deal was pretty public and we are under NDA on terms, so I won’t give it all away. But, as you can imagine, we made more money with less capital risk than if we had tried to finance the whole thing ourselves.

Embracing Unlimited Capital

Since that conversation, you'll never hear me say "We can't afford this." We only say "If the opportunity is a good fit for us, you can assume that we have unlimited capital."

Because here's what I learned: at the end of the day, somebody has to do the work. You need competence and effort. That competence and effort can be accelerated by capital, relationships, or brand, but you still need time and skill to win.

If you have those two things, you're never really out of assets to trade.

Now, all you have to do is this: Stop asking "Can I afford this?" Start asking "How can I afford this?" Then inventory your five assets and get to work on the "how."

I hope that this little shift can help you as much as it helped me.