Introduction:

“Funding is not a growth decision. It’s a risk decision.”
Most entrepreneurs hear “raise capital” and think scale. Expansion. Bigger moves. More visibility.
But what if the real question isn’t how fast can I grow… it’s how much risk am I introducing?
If you’ve ever felt uneasy about taking money — owing someone, giving up equity, reporting to investors, or signing terms you don’t fully understand — you’re not paranoid. You’re picking up on something real.
In this episode of The Strategic Thinkers Podcast, I sat down with Geoffrey Kent, an entrepreneur and strategic advisor who has helped founders navigate funding at every stage. Geoffrey doesn’t glamorize capital. He dissects it. He explains how money helps, how it hurts, and why most entrepreneurs waste months chasing deals that were never going to happen.
This article pulls one powerful thread from our conversation:
Raising money without understanding risk is how businesses quietly collapse.
If you’re considering funding — or deliberately avoiding it — this will change how you think about it.

Real Story (one person, one action, one result)

Geoffrey once watched an entrepreneur burn almost a year chasing capital.
The founder believed funding was the next “growth move.” Revenue was decent. Momentum felt real. So he started pitching.
He built a deck. Took meetings. Refined his pitch. Sat across from investors for months.
Every conversation felt promising.
Every follow-up call sounded encouraging.
But nothing closed.
After months of effort, he still hadn’t secured funding. Meanwhile, competitors moved faster. Customers needed attention. Product updates slowed down.
The problem wasn’t effort.
It wasn’t intelligence.
It wasn’t even the pitch.
The problem was this:
He was talking to people who were never going to do his deal in the first place.
Geoffrey says it plainly:
“The people who get funding match their deal to people predisposed to do that deal.”
This founder was pitching venture capital firms when his business stage required angel investors. He didn’t understand how those investor groups think, what returns they require, or what stage they fund.
So Geoffrey had him do one thing:
Stop pitching.
Instead, study the investor landscape.
Learn what each funding source actually wants. Learn their return expectations. Learn their stage preferences.
One action: Understand the deal before selling the deal.
The result?
He stopped wasting time.
He redirected conversations to the right investor pool.
And instead of chasing 30 meetings that went nowhere, he focused on five that actually fit.
The difference wasn’t confidence.
It was alignment.
And alignment changes everything.

The Truth (why it matters)

Here’s the truth most founders miss:
Funding multiplies whatever foundation you already have — good or bad.
Money does not fix confusion.
It magnifies it.
It does not repair a weak financial model.
It accelerates the consequences of one.
And this is where most entrepreneurs get it wrong.
They think:
● “If I just had more capital…”● “If I could just raise $500K…”● “If someone believed in me…”
But investors don’t fund belief.
They fund return.
Geoffrey makes this clear:
“Rate of return is the first thing an investor cares about.”
Not your logo.Not your passion.Not your vision board.
Return.
And if you don’t understand how they calculate it, you walk into a negotiation blind.

Debt vs. Equity: The Hidden Risk Difference

Most people lump funding together. They shouldn’t.
DebtYou keep ownership.But you owe payments.No cash flow? You’re personally exposed.
EquityNo monthly payments.But you give up ownership and influence.And once equity is gone, you don’t get it back.
That’s not just financial math.
That’s control.
That’s decision-making authority.
That’s future flexibility.
And here’s another layer most founders overlook:
Time risk.
Geoffrey warns about something rarely discussed.
If you spend six months pitching the wrong investors, that’s six months you can’t recover.
In fast-moving markets, that lost time can cost you customers, credibility, and momentum.
He even reframes rejection:
“If they throw your business plan in the trash early, they’re doing you a favor.”
Because an early no saves you from a long illusion.
Funding is not about convincing someone.
It’s about compatibility.

● Are you at the right stage?● Do your numbers justify their expectations?● Can you deliver the return they require?● Do they understand your industry?
If the answer is no to any of those, the deal was never real.
And forcing it only compounds the risk.

What To Do (One Clear Action)

Create an Assumption Page Before You Pitch Anyone
Not a pitch deck.
Not projections.
An assumption page.
Geoffrey teaches founders to document the core assumptions behind their financial model.
Why?
Because financial statements are conclusions.
Assumptions are the logic behind them.
Here’s how to do it:
Write down:1. Your pricing assumptions2. Your customer volume assumptions3. Your hiring assumptions4. Your cost structure assumptions5. Your timeline assumptions
Then ask:● What must be true for these numbers to work?● What happens if one of these is wrong?● Can I defend this assumption in a room of skeptics?
This does two things.
First, it strengthens your model.
Second, it reveals your real funding need.
Because many founders don’t need capital.
They need clarity.
When you understand your assumptions, you can:● See whether debt is realistic.● See whether equity makes sense.● See whether you should delay funding entirely.● See whether crowdfunding fits your stage.
And when you finally sit across from an investor and they flip to your financials first — because they will — you’ll know exactly how you built those numbers.
That changes the entire tone of the room.

Conclusion

Funding is not evil.

And it’s not magic.

It’s leverage.

And leverage magnifies whatever you bring to the table.

Geoffrey put it simply:

“The more you understand how finance works, the stronger you become as an entrepreneur.”

You don’t need an MBA.

But you do need awareness.

You need to understand who you’re talking to, what they want back, and what you’re truly giving up.

Because the real risk isn’t taking money.

The real risk is taking money you don’t fully understand.

And once you structure a bad deal, unwinding it can take years.

So before you raise capital, ask yourself:

Am I chasing growth… or managing risk?

That answer will determine everything.

About the Guest

Geoffrey Kent is an entrepreneur and strategic advisor who helps founders think clearly about business models, funding stages, risk, and long-term outcomes. His approach blends financial literacy with practical entrepreneurial experience, helping business owners match their deal to the right investor at the right time. He is also the creator of Entrepreneur Academy, a mentoring community built for founders who want clarity before scaling.

Connect:
Website – www.thinkbigwithjeffreykent.com

Entrepreneur Academy – https://hi.volley.app/land?tk=KAyRbBp2hgYuCMVbwyqDcW-tk

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