Randall Kaplan

Founder of $19b Company AKAM 📈
VC: Google, Lyft, Seagate 🚀
Father of 5 🏡
EXTREME PREPARATION

[Randall Kaplan @RandallKaplan]

I've seen founders lose investors in five minutes.

Not because the idea was bad.

Because they couldn't answer basic questions about unit economics, margins, CAC, LTV, or burn rate.

If you don't know the economics of your business, you're not ready to raise.

Know your numbers cold.

That's Extreme Preparation.

[Randall Kaplan @RandallKaplan]

One photo on Instagram can cost you the job offer.

Before you walk into the interview, someone may have already looked you up.

LinkedIn. Instagram. TikTok.

Your feed is part of your résumé now.

Before you post, ask yourself: Would I be comfortable if my next employer saw this?

That’s Extreme Preparation.

[Randall Kaplan @RandallKaplan]

I ask every founder one simple question:

What was your GAAP net income last year?

99% get it wrong.

“The CFO handles that” is not an answer.

If you don’t know whether your company made or lost real money, you don’t understand your business.

That’s Extreme Preparation.

[Randall Kaplan @RandallKaplan]

Want better results? Add a deadline to every ask.

“Can you get back to me?” creates no urgency.

“Can you get back to me before the end of the day today?” creates clarity, accountability, and action.

Vague asks get ignored. Specific asks get answered.

That’s Extreme Preparation.

[Randall Kaplan @RandallKaplan]

Want better results? Add a deadline to every ask.

“Can you get back to me?” creates no urgency.

“Can you get back to me before the end of the day today?” creates clarity, accountability, and action.

Vague asks get ignored. Specific asks get answered.

That’s Extreme Preparation.

[Randall Kaplan @RandallKaplan]

Most founders start raising too late.

The number is six months.

Start fundraising six months before you run out of money. The absolute latest is four.

Meetings delay. Term sheets take weeks. Due diligence takes longer.

The founders who win are the ones who never negotiate from desperation.

That’s Extreme Preparation.

[Randall Kaplan @RandallKaplan]

A founder says: “I deserve a $60M valuation because another company just raised at $50M.”

That’s not how valuation works.

Different founders.
Different revenue.
Different customers.
Different traction.

Knowing the headline is not knowing the business.

Investors see through that fast.

Valuation isn’t claimed. It’s earned.

That’s Extreme Preparation.

If you're interested in transforming your life and are interested in one-on-one coaching, DM me the word coaching.

[Randall Kaplan @RandallKaplan]

Would you get on a red-eye tonight because a deal was closing?

When we were raising money for Akamai, I told a senior banker: be on a plane today or you’re done.

He got on the plane.

He later became Vice Chairman of Akamai and made over $100M.

Urgency reveals character.

That’s Extreme Preparation

If you're interested in transforming your life and are interested in one-on-one coaching, DM me the word coaching.

[Randall Kaplan @RandallKaplan]

They decided before you walked in.

The recruiter Googled your name, added your city, and scrolled.

The interview was not the first impression. Your feed was.

Most people lose the offer here and never find out why.

The candidates who win do not just scrub their feed.

They weaponize it.

That’s Extreme Preparation.

[Randall Kaplan @RandallKaplan]

You don’t know what good is until you’ve seen enough bad.

Bad hires. Bad deals. Bad advice. Bad “perfect on paper” decisions.

That’s how judgment gets built.

The best instincts aren’t gifted.

They come from paying attention longer.

That’s Extreme Preparation.

[Randall Kaplan @RandallKaplan]

Getting funded doesn’t mean you’ve made it.

For many founders, it’s the moment they start losing.

The best companies are built by people who keep acting like every dollar matters — even when they have money in the bank.

Urgency isn’t a phase.

It’s the strategy.

That’s Extreme Preparation.

[Randall Kaplan @RandallKaplan]

What if you treated yourself like a corporation?

Every serious company has a marketing budget. Do you have one for yourself?

Most people show up, do the work, and hope someone notices.

That’s not strategy. That’s luck.

Bet on yourself. Get in the right rooms. Invest in your growth.

That’s Extreme Preparation.

[Randall Kaplan @RandallKaplan]

Walk in hoping they’ll believe you, and you’ve already lost.

Every room has a silent question underneath the small talk.

It’s not whether they like you.

Charm can’t answer it.

The person who wins does it before they open their mouth.

That’s Extreme Preparation.

[Randall Kaplan @RandallKaplan]

A single post can cost you the job.

Not because you’re unqualified.

Because your online presence told a different story before you ever walked into the room.

Before you apply, ask yourself:

Would I hire the person my profile makes me appear to be?

That’s Extreme Preparation.

[Randall Kaplan @RandallKaplan]

Say “I’m strategic” and you’ve already lost the room.

Nobody writes a check, hands you a promotion, or closes a deal because you used the right adjective.

Don’t describe yourself.

Prove it.

Replace adjectives with evidence.

That’s Extreme Preparation.

[Randall Kaplan @RandallKaplan]

Some words can kill a pitch instantly.

Not because the founder is wrong.

Because the way they say it sends the wrong signal.

The investor smiles, nods, and says, “We’ll be in touch.”

But the decision has already been made.

In fundraising, the framing matters.

That’s Extreme Preparation.

[Randall Kaplan @RandallKaplan]

Four people interviewed for the same job.

Three were smart, qualified, and said everything right.

One candidate won before she spoke.

She did something nobody asked her to do:

She came prepared with proof.

Proof she understood the company.
Proof she understood the role.
Proof she could add value immediately.

Most people prepare to answer questions.

Winners prepare to remove doubt.

That’s Extreme Preparation.

DM me “COACH” if you want one-on-one coaching to perform at the highest level.

[Randall Kaplan @RandallKaplan]

Four words can sink a pitch:

“I ran out of time.”

You think you’re being honest.

The investor hears:
You didn’t prioritize.
You didn’t prepare.
You may run the company the same way.

You never run out of time.

You run out of priority.

That’s Extreme Preparation.

[Randall Kaplan @RandallKaplan]

Most people hear rejection and think it means “quit.”

But rejection is not a diagnosis.

It’s data.

Every “no” is telling you something:

The target may be wrong.
The message may be unclear.
The timing may be off.

High performers don’t just absorb rejection.

They study it.

Rejection is feedback.
Rejection is information.
Rejection is a signal.

The question is not:

“Should I quit?”

The question is:

“What is this rejection actually telling me?”

That’s Extreme Preparation.

[Randall Kaplan @RandallKaplan]

The best CEOs stay reachable.

Elon Musk posted his number on Twitter.
Jeff Bezos answered customer emails himself.
Steve Jobs replied to strangers at midnight.
Why?
Because the higher you rise, the more people protect you from the truth.

Assistants. Gatekeepers. Management layers. Filters.

A leader who cannot be reached is a leader flying blind.

Staying close to the truth is not a risk.

It is the job.

That’s Extreme Preparation.