Sharing the cheat codes in startups and life!

This is what the O’Daily is all about.

Why should you learn things the hard way when I’ve already done that???? 😂😂😂

I started with 6 things I’ve seen wildly successful folks do over and over again.

And I realized…THERE’S MORE!

Here are 3 more things that highly successful business people do…and now you can too!

1. Practice a personal elevator pitch.

For me, this falls into the annoying-but-necessary category.

Don’t hate the player, baby, hate the game!

There is an art to a non-cringey, humblebrag.

Great sales people and CEOs are usually really, really good at a one-line drumroll to make something or someone sound awesome.

(Including themselves. 😉)

In almost every call, meeting, or networking event, you will get asked about yourself.

It’s your chance to establish your credibility, give background, and (ideally!) make someone laugh or lean in for a follow up question.

DO NOT GIVE DISCLAIMERS OR UNDERSELL IT.

The most successful business people have a short, awesome, funny way they describe themselves and their career.

If you ever meet Kara Brown, hers is genius.

Christine de Wendel’s is also excellent.

Mine is…decent. I consulted with an expert (my husband) to improve it.

Sharing as an example, not the ideal. 😉

Less than 10 words: Startup COO turned VC. 7x Ironman. Mom of 2.

One sentence: I’ve been scaling startups for 15 years, as a customer leader and COO, with multiple exits to public companies. (Insert joke about switching to the dark side as an investor.)

And I always say my title!

Yes, of course, there’s a hundred details and caveats. Everyone's career is more than one sentence.

Doesn’t matter. No one cares. They can ask about details later.

It’s like a company pitch. Make it short and easy to remember. Tell the BEST version (no lying though!).

You would never say, “We’re an AI platform that’s doing fine but not great and let me show you every feature and explain the pros/cons for at least 15 minutes.”

Yet that’s sometimes what people do with their personal pitch.

Why don’t people have a personal elevator pitch?

It feels awkward! Egotistical even.

But you are telling your story either way. Make sure it’s the one you want.

Practice, iterate, read the audience, try out new stuff, and find that A+ personal elevator pitch!

2. Ask for a big title.

I love helping other people succeed.

As COO, team manager, customer success manager, and, now as an investor, if I do my job well, I’m in the background and someone else shines.

Me and Jason Bourne = you’d never know we were there!

I love helping other people succeed, but it poses a challenge (see Personal Elevator Pitch above):

How do I convey that I’m good if the whole point is to make someone else look good? You don’t want to undermine someone and take credit.

I asked someone in a similar role and she shared wisdom that changed my life:

Get the biggest title you can.

Yes, you have to deserve the title. You can’t (often 😉) go from intern to VP Sales in one move.

But when you have a big title, especially in supporting roles, you don’t have to constantly explain your value. The title says it for you.

When “VP of Operations” was proposed as my promotion, I said, “I’d like to be COO.”

“Okay, sounds good,” was the response.

It was that quick, simple, and made all the difference.

BONUS: This can also be used customer-facing. Give your team meaningful titles to provide instant credibility with customers, especially if they are younger or the company is starting out.

3. Always negotiate.

“But I don’t like negotiating.”

That’s what I told Adam Blitzer when I shared the job offer I was considering and he asked if I had negotiated.

He told me something that changed my life:

“Always negotiate.”

Then what really blew my mind:

“I don’t like negotiating either.”

Whaaaaa?

Adam was the guy asking for discounts on conference booths, vendor contracts, or brokering a $95M bootstrapped exit.

Adam was the co-founder at Pardot, an executive at Salesforce, is now the Datadog COO.

The dude can negotiate and seemed to enjoy it.

Young, foolish Kathryn thought the only people negotiating were those who loved it.

(And continuing the narrative in my head — those who loved it were mostly men and it came easy to them.)

FALSE.

Negotiating a contract, job offer, business transaction, or anything really — is one of the most meaningful things you can do for yourself and your company.

The stress is high but the time required is small and the impact lasts for months and years.

Top business people ALWAYS negotiate. They expect you to negotiate too.

And — surprise — it gets easier with practice.

Don’t love negotiating? Do it anyway! 😉

What’s your personal elevator pitch?? What other tips have you picked up from successful business leaders? Do you agree with these learnings?