Star Struck

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True story: I just reconnected to a client who I spoke with 6 months ago about helping them scale their startup that was getting a lot of momentum, but they hadn’t done much in terms of figuring out how to build an actual business around their product. They didn’t think to build a team and getting stuff done was going to be a problem, and they didn’t want to invest the time or money to get it right from the start.

“You can google everything and there is so much free information out there, why should I pay for that?," the CEO said to me…

Fast forward, 6 months later…

—They hired 8 people: 3 left after only weeks, 5 are still there but not performing...

How Big of a Check Do You Want to Write to Fear?

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I thought I’d seen it all…

But then I talked to a newer client who was struggling and I wanted to find out what kept him from showing up…

His pain is real:

  • His team was not performing: stuff didn't get done or got done late or badly

  • His NPS had gone way down and customers were dropping off

  • Sales weren't happening as they should and the sales team was becoming more and more entitled

  • The culture felt toxic: backbiting, drama, lots of blaming others

Before he came to us, he’d already done a lot of work and research for how to solve this, but in the end, he kept being stuck on actually EXECUTING on all this stuff. When we started working together the same thing happened. He’d commit to things and then…ghost.

Here is What's Happening

Let’s talk about greatness for a second, because I think you’re destined for it in a way that you can’t even comprehend right now.

Here’s the truth:

  • You could be making millions of dollars that you are LOSING right now

  • You could feel like your business is running like a well-oiled machine where you get to be the rockstar who makes it rain.

  • You could feel like you are on solid ground with a team that gets you and got you…

Fly-by-Night or Built to Last?

Have you ever found yourself fantasizing about what you will do when you can finally sell this monster of a company you are building and you envision yourself on a beach in Mexico or Tahiti for a good portion of the year?

Often disgruntled leaders come to me and all they have in mind is this: how can I get out with the most dollars in my pocket?

While I should stay seriously and ask them some profound questions, this generally just makes me crack up because I KNOW, most of them would be bored stiff after week 2 (IF that long…) and they’d be all in planning their next venture…

Like Pushing A Boulder Up The Hill...

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I just talked to a new client who is super frustrated because she’s been trying EVERYTHING to get her company to take off aaannnnddd… it’s been like pushing a boulder up the hill.

She’s tried a bunch of different ways to address the issues but nothing stuck.

It always feels like she is the only one who sees the problem and is doing something about it. Her team comes to her complaining but they look to her to solve all the issues.

She’s been reading books and watching youtube, but every time she decides to change something all hell breaks loose and she goes right back to the way it was—at least she knows what to expect with the “old problems”...


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Asking good questions will give you a leg up as a leader. The better the questions you ask, the better the outcome of the answers…
The really important questions tend to be one-worders.



However, as it turns out, there is a first question to ask, and it’s the foundation of everything thereafter:


Now you can ask that question simply or you can utilize its many different layers; each of which gets to yet another layer of answers and all of these answers are must-haves to grow your company sustainably.

Get In or Get Out

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This is a sequel to a client story I told you a few weeks ago. The burned out co-founder and CTO. Remember?

This guy is super smart, talented, struggling for 10 years to make his company take off.

Except for, it’s not his company anymore and now the identity that got him through the first ten, tough years--bootstrapping and being scrappy--is the EXACT identity that may cause him to get unseated.

Totally unfair? You bet.

The right move for the health of the company?

It’s complicated, just like anything that balances people and profit.

Conquer The Fear

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I talk to a lot of people every week who sign up for a session with me because they know that their company is not growing the way they want it to and they don’t know how to make it better-- they are stuck.

We really take the time to dig deep and find out what challenges are holding them back from their dream.

And as corny as that sounds if what you are doing is NOT your dream it feels sad for you because that sounds like a lot of time wasted...

So I talk to all these people every week and there is some CRAZY behavior that shows up.

Exponentially Increase Your Income Like This

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One of my startup CEO clients and I have an ongoing argument. What’s more important, product or people? Of course, he’s on the product side, I’m the people person. And here is the cool part: I’m winning!!!  

Actually, I was always winning because no matter what phase of business you are in, people are your most important asset. Who else is going to help you to GET your product to market and who’s going to stick with you through the startup rollercoaster??

Yes, you do need a solid product and however you can get there, get there.  

No More Juice...

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Not sure what’s going on this week but there is a common theme: too many people are burning the candle at both ends for much too long and it’s having serious impact on their performance, their ability to inspire, their level of joy (what’s that??!), their health and quality of life.

If this sounds familiar, pay attention!

One of my VIP clients is the co-founder of a tech startup in NYC. He’s been working on this thing for SEVEN long years and until a few months ago, it wasn’t working at all. The numbers looked terrible. Tons of changes all the time: leadership, team, product, focus… not good.

Delegating is Old News

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You might be surprised, but even some of my 8-figure leaders still have a hard time letting others lead. So often it seems faster and easier to just do it yourself.

But guess what, though it may seem faster and easier to do it yourself right now, guess what that means for the long run?

Exactly, you’ll keep doing way too many things yourself.

And that also means you are NOT doing the things your company really needs you to do, the only things that you should do as the leader: focus on the big picture and lead your leaders.

The Chicken or The Egg?

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I was just reflecting over last week’s challenges and thought I’d share with you what I learned so you can go bigger, better, faster, without reinventing the wheel and making more mistakes than you need to...

There are some scary questions you need to ask if you are getting ready to scale which means heaping a TON of pressure onto your existing setup:

  • What if things are starting to fall through the cracks EVEN MORE?

  • What if we are focusing on the wrong thing?

  • What if our clients get mad because we can’t deliver on time?

Clarity... Completely Overrated.

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So often I talk to CEOs who are really frustrated because it just seems like no matter what they do, they don’t get the performance out of their leaders that they expect.

So I ask: did you actually tell them what your expectations are???

Often times I get a long pause, then there’s some stuttering and sputtering and a long list of indignant excuses that sound somewhat like these:

  • They should know what I need

  • These are C-level people, I expect THEM to grow their organization

  • I thought I wasn’t supposed to micromanage, shouldn’t they know?

  • What am I paying them for

Culture of Discipline

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Just got back after an amazing mastermind meeting discussing leadership and thought I’d share this with you so that you can get a leg up and don’t have to make the same mistakes that I see being made in most young companies (and many well-established ones…)

We specifically talked about having a Culture Of Discipline…

Discipline has certainly gone out of style. It’s just not cool… However, it’s the one thing that can help you turn things around quickly.