Integrity, raising money and coaching

Many years ago I was invited to Chicago to be a guest at a summit for nonprofit leaders. The summit was hosted at the Kellogg School of Management by the dean, a kind and smart guy.

The summit had an official theme, but the un-official theme was, “how to start running your non-profit more like a smart business so you could get real ish done.”

There were all sorts of great speakers at the event, but one speaker in particular really blew my mind. I don’t remember her name, all I remember is that she played a key roll at one of the largest non-profits in Illinois. For the sake of the story, let’s call her Ms. Amazing.

Now, one of the things that non-profits are always complaining about is money. They don’t have enough and they have a hard time raising it. This is why Ms. Amazing was here. She was the Michael Jordan of raising money, and she was here to school us right.

Her presentation had all sorts of practical gems in it, best practices and whatnot, but it was her closing argument that left us all a little speechless.

Allow me to paraphrase…

“In closing, I want to leave you with something very important to think about when it comes to donations, money and your nonprofit. How could you ever honestly ask someone for a donation if you yourself are not donating to your organization?

The same thing goes for your staff. If they aren’t donating any of their own hard-earned money to the nonprofit, do they have any right to ask others to do so? Sure, maybe un-paid volunteers get a slide because they’re donating their time, but everyone else doesn’t, especially leadership.

It’s not even about the amount of money, it’s about being invested in the idea of what you’re offering and what the nonprofit stands for. If you don’t believe in it with real dollars, why should anyone else?

Before you sit down at your next strategy meeting, before you put together your next marketing plan, ask your team how many of them have actually donated to your organization in the recent months. The answer may surprise you.”

Damn…. Ms. Amazing straight-up gave me the smack down! She didn’t know it, but I was guilty as charged.

Even though I wasn’t a paid staff member of the nonprofit I was with, I was senior leadership. And even though I was volunteering my time, that still didn’t matter. I was asking other people for their money and I wasn’t donating my own.

No wonder we were having a hard time raising money. There was a major disconnect, and my team and I were all part of the problem.

I thought about this story last night when I ran into a friend I hadn’t seen in a while.

My friend just launched this great coaching program for coaches, and it sounded like it was doing really well. The program not only focused on how to be a better coach, but it also focused on how to make a living as a coach.

So I asked my friend more about it and what she thought was one of the major takeaways students got from the course. To my pleasant surprise one of the top takeaways she mentioned was:

“As a coach, how can you ask someone to hire you if you yourself have never hired a coach before? To be a great coach, you need to have gone through the receiving end of the coaching experience.”

So true.

Asking people for a donation, asking people to hire you as a coach, asking people to buy your product, it’s all the same. Either you are energetically in alignment with what you are doing or you are not.

Does this mean my team was magically able to start raising money after we started donating ourselves? Nope. But I seriously doubt we would have made much progress if we didn’t at least start there.

Household name

Most people in the world don’t have an iPhone. Most people have never been to Disneyland, they’ve never seen House of Cards and they don’t know who Bryan Cranston is.

As an entrepreneur, artist or creator, it’s important to remember that even things that we think of as universal, things that we think everyone knows about or has experienced, are not always so.

Starting a new business and money

Starting a new business? Just a couple quick thoughts about business and money…

(1) Do what ever you can to minimize your expenses / lifestyle before you start your business. Cut dinning out, opt for stay cations, cut spending overall. Take the extra cash and build up your emergency fund, Dave Ramsey style.

(2) Do what ever you can to pay off as much debt as possible before you start, especially credit cards. Debt is a huge distraction and will mess with your execution abilities.


(3) Try to cover your base expenses while you are building your business. This one is huge.

Turning a good idea into a great and profitable business takes time.

It takes time to learn the in’s and out’s of marketing, execution, and delegating. It also takes time to learn how to deal with inner demons and the fear and self-doubt they create.

Make sure you give yourself enough time to figure things out both practically and emotionally.

I meet people all the time who had to quit their business early because they ran out of time. Which really means they ran out of money. They set aside money from their savings to start their business, but they ran out of money before the business took off.

If they only had a year or two more time, many of them would have figured things out.

Getting a side gig or part time job can really help give you the time you need to figure things out. All you need to do is make enough money that your most basic expenses are covered. If your base expenses are covered by a side gig, then you’ll have all the time you need to learn, grow and build your business.

I didn’t take this advice when I started my first business, and I paid the price. I took this advice when I started my current business, and it made a huge difference.

Good luck!

Age and comparing

“Who here has ever felt… that they should be further along in life, for the age they’re at?”

A few months ago my buddy Sean Stephenson asked this question to an audience at the Downtown Project in Las Vegas.

The audience was filled with non-profit leaders, best-selling authors, mothers, fathers, wizkids, change agents, multi-millionaires, a billionaire in the making and a princess (for real).

And guess what…

Everyone raised their hand, including me.

Everyone’s felt behind at some point, even the people that seem to have “made it”.

Everyone’s guilty of comparing, no matter how much they’ve accomplished.

That in itself should be a huge relief for all of us.

We’re never going to achieve-our-way-out of feeling empty. We’re never ever going to success-our-way-out of comparing.

There’s no winner in this game. When we play, we all lose. The only alternative is to refuse the play the game in the first place.

When we notice our mind gearing-up, looking for evidence to support our lack, all we can do is pause, take a breath, let it go.

The better we get at catching ourselves playing an un-winnable game, the more focused we can stay on doing the work that matters the most to us, the work that gives us the most joy.

Proving vs Sharing

When you give a talk, and you have something to prove, you end up saying way too much. This is one of the greatest challenges that speakers have.

Anytime I *need* the audience to get something, I come across as scattered or semi-desperate. Almost as if I’m looking to them for the reassurance I’m hoping to find within, which is exactly what proving is.

On the flip side, when I let go of proving and simply share, all the nonsense dissolves.

Sharing is a mindset, a mindset about making the message the primary focus vs the ego of the messenger.

Sharing is what great storytellers do.

Investing in mentors

Think of someone you want to learn from, someone you respect, but don’t know.

How do you show up on their radar? How do you get a bit of their time, council and mentorship so you can grow?

Many years ago I started keeping a list. It was a list of people that I really respected and would love to meet one day.

The list was long and included all sorts of people. Some were famous and some were not. Some names were people that I wanted to have as mentors and some just seemed like fascinating people to hang out with.

Not too long ago this list came up in conversation with a friend. I was telling him about the list and the people on it that have become friends and shaped my life for the better.

After talking about 10 or 20 people on my list that I’ve met, and what I learned from them, my friend stopped me mid-sentence and asked, “But how?”

“But how did you meet them? What did you say to convince them to meet you? How did you get their time?” he wondered.

Lets take your list. Chances are if someone’s name is on your list it means that the person is up to big things.

The thing about people who are up to big things is that they tend to have a lot on their plate. That includes having a lot of people, sometimes hundreds or thousands, all wanting something from them. Everywhere they go someone’s asking for their help, time, or resources.

You could be a great person, a mini-Gandhi in the making, but if you approach them the same way that everyone else does, your voice will get lost in the crowd – the crowd of people who all “want” something from them.

So what’s the alternative?

Every mentor that I’ve ever wanted to meet and learn from has something they care about that isn’t getting much attention or could use some extra support. It could be a little passion project they started or a non-profit they really care about for example. Whatever it is, it’s something that could use a little help, but chances are, most people don’t know about it – it’s under the radar.

Find that thing that they care about and authentically support it. Not as a means to an ends, but because it deserves it. Support it because you respect them and believe in the project. Support it because the project could use your help and your unique skill set.

I know a lot about tech, business, and wellness. I’ve met many people on my list simply by following their work closely and being open to an opportunity to serve authentically with my unique skill set.

One time I sent my favorite author an 15-minute screen cast and design of how he could improve his new community website. It was simple, focused and based on my knowledge with the technology he was using. His new site was also something that I really cared about. He was so appreciative of my suggestions that he wrote me an email saying that he owed me favor, anything I needed.

What did I ask for? Nothing. I simply told him that I respected his work and that he’s made a huge impact in my career. A few months later he checked out my blog and linked to a post he really liked. He also wrote me again and told me to keep in touch. Did I ask him to do this? Nope. Did he do it because he owed me? I highly doubt it. I have a feeling he did it because he dug what I wrote, *and* because I was also on his radar.

As much as this post seems like a recipe it isn’t. It’s actually the anti-recipe. This isn’t a tactic or a game plan. You can’t fake caring. If your mindset is off sooner or later people will smell the fakeness on you and they’ll run in the opposite direction.

I can think of 20 or 30 more stories that played out similarly to the one above. Not because I forced them, but because that’s what happens when you genuinely give a damn.

Everyone wants, few are willing to give. But as my friend Sean Stephenson says, “The more you give, the more you live.”

Giving the right way

I’m featured in my buddy Michael Simmons’s latest Forbes article on the topic of “How Giving In The Right Way Can Transform Your Business”

Here’s a quote from the article on how I did things the wrong way:

“I would take on more things than I could handle because I had a hard time saying ‘no’. I would overextend myself because I was more concerned with how I looked. That brought on a lot of resentment within me for the help I provided others.”

You can read more here.


Some of the traits that made me a lousy manager of a consulting company…

Are some of the same traits responsible for making me a damn good manager of a product company.

Sometimes it’s not about changing or becoming better at something you aren’t good at.

Sometimes it’s simply about finding a different role, vehicle, or medium for the expression of your talents and gifts.

Your reminder, my reminder

Some people grow up ready for business. They start lemonade stands at the age of five and have dreams of being an entrepreneur one day.

I was never that person. I never seriously consider being an entrepreneur until I was in college. And even then my primary motivation wasn’t getting rich or building something new.

My primary motivation was figuring out a way to spend more time with the people I cared about. Business was, and still is, my excuse to hangout with family, friends, and the people I look up to.

Don’t get me wrong, I like being a business man now. I like building new things and helping others. I enjoy talking strategy, creating jobs, creating value, and making the invisible visible. All I’m saying is that it didn’t start that way for me.

I used to have a complex about this, the fact that I didn’t grow up wanting to be an entrepreneur. I felt like I was a fraud, an imposter who would one day be exposed in front of everyone.

When I would make mistakes in business, or when times were tough, I would use it as evidence that I was a joke. When my hard work produced great results, and it was time to celebrate success, I would brush my wins off as pure luck. It was a miserable place to be.

When I share this story with my friends they have a hard time believing me. So many people in my network today think of me as Mr. Business now, even though I have no formal training and I never finished college. But even though they’re surprised, I think a lot of them are also relieved.

They’re relieved the same way that I’m relieved when I hear that my ripped workout buddy was once skinny. Or when an actor I respect told me she still gets major freaking butterflies before the director yells action.

They’re relieved and I’m relieved because these stories are a reminder of a few things we know but often forget.

We don’t have to have it all figured out.

Everyone has insecurities, everyone struggles.

There’s no right background or upbringing.

The only thing that matters is how much you care and if you’re willing to do the work.

When we’re set on finding evidence of how bad we suck, we’ll always find it.

When we let go of the past, and focus on the present, our future can be anything we want it to be.

Here’s your reminder. Here’s my reminder.


A big part of staying focused is remembering. Remembering why we wanted to do, what we wanted to do, in the first place.

It’s in the nature of projects to lose momentum. Highs where off, distractions show up, the going gets though and people (you and me) lose focus.

That’s why remembering is such a powerful practice. It creates an opportunity to regroup, recenter and ask the questions that matter so we can remind ourselves of the answers.

Why did I care about this project? What did I want to accomplish or see through? What was the vision? Do I still care? Is there something I’m afraid of? Even though things are tough, am willing to keep going?

I feel like the people that I look to up to the most are asking themselves some version of these questions all the time. Not once, not twice, but constantly throughout the journey.

You would think asking ourselves the tough questions once would be enough. That somehow our mind would store the answers as fact and keep them on file for future reference. And yet it just doesn’t work that way.

Thoughts of doubt, fear, and worry pile up. They affect us all by creating unnecessary layers. Layers that make it difficult to focus.

Remembering is like digging. The practice of it helps us dig through all the nonsense, all the layers, and arrive on the side of clarity. And when we are clear, focus just happens.