Kass and Mike Lazerow on Why Building Big Requires Feeling Deep | EP 620

Why choose a sleep number smart bed?

Can I make my site softer?

Can I make my site firmer?

Can we sleep cooler?

Sleep number does that, cools up to eight times faster, and lets you choose your ideal comfort on either side, your sleep number setting.

It's the sleep number biggest sale of the year.

All beds on sale, up to 50% off the limited edition smart bed, limited time.

All sleep number smart beds offer temperature solutions for your best sleep.

Check it out at a sleep number store or sleepnumber.com today.

Support for this podcast comes from Progressive, America's number one motorcycle insurer.

Did you know riders who switch and save with Progressive save nearly $180 per year?

That's a whole new pair of riding gloves and more.

Quote today.

Progressive Casualty Insurance Company and Affiliates.

National average 12-month savings of $178 by new customers surveyed who saved with Progressive between October 2022 and September 2023.

Potential savings will vary.

Coming up next on Passion Struck.

I think the ego happens a lot.

It comes forward.

And I think a lot of founders get blinded by their ego and pride.

And we see this a lot when things aren't working.

So let's just say a founder has told us that X, Y, and Z need to happen this year, and that's their plan.

And when there's enough data that they're looking for, they're looking at that basically says none of it's working, that's when the ego gets in the way.

You start to see them trying to convince themselves that they shouldn't pivot or that something's not working because they tell themselves stories and those stories are attached to their ego.

Welcome to Passion Struck.

Hi, I'm your host, John R.

Miles, and on the show, we decipher the secrets, tips, and guidance of the world's most inspiring people and turn their wisdom into practical advice for you and those around you.

Our mission is to help you unlock the power of intentionality so that you can become the best version of yourself.

If you're new to the show, I offer advice and answer listener questions on Fridays.

We have long form interviews the rest of the week with guests ranging from astronauts to authors, CEOs, creators, innovators, scientists, military leaders, visionaries, and athletes.

Now, let's go out there and become Passion Struck.

Hey, Passion Struck fam.

Welcome to episode 620.

I'm your host, John Miles.

This is a space for the curious, the courageous, the ones building lives that aren't just impressive on paper, but aligned in spirit.

A community of seekers, builders, and change makers who believe that impact starts with integrity and that meaning isn't something you stumble into.

It's something you create on purpose.

If you've been here a while, thank you.

Your presence, your questions, and your willingness to grow out loud.

That's what keeps this movement alive.

Before we jump in, a quick heads up.

Our new new sub stack, The Ignited Life, is growing fast.

Every week I share stories, strategies, and behind-the-scenes tools that go deeper than the podcast.

I also give discussion guides and workbooks that go along with each of the episodes.

It's also where I process in real time through notes that I send out daily and where our new passion struck merchandise line has just dropped.

The gear is bold, intentional, and rooted in one core idea.

What you wear should reflect what you believe.

Think a hoodie that says live like you matter.

A hat that reminds you to own your own spark.

And to celebrate, we're running a launch giveaway.

Just head to theignitedlife.net and join our ignition room to enter.

All right, let's talk about today.

We're continuing our new series on the connected life, a deep dive into how we build trust, navigate hard conversations, and show up more human in every part of our lives.

Last week, I talked to Dr.

Andrew Brodsky about the hidden dynamics of virtual communication.

Then, on Tuesday in episode 619, the legendary John Cabot-Zinn joined me for one of the most powerful conversations I've ever had on the role of presence in modern life.

And today, we're taking this one even deeper.

Because if you've ever looked at someone's success and thought, how do they do it all?

This episode is for you.

My guests today are Cass and Mike Lazaro, serial entrepreneurs, early investors in Liquid Death and Scoplay, and authors of the brutally honest new book, Shoveling Shit, a love story about the entrepreneur's messy path to success.

They have built and sold multiple companies, including Buddy Media, which they sold to Salesforce for a whopping $745 million.

They've worked alongside Gary Vaynerchuk.

They've raised three kids, and they've done it all as business partners, co-founders, and spouses.

And they're not here to sugarcoat the journey.

In this episode, we unpack the myth of the overnight success and the story of what actually happened the day everything fell apart.

Why the most important decisions in business might be who you build it with.

We go into the emotional cost of high performance and how they stay together through the chaos.

We dive into how to hire well, lead with values, and build a culture that doesn't collapse under pressure.

And lastly, we discuss the one mental shift that could save you from burnout and bitterness.

This conversation is smart, unfiltered, and refreshingly funny.

But more than that, it's real.

It's a reminder that success without self-awareness is a fast track to self-destruction.

And that the real story, the one that's worth telling, isn't about the exits.

It's about the mess in the middle.

So let's dive into episode 620 of Passion Struck with Cass and Mike Lazaro.

Thank you for choosing Passion Struck and choosing me to be your host and guide on your journey to creating an intentional life.

Now, let that journey begin.

I am so honored today to have Cass and Mike Lazaro on Passion Struck, two of my favorite entrepreneurs.

Welcome, Cass and Mike.

Thanks so much for having us, John.

Thank you.

We appreciate it.

I don't do a lot of inbound guests on the show, but when the team approached me about having you on, since I've known your story and followed it for 20 years, I thought it was such a great one because it combines an entrepreneurial journey with a love story that coincides around forming companies around life events.

Who can refuse a story like this?

But the reason we're here, and I'm going to show this book and I put it back together so it looks like my view, but it's called Shoveling Shit.

And I love it because not only is there a shovel on the cover, for those who can't see this, the way I i got the book because it was an advanced copy i also got this little piece of plastic shovel that i'm holding up right now so great packaging on this book i wanted to start out with what is the significance of the shovel why that metaphor

both of us feel john that as an entrepreneur it's not always glamorous and it's not full of glory There are times often throughout the day that you're going to get punched in the face and you just got to start shoveling your way out of whatever mini crisis or mini failure that you're having.

And we liken this whole experience of being an entrepreneur to golf, right?

You pretty much hit really awful shots until you have one really good one that keeps you going.

So we thought this metaphor was perfect for an entrepreneur and that's why we included shovels.

What has been one of my favorite interviews that I've done on the podcast is Sean Foley.

Do you know who Sean is?

Yeah.

I knew who he was and I knew who he had coached, but I didn't know the person behind the name and the coaching until I started to really study him.

And man, we were going deep into Malcolm X and Buddhist principles and a lot of things.

So who was the coach for the Chicago Bulls for so long and then the Lakers?

Jackson.

Yeah, he's like the Phil Jackson of golf.

I love it.

He's like the Zen master who makes you think about more than just golf.

Absolutely.

Since we're talking about golf,

can you take me back to the call that changed everything with Chip Shot?

What did that moment reveal about the reality of startup life?

So it was, we started the company, we started golf.com because I had a dream to help recreational golfers track and analyze their game online, be able to get scores on leaderboards of all the tournaments going around and book tea times and really get an official USJA handicap.

So we started this in 1998 in the fall.

And by December 99, during the dot-com boom, we were acquired by chipshot.com.

And they were going public.

So they told us they were Sequoia-backed and they had all their paperwork ready for filing their S1 to go public in the spring.

In March of 2000, just when everything was crashing in the dot-com era, we got a call from the CEO that told us that Sequoia had backed out.

They were out out of money and they were going bankrupt and pulling us back in.

Talk about a real punch in the face and wishing we could take a mulligan if we're going to keep using like golf terminology here.

It teaches you a lot of resilience.

I think Mike and I would say that we learned the most from golf.com and that failure right there.

Personally, I replayed in my head over and over again, like due diligence, what did I miss?

The relationships.

And I just kept going back and back into my mind, trying to remember anything that I could have missed.

But it really is being an entrepreneur is a test of your grit and your ability to endure suffering.

I

started my entrepreneurial journey when I was in my late 20s and I did it a little bit differently.

I started a startup within what's now Accenture for high growth mid-market companies, And I convinced our leadership to start going to these startups and discounting our rates somewhere between 50 to 75 percent.

And then we would take an equity position.

But what I found pretty early on, so we were the precursors for what now is fractional executives, that whole market.

But I found it was very difficult to find and

because there were so many startups at the time to find the right ones.

So I started partnering with the venture capital firms, of which Sequoia was one of them.

So I've known Don Valentine for, I don't know, 25, since 1999.

And I've seen what happened to you guys play out so many times on this journey.

And I don't know if you ever heard of a company called Wyclip out of Austin.

But this was a Sequoia-backed company and they were revolutionizing the way that you would interact with getting a coupon.

And they were using geofencing way before anyone else.

So let's just say you're walking by Chili's and it would geofence you to them, it would serve up a coupon and they ended up doing a deal with DoubleClick and DoubleClick wanted them out of the market.

So they got acquired and the next day they were out of business with nothing they could do about it.

How do you recover from something like that?

Because I remember just sitting with the founders at that time of YCLIP and they were just devastated and didn't know what to do.

So how you recover is how you do everything as an entrepreneur.

You show up to work and the proverbial, you know what, hits the fan and you just got to start shoveling.

You never know what clients are going to churn and leave you, what employees are going to try to quit.

Do you get sued?

All of this stuff that we've all dealt with, that happens to be a big pile that you need to recover from.

And I remember thinking, First, wow, like I can't believe we thought that we're really rich on paper.

And then now that a company's going bankrupt, we have to buy it back.

And then once we understood what was going on, we're out of the shock, right?

You hear news like this and you're just in shock.

It's basically, what do we have to do to win?

So what do we have to do to buy it back?

And in that case, we needed to raise money.

So we hit the road with our third co-founder.

We didn't even have a bank account.

We had very little money personally.

We went to the Bay Area.

All three of us slept in the same hotel room.

I don't know if our co-founder, Mike Casper, had that in mind when we decided to start the company together.

And then we went to New York and did the same thing on Aunt Boo's couch and her pull-out Murphy bed that came out of the wall of this 800 square foot apartment with the two of us in one bed and Mike Casper on the couch.

And what we had done is we were transparent with our employees the whole time.

We didn't hide this, right?

As soon as we got the news, we got everyone together.

We said, listen, there's nothing about what we're about to say that is good.

So this is news that we just heard.

We are empowering you with it.

We're going to be fully transparent.

And they stuck with us for three months while we raised the money.

They went without pay.

We then did back pay.

We grew that business, sold it for $25 million in 2005 to Time Warner, which is how we got to New York, which then led to our next ventures and eight in total.

And entrepreneurs are entrepreneurs.

You get up, the sun rises, you shovel, the sun goes down, you shovel a little more while it's dark, and then you get up and do it again.

One of the things I have found through my own journey of working with a lot of startup founders is that a lot of them have pretty high egos when it,

to put it lightly.

And

I think the ego plays a very significant role in founder decision making.

How How have you found or coached other founders to keep it in check?

Or do you keep it in check?

What's your advice on that?

I couldn't agree more with you, John.

I think the ego happens a lot.

It comes forward.

And I think a lot of founders get blinded by their ego and pride.

And we see this a lot when things aren't working.

So let's just say a founder has told us that X, Y, and Z need to happen this year and that's their plan.

And when there's enough data that they're looking for, they're looking at that basically says none of it's working, that's when the ego gets in the way.

You start to see them trying to convince themselves that they shouldn't pivot or that something's not working because they tell themselves stories.

And those stories are attached to their ego.

Mike always says, being an entrepreneur is giving people a front row seat to your failures, right?

Because it's hard to have the wins.

And that's where we think that the ego gets stuck.

I remember I was listening to an interview that you guys did at South by Southwest.

And you were talking about a moment with board members where you brought on a board member who asked you, what do your profits look like?

And at first,

Cass, you started or Mike started to answer.

And then he said, I'll turn it over to Cass.

And then this board member who was part of a hedge fund.

starts screaming.

What was he screaming?

And why was that so important?

He slammed his hand on the desk, which back then we didn't have FaceTime or Zoom or anything like that.

So we could hear the actual hand hitting the desk and yelled at us, don't shine the turd.

And it was a lesson for us in that ego has to be put aside.

You can't tell yourself stories to make up what the data is actually saying.

And our sales were okay, not great.

But we had this story.

They're good.

We're getting there.

And that we have taken care forward with us for every single investment, every single person that we can tell that story to.

And it has served us really well.

Absolutely, because what I have learned through the board meetings I've been in, and man, I've got a doozy for you.

I joined this company originally as the president.

It was a software company, and the board felt like the CFO and the CEO weren't being truthful to them.

And so they brought me in under the covers of being a president to figure out what was going on.

And I quickly learned that the two of them were using the expense accounts to basically live their life style.

They were, they both had bought BMWs off the company, apartments, condos,

and then on top of that were completely inflating the revenues of the company by about 40%.

And having to navigate how you tell the board that while you're then asked to take over becoming the CEO and trying to work with that CEO and CFO, while then the board decides to sue them in the middle of it.

So I have been through the ringer of these things.

And what I learned from it is what you were just describing is the more transparent you can be, the more your board is going to help you.

And there's nothing worse than having a board that has to react at the last minute to try to salvage something that they could have gotten ahead of way far in the future.

So what would be along these lines, your biggest bit of advice that you could give a founder or a startup on how they should pick their board and how they should treat them?

We look at raising money and managing a board as managing any relationship that's important to you.

When you show up to raise money, ideally you have provided some value beforehand.

You have a relationship.

They know who you are.

They have a sense of your credentials, meaning who do you surround yourself?

What have you done?

Investors don't really care where you went to school.

They care about what you've done and who you've worked with, obviously, whether you've won or not.

And so if we look at our most transformative fundraisings and board members, these are people who we built relationships with in many cases over many years.

People like Howard Lindzen, early stage investor and roger aaronberg the soft bank team who was based in new york at the time graycroft these are firms and individuals who knew us and so by the time we we showed up to pitch an investment they were at least wanted to lean in not necessarily do the deal and way too many founders and really way too many business people look at everything as transactional.

So what can they do for me we always ask what can we do for you and that has gotten us so much more in return i think than we've ever given even though we've given a lot but if you have a give mentality which you've talked about the rest takes care of itself

Well, it absolutely does.

And you two now have a ton of experience of being on boards because you've invested in over 100 companies.

So you bring some very valuable insights from that.

And one of the things I wanted to ask along those lines is one of the most powerful lines in the book I thought was, it's inside their struggles that entrepreneurs often find their reward.

Can you, one of you, take us inside a moment where that was especially true for you?

Mike, do you want to go?

Yes.

So the whole idea behind the book, Shoveling Shit, a Love Story, is not that it's just miserable and suffering, which it is.

Starting a company is lonely, a lot of work.

If you just want an easy day, just get a job, sit down from nine to five, do something, go home, you could leave it at work.

Entrepreneurs don't leave it at work.

At the same time,

there is purpose that is found in work.

So hard work is a virtue.

Those of us who are lucky enough to start companies

really find the path they're supposed to be on and wake up fired up.

And

that's really what we tried to capture.

And when we look at our

experiences, it's in the trenches with our teams during the hardest times where we grew the most, we learned the most, and I think built the closest relationships.

And I think where that was most

apparent to me, the specific was when I walked on the stage in, you know, the day we announced the sale of Buddy media for 745 million to salesforce i walked on this stage i look out this ballroom all of our employees are there and i felt beat up i was 40 pounds overweight this company that went from zero to 50 million in annual recurring revenue in three years from launching the product to when we sold it had just taken a toll And at the same time, I felt like you feel

at the end of a long run or something that is just physically drains you, there's a sense of purpose and accomplishment.

And I had to hold this idea that I'm miserable.

So my cardiologist had told me I'm going to die if I don't have an artificial heart valve.

So I was not doing well personally.

And it was awesome because we had done it.

Right.

And so that was one that captured the suffering and the epic accomplishment all in one day.

I want to get back to this whole journey with Salesforce in a second, but I just want to ask a follow-up question because I think what you just talked about about burnout is important because I found myself almost in the same spot that you did.

I had found myself overweight, not in great health, not in great mental health.

I was trying to put on a great face at work, but behind the scenes, I was anything but doing well.

And in the book, there's this line, the relationship with hard work from a pit of deep uncertainty lives in the heart, not the head.

But there's a cost to that heart-driven work.

And so my question is, how do you protect yourself from burnout, which

as you went through and I went through, is so easy to find yourself on the path to experiencing?

I think we did a better job

these last, I would say, 15 years than we did the first 15 years of working together.

And we've learned some rules and cheat codes over the way.

We talk about it in the book.

But part of that is you have to prioritize your health so that you actually can function, right?

But you have to put it on the calendar.

And whatever that is, it could be like for me, a lot of it is non-negotiable workouts and also just quiet time, like no other, no talking, nothing, just quiet time.

And burnout's a real thing with entrepreneurs.

And it's like Mike said, it's very lonely.

It's also, you have to have really thick skin because things happen so much, and there's so much criticism and feedback that's going to be coming your way from people who think they're being helpful.

But you have to be able to start to realize that the doubts that you have to be able to put those aside and have the discipline of your brain to say, I'm going to keep focusing on those big rock priorities.

And that mental discipline is what creates the burnout in my opinion because you've basically been holding your breath for however many years and you get to some kind of finish line and then you just feel exhausted so our rule of thumb is prioritize something for yourself at least 45 minutes a day

And that could be as simple as taking a walk, taking breaks, doing a short workout.

One of our new friends says it's coffee with her dogs in silence.

Just, that's what it is.

It has to be prioritized.

Well, thank you for sharing that.

And I wanted to go back to this journey because

I understand the whole thing started in a hospital room where Cass, you were giving birth, I think, to your third child.

And I know you have a child named Miles.

So I love that.

You love that name spelled differently.

But so you're, you had just had a C-section, you're recovering, and

you think mike is going to bring you some cuisine to help you get over the surgery and instead he has another passion that he wants to talk about how do i how did that all play out

Well, I was used to his ideas coming out at any time or any place.

That is something that I've always been used to with Mike.

And that starts from the minute he wakes up to the minute he goes to sleep.

He will say, I have an idea.

i had thought maybe it just wouldn't have come out while i was in the recovery room with our third child but he i'll let mike tell it he was saw this big announcement from facebook and he could he just couldn't help himself

so at the time i was on my blackberry and Cass was in surgery having, it was a C-section, not much for dad to do.

So I'm sitting there and I read the story about Mark Zuckerberg.

And he stands up at F8, which is developer platform, is developer conference, and he puts out a call for all developers to build the next generation of applications with deep integration into Facebook and the social graph.

Zuck basically said, here is the virtual representation of real-life relationships.

You can use it to make your apps better.

For example, if you are building games, users can play games with their friends just by hooking it up to Facebook, right?

You could invite friends and that's how Zingo is born.

If you're a marketer, you could build apps that do fun things that enable friends to communicate.

FedEx launched a gifting application with us.

But at the time, I just thought it was a big idea.

And I get very excited.

Let's just say that.

And I probably shouldn't have brought it up, but she gets wheeled into the waiting room.

And I say, Cass, I got it.

I got our next.

And she's got what?

She's groggy.

I'll never forget this.

Our next business idea.

and she basically gave me a look which was communicating four letter words i'm not going to say i'm such a great program but you know three months later she was sitting in an office at the corner of 60th at columbus building desks and buddy media was off and running

i just wanted to use this point of how did your path intersect with Gary Vaynerchuk, who wrote your foreword?

Because I understand as you were starting in the midst of starting this company, he was also starting Vayner Media and you were cohabiting for a period of time, if I understand the journey correctly.

Exactly right.

And we're talking earlier about giving and we love entrepreneurs.

And

we get a call from this guy who I knew because he had a wine show.

I don't drink wine, but it was like one of the first YouTube shows on wine.

And he basically said, I've been working for my dad since I was like 13.

I've never made more than 100 grand.

I'm 34 years old.

I have a concept for a new type of ad agency that helps companies market the way I've marketed at my wine company, Wine Library.

Problem is, I don't have any money for an office.

Can I use your only conference room as my office?

Now we're in like a thousand square foot max.

He's asking for 250 square feet and the only like private room.

I say yes immediately, but I say, yeah, you got to talk to this lady over here who's my partner in all things.

And I thought Cass was going to say no to Gary.

Those of you who know Gary know that you can't say no to Gary.

And he has a gift of gab, unlike anyone else.

He's great with people.

And Cass said yes.

And he has been one of our closest friends.

And I would say mutual mentors.

We come to each other whenever we need really

help.

So we own a pickleball team together.

We are investors in VFriends.

We did Empathy Wine, his wine company together.

I'm a very large collector of VFriends.

He was involved with Buddy Media.

Obviously, we worked on clients together.

And everything in life, the more you give, the more you get.

And we had no idea that he would build a 3,000 person, half a billion dollar empire, a a half billion dollar revenue empire out of that little conference room but there's no better entrepreneur that i know and the main reason i say that is unlike cass and myself we raised money from venture capitalists to build software and then sell it gary self-funds all of his businesses and he uses revenue to grow the businesses, which is really the best way to fund businesses.

No, it absolutely is.

And I want to ask you another question about V-Friends, but I love here you love that, Gary.

I have, for those of you who are listening, I have a copy of Gary Vee's Meet Me in the Middle children's book, which I interviewed him about.

But what got you guys, besides Gary being very difficult to say no to, one of these days he's going to wear down the jets enough to buy him.

But exactly.

What excited you so much about his V-Friends concept?

So the V-Friends VFriends concept came down to one thing for me, which is

intellectual property is one of the most powerful businesses and forces in the world.

We have an incredible system in the United States to protect IP, copyright trademark.

And if you look at the last generation of what

took off, a lot of it was based on IP that people traded, people played with.

So I went back to Teenage Mutant Ninja Turtles.

It's still a billion dollar franchise.

And there's no one better at building businesses than Gary.

And so we bet on Gary.

We bet on the market, which is

hundreds of billions of dollars in kind of IP-based revenue.

And the rest is history.

And he's had three great events.

He's gone incredibly deep into trading cards, which is the latest.

And so the NFTs that launched this all was a way to build the community.

But Gary has gone way beyond just digital collectibles.

It's one of the communities that I love the most because it's so positive in a world in which we need positivity.

He espouses empathy and listening and patience.

And the world is short on a lot of that stuff.

Well, that was one of the reasons I was so excited to do the interview because he and I both share, I think, a common belief that kids are not learning the right value systems today.

And you need to get to them at the right age point.

So I also have a series of 10 children's books coming out.

The first one will come out in December.

A little bit different than his, minus centered on getting kids to understand that they matter and that they hold significance and why.

But both of them.

Yeah, both of them really are on this cornerstone of teaching the right value system to kids from an early age, because oftentimes it's not getting reinforced in school nor in their family situations.

And we've thought about this a lot.

We have three kids and they're now entering.

One's entering the workforce, two in college as of this fall.

And there's a huge gap between what they're learning and what they need to be prepared for in this new world.

that we live.

And so we just believe that all kids are born creative.

They're born as entrepreneurs anyone who's had a baby knows that baby does whatever it can to get what it needs now whatever it can in that case is crying but talk about advocating for him or herself they come out advocating right

and weaponizing their voices to get what they want

and and then they go through this industrial normalization complex right they go to school and they're told to sit down and shut up and memorize these things and be a little kid and yeah and that creates then you add social media where i'm not as good enough in my mind as everyone else and no matter how what age you are and you have this toxic brew that creates kids that are both ill-prepared for the world and lack confidence and don't think that they're enough in and of themselves we spoke about ego earlier and there's no doubt that entrepreneurs have ego and they need ego, right?

That's the rocket fuel

for them to be able to have the unshakable confidence, the vision, the charisma to do what they do.

But pregnant in that ego is the wrecking ball for the company and for your life, right?

Inside that ego is also why we ignore feedback, refuse to pivot, hire the wrong people, build a toxic culture, micromanage people.

Like, don't get me started, right?

And so

kids are now coming into the world with very little confidence

they don't have that ego which is necessary to say

I don't need external validation to do what I want to do I am enough

I have everything I need inside me and that is creating issues across the board as we spend a lot of our time with young people.

We love it.

It keeps us young.

Thanks for sharing sharing that.

And my kids are about the same age as yours.

I have a son who is 26 and a daughter who's a senior in college.

So I get this.

And I'm also close to my nieces and nephews.

So I'm hearing the struggles that they're going through as gen alphas, which I thought the Gen Z's

were going to be the end of this, but the parents lack I guess the way I like to phrase it is if a child needs to feel like they matter and that

they feel significant and that

their values matter to the world, it gets most reinforced by the parents.

But if the parents are checked out and they're disengaged and they're not feeling all of that, it's almost impossible for them to give it to the kids.

And so you've got this loop now that's happening.

that we as a society just can't seem to break out of.

And that's where a lot of my focus is going.

And also the focus of a lot of parents that are helicoptering and just doing everything for them.

I think the other part of the confidence issue is we don't let kids fail safely when we have 18 years to let them pretty much fail safely, right?

If not 22.

And we're just not letting them make the mistakes, letting themselves pick themselves up so that they learn that you can learn things from failure.

I think that's the other part of it.

I think that's such an important point, Cass, because that's the parenting philosophy that we used for the kids as well, because I'd much rather have them make a mistake before they're 18 where it doesn't really cost them too much.

When you start making mistakes as an adult, it starts really costing you a lot.

Yes, exactly.

So I want to go back to this journey with Salesforce because this story involves a lot of characters that I know personally.

and not as well as you do but i know them and so i love this story because you're at a point now where you are trying to hire a president to run the company and you shoot really big.

You go for Susan St.

Ledger, who at the time, I think would have been like the EVP of sales.

And I had known her since she was a VP, but she was like Mark's right-hand person and she was climbing up the ladder very quickly.

I guess there's two things I wanted to ask you.

If you're a founder, how do you get the courage to ask big?

Because Susan Susan was a big

ask and then how did you convince her to come over would be the second part of the question.

It first starts off with when you start your company right and you

have your vision most investors are going to ask when they're thinking about investing in you, what's your exit strategy, right?

Who do you think could either acquire you and could you go public, things like that?

We always were watching Salesforce and Mike did such a great job with getting our name out there and really building relationships with so many different investors, whether they invested in us or not.

But when we thought about how to get bigger and you look at all that Mark's done, we really wanted to start to

replicate his formula for success when it came to sales.

So when I thought about it, I was like, okay, I would love to get Susan St.

Ledger here.

She's just fantastic.

And it was a big lift.

I will tell you that.

If you see me right now, I'm in a t-shirt.

And perhaps you know this, John.

Susan does not wear t-shirts unless she's playing basketball.

So no, she is always dressed to the nines.

To the nines.

And during that era, she had, I just remember she had Chanel cuffs on both wrists.

She just looked fantastic.

So the first step was for me to learn how to dress up a little bit to get to her level.

And then it was a series of Mike and I dating her literally getting to know her flying out there to meet her having conversations asking her what her career goals were and then aligning all of our interests and I don't know how many meetings do you think we had Mike what do you think so many so many

I don't know, 10, 15 different meetings.

I was going back and forth across the country multiple times every couple weeks just to keep talking to her.

And I think I got the confidence because we were at a point where when you're at 50 million in ARR

after three years

and you're basically projecting to double it, you need to have professional help when it comes to sales.

And she was what was going to be that professional help.

Well, I think in the long run, it gave you a very trusted person when Salesforce or someone else was going to make the acquisition That brought in a really heavy hitter.

It validated us.

She was a transformative hire.

But looking back, I think the biggest lesson for us is Suncast says over and over again, know what you don't know.

So we got it to 50 billion in sales.

We'd never done this before.

We called it buddy media because we thought it was going to be a media company.

We then pivoted three times into software.

You don't call a company buddy media if you're a software company, right?

And so then we find ourselves like, how do we scale sales?

We had 40 salespeople.

Mark would later tell me at his house that we made a mistake.

We should have had 400 because we were selling it so effectively.

And

the bringing Susan on board and a public company CFO just helped bring to the company skill sets we didn't have.

And that's really your job as a leader to bring people in who make you better and not like intimidate them or be intimidated by them or make their life harder.

You have to be humble enough.

And again, this is where you might say ego comes into place to say, this is not what we did best.

I remember Mike and Jeff Ragovan telling me the story of the first meeting with Susan.

And she kept asking them, well, why are you doing it this way?

Mike just kept saying, that's how we know to do it.

And she's, well, that's the wrong way.

And he's, okay, let's fix it.

Great.

Okay.

Awesome.

That's why you're here.

So I have a Mark Benioff story.

But first, I've got a bunch of Mark Benioff stories.

But first, I wanted to ask you a question about him.

So for those who don't know who Mark Benioff is, he's the founder and CEO of Salesforce.

He also happens to be a huge fan of Star Wars.

Like such a big fan that he named his daughter, Aleia.

I have to ask, when you walk into his actual house, because I haven't been there, is it all still

Star Wars characters throughout it?

At the time, he lived in a neighborhood of San Francisco, very nice neighborhood, and he had two townhouses that backed up to each other.

If you think of a block, a square block, he had two townhouses on two different streets that backed up to each other.

And he had a courtyard in between.

In one of the houses was his residence.

So his young kids at the time and Lynn and where where he lived.

The other housed his philanthropy and was his office, his home office, very large home office.

Also had a gym.

When I walked in, Mark had just finished working out.

He was still sweating, hat on backwards, eating at a power bar, some sort of energy bar.

And it was a very casual meeting between two entrepreneurs.

He loves entrepreneurs.

He wanted, his first question was, show me the product.

I pulled up the product, just started demoing it.

He gets very excited like I do.

And he just kept, and I had

a demo that basically targeted ads based on circling a geographic area and showing how we publish content.

And it was slick.

And he was just blown over.

We negotiated the deal on the spot.

He said, I'll pay this for the business, no more.

Got to go to the board, all that stuff.

I said, I got to talk to my investors and CAS.

I can't agree to anything, but please just put your best foot forward.

I'd love to work with you.

We've modeled the business off of Salesforce and what you've done.

And it was one of the best meetings of my life.

And to this day, I have huge admiration and love Mark.

I mean, we will both admit he overpaid for the business.

I love him not just because he overpaid, even though I appreciate that, Mark.

How he operates

is phenomenal.

He has a saying, just do the right thing.

So what is the, you ask him a question, hey, what should I do here?

The right decision, do the right thing.

And how he's integrated philanthropy into his day-to-day and the amount of impact he's had is incredible.

I'm not seeing that level of impact from entrepreneurs who have 10 times the resources that Mark has.

So it's really impressive.

And he did it from day one.

So this is not a let's make money and then sprinkle some.

some.

This was fully integrated 111 Salesforce Foundation model from the first day that he launched the company.

And that's where I wanted to tell this story.

I'm going back in time to 2010.

And around this time, he was really big in a capability they had called chatter.

And I was given on loan by Michael Dell to travel around the world with Mark and brief people on this.

So we had implemented it company-wide at Dell.

And then I had gone to France and Asia and New York and all these different places with Mark.

And so we were prepping to do the Dreamforce keynote on this.

And it's the day of the event.

And Mark, if anyone knows him, has a lot of eclectic friends.

So in the back, we're hanging out with Neil Young and Will I.M.

And

so I had never met Will I.

M.

before and I had no idea what I was in tune for, but on this whole philanthropic thing, we get into this huge discussion of how to use cloud computing around this.

We were ideating around this idea that Will I.M.

had about how to bring software into that whole realm of nonprofits because he wanted to do something good.

And it was such.

Like, it was Mark in his element because Mark cares about sales and all that, but he cares from what I learned about him a lot more about giving back to humanity and finding ways to do it.

It was always this way that Mark does have an ego, but he has the biggest heart of any founder I think I ever met in how he's trying to make the world a better place.

Is that a side that you all saw as well?

Absolutely.

When we thought about, and Mike can tell you that we had other offers that were significantly more.

But when you think about, first of all, the great fit, we needed sales expertise.

But when we really did it because we believed and always have about giving back, right?

The more you give, the more you get.

Someone called us do-givers instead of really thinking that if you can tie people together by the good you do, it just makes such more of an impact in the world.

And we loved his 111 model, and it was just a big part of our decision.

I wanted to talk about

relationships in businesses.

So you two

have been in business together ever since you've been dating.

And it's a really magical combination because Cass, you're really about operations and the voice of reason.

And Mike, you're about casting the vision and et cetera.

A lot of times people start businesses and they all have the same strengths and the same weaknesses.

How did you, did it naturally happen that you had these different strengths and weaknesses and that came came together?

Or was it difficult for you to balance each other out and to bring other people in who balanced your weaknesses as well?

I think from the beginning, I've always loved Mike's brain.

And it's just this, it's this place where anything can happen, where he can think about anything and he can come up with just ideas over and over again.

And I've always been an operator.

So I even think when we chose each other as partners, it was just the the glue.

We were just, it was yang.

It was like a perfect compliment.

And it's always worked well because when you have founders, you really do have to stay away from other founders that have the same skill set because you will get stuck in this kind of paralysis of decision and micromanaging and you won't have trust.

And someone's always going to have a bigger opinion and there's going to be a fight.

But for us, it just worked very well and it has kept going.

We also know that we have weaknesses and we do have gaps that we've always surrounded ourselves with other people who fill in those gaps and they become the expertise that we don't have.

Thank you for answering that.

Another thing that I wanted to ask is: you've been together now for decades doing this.

What's the hardest moment that tested your relationship and what got you through it?

Do you want me to answer that one, Mike?

Sure.

I think in 2012,

when Mike and I started going on the road, well, Mike was on the road every week, but I was starting to go on the road like every other week to open up offices around the world.

He decided, and I'm a huge dog lover, don't get me wrong, but he decided that he was going to get a puppy instead of the adult rescue that I had given permission to do for the family.

So I think that was a really hard moment.

But in terms of, I don't think business i think shape matrix was a difficult time for you i didn't necessarily support it but what do you think yeah so i've had one major failure with outcast

it was after salesforce i think i take responsibility for this in the book primarily my ego got in the way i started a company with a very close friend who was an artist and let's just say we did not do what co-founders should do before starting a business, which is not only get on the same page about like strengths, weaknesses, what is the vision, but really the softer things.

How hard do we want to work?

What are the goals for the business?

How are we going to make decisions?

And it was just a complete failure.

And

I'm not going to say Cass said, don't do it, but she was very.

negative on the idea.

We're not, we have the type of relationship where it's not codependent in the sense that there's a very strong we, obviously.

We have three kids.

We've had three dogs, had four dogs, actually.

We have done eight companies together, but there's also a me.

And the me involves, I go to a lot of music, I do stuff with friends, like we have a life outside of each other.

So she wasn't going to say, don't do this.

But she gave me all the reasons why it wasn't going to work.

And, you know, it was one of the few times in my life I didn't listen to her.

And it cost us a lot of money and time and it was painful.

And I think

the best part about Cass, from my perspective, is she's aggressive.

And why I say that is

she's not passive aggressive.

Okay.

Okay.

I'm aggressive aggressive.

For better or worse, I know where I stand every second.

of the day.

The good news is I have not gotten a text during this podcast.

So it means that I'm not talking too much.

I'm not going off the rails.

I'm trying to keep it together.

But Cass is a very good communicator.

And there are people she fired that to this day

tell me that being fired by Cass was the single best day of my life.

And the reason it woke them up.

She told them like their strengths, their weaknesses, why they're not a fit for the organization,

where she thought they would be a better fit.

Oftentimes, if we like them, referring them to businesses.

And so this person had not,

that I'm thinking about in particular, had never been told their weaknesses.

And there's something powerful about

hearing where your shortcomings in a way that is from a position of love.

And the intent is not to hurt you.

I'm not saying we haven't had knockout, knockout, drag out fights over the years.

I can't really think of one off the top of my head, but I know we have, usually because of stuff that I've done.

But it's a really good, if you have a co-founder or you're in a relationship that matters, a spouse, communicate.

Don't let the boogeyman take over because there's usually not a

intention that is bad unless there is, then you've got to get rid of the toxic relationship.

I'm so glad that you brought a lot of this up because one of the things that you say is that the right co-founder relationship is often more critical than the business concept itself.

And I think this was a great example of how that plays out.

And it's, you just brought a whole element because I'm in the middle of co-founding a business myself, and you just brought up a whole element that he and I haven't really discussed, which is the whole work-life balance aspect of it.

And I also think you brought up another good example about Cass letting someone go.

I happened to talk to a person who used to work for Gary Vaynerchuk,

and he was let go by Gary, and he said it, Gary still supports him to this day, but he said it was one of the best wake-up calls because he wasn't bringing his best to the job.

And Gary had given him a couple of chances and then let him go because of it.

But he now has learned that he's got to bring his best self every single day.

And so it became a very important teachable lesson.

And now Gary on the side mentors him, which I think speaks to Gary's character as well.

So thank you for sharing both those things.

Cass, I wanted to make sure I asked you, you speak a lot about leading while raising a family.

What advice would you give women founders trying to navigate both motherhood and startup life?

I would give them the following, which is,

you're not going to do it perfect.

There's no way to give 100% at work and 100% at home and to try to forgive yourself.

And I will tell you being on the other side, when we did our biggest and most successful company, I had a 5-3 and newborn.

So five years old, three years old, and a newborn.

20 years later, they are doing so well.

They are thriving.

They saw a mom that worked really hard, that was generous and loves giving back.

And that is almost more important, the modeling than you do, than being there 100% of the time.

So it's not going to be easy.

You're going to feel a whole lot of guilt and everything's going to be good.

The last thing I really wanted to talk about was hiring a team.

Like, how do you find the right people that are going to help you to grow?

And one of the things that you all reference is I love the movie Moneyball that Brad Pitt was in, and you reference moneyballing your team.

So how do you go about evaluating potential hires beyond their credentials and resumes?

Well, in the beginning, when you are a startup and you're going zero to one, you're definitely going to need people who wear multiple hats.

So if you looked at a couple of our first employees, they did multiple things in the company.

And you can't really divide out departments or processes really yet.

But once you start getting customers and you start having that repeat revenue, then it's time to scale.

And that's where money balling really comes into play, because you're going to have to make decisions on where does everyone fit best.

And they need to do that one thing.

So finding teams, we always found people through people we knew.

And then we incentivized all of our team to bring in their friends.

We had that theory that birds of a feather flock together.

We knew that someone was not going to bring someone in that wasn't going to be the same kind of, we call them buddies back then, buddy that we all wanted, that would work hard, lift people up, root for everybody, and be supportive.

So that really helped.

Hiring managers, very hard.

You also got to be very careful about who you promote as a manager because you better make sure that they're doing their job and also leading at the same time before you promote them.

So it's a combination of really understanding that over time, not everybody scales, which is a really tough lesson because you might have a ton of people there that are really cultural anchors in the company, but they can't move forward in a scaled company, in a big company.

And you have to be the leader who can make those decisions.

Well, thank you for sharing that.

And the last thing I wanted to cover real quickly is a little bit of no-fluff advice that maybe you've never said on stage.

So

I wanted to ask you this.

If a founder walked into your kitchen today with a can't miss idea, what questions would you ask them before you'd invest?

You go first, Mike.

The first one that I would ask is very simple.

Like, what's going to get in your way?

So this all sounds good.

Like you're fired up.

There seems to be a market.

You seem to know the market.

But what are the obstacles we got to worry about?

And the biggest red flag is there's no obstacles.

There's no competition.

This is slam dunk because we've done 100 investments.

We've started eight companies.

Not one of them is up and to the right.

It's not true.

One of them was up and to the right, but most of them take some time to figure it out.

And it's in that figuring it out that you need to be self-aware.

You need to understand what you don't know, what potentially, what are the blind spots.

And so that's a question that really brings to light

how well someone has understood the task ahead.

I'm going to say, who are your first five hires and why?

I want to see how are they going to build a team.

Do they need a team?

Do they think they need a team?

Do they know what they don't know?

And I want to hear their reasoning for those hires.

That tells me a lot about how they think, which is why I usually do all the due diligence on our investments with the people side of it.

I love it.

Well, it was such a profound honor to have you both on the show today.

If people would like to learn more about you, your great new book, et cetera, where's the best place for them to go?

They should just go right to Amazon.

It's there.

They can get it at shoveling shit.

It's right there.

Well, thank you so much.

And thank you for, I agree with Gary about how great a book this is and why he's backed it and why i wanted to have it on the podcast because this is must

read advice for anyone who's in the middle of the entrepreneurial journey so thank you so much for coming on passion structure thanks for having us appreciate you thank you so much and that's a wrap on today's conversation with cass and mike lazaro from the brutal truth about what it takes to scale to the personal costs they never expected, to the power of choosing love for your work, your partner, and your purpose.

again and again.

This wasn't just an episode about business.

It was a conversation about becoming and communicating.

It's about how the people who win long-term are the ones who keep showing up, shovel in hand, and learn to love the mess.

Here are a few key takeaways that I loved and I hope you will carry with you.

Ego is a wrecking ball.

Self-awareness is a survival skill.

Burnout isn't failure.

It's feedback.

Prioritize your well-being like your your life depends on it, because it does.

And success isn't built in spreadsheets.

It's built in the trenches, one hard choice at a time.

So if this conversation resonated with you, grab a copy of Cass and Mike's new book.

It's available now wherever books are sold, and trust me, it's one of the most honest books on entrepreneurship you'll ever read.

Leave a five-star rating and review.

It helps us grow and reach more listeners.

Share this episode with someone who needs a reminder that struggle is part of the story.

And And visit passionstruck.com for links to everything we discussed today.

If this mission speaks to you, I am also booking keynote events for 2025 and 2026, helping organizations ignite growth and purpose from the inside out.

Learn more at johnrmiles.com slash speaking.

Coming up next on Passion Struck, Susan Giesman joins me for a powerful conversation about what it means to live a divinely guided life.

not just from mind or strategy, but from spirit, purpose, and presence.

When you realize that hurt people and that we came here to learn by trial and error, the prayer or statement or mantra, whatever you want to call it, that has made the biggest difference for me is to say to higher consciousness, forgive me for ever thinking I was anything less than love.

Because that's when we make mistakes, when we don't realize we're not only human, that we're souls.

So it's really, forgive me for that action, because if I had remembered I was a soul, I wouldn't have done that.

Until then, live boldly, lead with purpose, and as always, live life passion-struck.

Shopify's point-of-sale system helps you sell at every stage of your business.

Need a fast and secure way to take payments in person?

We've got you covered.

How about card readers you can rely on anywhere you sell?

Thanks.

Have a good one.

Yep, that too.

What one place to manage all your online and in-person sales?

That's kind of our thing.

Wherever you sell, businesses that grow grow with Shopify.

Sign up for your $1 a month trial at shopify.com/slash listen.

Shopify.com/slash listen.