Why Balance Is a Lie for Entrepreneurs

Summary

The Duct Tape Marketing Podcast: "Why Balance Is a Lie for Entrepreneurs"

Hosted by John Jantsch | Released on May 28, 2025

In this insightful episode of The Duct Tape Marketing Podcast, host John Jantsch welcomes seasoned entrepreneurs and investors Mike and Cass Lazzaro. Renowned for co-founding Golf.com and Buddy Media (later acquired by Salesforce for $745 million), the Lazzaros bring a wealth of experience from supporting nearly 100 early-stage startups and contributing over $10 billion in realized gains. The duo delves into their latest book, "Shoveling a Love Story: The Entrepreneur's Messy Path to Success," exploring the intricate realities of entrepreneurship beyond the glossy success stories.

Unpacking the Title: Embracing the Grind

The conversation begins with an exploration of the book's evocative title. Jon Jantz asks, "The metaphor is I love being an entrepreneur. It doesn't sound very fun." Mike Lazzaro responds by illustrating the daily grind of entrepreneurship:

"It's about probably 10 failures in one win a day. Right. So you're shoveling non-stop and you get that one win and that's what keeps you going. It's kind of like golf to tell you the truth." (01:53)

This metaphor highlights the relentless effort and resilience required to navigate the ups and downs of entrepreneurial ventures.

Entrepreneurship and Partnership: Working with Your Spouse

Jantz then shifts the focus to the dynamics of working closely with a spouse. He poses a common concern: "how do you guys make that work? Or I guess first I should say, do you make that work?"

Cass Lazzaro explains their success by emphasizing complementary skill sets:

"Cass is an incredible operator, very detail-oriented... I am much more of the visionary salesperson... having a co-founder who compliments whose strengths aren't necessarily your strengths and whose weaknesses you can make up for really creates a partnership where you could rely on each other." (03:39)

Mike adds that dividing and conquering tasks helps prevent disagreements:

"The times that we get into disagreements are when we are in the same lane... we realized that when you can define and conquer and you have that implicit trust... then you've got to delegate and let go." (04:33)

Their approach underscores the importance of trust and clearly defined roles in both business and personal relationships.

Debunking the Myth of Work-Life Balance

A central theme of the episode is the dismissal of the traditional work-life balance model for entrepreneurs. Jantz introduces the concept:

"You've heard that a billion times. I'm sure, as I have you lean into something you call the imbalanced life. And I actually, I've never called it that, but actually I think I'm going to agree with your concept because I think that's really what makes it work." (04:33)

Mike elaborates:

"With entrepreneurship, you have no balance... you're going to be all in. So it's the first thing you're thinking about. It's the last thing you're thinking about when you go to sleep..." (05:00)

Cass reinforces this by highlighting the necessity of prioritization over balance:

"There are trade-offs. What is the target keeps moving all the time." (06:13)

Their candid discussion offers a realistic perspective, encouraging entrepreneurs to embrace an imbalanced life as a pathway to success.

Cheat Codes for Entrepreneurial Success

Transitioning to actionable advice, the Lazzaros share key "cheat codes" from their book, starting with Focus and Transparency.

Focus

Cass emphasizes the critical role of focus in achieving business objectives:

"Priorities determine the outcome of your business... one of the reasons why entrepreneurs do not succeed is that they're not focused on the right things or they're focused on too many things." (09:58)

She advises entrepreneurs to identify and articulate their top three priorities clearly, ensuring alignment across the organization.

Transparency

Mike highlights the importance of transparent communication:

"If you're going to lead... you've got to tell them everything. The good, bad, and ugly." (10:01)

He shares how their commitment to transparency during challenging times, such as the potential bankruptcy of their acquisition partner, kept their team unified and loyal.

Navigating Uncertainty and Embracing Change

The discussion pivots to the inevitability of uncertainty in entrepreneurship. Cass states:

"It's about embracing uncertainty as something you shouldn't fear." (11:51)

She explains that thriving amidst uncertainty involves making informed, confident decisions and adapting swiftly to changing circumstances. Mike adds that seasoned entrepreneurs view uncertainty as an opportunity:

"Let's just call it uncertainty... uncertainty or even like a failed product launch as getting one step closer to the thing that's actually going to work." (13:18)

Their insights encourage entrepreneurs to develop resilience and flexibility, viewing challenges as integral to the growth process.

Lessons from Failure: The Golf.com Acquisition Debacle

A pivotal moment in their entrepreneurial journey, the acquisition of Golf.com by Chipshot.com, serves as a powerful learning experience. Mike recounts:

"We took an all-stock deal because our entire board voted for that... by March 2000, the CEO of chipshot.com called us and said they were going bankrupt... we had to tell every single employee." (13:51)

This experience taught them invaluable lessons in due diligence, transparency, and the importance of resilience. Cass adds a personal account of attempting to start a company without a trusted co-founder, highlighting the critical nature of partnership compatibility:

"I take responsibility for not going through the motions of understanding how we were going to work together... if you start a company with someone who you can't work with, it's hard to rebound from that." (16:39)

The Art of Pivoting: Knowing When and How

Jantz inquires about the indicators for pivoting a business model. Cass responds:

"We've pivoted 8, 9, 10 times... it always comes from a combination of metrics and gut feel." (17:05)

She advises entrepreneurs to continually assess key metrics and remain open to change, ensuring that their strategies align with evolving market demands and business realities.

Legacy and Philanthropy: Beyond Financial Success

Concluding the episode, the Lazzaros reflect on their desired legacy. Cass articulates their shift from personal achievements to scaling their impact:

"The next 50 years for us is about scaling our impact... help entrepreneurs build businesses and lives even bigger and better... Cycle for Survival... raised over 400 million." (19:54)

Mike adds the importance of generosity:

"If we can continue to be generous in our time and giving back to others, I think that would be great." (21:22)

Their commitment to philanthropy, particularly in cancer research, underscores a broader vision aimed at societal betterment alongside business success.

Connecting and Learning More

As the episode wraps up, Mike and Cass invite listeners to explore their work further:

"Visit shovelingshit.com... it's not just about the shoveling, it's a love story about our love for entrepreneurs." (21:32)

Their candid and relatable insights offer a refreshing take on the entrepreneurial journey, emphasizing resilience, transparency, and impactful legacy over the elusive ideal of balance.

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Key Takeaways:

1. Embrace the Grind: Entrepreneurship involves relentless effort and accepting frequent setbacks.
2. Complementary Partnerships: Successful business partnerships, especially with a spouse, rely on complementary skills and clear role definitions.
3. Reject Traditional Balance: Instead of striving for work-life balance, prioritize and manage the inevitable imbalances inherent in building a business.
4. Focus and Transparency: Concentrate on key priorities and maintain open, honest communication within your team.
5. Adapt to Uncertainty: View uncertainty as an opportunity for growth and remain flexible in your strategies.
6. Learn from Failures: Use past setbacks as valuable lessons to inform future decisions and avoid repeating mistakes.
7. Define Your Legacy: Beyond financial success, aim to create a lasting positive impact through philanthropy and empowering others.

For those interested in diving deeper into Mike and Cass Lazzaro's entrepreneurial insights, their book "Shoveling a Love Story" and their website shovelingshit.com offer comprehensive resources and guidance.

Transcript

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[Jon Jantz]

Hello and welcome to another episode of the Duct Tape Marketing podcast. This is Jon Janssen, my guest plural today, Mike and Cass Lazzaro. They're seasoned entrepreneurs and investors best known for co founding Golf.com and Buddy Media. Latter acquired by Salesforce for $745 million. They supported nearly 100 early stage startups, contributing over 10 billion in realized gains. But today we are going to talk about their latest book, Shoveling a love Story about the entrepreneur's messy path to success. So welcome to the show, Mike and Cass.

[Mike Lazzaro]

Thanks so much for having us. John.

[Cass Lazzaro]

Thank you. Thank you.

[Jon Jantz]

You know, we have to actually start with the title. The metaphor is I love being an entrepreneur. It doesn't sound very fun.

[Mike Lazzaro]

Well, we kind of looked at it that, you know, what is it that you do every day when you're an entrepreneur? And you know, I said this to Mike the other day, it's about probably 10 failures in one win a day. Right. So you're shoveling non stop and you get that one win and that's what keeps you going. It's kind of like golf to tell you the trut.

[Jon Jantz]

That's right. That's right. Many of time I've stayed on the course because I had one good shot.

[Mike Lazzaro]

One good shot. That's right. So that we wanted to be the most realistic when it came to a title.

[Jon Jantz]

Yeah. And I think that, I mean, obviously you're talking about the fact that there are messy aspects of it, but that's actually how you get through is embracing that, isn't it?

[Mike Lazzaro]

That's right. That's right.

[Jon Jantz]

So how has it been? I don't know how long you all have been together, but I assume that your entrepreneurial journey has Been mostly together. I'm sure you get that question all the time, you know, because I think a lot of people probably can't imagine working with their spouse. So how, how do you guys make that work? Or I guess first I should say, do you make that work?

[Cass Lazzaro]

We make it work because it works. And when I say that, it's because we do very different things, even though we are start the companies together. Cass is an incredible operator, very detail oriented. She thinks in spreadsheets. I am much more of the visionary salesperson, product person, I think in screenplays and PowerPoints and more creative medium. And whether you're married or not, having a co founder who you compliment whose strengths aren't necessarily your strengths and whose weaknesses you can make up for really creates a partnership where you could rely on each other. If we did the exact same thing, I think it would have been a very different story. Let me just tell you, John, nothing.

[Jon Jantz]

Would have gotten done right.

[Cass Lazzaro]

Would have been harder.

[Jon Jantz]

Ideas are great. Need some, need a little execution. You know, as I listen to you describe that though, I mean, we can go into a little bit of couples therapy here. That's probably the recipe for a good marriage too, isn't.

[Mike Lazzaro]

Definitely has been for us because we divide and conquer. And I think I will tell you that the times that we get into disagreements are when we are in the same lane. And we figured that out actually writing the book, because when we work, we don't get in disagreements. We might say we don't agree with a decision, but when we wrote the book, and parenting is very difficult with two people, it was harder. And so we realized that when you can define and conquer and you have that implicit trust that each of you owns something and has the expertise to do it, then you've got to delegate and let go.

[Jon Jantz]

So pretty common desire for people out there that start businesses to like create this healthy work life balance, right? You've heard that a billion times. I'm sure, as I have you lean into something you call the imbalanced life. And I actually, I've never called it that, but actually I think I'm going to agree with your concept because I think that's really what makes it work. But go ahead and explain how that. Or elaborate on that concept, I guess.

[Mike Lazzaro]

So with entrepreneurship you have no balance because the thought is that you can only do one thing really well at a time. And if you think about, you know, your priorities right, you're going to be all in. So it's the first thing you're thinking about. It's the last thing you're thinking about when you go to sleep and you're probably dreaming about the to dos that you have to do, if you're even getting sleep. So this concept that everyone always asks us, well, how do you guys do it? What's the balance? There is no balance. There are times when you're all into one thing and other things suffer. Right. I'm not saying they're suffering to the point of, you know, massive consequences, but they're not done with the same probably intensity and clarity as what you're really focused on. So we just don't believe that there's an, like a balanced way to go through life when you're an entrepreneur because you will have things that you have to make decisions about and there are trade offs.

[Jon Jantz]

Yeah. And I suspect there's a great amount of stress that accumulates with people who feel like they have to have that. Right. But you're almost admission to say, hey, this is going to suffer this month or this quarter because we got to do this.

[Mike Lazzaro]

That's right.

[Jon Jantz]

I think it's probably a healthier way to look at it, isn't it?

[Mike Lazzaro]

Yeah. And also it kind of lets you off the hook, Right. That you have to be perfect in all areas, especially if you're an entrepreneur who has kids. Right. Because relationships suffer when you're doing something and founding something because you're all in. And so, you know, we looked at it like when our kids were little, and I'm talking like five, three and newborn. We knew that they were getting probably 80% of us. They just weren't getting the hundred percent totally, you know, on every single thing.

[Jon Jantz]

Yeah, they probably survived.

[Mike Lazzaro]

They do.

[Jon Jantz]

Great. So are they coming to anywhere close to an age where they might join you in some of this?

[Cass Lazzaro]

Yeah, yeah, they already are. So we have a son, Miles, who's launching a business very soon. He's working on it. And we've done a lot of work with our son Cole on our golf team and he's a business major at Emory. And Viv has high executive functioning skills and is an incredible operator like her mom. If you've ever seen her plan something, you can see that Vivian, our youngest, got a lot from Cass. And really everyone's born an entrepreneur. We think many of us go through the normalization process of school and college and we're told to sit down, shut up, do what everyone else is doing. And then you go out into the world and people say, why are you different? Right. Like, how are you going to create something you were Taught how to memorize dates and history and all this stuff. And so kind of what we want to do with this book is very simple, is like, you know, give you the cheat codes that we wish we knew at the beginning to help short circuit many of the mistakes that you're going to make and not only build a successful business, but hopefully a successful life. What's the value of a business and money if your life is in disarray? And, you know, Cass and I have spent a lot of time trying to build a relationship and other relationships, and it just doesn't happen by accident. And so a lot of those cheat codes about how to do date nights and how to put stuff on your calendar, that's important, it contributes to how to operate within the hurricane of the imbalanced life.

[Jon Jantz]

Yeah. It's funny. I listen to you talk about the school thing. I didn't take tests very well because I always wanted to know why or how stuff worked. And you never got rewarded for asking that question.

[Cass Lazzaro]

You're talking to a 1080 SAT. So I'm with you.

[Jon Jantz]

So I was going to go to the cheat codes. Let's dial up a few. Maybe I'll challenge you each to pick your favorite.

[Cass Lazzaro]

Yeah. So my favorite by far right now is focus. And your priorities determine the outcome of your business. This is not something that we knew when we started these businesses way back when I was 18, 19 when I started my first one. But what we've seen is that one of the reasons why entrepreneurs do not succeed is that they're not focused on the right things or they're focused on too many things. So the first question I ask any entrepreneur is, what are your top three priorities to reach the vision you have? So an entrepreneur will say, I want to be the number one maker of shoes and whatever it is. Okay, what are the top three things you're doing to get there? And if they cannot list it off right away without hesitation, that means they don't know it, their employees don't know it, their investors don't know it. So they're never going to be able to get to that vision if they don't need. If they don't understand what they need to focus on to get there.

[Jon Jantz]

All right, so focus from you. How about you guys?

[Mike Lazzaro]

Mine's all about transparency with communication. So you really do. If you're going to lead and you're going to start executing and you're going to be going, you know, 100 miles per hour, the only way to keep all the wheels on the bus and your most valuable resources, right? Your most valuable assets in your company. Your people that are putting in, you know, time and time again, all of their sweat and tears to help you reach your vision. You've got to tell them everything. The good, bad and ugly. They can take, you know, bad news. They can't take surprises. So we've always led with just massive transparency, which has really worked for us.

[Jon Jantz]

Hey, it's Jon Jantz here. Look, if you're an agency owner or a marketing consultant, who's feeling the pressure, right? Tactic overload, killing your groove, retainers drying up. AI is changing the game. Then it's time for a new model. That's why we created the Anti Agency Model workshop. Look, there's nothing wrong with agencies. It's the model that's broken. So what's the new model? It's a framework for delivering strategy. First system based marketing that scales without burnout. Look, learn how to evolve and thrive in the Future. Check out DTM World/New Model. That's DTM World New Model. I'm feeling a lot of the businesses I talk to right now. This first quarter of 2025 felt like there was more change and evolution in how we work than maybe the last five years put together. And I'm, I'm even talking to entrepreneurs who are like, I'm just tired, you know, I just don't want to like learn a whole new game. Yeah, that I suppose goes pretty much into embracing the grind as an aspect of yours. What do you tell folks that now? Just feel like, yeah, okay, I'm embracing the grind, but the target keeps moving all the time.

[Cass Lazzaro]

I think the number one thing is it's not just embracing the grind, it's actually embracing uncertainty. And so really what's going on in the world today is what's gone on for entrepreneurs forever, which is uncertainty. Right? You start a company, who's going to be my customers? Where am I going to get all of my stuff to build the product? How am I going to market it? Right? And so uncertainty will never go away. Even though I think we're in peak uncertainty, right? One news cycle and all of a sudden it's, whoa, we've completely done 180. If you as an entrepreneur can learn to not only love to shovel, but really embrace uncertainty as something you shouldn't fear, you will thrive inside it no matter what's happening. Right? And many entrepreneurs have to deal with this all the time. And so we're working with a lot of companies that import a lot of supplies and products from all over the world. And to a T, every entrepreneur is like, we'll figure it out. Right. And they know how to make informed, confident decisions and operate and move forward even in a world of peak uncertainty. Much different than if you have a job that you're doing one segregated duty. And you've never done anything differently. Right. You're not a utility infielder.

[Jon Jantz]

Yeah. In fact, you go through enough cycles of this and I suspect you start seeing uncertainty and change as opportunity. Right.

[Mike Lazzaro]

I mean, that's right.

[Jon Jantz]

You've seen it before. Right.

[Mike Lazzaro]

And we, you know, as true entrepreneurs look at, you know, let's just call it uncertainty or even like a failed product launch as getting one step closer to the thing that's actually going to work.

[Jon Jantz]

Yeah. So since you mentioned failure, were there any significant learning experiences for you along the road that that really kind of helped inform maybe some of the cheats in the book?

[Mike Lazzaro]

No doubt. Like the number one, I think experience for Mike and me was our [e-mail] when in 1999, December 23rd, we were bought, we were acquired by chipshot.com they were a Sequoia backed company going public in April of 2000. And we took an all stock deal because our entire board voted for that. And we thought we in a year and a half had made it big. We were going to be, you know, millionaires. You know, times a hundred is the, you know, height of the dot com like bubble. And by March 2000, the CEO of chipshot.com called us and said they were going bankrupt, that Sequoia pulled out and we were going into bankruptcy with them. So it taught us a lot. It taught me about due diligence and what did I miss? It taught me about transparency because we had to tell every single employee that we had. We didn't even control the bank accounts. And what was amazing is because we'd always led with transparency for three months while we went out and raised money and started the company over, they all stayed, not one employee left. And I think it taught. I think that's where like I would say, like I really tapped into my competitive nature. I hate losing more than I love winning. We just learned a lot. What about you, Mike?

[Cass Lazzaro]

So that one's a huge one. And as Cass talks about it, you know, the company was started by three Harvard graduates or maybe dropouts. I forget if they. But very young, we were all very young and they went on to do great things. So we all learned so much from this failure of, you know, how to fund a company, how to make sure. You don't run out of money, how to hire responsibly, how to attack a market unit, economics of products, which is one example.

[Mike Lazzaro]

Not shining the turd.

[Cass Lazzaro]

Right? Yeah. And so, you know, one of them, you know, Rajiv Goel started Pubmatic. Nick Mehta started Gainsight, which is a huge, you know, software company right now. Amer Goel has had a great career. So those are the three founders. I also started a company without cas, and it showed me the importance of having a co founder who you can trust, who you have different skill sets. And we just couldn't work well together. And the company to date has been, you know, a huge failure. And I write about that in the book. I take responsibility for not going through the motions of understanding how we were going to work together. What are our values? Are they shared? Is the work ethic the same? Is our vision for the company the same? And that's a really hard thing. Like, if you start a company with someone who you, for whatever reason, can't work with, it's hard to rebound from that.

[Jon Jantz]

So speaking of pivots, is there. I know you look at a lot of companies, a lot of startups, you know, to invest in things, or there are times when you, like, are there certain indicators that say, you know, this company should pivot, or is it just for another opportunity, or is it just because no market fits? Is there something that you look for in. In suggesting somebody really changed their, maybe their whole purpose?

[Cass Lazzaro]

So as an investor, you know, well, first of all, as entrepreneurs, we've pivoted 8, 9, 10 times. And so that always comes from a combination of metrics and gut feel. So when you set out to do something, how are you going to know it's successful? Identify those metrics. But really deep down in your belly, you know, when things aren't going as expected. And unfortunately, as human beings, we have a tendency to do more of the stuff that doesn't work and is not working than change to do the stuff that is working. I remember Marc Benioff. We were in a meeting after we sold. He said, just do more of what's working and less of what's not. And it hit me like, man, that is deep, because he pointed out that we were doing some stuff that just wasn't working. Okay, It's a new company. And so, you know, we've. As an investor, it's very hard for the investor to force a pivot. But you could ask questions. You know, the questions are, why are customer metrics not meeting your expectations? Why is There no one using the product. Do you think there is another psychographic of people who you think would be more attracted to the product and have you tried to reach them? Right. So you ask a series of questions which force the entrepreneur to think to themselves, it's not about them reporting to you, but it's about them getting their own thoughts in line, usually written down. And if they can't convince themselves, they're never going to be able to convince anyone else.

[Jon Jantz]

I know I personally respond a lot better to somebody asking me questions than telling me what to do. Because, you know, that definitely. That definitely makes me figure it out. You know, rather, we respect entrepreneurs too much resistant to, like, just being told what to do.

[Mike Lazzaro]

But I think entrepreneurs also have to go back to their measurements of success, right? So if they've. If they really have goals that they've written down, and certainly if they've told their board and investors those are the goals for the first year, what they need to do is go back to how they define success with each data point, right? So you say, like, okay, I'm have 15 customers. If you have three, that's a good data point to kind of understand what's happening. And then you have to open that up. You have to put aside your ego and your pride and say, okay, what's really going on here?

[Jon Jantz]

So you guys have your hands and have had your hands in a lot of things. You've been wildly financially successful. But beyond that, is there any kind of, have you thought legacy, what you want to kind of leave and accomplish in the entrepreneurial world? Obviously, the book is something that will live on. I'm curious if you give that much.

[Cass Lazzaro]

Thought, Cass, do you want to take that?

[Mike Lazzaro]

You go first.

[Cass Lazzaro]

Yes. So the last 50 years have been very much about earning. For us, that meant earning degrees because we went to college and reputation and money and all this stuff. The next 50 years for us is about scaling our impact. And that's on two fronts. One is how do we help entrepreneurs build businesses and lives even bigger and better than what we built? So we do not think that what we did is unusual. Anyone can do it with the right focus and the right effort and the right funding. And that's what the book's about. But it's what our speaking's about. Our founders, farm, community, it's all that. We've always integrated philanthropy into everything we've done, not only because we wanted to, but it's great for culture. And there's nothing better to make you feel better, but also an organization. Bring it together. And so Cycle for Survival, which we were the first corporate team and we're still very involved and on the leadership committee for we've raised over 400 million. 100% goes to cure cancer research. And we've made huge strides, but too many people we know are still being impacted by cancer. So if we can, at the end of the day, if we could help companies and help founders reach their potential and if cancer is cured, we think our life was worth living.

[Mike Lazzaro]

I'll add one thing. I think if we can continue to be generous in our time and giving back to others, I think that would be great.

[Jon Jantz]

Well, that's a great note to end it on. I appreciate you taking a moment to stop by the Duct Tape Marketing podcast. Is there anywhere you'd particularly like to invite people to find out more about your work? Obviously, I know the book will be available everywhere, but anywhere you want to invite people to connect with you.

[Cass Lazzaro]

Yeah. Www.shovevelingshit.com. you know, we embrace the shit, but it's not just about the it's shoveling a love story. So our love for entrepreneurs are hopefully very evident when you go to shovelingshit.com.

[Jon Jantz]

So I'm curious, did you have to buy that URL or did was that available?

[Mike Lazzaro]

John? It was available, if you can believe that.

[Jon Jantz]

That is amazing.

[Cass Lazzaro]

That's when we knew that it was right.

[Mike Lazzaro]

We knew it was the correct name.

[Jon Jantz]

That's hysterical. Awesome. Well, again, I appreciate you stopping by the show and hopefully we'll run into you one of these days out there on the road.

[Mike Lazzaro]

Love it. Thanks, John.

[Cass Lazzaro]

Appreciate it.