Shoveling $h!t by Kass Lazerow A Love Story about the Entrepreneur's Messy Path to Success
What's it about?
Shoveling $h!t (2025) is an honest look at the realities of being an entrepreneur. Too many entrepreneurs walk into the business world, not realizing it involves a lot more shit-shoveling and less champagne-popping than social media would have them think. Fortunately, you can go in prepared thanks to these lessons from high-growth founders who’ve just about seen it all.
Shoveling $h!t
Did you know that nearly one in five adults around the world are in the process of creating a business? Five and a half million new businesses were launched in 2023 alone!
If you’re here, you’re probably one of these folks – or you’ve fantasized about becoming one. You’ve imagined a glorious future where you get to choose your own hours, make lots of money, and generally be in charge of what gets done when.
The thing is, this fantasy is just that – a fantasy. Sure, being a business owner definitely comes with more freedom than your typical 9-to-5, and there can be significant financial payoff. But there’s also a lot of crap to shovel throughout the process. A global pandemic could suddenly shut down your brick-and-mortar, or there could be a market crash that hurts your ability to get funding, or a family member could sue you after investing.
The crap-shoveling never ends – it’s an eternal part of the entrepreneurial life. The best advice this lesson can give you? Learn to love it.
In the next sections, you’ll get an honest look at what being an entrepreneur is really like, from the perspective of Kass and Mike Lazerow – a married couple who’ve started several successful companies together and invested in many more. You won’t get a comprehensive how-to for starting a business. But you will hear about the less-glamorous truths that’ll help prepare you for when shit hits the fan.
Kass had just been wheeled into the recovery room after undergoing an emergency C-section. Thankfully, their newborn son, Cole, had been delivered healthy. Kass, however, wasn’t doing so well. Before the surgery, the epidural she’d received had clotted in her brain. This caused stroke-like symptoms – the entire left side of her body had drooped and gone numb.
She was idly wondering whether her face would permanently be stuck like that when her husband and cofounder, Mike, gingerly placed a laptop on her stomach. “I hate to say this right now,” Mike said, “but Buick needs their ads up.”
The most important ads of their career were scheduled to go live. The 68th Masters Tournament would begin in four days, and professional golf tournaments played a huge role in the profitability of their company, Golf.com. There was no wiggle room. If Mike didn’t sell ads, and if Kass didn’t traffic and manage them, they’d have no revenue. No revenue, no company.
Mike tried to cover for Kass when she went into labor early, but he didn’t know how to do her part of the job. So, just minutes after giving birth, she logged into the management platform and turned on the ads while Mike sung her praises.
Hearing this, you might be shocked and a little horrified. How could Kass and Mike have been worried about their revenue at a time like that?
But from Kass and Mike’s perspective, that’s how entrepreneurship works – for better or worse. This situation was far from an anomaly. When their first son was born, Kass took less than a week of maternity leave. Then, it was in the hospital after their third child was born that Mike had the idea for their next company, Buddy Media.
As an entrepreneur, you have to accept that doing something meaningful to you comes at a cost. In Kass’s view, you can only do one thing really well at a time. If that one thing is starting and growing a business, then your relationships will suffer. Likewise, if relationships are the priority, your business will suffer.
Kass and Mike definitely felt the impact of prioritizing their business. They weren’t there for their kids as much as they would have wanted – though they never missed one of their kids’ plays, rehearsals, or games, they were always tired, never fully present. Plus, they developed almost no meaningful friendships outside of work, and both experienced major health issues. They couldn’t fully take care of themselves physically, mentally, or emotionally.
Are you willing to embrace these realities? If not, you probably shouldn’t become an entrepreneur. But if you are, there are ways of managing the imbalance as best you can.
For Kass and Mike, they openly discussed and agreed about sacrificing time with their kids when they were young so that they would hopefully get more time with them later. They chose to focus on financial success to provide their kids with a better life and to improve the world through philanthropy. That wasn’t necessarily the right decision – but it was a conscious one made through honest communication.
Before taking the plunge and starting a business, do a lot of self-reflection and make sure the tradeoffs are ones you’re willing to make. Remember: you will sacrifice some combination of friendships, family, and health. Are you still ready to grab that shovel?
Aspiring business owners tend to spend a lot of time focused on the cofounder question – that is, whether they should have one.
The truth is, success or failure isn’t guaranteed either way. On the one hand, 80 percent of all billion-dollar startups have two or more founders. On the other, companies with solo founders tend to survive longer and generate more revenue. That’s why Kass and Mike believe it’s not really about having a cofounder or not – it’s about having the right one if you choose to go in that direction.
It’s a lot like picking your spouse. Your cofounder is the first person you talk to at the start of the workday, the person you vent to, and the person you celebrate with. So, you want to be sure you’re with the right person. How? It helps to assess whether you’re on the same page with your vision, values, communication, mindset, and workload.
First, founders need to agree on vision – where they want to go. They should also agree on values. Is your cofounder willing to cut corners you would never cut? If so, it’s good to try and find that out in advance. Also, how does your cofounder prioritize their values? Say your cofounder deeply values family, and she has three kids and an ailing parent. How might that affect her commitment to the business?
Communication is also essential. You need to be able to openly give honest, constructive feedback and discuss difficult issues. A whopping 65 percent of startups fail due to founder conflict. If you can’t handle regular disagreements, you won’t be able to handle the big “Oh shit” moments either.
Strong partnerships require a shared growth mindset – the belief that talent can be developed through hard work, good strategies, and input from others. Cofounders should both believe in each other’s ability to embrace challenges, learn from criticism, and get inspired.
Finally, cofounders need to share the workload and be equally committed to doing what it takes for the company to succeed. This doesn’t mean performing identical tasks – definitely play to your strengths. But you don’t want a relationship where you’re doing 90 percent of the work. That’s a recipe for resentment, and it’s demotivating for your employees.
This approach applies to hiring your employees, too. A company’s first 20 employees contribute to the soul of your business and set the tone for all future hires. Your initial hires should fill in the gaps the cofounders can’t and should be tied to your biggest priorities.
For example, Buddy Media’s hiring strategy was based on customer needs. Their initial business model involved building apps, which required specific technical skills. So, they prioritized hiring engineers.
If you get it right with the first batch of employees, you get them to bring in their friends. At Buddy Media, employees were given a sizable bonus for every referral – as well as a coveted position on the referrals leaderboard. These incentives ensured everyone knew how important hiring was, which ultimately saved the company a lot of money and time.
Sweetgreen’s product concept was pretty simple: they wanted to offer food that was both healthy and convenient. The company was born from three Georgetown college students’ dissatisfaction with campus food options, which failed to balance speed, price, and nutritional value.
Today, Sweetgreen is worth about $861.1 billion dollars. How’d they do it? Simple: they answered the questions on the “Go Gauge.” The Go Gauge is a measure that Kass and Mike use to determine whether to invest in an early-stage project. It involves just six questions. But without solid answers to all of them, funding is a no-go.
Entrepreneurs are often instructed to make a 30- or 40-page business plan with a bunch of different sections and appendices. But in Kass and Mike’s view, less is more. A clear, one-page set of answers to a few key questions helps them – and you – focus on the pure vision needed to invest time or money into an idea.
The six questions on the Go Gauge relate to six key areas: product, differentiation, customer, sales and marketing, delivery, and financial model.
We’ve already discussed Sweetgreen’s product – healthy, convenient food. But what differentiated it? It was simply better than anything else that existed. When it first opened in 2007, there weren’t many quick-serve restaurants with healthy options. For your company, differentiation could mean being faster, cooler, smaller, bigger, cheaper, or fancier.
The next element in the Go Gauge is your customer. Who’s your audience? Sweetgreen targeted consumers who value healthy food, convenience, and reasonable prices. Relatedly, what size is your market? Sweetgreen’s founders knew there was a huge market for people who eat out regularly – three out of five Americans go out for dinner at least once a week and, on average, order delivery 4.5 times a month! It’s good to consider roughly how many potential customers exist, because that number needs to be big enough to justify the size of the company you’re building.
Fourth is sales and marketing. Customers won’t find you on their own – you need a plan for reaching them via marketing and advertising. You might only sell directly to consumers online, like the companies Wayfair and Chewy. Or you might only have physical stores, like smaller retailers.
Along similar lines, you need to consider delivery – how will you get your product to your customers? For Sweetgreen, it was their restaurants. For other companies, it might be through an app store.
Last but not least, there’s the financial model. This bit makes all the difference. On its surface, it’s straightforward: calculate the revenue you expect to get from customers and what you expect to spend making your products and running your company. Unfortunately, entrepreneurs tend to grossly overestimate their revenue and underestimate their costs. So, after you’re done creating your financial model, cut the revenue in half and then double the expenses. It’s much better to exceed your projections than to fall short.
What’s the one thing that can take any company down? That’s right – running out of money. Just like a baby can’t survive without food, your company can’t survive without cash. That’s why Kass and Mike like to say that the first three jobs of an entrepreneur are: don’t run out of money, don’t run out of money, and don’t run out of money.
Hoping that you suddenly generate more revenue is never a strategy. You need to focus your efforts on concrete ways of getting funds – and that means fundraising. Yes, fundraising can feel scary and awkward. But embrace the crap, because you’re going to have to do it.
Fundraising starts with your mentality. The most important thing is believing in your company and yourself. Think about it like this: you’re not asking for money, you’re offering investors an opportunity. In the end, the worst thing that can happen is that they say no.
Founders typically end up paying for the startup costs themselves, at least initially. That’s what Kass and Mike did to get Golf.com off the ground – buying computers, software licenses, office supplies, and so on. For you, this might mean leasing a space for a restaurant or hiring engineers. Also, know that you’ll likely have to forego a salary and work out of an apartment or garage – just like the founders of Google, Apple, Amazon, and Disney.
By investing what you can early on, you’re showing investors you’re sharing the financial risks. But when your business needs more than you have, look to outside sources: angel investors like friends, colleagues, and family; venture capital firms; strategic investors; lending institutions; grants; or corporate programs.
Friends, colleagues, and family members are your first source as a first-time entrepreneur. Each of Jeff Bezos’s siblings invested $10,000 in Amazon – now, each stake is worth more than $1 billion. But remember, things don’t always work out as planned. When friends and family invest, you’re risking your relationships as well as their money. Be sure to overcommunicate about risks and timelines, and assure them they should only invest money they’re willing to lose.
If you’re raising venture capital, remember that VCs are professional investment firms whose primary responsibility is stewarding their investors’ money. They know a lot more about deal terms than you do and will act in their investors’ best interest when things go sideways.
So choose your partners deliberately. Find ones who share your values and vision, offer simple and mutually beneficial terms, and provide tangible value. Finally, avoid “shotgun marriages” with VCs who are trying to get you locked into an unfavorable commitment.
One final bit of advice: always be in fundraising mode. This doesn’t necessarily mean you’re actively raising money at all times, but it does mean expanding your network and building relationships. Show people you care about them, regardless of what they might give you in return.
In the 1950s, Stanford MBA student Phil Knight believed the American fitness industry was about to explode. He wrote his thesis on the athletic shoe market and eventually went on to found the company Nike.
But before Nike became the company we know today, Knight had to do a lot of shoveling. First, he traveled to Japan and convinced the head of Tiger running shoes to give him the exclusive right to sell their shoes in the western United States. Then he started selling the shoes out of the back of his car at track events. Today, Nike generates $50 billion in annual revenue. But the first $1 million came from Knight’s hyperfocus on his main priority: selling shoes.
Knight’s example proves that hyperfocusing from the start is critical to a business’s long-term success. With the right planning and focus, you can prioritize the few most important aspects of your business and execute them well.
To determine your company’s priorities, first imagine you have a gallon jug. You need to fill it with big rocks, sand, and pebbles. If you start with the small stuff – the sand and pebbles – you won’t fit all the big rocks inside. That changes if you start with the big rocks instead, then add the sand and pebbles to fill in the gaps.
This is a metaphor for your company’s priorities. The big rocks are your organizational priorities – the stuff that should be taking up most of your time and bandwidth. What these are exactly depends on your business, but they could include sales, hiring, or expanding to new markets.
The pebbles are things that will matter in the next twelve months. For Buddy Media, these included meeting with potential investors, having breakfast with potential future employees, and brainstorming product extensions. None of them were immediately critical, but they all mattered later on.
Finally, the sand is all the small stuff that doesn’t differentiate your business but nevertheless needs to get done. It’s paying payroll, filing taxes, and closing the financials.
Once you’ve determined your priorities, you can create a plan. Without a plan, you have no idea where you’re going and what success looks like. Your plan should include attainable, specific, relevant, and time-bound goals. Every rock you prioritize needs an associated metric that will tell you whether or not you succeeded. For instance, if sales are the number one goal, how do you know whether you’re doing well? If you’re focused on hiring, it’s how many people, what types of people, and by when?
Don’t forget to write your plans down! If you and your employees can’t refer to the plan at any time, your plan doesn’t actually exist. Coming up with the plan, and then acting on it, is a key part of your everyday shoveling. By hyperfocusing on your most important priorities, you ensure you’re not spreading yourself too thin and that you can execute as well as possible.
Before Instagram became Instagram, it was a little-known app called Burbn. Burbn was essentially a gamified version of the location app Foursquare, in which users earned points for checking into local businesses. Its founder, Kevin Systrom, created it as a side project while learning to code.
Burbn wasn’t exactly a hit. Nonetheless, Kevin didn’t quit. He believed Burbn had a unique feature – the one that allowed users to post pictures with friends. So he stripped away almost everything from the app except for that feature, plus the ability to add a filter, like, and comment on photos. He renamed the app Instagram.
Later that same year, Apple named Instagram the iPhone App of the Year. Soon after, Kevin sold Instagram to Facebook for $1 billion. Kevin faced – and succeeded at – something most entrepreneurs will encounter eventually: the pivot.
Pivoting is one of the scariest challenges a founder can face. Pivots require you to rethink everything about your company, from teams to financing to technology and more. Chances are, you’ll need to pivot at some point – entrepreneurs rarely get it all right on their first try. Kevin didn’t, and neither did Kass and Mike.
Why pivot? There can be many reasons. The market for your product might turn out to be smaller than you thought, or a new opportunity crops up that you feel well-suited for. Perhaps a shift in technology threatens your product, or a new government regulation changes your operation.
Many entrepreneurs avoid pivoting out of fear. You can’t control fear itself, but you can control your response to it. If you’re grappling with a big decision, Mike advises asking yourself one simple question: What’s the worst thing that can happen if you do this? Usually, the worst-case scenario isn’t actually that bad – and it’s much better than staying stuck.
Buddy Media pivoted twice before landing on a successful model, which enabled their exit in 2012. But even when they did succeed, the price was high.
This brings us to the last lesson about the shit-shoveling life of the entrepreneur.
In May 2012, Mike got a life-changing phone call from Salesforce’s corporate development team. Salesforce wanted to buy Buddy Media for close to a billion dollars. When Mike heard that news, he should have been thrilled. Instead, he felt numb. His family life was in shambles, his health was declining, and he’d recently received crushing feedback from a leadership coach. Now he was being offered a life-changing amount of money.
The sale was his and Kass’s chance to heal, and they took it. The moment of celebration in June was pure, ecstatic euphoria. Mike received a standing ovation in a Soho hotel ballroom full of Buddy Media employees, while Kass cheered from the front row, her eyes radiating joy. They’d shoveled for 18 years together. And, at least in that moment, it all seemed worth it – despite their family life being a trainwreck.
For them as well as you, thriving as an entrepreneur means learning to love the shovel. Only that love of the daily grind and hard work will enable you to endure the crap you’re bound to encounter along the way. If you decide to follow this path, you’re signing up for long years of unglamorous, thankless work. But in exchange you’ll have purpose and fulfillment in droves. If you already know you love the shovel, what are you waiting for? Get shoveling!
The main takeaway of this lesson to Shoveling $h!t by Kass and Michael Lazerow is that being an entrepreneur isn’t glamorous – it involves a lot of hard work, stress, tradeoffs… and crap. But just like the world’s greatest artists have been inspired by romantic love, the world’s greatest entrepreneurs have been inspired by shit-shoveling, and their companies have reshaped the world.
Kass and Mike treat shit-shoveling as a beloved endeavor they share in every business stage: from fundraising to hiring to marketing and pivoting, and all the steps in between. If you, too, are a shovel-lover, the entrepreneurial life may be for you.
Shoveling $h!t (2025) is an honest look at the realities of being an entrepreneur. Too many entrepreneurs walk into the business world, not realizing it involves a lot more shit-shoveling and less champagne-popping than social media would have them think. Fortunately, you can go in prepared thanks to these lessons from high-growth founders who’ve just about seen it all.
Shoveling $h!t
Did you know that nearly one in five adults around the world are in the process of creating a business? Five and a half million new businesses were launched in 2023 alone!
If you’re here, you’re probably one of these folks – or you’ve fantasized about becoming one. You’ve imagined a glorious future where you get to choose your own hours, make lots of money, and generally be in charge of what gets done when.
The thing is, this fantasy is just that – a fantasy. Sure, being a business owner definitely comes with more freedom than your typical 9-to-5, and there can be significant financial payoff. But there’s also a lot of crap to shovel throughout the process. A global pandemic could suddenly shut down your brick-and-mortar, or there could be a market crash that hurts your ability to get funding, or a family member could sue you after investing.
The crap-shoveling never ends – it’s an eternal part of the entrepreneurial life. The best advice this lesson can give you? Learn to love it.
In the next sections, you’ll get an honest look at what being an entrepreneur is really like, from the perspective of Kass and Mike Lazerow – a married couple who’ve started several successful companies together and invested in many more. You won’t get a comprehensive how-to for starting a business. But you will hear about the less-glamorous truths that’ll help prepare you for when shit hits the fan.
Kass had just been wheeled into the recovery room after undergoing an emergency C-section. Thankfully, their newborn son, Cole, had been delivered healthy. Kass, however, wasn’t doing so well. Before the surgery, the epidural she’d received had clotted in her brain. This caused stroke-like symptoms – the entire left side of her body had drooped and gone numb.
She was idly wondering whether her face would permanently be stuck like that when her husband and cofounder, Mike, gingerly placed a laptop on her stomach. “I hate to say this right now,” Mike said, “but Buick needs their ads up.”
The most important ads of their career were scheduled to go live. The 68th Masters Tournament would begin in four days, and professional golf tournaments played a huge role in the profitability of their company, Golf.com. There was no wiggle room. If Mike didn’t sell ads, and if Kass didn’t traffic and manage them, they’d have no revenue. No revenue, no company.
Mike tried to cover for Kass when she went into labor early, but he didn’t know how to do her part of the job. So, just minutes after giving birth, she logged into the management platform and turned on the ads while Mike sung her praises.
Hearing this, you might be shocked and a little horrified. How could Kass and Mike have been worried about their revenue at a time like that?
But from Kass and Mike’s perspective, that’s how entrepreneurship works – for better or worse. This situation was far from an anomaly. When their first son was born, Kass took less than a week of maternity leave. Then, it was in the hospital after their third child was born that Mike had the idea for their next company, Buddy Media.
As an entrepreneur, you have to accept that doing something meaningful to you comes at a cost. In Kass’s view, you can only do one thing really well at a time. If that one thing is starting and growing a business, then your relationships will suffer. Likewise, if relationships are the priority, your business will suffer.
Kass and Mike definitely felt the impact of prioritizing their business. They weren’t there for their kids as much as they would have wanted – though they never missed one of their kids’ plays, rehearsals, or games, they were always tired, never fully present. Plus, they developed almost no meaningful friendships outside of work, and both experienced major health issues. They couldn’t fully take care of themselves physically, mentally, or emotionally.
Are you willing to embrace these realities? If not, you probably shouldn’t become an entrepreneur. But if you are, there are ways of managing the imbalance as best you can.
For Kass and Mike, they openly discussed and agreed about sacrificing time with their kids when they were young so that they would hopefully get more time with them later. They chose to focus on financial success to provide their kids with a better life and to improve the world through philanthropy. That wasn’t necessarily the right decision – but it was a conscious one made through honest communication.
Before taking the plunge and starting a business, do a lot of self-reflection and make sure the tradeoffs are ones you’re willing to make. Remember: you will sacrifice some combination of friendships, family, and health. Are you still ready to grab that shovel?
Aspiring business owners tend to spend a lot of time focused on the cofounder question – that is, whether they should have one.
The truth is, success or failure isn’t guaranteed either way. On the one hand, 80 percent of all billion-dollar startups have two or more founders. On the other, companies with solo founders tend to survive longer and generate more revenue. That’s why Kass and Mike believe it’s not really about having a cofounder or not – it’s about having the right one if you choose to go in that direction.
It’s a lot like picking your spouse. Your cofounder is the first person you talk to at the start of the workday, the person you vent to, and the person you celebrate with. So, you want to be sure you’re with the right person. How? It helps to assess whether you’re on the same page with your vision, values, communication, mindset, and workload.
First, founders need to agree on vision – where they want to go. They should also agree on values. Is your cofounder willing to cut corners you would never cut? If so, it’s good to try and find that out in advance. Also, how does your cofounder prioritize their values? Say your cofounder deeply values family, and she has three kids and an ailing parent. How might that affect her commitment to the business?
Communication is also essential. You need to be able to openly give honest, constructive feedback and discuss difficult issues. A whopping 65 percent of startups fail due to founder conflict. If you can’t handle regular disagreements, you won’t be able to handle the big “Oh shit” moments either.
Strong partnerships require a shared growth mindset – the belief that talent can be developed through hard work, good strategies, and input from others. Cofounders should both believe in each other’s ability to embrace challenges, learn from criticism, and get inspired.
Finally, cofounders need to share the workload and be equally committed to doing what it takes for the company to succeed. This doesn’t mean performing identical tasks – definitely play to your strengths. But you don’t want a relationship where you’re doing 90 percent of the work. That’s a recipe for resentment, and it’s demotivating for your employees.
This approach applies to hiring your employees, too. A company’s first 20 employees contribute to the soul of your business and set the tone for all future hires. Your initial hires should fill in the gaps the cofounders can’t and should be tied to your biggest priorities.
For example, Buddy Media’s hiring strategy was based on customer needs. Their initial business model involved building apps, which required specific technical skills. So, they prioritized hiring engineers.
If you get it right with the first batch of employees, you get them to bring in their friends. At Buddy Media, employees were given a sizable bonus for every referral – as well as a coveted position on the referrals leaderboard. These incentives ensured everyone knew how important hiring was, which ultimately saved the company a lot of money and time.
Sweetgreen’s product concept was pretty simple: they wanted to offer food that was both healthy and convenient. The company was born from three Georgetown college students’ dissatisfaction with campus food options, which failed to balance speed, price, and nutritional value.
Today, Sweetgreen is worth about $861.1 billion dollars. How’d they do it? Simple: they answered the questions on the “Go Gauge.” The Go Gauge is a measure that Kass and Mike use to determine whether to invest in an early-stage project. It involves just six questions. But without solid answers to all of them, funding is a no-go.
Entrepreneurs are often instructed to make a 30- or 40-page business plan with a bunch of different sections and appendices. But in Kass and Mike’s view, less is more. A clear, one-page set of answers to a few key questions helps them – and you – focus on the pure vision needed to invest time or money into an idea.
The six questions on the Go Gauge relate to six key areas: product, differentiation, customer, sales and marketing, delivery, and financial model.
We’ve already discussed Sweetgreen’s product – healthy, convenient food. But what differentiated it? It was simply better than anything else that existed. When it first opened in 2007, there weren’t many quick-serve restaurants with healthy options. For your company, differentiation could mean being faster, cooler, smaller, bigger, cheaper, or fancier.
The next element in the Go Gauge is your customer. Who’s your audience? Sweetgreen targeted consumers who value healthy food, convenience, and reasonable prices. Relatedly, what size is your market? Sweetgreen’s founders knew there was a huge market for people who eat out regularly – three out of five Americans go out for dinner at least once a week and, on average, order delivery 4.5 times a month! It’s good to consider roughly how many potential customers exist, because that number needs to be big enough to justify the size of the company you’re building.
Fourth is sales and marketing. Customers won’t find you on their own – you need a plan for reaching them via marketing and advertising. You might only sell directly to consumers online, like the companies Wayfair and Chewy. Or you might only have physical stores, like smaller retailers.
Along similar lines, you need to consider delivery – how will you get your product to your customers? For Sweetgreen, it was their restaurants. For other companies, it might be through an app store.
Last but not least, there’s the financial model. This bit makes all the difference. On its surface, it’s straightforward: calculate the revenue you expect to get from customers and what you expect to spend making your products and running your company. Unfortunately, entrepreneurs tend to grossly overestimate their revenue and underestimate their costs. So, after you’re done creating your financial model, cut the revenue in half and then double the expenses. It’s much better to exceed your projections than to fall short.
What’s the one thing that can take any company down? That’s right – running out of money. Just like a baby can’t survive without food, your company can’t survive without cash. That’s why Kass and Mike like to say that the first three jobs of an entrepreneur are: don’t run out of money, don’t run out of money, and don’t run out of money.
Hoping that you suddenly generate more revenue is never a strategy. You need to focus your efforts on concrete ways of getting funds – and that means fundraising. Yes, fundraising can feel scary and awkward. But embrace the crap, because you’re going to have to do it.
Fundraising starts with your mentality. The most important thing is believing in your company and yourself. Think about it like this: you’re not asking for money, you’re offering investors an opportunity. In the end, the worst thing that can happen is that they say no.
Founders typically end up paying for the startup costs themselves, at least initially. That’s what Kass and Mike did to get Golf.com off the ground – buying computers, software licenses, office supplies, and so on. For you, this might mean leasing a space for a restaurant or hiring engineers. Also, know that you’ll likely have to forego a salary and work out of an apartment or garage – just like the founders of Google, Apple, Amazon, and Disney.
By investing what you can early on, you’re showing investors you’re sharing the financial risks. But when your business needs more than you have, look to outside sources: angel investors like friends, colleagues, and family; venture capital firms; strategic investors; lending institutions; grants; or corporate programs.
Friends, colleagues, and family members are your first source as a first-time entrepreneur. Each of Jeff Bezos’s siblings invested $10,000 in Amazon – now, each stake is worth more than $1 billion. But remember, things don’t always work out as planned. When friends and family invest, you’re risking your relationships as well as their money. Be sure to overcommunicate about risks and timelines, and assure them they should only invest money they’re willing to lose.
If you’re raising venture capital, remember that VCs are professional investment firms whose primary responsibility is stewarding their investors’ money. They know a lot more about deal terms than you do and will act in their investors’ best interest when things go sideways.
So choose your partners deliberately. Find ones who share your values and vision, offer simple and mutually beneficial terms, and provide tangible value. Finally, avoid “shotgun marriages” with VCs who are trying to get you locked into an unfavorable commitment.
One final bit of advice: always be in fundraising mode. This doesn’t necessarily mean you’re actively raising money at all times, but it does mean expanding your network and building relationships. Show people you care about them, regardless of what they might give you in return.
In the 1950s, Stanford MBA student Phil Knight believed the American fitness industry was about to explode. He wrote his thesis on the athletic shoe market and eventually went on to found the company Nike.
But before Nike became the company we know today, Knight had to do a lot of shoveling. First, he traveled to Japan and convinced the head of Tiger running shoes to give him the exclusive right to sell their shoes in the western United States. Then he started selling the shoes out of the back of his car at track events. Today, Nike generates $50 billion in annual revenue. But the first $1 million came from Knight’s hyperfocus on his main priority: selling shoes.
Knight’s example proves that hyperfocusing from the start is critical to a business’s long-term success. With the right planning and focus, you can prioritize the few most important aspects of your business and execute them well.
To determine your company’s priorities, first imagine you have a gallon jug. You need to fill it with big rocks, sand, and pebbles. If you start with the small stuff – the sand and pebbles – you won’t fit all the big rocks inside. That changes if you start with the big rocks instead, then add the sand and pebbles to fill in the gaps.
This is a metaphor for your company’s priorities. The big rocks are your organizational priorities – the stuff that should be taking up most of your time and bandwidth. What these are exactly depends on your business, but they could include sales, hiring, or expanding to new markets.
The pebbles are things that will matter in the next twelve months. For Buddy Media, these included meeting with potential investors, having breakfast with potential future employees, and brainstorming product extensions. None of them were immediately critical, but they all mattered later on.
Finally, the sand is all the small stuff that doesn’t differentiate your business but nevertheless needs to get done. It’s paying payroll, filing taxes, and closing the financials.
Once you’ve determined your priorities, you can create a plan. Without a plan, you have no idea where you’re going and what success looks like. Your plan should include attainable, specific, relevant, and time-bound goals. Every rock you prioritize needs an associated metric that will tell you whether or not you succeeded. For instance, if sales are the number one goal, how do you know whether you’re doing well? If you’re focused on hiring, it’s how many people, what types of people, and by when?
Don’t forget to write your plans down! If you and your employees can’t refer to the plan at any time, your plan doesn’t actually exist. Coming up with the plan, and then acting on it, is a key part of your everyday shoveling. By hyperfocusing on your most important priorities, you ensure you’re not spreading yourself too thin and that you can execute as well as possible.
Before Instagram became Instagram, it was a little-known app called Burbn. Burbn was essentially a gamified version of the location app Foursquare, in which users earned points for checking into local businesses. Its founder, Kevin Systrom, created it as a side project while learning to code.
Burbn wasn’t exactly a hit. Nonetheless, Kevin didn’t quit. He believed Burbn had a unique feature – the one that allowed users to post pictures with friends. So he stripped away almost everything from the app except for that feature, plus the ability to add a filter, like, and comment on photos. He renamed the app Instagram.
Later that same year, Apple named Instagram the iPhone App of the Year. Soon after, Kevin sold Instagram to Facebook for $1 billion. Kevin faced – and succeeded at – something most entrepreneurs will encounter eventually: the pivot.
Pivoting is one of the scariest challenges a founder can face. Pivots require you to rethink everything about your company, from teams to financing to technology and more. Chances are, you’ll need to pivot at some point – entrepreneurs rarely get it all right on their first try. Kevin didn’t, and neither did Kass and Mike.
Why pivot? There can be many reasons. The market for your product might turn out to be smaller than you thought, or a new opportunity crops up that you feel well-suited for. Perhaps a shift in technology threatens your product, or a new government regulation changes your operation.
Many entrepreneurs avoid pivoting out of fear. You can’t control fear itself, but you can control your response to it. If you’re grappling with a big decision, Mike advises asking yourself one simple question: What’s the worst thing that can happen if you do this? Usually, the worst-case scenario isn’t actually that bad – and it’s much better than staying stuck.
Buddy Media pivoted twice before landing on a successful model, which enabled their exit in 2012. But even when they did succeed, the price was high.
This brings us to the last lesson about the shit-shoveling life of the entrepreneur.
In May 2012, Mike got a life-changing phone call from Salesforce’s corporate development team. Salesforce wanted to buy Buddy Media for close to a billion dollars. When Mike heard that news, he should have been thrilled. Instead, he felt numb. His family life was in shambles, his health was declining, and he’d recently received crushing feedback from a leadership coach. Now he was being offered a life-changing amount of money.
The sale was his and Kass’s chance to heal, and they took it. The moment of celebration in June was pure, ecstatic euphoria. Mike received a standing ovation in a Soho hotel ballroom full of Buddy Media employees, while Kass cheered from the front row, her eyes radiating joy. They’d shoveled for 18 years together. And, at least in that moment, it all seemed worth it – despite their family life being a trainwreck.
For them as well as you, thriving as an entrepreneur means learning to love the shovel. Only that love of the daily grind and hard work will enable you to endure the crap you’re bound to encounter along the way. If you decide to follow this path, you’re signing up for long years of unglamorous, thankless work. But in exchange you’ll have purpose and fulfillment in droves. If you already know you love the shovel, what are you waiting for? Get shoveling!
The main takeaway of this lesson to Shoveling $h!t by Kass and Michael Lazerow is that being an entrepreneur isn’t glamorous – it involves a lot of hard work, stress, tradeoffs… and crap. But just like the world’s greatest artists have been inspired by romantic love, the world’s greatest entrepreneurs have been inspired by shit-shoveling, and their companies have reshaped the world.
Kass and Mike treat shit-shoveling as a beloved endeavor they share in every business stage: from fundraising to hiring to marketing and pivoting, and all the steps in between. If you, too, are a shovel-lover, the entrepreneurial life may be for you.
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