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Self-Made Boss: Advice, Hacks, and Lessons from Small Business Owners
Part starter-kit, part encyclopedia, and part inspiration, Self-Made Boss is an essential survival guide for small businesses
When it comes to getting practical advice, small business owners too often don't know where to look. Sure, you can find all sorts of high-level strategic tips from Fortune 500 CEOs. But what if you own a restaurant, and you're trying to figure out how to source good fish, or if you're looking to increase revenue from your plumbing supply store? You'll be running a lot of Google searches before you hear from someone who's actually stood in your shoes.
Longtime Square executives Jackie Reses and Lauren Weinberg want to change this. So they reached out across the country, talking to dozens of entrepreneurs with valuable businesses--and invaluable advice. This book is the product of that research. Part starter-kit, part encyclopedia, part inspiration, Self-Made Boss is filled with information not just about who these small business owners are, but how they built their companies, step by step.
How did they get their start? When did they decide to hire more staff? How did they set a course for growth? And when problems arose, how did they fight through them? You'll hear from a second-generation ice cream shop owner on how to manage price increases; an oyster farmer finding new ways to stay afloat in the middle of a global pandemic; a roofer who refused to be denied or defined by her race and gender--and dozens of other small business owners making a big difference in their communities.
No matter the size of your business today--or where you're thinking about taking the jump tomorrow--you'll find answers you can apply right away.
Because there's a common purpose that all small business owners share: the drive to build something from the ground up; the relentless pursuit of turning obstacles into opportunities and roadblocks into stepping stones. It's tough and messy, hard-fought and hard-won. And above all, it's something you can't have when you work anywhere else--or for anyone else.
That's what it means to be a Self-Made Boss.
When it comes to getting practical advice, small business owners too often don't know where to look. Sure, you can find all sorts of high-level strategic tips from Fortune 500 CEOs. But what if you own a restaurant, and you're trying to figure out how to source good fish, or if you're looking to increase revenue from your plumbing supply store? You'll be running a lot of Google searches before you hear from someone who's actually stood in your shoes.
Longtime Square executives Jackie Reses and Lauren Weinberg want to change this. So they reached out across the country, talking to dozens of entrepreneurs with valuable businesses--and invaluable advice. This book is the product of that research. Part starter-kit, part encyclopedia, part inspiration, Self-Made Boss is filled with information not just about who these small business owners are, but how they built their companies, step by step.
How did they get their start? When did they decide to hire more staff? How did they set a course for growth? And when problems arose, how did they fight through them? You'll hear from a second-generation ice cream shop owner on how to manage price increases; an oyster farmer finding new ways to stay afloat in the middle of a global pandemic; a roofer who refused to be denied or defined by her race and gender--and dozens of other small business owners making a big difference in their communities.
No matter the size of your business today--or where you're thinking about taking the jump tomorrow--you'll find answers you can apply right away.
Because there's a common purpose that all small business owners share: the drive to build something from the ground up; the relentless pursuit of turning obstacles into opportunities and roadblocks into stepping stones. It's tough and messy, hard-fought and hard-won. And above all, it's something you can't have when you work anywhere else--or for anyone else.
That's what it means to be a Self-Made Boss.
- GenresBusinessNonfiction
256 pages, ebook
Published March 29, 2022
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June 30, 2022If you have an itch to strike out on your own and start a small business, you’re in great company.
Self-made bosses are daring individuals who see problems in the world and decide to become part of the solution. Some are creatives looking to turn passion into a profession; others are just inspired to give back to their community. No matter what, they’re people with the drive to build something from the ground up.
To turn your spark of inspiration into a successful business, get practical. Get in touch with your local SMB and access their free business resources, then build your business plan, incorporate, and standardize your workflows. Then focus on creating a signature experience that keeps your customers coming back. Finally, stay flexible and observant, and you and your business will be in it for the long haul.
---
Outline your vision and articulate your goals by writing a solid business plan.
Let’s not sugarcoat it: starting a small business is risky. You have about a fifty-fifty chance of surviving the first five years; in fact, one small business in five will fold within its first year. To prevent this, it’s absolutely critical to think through your venture systematically. And that’s what a business plan is for.
Now, a business plan is crucial if you’re looking for a grant or a loan. As an outward-facing document, it can help you convince people that you’re taking the venture seriously and that you know what you’re doing.
But even if you’re not looking for external funding, it’s a great idea to write a business plan anyway, even if it’s just for yourself. A business plan is your chance to present your vision for what you’re building and outline your plans for achieving your goals. Simply put, it’s the blueprint for your business. And the act of writing a business plan requires you to research your industry and think objectively about what goals you’re aiming to achieve. The thought process behind it will positively influence your entire business and get you started on the right track. So don’t procrastinate on this one – it isn’t just busywork!
So how do you do it? Fortunately, you won’t need to reinvent the wheel every time – it’s a pretty formulaic process, and there are plenty of resources online – and in the library – for the specifics of how to do it. But here are some tips to get you started:
The beginning of your business plan, the executive summary, is your chance to tell your story vividly and engagingly. In it, briefly run through what the rest of your plan lays out in detail, with particular focus on the problem, solution, and audience. Pro tip: the executive summary will go first in the document, but it might be easier to write it last. But whenever you choose to write it, remember – to convince your readers, the executive summary has to be punchy!
Then, for the rest of the document, get much more concrete and objective. Write like a banker, not a poet; back up your claims with evidence and statistics, and don’t make claims you can’t prove – that you make the best sub sandwiches in town, for example. Be selective with your information and be sure to present yourself and your team in the best possible light.
If you’re aiming your business plan at investors, it’s a good idea to hire an accountant to help you make realistic financial projections and to put everything in the format your audience is expecting. And don’t send gimmicks along with the business plan! Investors will gladly eat the baked goods in your gift basket, but the money you spend on those treats isn’t a smart expenditure – they’re unlikely to sway anyone, and they might just make you look less than serious. Just stick to the facts instead.
What’s important is that you succinctly articulate the problem or need you’re looking to address, and why anyone would pay for your solution. Is your potential business not just feasible, but attractive to potential customers? Answering this question for yourself and for potential investors is at the core of a solid business plan.
---
Take care of your incorporation paperwork and other licensing requirements from the outset.
Unless you’re opening a law firm, chances are, you’re not starting a business in order to do legal paperwork – that isn’t most people’s idea of fun! But if you want your business to be aboveboard, it can’t be avoided. Given that, you might as well knock it out as quickly as possible so you can focus on running your business. It’ll also help you avoid fines or even your business getting shut down later on down the line.
Fortunately, incorporating your business isn’t as painful as it sounds. To begin, you’ll need to decide on your corporate structure. This will determine the parameters of your business and how it will be taxed. Here, we’ll outline the basics so you can get the lay of the land, but it’s a good idea to do your own web research and follow up with a lawyer to get a full picture of the pros and cons of each. Also note that how you incorporate your business might vary from state to state.
First, there’s the simplest form of incorporation: sole proprietorship. This means that only you own the business, and in most cases you only need to file one form, the DBA, or “Doing Business As” form. A sole proprietorship is a pass-through entity, meaning that corporate profits are only taxed once as part of the owner’s income. They’re super easy to set up, so it might make sense to start here and change your structure later if you need to. The downside to a sole proprietorship, though, is that you’re 100% responsible for any business liabilities or debts incurred.
Next up, you have the LLC, or limited liability corporation. It’s a little more complicated than a sole proprietorship, but it’s likely that you can take care of the paperwork in about two hours. The advantages of an LLC are that as many people as you like can own the business and personal assets are protected. Should your business flop, you won’t stand to lose your retirement fund or your house!
If an LLC is sounding like the right option for you, also look into structuring your business as an S corp, which is similar to an LLC except that it has more formalities. An S corp’s advantage over an LLC is that S corps have been around longer, so certain investors, lawyers, and advisors might prefer to work with you.
Finally, if you’re looking to one day raise capital by selling shares of your business, you’ll need to incorporate as a C corporation. A C corp allows for multiple types of stock shares and unlimited shareholders. There’s a disadvantage to it too, though – unlike the other three structures, which are all pass-through entities, a C corp is taxed twice. Given the increased tax burden, don’t set up a C corp unless you’re sure it’s the right option for you.
You’ll need a lawyer to set up an S corp or a C corp, unlike for a sole proprietorship or LLC. But even for those, you can always hire a lawyer – if you’re worried you’re in over your head, that could mean peace of mind.
Finally, be sure to look into what licenses and insurance you need for your industry. An insurance broker can help you with this.
---
When designing your operational workflows, use observation and standardization to your advantage.
Now let’s get to why you’re really here: learning how to get up and running!
The real question here is: how do you turn your idea into a finished product in the hands of a customer? Essentially, we’re talking about process management of your operations. Small businesses typically have small margins, so the successful ones pay close attention to every aspect of how the company is run. That means getting really specific with the nitty gritty details of your workflows and optimizing for efficiency.
To nail down your operations, use data to your advantage. Take the time to observe and document your operational processes – everything from sourcing materials to inventory management, distribution, and sales processes. Anything that’s done routinely should be standardized and documented, then systematized. A documented, standardized workflow will be hugely helpful in identifying problems or inefficiencies and will help you test new solutions. Plus, having clear and documented workflows will make it easier to train new employees or sell your business to someone else at a later date.
Want an example? Let’s look at Pesso’s Ices & Ice Cream in Bayside, New York, run by a father and a son. The younger Pesso took a long and close look at all aspects of their business – from ingredients to spoon prices to hiring practices – and made educated guesses about how to improve the business.
When he noticed that the shop barely made any money before two o’clock, he decided to change the opening hours. He also ran a full cost analysis and realized that despite ingredient costs rising dramatically in a few years, his shop hadn’t adjusted the prices of their ice cream. He changed the price and sizing of the scoops, and stopped offering less popular menu items like floats, which took more work than scooping ice cream but generated little revenue. A few customers complained, but most didn’t notice. Some even appreciated it, reporting that fewer choices had reduced their decision fatigue. For Pesso, a simpler menu allowed him to focus on quality and also boosted his margins.
Nowadays, Pesso is a small business consultant. Based on his success with the ice cream shop, he advises other business owners to observe your systems first, from multiple angles, then simplify.
The more data you have on your processes, the more easily you’ll be able to go from reactive to predictive. You’ll be able to adapt to changing customer demands more nimbly, because you’ll be able to observe trends. As Mike Bloomberg once quipped, “In God we trust. Everyone else: bring data.”
---
To stay ahead of unexpected setbacks, observe consumer trends and be flexible in your approach to business.
Let’s say your business is official and you’ve been around for several months. Customers are regularly coming through the door, and you feel like you’ve nailed down your operational procedures. Maybe you’re even profitable already.
Unfortunately, this smooth sailing probably won’t last long. You’ll likely confront a business disruption that can come in many different forms, ranging from everyday setbacks like traffic jams and unreliable employees to larger-scale issues like changing consumer behavior or world events like wars and pandemics. But don’t lose heart! There are a couple of ways to prepare yourself to roll with the punches.
The first is to be observant. Keep a close eye on your company’s sales information, and compare it to consumer trends and feedback from customers. Some setbacks, like a hurricane, will sneak up on you. But more often, changes that commonly affect business happen gradually. If you learn to read your market and pay attention to trends, you can adapt your business accordingly.
The second is to be flexible. The ability to pivot might be the most important key to success. Keep asking yourself how you can adapt or improve, and stay committed to evolving your business.
Being observant and flexible will help you find new opportunities in business if your initial approach isn’t working. One way is to create an adjacent product if yours isn’t selling for one reason or another. Let’s say that, pre-pandemic, you found success selling homemade festival fashion on Etsy, an online craft marketplace. Your Coachella-ready crop tops were flying off the shelves in 2019, but by the spring of 2020, when pretty much all festivals worldwide were canceled, business wasn’t exactly booming.
In April 2020, the pandemic was well underway and Etsy executives sent a memo to its sellers, suggesting that they all make masks. It was good advice, and you’d have been wise to take it. In just a few short months, mom-and-pop shops sold $500 million worth of masks – a product for which there had previously been almost no demand.
When you encounter your first roadblock, ask yourself whether it’s time to double down on your vision or to recalibrate your approach. Remember to let the data do the talking, and don’t operate solely on gut feelings. Consider reaching out to an expert in your industry to talk about the challenge you’re facing.
Self-made bosses are daring individuals who see problems in the world and decide to become part of the solution. Some are creatives looking to turn passion into a profession; others are just inspired to give back to their community. No matter what, they’re people with the drive to build something from the ground up.
To turn your spark of inspiration into a successful business, get practical. Get in touch with your local SMB and access their free business resources, then build your business plan, incorporate, and standardize your workflows. Then focus on creating a signature experience that keeps your customers coming back. Finally, stay flexible and observant, and you and your business will be in it for the long haul.
---
Outline your vision and articulate your goals by writing a solid business plan.
Let’s not sugarcoat it: starting a small business is risky. You have about a fifty-fifty chance of surviving the first five years; in fact, one small business in five will fold within its first year. To prevent this, it’s absolutely critical to think through your venture systematically. And that’s what a business plan is for.
Now, a business plan is crucial if you’re looking for a grant or a loan. As an outward-facing document, it can help you convince people that you’re taking the venture seriously and that you know what you’re doing.
But even if you’re not looking for external funding, it’s a great idea to write a business plan anyway, even if it’s just for yourself. A business plan is your chance to present your vision for what you’re building and outline your plans for achieving your goals. Simply put, it’s the blueprint for your business. And the act of writing a business plan requires you to research your industry and think objectively about what goals you’re aiming to achieve. The thought process behind it will positively influence your entire business and get you started on the right track. So don’t procrastinate on this one – it isn’t just busywork!
So how do you do it? Fortunately, you won’t need to reinvent the wheel every time – it’s a pretty formulaic process, and there are plenty of resources online – and in the library – for the specifics of how to do it. But here are some tips to get you started:
The beginning of your business plan, the executive summary, is your chance to tell your story vividly and engagingly. In it, briefly run through what the rest of your plan lays out in detail, with particular focus on the problem, solution, and audience. Pro tip: the executive summary will go first in the document, but it might be easier to write it last. But whenever you choose to write it, remember – to convince your readers, the executive summary has to be punchy!
Then, for the rest of the document, get much more concrete and objective. Write like a banker, not a poet; back up your claims with evidence and statistics, and don’t make claims you can’t prove – that you make the best sub sandwiches in town, for example. Be selective with your information and be sure to present yourself and your team in the best possible light.
If you’re aiming your business plan at investors, it’s a good idea to hire an accountant to help you make realistic financial projections and to put everything in the format your audience is expecting. And don’t send gimmicks along with the business plan! Investors will gladly eat the baked goods in your gift basket, but the money you spend on those treats isn’t a smart expenditure – they’re unlikely to sway anyone, and they might just make you look less than serious. Just stick to the facts instead.
What’s important is that you succinctly articulate the problem or need you’re looking to address, and why anyone would pay for your solution. Is your potential business not just feasible, but attractive to potential customers? Answering this question for yourself and for potential investors is at the core of a solid business plan.
---
Take care of your incorporation paperwork and other licensing requirements from the outset.
Unless you’re opening a law firm, chances are, you’re not starting a business in order to do legal paperwork – that isn’t most people’s idea of fun! But if you want your business to be aboveboard, it can’t be avoided. Given that, you might as well knock it out as quickly as possible so you can focus on running your business. It’ll also help you avoid fines or even your business getting shut down later on down the line.
Fortunately, incorporating your business isn’t as painful as it sounds. To begin, you’ll need to decide on your corporate structure. This will determine the parameters of your business and how it will be taxed. Here, we’ll outline the basics so you can get the lay of the land, but it’s a good idea to do your own web research and follow up with a lawyer to get a full picture of the pros and cons of each. Also note that how you incorporate your business might vary from state to state.
First, there’s the simplest form of incorporation: sole proprietorship. This means that only you own the business, and in most cases you only need to file one form, the DBA, or “Doing Business As” form. A sole proprietorship is a pass-through entity, meaning that corporate profits are only taxed once as part of the owner’s income. They’re super easy to set up, so it might make sense to start here and change your structure later if you need to. The downside to a sole proprietorship, though, is that you’re 100% responsible for any business liabilities or debts incurred.
Next up, you have the LLC, or limited liability corporation. It’s a little more complicated than a sole proprietorship, but it’s likely that you can take care of the paperwork in about two hours. The advantages of an LLC are that as many people as you like can own the business and personal assets are protected. Should your business flop, you won’t stand to lose your retirement fund or your house!
If an LLC is sounding like the right option for you, also look into structuring your business as an S corp, which is similar to an LLC except that it has more formalities. An S corp’s advantage over an LLC is that S corps have been around longer, so certain investors, lawyers, and advisors might prefer to work with you.
Finally, if you’re looking to one day raise capital by selling shares of your business, you’ll need to incorporate as a C corporation. A C corp allows for multiple types of stock shares and unlimited shareholders. There’s a disadvantage to it too, though – unlike the other three structures, which are all pass-through entities, a C corp is taxed twice. Given the increased tax burden, don’t set up a C corp unless you’re sure it’s the right option for you.
You’ll need a lawyer to set up an S corp or a C corp, unlike for a sole proprietorship or LLC. But even for those, you can always hire a lawyer – if you’re worried you’re in over your head, that could mean peace of mind.
Finally, be sure to look into what licenses and insurance you need for your industry. An insurance broker can help you with this.
---
When designing your operational workflows, use observation and standardization to your advantage.
Now let’s get to why you’re really here: learning how to get up and running!
The real question here is: how do you turn your idea into a finished product in the hands of a customer? Essentially, we’re talking about process management of your operations. Small businesses typically have small margins, so the successful ones pay close attention to every aspect of how the company is run. That means getting really specific with the nitty gritty details of your workflows and optimizing for efficiency.
To nail down your operations, use data to your advantage. Take the time to observe and document your operational processes – everything from sourcing materials to inventory management, distribution, and sales processes. Anything that’s done routinely should be standardized and documented, then systematized. A documented, standardized workflow will be hugely helpful in identifying problems or inefficiencies and will help you test new solutions. Plus, having clear and documented workflows will make it easier to train new employees or sell your business to someone else at a later date.
Want an example? Let’s look at Pesso’s Ices & Ice Cream in Bayside, New York, run by a father and a son. The younger Pesso took a long and close look at all aspects of their business – from ingredients to spoon prices to hiring practices – and made educated guesses about how to improve the business.
When he noticed that the shop barely made any money before two o’clock, he decided to change the opening hours. He also ran a full cost analysis and realized that despite ingredient costs rising dramatically in a few years, his shop hadn’t adjusted the prices of their ice cream. He changed the price and sizing of the scoops, and stopped offering less popular menu items like floats, which took more work than scooping ice cream but generated little revenue. A few customers complained, but most didn’t notice. Some even appreciated it, reporting that fewer choices had reduced their decision fatigue. For Pesso, a simpler menu allowed him to focus on quality and also boosted his margins.
Nowadays, Pesso is a small business consultant. Based on his success with the ice cream shop, he advises other business owners to observe your systems first, from multiple angles, then simplify.
The more data you have on your processes, the more easily you’ll be able to go from reactive to predictive. You’ll be able to adapt to changing customer demands more nimbly, because you’ll be able to observe trends. As Mike Bloomberg once quipped, “In God we trust. Everyone else: bring data.”
---
To stay ahead of unexpected setbacks, observe consumer trends and be flexible in your approach to business.
Let’s say your business is official and you’ve been around for several months. Customers are regularly coming through the door, and you feel like you’ve nailed down your operational procedures. Maybe you’re even profitable already.
Unfortunately, this smooth sailing probably won’t last long. You’ll likely confront a business disruption that can come in many different forms, ranging from everyday setbacks like traffic jams and unreliable employees to larger-scale issues like changing consumer behavior or world events like wars and pandemics. But don’t lose heart! There are a couple of ways to prepare yourself to roll with the punches.
The first is to be observant. Keep a close eye on your company’s sales information, and compare it to consumer trends and feedback from customers. Some setbacks, like a hurricane, will sneak up on you. But more often, changes that commonly affect business happen gradually. If you learn to read your market and pay attention to trends, you can adapt your business accordingly.
The second is to be flexible. The ability to pivot might be the most important key to success. Keep asking yourself how you can adapt or improve, and stay committed to evolving your business.
Being observant and flexible will help you find new opportunities in business if your initial approach isn’t working. One way is to create an adjacent product if yours isn’t selling for one reason or another. Let’s say that, pre-pandemic, you found success selling homemade festival fashion on Etsy, an online craft marketplace. Your Coachella-ready crop tops were flying off the shelves in 2019, but by the spring of 2020, when pretty much all festivals worldwide were canceled, business wasn’t exactly booming.
In April 2020, the pandemic was well underway and Etsy executives sent a memo to its sellers, suggesting that they all make masks. It was good advice, and you’d have been wise to take it. In just a few short months, mom-and-pop shops sold $500 million worth of masks – a product for which there had previously been almost no demand.
When you encounter your first roadblock, ask yourself whether it’s time to double down on your vision or to recalibrate your approach. Remember to let the data do the talking, and don’t operate solely on gut feelings. Consider reaching out to an expert in your industry to talk about the challenge you’re facing.
May 15, 2022
The authors created a wonderful book for small business owners. They highlight many local businesses around the nation and how those owners handle starting, running and even closing a business.
The book should be on the shelf of every small business owner and in arms length reach to jump to the chapters that are relevant to them. The book is meant as a resource. Read only the sections that are relevant to you. Sort of like an encyclopedia or user manual.
I learned about the book when I was listening to a live video webinar which had the author, Jackie Reses, as a panelist. Although the panel was about an entirely different topic, she mentioned her book at the end. Her former work experience at Square which is all about helping small local business was instrumental in her writing this with co-author Lauren Weinberg.
The book should be on the shelf of every small business owner and in arms length reach to jump to the chapters that are relevant to them. The book is meant as a resource. Read only the sections that are relevant to you. Sort of like an encyclopedia or user manual.
I learned about the book when I was listening to a live video webinar which had the author, Jackie Reses, as a panelist. Although the panel was about an entirely different topic, she mentioned her book at the end. Her former work experience at Square which is all about helping small local business was instrumental in her writing this with co-author Lauren Weinberg.
October 23, 2022
This book can be helpful for someone who is starting out a new business and doesn't know much about the business world. It has some great resources as well for people that start a business in the USA. However, I found it very basic and a lot of the ideas suggested are things I was already aware, which is why I gave it 3 stars. If you don't know about how to start a business, this book is helpful, so don't be dissuaded by my lower score.
January 8, 2023
I thoroughly enjoyed reading this! If you are someone like me who is skilled and experienced in their trade but doesn’t know the steps or information regarding starting up and running their own business, it’s worth the read!
September 18, 2022
Review coming soon
Read
March 25, 2024Very useful and including specific resources/ sites/ platforms to use instead of vague advice. Definitely more helpful to businesses selling physical products or looking to scale with more employees. Still helpful and sparked some ideas for my small business.
Displaying 1 - 6 of 6 reviews