Obey the Law of Category

You can hardly do better than this book on market positioning:

The 22 Immutable Laws of Marketing by Ries & Trout

Who was the first person to fly across the Atlantic? Even history haters will probably come up with Lindbergh. The second person did it faster and used less fuel. Why don’t you remember his name? Because the Law of Leadership says “It’s better to be first than it is to be better.”

Ah, but not everyone can be first, you say. Excellent point, which brings me to my personal favorite: #2 The Law of Category, which says “If you can’t be first in a category, set up a new category you can be first in.” Remember Amelia Earhart, the first female pilot to solo across the Atlantic?

This is the kind of clear-eyed insight you’ll find in this essential book for small business startups or owners who want to pivot into a new, more profitable vein.

Remarkable or Invisible

“The aim of marketing is to know and understand the customer so well the product or service fits him and sells itself.” ~ Peter Drucker

One of my all-time favorite small business marketing books:

Purple Cow by Seth Godin

It was really hard to choose which of my favorite books to put first. This one wins for the simple reason that it’s so simple:

“Be remarkable or be invisible.”

Why would you waste your time and a lot of money marketing a ho-hum product or service? If no one is excited by your offering, you’re just wasting your time and hard-earned cash by trying to advertise your way into their wallet.

Do this instead: Spend the time and money making your product or service remarkable. Then the marketing will take care of itself.

This is a fast read but if you miss the point of this book, you’re in for a lot of bumpy road in your marketing efforts.

Entrepreneur, Manager, or Technician?

There should be a class in high school just to study great quotes.

“The recipe for perpetual ignorance is: Be satisfied with your opinions and content with your knowledge.” ~ Elbert Hubbard

“You must learn from the mistakes of others. You can’t possibly live long enough to make them all yourself.” ~ Sam Levenson

I wish someone had pulled me aside in my twenties and forced me to read several books about starting and running a business. O so many bruises would have been avoided from my own stubborn trial-and-error approach. Introverted, headstrong and stubborn… I have made many mistakes along the way. Don’t do it the way I did. Save time, money, and heartache by leveraging the wisdom of others. The small business books below will save you time and scar tissue… if you apply them.

Read This First

The E-Myth Revisited by Michael Gerber

This classic work explores our real motivation for leaping into the world of the self-employed.  Gerber delivers tons of practical wisdom to help you reduce the scars of trial and error.

Timeless principles are delivered in and around the story of Sarah, who is cajoled by her friends into starting her own business.

Before she knows it, Sarah is overwhelmed and miserable. Gerber joins her as the consultant in the story and explains the various hats that every solopreneur must were in order to conduct business:

  • Entrepreneur
  • Manager
  • Technician

Read this book to get a full, mature view of what it means to start and build a business, delivered in a winsome way with concrete, practical steps to follow.

Are you a Contractor?

If your business revolves around contracting or consulting, also consider…

The E-Myth Contractor by Michael Gerber

In this follow-up to his earlier E-Myth book, Gerber unpacks the special challenges of those in the contracting & consulting trades.

Every aspect of a contract business is covered, including:

  • Money Management
  • Job Estimation
  • Work Systems
  • Sub-contractors

… and much more, told in Gerber’s  practical and approachable style.

One of my favorite quotes from the book is from the estimator on site in a prospect’s kitchen. He says to the woman asking about an estimate: “We don’t give estimates. We make promises.” So good.

Business Logo

Your new business needs the right public image. How do you choose the right logo design company to create business logo ideas that will represent your new small business?

Think of your company logo as the visible part of your brand — and the company logo ideas from a business logo design company as fuel for your marketing engine.

Will you use a classic, traditional look or something very modern and trendy. See our business naming tips for more on this.

Logo Design Company

The experts at 99Designs provide affordable business logo design by marshaling a world of creative talent through an easy-to-use website. You get to work with dozens of highly talented people, each of whom will have fresh, unique ideas for your small business logo.

The logo for SohoSpark was generated through 99Designs and my experience working with this company’s website and creative crowd was first rate. The website is easy to use. The dashboard lets you eliminate irrelevant designs quickly and a message view groups design attempts by designer so that you can keep track of what you’ve said to each person. Don’t be fooled by the “99” part of their name. My logo contest generated 434 design entries by 70 designers. That’s a lot of bang for my branding buck!

Before you start: Be prepared to interact with the design community. A lot. I was on the website several times each day, eliminating irrelevant or lesser designs and giving feedback and direction to maximize the effort from the creatives. This is not the kind of project you can launch and then leave for vacation.

Pro Tip: Guarantee your project right away. This shows the creative crowd that you are serious and that their time will not be wasted. I did not do this for the first couple of days and after I did, I noticed a sharp jump in the participation by some very talented artists.

A pleasant surprise was the poll feature that lets you ask your friends and social community to help you narrow down your choices. I used this feature after the qualifying stage but before I had to finalize my finalists for the next round. Having that external input is so helpful to loosen (notice I didn’t say remove) the personal bias from my decision!

Resource: 99Designs

Business Naming

Business naming is not easy but there are some great services available to help. A worldwide audience of creative people act as a giant company name generator that will help you brainstorm company name ideas, marketing slogans, taglines, etc.

Business Naming Services

Here are my favorites:


For about $200, the squad will generate dozens or hundreds of ideas in just a few days. I used this service for the website you are on now and they created 363 ideas in just three days. That’s a lot of bang for the buck and I got to leverage my time by doing something else while all those names piled up!


Starting around $400, this one is a bit more expensive but they do more work on your new name. Their creatives not only generate name ideas, but will also spend some time voting on them. The result is that you know which names are the most popular — at least among the creative crowd who contribute to such contests. If those opinions are important to you, ante up for the extra time and effort this gang puts in.

How to Name a Business

Business naming should be done with care so that your primary customers both understand and respect your brand. Things to consider when naming a business:

  • age
  • gender
  • income
  • geography
  • culture
  • style
  • clarity
  • ease of pronouncing
  • meaning
  • logo options

For example, if you’re selling products or services to teenagers, then you’re name will have to be trendy and cool. Sounding old or stodgy will be a turn-off for this audience. If you’re selling to middle-aged men, naming a business something professional and solid will put your prospects at ease.

Register Your Business Name

A sole proprietor does not have to register at the state level unless they are using a name other than their own (a DBA). Other organization types like corporations, non-profits, and LLC’s require that you register with the appropriate agency.

Make sure you do a corporate name search to make sure that the name you have chosen is free of legal entanglements. Do this at the country level as a trademark search and also do it at the state level to ensure that you are free of local conflicts. State registered corporations do not have to register at the country level and thus could create a problem for you if you infringe on their brand. For the DIY crowd, here are some search tool examples:

Once you have decided on a business name and business structure, make sure you register it with one of the state agencies.

Business Structure

You do not have a create a formal business structure if your operation is small and your liability risk is limited. If you sell custom cat pillows from home, for example, you don’t need to worry about business organizational structure.

Many of you will grow your business or take on risk in the market, however, so this article will help you with choosing a legal business structure (sometimes called a business type). We will examine the various types of business ownership and help you pick one that is suited for you and also explain the benefits of incorporated business structures.

Those of you that start small and grow at a modest pace will probably end up using one of these types of small business:

  • Sole Proprietorship
  • Partnership
  • Limited Liability Company
  • S Corporation

Other company structure types are better suited for large businesses. If you plan to start off with a big bang or know that you want to get huge, you’ll want to consider the benefits of a larger business structure:

  • C Corporation

Now let’s look at each business structure in more detail.

Sole Proprietorship

A sole proprietorship is the simplest business structure. It’s basically just you, the owner. You get all the money and have all the responsibility.

Setup Chores

There aren’t any .You just start doing business and, voila!, you are a Sole Proprietor. Examples of this business structure: freelance designer, writer, consultant. You still need to get the correct license or permit, if your state or county requires one. You just don’t need fancy paperwork and a corporate seal to be legit.

Do you want to be Cat Customs instead of Sally Smith? No problem. Just file a DBA (doing business as) form with the state and your local bank. This will keep you from being arrested when you cash checks (so awkward).

Tax Implications

Legally speaking, you and your business are the same thing. You will report income and loss using the Schedule C on the standard Form 1040. You have to withhold and pay all income taxes including self-employment taxes. Gotcha: You can’t wait until the end of the year to do this. The IRS expects you to make quarterly estimated tax payments based on your projected income (or last year’s numbers).


  • Easy to start — Little paperwork and
  • Total control — You get to make all the decisions
  • Easy tax prep — Simpler forms and the lowest business tax rates


  • Personal liability — It’s all you, baby. No corporate shield to hide behind.
  • Limited fundraising — No stock to sell. Banks get nada if you fail, so loans are tough.
  • Pressure — Success or failure is all about you. This is the other side total control.


A partnership is a single business where ownership is shared by — surprise! — two or more people. All partners contribute to the money, property, labor or skill of the business and they all share the profit or loss.

Making decisions with multiple owners can be a challenge, so discuss the big rocks up front. You may think that you are highly compatible already, but these early discussions of principles, core values, and methods will bring differences to light. Decide together how you will:

  • Make decisions
  • Divide profits
  • Resolve conflict
  • Handle ownership changes
  • Dissolve the partnership

Put these principles down in your partnership agreement. You don’t have to make a legal agreement, but do it anyway. You take a huge risk operating without one. If your would-be partner doesn’t see the need, then think twice about going into business with them.

Partnership Types   

There are three general types of partnership arrangements:

  • General Partnerships — Management duties, risk, and profits are assumed to be equal among partners. Anything different can be detailed in the partnership agreement.
  • Limited Partnerships — allow limited liability for partners as well as limited management input. Attractive to investors of short-term projects.
  • Joint Ventures — Limited time and for a single project. Partners can continue after the project but must file as a general partner.

Setup Chores

Register your business in your state, usually through the Secretary of State.

You’ll also need to establish your business name. For partnerships, your legal name is the name given in your partnership agreement or the last names of the partners. If you choose to operate under a name different than the officially registered name, file a DBA.

Obtain the necessary business licenses and permits. Regulations vary by industry and geography.

Tax Implications

Most businesses will need to register with the IRS, register with state and local revenue agencies, and obtain a tax ID number or permit.

A partnership must file an “annual information return” to report the income, deductions, gains and losses from the business’s operations, but the business itself does not pay income tax. Instead, the business “passes through” any profits or losses to its partners. Partners include their respective share of the partnership’s income or loss on their personal tax returns.

Partnership taxes generally include:

  • Annual Return of Income
  • Employment Taxes
  • Excise Taxes

Partners are responsible for several additional taxes, including:

  • Income Tax
  • Self-Employment Tax
  • Estimated Tax

Partnerships must furnish copies of their Schedule K-1 (Form 1065) to all partners by the date Form 1065 is required to be filed, including extensions. Partners are not employees and do not get a Form W-2. See the IRS Guide to Partnerships.


  • Inexpensive — Easily formed business structure with few startup expenses
  • Shared Commitment — Each partner is equally invested. They can pool resources to obtain capital.
  • Blended Strength — Benefit from the strengths, resources and expertise of all partners
  • Performance Incentive — May offer employees the opportunity to become a partner, attracting highly motivated and qualified staff


  • Personal Liability — Partners have shared among the owners for their own actions and also for the debts and decisions made by other partners.
  • Conflict — Partners must learn to compromise and resolve disputes well.
  • Shared Profits — Joint owners share the successes and profits of their business. Inequity in contribution of effort or resources can cause discord.

Limited Liability Company

A limited liability company (LLC) is a hybrid business structure that combines two others: It provides the limited liability features of a corporation plus the operational flexibility and tax benefits of a partnership.

In an LLC the owners are called members. Depending on the state, the members can consist of a single individual (one owner), two or more individuals, corporations or other LLCs.

Unlike shareholders in a corporation, LLCs are not taxed as a separate business entity. Instead, all profits and losses are “passed through” the business to each member of the LLC. LLC members report profits and losses on their personal federal tax returns, just like the owners of a partnership would.

Setup Chores

Business Name. States are picky about you set up your LLC business name:

  • Must be different from every existing LLC in your state
  • Must include “LLC” or “Limited Company”
  • Must not include restricted words like “bank”

Articles of Organization. This simple makes your LLC legit and includes information like your business name, address, and the names of its members. Typically filed with the Secretary of State but this may vary from state to state. Expect a filing fee.

Operating Agreement. Recommended for multi-member LLCs but not always required. This document structures your finances and organization. It also lays out percentage of interests, allocation of profits and losses, and member’s rights.

Licenses and Permits. Obtain proper business licenses and permits. These vary by industry and geography.

Business Announcement. Some states require you to publish a business formation statement in your local newspaper.

Tax Implications

An LLC is not a separate tax entity, so taxes are passed on to the members and paid through their personal income tax. While the federal government does not tax income on an LLC, some states do, so check your state rules.

How the IRS treats your LLC for tax purposes depends on the elections made when you set it up. Depending on your classification, you may file your taxes as a sole proprietor (Schedule C), a partnership (Form 1065), or a corporation (Form 1120). See the IRS.gov LLC explanation for details. Talk to your state tax agency about what classifications they will recognize for your LLC.


Limited Liability. Members are protected from the actions of the LLC such as massive debt or lawsuits. Members are not necessarily shielded from wrongful acts, including those of their employees.

Simpler Records. The ease of operation is a big plus. Less registration paperwork and smaller start-up costs.

Profit Sharing. LLC members distribute profits as they see fit. Each member can contribute different levels of money and effort, so the members decide as a group who has earned what percentage of the profits or losses.


Dissolution Events. If a member leaves, some states dissolve the LLC and the remaining members must shut down the business. Members can decide if they want to start a new LLC or part ways. You can protect against this automatic headache by adding provisions to your operating agreement to prolong the life of the LLC after a member leaves.

Self-Employed Taxes. Members of an LLC are considered self-employed and must pay the self-employment tax contributions towards Medicare and Social Security.

S Corporation

An S Corporation (or ‘S Corp’) is a corporation with the Subchapter S designation from the IRS. This legal entity is separate from the owners, which limits their financial liability. This protection does not necessarily shield you from all litigation such as an employee’s tort actions in a workplace incident.

Profits and losses pass through to your personal tax return, which eliminates tax on the business itself. To keep you from gaming the system, however, a shareholder who works for the company must pay him or herself a reasonable compensation. Otherwise, the IRS might reclassify any additional corporate earnings as wages. That will hurt!

Setup Chores

Before you form an S Corporation, determine if your business will qualify under the IRS rules. Then you file as a corporation. After you are considered a corporation, all shareholders must sign and file Form 2553 to elect your corporation to become an S Corporation.

Next, obtain the proper business licenses and permits. Regulations vary by industry and geography.

You can request S Corp status for your LLC by asking for a special election from the IRS on Form 2553. This must be done early in the tax year in which the election is to take effect. If you get the S Corp election, your LLC remains a limited liability company but is taxed as an S corp.

Tax Implications

All states do not tax S corps equally. Most follow the federal rules and tax the shareholders accordingly. However, some states tax S corps on profits above a certain limit. Other states ignore the S corp election and treat the business as a C corp, which has sizable tax ramifications. Some states tax both the S corps profits and the shareholder’s profits.


  • Tax Savings — Your wages as a shareholder employee are subject to employment tax. The remaining income is paid to the owner as a “distribution,” which is taxed at a lower rate, if at all.
  • Business Expense Credits — Some expenses you incur can be written off as business expenses.
  • Legal Separation — The business has its own life separate from its shareholders. If a shareholder leaves or sells their shares, the S corp continues relatively undisturbed.


  • Process Discipline — Requires director and shareholder meetings, minutes, updates to by-laws, stock transfers and maintenance of records.
  • Compensation Requirements — A shareholder must receive reasonable compensation. Otherwise, the IRS might reclassify your distributions as wages, resulting in a big audit bite.

Other Business Structures

The details above will give you a business structure for most small businesses. If you need information about alternative business types, click on these links to read more:

Need Business Structure Help?

If you don’t have a personal attorney, the experts at Legal Zoom can help you navigate the business structure maze and get your company set up.

Test Your Business Idea

I recently shared an idea with friends over lunch and they immediately spotted a big hole in my super smart theory. It doesn’t mean I won’t pursue the idea. It does mean that as I move forward, my strategy will be better and I will avoid some open manholes because the early draft of my idea was scrutinized by others.

Most business startups do not succeed. You’ve heard this before but probably dismissed because, well, in your own mind it doesn’t apply to you. Maybe yes, maybe no. It is valuable to study why small businesses fail. You can study the carcasses of others to avoid a similar fate.

But what if there was a way to tip the scales in your favor? What if you could avoid spending a ton of time, energy, and money only to see your business become a statistic? Well, you can.

Getting out of your own head is crucial to minimizing your failed attempts. Putting your precious business idea to the test will help you do that. There are many different ways to do this. Some of them will take only a few minutes to try. Do you have the patience to do some testing first? I hope so. Hubris has been the downfall of many would-be business owners who were ‘too smart’ to test their ideas!

Business Basics

  • Create something people want
  • Prove that enough people want it
  • Prove that you can reach those people
  • Prove that your message is effective

For some of you, a negative rule carries more weight than the positive version. For you I will restate the same basic principles above but in reverse language and reverse order. Here they are in the voice of your prospect:

  • I won’t care if you don’t speak to my issues
  • I won’t hear if you miss my channel
  • I won’t matter unless you find many of me
  • I won’t buy unless I really want it

The following list, digested from over a dozen of the best sources, summarizes how you can test your idea before betting the farm on it.

Testing Your Idea

Method Description
Wait Give your idea time to percolate in your mind. If you stew on it for a few weeks and still believe that the world needs it, start testing.
Find similar products You want to find competitors for two reasons: You want to know that there is a legit target market and that those people will spend money.
Attack yourself This is a variation on the differentiation exercise. Imagine a competitor enters the market to compete with you. How would they take ground from you? Would they be similar or different?
Test with Facebook Facebook’s Ad manager can tell you how big of a target market you have for a certain topic in a specific geography.
Invite scrutiny Do you want to succeed or do you want to be right (in your own head, anyway)? Hubris can take down the best minds. You must love winning more than you love your new idea. If it can survive the analysis of other bright minds, you may have a winner.
Engage a mentor or critic Get honest, been-there and done-that feedback from someone in the industry you’re targeting. Their blunt critique might hurt but it could save you much time, money, and heartache.
Enlist a focus group Your friends and family will probably not give you objective feedback. Gather people who are potential customers and ask them to be blunt.
Buy Google Adwords Build a sign-up page and then run some Adwords tests. A small investment yields big results by proving that people want your stuff.
Check Amazon Best Sellers Is there a category for your product? Is there healthy competition?
Check Google Trends See the trend of others who are looking for your product concept.
Test on Craigslist If you make your offer on CL and get sufficient interest, you may be on the right track.
Read Negative Reviews Look at reviews for similar services and read the lowest ratings. You may spot problems in your own thinking ahead of time.
Write about it If you write up your idea in a blog post, people will give you feedback. Some of it will be helpful.
Use Crowdfunding Sites like KickStarter and IndieGoGo allow entrepreneurs to raise funds and build a relationship with buyers. If your campaign goes bust, you have problems that need to be solved.
Build the MVP Minimum Viable Product – the simplest version of the product that you can actually sell. Technically this is not a pre-launch test, but shipping a minimal product can saves you money and allows you to get real-world feedback so that (if you’re listening) your product can become successful.
Want more step-by-step wisdom on this topic? Pat Flynn’s new book Will it Fly? is a must-read. Let the master of SmartPassiveIncome show you how it’s done.

Working from Home


Maybe you’re just sick of the commute. Sharing the freeway with crazy people is getting old. I don’t blame you. Idiot sightings are up and it’s hard to get through an intersection in one try with everyone feeding their phone addiction.
Maybe you’re dreaming of starting something special. A service that comes from the heart, dished up for people that you care about. The world has waited too long for this, you say. It’s time. You’re gonna launch it and the fuzzy slippers routine is the way to go.
Whatever your motivation to start working from home, you know it’s not going to be easy. There are obstacles, risks involved, and things to prepare for. The big come-on for starting a small business from home is, “Free! I’ll be free!” Waving goodbye to your tyrant boss will make you feel more independent, but there are many time-sucking denizens lurking in your home-office future.

When I made the leap, my manager Fred told me, “Michael, you’re underestimating the amount of administrivia that our company takes care of for you.” That was the understatement of the decade. Of course, no one article is going to stop you if you’ve decided to make the leap to start your own small business. This article, however, will help you jump with your eyes open. This is my collection of things to think about as you settle into the starting blocks and look down the lane towards the finish line.



  • Increased flexibility. Getting to that soccer game is no big deal.
  • Energy management. Take a nap if you need to and then hit it hard again. No one is watching.



  • Casual dress
  • Productivity — your personal work style — is totally up to you
  • Part of your home is now tax-deductible for the business


  • Distractions (kids, partner, roommate, visitors) can steal your productivity
  • Transitions are abrupt. You can go from deep into a deal into holding a sick child.
  • Organization is all you. If you can’t find it now, it will get worse.
  • Feeling isolated. Somewhat offset by networking and social media.
  • New staff likely will not appreciate the lack of office amenities
  • Line between work and family/leisure gets blurred. Work is always available and you must be able to walk away from it.
  • The informal setting can lower credibility with clients and prospects
  • Productivity depends on you being really good at self-management
  • The family loses some living space to make room for your office
  • Family may resent your staff as privacy invaders



  • Lower overhead by dodging an office lease
  • Fewer lunches out (maybe – depends on your networking needs)
  • Lower car-related expenses
  • Lower dry-cleaning bill (casual dress)


  • Must acquire your own health insurance
  • Computer, business phone, printer, Internet, teleconferencing software, accounting software, online file sharing, etc.



  • No boss
  • Less stress because you are in control and don’t feel as rushed


  • Lots of quasi-bosses: prospects, buyers, clients, vendors, business partners
  • Harder to form new relationships without daily contact
  • Less people to learn from when you work alone
  • You wear all the hats: boss,  bookkeeper, customer service, printer repair.


Make sure you check in with your County and State to make sure that your specific type of  business is allowed to operate from a private residence. Check out the official SCORE guide on the subject.

These links contain overlapping ideas about working from home but they are just too funny to summarize!

One make or break quality of successful starters is having good habits. To see how daily habits shape your destiny, check out The Compound Effect from Darren Hardy. Don’t let the size fool you. This little book is a life-changer.

Make sure you test your business idea out before wasting a lot of money and time on a dud.

Image by Shannon McGee

Myths about Starting a Small Business


When I set out to study and catalog the myths (lies) we have been told about starting a small business, I honestly thought that I would find ten or so. After reading 11 articles on the subject, I was shocked to find 71 topics listed. Apparently, there is a boat load of crappy information running around in this category. No wonder we are confused and discouraged about what to do!

I have trimmed the duplicates, combined a few items, and removed the myths that cater to large enterprises in order to keep the list smaller and focused on the those who are starting a small business. Keep that in mind as you read through the list. This isn’t about creating and launching Apple or Facebook or Uber. It’s about starting something small on your own that will probably change as you get into it.

Since the words that we ingest matter, I am going to state the myth and then restate the corresponding truth. Read the whole table for understanding. Then read the right-hand column by itself to affirm your ability to start your own small business.

Myth vs. Reality

Myth (Lie) Reality (Truth)
Find money Lots of people bootstrap their business.
You must be technical You can learn the technology needed.
Find a unique idea and keep secrets Talk with people you trust and you may find partners and customers. Ideas are not usually unique.
Prepare an exit strategy Focus on building a great product and serving customers.
Quit if you fail Learn from failure and start again smarter. Lots of founders fail before they succeed.
Build it and they will come A real business has marketing, sales, product development, relationships, etc.
Work 24/7 and do everything yourself Delegate. Stop working when you become unproductive. Rest to avoid burnout.
Know what you’re doing Believe there is something that needs building. You’ll figure out what it is as you go.
Create a full business plan Outline what you’re going to do and how you plan to measure it. A few pages of clarity is enough to start.
Start at the right time Start now.
Hire staff Keep overhead low. Stay lean and outsource.
Focus only on the product Plan for marketing too.
Finish the product, then market it Test your idea. Confirm that you have a product that people want.
You’ll be your own boss You answer to your customers
A business is the best road to riches Starting a business is risky. If money is your driver then learn new skills, network and stay promotable.
Take lots of risks Make careful, calculated bets
Rent office space Avoid overhead. Work from home or the coffee shop. Find Coworking spaces are popular for startups.
More features will improve your product Stay simple. Deliver benefits to customers, not features.
Do what you love and money will follow Some passions cannot be monetized.
Go for the largest market Large markets have fierce competition. Pick a niche where you can make a loud noise.
Your business must grow Growth is not the same as improvement. Seek a size that is stable and has a good margin.

Believe in yourself and your ideas. Believe in your passion to provide a great service that people want. Believe the truth… and begin!

Why do people really start a small business? Find out in the classic book The E-Myth Revisted by Michael Gerber.
Image credit: Gabriela Fab

Side Hustle


You don’t have to leave your current job to start a business if your goal is just to make an extra car payment each month. Instead, think about starting a small, part-time business on the side. If it goes well, you can invest more effort and grow it until you feel secure enough to make the jump to full-time in your new career.

Now this will be obvious, but some businesses can’t be started as a side gig. Heart surgery is really hard from your basement and space walks, well, they take a lot of infrastructure. Both of those jobs require an all-in commitment and lots of specialized training to pull off. Simpler jobs like a professional passenger pusher, mourner, or snuggler require that you be physically present to render those services. Yes, I’m serious and no, you can’t phone these jobs in.

There are plenty of jobs, however, that lend themselves quite well to the side hustle approach. Here are some of the more obvious choices…


These jobs can often be done remotely because the product is delivered electronically or the job involves labor that is unsupervised:

  • programmer
  • graphic artist
  • bookkeeper
  • Excel expert
  • writer
  • online tutor
  • portrait painter
  • goods reseller
  • drop shipper
  • survey taker
  • ad watcher
  • contest winner
  • website builder
  • phone support


These jobs usually have to be done in person:

  • waitress
  • barista
  • hotel clerk
  • photographer
  • gym receptionist
  • babysitter
  • nanny
  • personal tutor
  • car washer
  • dog walker
  • store clerk
  • personal chef
  • elder care specialist
  • personal shopper
  • baker
  • organizer
  • massage therapist
  • landscaper
  • lawn mower
  • interior decorator
  • house painter
  • driver (Uber, Lyft)
  • food deliverer


Here are some websites to get you started hunting for freelance work.

Suggested Reading

The $100 Startup by Chris Guillebeau.

Got a brilliant idea for a new business? Test your idea before wasting time and money on it.