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Business Questions to Ask Yourself

These are helpful business questions to ask yourself or your partners. 

Each of these are designed as thought-provoking questions that will help your business get more clear on what you offer and how to grow.


#1.) Why did you decide to start this business?

This pokes at your true motivation for starting your business. 


  • I wanted to make money.
  • I wasn't sure what else to do
  • I wanted to solve X problem.

#2.) Can you describe your product in one sentence?

Often times if you can't describe your product easily, you might not have nailed down exactly what you sell. 


  • I sell propane and propane accessories. 
  • Copywriting Course is a set of tools, exercises, and community to help optimize every piece of marketing and copy you send out. 
  • I sell car tires in the Greater Chicago Area.

#3.) What main benefit does someone get if they buy your product?

You're not selling specific features of a product, but rather what that product does for the end user. 


  • They save time doing ____.
  • They make more sales by using ____.
  • Turnaround time goes from 5 days to 5 minutes.

#4.) What is the best method you’ve found to sell your product?

You probably know what your best ways of getting sales is, can you do more of that? Can you make that a process?


  • Getting on other people's podcasts or newsletters.
  • SEO and Content Marketing. 
  • Interacting with groups on social media.

#5.) Why did you start a business in this specific industry?

Why did you pick your specific industry? Can you offer the same service to a different industry that will value your product more? 

Some website agencies charge $1,000 for a full website to solopreneurs, but another website agency might charge $150,000 to a financial company. 

Same product, different price. 


  • I wanted to solve my own problem. 
  • I wanted a tool like this, and nothing existed. 
  • I wanted to make money and live a great lifestyle.

#6.) What would you do if you had to start this business again from scratch?

Sometimes we keep chugging along on a business out of momentum....but what if you had to start over? Would you do thing the same, or change something up?


  • I would only serve higher priced customers.
  • I wouldn't sell my service so cheap. 
  • I would niche down into a different industry.
  • Instead of a website I'd just do social media first.

#7.) Do you have a 1 year plan? 5 year plan? 10 year plan?

A ship with a destination will likely reach it. But what if you have no destination? You might squander your time. 

Having some roughly yearly plans can help guide you to where you want to go.


  • 1 year plan: Hit 5 sales per day.
  • 5 year plan: Remove myself from the business.
  • 10 year plan: Sell the business to a larger company.

#8.) Do you want to run this business forever, or eventually sell it?

This is helpful to think about, so you have a longterm and short term plan.

  • I would like to run it for as long as it's fun, then sell. 
  • I have an exit plan in mind already. 
  • I'm just winging it for now and will re-visit the idea.

#9.) If someone gave you $10million to grow your business, how would you use it?

This is helpful, as it will show you where your growth channels would be.

  • Get new email subscribers at $X/each, because I know each subscriber is worth $Y/each.
  • Buying FB, Instagram, TikTok, and Google Ads.
  • I don't know 🤔

#10.) Who are my competitors?

This is a fun thing to outline, so you can monitor, get inspired by, or get fired up by their competition.

  • Look for people who rank for similar SEO terms.
  • Look for people more visible on social media. 
  • Maybe someone in a different industry is doing something similar. 
  • Can you see what other companies are doing well? 
  • What offerings do competitors have that you don't?
  • Don't just copy, but just take stock of these things and analyze.

#11.) Who in my industry would I most like to be? What specific aspects of their company do you like?

You may not want to be exactly like someone, or exactly like another company, but instead 

  • I would like to be kind of like ____.
  • ____'s marketing is great, and I would like to do more of that.
  • I like how ____ structures their pricing.

#12.) Which channel brings in the most customers? Can you double down on that?

It's sooo easy to get sucked into a million different social platforms, so figuring out which one is the most effective 

  • My Twitter account helps me meet the most people. 
  • Email sells the most. 
  • YouTube channel keeps brining in new customers.

#13.) What’s my company's value proposition?

Being able to say this in one sentence is important.

  • We sell car tires for the best prices, and fastest installation. 
  • We train people to become top copywriters.
  • We sell shoes that help you run faster.

A helpful formula could be:

For $X we will send you PRODUCT in two weeks.

#14.) Have similar companies to mine been sold for a lot of money?

Knowing this can tell you roughly what you could sell a similar company for.

  • A company similar to mine in the ____ industry sold for $50m.
  • A company doing similar stuff sold for a 10x revenue multiple.
  • No company like mine has ever sold.

#15.) What can this company realistically grow to?

What can you grow to? Are you too niche?

  • Similar companies have grown to $20m/yr.
  • The total market size for knitted hats of GI Joe toys is under $40,000/yr.
  • Similar accounting SaaS companies have become public companies.

#16.) How are my prices compared to my competitors?

Are your prices lower, higher, or similar to your competitors? 

Generally higher priced products are preferable because you can do more for each customer. Lower pricing helps in retailing, but in software or informational products is not as good as high priced.

  • Is my product good enough that I can charge more than my competitors?
  • Do I have Three Tiered Pricing setup for capturing low end customers AND high end customers?
  • Should I do flat pricing, or Value Based Pricing?

#17.) What if I 5x my pricing? Could I serve my best customers better?

Believe it or not people respect higher prices more. Let's say there's a course for sale that's $5.00, and one for $5,000. 

The one for $5,000 seems higher value. There's countless times through history where a company raises prices, and ironically sales go up. 

  • What would happen if I just 5X'd pricing....maybe less clients sign up, but income goes up. 
  • Many agencies have done this: 5X'd or 10X'd pricing, but then accepted fewer clients. These higher priced clients are better.
  • Can I offered Tiered Pricing to still offer my product at the same price, but offer a higher valued package for 5X to 10X the price?

#18.) What bigger company would want to buy me? Why?

This is a great question to ask, because it can show you WHY a company would want to buy you. 

For example, TheHustle was acquired by HubSpot because TheHustle had 1m+ email users who read their daily tech updated. HubSpot wanted those extra 1m+ subscribers to promote their software. 

  • Figure out which companies would potentially buy you. 
  • Figure out which specific asset of yours they'd want to buy (email list, proprietary technology, customer info etc..)
  • Figure out if there's other industries that would want to acquire your company

#19.) What’s a bottleneck in your company? Is there a way to clear that?

I bet there's a bottleneck in your company, and it might be YOU 😬

  • Is there a way to give employees permission to bypass you and put things out?
  • Can you insert software that will get rid of this bottleneck? 
  • Can you release some control so others can be free to output work without your approval?

#20.) If you were to disappear for a week, which process in your company would break first?

I love this question, because you probably know the answer already.

  • Is there a way to outsource these tasks to someone else?
  • Is there software which will remove this problem?
  • Can you do a monthly session where you pre-work on the stuff that breaks, so you can be out of commission for a long time without things breaking?

#21.) Is your income one-time or recurring? Is there a way to make it more steady?

Recurring income is usually the holy grail, because you get regularly scheduled income every month or every year. Insurance companies, mortgage companies, software companies all work like this. 

#22.) If you were starting over, would you start this business again?

This is a great question. Are you doing your current business simply out of momentum, or would it be a great business to start again? 

  • Some people just keep doing whatever job or business they are in because that's what they have been doing for years. It's helpful to re-think if it's still a good fit after a few years. 
  • Maybe if you were to re-start this business again today you'd be doing something different? What would you do different? Can you implement that change? 
  • How could you change or create something in the business that would give you the same passion as when you started?

#23.) Which book influenced you? Can you re-read it and implement strategies?

Re-reading a great book can be better than reading a new book that kind of sucks. 

  • Write down some of the ideas you picked up originally but haven't implemented. 
  • Implement those ideas into your business. 
  • See if there's any cool tips or strategies you can use.

#24.) Which person in your company could you NOT get rid of? What are their good qualities?

I bet you have some people in your company you think are crucial. What qualities do you like of them that are important? 

  • Can you find more people like this? 
  • Can you have those good people work on other stuff you need help with? 
  • Are you doing everything you can to make their work easier and better?

#25.) Which person in your company can you get rid of? Can you divert their pay into something/someone more useful?

There might be people at your company who you continually think are underperforming. This can drain your bank account AND morale.

  • Can you have a talk with them about under performing, and give them a chance to improve?
  • If they can't perform well, just get rid of them. Not worth having the dead weight hanging out sucking resources and money. 
  • Keeping bad people around infects the rest of your company culture. 

#26.) What would _____ do with your company?

This is a helpful question: "What would _____ do with your company?" 

Think about the different approaches each person would take with your company, maybe it'll prod you into thinking of some interesting products to offer or directions to take your company.

  • What would Elon Musk do with your company?
  • What would Warren Buffet do with your company?
  • What would Oprah do with your company?
  • What would Sergey Brin do with your company?
  • What would Mark Zuckerberg do with your company?

#27.) What natural advantage do you have over others? Can you double down on that?

I bet there's something YOU IN PARTICULAR are very good at, that you should maybe double down on. 

  • Are you very good at podcast interviews? Can you do more of them?
  • Are you very good at creating blog content? Can you do more of them?
  • Are you very good at managing people? Can you do more of that?

#28.) What are YOU truly good at that few others can do? Can you double down on that talent?

Sometimes the world will tell you what you're good at by paying you for it, or people asking you to help them with it. 

  • It's good to find what you're great at, and be able to offer it at scale. 
  • It's helpful to find these talents and double down on them. 
  • It's helpful to find these talents and train others how to do them. 

#29.) Which industry could you make more money doing what you do now?

Some industries will pay 100X more for a similar service. 

  • If you do web design for startups, maybe a larger company will pay 10X more for a similar product. 
  • Moving up the value chain is important for getting higher priced clients. 
  • If your service solves a bigger and bigger problem you can command more money. 
  • A massage therapist that does massages can make $80/hour. A massage therapist that focuses on high end clients or medical-grade massage can make $300/hour.

#30.) You only get to keep ONE customer…who would it be? What about them makes them ideal? Can you find more like them?

Fire all your bad clients, and keep all your good ones.

  • It's likely you already make A LOT of money from a certain set of customers, and VERY LITTLE from others. 
  • Figure out the similarities of the good customers, and find more of those types. 
  • Or you can just focus on a small set of customers for a higher price, rather than dealing with a lot of customers for a low price. 
  • See what kind of prices you can get with this Pricing Calculator.
  • You can make $1m/yr by selling 10,000 products $100. 
    You can make $1m/yr by selling 10 products for $100,000.

#31.) Where do you think your industry will be in 5 years? 10 years?

Where's your industry headed, and you can get ahead of that curve?

  • Will certain software change the way your industry operates?
  • Are more people digitizing an old process, and can help implement these changes through the industry? 
  • Is there a topic you could become a thought-leader on?
  • Is your industry shrinking or growing?

#32.) If you wanted to sell your company today, would you be able to do it? What’s holding you back?

This is a great question, as most business owners have no idea how to sell their company, or how to get it into a place where it can be sold.

  • Are YOU crucial to the business? Can it operate without? If not, it'll be hard to sell. 
  • What would someone acquiring your business really buy it for? The SEO value? The email list? The people? The tech? 
  • What can you start doing to make your business a sellable asset at some point? 
  • You should think of how to make your business sellable MUCH BEFORE you want to sell it.

#33.) Do you track all your numbers properly? Do you review them?

"What gets measured, gets managed."

  • If you're not tracking your numbers, you may want to set aside a time every month to review them. 
  • Just seeing if things are trending up or down is extremely helpful. 
  • By tracking your numbers and occasionally monitoring them you can often spot activities that bring you lots of money or lose you lots of money, and can optimize from there.

#34.) You only have 1 hour a week to grow your business….what would you do during that hour for most impact?

I bet you know the answer to this already. 

  • I've found that reaching out to new audiences for video or podcast collaborations to be a great source of quickly driving new business. 
  • Some of the activities you do probably have more bang-for-the-buck than others, can you double down on those? 
  • Is there a system you can put in place to make sure these high-value activities happen every week?

#35.) What makes customers smile when they buy your product?

Ultimately you sell to customers, and want to make them happy. Are there certain activities that impress your customers the most? 

  • Can you do more of that?
  • Can you make this a separate service?
  • Can you call your last 10 customers to see what they love or hate about your product?

#36.) Do your customers tell their friends about you? What do they say?

Word of mouth referrals are the most powerful promotion you can get. 

  • Are your customers ever talking about you? That's GREAT!
  • What do they say about you? Can you write these down somewhere and keep track of these?
  • Maybe you can put all these kind words into a testimonials page?

#37.) Define your ideal customer in one word….

Who is your ideal customer?

  • "Business owner"
  • "Fortune 500 company"
  • "A mother"
  • "A solopreneur"

#38.) What outcome do you want in 2 years from this business?

This is an important question and time frame. One year might be too little to get big results, and 10 years might be too far out to predict. 

  • In 2 years where do you want your income level to be from this business?
  • In 2 years what other side benefits do you want? Larger social accounts? More friends in the industry?
  • In 2 years what size could this realistically grow to?

#39.) What about your company are you proud of?

There must be something you do well that you're proud of.

  • Can you do more of that?
  • Is it something you can monetize on more?
  • Is it something that'll differentiate you from competitors?

#40.) What about your company are you embarrassed of?

I bet there's something you're NOT proud of about your company. Can you improve on it?

  • We don't take of customers all that great. 
  • We don't post good stuff on social media. 
  • Our website is not optimized at all.

#41.) What’s an example of a customer success story?

Who experiences success with your product?

  • Do you keep a file with all of these stories?
  • Do you share these stories with others to show them the value of your product?
  • Can you figure out how to replicate those results for 1,000's more people?

#42.) What’s been your most popular piece of content so far? Can you do more like that?

If a piece of content you've made really hit, can you make more like that?

  • Repeating similar stuff may not hit every time, but content is a numbers game. 
  • What about that content really hit home with people?
  • Just remember you might post 50 things, only one might hit it big, a few will be OK, and many will stink. Keep publishing!

#43.) What specific pain point are you solving? Is there a demand for that solution?

Sometimes businesses can flounder for a long time if they are not solving a specific problem.

  • Is your company actually solving a real pain point, or just something that would be "nice to have?" 
  • Is there actual demand for this solution? 
  • Are there other companies selling similar stuff? That's usually a good sign. If no one is selling something similar, it could be there's no demand.
  • You can sell high quality sweaters for squirrels, but there might not be enough demand to make it a full time business.
  • There might be thousands of insurance agents out there already selling insurance, but that indicates there's lots of demand.

#44.) What background do you have that increases your credibility for this business?

Why should people listen to YOU specifically in an industry? 

  • Is there a way to post more of your social proof?
  • Is there something you can do (write a book, be on specific podcasts, write for specific publications) that will give you more street cred in your industry? 
  • Can you DO THE THING you talk about the most? For example if you talk about creating business is a lot, what if you create a big business and talk about that?

#45.) Who does something similar to your company, but in a different industry?

Think about others who do the same service as you, but in a different industry.

  • How is their service different than yours?
  • Could you shift into that industry also?
  • What if you borrowed ideas from how they sell?

#46.) How are you different from competitors?

What makes you stand out from your competitors?

  • Larger social media following?
  • Are good at video and they are not?
  • More credibility in your industry?

#47.) In 3 months what could be the biggest change you make to your business that would get more (or better) customers.

This question is good because it gives you enough time to implement almost any change. 

  • In 3 months what if you had a proper podcast outreach program going that gets you in front of other audiences? 
  • What if you build out a way to publish consistent content on your most effective social platform? 
  • Can you start regularly participating (or planning meetups) in the places where your ideal customer hangs out?

#48.) Would you want to work at your own company as an employee?

Is your company a good place to work? Would YOU work there?

  • How could you make it more fun to work at?
  • How could you align your employees personal goals with your goal?
  • Can you create a win/win/win for yourself, your employees, and your customers?

#49.) If you didn’t own the company, would you buy your product? How much would you pay?

How could you make your product or service a complete no-brainer?

  • Really think if you would buy your own product/service. 
  • Would you specifically buy it from YOU, or are other alternatives better?
  • What would tip your offering into "no-brainer" territory?

#50.) What do you think customers secretly think about your product, but don’t tell you to your face?

We all wonder what other people say about us behind our backs. And our business is no different.

  • Ask for honest feedback from past customers.
  • Put yourself in their shoes and come up with potential issues they have.
  • Be your own harshest critic.

#51.) What accomplishment or number would make you “feel awesome?”

So much of what you strive for is that awesome feeling. 

  • Is it a certain revenue number?
  • How many paying customers would you like to have?
  • Can you create that feeling inside before you actually achieve it?

#52.) When you daydream, what do you envision your company as?

Daydreaming can actually be a really useful activity when used effectively.

  • Imagine every detail (big and small) of your ideal work day. How do you make this your reality?
  • Who would be your dream customers you get to serve?
  • Is it a lifestyle business? Or do you want to be a publicly traded company?

#53.) How do customers find your company?

How could you make it as easy as possible to be discovered?

  • Do customers interact with each other and mention you?
  • Do you rank high on Google?
  • Are you running social media ads?

#54.) Who has been the biggest advocate and seller of your product?

Who loves what you do so much that they just have to talk about it?

  • A champion at a Fortune 500 company.
  • An influencer who tweets about you.
  • How can you incentivize them to spread the word?

#55.) What features of your product do customers use the most?

Do an 80-20 analysis on your product to find out

  • Customers will naturally gravitate to a handful of use cases
  • Ask customers which features they find most helpful
  • Discover those and dedicate more attention to improving them

#56.) If you could change one thing about your business, what would that be?

In your dream world what would change about your company?

  • Bigger social media following?
  • Larger email list?
  • More SEO traffic?
  • More attention from a specific industry? 

Figure out what exactly you want changed, and then start working towards that.


#57.) What marketing tactic brings in the most amount of sales?

Believe it or not, the simplest advice I can give you: Do more of what WORKS, and less of what DOESN'T WORK. Many time people will do amazing promotions or tactics that work well in their company, then never do it again.

  • It's OK to repeat a tactic again.
  • It's OK to re-try a tactic that worked well in the past. 
  • Try things that work again and again, until they don't work anymore.

#58.) Which time of the year do you make the most sales?

I bet there's a clear time of the year when you make a ton of money. When I ran a rave company, Burning Man (usually at the end of September) was always my biggest time of the year, even bigger than the holiday season.

  • Identity when you usually make the most income.
  • Start planning your promotions 3 months ahead of that time so you can be prepared. 
  • Do a lot of the work before-hand so during your busy time you're not drowning in work.

#59.) What is the slowest time of the year for your business? Are there ways to improve that?

You probably know the best time for your business, but what about the slowest times? 

  • Is there some big holiday you can use to do extra promotion?
  • Is there a challenge or contest you can run during this time?
  • Is this a good time to try fun experiments?

#60.) What started your interest in this industry?

There must've been some impetus for you to get into your specific industry.

  • Can you re-evaluate if you should still be in this business?
  • Is there a way to re-ignite your initial interest in this business?
  • Are you serving the same customers or are they different now?

#61.) What other services do your customers pay for in your industry?

It's important to know what else people are paying for, because maybe you can offer something like that also.

  • There might be many adjacent products you can also offer your customers. 
  • What other products would make your customers money, or save them money. 
  • Most big companies you know of offer MANY products and services, not just one.

#62.) Can you go through your checkout process as a new customer….what parts can be improved?

As business owners we see out websites all the time, but never interact with them as a TOTAL NEWBIE would.

  • Every week go through your own checkout process. See what issues you can find. 
  • Try to ask others to go through it for the first time, and watch where they stumble. 
  • Iron out all the hiccups you see in the checkout process that could cost you a sale.

#63.) How long does the average customer stay with your company?

The LTV (life time value) of a customer is important to know.

  • Can you extend the average customers LTV?
  • Are you in a business where once a customer purchases, they leave forever? Any way to make this recurring?
  • Can you add some sort of recurring revenue aspect?

#64.) What end result does your customer want from your company?

We often sell the product/service itself, but maybe we can focus on the end result your customer wants?

  • We sell Carpet Cleaning -VS- We sell a clean home you're proud of.
  • We sell a Copywriting Course -VS- We train you in a skill that can up-level your life.
  • We sell a Journal -VS- We help build your daily habits so you can build the life you dream of.

#65.) What challenge is your customer REALLY trying to solve?

Let's focus on the reason your customer is buying something. The REAL reason. This can shed light on why people buy. 

  • They buy a Copywriting Course -VS- They buy a training course so they can create their own career and be in charge, rather than be like their dad who had lots of problems paying the rent.
  • They are buying a water bottle because it's something in their life they can control to improve their health immediately. 
  • They buy into a monthly challenge group to prove to themselves they can stop drinking for a month.

#66.) Do you have a list of audiences you would like to reach?

At AppSumo we keep a file of all the people and groups we know that might want to co-promote a deal. When we have a deal about Wordpress, we'll reach out to everyone who does Wordpress related stuff.

  • Keep a spreadsheet of all the different audiences related to your product. 
  • It doesn't have to be stuff in the same industry, in fact having groups/people who could use your product OUTSIDE of your industry is important. 
  • When you need to get the word out about a post, video, or new product, you know where to look by having this list ready.

#67.) How often do you make goals for your business? Every month? Every year?

Keeping your goals updated is important. You should probably be keeping track of different sets of goals:

#68.) What is something your competitor does better than you?

I bet you can improve your business a bunch by just looking at what some competitors do better than you.

  • Are they putting out more content?
  • Are they more consistent?
  • Are they more inspirational? 

What lessons can you learn from them? Don't hate on your competitors, be glad they exist so they keep you on your toes, and outwork or outsmart them!

#69.) What is something you do way better than competitors? Does that activity bring in sales?

I bet there's things that you do better than your competitors also, but step back for a second and see if those things ultimately bring in sales.

  • Maybe you post more on Instagram, but it barely reaches any audience. Is it worth it?
  • Maybe you put more small blog posts out, but it doesn't reach many people. Is it worth it?
  • Maybe you have a prettier website, but it doesn't change the outcome if people buy or not. Is it worth it?

#70.) What’s something that brings in sales….but you hate doing? Can you have someone else do it….or make it more fun for yourself?

I bet there's certain sales activities you know bring in sales, but it's hard or boring or you just hate doing it. 

  • Can you find a way to have someone else do it?
  • Is there software that can speed up the process?
  • Is there a service out there that'll do it for you?
  • Can you make the process more fun for yourself?

#71.) Do you regularly call your customers on the phone and speak with them?

Calling people up and just asking a few questions can go a lonnnnggg way.

  • Ask them why they originally bought. 
  • Ask what they wish was better about the products. 
  • Ask them what competitors they like. 
  • Ask them if they would buy again.

#72.) How often do you interact with your paying customers?

Your currently paying customers might know some ways to improve your product.

  • Ask them how to improve your product. 
  • Ask them what features a competitor has that they like. 
  • Ask them what specific problem they are trying to solve, and figure out how to solve that faster.

#73.) Let’s say you had only one customer, how would you serve them versus what they get now?

Imagine you just had one REALLY HIGH PAYING CUSTOMER. What would be the difference?

  • Are there more services you could offer this customer?
  • Is there more personalized service you would do for them?
  • What process could you help them with to improve their business futher?

Figuring out what you would change could maybe put you in a position only to serve a few high end customers, instead of many lower end customers.

#74.) Is there a different industry that would appreciate your services more? That would pay you more?

If you are making websites for beginner freelancers, they may not be able to pay you all that much. But if you were making websites for large financial institutions they might pay you up to $100,000 each. Can you focus on larger industries?

  • Try to see if you can focus on industries where your product directly makes them money, or saves them money.
  • It's an easier sale if your product is an "income generator" rather than a liability.
  • What people doing similar work make more money in other industries?

#75.) Is there something in your business you could outsource to someone on UpWork or Fiverr?

Many business owners want to do things themselves, but there's 1,000's of people who can do similar tasks as you. 

  • Look to UpWork or Fiverr to find help on tasks you can outsource. 
  • Maybe someone else handling some tasks can free you up to drum up more business. 
  • Perhaps others are even BETTER at some of the tasks you handle!

#76.) What item do you want to buy from the money you make from this business? Can you make that motivate you?

Some people aren't motivated by a money goal, but rather what that money goal represents. For example:

  • If I make $100,000 more I can buy a brand new Tesla.
  • If I make $100,000 more I can buy a pool.
  • If I make $100,000 more I can buy my parents a new car.

#77.) How much money would it take to “level up your life” right now? How can you make your business hit that number?

Think about what leveling up your life would include. 

  • To level up my life: I need to be able to afford a $3,000/mo apartment and $5,000/mo in expenses. 
  • To level up my life: I want a house twice the size with a pool. 
  • To level up my life: I need a podcast studio in my home.

#78.) Which social network brings you the most customers?

Instead of trying to half-ass all the social networks, what if you were to spend all your time dominating one?

  • Different platforms appeal to different industries. Find yours. 
  • Pinterest is great for visual stuff, food, fashion etc. 
  • Twitter is great for investing, tech, humor etc.
  • Instagram is great for health, fashion etc. 
  • Figure out the social platform you like best, have a natural advantage at, and can create "Cascading Content" from.

#79.) If you could build an audience on any platform, which would it be? Are you willing to spend 1 to 3 years of time on that platform?

Many people get sidetracked by all the new social platforms coming out. While I'm not saying you shouldn't jump on just to test them out, by picking a specific platform to dominate you have a better chance. 

  • Figure out which social platform you like the most, and go hard on that one. 
  • For me personally I enjoy Twitter and YouTube, all the rest I only auto-update through Buffer, but don't spend time on. 
  • Ironically if you get lots of traction on one platform, you can much easier parlay that audience into another platform....this is better than half-assing multiple platforms at a time.

#80.) How big is your email list, and how are you growing it?

Off all the marketing channels, almost every company would opt to grow their email list over any other channel. It's because you control this channel fully, and own the interaction with the customer. 

#81.) What’s an untapped market for your services?

Sometimes the people you think need your services might not be the best fit. 

  • I've seen web designers that create webpages for people who pay $100, but then see web designers who only focus on financial companies who need similar websites but they will pay over $100,000 for it. The industry you cater to matters. 
  • Can you go "upstream" with your services? 
  • Who pays the most money for services like yours? I realized early when I was doing SEO work that some clients would pay $500 for a projects, and others would pay $5,000+ for the same project. This taught me to look for higher paying customers and go for those. 

#82.) What’s a weird way a customer uses your product?

Sometimes these weird edge cases become your biggest sellers of products, and can help you branch out into different industries. Here's three examples from my first eCommerce company that sold rave equipment and light up and glow things:

  • A plumbing company bought 50+ packages of "finger lights" used by ravers. I called them up to ask why and they said, "Our plumbers have to climb under sinks and cabinets and sometimes can't see, so they put these finger lights on their finger to light things up." 
  • I used to think 16 year old ravers were my target audience, but they rarely could afford more than $20 on an order. However 35 year old moms buying light up stuff for their child's birthday would routinely spend $200 to $300 per order. So I started catering more to this crowd.
  • I would get $1,000+ orders from wedding planners and party planners, so I started advertising to that group of people. I never thought running a RAVE COMPANY would morph into a party planner company.
  • In Copywriting Course I sold a course, and would do a monthly Office Hours to help people re-write their copy. This feature was more popular than the courses, so we created an entire community just to re-write people's copy.

#83.) Is it possible to double your business this year? What would you have to do for that?

I bet you know how to double your business, but haven't done the steps required. 

  • Maybe figure out the top 1 to 3 activities that make you the most money, and do more of these. 
  • Sometimes just getting in front of other people's audiences can be the answer. Can you go on a podcasting or guest-posting tour?
  • How has someone else in your industry grown a bunch? What did they do? 

#84.) Is there a small company or tool you can buy to expand?

Sometimes taking over someone else's small project can be a good fit. Have you looked around to see if you can acquire a small business or website, apply your own magic to it, then grow it?

  • Flippa, Empire Flippers, and Micro Acquire are all places you can browse.
  • You can also search Product Hunt or others to find small tools to buy from developers who created the tool as a side project, but don't dedicate time to it.
  • Figure out what you're good at.....maybe Ads or Copywriting, and see if you can apply your magic to the project.

#85.) Do you have any sources of low-maintenance passive income? Can you create any? A book, a course, a digital product?

One thing that takes the pressure of your business is having an income that doesn't depend on your main businesses. Having income redundancy is a huge weight off your shoulders.

  • Let's say your main website goes down for a full month, do you have other sources of income? 
  • Can you create some small products like a self published book, a small digital product, or an online course to supplement your main income?

#86.) Is there a process you do right now that could be automated?

Humans are good at critical thinking and making decisions. Computers are good at doing exact commands at certain times. Maybe there's some tech you can put in place to replace a process you manually do?

  • If you have trouble scheduling posts, perhaps getting software to auto-schedule for you would be a great fit. 
  • I used so spend so much time just scheduling meetings with people, but then implemented Calendly and bypassed all that frustration. 
  • I bet there's 1-3 process you do right now that can be nearly 100% automated with cheap or free software tools out there.
  • When I ran HouseOfRave I would manually copy-and-paste orders from my website to the fulfilment warehouse. This took me 1-2 hours a day. There were all sorts of weird issues that would happen needing my attention, so I thought it was impossible to outsource to a computer. I found a cheap plugin that did the exact thing, and it went from an hour a day to 1 minute.


Neville Medhora - Copywriting Course


P.S. Do you have any helpful questions you ask yourself to improve your business? List them in the comments.

P.P.S. We have a "Business Question Generator" that will pull up one of these questions for you to answer at a time, it's super helpful!





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I like the questions list! I see you are giving examples under each question in the blog. Actually, I can answer quite a few of them straightaway, but not all of the questions pertaining to marketing.

So I guess if you have no ready answer, you should reconsider these questions. Is that the aim?

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  • Administrator

Thanks Jason, glad you liked them! Super helpful to ask these every once in a while.

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"You can sell high quality sweaters for squirrels, but there might not be enough demand to make it a full time business."

In my yard, there would be plenty of demand 😂

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No problem Eric! 

At the end you can download the entire list in a Google Doc format (you're already on the email list so it won't send you any additional emails except the download link). 

Hope you enjoy these.....I have personally found these EXTREMELY helpful!

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