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Small Business Big Challenge

Small Business Big Challenge

By Lionel Legry

At its core, the "Small Business Big Challenge" podcast, hosted by entrepreneur Lionel Legry, dives into essential skills, values, and mindset to better prepare entrepreneurs and seasoned business owners to build a sustainable small business. We will talk about Startups, Leadership, Finance, IT, HR, Marketing, Customer Service, Compliance, Social Media, and Current Events.
Ultimately, "Small Business Big Challenge", is all about building a more ethical, inclusive, and resilient business.

We will offer:
- Tutorials
- Interviews
- Essays
- Coaching sessions
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Currently playing episode

8- Living your Passion with Dave Combs

Small Business Big ChallengeMar 01, 2022

30- Automating and Outsourcing with Michelle Thompson
Jul 19, 202232:39
29- Search Engine Optimization (SEO) with Brandon Leibowitz
Jul 12, 202235:34
28- Cannabis Marketing with Johnathan McFarlane

28- Cannabis Marketing with Johnathan McFarlane

My guest today is, Johnathan McFarlane.  
Johnathan started in the fitness world, working with big brands and superstar athletes like NFL star Rob Gronkowski and UFC legend George St. Pierre.

He is now, director of Strategy at Hybrid Marketing Co, the world’s largest cannabis-focused marketing agency where he builds creative marketing and advertising solutions that circumvent the tight restrictions placed on the rapidly growing cannabis industry.

Johnathan lives in Denver Co, with his wife and a 4-year-old. In his free time, he is Hiking and fundraising for Ukraine.



Unlike most states, which have legalized Cannabis via ballot referendum, New York doesn’t have much of a tradition or infrastructure around statewide voter initiatives. Therefore, it is up to the State Legislature to propose and vote on new legislation, that will be signed or vetoed by the Governor. The debate generally gains steam every spring during budget negotiations, when the Governor introduces a budget proposal for the following fiscal year.

In New York, cannabis for medical use started to be legal in 2014.

In 2018, New York state started a comprehensive study to gauge the likely impacts of legalizing recreational sales which concluded that “The positive effects of a regulated cannabis market in NYS outweigh the potential negative impacts.”
There were many debates on whether or not municipalities would be able to ‘opt-out’ and on the push to ensure a large portion of new tax revenues would be invested in communities of color which have been most affected by what most now see as historically racist and damaging enforcement of cannabis laws.

As of today, New Yorkers are now allowed to possess small amounts of cannabis and smoke, ingest, or consume cannabis products. However, the timeline for dispensaries to open and sales to kick off remains distant. The law doesn’t provide a specific timeline, but the first sales aren’t expected until the end of this year or later and it will take another 18 months for New Yorkers to be allowed to cultivate a small number of plants at home for recreational purposes.

While many small businesses are awaiting the state to issue licenses for farming, dispensing, and delivering cannabis products, there are many unanswered questions, and these businesses wonder how they will pivot their business to cannabis and position their product in the market.

Jul 05, 202238:48
27- Tax Deductions with Wendy Barlin

27- Tax Deductions with Wendy Barlin

My guest today is Wendy Barlin,  
Wendy is an immigrant from South Africa who came to this country with nothing but a bag of dirty clothes and a CPA license. Today she is the owner of About Profit (her website is: She is the author of 2 books: “That’s Deductible!” and “Never Budget Again”. She has been an educator for small businesses for over 25 years and has made multiple TV appearances.
Wendy lives in Jacksonville, FL with her husband, 2 kids, and a big fluffy dog.


That’s Deductible!

Jun 28, 202225:23
26- Early Startup with John Cameron

26- Early Startup with John Cameron

My guest today is John Cameron,   
John wanted to follow in his father’s footsteps so he started a home-business service company and later and cofounded the “Student Business Launch Program” where he helps students get hands-on marketing, sales, and management experience by starting their first business while they are still in university and get the coveted 2 years of experience by the time they graduate. Discover More about John:

Jun 21, 202226:57
25- How to Hire and Keep Great People with Mitch Gray
Jun 14, 202242:09
24- Payroll with Charles Read
Jun 07, 202244:06
23- Essay on Industry 4.0 - Part 2
Jun 02, 202220:32
22- Essay - Industry 4.0- Part 1
May 31, 202221:30
Teaser - Industry 4.0

Teaser - Industry 4.0

Teaser for Episode on Industry 4.0

May 24, 202206:39
21- Asset Protection with Jeremy Streten
May 17, 202237:09
19- Storytelling with Robert Kennedy, III
May 10, 202234:48
18- Trade Secrets- What they are and how to protect them

18- Trade Secrets- What they are and how to protect them

Many small business owners and startups don’t realize they have trade secrets to protect. This is why we are going to talk about Trade Secrets and how to protect them. I hope that by the end of the episode, you realize you already have or will have TS and will take steps to start protecting them.

Here is the official definition:*

A trade secret can be a formula (like a recipe), pattern, physical device, idea, process, or compilation of information that satisfies 2 things:

1- provides the owner of the information with a competitive advantage in the marketplace, and

2- is treated in a way that can reasonably be expected to prevent the public or competitors from learning about it, absent improper acquisition, or theft.

Basically, it is something that gives you a competitive advantage because it is secret. So you need to recognize it and protect it accordingly.

#IP #Trade Secrets #Protection

May 06, 202211:41
17- Copyrights
May 03, 202213:48
16- Danny Decker - The Automatic Marketing Machine

16- Danny Decker - The Automatic Marketing Machine

My guest today is Danny Decker.

Danny is a direct-response copywriter and marketing consultant for ambitious entrepreneurs.

Danny is also the co-author of a new book that came out last week entitled The Automatic Marketing Machine. This book aims to help ambitious business owners learn how to stop wasting money on marketing that doesn't work / and create simple, effective marketing systems that generate a profit.

How to get in touch with Danny and learn more about his book "The Automatic Marketing Machine":




Apr 26, 202231:08
15- Trademarks and Service Marks

15- Trademarks and Service Marks

#Trademark #IP #Intellectual Property #Registered Trademark #Risk Management


Did you know that Cellophane and Aspirin were Trademarks that became generic terms and lost their TM!

We are talking today about:

Company Assets Intellectual Property What is a Trademark Types of Trademarks What is difficult to Trademark [Game with sound marks] How to register a Trademark  TM Vs R USPTO.GOV Don't infringe another TM

Kalyan C. Kankanala:

“Every Trade Mark you Build adds to the financial value of your business, much more than your tangible assets”

Apr 19, 202218:46
14- The “Dirt Game” with PJ Riley
Apr 12, 202236:33
13- The entrepreneur Mindset

13- The entrepreneur Mindset



Video: The social responsibility of business | Alex Edmans | TEDxLondonBusinessSchool

Book: Anyone Can do it – Sahar and Bobby Hashemi

Video: First give, then receive: Nong Poonsukwattana at TEDxPortland

Study: Diversity drives better decisions

Video: Are We Automating Racism?

Podcast: NPR – The indicator- Companies get political

Companion PDF File

Put your ideas on paper Think of your business as a responsible Citizen Augment the Other Partner with your customers to solve a problem Adopt Lean or Agile Thinking for every facet of your business Be Comfortable being uncomfortable Embrace diversity Be curious, keep learning & Seek Mentorship Seek expertise and become partner with your experts Don’t Give up

#leadership, #mindset, #lean, #agile, #diversity, #expertise, #entrepreneur, #startup

Apr 05, 202223:05
12- Essay - On Negotiation

12- Essay - On Negotiation

#Small Business #Negotiation #Deals #Ethics #integrity

Small Business Big

Today, I am taking you to the beginning of the 20th century and I will tell you a story involving the 22nd amendment, copyright infringement, and the interesting negotiation talent of the campaign manager of Teddy Roosevelt

"This story reminds us that reaching an ethical judgment is sometimes difficult.
True integrity requires you to be able to distinguish all the shades of grey between black and white.
But as a negotiator, it matters. Acting with integrity matters! Respecting the other DOES matter!
Do NOT believe these books that tell you that bluffing, puffing, misleading, and not correcting wrong assumptions are 'truthful hyperboles'.
They are lies and nothing but lies."

For more info go to: Small Business Big

Mar 28, 202215:52
11- Leadership - Business Model  & Business Plan

11- Leadership - Business Model & Business Plan

#Leadership #Business Plan #Business Model #Business Model Canvas


Business Model Canvas:

YouTube- Business Model Canvas Explained with Examples

YouTube-Osterwalder explaining the Business Model Canvas Template Gallery

Genalyte – Like Theranos but it works!

Training Videos from SBA.GOV- Writing a Business Plan

7 good reasons to write a business Plan:

Prove yourself you are ready Give your company better chances to grow Do your due diligence to lower your risks of failure Determine your financial needs Get funding Attract partners, and employees Create a guide to measure future performance

8 crucial elements in your Business Plan:

- The elevator pitch - The Team (you, partners, advisory board, future staffing need) - Your operations and user experience - The market need for your item/service - A competitor analysis - Your roadmap with major milestones - Your financial projections for the next 1 to 2 years - The Capital need (how much money are you trying to raise)

Mar 22, 202225:10
10- Commercial Insurance with Lee James and Brian Loucks

10- Commercial Insurance with Lee James and Brian Loucks

Today I invite you to listen to an interview between Brian Loucks, a business mentor with SCORE, and our special guest, Lee James.
Both Brian and Lee live in Cuba, NY, and are leaders in our community.
Lee will answer today, some questions you sent me, on commercial insurance.

Lee James:
Sales and Office Manager at Lawrence Dye Inc.
Since September 1979!
Former president of the chamber of Commerce of Cuba, NY
and current town attendant.
Married with a son and a daughter
Phone: (585) 968-1182

Brian Loucks:
SCORE mentor in Cuba, NY


“I want to open a coffee shop on Main Street, what type of insurance should I get?”

“There are hundreds of commercial insurance offers online and they all sound the same to me, how do I figure out what I need and which company to pick?”

“What are the advantages of working with an independent agent vs a captive agent?”

“I started delivering my baked goods directly to my customers using my personal car. Won’t my car insurance cover me in case of an accident?”

“I am starting my small business; my budget is tight. How can lower my premiums?”

“What information should I prepare before consulting with my insurance agent?”

“I heard insurance agents have a fiduciary duty. Can you explain what it means?”

“I lost all my inventory in a fire; how long will it take for my insurance to process my claim?”

“How often should I re-assess my insurance policy?”

“I have a small business where I cut hair from my house, won’t my home insurance cover me in case of a problem?”

“What distinguishes a great insurance agent from an average one?”

Mar 15, 202223:43
9- Startup - Lean Startup

9- Startup - Lean Startup

#startup #Lean #Agile #Smallbusiness #Minimum Viable Product #Sprint 

Join us at

Today, I will keep on stressing the importance of LEAN and AGILE.
Lean and Agile are a mindset and a method, and the more difficult part will be to adopt the mindset

The conventional way to start a business is the “Build and they will come” method

The Lean startup searches what is the right thing to build that customers want and will pay for as quickly as possible.

This method is also called the ‘fail fast method’ because instead of finding that your assumptions were wrong after you built your product or service, you get rid of your wrong assumptions at the very beginning of your journey and build a startup based on proven assumptions.

To discover what business model will work for you, you need to create what LEAN and Agile call a “Minimum Viable Product” or MVP

1. Observe don’t ask!

2. Create a Minimum Viable Product (Concept/ Customer Panel/ Smoke and Mirrors)

We will steal one great concept from SCRUM, which is an Agile framework. This concept is the concept of SPRINT. A sprint is a time frame, for example, 2 weeks, during which you create your minimum viable product. 

To think LEAN you have to change your mindset and your company culture and this is will be the most difficult part of the journey. For example, LEAN requires a culture where the team has the freedom to fail as long as they learn something from each failure that helps the team succeed faster the next time. This is a drastic shift from our culture that thinks that people who fail are ‘losers’ to a culture where people who fail are called experienced and have better chances to win the next time.

To give us some feedback or to contact us to be on the show, go to

Mar 08, 202221:20
8- Living your Passion with Dave Combs
Mar 01, 202250:36
7- Startup- What is holding you back from starting your own business?

7- Startup- What is holding you back from starting your own business?

#startup #Lean #Agile #Smallbusiness

Join us at

This episode is for all the entrepreneurs at heart that have not made the first step yet!


Do you fear financial failure?

Do you think your gender or your skin color will make it more difficult to succeed?

Do you Fear the Embarrassment of failure?


Don’t be scared of statistics!

Adopt the Lean or Agile mentality

You have to plan to succeed but prepare to fail!

Put some distance between you and your company

It is all about risk management! (See episode 4- How to approach risk)

Share the threat and the opportunities

Learn a new perspective on risk assessment.


- Change your relationship with risks. Be Risk-positive. This might be a long process that you might have to study and experiment in your everyday life.

- Start learning about the LEAN mentality and methods, it revolutionized the way I think of everything and helped me take on bigger and more complex projects. Instead of taking huge risks, take small bets and test your ideas with well-crafted experiments that will give you quick results. Then analyze your results and craft your next experiment accordingly. Small failures will lead you to an idea that works and then you can easily scale it up.

- Don’t fear statistics. Statistics are telling a story, but not YOUR story! instead, use them to your advantage! Understand why other small businesses failed so you can better prepare to prevent their story to be YOUR STORY.

- Be customer-centric!

Dr. W. Edwards Deming used to say: ‘The customer is the most important part of the production line’

Feb 22, 202221:25
6- Startup- Are you ready to start your own business?

6- Startup- Are you ready to start your own business?

#startup #Lean #Agile #Smallbusiness

Join us at

10 Questions to find out if you are ready to become an entrepreneur:

· Q1- Are you meant to be an entrepreneur?

· Q2-Are you physically and emotionally ready & able to work hard?

· Q3-Do you have the necessary time and energy?

· Q4-Are you passionate and resilient?

· Q5-Do you have a good idea or an area of expertise that solves an existing problem?

· Q6-What makes you unique in your industry or community?

· Q7-Do you have the skills to manage a small business?

· Q8-Can you assemble the right team to start your small business?

· Q9-Do you have the required skills to start a small business?

· Q10-Can you secure the proper financing?

Here is your HOMEWORK:

- Start making a schedule, try to free up some time, and find out how many hours you can dedicate to your project.

- During that time, start developing your business idea: what will your item or service solve?

- Write down your business skills, add your strengths and weaknesses. Do you know enough of accounting, do you know online marketing, will you be good with employees, are you a technical person? The list will give you the skill gap you will need to fill and the amount of time you will need to dedicate to these tasks.

- Start networking with your community and industry to find work partners to bounce your ideas with, get support, collaboration and study your competition.

- At this point, don’t look at startup cost or set a budget quite yet! You will do this when you complete your business plan. You don’t know if your idea will attract other investors or if you can scale it down. Just look at what financing you can personally bring to the table and make sure you have a 6 to 18 months reserve to live on until your business can show some profit or be prepared to work evenings and weekends until you can afford to leave your day job.

- Find a mentor or business coach that will help guide you through the startup process and help you create and validate your business plan.

And make sure you take your time… business ideas take time to mature. 

But despite the high failure rates, the long hours, the high-stress levels, and a host of other problems, entrepreneurs report consistently higher rates of happiness than wage-earning employees. And this is mostly due to a stronger sense of meaning, the ability to unleash their creativity and see the direct impact of their decisions.
Starting a business may not make most people rich, but it makes plenty of people happy.



Malcolm Gladwell - Outliers Write a Business Plan

From Desire To Mission | Mohammed Al Qahtani | TEDxNUSciTech

Feb 15, 202220:60
5- Startup - Selecting new technology

5- Startup - Selecting new technology

#startup #Lean #Technology #Disaster Recovery #Smallbusiness

Join us at

Today, we’ll review the 3 pitfalls and 5 questions you need to ask when acquiring a new piece of software or piece of hardware, and I explain why the price should be your last consideration!


1- No support
2- No Upgrade/ or infrequent upgrades
3- Difficult Conversion  to  another vendor

5 Questions to ask when selecting a new technology:

1- The company (you are trying to find out if they will be around in 5 years)
2- Is this application a standard for my company size and industry?
3- Does it have all the features I need? (Ask for a demonstration or free trial)
4- What is the level of support?
5- What is the Price (It should represent how critical the app is in your process)

What is Open-source, what are the pros and the cons?
Importance of a good backup strategy

Join us at and leave us a message!

Feb 07, 202226:28
4- Leadership - How to approach risks and make a solid Risk Management Plan

4- Leadership - How to approach risks and make a solid Risk Management Plan

#startup #Lean #Agile #Smallbusiness

Join us at

Too often, young entrepreneurs have a limited concept of risks and rarely know the process to mitigate them. They often just disregard them which is definitely the worst approach! For example, there is an estimated 40% of businesses that have no insurance whatsoever!

Today, we will go back to the definition of risk and expand on it! We will also learn how to create a good risk management plan.

To help you create your plan, download the companion file which includes a template

Here is the 6-step process to manage risks:

1- Objective at risk (goal/ what are you trying to achieve? Being successful = use your mission statement)

2- Identify the risks:
= what could hinder or help me achieve my goal?
= understanding uncertainties in the right context and environment.

3- Assess risks and prioritize them (what is the probability and severity of impact? And which risks are the most important?

4- Create a risk management plan: (What can be done to increase opportunities and decrease threats?)

5- Execute the plan

6- Monitor & Review (did it work, if not what else can we do? / Are risks different today?)

4 ways to act on a risk:

· You can eliminate the risk = eliminate the uncertainty = Avoid threat / Exploit the opportunity
(ex: skydiving)

· Transfer or share the risk = threat (insurance, contract manufacturing)
Opportunities (partnership, joined venture)

· Reduce/mitigate the risk = lower probability or severity of impact
ex: sprinkler system (lower impact)
Ex: safety training = lower probability

· Accept the risk = include it in the baseline and create a plan B.
ex: If my webserver fails, my website will be down until I fix it. Plan B: I will get a backup server.

Other key concepts:

Risks are natural and everywhere, but we have the ability to managethem!

Risks are “All uncertainty that matters” not just threats

Some risks might keep us awake at night, but risks are also the opportunities that make us get out of bed in the morning!

To see the Video version:

Jan 31, 202221:38
3- Startup - Commercial Insurance Info and Mindset

3- Startup - Commercial Insurance Info and Mindset

#startup #Lean #Commercial Insurance #Smallbusiness

Join us at

Key info and concepts:

An estimated 75% of U.S. businesses are underinsured, and 40% have no insurance at all!

There are 3 reasons to have proper insurance: You, your employees, and your customers!

insurance agents owe a fiduciary duty to their clients!

your goal as a small business owner is not to become an expert in insurance!
Your goal is to learn the basic information and team up with your insurance agent to get the best policy for your specific needs, at the best rate.

To that goal, here there are 6 fundamentals you need to follow:

1- Have a basic understanding of the different types of commercial insurance

2- Know what insurance is required for your company

3- Understand the risks associated with your specific industry

4- Prioritize coverage over cost

5- Learn what will affect your insurance rates

6- Remember to revisit your policy yearly and when your business is changing

Insurance is a tool for risk management and asset protection and it is not something you acquire by spending hours price hunting on the internet but by creating a partnership with an experienced local independent insurance agent whose expertise will be put to the service of your company.

Jan 25, 202222:29
2- Startup - Create a Legal Structure for Your Company

2- Startup - Create a Legal Structure for Your Company

#startup #Lean #Legal Structure #Smallbusiness #LLC #Sole Proprietorship

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Here is what to consider when selecting the proper legal structure

- Number of owners in the company
- Your need for Asset protection
- The Tax implications (income tax, self-employment taxes, deductions)
- How you will raise your starting capital
- If you want your company to eventually go public
- Complexity and cost of forming and running your company

Don’t run your business as a Sole proprietorship just because it is simple and cheap! If you decide to have a Sole proprietorship don’t forget to register your DBA and get all the proper licenses and permits

If you select to create an LLC, make sure that:
- you have an operating agreement and follow it!
- Get EIN
- Business Bank account under the name of the LLC. Don’t commingle personal and business funds!
- Don’t think that creating an LLC offers full-proof asset protection against a personal debt

File income tax and make your annual and/or Biennial filings!

A great resource to learn about creating and filing a small business is

Make sure you partner with your attorney and tax professional to decide, set up, and maintain your legal structure and more importantly create an asset protection strategy!


From Sole Proprietorship to LLC in 10 Simple Steps! (Legally)

Jan 17, 202223:09
1- Essay- The 14th Amendment and why you should write your Mission Statement.
Jan 13, 202215:23