Challenge Everything Financial

I help sales professionals & business owners spend money on what they love, and rip out the bullshit that keeps most people on an average path to an average life.

You lead the discussion around what you value in life. 

I then help guide you to making money decisions to align with your values.

We then work together to narrow down the time it will take for you to:

* Start a business (if applicable)
* Feel confident in your money habits
* Get on the same money page with your spouse
* Retire a decade (or two) earlier than you thought possible
* Bring home more money in your "lifetime" paycheck (i.e. through tax savings)

DM me to begin investing in YOUR freedom.

Financial Planner

SaaS Employee Benefit Company

Regional Sales Director - Enterprise

SaaS Healthcare Company - Wound Care

The company is transforming the way providers care for chronic wound, dermatology, and burn patients in the value-based care era through industry-leading APIs.

We are a healthcare data analytics company that provides clinicians with accurate and objective wound measurement data and documentation at the point-of-care. Our core values are to optimize clinicians’ wound and skin care workflows, and encourage patients to take initiative in their own chronic wound and skin management.

Over 150 health institutions have integrated with The Company since 2014, automating the entire documentation process from image capture to upload. Our AI-powered solution is EMR integrated via SMART on FHIR and HL7 — when you need a full patient report or a Lund & Browder assessment for burn, it is immediately available within the EMR.

Regional Director

SaaS Healthcare IT Company

Responsibilities- 
• Managing new business sales of medical software, devices, and consulting services within Mid-Atlantic territory. 
• Perform solution demos and lead contracting meetings with decision makers and C-Level executives.
• Manage vendor relationships and drive third party business in a competitive environment.

Regional Sales Director

Client Representative

High Risk Auto Insurance Company

Cultivate professional partnerships with fellow agents to boost communication, revenue and corporate compliance. Facilitate communication with agents to respond to questions and handle issues. Inform agents on new procedures and best practices. Generate reports to identify target markets. Present information at meetings. Negotiate vendor pricing for events and meetings.

Marketing & Sales Manager

Phone Book Ad Company

Strategized with local and national businesses to personalize marketing strategies and products including websites, social media and print advertising. Managed ongoing client relationships to recognize and identify business-growth opportunities. 

Collaborated with clients on strategy to deliver a competitive edge. Attended daily meetings and weekly meetings to improve communication. Produced reports to pinpoint marketing method efficacy. Trained new employees on sales calls; documented sales activity in Salesforce.

Client Solutions Specialist

Rental Car Company

Selected accomplishments: 
 · Consistently earned repeat business by delivering an outstanding customer experience.   
 · Earned the highest customer satisfaction rating among North American airports by J.D. Power & 
 Associates.  

Interacted with customers to pinpoint vehicle needs and deliver timely service. Shared rental agreement information with customers and responded to inquiries. Communicated with vendors to set up vehicle maintenance and retail location services; operated car wash and performed vehicle pick-ups. 

Innovated marketing strategies to increase revenue; fostered local partnerships to grow business. Participated in workshops to learn time management and organization skills. Directed internal operations, motivating staff to provide superior service. 

Conducted bookkeeping and car safety checks. Educated coworkers on corporate procedures and policies.

Management Trainee

College

Taught and created leadership standard based lessons.
 · Led out-of-school requirements to help raise money for charity
 · Offered extra help outside of regular class time for anyone who needed it   
 · Graded papers and helped facilitate discussion on leadership topics

Class Facilitator

Showing Sales Pros How to Use Commission to Buy Freedom in 12 mo or Less | Financial Planner | Former SaaS Sales Professional

I teach sales ppl how to find purpose and freedom in life by using money as a tool.

TL;DR
If you make good money and want to know how to turn your commission into a repeatable, scalable, passive-income machine...follow along.

I share as much as I can right here on LinkedIn.

If you are in sales and:

• Want to take annual vacations for free 
• Hate the corporate world and want a way out
• Think commissions are taxed more than your salary
• Want to use your commission to retire in your 40s/50s
• Had a sh*tty experience with a previous financial advisor
• Pay an advisor 1% of your investments, and get no other service...

Reach out. 

My #1 goal is to educate you. 

**I want you to get to a point you don't need a financial planner.**

(Or if you feel more comfortable with one, that's ok too).

But if you want a financial planner who is transparent and knows what it’s like to grind out a sales career, I can be your partner for years to come.

If you want to level up your money relationship, DM me for a meeting.

I want YOU to be a master of your money, and do what you value most.

Let's chat and see if I am able to put MORE money back in your pocket.

-----

In the last decade+, I've spent my professional career in software sales.

But in 2014, I started becoming more knowledgeable about personal finance.

I began to learn about ways to retire 20 yrs earlier than I previously thought possible.

I knew I could help others get on a path like mine.

Most financial advisors want to only manage investments.

They take "just 1%" of your investments.

Then they don't do anything else for you.

My advisor was like that.

So I fired him.

Then I became a financial planner.

My goal: To help sales people like you.

Two ways to work with me:

1. Personal 1:1 financial advice. From investing to tax planning, from choosing employee benefits to saving for your kid's college...and anything else about money - I am your personal financial planner for $275/mo (fee can be paid from a bank account or investment account).

2. Join my Skool community, where I teach folks to DIY their own financial plan for $37/mo (no personal guidance, but you get access to all the same tools I use, with video tutorials on how to use them).

I HATE sales people in disguise.

---

I went to a new dentist w/ my 4 kids.

Before we sat down, the hygienist asked to schedule our 6-mo appt.

Before looking in my kid's mouths or asking about past x-rays, they told us about all the treatments they would need.

Wait wait wait.

Hold up.

Can you FIRST do the exam...THEN we can talk about needs for each child?

---

That dentist office ran a tight ship & was BUILT for kids:

👉 Toys galore
👉 Mickey Mouse clubhouse on TV
👉 Wheel spin for prizes to win at the end of the visit

BUT...

A well-run biz doesn't automatically mean honest advice.

***If I've learned anything from my own industry (Financial advice)...the fancier the office, the more you get "sold."

❤️ I love well-run businesses
❌ I don't love selling over serving

And I HATE prescriptions without examination.

---

Don't use a financial advisor who sells you a product before understanding your money goals.

That isn't a trusted advisor.

That's a sales person in disguise.

Sales pros: 

Don't get sold.

#ChallengeEverything #Sales #Money

Michael E. Pyle

I teach sales ppl how to find purpose in life by using money as a tool.

TL;DR
If you make good money and want to know how to turn your commission into a repeatable, scalable, passive-income machine...follow along.

I share as much as I can right here on LinkedIn.

If you are in sales and:

	• Want to take annual vacations for free 
	• Think commissions are taxed more than your salary
	• Want to use your commission to retire in your 40s/50s
	• Drink better wine and driver better cars, WHILE saving more money
	• Hate the corporate world and want a way out
  • Pay an advisor 1% of your investments, and get no other service...

Reach out. 

My #1 goal is to educate you. 

**I want you to get to a point you don't need a financial planner.**

(Or if you feel more comfortable with one, that's ok too).

But if you want a financial planner who is transparent and knows what it’s like to grind out a sales career, I can be your partner for years to come.

If you want to level up your money relationship, DM me for a meeting.

I want YOU to be a master of your money, and do what you value most.

Let's chat and see if I am able to put MORE money back in your pocket.

-----

In the last decade+, I've spent my professional career in software sales.

But in 2014, I started becoming more knowledgeable about personal finance.

I began to learn about ways to retire 20 yrs earlier than I previously thought possible.

I knew I could help others get on a path like mine.

Most financial advisors want to only manage investments.

They take "just 1%" of your investments.

Then they don't do anything else for you.

My advisor was like that.

So I fired him.

Then I became a financial planner.

My goal: To help sales people like you.

Helping you use commissions to protect your family...

Betting on sports is RUINING families.

(This post is directed at MEN - but spouses need to pay attention too)

Sports gambling is a ticking time bomb.

By 2035, I'm predicting gambling to be one of the HARDEST financial events to overcome for 1 in 5 families.

Gambling apps are incredibly good at taking your money.

And here's a line I've NEVER heard anyone say out loud:

"Overall, I'm down in gambling."

Everyone says, "I'm about even." (which is buIIcrap)

Go ask your husband right now....go ask him if he is up or down in his DraftKings/FanDuel account.

If he says he is "about even" -> you're in TROUBLE.

And you're family is likely losing thousands per YEAR to gambling losses.

----

This is NOT about shame & guilt.

This is about being REAL with yourself (and your family).

Please stop lying.

Stop lying to your wife
Stop lying to your kids
Stop lying to yourself

Having a 3rd party intervene is a very good idea. 

Therapist, financial coach, etc.

This is YOUR LIFE we're talking about.

We ALL need help at times.

#ChallengeEverything #Sales #Money

PS - Again, this is NOT about shame & guilt. 

I want people to WIN with money...and sometimes, you HAVE to have really hard conversations to WIN.

(Sales ppl are riskier than most...it's a career that you have to take risks to win - but risking your paycheck on a game is a bad risk).

3 steps to being a HIGH ACHIEVING parent:


1. Drive around until toddler falls asleep
2. Do anything you want, just be FREAKING QUIET!!!
3. Repeat steps 1 & 2 until you have all your "to do" items complete

Easy peasy.

#ChallengeEverything

Took 4 kids, but I FINALLY have this whole parenting thing down.

I turn off my engine at stoplights.

Then I immediately turn it back on.

I do this to confuse other drivers.

"How does a 2003 Toyota 4Runner have the Auto Start/Stop feature?!" - Them

"Because I have a really weird sense of humor." - Me

#StealthWealth

PS - Oh and thank you, good Samaritan...my gas cap is not actually open on purpose...it's just broken. 

But I appreciate your willingness to help a stranger out. 👊

Say NO to the 50-year mortgage.

And let's pump it to 100 years.

Nay.

500 Years.




Nay again.


Never own the home in the first place.

We'll call it the:

Really
Expensive
Never-Ending
Tenancy










RENT for short.

Why do you use Bank of America, US Bank or Wells Fargo?

I'll tell you why:

Bc your parents signed you up with the account when you were a teenager.

---

Let's put on your big boy pants on and go out and get yourself a High-Yield Savings Account, huh?

Time to grow up, Peter Pan.

#ChallengeEverything #Money

PS - link to a list of HYSAs in comments.

Ahh yes, December 1st....

...the start of an anxiety-filled month of remembering to hide the FREAKING ELF on the MOTHER F'ING SHELF every night until Christmas.






Parents, Godspeed.

"Peeing your pants is cool." - Miles Davis

"Living with your kids is cool." - Nobody

---

I love my kids.

But I want them to move out one day.

I believe they love me back.

But I doubt they want Mom & Dad moving in with them when THEY are starting a family of their own.

How to prevent moving in with your kids when you're in your 60s & beyond?

Quit putting sh*t off.

Yes, retirement is 30 years away.
Yes, you make a fantastic income and can "save more later."

But later is going to bite you in the ass.

And by then, it's WAAAAY too late.

Don't be the person who reaches out in their mid-50s who "wants to start saving for retirement."

2026 is in 50 days away...

#ChallengeEverything #Sales #Money

PS - Wouldn't it be nice to invest your commission check in a long-term plan that you and your spouse could start acting on??

Everyone to ChatGPT: 

"Explain XYZ to me like I'm 5yo."

Me to ChatGPT: 

"Explain XYZ to me like I'm 10yo."

---

Twice as smart as all ya'll.

#ChallengeEverything

Rich people use the Back Door. 👀 

(don't get mad at me, I didn't write the rules)

But when you're rich, you do things differently than common folk.

Back door is where it's at. 😎 

Keep reading if you want me to show the steps to perform the back door.

(Things are about to get messy)

STEP 1:
Make a crap ton* of money (usually $250K+ for Married couples) 

(Side note: you don't have to be married to use the back door 😉)

STEP 2:
Contribute to a Traditional IRA ($7K for under 50 in 2025)

STEP 3:
Wait a bit (usually a few days)

STEP 4:
Move that same money over to a Roth IRA

STEP 5:
Invest the money (everyone forgets this step)

STEP 6:
File form 8606 with your taxes

---

And THAT is how you execute a Back Door Roth IRA contribution for 2025.

I told you it was messy. 

**Be sure you don't have any pre-tax money sitting in IRAs before you do this. 

Because then that Back Door gets REEEEEAAAAL messy.

#ChallengeEverything #Sales #Money

PS - Not financial advice. I'm just having some fun on a Friday. 

Crap ton = $246K modified adjusted gross income for Married, filing jointly

Sorry to anyone reading this post...



Christmas is on December 25th this year.



You now have no excuse for "forgetting" to budget for gifts.









I hope the excessive white space has triggered you.





Because your excuses to overspend on Christmas because you forgot what day it is on....









....triggers me.

You make $300K+ in sales.

Income has TRIPLED in the last 5 years.

But you are STUCK.

No better off financially than you were 5 years ago.

Why?

---

What if...

...by mid-2026:

You had a plan to exit the workforce in the next 15-20 years?
You stopped fighting with your spouse over money?
You finally knew where your money was going?
You felt confident in your financial life?

What if YOU finally started to see progress?

How would YOUR life change?

---

It's possible.

***But not if you continue to do the same thing over and over again...and expect things to be different, simply because you are "making more money."

Remember...your income ALREADY tripled.

But financially, you're no better off.

---

Reach out.

Let's CHANGE your future.

I'm the guide, you're the driver.

We're gonna GO places in 2026.

So let's f*cking go!!!!!!!

#ChallengingYou #Money #Sales

Crazy way to put $1,000+ in your pocket PER MONTH...

Read about these two sales ppl.

EXAMPLE 1:

👉 John is 35yo
👉 He has $250K saved for retirement
👉 He plans to retire at age 65 with $5 million

✔️ He invests $3K/mo
✔️ His returns average 7%

He ends up with $5.3million by age 65. 🙂 

SUCCESS!

---

EXAMPLE 2:

👉 Julie is 35yo
👉 She also has $250K saved for retirement
👉 She also plans to retire at age 65 with $5 million

✔️ She invest $2K/mo ($1K less than John)
✔️ Her returns average 8% (1% better than John)

She ends up with $5.2 million by age 65. 🙂 

SUCCESS!

---

So who was the bigger success?

Julie was.

Why?

🔥 Because she had $1,000 MORE per MONTH that she didn't have to invest to reach the same goal of $5+ million 🔥 


✅ That's $1,000 MORE to spend on annual vacation
✅ That's $1,000 MORE to go on dates with her spouse
✅ That's $1,000 MORE to afford the bigger home for the family

That's $1,000 MORE PER MONTH on ANYTHING!

---

Stop saying 'NO' to better vacations with your family...and start saying 'YES' to a better investment strategy.

#ChallengeEverything #Money #Sales

PS - Making money (i.e. commissions) and knowing what to do with it AFTER you make it are different skill sets. 

Invest in KNOWLEDGE so your family can do all the things you want TOSDAY...while STILL hitting your long-term goals TOMORROW.

PPS - Not investment/financial advice. Examples assume starting point is $250K. No investment returns are guaranteed. Invest at your own risk.

Employee Benefits Consultants: PLEASE READ!!! 👇 

When you put a benefits package together, INCLUDE THE PRICE OF THE PREMIUM RIGHT NEXT TO THE INSURANCE PLAN!

I don't understand the concept of putting the price 23 pages later, in your benefits packages.

It's the equivalent of McDonald's posting their Chicken McNugget & Big Mac prices in the bathroom stalls.

Here is an example (in case you need it):

HDHP w/ HSA Plan
$140/mo
$4,000 Deductible

PPO Plan
$350/mo
$1,000 Deductible


Boom! DONE!


Youuuuuurrrrr welcome.

How to save $3K-$5K+ on employee benefits in 2026...

Choose the High Deductible Health Plan (HDHP).

Example:

PPO Plan = $400/mo
Deductible is $1,000

HDHP PLan = $100/mo
Deductible is $4,000

---

3 ways to level up your money game through emp benefits:

1. Choose the HDHP and you save +$3K/year in insurance premiums.

If you're healthy, you weren't going to hit your $1K PPO deductible anyway, so why are you paying MORE per month to be insured "better"?

2. Next, put money in a Health Savings Account (HSA) with a HDHP. Over $8K can be put into this account for a Family HSA 2026. Money put into an HSA avoids taxes! Likely at least $2K/yr in tax savings.

3. Do NOT use the HSA to pay for current expenses. INVEST the account instead. Think of an HSA like a "Healthcare 401k."

Your 80-year-old self is likely MORE unhealthy than your 40-yr-old self...so save for your wrinkly self.

Watch video to see more of my pretty face. 😘 

#ChallengeEverything #Sales #Money

Not tax/investing advice. Do NOT sleep on your employee benefits package.

Most ppl are stressed about money. Smart ppl negotiate.

Life's about choices....

Choose A, can't Choose B.

People get mad they can't have both.

'AB' - they want both.

ABs - that's what you want?

Well you can't have ALL the cookies and ALL the abs.

You can negotiate though.

✅ Control yourself, have a few cookies
✅ Realize you aren't trying to become a body builder
✅ Continue to workout, eat right the other 95% of the time

Now you have semi-abs, and cookie fulfillment. 

The folks MOST stressed over money?

They compare themselves to Warren Buffett.

Why?

Is that necessary?

Likely...N-O... NO!

What do you value? 

It's likely: 👇 

👉 A better relationship with your spouse
👉 A good income to live a good life
👉 More time with your kids
👉 To feel safe

So how do you get everything?

You list out your values & have a plan.

Eat the cookie, forgo the next dessert
Fly coach instead of 1st class, take 2 trips vs 1
Change cell phone plans to get same service, at a cheaper rate

...and so many more things.

You HAVE to start with what you VALUE.

#ChallengeEverything #Sales #Money

PS - The number 1 seller on your team has different values/goals than you. So stop comparing YOUR LIFE vs THE SALES LEADERBOARD. 

Being at the top of the sales leaderboard doesn't guarantee happiness.

But following your values will...

You're paying your financial advisor for WORSE investment results.

31% of my clients come to me FROM another advisor.

aka

👉 They left their advisor because their advisor didn't do very much. 👈 

No tax strategy
No debt payoff plans
No help with cash flow
No help building estate plans
No employee benefit strategy
No help shopping life insurance*

---

This industry is built off YOU not understanding advisor VALUE.

Your advisor doesn't know what company will hit it big...bc NOBODY does.

THINK about it. 

IF you REALLY believed your advisor knew what companies would pop off, wouldn't you already be a damn millionaire by now????

Nobody knows. 

But some ppl are VERY good at bullshitting you while wearing a fancy suit and serving you "good coffee."

Reach out if you want the truth, not some marketing approved bull crap that helps you feel all warm and fuzzy inside.

The Truth > inferior investment returns and nice coffee

#ChallengeEverything #Sales #Money

*(UNLESS the advisor got paid to sell the policy)

PS - There are WONDERFUL advisors all over the place. But the guy/gal who called you bc you were college buddies is likely NOT the best advisor. 

And also...that bank account you've had since childhood...it sucks. Grow up & switch to a High-Yield Savings Account already. 😉

Making $300K+/yr should NOT be the goal. 


A carpenter doesn't brag about how many tools they've acquired over the years. 


What they DO with those tools is what matters. 


Making money is great. 


What's better?


Knowing HOW to use money as a tool to help you get what you want in life. 


#ChallengingYou #Sales #Money

Sales person about to make a $96,000+ commission check - BUT 👇 

She's worried.

Why?

Why do many of YOU worry?

Bc companies change the rules AFTER the sale.

"Oh, commissions are actually capped." - Company
"Oh, we fudged up the comp calculation." - Company
"Oh, we can fuck with your life because there's literally nothing you can do about it when we change it up." - Company

---

If you've been in sales long enough, you've been screwed over on commission.

Read that again.

Give it time...and you get screwed over. Ask any sales person over age 50.

---

One way to solve this?

Start investing your commission AGGRESSIVELY.

👉 Real estate
👉 Stock market
👉 Your own business

ANYTHING to remove the control your company has on you.

***Bc until YOU become financially free to not HAVE to have a paycheck, you are the peasant that gets spit on....and your company is the tyrant King - doing whatever he pleases...bc he wrote the rules and will change them to benefit himself.***

---

Start pushing back!

Quit accepting that this is normal!

Protect your family!

#ChallengeEverything #Sales #Money

Parents paying 100% of their kid's college are making a HUGE mistake.

Millennials, I'm looking at YOU.

❌ Millennials got hit with massive loans
❌ Millennials are still paying those loans off
❌ Millennials don't want their kids to have student loans

And it's a mistake.

Because not only are YOU still carrying loans...

You're now putting EVEN more money into colleges vs taking care of YOU.

Dropping $80K/yr for an Ivy League is a terrible idea if your kid is gonna graduate with a Sociology degree.

Don't OVERCORRECT what happened to Millennials.

Be smart.

✅ In-state school
✅ Public university
✅ Take CLEP exams
✅ Take college classes in high school
✅ Have your kids WORK TO PAY for college

It's not a sin to work AND go to school.

It's called time management.

And it's a perfect skill to learn while in college.

Because guess what? 

The real world is barreling toward your kid...and they need PRACTICE for the real world.

Otherwise, YOU (the parent) are setting them up for failure! 

YES, YOU - the parent who thinks paying 100% of kid's college is an act of love.

It's hurting your kids in the long-term.

#ChallengeEverything

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