13 Questions I Think Entrepreneurs Should Constantly Ask


1 - Do I need to replace one of my mentors?

Mentoring is a key piece for entrepreneurs to move their initiatives forward. A great entrepreneur knows that he or she isn’t the smartest person, but the most resourceful person.

That’s why entrepreneurs have individual mentors for each of the key pieces of their lives. They have individual mentors for areas of their lives, such as personal, professional, fitness/health, spiritual, and any other area the entrepreneur deems necessary.

I can speak from experience in that mentors come and go as an entrepreneur changes gears in their professional and personal lives. For example, I changed from being a lifestyle business to being a business that’s set to scale. That meant I needed to replace one of my business mentors who excelled at lifestyle business structure to a mentor who has vast experience with scaling businesses with the intent of selling.

2 personal stories about the value of mentorship:

Story #1. I got married in 2010 while my business was exploding. We topped the million dollar revenue mark and were set to double that year. Things were looking great…or were they?

My wife and I were business partners, working nonstop day in and day out. Since we both worked in the business, our date nights soon became work sessions. At the time, I didn’t see it because I was focused on growing my business and didn’t have the right mindset for managing a personal and professional life. It was all business all the time.

There was no marriage, only a business partnership. And fortunately it got so bad so quickly that we both realized we needed help and in a big way! Through a mutual friend we were introduced to a man named David who specializes in young married couples. We had no idea what we were in for, but David will always be my #1 mentor and the greatest thing that ever happened to Katie and I.

Today, our marriage is #1 and the business is #2, something I never thought would happen! David showed us how to make life decisions as one person instead of two different people wanting two different things. The list goes on and on, but my point in telling this story is to show the value of not just a mentor, but a qualified mentor. Imagine if I asked one of my business mentors for advice; I may have gotten a completely different answer!

Story #2. I struggled from flailing between lifestyle business and scaling. One day, I wanted to stop all growth and spend our efforts on staying small, stealthy, and in the lifestyle industry. The next day I wanted 100 clients, venture capital, and take over the world! This is a horrible concoction for keeping processes streamlined in an organization! When goals change every single day, it’s pretty much impossible to run a business. While I thought it was normal to keep changing my mind, I started to realize that it couldn’t go on forever.

Meet John. John is a neighbor of mine who has tremendous entrepreneurial experiences ranging from running a lifestyle business to being founder and CEO of a billion dollar publicly traded company. Later in this article I talk about regularly seeking the assistance of your rolodex, and this is a perfect example.

I reached out to John and asked to set up a meeting where I can share some entrepreneurial struggles I was going through. The advice I was about to receive truly changed the way I saw my business forever! Here’s what John advised me to do:

“Jeff, the decision to grow or not grow is not a decision for you to make. It’s a decision you need to make with your wife and both of you have to define exactly how you want to live your lives. If you decide to scale your business you will most likely be on the road all the time, working late hours, but you will have a jet and a huge business. There are pros and cons, but put those aside. None of it matters if you don’t start with talking with your wife.”

To John, this was just something natural for him. For me, this was one of the most valuable pieces of information I ever heard. It made the next year of marriage and business crystal clear, and we never bounced back and forth again. We decided to stay small, stealthy, and lifestyle despite having multi-million dollar revenue. After one year, that decision was reviewed and we wanted to make a run at scaling!”


2 - What are the intentions for growing my business?

Sounds simple, right? I cannot tell you how many entrepreneurs I’ve met who say they are growing their companies because they want to make more money (please don’t get me wrong… you went into business in order to build your business and reap fruits from your labor along the way, but it’s also important to do regular checkups on your motives).

Then I ask them this series of questions (followed up by a simple exercise):

How much money is it costing you to grow?
How much relationship stock is it costing you to grow?
How much of your health is it costing you to grow?
How much in missed kid’s sporting events is it costing you to grow?

FACT: There are many other precious resources that must be sacrificed to grow your business than just time.

Fill in the blanks of this little quiz:
1. Growing my business will give me more ___________________________ in my life.

2. Growing my business will deprive, or take away, _________________________________ from my life.

3. Quality of life means ________________________ to me.

4. The most precious resource in my life is ____________________________.

If family is first and quality of life means everything to you, then your work schedule should consist of 40hrs/week maximum. And you may want to turn your business into more of a lifestyle business. Otherwise, money is what you are worshipping, and growing your business is the only thing that matters in your life. And that is perfectly fine! Just be careful not to have regrets when you’re lying on the death bed.


3 - Am I living a balanced life or am I out of whack somewhere?

The million dollar question and, oftentimes, the sore spot for a lot of entrepreneurs. I always struggled (and still do struggle sometimes) with this one, because the easiest thing to do in life is work! I’m convinced that it’s so easy to an entrepreneur because it’s not really work at all. It’s what we absolutely love doing! And thats’s where the problem lies or can potentially arise.

The best remedy is to define your life purpose– not to be confused with your business plan. Life purpose is a specific blueprint that outlines your vision, mission statement, core values, and the tactics you need to employ in order to accomplish exactly what you want in your personal life. When you know your life purpose, it’s a lot easier to put work on the side because work doesn’t define you! Something else in life has taken over, and you won’t rest until you reach the satisfaction from living out your life purpose.

A simple rule of thumb:
Anyone can work 18 hours a day. Try working 6-8 hours a day and make the same amount of money. If I can do it, anyone can do it!

There’s nothing more saddening to hear than a person making $600k and working 100hrs+ every week. Their quality of life is null, their revenue per hour is way too low, and their potential for burnout increases by the week.


4 - How will people remember me when I’m dead?

I enjoy challenging myself with this question regularly. It re-calibrates my priorities and keeps my efforts and thoughts aimed outward towards others, instead of inward- something I struggle with greatly.

It’s simple for me to be selfish, self-centered, and self-serving, but I have found if I truly desire to make an impact on the world (and leave things better off than when I found them), it is very important to start looking beyond one’s self.


5 - How can I be a ladle instead of a spoon? (A spoon is used to serve oneself, a ladle is used for serving others)

This one sounded very bland to me when I first heard it, but knowing what I know now, this is one of the most important things I feel all entrepreneurs should ask. I say that for 2 reasons:

*First, there is a simple and unspoken rule that says when you focus on helping people FIRST (meaning you put them ahead of helping yourself), they want to help you back! Why? Because you’ve shown them something called character– the very thing that gets ruined when you start off conversations with the word “I” and then continue on and on about how great you are and how great your accomplishments are!

*Second, helping people feels awesome! So some call it selfish, and I am not getting into that topic right now. All I am saying is that helping people produces a great sense of accomplishment, self-worth, and life satisfaction.


6 - Should I invest traditionally or invest back into my business?

401k and entrepreneurialism– there can be an entire book written on this subject! For this one, I want to share my personal insights on it (some will agree and some will certainly & passionately disagree):

It all starts with a simple word called VALUE. In my first business I never understood that simple word. I was selling a product that, because of my own stubbornness, turned into a commodity. What does that have to do with a 401k? Hear me out here…

In my second business (the current one), I learned that when you provide VALUE (and high levels of it), you can continue trading VALUE for money as long as you’d like to. Therefore, I have a very strong level of confidence (aka conviction) that if my current business went under, I can start another one (I already have 2 emergency preparedness plans in place), and start generating revenue almost instantly.

My appetite for storing money in a place that requires crossing my fingers and HOPING I get a return…why not invest in the sure bet– myself?

My plan is to keep 6-months worth of emergency cash on hand and invest into things that allow me to grow as an entrepreneur so that I can continue adding more value to my clients and, in turn, making more money (buying a beach house, joining country clubs for entertaining, investing into my systems, and so on). It’s a continual process that a non-entrepreneur will poo-poo 10 out of 10 times.

Fact: If you invested $10,000 into my company 6 years ago (and I’m certain the same can be with your business), you would be a millionaire today. Why in the world chase a 10% return in the stock market (or money market accounts) when you can invest your money into yourself and master the art of value creation, which translates loosely into making money. Spend your money mastering VALUE and how to create it, and the last thing you would ever want to do is give money to an investor because you can create 100x the returns by betting on YOURSELF!

If don’t think I’m crazy yet, you will after you read this article because I 100% agree with this guy’s approach: 13 Reasons Why a 401k is the Riskiest Investment you can make


7 - Will I ever REALLY retire or is that for other people?

I find myself asking this question all of the time. Let’s identify the 3 schools of thought:

a. Young entrepreneurs are told, “You will want to slow down at some point in your life,” but they know in their heart they never will. It’s impossible to ever know the answer until the young entrepreneur grows older. There is no right or wrong answer here, just that the entrepreneur follows his/her own heart.

b. Entrepreneurs know they will be doing deals for the rest of their lives, and it won’t be just for money, but it will be for the kill.

c. Successful entrepreneurs hate the word retirement, and the thought of ever having to slow down gives them a tremendous feeling of unease.

What does this amount to? In my opinion, setting aside too much of your earnings in your prime earning years restricts an entrepreneur from doing all of the great things they want to do during these prime earning years, thus hindering them “taking over the world,” which is what they ultimately want to do!


8 - Am I legally vulnerable?

This question is one that needs to be visited on a weekly basis because rules, regulations, and laws change regularly. For example, Killer Shark works in the medical space and faces constant change from regulatory boards, such as HIPAA. That means we have a tremendous need for keeping our products and services compliant to the ever-changing rules and regulations of how medical records get handled, as it relates to digital transmission.

I would’t take it for granted that your law firm will be proactive on seeing blind spots. While some firms may do this, there are many who will sit back and wait for you to call them. I strongly recommend reviewing your business model quarterly with a business attorney who specializes in your exact industry. For example, I always used a firm who was noted for their business acumen in regards to contract writing and litigation. However, I was missing out on an entire opportunity. It wasn’t until engaging a firm who focuses exclusively on HIPAA (my company focuses on the healthcare space) that my model, systems, and procedures were better protected legally.

  • Example: Sending an old traditional fax (using one of those clunky, outdated fax machine things) is HIPAA compliant, but using e-fax is not! We never knew that until hiring a HIPAA-focused law firm who knows the ins and outs and all the little intricacies involving medical records transmissions.

Some other examples of legal vulnerabilities I’ve personally seen (some of these are tiny, but can pose enormous legal issues in the future):

  • Umbrella policies either too big, too small, or non-existent
  • Operation as a sole proprietorship when there is too much risk at hand
  • Disclaimers needed in email signature, but not present
  • Adding unapproved emails into your autoresponder system (people hit spam)
  • Spam being sent from your server that you don’t even know about and your website gets blacklisted
  • Business contracts that are way too “loose”


9 - Am I leveraging my contact list effectively?

I personally deal with this one on a weekly basis. As a connector who has built a tremendous rolodex of business owners, VIP’s from a multitude of different industries, athletes, and many other people I’ve met and developed relationships with, it’s critical to regularly review my list and determine how or if there are ways to create strategic partnerships or leverage these relationships to grow my company.

Examples of the many different ways I like to leverage my list:

  • When I start working with a new client and something about them reminds me of someone on my list, I shoot a quick note saying “I was thinking about you today because…”
  • I try to contact 5 people in my list each week. But it needs to be someone that I either haven’t spoken to in a long time or that I normally wouldn’t speak to.
  • Each month, I try to connect at least 2 people in my list. I will send an email saying something along the lines of “John, something made me think of what you said a few months ago about needing xyz service. I just met a really neat guy who owns xyz company so I wanted to connect you guys and see if there is a fit. Please do not feel pressured or compelled to connect. I just wanted to try and help.”


10 - How can I live healthier?

Successful entrepreneurs know they need to be healthy in order to continue living their dream! If you focus on health and fitness, great job and keep it up! If you don’t, here are some of the most important inspiration/medical articles that you may be able to pick up a nugget from:

  • Every thing that goes into your mouth is either killing you or helping you live longer.
  • TRIGLYCERIDES: (a lot of times caused by heavy drinking) measure fat in your blood. This number is pretty important to know! The only way to know this number is from a blood test. Get yours today.
  • CHOLESTEROL: Most have a general understanding of this one, but there are lots of great details here that may help you understand it better: WEBMD cholesterol management center

I will tell you from experience that feeling healthy does not mean you ARE healthy. Only a full physical and a blood test can identify your actual level of health. Here’s my story:

When I was 33 years old, I was 100% focused on growing my business and having the time of my life– lavish lunches, great steak dinners all the time, and way too much alcohol consumption.

At 6ft, 195lbs I felt super healthy until I went in for a full exam– sky high blood pressure, scary high cholesterol, and a triglyceride count that was 3 times what it should have been. But remember, I FELT healthy. There was nothing bothering me and I had absolutely no symptoms at all. I was left with 2 choices: change my lifestyle or go on medications. After all, the doc wants to prescribe as many pills as possible so telling me everything is hereditary was in his best interest. Sad but true.

I opted for changing my lifestyle and dropped my cholesterol naturally by cutting out egg yolks, milk, and greatly reducing my red meat and cheese intake. Curbing my alcohol consumption then dropped my blood pressure into the safe zone. I also added a minimum of 3hrs/week of rigorous exercise.

My point in telling you all of this? To help. So I recommend you get a good screening from your doc and start adjusting your lifestyle habits as soon as possible. The longer you stay around, the greater impact you can make on the world 🙂

11 - Tragedy strikes…I am rushed to the hospital and I have one last statement to make to my COO about how to run the company so it flourishes. What is it?


12 - What time wasters can I eliminate?

This one amazed me when I finally understood that time wasters are very sneaky! They aren’t necessarily right in front of you, and they usually disguise themselves in the form of pleasure (social media, texting, etc).

One of my advisers told me the following:
“Every time you are within elbow reach of another human being, you end up landing a new client.” I let that sink in over a few days. What was he referring to?

Then it hit me. I looked back at all the clients Killer Shark on-boarded, and to my surprise, all have entered our “family” due to face-to-face interaction I’ve had with either that person or someone they knew and it became a referral! What does this all mean in regards to time wasters?

For me (and this may not apply to others) using social media is a time waster. It hasn’t landed us even one client, and when I get sucked into Facebook, it means that I am not doing that ONE thing that drives my organization, which is being in front of people day in and day out.


13 - What part of my processes can I automate?

  • Proposal template
  • On-boarding
  • Marketing funnel
  • NOT content
  • Recurring billing
  • Auto-responder to inbound emails

You should never wait to develop a rock solid secession plan. The time to build one is now. There’s one side of entrepreneurs who feel we are invincible, but the reality is that tragedy can strike at any moment. You’ve worked so hard to build your business, and you owe it to your family and employees to ensure it flourishes when your time is up!


A very important (in my humble opinion) bonus question:

What is the moral compass in how I make decisions?
This is certainly one you don’t see very often in the business community, but I feel it’s incredibly meaningful as we look at the entrepreneur as a person. Sure, anyone can create a business and work 100 hours/week and make money. It’s really not that difficult to do! You break the rules, bend the truth, and sacrifice everything you can to trade for the almighty dollar. It’s sad, yet unfortunately it’s the way so many entrepreneurs live their lives.

The good news…there is a better way!

For the bigger portion of my adult life, I always allowed my external surroundings to dictate if things were right or wrong. For example, if everyone around me is doing xyz then it must be okay, and if it wasn’t, I would justify a way to make it seem right in my mind!

Somewhere, somehow there has to be absolute truth. Unfortunately, many will question that statement, maybe disagree harshly, or even throw a fit! “This Jeff guy is really some kind of ________________!!! How does he get off saying this?”

Here’s my point: It’s up to YOU (and nobody else) to figure out the most logical place to get your truth. Mine comes from the Bible, where you find the answer to every single business situation you can ever encounter, every single relationship situation you can ever encounter, and literally every answer to every question you’ve ever had.