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Be the Poorest Person in the Room
Be the poorest person in the room

Inherently, entrepreneurs are introspective and seek to continually improve how they live and run their businesses. The pursuit of excellence is in our DNA. And it was with this thinking the mantra of surrounding yourself with smarter people or being the dumbest person in the room, came to be. Mostly, it’s all about challenging yourself to think bigger, better and brighter. Being around ‘smarter’ people sharpens your ax and makes you think your thoughts through without bias.

There is one other similar mantra, although not as popularly known, I think every entrepreneur should try to live by as well…

Be the poorest person in the room as often as possible!  

Unless their wealth was inherited, *rich people are typically very smart, emotionally detached and incredibly efficient with their money. 

*Your definition of rich will change the more money you make. In your mind, you’ll likely never view yourself as rich if you are routinely the poorest person in the room. That’s a good thing.


What’s Your Emotional Connection to Money?

How one saves, invests, spends, donates, borrows and generally views money, more often than not, dictates how much they have; and the level of stress (or lack thereof) relating to their personal finances. 

Everyone has their own unique relationship with money. I initially realized this at one of my first jobs as a bank teller… it became even more evident over the last decade investing in startups.

From my experience, most people have an unhealthy relationship with it. For some, money is a way to keep score in business, while others view it as the most coveted asset and continuously think about it (this mindset is restrictive on achieving your maximum entrepreneurial potential because it runs counter to taking significant risks). Certain people think it is elusive, while pragmatists view it as a means to an end. And then there are those who think it is the root of all evil… these people rarely ever have much of it. For the record, stay as far away from these people as possible. While being pessimists, they’re also the same folks who will dissuade you from starting your own business, but yet when you’re successful, they’ll tell you how lucky you are. Lastly, there are those who hoard money because they are inherently cheap or worried about financial hardship, which in their mind is always right around the corner. 

The healthiest view on money for entrepreneurs of the list above is to view it as a scoreboard or take the pragmatic approach (a means to an end). 

What has given me a healthy, and strategic, view on money, is spending a lot of time with people who are self-made and financially wealthier than I am.


Have a Healthy Relationship With Money – Surround Yourself with Richer People

If you want to develop a healthy relationship with money, while not being bashful about pursuing more of it, find a way to frequently be the poorest person in the room. Conversing with successful and ‘richer’ entrepreneurs is motivating, enlightening and keeps you level-headed. 

If you just made $10 million last year, try and hang out with billionaires; and be a sponge. Ask questions. Be dumb. Being around that level of entrepreneurial success will make you feel like you haven’t achieved all that much in business (which is a good thing), while showing you how to continually grow as an entrepreneur, positively impacting more people while increasing your income. 

When I first made what I thought at the time was a lot of money, in a way I didn’t know what to do with it. Better worded, I didn’t know how to best proceed and use it to grow, both as an entrepreneur and member of society. It felt like I had ‘made it’ financially, and contentment started to seep in. As a result of that contentment, I made several poorly thought out financial moves which, looking back, I can’t understand the reasoning. However, as time went on and I became more consistent with commercial success, my social circle grew and started to include enormously successful entrepreneurs. Their accomplishments, both in life and with money, were humbling, and made me realize how ignorant I was to what financial success really was…


The Benefit of Hanging Out With ‘Richer’ Entrepreneurs

These mentors, aside from running several insanely successful businesses, ran charities, spent summers with their grandkids, started youth programs for troubled kids, and were always looking to fund or start a new business. Their appetite to take on further risk and build companies from the ground up was insatiable, despite never needing to make another dime for their great, great grandkids to be set for life. And how they calculated risk was so much more efficient and intelligent than how I did. They quite literally changed how I invest today by merely altering my view on risk…

I would listen and ask questions more than share my opinions during our conversations, fascinated with how differently they viewed money. Initially, almost every theory they had about money, credit, and risk was different than mine. And their motivations to earn more were very enlightening. They sought maximum positive impact with capital, whereas I searched for maximum ROI… 

A positive return on investment almost always originates from providing something people need or want to make their lives easier. This is just one perspective I learned from being the poorest person in the room. 

Tim Ferriss wisely stated, “You are the average of the five people you most associate with.” If you want to be a better entrepreneur, and positively impact more lives while growing your personal wealth, seek to be the poorest person in the room. Good things happen when you’re routinely listening and looking up. 

Stay hungry,





P.S. Much of successful entrepreneurship is about your mindset. I delve deep into that component of business in my weekly newsletter. Sign up for free below. Only my best content will land in your inbox.