While managing massive student loans and debt in 2010, Kyle began to blog about his adventures in making and saving money. Readers responded and this culminated into the launch of

Under his leadership, The Penny Hoarder has grown from a personal blog to one of the largest publications on the web reaching millions of readers a month. The Penny Hoarder has pioneered a new kind of personal finance media with stories about real people and actionable money tips that make a true difference in our readers’ budgets.

Kyle is active in local politics after spending nearly six years on the road as a campaign worker crafting media strategy, directing field workers, and raising millions of dollars for important causes. He feels passionately that people should earn a livable wage no matter what their job.

On the WeFailForward podcast, Kyle shared some of his early failures and how he overcame them. As a founder & CEO, Kyle has learned how to pivot quickly and adapt to change to stay ahead in the fast-changing digital-media industry.

Failures & Mistakes I’ve Made

2004 Enrolled and left the University of South Florida after one semester to work on political

2006 Enrolled and left the University of Colorado after two semesters to work on another political

2010 Realized I had $50,000 in student loan and credit card debt and no college degree to show for
it. Found myself with no job, no place to call home, and no money in my back account

2012 Google AdSense shut down my account and lost my main source of income just two years after
starting my blog

2013 Hired freelancers who did not work out

2015 One mistake I made is taking too long to hire my first full-time employee. Up until 2015, I worked
with freelancers and contractors. Hiring full-time employees was a difficult decision because I
was scared to take on the liability and reviving my role as a manager

2015 Started Grocery Budget Makeover – a paid course on Penny Hoarder where users could learn
how to reduce their grocery budget. Invested 250+ hours and $20K. The course only brought in
$5K in revenue

2015 Signed a 5 year lease on a 3,000 square foot office. Outgrew the space and had to move less
than a year later. Still stuck with a $7,000/month bill

2016 Neglected email newsletter with 1M+ fans. Open rates fell from 40+% to 20% and we found
ourselves on the spam list for Hotmail

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Beyond every major success, you’ll find countless missed attempts, oversights and mistakes. What matters most, is how YOU choose to respond to it!

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“Many of life’s failures are people who did not realize how close they were to success when they gave up.” ~Thomas A. Edison
“You can’t have any successes unless you can accept failure.” ~George Cukor
“Failure is simply the opportunity to begin again, this time more intelligently.” ~Henry Ford
“Success consists of going from failure to failure without loss of enthusiasm.” ~Winston Churchill
“I am not discouraged, because every wrong attempt discarded is a step forward.” ~Thomas A. Edison
“Anyone who has never made a mistake has never tried anything new.” ~Albert Einstein
“The majority of men meet with failure because of their lack of persistence in creating new plans to take the place of those which fail.” ~Napoleon Hill
“In order to succeed you must fail, so that you know what not to do the next time.” ~Anthony D’Angelo
“My great concern is not whether you have failed, but whether you are content with your failure.” ~Abraham Lincoln
“I can accept failure, everyone fails at something. But I can’t accept not trying.” ~Michael Jordan
“I have not failed. I’ve just found 10,000 ways that won’t work.” ~Thomas Edison
“My reputation grows with every failure.” ~George Bernard Shaw
“You always pass failure on your way to success.” ~Mickey Rooney
“Failure is instructive. The person who really thinks learns quite as much from his failures as from his successes.” ~John Dewey
“Life’s real failure is when you do not realize how close you were to success when you gave up.” ~Anonymous
“I failed my way to success.” ~Thomas Edison
“The only real failure in life is one not learned from.” ~Anthony J. D’Angelo
“Failure doesn’t mean you are a failure… it just means you haven’t succeeded yet.” ~Robert Schuller
~“The better a man is, the more mistakes he will make, for the more new things he will try.” ~Peter Drucker
“The only time you mustn’t fail is the last time you try.” ~Charles F. Kettering
“There are two kinds of people in this world: those who want to get things done, and those who don’t want to make mistakes.” ~John Maxwell
“The greatest mistake you can make in life is to be continually fearing you will make one.” ~Elbert Hubbard