RESUME OF FAILURES
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 ThePennyHoarder.com.
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