How This Entrepreneur Went From Poverty To CEO Of A Dead Sexy Startup

image001A version of this article previously appeared on Forbes.

Don Charlton’s heroic journey began with him growing up on government assistance and culminated in his  founding The Resumator, one of America’s fastest growing startups. Don’s perseverance and chronically positive attitude is  inspiring.

The Resumator’s intuitive recruiting and applicant tracking solution has been used by over 12,000 companies, which have processed more than 4 million resumes and filled 36,000 jobs. The company’s clients include: Pinterest, Instagram, Tumblr, Hootsuite, Klout, Posterous, Bitly and Mashable. 

You can hear Don tell his story in the following excerpt from his recent talk at UC Santa Barbara. Note: I am a Board Member and an investor in The Resumator via Rincon Venture Partners.


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Don began by explaining that his impoverished childhood drove him to a life as an entrepreneur.“… I grew up ridiculously poor. To give you an idea how poor, our kitchen table had three legs. We pushed it in a corner to keep it up. My mother suffered from a mental illness that was undiagnosed her entire life, and we didn’t find it out until after actually she passed away. (My childhood poverty) was something that I hid from the world until I got to the point that I felt like I had succeeded enough that I could wear it as a badge of honor… (because) it reminds me of the perseverance it takes in order for you to achieve anything in life.”

Don recalls the childhood moment when he decided he would control his own destiny. “Growing up… I had never thought about being an entrepreneur. I didn’t think about going to college either. I just thought about wanting to have food every single day. I wanted to be able to eat and I knew that required hard work.

I remember the day when I knew that I wanted to control my own destiny…I was really, really hungry. I wanted a Little Debbie snack cake, which I think they’re still $0.25… and I remember having $0.15.I remember digging through my mom’s purse, looking underneath the refrigerator… looking in the couch. And I could not find a stupid dime. One dime. And I remember it was the summertime, and I was walking outside. And I was hungry, I was tired. And I remember leaning back and lookin’ up at the sun. And realizing that here I was… ten years old… I just wanted a dime. That dime might as well have been 1,000 miles away from me because I could not manifest a dime in my life. Right then and there I saw the importance of taking charge of your own life.”

High School Guidance

Don was fortunate that a high school guidance counselor took an interest in his future and steered him toward a career in computer graphics. “I was the best artist in every school that I was in. I love to draw. Whenever I was really, really young, we couldn’t afford paper, so I’d open up the cereal boxes… and I would draw food. I would draw Snickers bars, I would draw Kit Kats and so forth. I was a senior in high school and, at that point, I still wanted to basically be a cartoonist.

I had a great guidance counselor. Everybody kind of knew our home situation. I’ll never forget his name, it was Mr.Gillespie. He pulled me into his office and he said, ‘Don look. You’re not gonna make any money drawing. There’s this thing called graphic design. It’s commercial art… you draw things on the computer. You really should do that.’

 Now one of those words in his statement… really stood out, ‘computer.’ I had this dirty little secret that I didn’t tell anybody. Every morning in homeroom I snuck to the library to computer program. Every free moment I had. I almost stopped drawing. I almost stopped being an artist. I would sneak to the library to computer program.”

After graduating from college, Don began his career at a small design firm.

“So I worked at a great design firm called, Agnew Moyer Smith and there’s two great guys there. Reed Agnew and Don Moyer really did shape the person who I am today. They brought me in and they said, ‘There’s this whole new thing that we think there’s a lot of business, it’s the web. If you want a job here you’re going to have to design websites.’

I said I want to keep my job so I’m going to figure it out. And that’s where I fell back in love with computer programming. Suddenly I was given this opportunity to computer program again… and I fell back in love with that. My advice to you is to find somebody who is willing to trust you very early on.

So I started rebelling and I started designing more and more and then my boss is coming at me and saying, ‘Well wait a minute, why do you have so much done when you haven’t actually talked to me?’ And I said, ‘give me the opportunity to fail.’ My bosses saw that I wanted the opportunity to fail and they gave me that opportunity. They put me in front of companies like McDonald’s, Steelcase (and) Caterpillar; where I was presenting to senior vice presidents. So I was this really poor kid from the projects, with tons of self-consciousness and they took all of that out of me by forcing me into positions where I had to basically grow up, become a professional, learn how to present (and) not be afraid to… command a room.”

Don’s First Failure

Although he was excelling as a web designer, Don began to get the itch to start his own business. However, in retrospect, he admits that he lacked the requisite experience and self-awareness. “So now at this point, I’ve got ten years of business experience, so I have a little bit of a swagger, I think that I know everything. Again, here I am… 27, thinking I know everything. I’m gonna go off, I’m just gonna start a business.

My ears were closed so I decided I was going to, try to start a company…at night…(and build)a content management system. We basically just fizzled through the money that we had. That company failed.”

Don’s Aborted Second Act

Rather than give up after his first startup failed, Don learned from his mistakes and immediately launched venture number two, which eventually morphed into The Resumator. “I had this determination in me that I was gonna try to make a business. I was gonna try to be successful, so I pivoted immediately. I thought about hiring, and I thought about whenever I was hiring designers at my old design firm, I hated hiring because I had a full time job.

So… I ate a piece of humble pie… (and) I started ingesting information about how to run a technology startup. So, you guys are fortunate that you have tons of history. I promise you, if you watch the TechCrunch 40 demos… if you go to sites like Mixergy and you start to hear the stories of entrepreneurs (you will avoid common startup mistakes). 

I was fortunate whenever John invested in me, he flew me to Santa Barbara the other time I was down here (and) I met Kevin O’Conner, Founder of DoubleClick. I remembered listening to Kevin O’Connor’s story long before I ever met him so I was kinda feeling I was in like kind of a startup entrepreneur rock star scene whenever I met him.

If you want to do something you need to start ingesting information about it. You need to start hearing (startup) stories. You’re not too young to have a subscription to Inc. Magazine or Forbes Magazines. Because it’s not just, there’s tips in there about how to basically grow skills that you don’t have yet.

Put on your headset and don’t listen to music, listen to an entrepreneur talk about their journey. That’s how you can really start to learn a lot about basically building a business and that’s what I did while I was coding Resumator. 

The next thing is I educated myself on how to get into… the start-up world, networking. If you guys want to work at an early stage start-up, early stage company, you gotta basically start to hang out with people who are in that world. 

Building your personal network right now is going to be one of the most important things that you can do. The more time you spend on Facebook as a senior, the more likely you are going to be stunting your ability to network in the future.”

Don Gets Punked

As Don came close to launching his second venture, he decided to join an existing startup at the 11th hour. “I punked out. I quit my job… and then I got a great job offer from another company. I took a job at Grasshopper… but it stunted the growth of Resumator because suddenly I was focusing on all of these tasks inside of Grasshopper and I wasn’t focused on building Resumator or growing as an entrepreneur.”

Fortunately, after a brief stent establishing Grasshopper’s elegant and effective web presence, Don decided to take his second entrepreneurial leap. He left Grasshopper and formally launched The Resumator. The company has been extremely successful. As Don humbly points out, “We had both presidential campaigns using our platform (and) some of the hottest growing startups. (Yet) we have an audience of 600,000 businesses but we only have a couple thousand of them.”

Words vs. Actions vs. Accomplishments

Don finished his talk by explaining the stages entrepreneurs should go through when launching their ventures: words and actions, followed by accomplishments. In Don’s words, “If you’re trying to start a company, you’re going out and you’re telling people what you’re working on. They see you’re working on your code, you’re showing them demos. With my company, we had actions. We started gaining momentum, people were seeing that we were building a really great piece of software. But where you really start to gain momentum… is when you have accomplishments.” As Don makes clear, without accomplishments, words and actions are meaningless.

Follow my startup-oriented Twitter feed here: @Johngreathouse. I promise I will never tweet about walks on the beach or that killer burrito I just ate.

John Greathouse

John Greathouse is a Partner at Rincon Venture Partners, a venture capital firm investing in early stage, web-based businesses. Previously, John co-founded RevUpNet, a performance-based online marketing agency sold to Coull. During the prior twenty years, he held senior executive positions with several successful startups, spearheading transactions that generated more than $350 million of shareholder value, including an IPO and a multi-hundred-million-dollar acquisition.

John is a CPA and holds an M.B.A. from the Wharton School. He is a member of the University of California at Santa Barbara’s Faculty where he teaches several entrepreneurial courses.

Note: All of my advice in this blog is that of a layman. I am not a lawyer and I never played one on TV. You should always assess the veracity of any third-party advice that might have far-reaching implications (be it legal, accounting, personnel, tax or otherwise) with your trusted professional of choice.

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