5 things managing political campaigns taught me about being a CEO

Kyle Taylor, founder and CEO of The Penny Hoarder
Kyle Taylor, founder and CEO of The Penny Hoarder

From Donald Trump to Kevin O'Leary, entrepreneurs entering the world of politics have been in the spotlight. And that has sparked a discussion about whether CEOs transition into successful political leaders.

My journey is the opposite: I went from politics to CEO.

In 2004, I began college as a political science major at the University of South Florida. During my freshman year, I campaigned for Working America. When the office closed after the November election, I moved on to Clean Water Action.

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The Penny Hoarder founder and CEO went from looking for change on the side of the street to millionaire status in six years

As my second semester rolled around in January, I was offered a promotion and an opportunity to work on a park bond campaign. In Texas.

My parents weren't thrilled that I was giving up my scholarship and dropping out of school. But I took the job and later worked on various campaigns in a number of roles for the next several years. And you know what? Working on campaigns taught me a lot about running a company.

Here are five things I learned from working on political campaigns:

1. How to sell

As a field canvasser, my job was to go door to door educating people on the issues and soliciting donations. I had a daily quota to hit, so I had to be direct when asking for money.

When the door opened, I had about a two-minute window to make a personal connection with someone. As a shy, introverted young guy, I was scared to talk to complete strangers.

The bad part: I'd have to talk to 40-60 people a day. The good part: I'd have to talk to 40-60 people a day. I had the chance to get better each time.

If I had an awkward exchange, I could tweak my approach with the next person who answered the door. I learned to overcome my nervousness and shaky knees by relying on my sense of humor — it's a disarming tool, sure, but it helped me relax, too! Plus, once I got someone to chuckle, I knew I had bought myself another 30 seconds.

I got better at reading people, relating to them and reframing my ask. I also assumed support — that the person on the other side of the door already cared about the issues and wanted to help.

It's never easy to ask people for money. But years of canvassing helped build my confidence when selling today.

2. How to build a business

On the campaign trail, I was never in the same spot for long. Working on the Affordable Care Act in 2009, for example, I began in Ohio, headed down to Virginia for a few weeks and then drove to Louisiana. My schedule hinged on the needs of the campaign and would change accordingly.

With each move to a new city came a new office. When I became a field director, I'd have to do everything from set up an office space to hire staff to navigate labor laws that varied from state to state. It was a lot of work in a short period of time — and an office might only last a couple months!

I didn't realize it at the time, but I was building mini-startups. Assembling and scaling a team quickly? These skills came in handy when I founded my own business and had to budget for an office, build a team, do payroll and administer benefits as a scrappy entrepreneur.

3. How to hire

There's an infinite need for canvassers during campaign season. I would routinely place ads on Craigslist, in newspapers and on job websites. I'd set up interviews for roughly half the respondents; from there, 50-60% would actually show up. After six years, I had conducted a lot of interviews.

During this time, I really learned what to look for and what questions were important to ask. Since these interviews were five to 10 minutes long, I had to quickly evaluate whether someone was a good fit. Two things I looked for were attitude and the ability to learn new skills. And today, those are still the first things I look for in candidates at The Penny Hoarder.

4. How to do press

I made my TV news debut at an event for Working America in Shreveport, Louisiana, in 2009. We organized an event at a bus depot with hundreds of people. Canvassers dressed up like doctors to disseminate information about the ACA and ask people to write letters to then-Sen. Mary Landrieu.

The event got national attention. As the organizer, it was my job — whether I wanted it to be or not — to speak to the press.

I gave my first on-camera quote during that campaign. I was the same introverted kid, but because I was passionate about the work, I was able to push that to the side.

I continue to do media spots as a CEO. Those earlier TV news segments helped me get comfortable in front of a camera and deliver a digestible message in a short period of time.

5. How to remain calm under pressure

Because of the hourly pay and atypical hours, canvassing jobs tend to attract college students. As a director, I had my fair share of expected issues, like people showing up late or not at all. I also experienced not-so-average problems, like neighbors calling the cops on my team, or canvassers getting sick, bitten by a dog or hit by a car. I was guaranteed to deal with some kind of situation every night.

It's easy to get overwhelmed when you're the boss. But after a while, I started to develop a mindset of "I've dealt with worse before." It's been a helpful reminder as I scale my business. (And thankfully, no one on my team's been hit by a car since.)

Kyle Taylor is the founder and CEO of The Penny Hoarder, one of the largest personal finance websites with 15 million-plus monthly readers. In 2016, the Inc. 5000 ranked The Penny Hoarder the 32nd fastest-growing private company and the №1 fastest-growing private media company in the United States. You can read his latest article here: "Here's Exactly What We Did to Improve Our SEO in 2016 … and Beyond."

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