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Jeff Klee: business leader showcase

By getting to know how business leaders tick, we can relate and learn from their experiences to make each of us better leaders ourselves. This interview with Jeff Klee, CEO of CheapAir.com is enlightening and a fun read.

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jeff klee chepair.com

jeff klee chepair.com

Tell us about yourself and your work.

A couple years ago my wife told me, half-jokingly, that she knows that my priorities are my work, the Dodgers, and her, in that order. I’d probably edit the rankings and add in my recently born daughter, but otherwise I’d agree that this list sums me up pretty well.

Essentially, I’m just a regular computer geek who has always had a fascination with flying. At CheapAir.com, I get to combine the two. I get oddly excited about the technical challenge of having to sort through hundreds of thousands of flight combinations that may exist for a trip, consider the 10-20 possible fares that might apply for each leg, and come up with a simple, clear, and relevant list of options to present to a traveler. (And to do it all within the 6 seconds that researchers say someone is willing to wait for their results.)

Walk us through a typical day in your life.

I try to wake up before my family, so I’ll usually get out of bed between 5:30 and 6:00 and go right to my computer. I spend about 30 minutes going through my inbox, writing replies, and checking the overnight site stats. Then I’ll go for an hour long run and come home to have breakfast with my wife and 11 month old daughter.

The hardest (but best) hour of my day is the next hour when my wife takes our dog to the park while I watch the baby. Sometimes it’s my only chance of the day to play with her and, as she gets bigger, that keeps getting better. It’s not easy, though, and by the time my wife gets back I’m always thoroughly beaten down and in awe of how she does what she does, which I know is much harder than what I do.

When I get to work, it’s usually with grand plans of all the things I am going to accomplish that day. But, once it starts, emails and conference calls and meetings tend to take over. A workaholic, I’ve historically stayed in the office until at least 7:00pm, sometimes much later, but ever since my daughter was born I have tried to leave earlier.

As soon as my family goes to sleep, though, I am right back on the computer. Late at night is the best time for me to get some “real work” done – a lot of the software development work that I’m still involved with – and I’ll work as long as I can, until I’m too tired to stay awake any longer.

What is your educational background?

I went to the University of Michigan for undergrad, and have a degree in economics.

Where were you raised? Where all have you lived?

I grew up in Los Angeles, left for 4 years to go to college in Michigan, and then came right back.

At age 15, what did you want to be when you grew up?

I’ve had the entrepreneur bug ever since I was very young. I always wanted to have my own business. As a kid, I was obsessed with making money and I went from one scheme to another, selling anything I could think to sell, like toys and candy to neighborhood kids or food to neighborhood construction workers. At 13 I created a laughably bad computer game for the Atari 800 which drew some interest from a software company. It wasn’t exactly a commercial hit, but it did make me a few hundred dollars.

By 15, I had turned my attention to scalping Dodger tickets and I actually did pretty well at that, thanks partly to Fernando Valenzuela and the fact that every game he pitched would be a sellout. So I never knew what exactly I wanted to do when I grew up, but I did know that I wanted to be in business.

If you could start over…

If you could start your current career over with everything you know today, what would you do differently?

I would take a different approach to building a team. I have an absolutely incredible group of colleagues right now who are smart, fun, hard-working, and very passionate, but getting to this point took longer than it needed to. In the early days of our company, we had a lot of luck hiring very young people right out of high school or college (or in some cases, still in high school) who were amazingly dedicated and capable.

Over time, many of them began to assume more and more responsibilities and, in fact, most are still with us in some sort of management capacity. There was a point in time where we were a decent sized travel company run completely by people (including myself and my business partners) who, not only had never worked in the travel industry before, but, in most cases, had never even had a real job!

I used to take great pride in the fact that everyone in our organization at every level (again including myself) had started at the very bottom and spent years working in the trenches, answering phones or processing tickets. I used to regularly say that, in hiring, all that matters is character. I truly believed that good people who are smart with integrity and a good work ethic can accomplish anything, even if they have no experience. I still believe that but I also think, in hindsight, there were times where we could have and should have gone outside our organization and brought in individuals with very specific skill sets and very specific experience that we just didn’t have within our group.

What is something unique that you do to balance work and life?

The question of balance has always been a tough one for me because I’ve never fully bought into the idea that work and life are separate. I have a hard time delineating between the two. I love what I do and my business is a huge part of who I am. My work life and personal life pretty much blend together and work is just another thing that makes life rewarding. I know I’m very lucky to be able to say that.

I’m a workaholic. I work more hours than anyone I know, but that’s OK, because I love what I do. I get up early and I stay up late and no matter where I am, I’m probably at least checking email. But it works both ways. I may work a lot of Saturdays and Sundays, but if there’s a midweek day game at Dodger Stadium I’ll be there more often than not. And when my daughter is old enough to have games, or dances, or anything else, I’ll be there, too. I may be at the computer after midnight many nights a week, but I’ll also be late to the office most mornings, so I can have breakfast with my family. Whether that is “balanced” or “unbalanced” doesn’t really matter to me, I’m not thinking in those terms.

What keeps you up at night?

My daughter. If only she’d start sleeping through the night!

More seriously, though, what makes me more anxious than anything is a country that’s losing its way. America used to be the place where big things were done and big problems were solved. Our parents and grandparents and great grandparents worked hard, made sacrifices, and did whatever needed to be done so that things could be easier for the next generation.

What’s happened to that spirit? Today, vision, ideals, and tenacity have given way to pettiness, apathy, and short-sightedness. I look at my daughter and I know that, barring a radical change, she is going to live in a country that is less hopeful, less inspired, and less a land of opportunity than the one I grew up in. Knowing that makes it really hard to sleep, sometimes.

If you could be someone else…

If you could spend one day in the life of another industry leader, who would it be? Why?

Sergey Brin of Google. First off, it sounds like he has a pretty cool life (with, apparently, a great office and a great plane). But more importantly he and Larry Page have accomplished a technical feat that still blows me away every time I use Google. As someone who has spent countless hours trying to shave off a second or two from our airfare searches, I understand how challenging it can be to quickly sort through massive amounts of data. Google has built something that is, by orders of magnitude, so much better than what anyone else has done, that most people takes it for granted. It may take 6 seconds to search for a flight to New York, or a few seconds to search the iTunes store, or sometimes up to 10 seconds just to move from one page to another on a lot of web sites. But Google will find virtually any piece of information in the world in less than a second, usually responding with what you need before you can even finishing typing it! I know there are many who are suspicious of Google, but I am perpetually in awe of them.

What tools can you not live without?

For a computer geek, I’m surprisingly not that interested in gadgets. That is, as long as I have access to the internet at all times. I saw a clip of a comedian a few weeks ago doing a bit about being on a plane with in-flight WiFi where the internet connection stopped working. The guy sitting next to him got furious and the comedian joked that it’s shocking how quickly people come to think that the world owes them cheap, unfettered, uninterrupted access to even the most complicated and amazing technologies. For that, I’m as guilty as his seat mate.

I know that the internet is a technical miracle, the way it brings every bit of information in the world to people in every corner of the earth. But if for one minute there is a glitch and that amazing technology gets a little slow, I’m the first to declare what an outrage it is. I can live without most tools, but if I’m anywhere without a high speed internet connection, I get anxious.

What about you would most not believe unless they knew you?

I don’t eat condiments. Ketchup, mustard, mayo, I hate them all. I have spent countless hours debating the merits of a plain Dodger Dog versus one loaded with everything but, so far, it’s been a losing battle. My wife constantly complains that our 11th month old has a more mature palette than I do.

What inspirational quote has stuck with you the longest?

“The only way out is in.” I don’t know where it came from but it was said to me by a mentor of mine many years ago. Bad things happen in business and in life. Some bad breaks are not your fault and couldn’t have been foreseen. But often it doesn’t really matter why something happened, who’s to blame, or who “should” be responsible for fixing it. I have learned that if something is really important, I need to take ownership of it, put my head down, and just get it done. That doesn’t mean I have to do everything myself; I have a great team that I am lucky enough to be able to rely on. But it does mean taking ultimate responsibility for the situation and the outcome.

The American Genius is news, insights, tools, and inspiration for business owners and professionals. AG condenses information on technology, business, social media, startups, economics and more, so you don’t have to.

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Business Entrepreneur

How to turn your side hustle or hobby into a successful business

(BUSINESS ENTREPRENEUR) Surely you have a favorite hobby by now, well what can you do with it? You can grow it into a full time business, but how?

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Almost everyone has a hobby they enjoy doing in their spare time — something that sparks their creativity and engages their senses. If you look forward to your weekend pastime more than your nine-to-five job, perhaps it’s time to turn your passion into profits.

This path requires dedication and commitment. However, as you turn your hobby into a profitable reality, the hard work pays off. Getting to that point requires several steps. Thankfully, there are many resources out there that will help you pave the way.

  1. Establish the Basics: Establishing the basics will act as your roadmap for turning your passion into a business. This plan will no doubt change along the way, but it’s important to have preliminary ideas of where you want to take your enterprise.First, establish what you’ll be selling. Most hobbies can become a business, but you’ll need to hone in on what people will be buying. Anything of value — like products and services — can be an enterprise. Once you have that in mind, you can decide if you want it to be a part-time or full-time job. If you already have a job, managing your time between the two can get tricky.

    To stay on top of your tasks, you can look into a time management app or software. With these platforms, you can input how much time you spend on certain projects. From there, you can properly divide your time and give your new business the attention it requires.

    Next, you’ll have to conduct research. Is there a market for your product nearby? Can your business realistically take off in your location? How much needs to be e-commerce? Market research can help you determine who’s interested in buying and what you’ll need to get your business off the ground.

  2. Know Your Finances: Your finances are one of the biggest factors when starting a business. Too often, people rush into things without planning their expenses and resources first. Be sure to ground your plan with actionable steps. For instance, If you’ll be working from home, you can save on renting costs. However, some businesses require a storefront, so keep that in mind.You can also look into financial planning software or budgeting tools. Research relevant tips for budgeting when starting a small business. One pro-tip to keep in mind, if renting, is that you’ll want to save around six months’ worth of rent beforehand. That way, when you get started, you won’t rely on revenue to pay this expense.

    Additionally, don’t forget about taxes. You’ll likely need to pay estimated quarterly ones and potential sales taxes, too. There are multiple tools to help calculate these expenses online. Don’t be surprised by the costs, a hobby can be inexpensive but ramping up to a business can be costly, but worth it.

  3. Take the First Steps: As you form your plans and goals, you can start to take the first steps toward a sale. This phase consists of setting up space in your home or a store and developing your products or services.You’ll also want to set up a digital platform where you can access information at any time. In this central base, you can refer to all the details about your plans, finances and marketing strategies. With tools like Google Docs and Spreadsheets, creating accounting documents and client lists become easy.
  4. Create Marketing Strategies: Your first sale will likely be to someone you know. That’s an important step. No matter who it is, though, marketing and advertising can take your business to the next level. Make sure you have a strong online presence. With social media and Google’s resources, you can increase your reach.Having social media pages on multiple platforms can help spread awareness of your business. You can use hashtags and locations to establish yourself so others can find you. Most of these platforms have analytic tracking, too, so you can see who engages with your pages and when.

    From there, you can work with Google Analytics. It connects to your website and tracks activity and sales. It shows you which visitors come from social media, referrals and search engines. Then, you can focus your marketing strategies on strengthening those areas.

    Additionally, it’s vital to focus on search engine optimization (SEO). SEO works with search engines like Google to push your listing to the top with keywords and links. As you cover your bases with SEO and social media, your online presence can grow along with your sales.

  5. Network: Outside of the online world, you have options for growing your business, too. Local companies can work together to help each other succeed — you can look into other small businesses in your area for new opportunities. People often overlook the power of collaboration, but it can bring about significant results.If you can provide a service or product to local businesses, they may be able to advertise for you at their locations. For instance, if you’re a florist and provide arrangements for a local coffee shop, it could put your business cards next to your display. Customers will see your information and know they have a local option should they need flowers.

    You can also bring this connection to the digital realm. When you interact with other businesses on social media, people will see that engagement and click on your pages. That dynamic could translate to more traffic and sales. Check online to find the communities of your chosen hobby, the people there can fill you in on vital info that may be missing, or be a customer base you can connect w

  6. Keep the Growth Going: The last step is to perpetually keep your business growing. In this phase, you can quit your full-time job or reduce your hours to be a part-time employee. You can then focus on your new enterprise.You should expand your outreach through email newsletters, deals and coupons. You can give rewards to loyal or returning customers if you’d like, too. You can also add a blog or a section for customer service and inquiries to your website. Once your business grows enough, you may need to hire help.
    As you progress, adjust your goals. You’ll see that your trajectory differs from your original ideas, but you can keep building to take it to the next step. Set new milestones and watch your business thrive.

When a Hobby Becomes a Business

You should be aware that this a long-term process. Building a brand won’t happen overnight, but the small changes will add up until your company is a force in the market. It’s also an ongoing activity. The more you grow your enterprise, the more possibilities open up. It all starts with your hobby and your entrepreneurial spirit, which can take you anywhere.

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Business Entrepreneur

You should say no to one-way video interviews

(BUSINESS ENTREPRENEUR) Recruiters, please stop asking job applicants to send in one-way video interviews — they are demoralizing and could be discriminatory.

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Woman in video interviews and making a confused hand gesture.

It’s hard enough out there for job seekers, but now some companies are requesting one-way video interviews from candidates. This is problematic on several levels. Unless the job is specifically “making TikTok or Reels videos of yourself,” HR departments should not ask this of job candidates. Even if that is the precise job description, a portfolio would be enough to show that an applicant can do the required work well.This format is also ripe for discrimination, as the recruiter can make assumptions and decisions due to their implicit bias more easily over a disembodied video than for a flesh-and-blood interviewee.

For starters, job hunting and interviewing are two stressful activities for most people. Especially post-pandemic, when it’s more likely than ever that candidates have been unemployed or underemployed for too long already, the pressure people feel about finding a job is intense. Interviewing makes most people nervous to begin with. Being on camera makes a lot of people even more nervous. One-way video interviews are not unlike public speaking, something an estimated 75% of people have a phobia of public speaking to some degree, according to various publications. Add to that the discomfort many people have seeing themselves on camera, and one-way interviews seem not only rude, but also cruel.

One benefit to one-on-one interviews, either by phone call, Zoom, or in person, is that the interviewer and the candidate have the opportunity to interact in a more authentic, conversational way. This can help put the candidate at ease, or at least will give them an opportunity to ask the HR recruiter questions about the role and the company. It also gives the interviewer a better feel for the candidate and how they would fit into a company culture or team. There is an exchange of energy for better or worse. Face-to-face, or person-to-person interviews show candidates that you value their time as well as your own. One-way video interviews are one sided, indicating that only the recruiter’s time is valuable or worth being valued.

Many job candidates have likely already applied for several positions. Updating and sending out a resume and portfolio, filling out an online application form, and possibly crafting a cover letter should be enough to convey a candidate’s qualifications to move on to an interview. Many of those documents are lost in the ether, as many recruiters and HR teams do not reply to all applicants. One-way video interviews seem impersonal at best. As with the resumes and applications, there is also the possibility that nobody will watch it, that nobody will reply. How soul-crushing. To add insult to injury, the process for these seems wildly inconsistent from company to company, with some telling the candidates to make it as long as possible. Other companies provide automated, popup questions at timed intervals, either cutting the candidate’s previous answer short or leaving them with dead air time waiting for the next question. Excruciating—surely not an opportunity to shine.

The thought of someone putting themselves through a process that could be so grueling for them personally only to hear crickets in response is simply depressing. It’s possible that a real live human won’t even see these, because if an HR recruiter doesn’t have the time to schedule a phone screener at least, they likely won’t be taking the time to watch all of the one-way video interviews they receive. This shows so little regard for the applicant that it reflects poorly on the company—and tells applicants something about how the company will likely treat their employees.

If Reddit r/recruitinghell and members of the Austin Digital Jobs Facebook group are to be believed, a lot of candidates won’t bother with these awkward and dehumanizing one-way video interviews anyway. In a popular Reddit post, hundreds of commenters weighed in to agree with u/tron_mexico25’s post saying he turned down a request to do one of these. The Reddit post concludes, “If you would like for candidates to pursue your open roles, I would humbly suggest someone reaches out with a more personal touch instead of asking candidates to speak into a camera with no opportunity for meaningful interaction.”

Both HR recruiters and candidates in Austin Digital Jobs responded to the posting of a CareerPlug article, written by their Director of HR, Natalie Morgan, that they should be avoided and “are hurting the candidate experience.”

The ADJ members strongly agreed with Morgan that these one-way videos were disrespectful, “gross,” “terrible,” “indefensibly dumb,” and a waste of time. One ADJ member, Annette Priest, sums up the whole vibe perfectly, when they say, “Yuck. You’re almost never treated as well working for a company as you are when you’re interviewing. Consider this a red flag and run away!” I agree completely. Applicants, you shouldn’t subject yourself to these. Recruiters, please be better.

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Business Entrepreneur

You’re more likely to thrive with entrepreneurs if you get distracted easily

(ENTREPRENEUR) If monotony and boredom at work bores you, it’s possible you may fit with the other entrepreneurs with a quick and constantly changing career.

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When Bill Gates was a kid, he knew he liked messing around with code. He couldn’t have known how it might evolve, but he, like other entrepreneurs, was willing to live in the distraction, focusing on details when needed, but always learning, moving on, taking risks and growing in the process.

Some of the most successful folks among us are not content to sit and make widgets every day. They cannot thrive in a detail and focused work environment. So, it may come as no surprise to know that people who are more easily distracted are also more likely to thrive as entrepreneurs.

According to this study, if you are intelligent and get distracted more easily, those two qualities combined will likely enhance your creativity. And, that creativity and ability to use distraction as an advantage can be channeled to create new things, jobs, companies, etc.

For those of us who are more easily distracted, who enjoy doing different things every day, and who like learning, a recent article in the Harvard Business Review suggests a good option is to find a career path that provides the right amount of distraction and which is a great fit for your personality. If you do that your talent is more likely to be apparent because you are playing to your strengths. Also, if you are working in your sweet spot you will be more productive and motivated.

Maybe not surprisingly, the top job for those who live in distraction is entrepreneur. The term “easily distracted” often comes with a negative connotation, but considering an entrepreneur is taking risks, making things happen and creating companies, ideas, products that may have never existed, this spins that idea on its head. Entrepreneurs are the chief cooks and bottle washers of the world. They ideate, create, hire and inspire. None of that is possible in a monotonous work environment.

“Unsurprisingly, meta-analyses indicate that entrepreneurs tend to have higher levels of ‘openness to experience,’ so they differ from managers and leaders in that they are more curious, interested in variety and novelty, and are more prone to boredom — as well as less likely to tolerate routine and predictability,” according to the HBR story.

Other careers that are great fits for those of us (me included) who enjoy distraction are PR/Media Production, Journalism and Consultant. What these fields all have in common is, there is never a dull moment, switching from task to task is pretty commonplace, and you will do well if you can be a generalist – synthesizing information and weeding out the unnecessary.

Not sure where your strengths lie? Here’s a quick quiz to give you some feedback on how curious you really are.

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