My Worst Interview Ever

Every single morning, my grandpa would get up and begin cutting up grapefruit for he and my grandma. She would make oatmeal on the stove, and he would meticulously pick out the seeds and delicately slice each and every triangle-shaped piece. Once the food was ready, they would sit down, eat, and grandpa would pull out the morning paper and do the crossword puzzle.

While I enjoyed the breakfast, I was fascinated by the puzzles. Only being in elementary school at the time, I couldn't help much...but I tried. And today I'm still trying. I love crosswords...thanks entirely to my grandpa's love for them. (As an aside, I really love grapefruit too!)

Anyway, our guest today has a pretty incredible job. In addition to being a podcaster, Emily Prokop is a crossword and word search puzzle editor. Her career (puzzles) not only impacts her hobby (podcasting), but it changed her entire life.

Emily Prokop is a trivia lover and puzzle editor, in addition to being a wife and mom and podcaster. Her latest podcast is called "The Story Behind", which examines "the extraordinary history of the ordinary."

SHOW NOTES:

0:51 - Emily edits crossword puzzles and word searches for a living, and you won't believe what name she has to edit out of old puzzles these days!

2:42 - "The Story Behind" is the name of Emily's podcast, and is SUPER fascinating.

4:03 - An interview where the interviewer couldn't quite ask a succinct question not only confused Emily, but ended up being her worst ever.

6:50 - How do you interview someone in such a way that allows their answers to tell a story?

8:17 - Try a free 30-day trial of RINGR today!

8:51 - The art of silence. It's amazing what a pause will do to elicit more information from your guest.

10:52 - Emily's first journalism course in college not only changed her career, it introduced her to her husband!

13:03 - Find Emily on Twitter and be sure to check out her podcast "The Story Behind."

13:37 - What is Emily's favorite piece of trivia these days?

There are certain people you meet in this life who always seem to be doing something. Not talking about it. Not planning for it. Actually doing it.

In the podcasting space, Chris Krimitsos is one of those people. From leading an industry conference to producing a ground-breaking documentary about the space, Chris is neck-deep in the podcasting world. And he makes it seem like business as usual. But the story of how he got there? It's anything but usual.

Chris Krimitsos is the Chief Creative Officer for the Podfest Multimedia Expo, which attracts hundreds of podcasters from around the world each year. He is also a filmmaker, currently producing "The Messengers: A Podcast Documentary" which is set to release later this month.

SHOW NOTES:

0:56 - Chris and his team are working on a podcast documentary called "The Messengers."

2:11 - A guest showed up for a live interview in front of an audience not dressed for an audience.

4:58 - Chris used to host a TV show too...and that is WAY more difficult than it sounds.

6:58 - Tim and Chris are using RINGR to record this interview. Check RINGR out for free here.

8:19 - Six months off--and a move from New York to Florida--changed Chris' life forever.

10:15 - A chance meeting at a random dinner party opened the door for Chris to get into media...and never look back.

13:43 - Learn more about Podfest or email Chris directly at [email protected].

In late 1988, my dad began looking for a new job. It wasn't the he didn't like his job as a high school teacher and counselor, but since he also was involved with the music at our church and as a marriage and family counselor at a private practice, he was stretched thin.

I was in 5th grade at the time, but I remember him saying that he was searching for a job that combined all the things he loved about his current jobs (music and counseling and teaching), but in one job. That's why, in the Summer of 1989, we moved to Illinois so he could become a pastor and worship leader. In most every way, it was a perfect fit.

Talking to Joe Saul-Sehy about his worst interview ever, I thought about my dad. Over the years, Joe realized that there had to be a way to do all the stuff he loved and very little of the stuff he didn't...all in one job. And, today, it's clear Joe was right.

Joe Saul-Sehy is a former financial advisor (for 16 years) and represented American Express and Ameriprise in the media. He's now the host of the award-winning "Stacking Benjamins" podcast which has been recognized recently by Kiplinger, Entrepreneur, and US News and World Report as one of the top podcasts about finance.

Show Notes:

1:06 - The long road to "overnight success."

1:53 - Joe is giving advice already. (He's good like that.)

3:38 - A Harvard professor was Joe's worst interview...but it wasn't exactly the professor's fault.

6:39 - Joe recommends a book called "Out On the Wire."

7:51 - Try out RINGR free for 30-days.

8:21 - How did Joe get where he is today...and what else (if anything) would he be doing if not podcasting?

10:35 - A letter from a mentor changed Joe's life forever, making him realize that there truly were "other mountains to climb" other than working in finance.

12:53 - Like his mentor did years ago, what would Joe put in a letter to others today to encourage them to chase their dreams?

14:30 - Check out the "Stacking Benjamins" podcast.

Shortly after my family moved to Illinois, I remember my dad mentioning that "the new guy on the radio" had started going to our church. His name was Doug Hannah. In Jr. High at the time (early 90's), I had no interest in radio as a career yet...but I could still tell that this guy was going places. And a few years later, he did. To Chicago. And then Houston. And then Nashville.

A decade later--and in radio myself--Doug called and offered me a job, giving us the chance to work together at WAY-FM for a few years. Now it's been another decade (or more), and I'm honored that Doug agreed to be on the show. If you had told me 25 years ago that "the new guy on the radio" would one day be on my podcast, I would have said "no way." Also, I would have said, "What's a podcast?"

Doug Hannah is a long-time radio veteran who is currently heard on Sirius/XM Satellite Radio's "The Message." He is also a well-respected voice talent for companies including TNT, O'Charley's and Steak N Shake. Doug also hates the new iPad Pro, has a serious addiction to Diet Pepsi, and is a relatively new grandpa.

Show Notes:

0:39 - Another "offended" guest by the title of the show. :-)

1:26 - Does Doug get products in exchange for doing voiceover work?

3:16 - Was Tim really Doug's worst interview ever?

3:37 - The real worst interview used to be on "Saved By the Bell." And it wasn't Screetch.

5:40 - Is there a way to save an interview where the guest is 100% checked out?

8:17 - Doug and Tim are connected on (and recorded by) RINGR. Free 30-day trial here.

9:07 - Could Doug have joined the pro bowling tour if radio hadn't worked out?

10:30 - Moving in with your in-laws after losing a job? Yep. Doug did it. And it changed his life.

12:31 - Connect with Doug on his very own website or on Twitter.

Some people find it extremely hard to focus. I know this because 1) it's fairly common knowledge and 2) I'm one of them. (Hey look, a duck!) Todd Uterstaedt, however, is not one of those people.

As you'll hear, Todd is laser-focused on a very specific audience, and he does it both well and unapologetically. Todd doesn't talk to startup founders. He doesn't talk to CEOs. He only sits down with current CEOs who founded the company and had to make the transition from creating a company to maintaining and growing it.

But, today, he sits down with us...and shares his worst interview ever.

Todd Uterstaedt is a CEO coach and the host of the "From Founder to CEO" podcast...as well as a former military intelligence officer. Todd has interviewed well over 150 CEO's on his show (from small companies to large publicly-traded ones) based in Cincinnati, Ohio.

SHOW NOTES:

0:44 - Is Todd a prima donna?

2:23 - Todd's worst interview ever was with a "big catch" guest...and involved the s-word. ("Skype.")

7:01 - Thankfully, Tim and Todd connected and recorded using RINGR.

7:42 - How do you get the information you want out of the people you interview?

10:05 - A late night with the US military in South Korea changed Todd's life forever.

13:29 - You can find Todd and From Founder to CEO here.

Before "My Worst Interview Ever" began, I put a list of people together who were "dream guests." Essentially, they were leaders in the industry who I didn't expect to get on the show, but I sure hoped to. Each had to fulfill all of the following requirements:

• A thought leader in the business, entrepreneurship, podcast and/or broadcast spaces
• Having done (or been a guest on) a ton of interviews
• Have a great/painful "worst interview" story to share
• Lead a passionate tribe of people who would naturally benefit from hearing their interview story

Chris fit all of those perfectly. And, miraculously, he agreed to be on the podcast. As he mentions in the interview, he does his best to serve others through his life and his business. And today he served us very well, indeed.

For most, Chris Brogan really needs no introduction. Put simply, Chris helps people and companies use media and community to attract customers. He's an author, a speaker, a blogger, and business owner…and has a ton of free, helpful resources on his website ChrisBrogan.com.

SHOW NOTES:

0:52 - Chris wants to interview Matthew McConaughey (and has a plan to lure him)

1:29 - Learn more about Owner Media, which Chris runs.

4:41 - We get an interviewing tip before the actual story...because, Chris Brogan.

5:42 - Chris decided to have a little fun with a guy who was interviewing him.

7:53 - In an attempt to ruin the interview, Chris gave some really ummmm...awkward responses to questions.

9:17 - Tim tries to get a takeaway or two...and Chris has some great ones.

10:55 - Tim and Chris are connected on RINGR, with Chris on his smartphone! You can get a 30-day free trial right now.

11:17 - What was the moment in time that changed Chris Brogan forever?

14:03 - Connect with Chris online at either his personal website or his business website. And don't forget to sign up for his newsletter!

Many years ago (though not too many, 'cuz she is super young), Elsie Escobar and her family emigrated to the United States from El Salvador. As you might imagine, it changed her life. Not only was she in a new country with a new language and new customs...but she was presented with new opportunities that simply didn't exist in her home country.

To say Elsie has made the most of those opportunities would be a massive understatement. She turned her love for yoga into a podcast and that podcast into a career. Today, Elsie is a leader in an industry that is seeing explosive growth...partly due to the trail she blazed all the way from El Salvador.

Elsie Escobar does a little bit of everything. She works as a community manager for Libsyn, hosts her own podcasts—including "She Podcasts" (a podcast about podcasting from the female perspective and FOR women)—and also teaches yoga…which, ironically, is what first got her into the podcasting space to begin with.

SHOW NOTES:

1:32 - Elsie has a lot of podcasts. And is very bendy.

4:00 - A live event (and a very dull guest) set the stage for Elsie's worst interview ever.

7:37 - How do you decide between bailing on an interview and pushing forward? When is it worth it?

9:19 - This entire episode was recorded on RINGR. Tim in his studio. Elsie on her phone!

10:05 - As a little girl, Elsie and her family came to the United States from El Salvador. Learn how that changed her as a person and as a podcaster.

13:51 - Elsie loves her some Twitter. Check her out @yogeek, @shepodcasts, and her employer @libsyn.

In early 2015, mere months after starting RINGR, I moved to Cincinnati, Ohio for six months to join a business accelerator called OCEAN. Being somewhat new to the podcast industry, I had heard Cliff Ravenscraft's name...but I didn't fully grasp how influential he was, nor did I realize that he lived about 10 miles from Cincinnati. However, I quickly learned about both and proceeded to send Cliff a completely unsolicited and unabashedly selfish email.

Long story short, the guy known as "The Podcast Answerman" miraculously agreed to meet with me to talk podcasting and check out RINGR. We chatted for about an hour at a Chipotle in Northern Kentucky after Cliff's daily workout. He was gracious--especially considering we had a few difficulties with the RINGR beta--but while leaving, I felt sure I had completely wasted The Answerman's time.

Perhaps I did. But Cliff, dripping with graciousness and sporting a stunning new physique, still agreed to be on the podcast today. He was fantastic. And now I have a hankering for some Chipotle.

Cliff Ravenscraft is probably better known as "The Podcast Answerman." He started podcasting back in 2005 about the TV show "Lost" and has turned the hobby into a very full-time career. In addition to hosting several podcasts himself, Cliff speaks regularly at podcasting conferences across the country and has committed to working out six days a week for the rest of his life!

SHOW NOTES:

1:45 - Cliff turned $35 into a podcasting career...and is now more than 3,700 episodes in!

2:32 - The Podcast Answerman didn't quite have all the right answers during his worst interview ever.

7:29 - What should Cliff have done during this disaster to help avoid the problems?

8:40 - Get more info on RINGR (how Tim and Cliff recorded this).

9:18 - What was Cliff doing before he started podcasting? How did he make the switch?

11:38 - The moment that changed Cliff's life involved the distinct potential of disappointing his dad.

12:47 - Hear the episode Cliff referenced that tells the full story behind leaving his job to start podcasting.

15:02 - If you're thinking about starting your own podcast, make sure to sign up for Cliff's newsletter.

Several years ago I emceed a fundraising event that was being headlined by a well-known, well-respected public speaker. Since we were both seated at the head table, I had the chance to chat with him for a bit during dinner. To say I was surprised (and disappointed) by his demeanor would be a gross understatement.

From stage, this man was articulate, passionate, and a pillar of kindness and grace and selflessness. In person, um...not so much. As best I could tell, this man played a role when he got behind a microphone. One-on-one he was disinterested, short, and rude. In front of a crowd, he was...pretty perfect. Though not a politician, he certainly could have filled those shoes rather nicely.

Unfortunately, I think it's fairly common for public figures (and maybe all of us) to have two personalities. Which is why it's so stinking remarkable when you come across someone who is genuinely authentic, no matter what is happening or who is watching. Lisa Williams is one of those people.

I knew of Lisa long before I actually knew her. She was the radio star at that big station in Orlando...and then at that big network in California. Then, one day, she became my morning show consultant. And then my friend. And I can tell you--beyond a shadow of a doubt--Lisa is as real as they come. Her heart is always on her sleeve. And always in her voice.

Lisa Williams has been on the radio for the past 26 years, and is currently the host of the nationally syndicated radio show (and podcast) "Life with Lisa Williams"…heard on 62 stations around the country. During her career, Lisa also spent time on the K-Love radio network and Z88 in Orlando and as an on-air talent consultant.

SHOW NOTES:

0:32 - Lisa is happy to learn she is NOT our token female.

1:29 - How Lisa's podcast kinda-sorta turned into a nationally-syndicated radio show.

2:47 - It was in the early 1990's when Lisa had her (very long) worst interview ever.

8:05 - What did Lisa learn from that interview and how would she deal with it now?

10:20 - Lisa loves RINGR. You can try it for free here.

11:08 - Lisa almost didn't graduate from high school. Hear how a teacher--in 30 seconds--turned Lisa's life around.

14:14 - You can find Lisa on the web here...and you can learn more about the sponsor of her show, Cure International, here.

There is no shortage of inspiring quotes about dealing with setbacks in life:

• "Make lemonade out of lemons."
• "It's not how many times you get knocked down, but how many times you get back up again."
• "Losers quit when they fail. Winners fail until they succeed."
• "When a door is closed, a window is opened."

And I could list hundreds more...

But far more powerful than any quote is the story of someone who has actually proven these proverbs to be true. Someone who has squeezed every last drop of juice out of the lemon they were handed and produced a tall, cold, sweet glass of lemonade.

Todd Cochrane is such a person. After a swimming accident put him in the hospital for several weeks, Todd made a career decision that not only changed his life...it landed him in the Hall of Fame.

Todd Cochrane is a published author, speaker, and the CEO of Raw Voice and Blubrry…representing 75,000 audio and video content creators, providing advertising opportunities, distribution, hosting and more. Also, Todd lives in Hawaii and was inducted into the Podcast Hall of Fame in 2015.

SHOW NOTES:

0:55 - How does a person get into the Podcast Hall of Fame?

1:39 - What does Todd (and Blubrry) actually do?

4:10 - Todd's worst interview ever was live...at a tech show...with a foreign guest...and the rest is history.

7:17 - Get a free 30-day free trial of RINGR Premium.

7:50 - After 3,000+ interviews, how does Todd prepare? What's important? What isn't?

9:32 - Todd lives in Hawaii...and wants to move back to the mainland. WHAT?!?!

10:45 - A terrible accident left Todd in the hospital for 13 days...and it changed his life forever. Learn how.

13:30 - Connect with Todd on Twitter, Blubrry on Twitter, or visit him at Geek News Central.