Everything you’ll ever need to know about crushing the interviewing game

Jordan “J” Gross
Aug 14 · 34 min read
Photo by NeONBRAND on Unsplash

“Massive thoughts must be followed by massive actions. There is nothing ordinary about the 10X Rule. It is simply what it says it is: 10 times the thoughts and 10 times the actions of other people…You never do what others do. You must be willing to do what they won’t do and even take actions that you might deem ‘unreasonable.’” Grant Cardone

It was March 20, 2019, early evening, and I was wrapping up a gym session before heading out to dinner with my family. I grasped the cold metal bar in between my hands, arms shoulder-width apart. I peered over to the weights on my right and my left, and just as Grant Cardone uttered the word “unreasonable,” I thrust the 225 pounds up off the rack, dropped the bar down to my chest, and exhaled audibly as I pushed the bar back up and onto the rack.

I must be willing to do what they won’t do and even take actions that I might deem “unreasonable.” These words ring true for me each and every day.

A combination of Hal Elrod and Grant Cardone brought me to this podcasting journey of 90 podcasts in 90 days. Hal Elrod, the author of “The Miracle Morning,” a book that has sold almost two million copies in the last eight years, swears by podcast guesting. He attributes the overwhelming majority of his book’s success to his appearing on over 350 podcasts in the first months and years that his book was released. It was these consistent and informative conversations that spread the awareness for his love and passion for morning routines.

As an admirer and now friend of Hal’s, I knew that with a book of my own coming out in early 2020, “The Journey to Cloud Nine,” what better way to begin sparking interest for this book than to follow in Hal’s footsteps and start podcasting?

I’m a very symbolic and thematic person, and with “The Journey to Cloud Nine,” the Cloud Nine coaching that I do, and the Cloud Nine interviews that I do with other people, this number nine is omnipresent for me at the moment.

So, as I thought about doing podcasts on March 20, and I heard the motivational and inspiring words from Grant Cardone about being unreasonable and 10x’ing everything that we do, I came up with the following formula.

Cloud Nine — so the number 9. 10x that — so I get 90 podcasts. What amount of time would I, and others, deem as unreasonable? 90 days.

I am going to do 90 podcasts in 90 days.

Podcasts are one of the greatest gifts we’ve ever received as content creators. I can apply the lessons that I’ve learned from my journey to 90 podcasts in 90 days in all initiatives I take on moving forward, and not just podcasts. They’re applicable in business, in relationships, and in every aspect of our lives. You can also consider using these different lessons in any challenge that you take on. I can assure you they will come in handy.

The remainder of this piece will provide six lessons I learned in 15 different categories, with those categories being:

  1. Preparation
  2. My Why
  3. Consistency
  4. Outreach
  5. Organization
  6. Overcoming Fear
  7. Interview Preparation
  8. Guesting
  9. Giving Back
  10. Podcasts Hosts and Podcasts
  11. People
  12. What I Will Do Differently Next Time
  13. Transferrable Skills and Experiences
  14. Me
  15. You

On Preparation

This section is on preparation for the entire journey as a whole — not to be confused with the preparation later on for each individual interview! Prepare, prepare, prepare is the name of the game. Going into this process with a strategy and formula for success made it so much easier to stick to the plan and hit my goal.

90. Do not just get started

Normally, when I have an idea, I jump right into it and figure things out as I go. But, with this podcast journey, whereas I normally would have begun on March 21 after having the idea, I decided to take a step back and take the entire month of April to prepare for the 90 days. And so, those 90 days ended up becoming May to the end of July. Having the extra month to prepare was monumental in ultimately achieving my goal.

89. Begin with who you know

Before doing any research or outreach at all, I thought about the people within my network who I knew already had podcasts, and I reached out to them first. The people who already knew, liked, and trusted me were the easiest to get on board, and it was easiest to get invitations onto their shows!

88. Proceed with who you sorta know

Once I had exhausted my network of friends who had podcasts and would be willing to invite me onto their shows, I moved onto the next-best place for me. I’ve been growing on LinkedIn steadily since October 2018, and I have a considerable number of first connections on that platform. I filtered my search on LinkedIn by typing “podcast host” into the bar, and 546,000 people came up. Once I narrowed it down again to my first connections, there were 441 people who had either podcast or host on their profiles. I then exported all of these names into an Excel spreadsheet.

87. Know your audience

This goes without saying, but you have to know who you’re talking to, and also what topics you can and are going to talk about when you appear on these shows. For me, I typically talk about purpose, meaning, fulfillment, and happiness. I can also sprinkle in some sales, marketing, and entrepreneurship, as well. In going through all 441 hosts and determining what kinds of shows they had, I brought it down to 252 who somehow knew or knew of me, who I could reach out to and ask about being a guest of theirs.

86. Know yourself

I wrote down 20 different stories that I could somehow relate to any question I could possibly be asked during any interview. Writing these stories down allowed me to know who I was as a person and what exactly I wanted to talk about during each chat.

85. Know your why

Before going into this podcast journey, I had to discover why I was doing all this. Was it solely to promote the book? Was it to push my coaching? Was it just to practice? I decided, ultimately, that I wanted to send people to my website and have them sign up for my email list. And so, whenever the host asked where the listeners could find me, I simply responded by saying the URL of my site and to put their email in the email space at the top of the page!


On My Why

At first, I didn’t think too much about why I was doing this, other than to prove to myself that I could achieve something ambitious and to spread the word about my book. But the more conversations I had and the more I considered my overall intentions, the more I developed a clear overall reason for why these interviews were all so important.

84. To show others the grit, determination, and resilience it takes to gain momentum

I documented my journey every step of the way for my audience on LinkedIn, and I’m documenting my journey for all to see right here and right now in this article. One of the primary reasons why this mission was so important to me was because I want others to feel more confident replicating a process in which they need to reach a particular goal. I wanted to show the true ins and outs and behind-the-scenes of how exactly this all came to fruition.

83. To share the message of living a Cloud Nine life

I believe in what I’m talking about. I know that helping somebody find their core values, their true purpose, and what is most meaningful and fulfilling to them will give them an opportunity to reinvent the lives they’re currently living. I wanted to share the stories of people I have interviewed, heard from, and worked with about how living a life in which you blaze your own trail and navigate your way through the clouds leads to one of more happiness, more impact, and more satisfaction overall.

82. To share the real me with others

Through articles, through talks, and through content creation, I believe a lot of the time a skewed version of a person can be created, and a façade can be taken on that’s different from who the person really is. I wanted to use this opportunity to show everybody the real me. My background, my stories, my feelings, what I’ve been through, and what I’ve achieved. I wanted to show how 100% authentic I am and always will be. It was and is so important to me to remain this way and have everybody know the voice, the feelings, and the stories of the guy in front of this computer.

81. To spread awareness for the journey to Cloud Nine

I need to get something tangible out of this as well! If there were no benefit for me at the end of the day, then sure, I would have some great conversations, but why would I want to turn them into podcasts? I believe so much in the book I have coming out and the coaching that I’m doing, and I know that the stories throughout our lives that we consider cloud nine moments have shaped the way that we should be living. I’m here to help uncover that.

80. To prove to myself I can achieve the unreasonable

There’s nothing memorable about the unremarkable. I knew that I had to do something remarkable in order for myself and others to truly remember and resonate with this experience. Setting a lofty goal and doing every single thing in my power to achieve it has been an experience unlike any other, and I will take this with me for the rest of my life.

79. To share the lessons I learned

This article was the original purpose for doing all of this! Not only did I want to document the ins and outs of the process while it was happening, but also, I wanted to reflect on it afterward and share with other people how they could do this too. I always begin with the end in mind. Knowing that at the end of this I was going to get to do a write-up of this whole experience and teach people how to do what I did was definitely a driving force as to why I wanted to get this thing up and running.


On Consistency

Being consistent and persistent was imperative in not getting overwhelmed and sticking to the plan the entire time. In anything we set out to do, turning it into a habit is essential to success. Consistent and deliberate effort with intention is the best way to create a habit.

78. Don’t do everything at once

Starting on April 1, I decided that I was simply going to reach out to 10 people each weekday. This took about an hour given the way I was contacting people (I’ll get more into that), and it allowed me to work in a quick sprint in which I knew that my main objective was to get out my 10 pitches.

77. But, you can also do everything at once

With that being said, if there was a day in which I really felt in the zone, I would send out 20 or 30 pitches and maybe do a little bit less on a different day.

76. Don’t be too hard on yourself

Whether it was a day where I was in a groove, a day where I sent out the normal 10, or a day in which I sent out none, I believe that the key thing in not getting too stressed or overwhelmed was that I had a sense of awareness in regard to exactly what was going on. I also had a bit of leniency because on days when I didn’t hit my target, I knew I would make it up! At the end of the day, this is supposed to be fun. Giving myself strict limitations and penalizing myself wouldn’t be fun, now would it?

75. It won’t always work

There were times when I wouldn’t hear anything back from podcast hosts, or I would get a rejection, even though I did the same exact thing for hosts who invited me onto their shows! Stick to your script, assess, and evaluate, but don’t deviate too much just because you receive a no.

74. Each person is different

What works for one person may not work for another person. I remember a guy who messaged me back saying, “90 podcasts in 90 days, huh? I wouldn’t feel so special if I were just another show in your journey. Good luck.”

But then again, a different lady sent me a message saying, “90 podcasts in 90 days! Count me in, I would love to be a part of your journey!”

You can’t please everybody, and if you try, you end up pleasing nobody. Don’t let a rejection or a person who isn’t on board with your mission divert your plane in a different direction. Stay the course.

73. But treat each person as equally as possible

I’m human, and there were some shows I knew I really wanted to be on more than others. Shows that more aligned with my mission, shows with famous hosts, and shows with larger reaches were on my list, but I couldn’t let this impact my consistent approach. Whether the show has 500,000 listeners or five, reach out to each and everyone with respect and authenticity.


On Outreach

This is definitely the most important section, so please read this one very carefully! Here, I’ll document the exact strategy that I use to not only get onto podcasts, but also to acquire coaching clients, book speaking gigs, and get on the TEDx stage. The way that you connect with people is everything, and with the approach I’ll share, you’ll come from a place of genuine curiosity. The people you’re connecting with will surely appreciate that and take notice. I had a three-paragraph approach to each message, and I’ll share that in lessons 70, 69, and 68.

72. “No” is not the worst thing that can happen

My mom always says to me: “J, what’s the worst thing that can happen? They just say no?”

And while I never like to disagree with my mother, with this particular saying, I would love to make a slight modification. I’d like to say this: “The worst thing that can happen, if you present yourself in the best way possible, is that they’ll say no.”

Picture it this way. If you reach out to a podcast host and you say, “Hey, saw you had a podcast, you should really have me on because I am a genius, and you’re stupid if you don’t invite me to an interview,” then the worst thing that can happen is not just that they’ll say no. The host will certainly say no, but also, they may tell all of their podcast host friends to keep an eye out for you, they may never want to chat with you ever again, and they may even bad mouth you publicly to make an example of how not to reach out.

So, when reaching out, make sure to present yourself in the best way, and then the worst that can happen is just that they’ll say no!

71. Do your research

The first step in reaching out to anybody in the world in this day and age, especially people who are important to you, is to do your research. Go into LinkedIn, check for mutual connections, check for common skills and interests, check for similar work or academic experience, and try to find some sort of commonality. This will immediately set you apart.

After this, research their podcast, duh! What do they talk about? What kinds of guests do they have on? Do you know any of their guests? What’s the format? What’s the style? Maybe listen to an episode! Once you do and consider all of this, you’ll have so much more to talk about when you reach out to them.

70. Start with them

Nobody wants to hear about you and what you’re doing! Well, they do, but not right away. Start by focusing on the other person, and use some of the research that you’ve uncovered to begin crafting your message. Tell them about what you’ve learned from their show, how they’ve impacted your life, or how you resonate with their message. Show them that you really know who they are. A little bit of praise right off-the-bat also never hurts:

“Hey ____! ______ is such an awesome concept for a podcast, and with 387 episodes under your belt, and it looking like you post one every weekday, you are certainly practicing what you preach!”

Short, sweet, and simple, but it shows that you’re interested and have an appreciation for the other person’s work.

69. Then talk about you

You do need to present yourself and the work you’re doing at some point in your outreach. And so, right after you speak about them for a bit, then integrate that into you and what you’re doing. This message can be copied and pasted since you’re doing the same thing, but adjust it accordingly based on the host and what you’ll be talking about on the show. Make sure to focus on impact here and what you’re doing for other people, rather than yourself!

“This year, I’m spreading the feeling of living life on cloud nine by helping people attain their cloud nine lives through finding true meaning and purpose. I’ve interviewed dozens of people in an effort to understand what it takes to create cloud nine moments and cloud nine lives, and I’d love to share with your audience.”

68. Finally, talk about us

The third and final piece of your three-paragraph initial outreach note is all about what you and the host can do together. At the end of the day, the most important person to consider during this exchange isn’t you or the host, but rather, it’s the audience. It’s the people who you both are going to be addressing when you actually have your conversation. With that thought in mind, mention one or two specific insights that you’ll want to discuss that add to the listeners’ lives of whatever show you’re on.

“During our discussion, I really think we can hit on some of the findings I have discovered in regard to uncovering some of our most important memories in determining what purpose in our lives we should be living toward. Your listeners who are stuck or uncertain about their futures would gain tremendous insight!”

It’s specific, it’s actionable, and again, it shows I know who and what I’m talking about.

67. Don’t ask to be on their podcast

This is the number one most important lesson in outreach! In every single message I sent to somebody, I never asked to be on their show. I ended each conversation by asking if they would be open to having a discussion about having me on their show. This led to essentially two options. First, they would say OK, and then on the phone, I would have a chance to seal the deal. Or, second, they would say, absolutely, here’s my scheduling link, no conversation necessary!

“I was wondering if you’d consider having me on your show. I’m happy to discuss further and provide whatever value for you that you need!”

Notice one last time how I’m always trying to bring value to the conversation and focus on everybody except for myself! This is critical.


On Organization

When you’re reaching out to hundreds of people, there has to be an organized and methodical approach to all of this madness. Creating a spreadsheet, which I’ll share with you below, was probably the most crucial thing I could have done to organize my outreach.

To the left of these columns are the host’s name and the name of their show, which I’ve omitted for their privacy.

66. You must have an initial contact date

When you first contact somebody, make a note of the date. You’re not going to just reach out to this person once, you’re going to follow-up! So, knowing when you first reached out is important so that you give proper time before your second message.

65. You have to keep notes

It’s going to be extremely difficult to remember every single conversation you had with each person, so you need to create a section where you leave yourself reminders.

64. You must plan and schedule in advance

Once you get a confirmed interview, put it in the calendar! Make sure to put it in both your Excel sheet and on either an online or physical calendar. This way, you’ll never get overlaps and schedule two things at the exact same time.

63. Give everything a color

I treated this much like a sales process. Once I reached out to somebody, they received a color from the beginning of the process to the end.

Yellow = First reach out, no response

Orange = Second reach out, no response

Light Green = Interview scheduled

Dark Green = Interview accepted, but not yet scheduled

Light Blue = Interview completed

Red = Interview not offered

62. More organization = more talking points!

One unexpected lesson I learned was that people really, really wanted to know how I was going about doing all of this. Because I was organized and diligent about this, and I had the Excel sheet to prove it, it was much easier for me to share with others how exactly I could do all of this.

61. Do it now!

Don’t wait to put things into your spreadsheet! This is when you forget dates, you forget who you reached out to, and it can create a nightmare for you moving forward. If it takes less than 30 seconds, do it right away. Entering something into your spreadsheet takes no time at all.


On Overcoming Fear

Putting yourself out there is a scary thing. Self-promotion is a scary thing. There’s so much to be learned from an experience in which you are truly outside of your comfort zone, and you’re doing everything you can to push through and continuously live on the edge of fear. When podcasting, you may be afraid of the outreach, pitching yourself, or speaking on a certain topic. I was scared of all of these things. Each message and each conversation, I had to learn how to embrace the fear.

60. How to overcome doubt

Why would anybody want to talk to me? Why would anybody want to hear what I have to say? Why would people be interested in my story? These are the doubts I had racing through my head as I approached each host.

But, the one thing I kept in mind at all times was this: if one person takes one thing away, if one person thinks one different thought, and if one person feels one different emotion, then what I have to say has worth. This is how you overcome doubt — by knowing that you matter in some way to somebody.

59. How to beat imposter syndrome

I’m not an expert. I’m not a Ph.D. I’m not a genius. This is what I was thinking when I was scared to share what I had learned with others, because I was unsure whether or not people would buy in or be receptive. Why should I be viewed as an authority?

The reason is this: I’ve put in the time, I’ve put in the research, and I’ve put in the effort. I’ve uncovered the stories. I’ve established and picked up on the principles, patterns, and concepts. With the wealth of information out there, there is only so much “new and unique” we can present to people. Often times, it’s the way it’s presented, combined with the stories that we tell, that truly influence people. Knowing and understanding the stories that I wanted to share allowed me to overcome imposter syndrome.

58. How to not feel like a bother

This is a fear of mine that I’m constantly working on. I never want to be viewed as an annoyance. Allow me to provide a quick example of an interaction I had in which I felt like I annoyed the host, and how I responded to immediately assure him that I didn’t mean to be a pest.

This is the response I received from a host after sending my usual message:

“So, I’m assuming you don’t read my article about wanting to be on a podcast. Lol.”

My response:

“I just read your article, and I re-read my message, and I want to apologize. That message was rather me-centric, when the majority of my outreach has been focused on us and them, the audience. The sloppy message I sent came from a last-ditch effort to book a few more shows to hit my goal, and I deviated from what has been working and what I know works. I have literally given tips about podcast outreach totally in line with your article, and I did not practice what I preach. Thank you for bringing my attention to this!”

I admitted my mistake and I tried to reconcile! Authenticity is how you overcome annoyance.

57. How to not fear self-promotion

To be totally honest and authentic with this one, I don’t have a great answer. This is one where the more you do it, the more comfortable with it you get. For me, I know the more I can share my message, the more people I can help. My success is somebody else’s cloud nine, and so self-promotion is part of the process, so long as it’s done carefully and genuinely.

56. How to not mess up!

Podcast hosts are extremely reassuring in that they will let you know that anything can be edited out. This gives you the confidence to know that you can start over, scratch a thought or story you don’t want to share, or get a do-over. But, the number one key to not being afraid of messing up, is preparation, repetition, and practice!

55. How to never give up

The fear of failure definitely radiated around my mind. With just four days left and six shows left to book, I was definitely nervous. But I stuck to my plan and strategy, I found more hosts, I reached out to prior hosts to see if they had other connections in the podcasting world, I didn’t panic, and I pulled through! When in that stress mode, it’s most important to keep doing what has been working.


On Interview Preparation

This section will be a little shorter, but critical nonetheless! Each episode, you want to provide the most value possible and give your best effort for the host and the listeners. These are some of the key insights I noticed from the 90 shows.

54. Have a conversation with the host before

All of my best conversations came when the host and I already had a bit of rapport, either through a conversation we had weeks prior, or right before the chat. When we just got on and began talking, it felt more like a getting to know you than a valuable podcast conversation. Most hosts will want to do this, but if they don’t, make sure to ask if you can.

53. Listen to a previous episode

I must admit, I wasn’t able to do this for all 90 shows, but when I did, it was extremely helpful. I got a feel for the interview style and format, the host’s personality, and the length. I also just felt more comfortable. When I didn’t, I was more on my toes, which works for some people, but I still recommend putting in your prep work, for sure!

52. Read the reviews

Check out what the listeners have to say! After all, they’re the people who you’re trying to appeal to and reach. Head over to iTunes and see what people like and dislike about the interviews that they’ve heard, and try to plan accordingly!

51. Check the host’s LinkedIn/website

Conversations are best when they’re intimate. Conversations are best when people know things about one another. If you can have a conversation in which you bring up something you know about the host, you’ll not only impress them, but you’ll also come off as more relatable and engaging.

50. Know your story

Almost every single host is going to ask you for your background, where you came from, where you’ve been, where you are now, and where you’re going. Those four components are exactly how I tell my story! If you have this down to a science, then you can play around with it, change it up a little so it’s not too boring, and have a definitive answer to start the interview.

49. Write down 20 of your favorite stories related to your topic

We’ll get more into this in the next section, but the more ready you are with stories, and the more you’ve thought about the stories you wish to tell, the better off you’ll be!


On Guesting

Once you’ve prepared for the interview, it’s time to get started! Remember, you’ve done your part in getting on the show, so you know you’re worth it. But you don’t want to stop here! You want to make sure you give the best interview possible and add the most value possible to the listeners, so you can get the most value for what you’re promoting in return.

48. Be appreciative

The first thing you must do on each and every show is thank the host for having you on, and thank the listeners for listening to you. If you show you’re grateful for the opportunity, people will immediately join your team much quicker than they would otherwise.

47. Your story should spark conversation

The best podcast conversations are one that evoke curiosity. They are a deep dive into a background, a mindset, and a process, all driven by storytelling. You’re always going to be asked about your story. Always. This story should be a representation of who you are, rather than what you’ve done. Also, it should highlight many different experiences, so that the host can generate questions from it. The conversation should go naturally from there.

46. Stories are your best friends

Every question you’re asked should have a story attached to it. This is true in regard to podcasts, interviews, and even conversations on the street!

This makes the conversation more engaging. This makes you look like more of a human, rather than an encyclopedia. This makes you look like more of a seasoned expert than someone who’s just regurgitating somebody else’s words. This makes you look like you truly care! You want to have a large number of stories you can use to answer different questions so that you can keep it fresh for you, the host, and your listeners.

45. Create something out of nothing

I had new stories that I was telling on every single show. The reason for this was twofold. One, it was so I didn’t get bored telling the same stories! Two, it was because finding beauty and lessons in the little things is delightful to hear for the audience. Relating everyday events to the conversations you can have on podcasts is a great way to show your expertise and get people interested in what you have to say. It also gets you constantly thinking and being creative, and it can do the same for your listeners as well.

44. Say something different

What makes you stand out?! How do you deviate from the rest of the pack? What makes you memorable? There has to be some sort of differentiating factor about you and your interview. What that is, is up to you to uncover.

43. Ask for feedback

The goal is to try and get better each interview. It’s difficult for me to judge overall performance, so I try to get better in a few different categories.

Creativity

Originality

Value Add

Energy

I asked each interviewer to provide me with feedback on my interviewing skills on these categories so that I could be better the next time. This paid tremendous dividends in my performance, as I was so much better in interview 90 than I was in interview one!


On Giving Back

You’re getting a lot from the podcast host, and so it’s only right that you give something back in return. Below are a couple of the most amazing and creative ways I was able to give back to these wonderful humans who allowed me on their shows!

42. Leave a review

Head over to iTunes and leave the host a review! This will allow more people the opportunity to listen to the show, as reviews boost their rankings and positively impact the algorithm.

41. Share on your website

I created a page on my website dedicated to all of the interviews that I did during my 90 podcasts in 90 days journey. Whenever the interviews are available, I put them on that page and link to the episode and the host’s LinkedIn.

40. Share on social media

Every Wednesday, I would put up a post of all the podcasts I appeared on the week prior. I would tag the hosts, thank them, and then in the comments, I shared the interviews that were available that week. This spreads the word for not only for the show, but also the person.

39. Write personal recommendations

This was by far the most rewarding thing I began to do after each interview. I would provide an honest reflection of the conversation I just had and the person I just spoke to, and I would leave it as a recommendation on LinkedIn. This immediately put me in a state of tremendous gratitude, it made me smile, and more importantly, when other people received this message, it literally changed their day. Below is an example of a response to a recommendation I left:

“I needed that right now; am at the cemetery paying my respects to my grandma who passed away (Alzheimer’s complications). We do things for others without knowing the consequences. Thank you very much.”

38. Write handwritten thank you cards

I didn’t do this, but it’s definitely a unique and meaningful touch. Taking the time to physically write out a thank you card means a lot, especially in this day and age!

37. Ask what else you can do

Making introductions, promoting products or courses, doing an interview in return if you’re able — these are all great things that podcast hosts value. In one scenario, I helped a host increase her number of email list followers, and she offered to get me on two additional shows, just because I was willing to help her! Help others — you never know what will happen. It will also make you feel great.


On Podcast Hosts and Podcasts

I learned a surprisingly good deal about hosting a podcast and what it does for the hosts and the people who listen. A couple of the top insights are below.

36. Podcast hosts are people too!

Podcast hosts have scheduling conflicts, they have other jobs, they have other commitments. Many of these hosts do this on the side or do this infrequently. Some do it every single day! Each host is a different human being, so make sure to treat them as so.

35. Podcast hosts cherish their audiences

Every single podcast host has a devoted group of listeners. Whether that be their three best friends or their three million followers, podcast hosts know who’s listening, and more importantly, they adore who’s listening. Make sure to take this into account when approaching any host or interview.

34. Podcast hosts have a difficult job

Podcasting is a lot of work! Between scheduling tools, recording tools, editing tools, posting methods, website maintenance, marketing, booking guests, and so much more, there’s a lot to do. I have a tremendous amount of respect for all that these people do.

33. Podcast hosts have their own objectives

It’s important to understand the why behind each podcast. Why is the host doing this? What’s their story? Make sure to ask questions back if and when you get a chance, so that the conversation goes both ways. Once you know more about why they host this show, you may be able to better guide the conversation so that the listeners can get the most out of it.

32. Podcast hosts like unique perspective and stories

These people hear a lot of thoughts about the same subjects all the time. I noticed that hosts would get visibly excited when I would have a different take, a challenging of popular opinion, or a really awesome story that helped me prove a point. Try to find areas where you can bring in your own personal spin so that the host gets even more entrenched in the conversation.

31. Podcasts are a business

Podcasts serve a business purpose in almost every single scenario. Whether the podcast charges money to appear as a guest (some do, I didn’t do any of these), or if the show is a tool that is part of a sales funnel, the podcast is a means to generate more business for the host or the host’s company.


On People

I thought I knew a lot about people before this experience, but my goodness. Meeting and interacting with 90 strangers and reaching out to over 200 of them, I learned some fascinating new insights about humanity.

30. People can be supportive

Every week, I would post about my podcasting journey, and I would receive an outpouring of support from thousands on LinkedIn who liked, commented, and viewed my post. Each week, people motivated me to keep pushing forward and achieve my goal. This was truly inspiring and eye-opening about how the people around us fuel our endeavors.

29. People can be helpful

Not only were people supportive in response to these weekly updates, but they were also extremely helpful. I would have people reach out to me expressing how they knew a podcast host and they wanted to put me in touch. Or, podcast hosts themselves would see my post and reach out, asking me to be on their shows themselves! Again, this was another demonstration of the innate good within us, and the desire to see others succeed.

28. People can be surprising

I did a show with a host from Bulgaria, and we had a great interview. However, I didn’t follow my own advice and look into him beforehand. If I had, I would have found out something mind-boggling. This sophisticated, mature, and insightful interviewer was only thirteen years old! People are truly fascinating.

27. People can be aloof

Some people are very hard to get a hold of. There were many hosts who would answer once, and then it’d be another few weeks until they answered again. There were hosts who didn’t answer, hosts who did and then stopped, and hosts who did everything in between. The most important thing here is that so long as you focus on you and your positive interactions, then you will be fine!

26. People can be vicious

I won’t harp too much on this one, but the harsh reality is that sometimes, people can be mean. Sometimes, people can deliberately try to hurt your feelings. Sometimes, people don’t want to see you succeed at all. With people like this, I always remind myself of two things. First, this person isn’t in the arena, and they’re not putting themselves out there — they’re a spectator, judging from afar. Second, there’s most likely something happening in their life that’s way worse than what’s happening in mine. I never engage or argue back. I just try to understand.

25. People are all different

The main message about people is that they are all different! So, no matter what, in order to get around this, you have to show up as your 100% authentic and genuine self in every situation and respond to each and every person accordingly.


On What I Will Do Differently Next Time

I’m a person who would never change my past, because then I wouldn’t be here where I currently am in the present. But this does not mean that I don’t evaluate my past and consider alternative or more effective ways of doing things. If I were to go through this 90 podcasts in 90 days journey again, which I will, here’s what I will do differently.

24. I will schedule even further in advance

Although I thought I was ahead of the game reaching out in March and April for May-July shows, I was still a little late for some shows. Some were booked three to five months in advance! Currently, I’m already planning my next round for January, and I’ll start reaching out in the next few weeks. Book early — hosts appreciate that!

23. I will have an even clearer takeaway

I wanted people to sign up for my email list, which can be found by entering your email at the top of my website. But, next time, I think I will make an entirely new landing page in order to get people to where I want them to go. This way, they won’t have to navigate and look around for themselves when they get on the site.

22. I will focus more on when the episodes are released

My goal this time around was to schedule and do 90 interviews in 90 days. When the episodes were actually released was not a part of my goal. For the next go around, I want to place an emphasis on when the episodes come out because I want them all to be around book launch time. You must consider the end goal when going into a marketing campaign like this!

21. I will jot down reflections each day

I think documenting how I was feeling each day during this journey could have been helpful for others looking to replicate it. Sometimes, it’s not only the tangible steps and processes but also the thoughts and feelings involved that may help somebody in a similar situation.

20. I will use more than just LinkedIn

One of the things I’m already doing for LinkedIn, is I’m compiling a list of podcasts that I would want to go on based off of my research on iTunes of the shows within the categories with which I can speak. I focused exclusively on my LinkedIn connections this go around, but next time, I’ll have to put even more effort into creative ways to connect to hosts aside from just LinkedIn!

19. I will get a coach

I think it would be majorly beneficial to have somebody on my team. Whether that’s a business coach, an organizational coach, or a specific interview and podcasting coach, the journey, although surrounded by love and support, did get lonely at times. I would love to take on somebody who is fully invested in my growth, my definition of success, and my excellence.


On Transferrable Skills and Experiences

As I mentioned, this process will not only help me in podcasting efforts moving forward, but it will also help me in sales cycles, marketing projects, outreach efforts, and so much more. Below are a few examples of what I will be using from this experience in other facets of my life.

18. When interviewing other people

I will certainly be using the ‘you, me, and we’ approach when reaching out to people who I would like to interview or get advice from in the future. Adding value and focusing on them is the best way to approach people, and especially if you can creatively add value, it’ll be even better!

17. When reaching out for book endorsements

This is very specific for me as an author, but I will follow this systematic approach when I am reaching out to bigger influences for book endorsements. I’ll have a spreadsheet, I’ll keep track of my outreach, I’ll add value, I’ll set a lofty goal, and I’ll achieve it!

16. When promoting products

For me, in this case, it will be books. But I think the public announcement of my goal combined with the personalized approach is a prime way to get people on my team and wanting to buy the products I’m putting out there. It’s essential to remember this personalized approach when selling anything.

15. When promoting services

The same goes for services! I want to sell my coaching packages, so I’ll have a target audience, a pitch, and a value add. I’ll do my research, I’ll prepare, and then I’ll serve.

14. When starting a new project

One of the primary goals for this entire voyage was to go behind-the-scenes and learn what it takes to build momentum for anything! It was to show the resilience, the determination, the effort, the relationships, and the mindset that’s required for getting anything started. This is what you have to do!

13. When coaching aspiring content creators

This has been one of the most transformative experiences of my life, and for the people who want to do something like I did, I’ll certainly be using this example to relay the messages I learned throughout my journey.


On Me

The last three months have been an absolute whirlwind. I can’t believe how quickly they came and went, and I can’t believe how I was able to navigate my own plane through the clouds, withstand the turbulence, and land on my own version of cloud nine. I learned so much during this process, but one of the most important things I wanted to share was how much I learned about myself when going through this.

12. I thrive off of being unreasonable

As I come close to the end of this list here, I started considering Grant Cardone’s quote that jumpstarted this entire journey. I crave unreasonable experiences. I shine when the odds are against me. I’m ignited by overcoming the odds.

I have a handwritten note in my closet in my room that reads, “If people begin to question your sanity, then you’re onto something.” When others believe that what you are doing is mad, insane, out of reach, or impossible, it’s my intention to show them just how wrong they really are.

11. I work best under pressure

I sort of always knew this, but I always come out on top when I’m under the most pressure. As a former soccer goalie, penalty shootouts were always my favorite time of the game, when for many others, it was their most feared.

Similar to the first point, when the result seems unexpected, I make it my mission to come out on top. With two days remaining and three podcasts left to book, the odds certainly seemed against me, but I booked the shows and got it done. I always knew I would get it done.

10. I’m only scratching the surface of the man I know I can become

This entire experience has proven to me that I have so much left to give, to share, to teach, and to learn. I’ve realized how appreciative and grateful I am to have achieved and been awarded so much in my 24 years on this Earth. But I only think I’m about 24% of the way to the person I can really become. This journey has re-energized me, recharged me, and resurged me. I’m ready to continue with this momentum.

9. I’m definitely an introvert

As somebody who has had all these conversations, wanted to have all these conversations, shares content daily, and seems energetic and upbeat, I bet you’d guess I was an extrovert, right? Guess again! My Myers-Briggs always deviates between ENFJ and INFJ, so I’ve just gone with the middle and said that I was an ambivert. But, the distinction here is about where we get our energy from and where we go when we need to get our energy back.

For me, these conversations were exhausting. After six or seven podcasts in a day, I definitely didn’t want to keep chatting. Rather, I put my head in a book or typed up some recommendations and took time to myself to reflect and recuperate.

8. I love change

Doing 90 podcast interviews, it was destined that many of the questions would be the same, I would have to tell the same stories, and I would have to provide the same answers. With that, I found that my favorite interviews, the most memorable ones that pop out in my mind to this day, were the ones that were different, deviated from the norm, and changed the way I had to think about or answer questions. I think this makes sense, as this is really how I have lived my life!

7. I enjoy fluid conversation more than just being interviewed

Don’t get me wrong, I really love being interviewed! But I really missed the opportunity to ask questions back to the person chatting with me. I’m a curious person, so every time I answered a question, I wanted to know what the host thought about it as well. I like basing conversations off of other people, learning about them and understanding their stories. I actually had the chance to flip the script in one podcast interview, and I ended up asking all the questions. Maybe podcast hosting is in my future!


On You

As I mentioned in my purpose for doing this whole podcast tour, one of my primary motivations was about you. The listener, the reader, the content creator, the podcaster, the YouTuber, the aspiring entrepreneur, the mom, the dad, the brother, the sister, the cousin, whoever you are, I learned a few things about you that I wanted to share with you as well. So here goes.

6. You can set ambitious goals

Setting the goal is the first step. Becoming the person who can reach that goal is the most important step. It’s not about hitting the goal, but rather it’s about doing every single thing in your power and giving yourself the best opportunity to achieve the goal that matters most. Accomplishing it is just an added bonus!

5. You can get outside your comfort zone

You have the ability to immerse yourself in an experience that’s daunting. You have the freedom to choose to live on the other side of the fear. You have the ambition to choose the uncomfortable. In anything you do, it’s the scariest, most challenging experiences that end up being the most rewarding.

4. You can build lasting relationships

It’s possible to make a mutually beneficial, long-lasting relationship with a total stranger from across the world. With common interests and a devotion to a much larger goal of helping the world, you and another human being can come together, have a conversation, and start to make a difference.

3. You can be an authority

The more work you put into something, the more you’re going to be viewed as a voice in whatever field you’re working in. Research, ask questions, interview, write, read, and be curious. Then, you’ll slowly but surely become adept at whatever it is you wish to speak about.

2. You can share your story

No matter what, every single person on this planet has a story. It’s up to you to uncover it and then share it with others. You never know the one person who may resonate with what you have been through or what you have to say, so please don’t be reluctant to share who you are, where you came from, where you’ve been, and where you’re going with the world.

1. You can appear on 90 different podcasts in 90 days

With the lessons learned and the strategies shared throughout this article, I truly believe that anybody reading this can go on 90 podcasts in 90 days. I believe you can do 100 podcasts in 100 days. I believe that you can be audacious, strive for greatness, and become the version of yourself who has the opportunity to accomplish your goals.


Final Thoughts

There’s nothing memorable about the unremarkable. Sure, I could have done 30 podcasts in 30 days, I could have aimed for 100 podcasts in a full calendar year, and both of these would have been fantastic.

But, if you truly want to stand out, if you truly want to push the envelope, you have to do something that is without logical thought or explanation.

90 podcasts in 90 days. Check.

It has been quite the journey and experience, and I can only imagine what will happen next as I strive for my next goal: 90 in 45!

Better Marketing

Advice & case studies

Jordan “J” Gross

Written by

Author of upcoming “The Journey to Cloud Nine” | TEDx Speaker | Where purpose-driven people reveal their happiest moments → https://www.journeytocloudnine.com/

Better Marketing

Advice & case studies

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