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SPI 651: Top Lessons from Interviewing Billionaires with Jess Larsen

Connecting with your audience through podcasting can be a game-changing strategy for any brand. Here at SPI, we’re already helping many entrepreneurs take advantage of this opportunity. But there’s another, less often talked about benefit of creating a show in your niche.

This episode with Jess Larsen is mandatory listening for any podcaster. Jess hosts interviews on The Jess Larsen Show on Innovation and Leadership with everyone from non-profit organizers to billionaires and movie stars — they’re essentially masterclasses from the people he looks up to most.

Through podcasting, the relationships you can build with top figures in your industry are second to none! But how do you get high-profile guests on your show, and how do you create authentic connections with them that can help you grow your business?

That’s the focus of today’s incredible chat with Jess. Plus, you’ll hear all about how he has leveraged the power of podcasting to go from traditional sales jobs to founding his hugely successful investment group, media company, and charity.

The lessons Jess has learned on his journey are invaluable for any entrepreneur, so don’t miss this conversation!

Today’s Guest

Jess Larsen

Jess Larsen is the Chairman & Co-Founder of a commercial real estate fund called Graystoke Investments, a media company Graystoke Networks, and a charity that combats child trafficking called Child Rescue Association.

He has hosted 800+ episodes of the podcast “Innovation & Leadership with Jess Larsen,” which hit the #1 ranking for innovation podcasts globally with over 3 million downloads, interviewing Billionaires, Movie Stars, Pro Athletes, Unicorn Tech Founders, and other uncommonly high achievers.

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SPI 651: Top Lessons from Interviewing Billionaires with Jess Larsen

Jess Larsen: Where I feel like I really have to watch myself is my innate personality that likes the spotlight, that would like to be a big deal. I really have to ratchet that in because am I name dropping the CEO of this billion dollar tech fund for me, or is it because it’s actually gonna help the person I’m talking to take the lesson more seriously?

And kind of every time that I’m like, oh no, it’s for me so that I can feel important, like I know I need to not say it. And I can’t say I always edit myself, but like that’s my rule is like, am I telling the story for me or am I telling the story for them?

Pat Flynn: You know, I talk about starting a podcast quite often here on the show. And we’ve helped tens of thousands of people start their own show through our courses, and millions of people have watched the videos on YouTube, and I’ve shared a lot about what a podcast has done for me and my personal and business growth.

But I wanted to bring another perspective of what it’s like to start a podcast and what can actually happen when you do so, and also how to navigate those waters of podcasting in case you have one or are thinking about starting one. And yes, YouTube is all the rage right now. Yes, starting a blog still makes sense today. But there’s just something special about the connection that you can make with the other person on the other end with your podcast.

And I, I don’t just mean the connection that you and I are having right now, the host to audience connection, but the connection that you can have with your guest, which a lot of my students and a lot of people who start podcasts, start specifically to get to know other people in your industry and nobody better to talk about this than our guest today, Jess Larsen.

He has a podcast, the Innovation and Leadership podcast with Jess Larsen, and I was recently on his show. And I got to know him and I got to know the archive of his show, which includes billionaires and people that he wouldn’t have been able to connect with otherwise. And I wanted to ask him about that.

How did you get these people on the show? How do you like do business with these people after you connect with them? How do you make it feel real and not inauthentic? And how do you just go about doing what you do, because his podcast is absolutely incredible. So number one, definitely check out Innovation and Leadership with Jess Larsen.

He’s over at Greystoke Media, and you can find him at JessLarsen.net. But stick around because this session, 651, it’s gonna be one to remember for sure. Thank you for listening in today, and without further ado. Ado, ado? I don’t know how to say it, but I do know that Jess Larsen is awesome and here he is.

Announcer: Welcome to the Smart Passive Income Podcast, where it’s all about working hard now, so you can sit back and reap the benefits later. And now your host, when he records a podcast, he literally thinks about you. But not in a creepy kind of way, I promise. Pat Flynn.

Pat Flynn: Jess, welcome to the Smart Passive Income Podcast. Thank you so much for joining me today.

Jess Larsen: Yeah, thanks for having me.

Pat Flynn: You know, I’m grateful that you gave both myself and Matt the pleasure of coming onto your show, Innovation and Leadership. And I’m, I’m so excited to have you on because you’re approaching your creative work in a, in an amazing way that really is built on relationships and the podcast that you built and the sort of people that you connect with there.

This is gonna be a really amazing show, cuz I know that a lot of people will be able to kind of see themselves in, in that journey. And, and you’re just kind of further ahead on that. I think a lot of people will be able to follow your footsteps here for how to, you know, be an industry leader, but also connect with the right people.

And before we get into those tactics and those, those stories, I’d love to know a little bit about how you got here. Like what’s the background behind Jess and how you got to do what you’re doing today.

Jess Larsen: I’ll try to give a quick version. I don’t know how good I am at that. But dropped out of art school to be an entrepreneur.

So I was gonna be a pro snowboarder. I thought I’d be responsible instead and go to art school. Ended up dropping out of that to be an entrepreneur and got headhunted over into investment banking for Citigroup, trying to talk CEOs into letting us sell their companies. And decided, well, we’re selling ’em to these private equity funds.

That’s like entrepreneurship for people with ADD, I have ADD I should have a fund. So started a first fund in my twenties and it was in that process, raised like 27 million for this little fund. And I realized like, man, if I got better at marketing, I wouldn’t have to sell so much. Like that’s like I, I, I developed the wrong skillset. And so that’s when my good friend, a really great entrepreneur and lawyer named Ryan Clements in Calgary, Alberta, who’s like, Hey, have you ever heard of Pat Flynn Smart Passive Income? Like, this is great.

And, like, you were, you were really part of that early journey and like Joe Pulizzi and the Content Marketing Institute people and some of the stuff of like, oh man, like what if I just made entertaining stuff that was helpful, and people came to me instead of like hunting and begging for meetings and all this kind of stuff.

Through the ups and downs, the entrepreneurial like rollercoaster of mega networth completely wiped out, high net worth, completely wiped out, these kind of things, I just kind of kept reading the books, listening to the podcast, watching the YouTube videos, and like more and more and more realized like, this is just such a high leverage opportunity of try to help people in a somewhat entertaining way as a way to start friendships, dig your well before you’re thirsty, these kind of things. My consulting firm that I had hired had a show, they’re called the Arbinger Institute, and I loved it. And when I ended up going to work for them, I was like, Hey, what happened to that show?

Can I host some of those episodes since you’re not doing it? They’re like, yeah, go for it. And I just started interviewing like our best clients from special ops or big corporate clients and stuff, and it was just a lot of fun just having a conversation and I just thought, man, imagine if I could do this for work.

When I quit and started my own management consulting firm, I thought, no matter what I do going forward, It’s gonna be good to have an audience. And so I thought, well, if nothing else, I can just get free ads for our charity Child Rescue. We started back in 2009. And I know I’m gonna do another investment fund at some point, so it’d be great to start like building an audience, build relationships now for when we eventually do that, which, which we have now started our, our commercial real estate fund.

And I got all my learning from audiobooks really. I’m major, you know, listen to maybe three or four books a week. And I was like doing the shows mostly for like the relationship and the credibility boost and building of an audience and these kind of things. And then the shows ended up being like the most valuable learning thing in my life, like getting the stories directly from the source.

And over time as my quality of guests went up, it like really became like major masterclass from my heroes. And the people who wrote the bestselling books, like I’ve read all your books, you know, and getting to have you on the show the other week was like a big win. Like I was so proud to tell my brother and my friends that Pat Flynns coming on my show and I gotta like, I’ve listened to you for so many years, but then I gotta hear it directly from you.

And I typically, like, learn something. It’s typically that people like you who are these experts that I’ve listened to for years, when I actually meet you, it’s like, you live it even harder than I thought you did. And that ends up being the lesson. So it’s like the most fun hobby of all time. And then you know, it turned into multimillionaires becoming investors of our commercial real estate fund. It helped me get clients from my management consulting firm. Google, intel, a 16 billion bank, a 11 billion publicly traded industrial company. And our charity, we’ve got a family office worth hundreds of millions that’s, that’s throwing an event for us next week.

We’ve got public company CEOs become donors, clients of our podcast here. So it’s probably more of an answer than you were looking for, but I’m pretty passionate cuz it’s kind of made everything else work.

Pat Flynn: Yeah, that’s incredible. I mean, the idea, first of all, of starting a show to highlight your own clients is, is, you know, that makes complete sense.

It gives them a platform to share the work that they’ve been doing, but it also rewards them for that hard work, and also allows you to have even deeper conversations with them. And that’s the beauty of a podcast. It’s like, it’s not just the, Hey, let me pick your brain situation, right? It’s, Hey, let’s talk about these things and help others too.

And there’s a lot of people out there who, who are willing to do that. I mean, can you share a small guest list of who’s been on your show to potentially talk about like the caliber of kind of people that you, you were able to track by simply having a podcast and inviting them on?

Jess Larsen: Yeah, so we’ve done, I’ve done over 750 episodes now and it’s billionaires, pro athletes, movie stars, tech unicorn founders, public company CEOs, New York Times bestselling authors, Delta 4, Seal Team Six, CIA case officers, some really amazing non-profit leaders. Like it’s fun to have, like, I got the actor Danny Glover to come on the show from, you know, a Lethal Weapon.

Or I got, yeah Jay Chandrasekhar from Supert Troopers. You know, he directed like, he’s also a director directed, Dukes of Hazard with Jessica Simpson that made like 200 million. And those are fun, but also these like nonprofit leaders. There’s this guy Scott Stiles in Hong Kong, who is so annoyed at the way that the nanny industry was taking advantage of these Filipino women, that he started an agency that treated them well, paid them what they were worth, and changed the entire market for the entire, the entire Hong Kong market.

All these women finally had a choice of someone who wasn’t gonna take advantage of them and play these games and dock their checks, and the entire industry has had to catch up because they just were leaving those agencies in droves to come to him. And he did it just to make a difference. Like the, the money was like nice, but like, he genuinely was like, it was like a, you know, that quote, the way to complain about bad software is to make good software. And those have been like the unexpected like real stories that stuck with me.

Pat Flynn: That’s amazing. And so 750 episodes, I mean, what a, what, what, like have you replaced your audiobooks with these essentially now that you can have these direct conversations? Or are you, are you actually still consuming audiobooks as well?

Jess Larsen: No, I’m probably still two to four audio books a week.

Pat Flynn: Wow. Okay. It’s a lot of information coming in for sure. I’d love to ask you, with the relationships that you’re building from the podcast, you know, a lot of people wanna start a podcast or any kind of show for specifically the advertising dollars that can come with that.

Right? If you gain a certain number of listeners, you can then charge a company to kind of have a little ad spott in there. And I know you, you’ve done some of that. Like, tell me more about the, the real benefit of doing it the way that you’re doing it and how does this ultimately turn into money, but genuine.

And cuz you know, on one hand you could go, okay, like, haha, I’m gonna invite all these top players on and then I’m gonna sell them my stuff. Like, that’s obviously not what you’re doing. How do you approach your guests and those relationships in a genuine manner?

Jess Larsen: So it kinda goes back to this. As an art school dropout, I didn’t have a lot of career options, but I wanted to live in Huntington Beach, California, so my newlywed wife and I could be right, right there for surfing.

Basically all the jobs I could get didn’t pay anything. Except sales jobs. Sales jobs, I could actually make some money. And so I did like cold calling. I did like terrible sales jobs. Okay. I worked at the Yellow Pages. I, I worked for a sales training company and I made more money than any of my friends my age.

Just doing like the brunt force, make the numbers, you know, gutted up and do it. And, and then later I got turned onto, like we talked about the Arbinger Institute. They’ve got great books like Leadership and Self Deception and their, their founder Terry Warner, has a incredible, probably my favorite book of all time called Bonds that Make us Free.

Okay. And it’s all about like spotting your leadership blind spots and that human problems come from objectifying others and how to like spot our own blind spots on that. I call it the Trusted Advisor Sale. When I, when I flip-flopped to really, really getting interested in their life and what their problems are and how like, and what’s their customer’s, customer’s problem.

You know? And then like doing favors for people that weren’t transactional and sending them books and like making connections and using up my social capital on them. It, it’s kind of like this idea of like, I was always trying to go stranger to client. That’s what I thought my job was as salesperson and it switched to stranger to friend, friend to client. And it’s like, I, I kind of got out of the business of hunting. Oh, I’m gonna get them. And I got into the business of farming where I’m gonna fertilize and water all these seeds, these friendships with just having some faith that, that, like Derek Sivers says, money is a natural byproduct of service.

And if I was providing enough of the right service to people, money’s a natural byproduct. And it’s not like I forgot about sales techniques or things like this, but I kind of just didn’t really need them. And I’m like genuinely trying to do them more favors than any salesperson would ever do for them.

And I’m like trying to get out of the, like, in their mind, thinking just the sales guy. And I’m trying to get them to like go shields down and, like, let me out of, like, the handcuffed chair on the other side of the negotiating table of salesmen and get them to invite me around to their side of the table. Of, like, Jess, my advisor who’s actually cares more about my problem than his commission.

And like it’s, I could take my salesman hat off, go over, advise ’em on what they should buy from my company, and then go back and put my salesman hat on and write the contract. It’s like doing that with the show of like, Sure. I wish everybody who came on my show bought something from one of my companies or donated to our charity, right?

But because I have such volume where I know I’m gonna meet however many new people this month, I don’t need to get anybody. I can just become friends with the people I naturally resonate with, connect them to other guests, or send them books or these kind of things, start real friendships and like, it’s not like they don’t know what I’m doing.

They know what my business is. If they’ve got questions about it or they’re interested in it, it’s gonna come up. And if we become a real friend over a matter of months or a couple of years, me saying, Hey, by the way, of course I would love to sell you this stuff, but like, is it ever even interesting to you?

And it’s like friends shooting the breeze, not to salesman, trying to get a client kind of conversation. And if they say, oh, not really Jess, I just don’t think it’s our sale. Or, yeah, maybe, but like, it’s not gonna be in our budget for the next couple of years. I’m leaving at that, but I still say friends and I still make connections and I still check in with them every few months of like, Hey man, it’s been a while. What’s new?

It’s just like this faith of like water and fertilize and what’s gonna grow is naturally gonna grow. I don’t know if that even answers your question. I know it’s kind of monologuing there.

Pat Flynn: No, it does. I mean, it’s, I’m resonating with it very much because this is how I have approached business. You know, I’m, I’m not a great salesman.

I mean, you are a great salesman and have these relationships. For me, I’m just relying on the relationships and trying to help and, and serve others first. Right? Serve first is what I always say. And what’s beautiful about this is a lot of times these opportunities just come toward you because you’ve already done the job of helping and supporting others, right?

It’s this idea of, like you said, digging the well before you’re thirsty, and it’s just, that’s how it always, like, I wish everybody did it that way. It just l like the internet and the world would be such a better place if we all just tried to see how we can all help each other out. But obviously that’s a pipe dream.

So it actually makes our lives easier as those who want to come from a place of service. It makes their jobs a little easier because it, it actually stands out as somebody who’s just trying to connect, to connect and, and not for any really other purpose than just the, the longevity of that friendship and whatever opportunities may or may not come out of that.

And it might not even be a transactional opportunity. It might be a recommendation. Right? It might be feedback even is valuable and, and all those kinds of things happen when you build those real friendships, like you said. And I love this cuz this tracks with my book Superfans and the reason why we should, you know, build for those experiences and, you know, just a person being a customer’s not the end result.

It’s, it’s them becoming a superfan eventually. One of my mentors, James Schramko and said, you know, we have to stop trying to be so interesting and start getting interested. And I, that’s exactly what you’ve said there. It actually reminds me of Tim Ferris and the way that his book, the Four Hour Work Week came out.

When it came out, I became a bestseller, but nobody knew him. How did that happen? It’s because he and I got this information from somebody who had an account with this. Tim went to all these business and personal development events and he went there with the mission of just learning as much as he could about every other person there and what they were doing, and if he knew somebody that could help them, he would point them in that direction.

If he had some information that could help, he would help them with that to a point where almost every single person you spoke to basically said, Tim, you’ve been so helpful. Like, what can I do for you? Oh, well I have this book I’m writing coming out, and then the book has a good hook and it makes them want to go deeper into that, obviously.

But it, this is exactly the way it should be done. So I’m, I’m glad that you’re here talking about this and, you know, we’re not here to take advantage of people. We are working together with people that that’s exactly what we’re doing. And so the other part about this, the other part of the equation, besides the long tail here, of, of these relationships, the authority that’s built through association.

Can you speak a little bit about that as well to help encourage those who still might, might not be convinced that this is the right way to go about it. You know, building a podcast or a YouTube channel and bringing others on how, how does that help you and your clout essentially, and how do you balance that and how do you use that but not take advantage of that?

Right, because it could be very easy for me to go to a conference and say, oh, you know, I’ve interviewed Tim Ferris and Gary Vanderchuck, like, you should pay attention to me now. Like, I don’t want it to come across that way. So how do you use that and how does that build your clout positively?

Jess Larsen: So there, there’s so many parts in there. First of all, I’ll say I, I typically describe my show as like the Tim Ferris show, but worse. So I’m a fan of what he does. Okay. You know that that authority building is really helpful. You know, one of the things that helps me be calm, and I’d highly recommend for A do YouTube not podcast people, like do YouTube and pull the audio out for your podcast.

You get so much better feedback. It’s after all these years. We finally launched our YouTube show last week for this exact reason. I really do regret not having started like you much earlier, just for the feedback to know if the episodes are serving people, like what people wanna hear more about and these kind of things.

When you have a high frequency, you ever, you know that cliche desperation is a stinky cologne. When you’re interviewing new people all the time, you don’t need to get anybody because you’re gonna meet however many new people next month too. Right. You can just be friendly. It doesn’t need to be transactional. You don’t need to get people.

It lets you like calm down and beat yourself, which also helps with the authority thing. Like I’ve been lucky enough to be introduced to what the world would call fancy people. Okay. I’ve owned a couple different companies with some billionaires. I’ve had multiple billionaires on the show. My one partner, Lindsay Hadley, who we’ve worked together for 20 years, her agency advises celebrities like Hugh Jackman’s wife and Kevin Bacon on their charities and and billionaires. And so I get to go to her than tour events around the world, right? And nothing is more off-putting than someone who shows up and treats them like something different.

Whether it’s in walking ATM machine or whether it’s like you’re, you’re, you’re like an icon, not a human. And like they put up a wall, right? Where if you show up and you’re like, you’re complimentary, but you’re not a fanboy sycophant, you know, and you’re just like a real person who’s genuinely curious and you’re curious about what they wanna talk about, not what you want to talk about as the fan, the potential for relationship goes up so high, right?

So, what I’ll say is by trying to be as much of that as I can on the show, people end up willing to like, call in favors me. Like so many of my best guests are a previous guest who referred their friend to it, who might even be higher profile than them, right? And so as, as I’ve stair stepped up the credibility ladder over time and done favors for these people, like my ability to call someone high profile and get them to do a favor for this high profile person, it’s like, you know, rob Peter to pay Paul kind of circle.

That really goes up. In my day-to-day work with our clients, when I can say, well, you know what the founder of Zoom told me when he was growing Zoom. Whatever comes next In that sentence, a client listens to, right? My own friends actually introduce me differently to people. Like if you think about human survival, It pays well to be friends with the king.

Okay? This is the gospel according to Jess. Okay? So in sheer survival mechanism, like thousands of years ago when your city state might have been invaded and conquered and everyone becomes slaves, or there’s a feminine, people are dying, right? The king has extra food, the king has extra guards. Like if you’re hanging out with him, you kind of get this byproduct of protection. Right?

And I just think like these days we don’t have kings or stuff like this, but like celebrity or wealth, it’s kind of a substitute. And it’s like the way the, the news media has conditioned us to worship those people, even though we shouldn’t, that association becomes a magnet. It’s how we’ve got some of the largest media companies to actually become clients of ours was because of the quality of our guests.

They’re way bigger and important than us, but it’s like, oh, these guests must be of a certain level because those people are willing to come on a show. I don’t know if that’s exactly the question in your answer.

Pat Flynn: Yeah, no, that, that makes sense. For sure. So it just kind of happens naturally, right? You’re not forcing the fact that you have these connections out with others.

They just kind of, you can bring those things up in conversation cuz those are real conversations you’ve had. I mean, do you display like your top guests on your website? I mean, I think that’s, yeah, you kind of do that. You kind of have to do that. You should do that, right?

Jess Larsen: Yeah. This is a really interesting balance beam for me, and I think for everyone. So like if you go to JessLarsen.net, I for sure have Danny Glover, Eric Juan, founder of Zoom. Like we, we just had Samara Cohen, she manages 6 trillion for BlackRock. Like her photos going up, right? Yeah. And for me that’s kind of the like, like on a first date, you put your best foot forward.

You know what I mean? Where I feel like I really have to watch myself is my innate personality that likes the spotlight. That would like to be a big deal. I really have to ratchet that in because, you know, am I name dropping, you know, the CEO of this billion dollar tech fund for me? Or is it because it’s actually gonna help the person I’m talking to take the lesson more seriously?

And kind of every time that I’m like, oh no, it’s for me so that I can feel important, like I know I need to not say it. And I can’t say I always edit myself, but like that’s my rule is like, am I telling the story for me or am I telling the story for them? And as much as possible, I, I try to only tell stories for them.

I don’t always do a good job because I’m like everyone else. I, I hope people call me pretty, you know what I mean?

Pat Flynn: Yeah. No, that, that, that’s really helpful, Justin. I appreciate that insight. You had mentioned YouTube and podcasting. You had and have an audio podcast obviously, and you’ve just launched your YouTube channel to support the podcast.

What was all entailed in that, and I, I want to talk about this cuz we’re all at this sort of interesting inflection point when it comes to podcasting and how video relates to that now and YouTube coming on the spot is, is is gonna be a big supporter of podcasting and even showcase it and probably be, if not already, the biggest player in podcasting.

Cuz most people who actually consume podcasts are watching the videos of those podcasts on YouTube. And YouTube has the, the reach and the algorithm and and such. So I think it’s smart to be there. Are you redoing how you’ve, like, create the podcast specific to be video centric now? Or like, I’m just curious about your process and, and thoughts around, you know, now that there’s video involved.

Jess Larsen: Well, we, we built this studio, right, and I upgraded cameras and things like that so that it would try to be set apart from the thousand other Zoom call podcasts on YouTube. Like anything to differentiate like, differentiated in a valuable way is kind of the name of the game according to me, right? And so, you know, tried to up upgrade some quality like that.

But we know that human decision making is not based on logic there. That there’s a book in 1997 called [inaudible], where they first figured out that decisions after the frontal lobe, like the logic layer part of the brain goes back and forth that it’s the limbic system that lights up, call it like the emotional judge.

It say, you know how I feel about that logic? That’s how humans make decisions. So if you’re trying to influence humans to make any kind of decision, we need to have good logic and we need to have good emotion associated with that logic for them to make the decision. Like how many people listening today know they should work out for an hour and drink eight glasses of water and don’t, it’s not knowing what to do, right?

So in my opinion, video is the number one medium besides being in person. Video is the number one medium for creating an emotional effect. And so the fact that you can record once on here, like, so our clients at Greystoke Network, we have them record on the software, like we’re on Squadcast today, right? I know you’re an advisor over there.

We record here and then we strip out the audio so that anybody who can, wants to listen to it while they’re driving, wants to listen to it while they’re at gym, while walking, the dog, multitasking, doing the dishes, right? They’ve got that. But we put the, the long one on YouTube and we cut medium length clips and we cut some shorts for YouTube shorts and TikTok and Instagram reels and LinkedIn video and whatever the next one that comes out.

Right, and the fact that that one hour we turn into at least six, maybe up to 15 clips, and it gets posted across these different networks. I mean, it’s, it’s easily, you know, one hour a week turns into over a hundred posts a month. And when you think about like the law of familiarity of like humans, back to human survival instinct, the unknown is not a great place for survival.

Right, and so the more we become familiar, the more we can become comfortable, the more, the higher the likelihood we could be influenced. And so being able to show up all these places in their life, keeping out the frequency, but also getting the short reminder of like maybe the 30 second Short leads them to the eight minute clip that leads them to the full length episode. And a again, YouTube has so much better analytics for trying to become a better version of myself, trying to create a better show. That to me, like we have just become, it’s like the YouTube is the center of the hub. And then there’s all these other things that come off it. You know, I’m transcribing my episodes into books, so I’m doing one book called Zero to Billion.

Of the 15 guys who’ve been on the show grew to billion dollar companies. I’m doing one, I think we’re gonna call it Incredible Indians. And it’s just like all the amazing Indian CEOs who’ve been on, we’ll probably do another one that’s just the special ops guys that have been on. So it’s, you know, we hop on Descript, transcribe it up, have somebody proofread the transcription, and there’s so much repurposing, again, back to leverage of busy ceo, busy entrepreneur here today, virtual assistants in the Philippines or South America, something can really take that high profile guest you have and, and create so many products and so many potential connections to have people decide like, oh, this is somebody who’s actually got something good to help me with the problems I’m working on.

I don’t know. How do you see it differently?

Pat Flynn: Yeah, I mean, I, that’s where things are headed and the leverage part of the equation is, is huge because especially with short form video, becoming really at the center of what’s being pushed out there by all these platforms right now.

If you’re going to be spending the time to have a conversation like this with somebody, you want to try to maximize what the can do for you. And so the struggle is video is so much harder to create, you know, good compelling video is so much harder to create, right? It’s, it’s a much lower barrier to entry to get behind a microphone, to not even have cameras on, to be able to have a truly valuable and, and incredible conversation that does all the things we just talked about, build those relationships, could lead to, you know, more things down the road.

And so I’m curious, as far as like with the guests that you’ve had on, they’re not in studio with you, right? They’re they’re still on a recording thing on the internet. I don’t know why I have problems saying that. Like a Squadcast or a Zoom or something. Right, to, to connect with you. And to bring those feelings that we want when people are watching video, like how, how are you hoping to achieve that with that style of, of interview?

Jess Larsen: I do in person programs. And you know, in my case, I’m lucky enough to have a team, so I, I have a filmer comes to it, but originally I didn’t and I went and set up the cameras myself and, you know, show up an hour early to do lights and cameras and get it all ready.

And in the future, like I’m definitely again, looking for differentiation. Like I look at Hot Ones, how it’s become such a phenomenon because it’s like, it’s the talk show, but it’s different that like it, it doesn’t blend in with 50 other shows. Like nobody’s like, oh, was that Hot Ones or was that these other five shows?

Nobody asks that, right. So like what we’re working towards is doing, I think our next experiment is adventure episodes. So I’m a real action sports nut. So we’re gonna be taking certain guests backcountry snowmobile snowboarding, and I, I just went skydiving with a guest and then we did the interview on the beach in Santa Barbara afterwards for my birthday of the summer, it was my birthday present myself.

Right, so we’re gonna do, we’ll do race cars, we’ll do dirt bikes, we’ll do like, go do something cool that that guest wants to do. So I’ll probably have ’em on the show first. The ones I really connect with, and I’m excited about that, that seem like they’d be game for something like, try to say, Hey, you wanna do another one of these?

Let’s go on an adventure and just like film a progressive interview from the truck with all the gear gang out there. Keep the interview going at the top of the mountain, keep the interview going at, at the dinner afterwards. So I think that’s one of the experiments. I’m definitely changing our budgets this year to be able to start flying more places.

And we’ll probably go do, go to New York for a week and try and get a, a morning and afternoon every day for a week and you go to these guys companies or the Bay Area or LA, things like this, you know? So that definitely is in the, in the future. But back to your question of, hey, if I’m on Riverside.Fm, if I’m on Squadcast, if I’m on Zoom, Skype, whatever.

The first thing is good research. If you’ve got a team, have them do it for you, but like watch their previous interview, read their articles. My team lets me know two weeks ahead of time if they have a book. And I try to read, I’m listening at three and a half times on Audible, but I try to listen to their book.

Or at least the majority of it. So they think you actually care about them because you do, cuz you put in some effort to know what’s special about them. It’ll come out in your questions. Right, and at the beginning of every episode, I, I leave at least 5, 10, 15 minutes to shoot the breeze and help them feel comfortable and start off with asking them what’s a win for them and complimenting them on something and being interested in them and letting them ask as many questions as they want before the interview starts, until they’re actually like come to the conclusion like, oh, this isn’t gonna be gotcha journalism where he might make me look bad, like he actually wants me to look good. You know? And then the other secret is only put people on you really want to hear from.

One of my clients, Bloomberg, gave me some hard news a couple years ago and he said, Jess, I think your show’s gotten worse. I was like, Oh yeah? And he’s like, yeah, you just seem bored. And he was like, Ooh. Oh wow. He’s right. Because we, you know, we used to have so many people asking to be on the show, and I was saying, yes to easy.

And then I get somebody on and they just weren’t, they just weren’t of the caliber I was super interested in, in their experience. I, I was super interested in people who had a higher level of experience and so we got way more picky about who was on the show and, and we started reaching for much higher guests where your probability of getting say yes goes down.

And so we had to start reaching out to way more guests because I was going for higher level of people I like really, really wanted to know. And then it was easy to be curios. It was easy to be genuinely super student minded, humble, hanging on there every word because , I wasn’t faking it. I’m like, I really was wanting to know, you know, I’ve had 3 million downloads on my podcast.

You’ve had over 70 million. Like I wanna know everything you’ve got to say about podcasting. I was so stoked to have Pat Flynn on my podcast. You know?

Pat Flynn: Man, this is gonna be mandatory listening for anybody who has a podcast, to be honest. I mean, I think that this is just, the approach is so, it’s, it’s not even, it’s what it should be.

And I think if everybody approached their shows in this way because podcasting as big as it’s become, it’s it, it has started to reach to the point that like blogging took when everybody had a blog and everybody was just starting to, I mean, blogging got to this point where you could set up an RSS feed connected to another website and literally, rip and ship, right?

And it just, the value was gone. And so to have that reminder, I mean, kudos to whoever that was that told you your show was starting to suck cuz that kind of woke you up a little bit.

Jess Larsen: Let’s call him out. Mark Taylor. Mark Taylor. He’s not at Bloomberg anymore, so he’s not gonna get in trouble.

Pat Flynn: We, we need, we need more Mark Taylors in our lives, you know, to just tell us like, Hey, like it’s not great anymore.

And I think inherently what you did was go, well, let me go back to why I wanted to do this in the first place. And I think we often forget our why. When it comes to what we’re creating, because we just get so caught up in everything. So have this be a gentle reminder for all of you to, you know, remember your why and, and maybe find a Mark Taylor in your life to, you know, tell you the, the truth when you need it sometimes.

What might be your, your last bit of advice here for everybody who’s listening, who maybe they have a podcast or some sort of connection to other people through an interview format, on a blog, a podcast, YouTube channel, whatever. And they’re just not seeing results. They’re not, they’re not having fun with it anymore, and they often feel like, I can’t get these people who I want on my show cuz I’m a nobody.

What would you say to that person?

Jess Larsen: I would say it means you’re not good enough and that’s okay. Because none of us are good enough to be at the level we’re trying to get to or we’d be there already. And to become a student. You know, Epictetus and Stoicism says it’s very hard for a man to learn something he thinks he already knows. If we become a student and get into deep humility and we pick the people who have the show and the results that we think we wanna have, and we get much more interested in what we must not know because we don’t have the results they have and get into full-time learner mode and, you know, read Richard Koch’s book The 80/20 Principle about the very few things in life that make the biggest difference. And get obsessed with the idea it’s okay I’m not good enough, and if I do enough meaningful repetitions, I’m gonna throw out another book of favorite, The Talent Code by Daniel Coyle about how experts become experts. And create your own talent code system for how I’m gonna get enough meaningful repetitions in outside of my comfort zone, that I actually get better, that I can qualify for that guest who’s just a little bit better.

And if you constantly think what’s in it for them? And your interviews express what’s in it for them. And we’re trying to make them look good, not ourselves, look good. And we’re doing them the favor. It becomes easier for them to refer us to somebody who’s just a little higher on the food chain than them.

That’s probably more than one piece of advice, but I wanted to get those in.

Pat Flynn: No, that’s great. And, and thank you for those resources as well. I’ve heard a lot about Talent Code and I’ll have to dive into that next, actually, I’m looking for my book list for 2023 here at the end of the year of 2022 right now.

So thank you for that. And thank you just for coming on. I, I appreciate you so much. Your Innovation in Leadership podcast is definitely a must listen, and, and I love how you described it. Because, you know, I love Tim Ferris’s show, but you know, I love different perspectives as well, and with these people that you have on in, in your interview style.

I mean, I knew it when I was on your show with Matt. Just the way that you approach the, the interview shows, they’re just very friendly and it’s like I’m in the room with you when listening to one of your podcasts. So thank you for that. And thank you for sharing what’s going on. And like, if people wanted to follow you, you know, there’s JessLarsen.net obviously. And the podcast that people should listen to.

But where on YouTube might people be able to find you because that’s the new thing.

Jess Larsen: Yeah, it’s just @JessLarsenShow, you know, like YouTube.com/@JessLarsenShow is, is the URL there.

Pat Flynn: Perfect. And anywhere else, any other resources you wanna offer for, for people before we go?

Jess Larsen: Those would probably be my top two. I mean, connect, LinkedIn. I’m, I really like LinkedIn. I’d love to connect to anybody who wants to.

Pat Flynn: Awesome. Well, just thank you so much for this opportunity to chat with you. I look forward to listening to your show more and just everybody should go listen to your podcast right now. Thanks man.

Jess Larsen: Thanks so much.

Pat Flynn: All right. I hope you enjoyed that interview with Jess. Jess is absolutely amazing. I love what he’s doing. He’s doing it right, starting a podcast, not just for the growth that can happen with his show and getting more eyeballs on his brand, but the true real connections and actual friendships that you can make.

And Jess and I are now friends as well, and I’m sure we’re gonna connect again in the future. Speaking of connections, we first connected on his podcast, the Innovation in Leadership podcast with Jess Larsen. Definitely needs to check out my guest spot on his show. That was super fun. We’ll link to it in the show notes like we always do.

SmartPassiveIncome.com/session651. Again, SmartPassiveIncome.com/session651. Thank you so much for listening in today. I appreciate you and look out for the next episode because we have a fun Friday episode coming your way, as we often do, and then another awesome interview coming next week for you.

So thank you so much. I appreciate you. If I haven’t said it already, keep being awesome and happy New Year. Let’s make 2023 awesome. I’ll see you soon. Cheers.
Thanks for listening to the Smart Passive Income Podcast at SmartPassiveIncome.com. I’m your host, Pat Flynn. Our senior producer is David Grabowski. Our series producer is Paul Grigoras, and our executive producer is Matt Gartland. Sound editing by Duncan Brown. The Smart Passive Income Podcast is a production of SPI Media. We’ll catch you in the next session.


Smart Passive Income Podcast

with Pat Flynn

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