But first!

We’d like to welcome and thank our newest sponsor Precision Pro for presenting today’s newsletter.

A lot of Jon’s material is about how to play smarter golf. One thing that has personally helped me play smarter golf is using Precision Pro’s Titan Elite which gives me front, middle and back distances on my iron shots.

Should I be pulling at a pin that’s 3 yards off the back left of the green? Absolutely not (which I know from reading Jon’s book!), and with the Titan, I can find the middle number, hit a normal shot and take my 4.

Of course, because I am a golfer and an idiot, I usually don’t take my middle number and play for par. But with Precision Pro, the option for me to play smart, good golf is at least there, right in front of my face.

Maybe someday I’ll even take advantage of it.

OK, onto the Q&A.

---

Q&A: Jon Sherman

KP: We're sitting here at TGL. Very normal sport day.

Jon: Exciting match. It was good. I had a good time. I enjoyed it.

KP: One of the things we were talking about earlier is just the idea of how people make money online by creating content, and specifically for us, golf content. So as much as you're comfortable sharing, how do you generate revenue for you and your family and your business online?

Jon: I've told you this before. I think I realized early on, I've been doing this for a decade now, that in order to succeed, you have to be good at selling [either] your own product or somebody else's. I'm a fairly risk averse person, so I've tried to do both.

Selling someone else's product could be, obviously, an advertising relationship, affiliate, or being a reseller. I've resold launch monitors and other products that I've liked directly to my audience. That's worked well at times. But the most important thing was creating my own product, which was writing my book and my second book, having a digital course.

So that gave me a bit more control over my destiny and made me feel more comfortable giving out free information so that if people like it, they can support me, and more importantly, their golf game. It's felt like a very even, equal exchange for both sides.

I think that's the hardest equation for anyone to solve.

It's like, if I keep giving away this information and this content for free, how do I make a living off of it? And some people, it's very complicated for them, and they aren't able to do it. I think, to be quite honest with you, it's easier for me in the game improvement category. It just lends itself to commerce more easily. But I've tried to be responsible about that and not push crappy products on people that I know aren't going to make them better.

KP: Was there a point when you realized in writing for Foundations, Man, I think I have something here just in terms of the feedback you were getting? What was the moment where you realized, Hey, this is a thing?

Jon: The book was really a compilation of me writing about game improvement for six or seven years. And I was like, “All right, I'm going to take all my best concepts. Then I know it worked well on Twitter, my newsletter, my website, and then some new stuff and put it together.”

So as I was writing the book, I was very confident. In my head, I'm like, “I think I'm going to write one of the best game improvement books ever. I'm going to give people so much value that when they're done with this thing, they're going to be like, ‘Wow, I now have multiple options to get better.’”

So I felt confident while I was writing it. Then the day it was released, I remember calling my dad and being like, “This is going to be a horrible failure. No one's going to read this.”

Ed. note: The creative process!

So luckily, after a couple of weeks, I had some pretty good evidence that not only was it selling well, but that the initial reviews were very positive. The thing for me is that if you gave me $20, $25, whatever way you purchased it, I just really wanted to make sure that you were going to get way more than that in value.

That was something I obsessed about while I wrote it, was just giving people value.

KP: What did you want to be when you were 14 years old?

Jon: I always wanted to have my own business. I didn't know what it was, but I was the kid who used to sell candy out of his locker in seventh grade. We used to sell Gatorades on the golf course. So I always wanted to be an entrepreneur and do something in the business world, but I had no idea it would be in golf.

KP: What was the leap from that 14-year-old kid into starting your own business in the golf media product space?

Jon: I think it took me a while to find what I was good at professionally. I worked at Google for a while, which was very cool. I tried starting a business with my brother that didn't work out when I was younger. I worked with my dad for a while, and he has his own business and [learned] from him.

But at some point, I realized I thought I had some good ideas with golf, and I quickly fell flat on my face when I first started my site, and I almost gave up after a year when I realized literally how hard it was not only to get people's attention, but to also monetize it. It took a lot of learning how to be okay with failing and things not working and changing ideas. I don't think I could have done that as well if I hadn't had my prior experience in the business world.

KP: I'm sure people ask you, they ask all of us, “How do I get into this?” What's your best advice? What do you tell people?

Jon: The number one thing, James Clear calls it the Valley of Despair in his book Atomic Habits. But I always tell people, If you're not passionate and have a deep interest in what you're trying to do, you will give up after three or four months because that initial excitement will wear off, and then you'll be faced with the cold hard silence of the Internet, of people just not caring about what you do.

And that hit me for years. I mean, I get some responses, but the thing that kept me going was I was genuinely interested in helping people get better at golf, and I would just literally be thinking about it all day long.

So whenever people come to me about starting a podcast or how do you do this? I'm like, “You got to have something different to say, and you have to really care about it. Most people won't care in the beginning, and you have to find a way to make them care. And you can only do that, I think, if you have a deep passion and hopefully expertise about the topic you're going to cover.

KP: Where did that desire to see people's games and maybe even lives improve come from? Where does that emanate from?

Jon: I love golf, and I really struggled for a long time about feeling like I was not playing to the level I should be and not enjoying the game. And I would see that in other golfers.

I think my parents instilled in me a desire to just want to help people, and I just always felt good about giving a tip to someone on the course and seeing them spark an idea or have them enjoy their round more.

So I think my baseline desire is that I love helping other golfers enjoy the game more and get better. That's my cornerstone of what I do. So me getting messages from someone who read the book or whatever, a tweet I sent out, that keeps me going because inevitably, when you do this for a living, again, there's that cold, hard silence of the internet at times.

And you're like, “What am I doing here?” That's my north star. I know if I'm helping people, that makes me feel good about what I'm doing.

KP: What's the most common question that you get from people?

Jon: In regards to the golf part, [it’s] “How did you become a scratch golfer?”

KP: There's a great part in Four Foundations, and I think you've talked about this elsewhere, about how you yourself used to be a golfer that you didn't enjoy being around. What was the moment that that flipped for you to where you became more accepting of yourself on the golf course? Because we played in Vegas, it was a ton of fun. I think you view golf differently now, so what was that inflection point for you?

Jon: You're probably thinking about this. I had a moment with my dad in my early 20s where I had a horrible outburst on the golf course, and he just walked off the course in disgust.

It was like a rock bottom moment for my relationship with golf. And I was like, “I can't play this game if I'm just going to be angry at myself and think about the scores I'm shooting.” At that time, I really didn't have much time to practice or play, so it just felt silly to me. So I think that was a moment when I realized at that time, I couldn't play or practice much so I just had to enjoy the time I had on the course.

Then when I did get the opportunity to play and practice more, I could obviously adjust my expectations. But I still, as much as I compete and want to play well and shoot low scores, I still want to make sure that at the end of every round I can look back … even when we played in Vegas, I think I topped the opening tee shot. I was just out of sorts all day.

Ed. note: Can confirm.

Jon: You know what? The old me would have lost my mind, but I'm like, “You know what? We're out here with new friends on an amazing golf course, the sun shining.” Sometimes I have to dig deep to find that perspective. But as much as I want to play well, I still have to remember, “I still want to enjoy playing golf,” which is hard to do for all of us at times.

KP: How aware are you of ... I mean, we are both in some ways public figures. How aware are you of the fact that other people are watching you to see if you're living out what you're telling them to do?

Jon: I think that last year was a struggle for me, to be honest. I'll play in certain tournaments. My best day ever in a tournament was when I won my U.S. Mid Am qualifier, I played with two guys in my group who were listeners to my podcast.

It was fun to live up to what they thought of me. But as time went on, I think I've struggled a little bit more for that. This year, one of my goals is to put that behind me and realize that if anyone is a fan of the content I'm putting out there, then they're probably rooting for me to be that type of player. It's great to shoot low scores, but I also want to adhere to the principles and ... I want to hold myself accountable to what I'm asking of other golfers is really my main focus.

A lot of the times in golf, we struggle with vanity, and I have to look past all that bullshit, to be honest.

KP: What's the hardest part about being a coach of a tour player? [Jon coaches Mackenzie Hughes].

Jon: I think the hardest thing working with Mac Hughes is we put a lot of time and effort into putting him in the best place possible. It's so fun to watch him play well and have really nice finishes. But we get a lot of satisfaction when he can still get a decent result when he's struggling.

But it's really hard. There's many slumps he goes through. And the type of relationship we have, it's hard for me not to feel that, too. And I'm trying to get better at that. I think in the beginning, it was a struggle for me because I hadn't coached at that level before.

But yeah, being a professional golfer is one of the hardest jobs I've ever seen, and just dealing with the fluctuations in performance levels and knowing your job is not secure. It's sometimes hard for me to absorb all of that and make sure that he can be in the best place possible. But that's my job, and I love doing it.

It's one of my favorite things that I get to do.

KP: Okay, last one. What are your inputs from a business standpoint? What are you taking in in terms of people you're learning from, podcasts you're listening to, stuff like that?

Jon: I don't consume as much content as people would assume. I have tried to remain willfully ignorant on certain issues. Not to say I haven't learned from certain people. The only podcast I really listen to a lot because I really don't drive a lot anymore is My First Million. I think these guys are really smart with coming up with entrepreneurial ideas.

Sometimes it'll spark a creative idea in my head. But yeah, I think one of my inspirations for my book was when I read Atomic Habits from James Clear, I'm like, “Man, I just want to write something so clear and simple and actionable.”

The Psychology of Money was another book by Morgan Housel, who is a phenomenon. If I can write so simply and effectively and not overbear people with too much extraneous information, then I know people will get better.

So I've just tried to keep things incredibly simple and actionable are my two north stars. That's been really hard to do.

KP: We were talking earlier about coming up with creative ideas, and you just mentioned things that spark creative ideas. Where do you go when you need a new idea? Do you go on a walk? What's the thing where you're like, “Okay, I'm generating ideas right now.”

Jon: Playing golf. Every time I play, I'll either see something in another golfer's game or something will happen to me … luckily, it's a fun part of my business that I actually have to be playing enough golf and competing to come up with these ideas.

But yeah, I need to get bored and wander, so I walk every day. Again, I don't really consume a lot of golf content because I want to be somewhat original in my thoughts, so it's really based on my experiences.

I have learned from some other coaches, obviously. I get a lot of great ideas in the shower, which sounds ridiculous. You have to remove yourself from the stimulation of technology, which is hard for me with social media and everything. But yeah, a lot of my best ideas come from when I'm just letting my mind wander, and that's hard to get into. To be honest, it's getting harder and harder for me to do that as time goes on. It was easier in the beginning, and I wonder if that's the toll of doing this for a whole decade.

But I'll, again, hit a golf shot, have a thought on the course, and I'm like, “Oh, okay, there's a kernel of an idea there.” I'll think about it for about three or four days. I write it in my head, and then it comes out on a podcast or when I write it on a newsletter. So that's been my process where there'll be a spark. I let it fester for a while. I write in my head, which I don't know if other people do. I usually don't write it down initially, and then it becomes something after a few days.

KP: Do you ever forget them?

Jon: Usually not. I keep a running list of them on my phone. Okay, so you capture it that way. If it's good, I'll document the initial idea, and then I'll let it run around in my head. And then if it becomes something, let's say, a week later, then I'm like, “All right, this is probably worth a tweet or an article or something.” And then I see people's response to it, and then I'm like, “Okay, then I got to do more of that.” And that's been my creative process the whole way.