Digital Social Hour
Why Most Business Coaches Get It Wrong | Brandon Bowsky DSH #1379
Wed, 21 May 2025
🚨 Why do most business coaches get it wrong? Tune in now to find out on Digital Social Hour with Sean Kelly! 🚀 This episode is packed with valuable insights as Brandon Boskey shares why so many coaches fail to deliver real results, the dangers of bad advice, and how he's redefining the coaching game by focusing on impact instead of quick wins. 💡 From his early challenges to building a thriving community of entrepreneurs, Brandon opens up about his journey, the importance of coaching on what you KNOW, and why authenticity is the ultimate game-changer. 🗝️ Plus, hear hilarious and eye-opening stories about life, dating, and the lessons learned along the way. 💼 Whether you're an aspiring entrepreneur, a seasoned business owner, or just curious about the coaching world, this episode is a must-watch. Join the conversation and uncover insider secrets that can transform your mindset and business. Watch now and subscribe for more insider stories on the Digital Social Hour with Sean Kelly! 📺✨ Don’t miss out—hit that subscribe button and stay tuned! 🔥 CHAPTERS: 00:00 - Intro 01:22 - Business Coaching Strategies 05:01 - Importance of Rest and Recovery 07:31 - International Business Insights 08:17 - Finding a Good Business Partner 11:17 - Finding a Good Business Partner (Part 2) 13:39 - Finding a Good Business Partner (Part 3) 16:31 - First Date Etiquette: Who Pays? 19:39 - Overcoming Communication Issues 23:09 - Discussing Parenthood: Do You Want Kids? 23:40 - Planning Your Next Steps 26:00 - Dealing with Crazy People 28:46 - Lessons from Lawsuits and Friendships 31:12 - Best Cities for Living 36:10 - Reflecting on Retirement Fulfillment 38:57 - Money vs. Fulfillment: A Discussion 41:19 - Where to Find Bowsky APPLY TO BE ON THE PODCAST: https://www.digitalsocialhour.com/application BUSINESS INQUIRIES/SPONSORS: [email protected] GUEST: Brandon Bowsky https://www.instagram.com/bowsky/ SPONSORS: SAMRBOSA: https://sambrosa.com/ LISTEN ON: Apple Podcasts: https://podcasts.apple.com/us/podcast/digital-social-hour/id1676846015 Spotify: https://open.spotify.com/show/5Jn7LXarRlI8Hc0GtTn759 Sean Kelly Instagram: https://www.instagram.com/seanmikekelly/ The views and opinions expressed by guests on Digital Social Hour are solely those of the individuals appearing on the podcast and do not necessarily reflect the views or opinions of the host, Sean Kelly, or the Digital Social Hour team. While we encourage open and honest conversations, Sean Kelly is not legally responsible for any statements, claims, or opinions made by guests during the show. Listeners are encouraged to form their own opinions and consult professionals for advice where appropriate. Content on this podcast is for entertainment and informational purposes only and should not be considered legal, medical, financial, or professional advice. #growyourcoachingbusiness #howtostartacoachingbusiness #businesscoach #motivationalspeech #businesscoaching
Chapter 1: Why do most business coaches fail?
No matter what. I used to go on like four dates a week to the same restaurant when I was like in my looking for love phase and it was just qualify, qualify, qualify, qualify, qualify. And I knew the food was going to be good every day. Yeah. And so I did that for years. The staff didn't snitch on you? There was one time.
So the worst thing that's ever happened is, oh my God, it's so good to see you again, but not to me, to the girl.
No. All right, guys. Third time's a charm. Brandon Boski back on the show. Coming straight off the bathroom. A little experiment yesterday. Yeah, it was fun. It sounds way worse than it is. Yeah, but basically, I had an event last night, guys, and this man was in the bathroom for how long? It was almost two hours.
Two hours. Giving a little lecture, right? Well, it started off with a guy that was like a dude that was in my Discord the past couple of years. And then out of nowhere, he had like a few friends with him and just... Hey, bro, so good to meet you. Can I get some advice? I was like, yeah, sure. And then the friend needed advice. The friend needed advice. Friend needed advice.
And I didn't realize how long it was. I got a cigar from the bathroom attendant dude and you know, whatever. So I'm sitting here and I didn't realize how usually I smoke a cigar in my backyard. It's like half an hour.
Yeah.
It's like two hours. It's like the biggest cigar I've ever smoked. I mean, it was crazy. And so about an hour in, there's people that have gone to the bathroom twice. Like they broke the seal and they had to go again. They're like, you're still giving a lecture. You're still giving a sermon. It was crazy. pretty wild. I could tell you're passionate about teaching people though. Yeah.
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Chapter 2: What are the key qualities of a good business partner?
I mean, that's, that's the plan this year is build the community, really go all in on that. Um, the few thousand people that are in it already grandfathered in, but everything else is paywall and just lots of business coaching, lots of advice, lots of helping people grow. And that's kind of what I want to do with my life now.
Well, you've done the hard part. Cause there's a lot of coaches that don't have the results yet, but you actually have results. So
Yeah, I've been blessed. I've had really good teams. I've had really good opportunities and I worked really hard. But I think that you hit a nail on the head. Most people telling you about the stuff, they've never done the stuff. And I think it's a big problem and it leads to a lot of bad advice and a lot of people failing that could have otherwise been successful if they had good advice.
Chapter 3: What are the dangers of bad coaching advice?
Chapter 4: How important is rest and recovery for entrepreneurs?
Yeah.
It's like two hours. It's like the biggest cigar I've ever smoked. I mean, it was crazy. And so about an hour in, there's people that have gone to the bathroom twice. Like they broke the seal and they had to go again. They're like, you're still giving a lecture. You're still giving a sermon. It was crazy. pretty wild. I could tell you're passionate about teaching people though. Yeah.
I mean, that's, that's the plan this year is build the community, really go all in on that. Um, the few thousand people that are in it already grandfathered in, but everything else is paywall and just lots of business coaching, lots of advice, lots of helping people grow. And that's kind of what I want to do with my life now.
Well, you've done the hard part. Cause there's a lot of coaches that don't have the results yet, but you actually have results. So
Yeah, I've been blessed. I've had really good teams. I've had really good opportunities and I worked really hard. But I think that you hit a nail on the head. Most people telling you about the stuff, they've never done the stuff. And I think it's a big problem and it leads to a lot of bad advice and a lot of people failing that could have otherwise been successful if they had good advice.
And for me, it's not like I don't want to trade my time for money. I have a lot of friends that do that, that do the, oh, 10, 20K an hour coaching stuff. I've done consulting for like 10, 25 grand an hour, depending on the subject matter. But That's not really what I want to do.
I'd rather charge people a few hundred bucks or a couple hundred bucks a month to be in a group session where everybody can benefit. Because when I used to do one-on-one coaching, what I found, this was like 21, 22. What I found was everybody asks the same questions. Eventually they get into like niche down stuff. But at the beginning, everyone asks the same shit.
So the very basic stuff, if I get asked that and I have a thousand people listening or I have one person listening, it is the exact same output for me. I don't have to do any extra work, but now I can impact a thousand people instead of one.
Right. That makes a lot of sense. I also like that you coach on what you specialize in because a lot of people coach these fads like dropshipping or whatever and trends and they know that shit doesn't work, bro. You know what I mean? Oh, yeah, 100%. I mean, they know that they're scamming people. Pretty much, because by the time they're teaching it, it doesn't work.
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Chapter 5: What lessons can be learned from lawsuits and friendships?
Chapter 6: How do you navigate dating and relationships while building a business?
Yeah. I mean, I'm okay with people that have high revenue. We were talking about this last night in the bathroom. Yeah. This sounds so bad.
Uh, I'm okay with people that are like rev, rev, rev, but a lot of people that are chasing revenue never make money because they don't understand that eventually you hit diminishing returns and it starts to actually lose you money to keep growing and growing and growing. And if there's no exitable, uh, company there, there's no like potential for getting out of it. You should focus on profit.
Everybody has this dream of selling a company. Most companies aren't saleable.
Hmm.
Like they're not things that people want to purchase. So all these people that are like, I'm going to sell my company. It's like for fucking what you wash cars, bro. Nobody's buying your car wash business unless it's a PPF company and you've got 10,000 clients and they're like, yeah, we got this new PPF. It takes three seconds to apply and we can sell it to everybody, you know? Yeah.
And those strategic acquisitions, they never happen for average shows. So people live in these pipe dreams.
Would you ever get into retail or brick and mortar, like physical stuff?
I have done some in the past. I failed miserably with a biohacking gym back in 2020 during COVID. Lost over a million dollars on that. Was that just bad timing, you think, though? I think it was bad timing, and I didn't try. Mm-mm.
You know, I think to be successful, you have to be really virtually all in or close to all in on something where you've got to have multiple projects, but some of them run autonomously or semi-autonomously. And then you can focus. Yeah. I was not focused. I was like, life was collapsing. COVID happened, lost millions of dollars. And I'm just bleeding more money in this gym every month.
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Chapter 7: What is the impact of fulfillment versus money in business?
I said hi to a few friends, said hi to you, hung out for a few minutes, but then happened to take a piss and get a cigar. And next thing I know, I'm giving a lecture to a bunch of young kids. I was wondering where you went. But that was actually the most impactful thing that I've done in a long time. I left that the happiest that I had felt in a very long time. Wow.
To the point where I texted my entire core team at two of my companies and was like,
yo i feel so much better about this mission and this next phase of evolution now as like me as a person yeah that's so fascinating because you made tens of millions of dollars but just inspiring 10 people in a bathroom is like it wasn't even 10 it was like well maybe with the people that walked in and out but you know it was like four kids oh wow these were these are 18 to 23 year old kids that are all doing seven figures or high six figures and i'm just like dude
I have siblings that are your age, a little older, and they are not there. I'm sitting here like, do not give money to women. All the typical stuff that I've ever said. Here's all the advice. Hope you're voice memoing this. So you were giving dating advice too? I gave all advice. I was like, do not fucking date until you are 25, 26.
Make sure they're 25, 26, because that's when they realize life sucks.
Damn, 25, 26 is pretty late to start dating.
Well, I mean, at their age, they could take so, okay. I'm not a Gary Vee patience guy, but they have a lot of time. They're very young. Like these kids are over 10 years younger than me. And one thing that I did that was messed up early on was I was chasing love and money and success and internal fulfillment.
Hmm.
You can't have all the things at once. If you're going from zero, you have to pick one at a time and check the boxes because you're not going to be focused on accomplishing any one goal. It's just like anything in life. Yeah.
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Chapter 8: How do you find happiness while pursuing success?
And then the other one I was like, I don't know. It was never really worked out timing wise. Could you date a woman that was broke? Yeah. Oh my God. Do most of the women that I have dated have not been like rich by any means. I don't think I've actually ever dated a rich woman. Interesting. Yeah. So that doesn't matter to you? No. Who cares? So what do you prioritize? Who they are as a person.
And then do they do something that brings them fulfillment? Okay. Like it's really important that you have things that you like to do like this. And your wife gives you the freedom to do this. She could be like, I don't like that you do that. Right. And then that could create a conflict. But she's very supportive. You guys have very good relationship and good relationship dynamic.
That's what it's all about. Do you have a thing you like? Does she have a thing she likes? And then do you guys together like your life? Are you happy alone? And then are you happy together? Most people struggle to be happy alone. True.
I mean, I am most people. I'm an only child, so I think I had to figure it out quicker than most. Yeah. Because I was on my own a lot. But I know some of my friends struggle to just be alone in a room. Dude, I am one of those people.
I mean, I have people around me all the time. Chef, staff, team. Yeah. I always have people around, so I'm not all alone, but I'm not like a very good... I can't go on vacations alone and have a good time. No, hell no. Oh, this is cool to look at. But some people love that. Really? International travel alone. Yeah, I have some... One of my exes was like, you need to travel alone.
I'm like, that sounds miserable. No, traveling is different for me. Yeah, like I want to... I like the idea of making memories with people because you're going to forget your own memories one day, but somebody can remind you of them. And a friend will tell you like, hey, remember that time we did that thing? And to you, you're like... I forgot we even did that.
But that's their fondest memory with you.
100%.
That's cool. Now, when it comes to buying women's stuff, like material objects, when does that happen for you?
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