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[EO San Diego] The Power of Relationships and Masterminds in Business With Eric Berman

[EO San Diego] The Power of Relationships and Masterminds in Business With Eric Berman

Eric BermanEric Berman is the Founder and Mastermind Leader of Speakeasy Mastermind, a private global community that brings experienced entrepreneurs together for collaboration, strategic problem-solving, and business growth. He is also the Founder and CEO of Brandetize and Celebritize, companies focused on digital marketing and brand visibility for thought leaders, consumer brands, and influencers. Prior to these ventures, Eric co-founded CollegeClub.com, an early large-scale online community, where he held executive roles during its rapid growth. Additionally, he consults for companies, works with venture capitalists, and hosts the Inside the Speakeasy podcast.

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Here’s a glimpse of what you’ll learn:

  • [04:20] How offering free services jump-started Eric Berman’s agency  
  • [05:19] Four criteria Eric uses before entering revenue-share deals 
  • [13:10] Turning informal masterminds into a scalable business model 
  • [17:12] Why SOPs are crucial but hard for entrepreneurs to adopt  
  • [20:28] How early business lessons shaped Eric’s entrepreneurial mindset  
  • [33:46] Why building communities is Eric’s lifelong business passion  
  • [38:45] Partnering with influencers to build scalable, AI-resistant businesses
  • [43:28] Tips for structuring win-win partnerships with influencers

In this episode…

Strong businesses rarely win on tactics alone. What separates the companies that endure from those that stall is often something harder to quantify but easier to feel once it’s missing. So what really gives entrepreneurs a lasting edge when markets shift, tools change, and competition intensifies?

Drawing on decades of entrepreneurial experience, Eric Berman explains that meaningful relationships outperform tactics in the long run. He highlights how trust, openness, and long-term alignment turn connections into compounding assets rather than transactional exchanges. The result is better decisions, faster growth, and fewer blind spots over time. He also explains how performance-based partnerships and masterminds create accountability while unlocking opportunities that rarely emerge in isolation.

In this episode of the Rising Entrepreneurs Podcast, Dr. Jeremy Weisz sits down with Eric Berman, Founder and Mastermind Leader of Speakeasy Mastermind, to discuss the power of relationships and masterminds in business. They explore how trust-based partnerships drive growth, how masterminds evolve into scalable communities, and why long-term leverage matters more than short-term wins. Eric also shares hard-earned lessons about focus, niche selection, and building businesses through collaboration.

Resources mentioned in this episode:

Special mentions:

Related episodes:

Quotable moments:

  • “Don’t pay me till I make you money, but I want a piece of the action.”
  • “Your network is your net worth. I gotta learn how to say it.”
  • “It’s lonely being an entrepreneur. Sometimes, making these decisions, if you don’t have a partner, these are tough decisions.”
  • “I always look back and say, you can’t take away my experience.”
  • “I get more jazz when I hear the story of two people that connected, and they are doing cool stuff together.”

Action steps:

  1. Invest in high-quality relationships intentionally: Building trust-based connections creates long-term leverage, opening doors to partnerships, insights, and opportunities that transactions alone cannot deliver.
  2. Join or form a mastermind with aligned peers: Surrounding yourself with experienced entrepreneurs provides accountability, diverse perspectives, and faster problem-solving than working in isolation.
  3. Evaluate partnerships before committing: Assessing alignment, trust, numbers, and scalability helps avoid costly mismatches and ensures relationships grow into mutually beneficial collaborations.
  4. Shift from short-term wins to long-term leverage: Prioritizing sustainable relationships and compounding opportunities leads to more resilient businesses and better decision-making over time.
  5. Create environments that encourage openness and trust: Fostering spaces where people can share honestly strengthens collaboration, surfaces better ideas, and accelerates personal and business growth.

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Episode Transcript:

Intro: 00:02

Welcome to the Rising Entrepreneurs Podcast, where we feature top founders and entrepreneurs and their journey. Now let’s get started with the show.

Dr. Jeremy Weisz: 00:12

Dr. Jeremy Weisz, Founder of InspiredInsider.com, where I talk with inspirational entrepreneurs and leaders. Today is no different. I have Eric Berman, Founder of Speakeasymastermind.com, and Brandetize.com, Celebritize.co. And Eric, before I formally introduce you, I always like to point out other episodes of the podcast people should check out. This is kind of a combination of a top giver series like when I meet someone, Eric, I’m like, this person is just a true giver of a human being. And when we first talked, I’m like, I went back to a couple of people like, Eric is amazing and he reminds me a lot.

And which is not shocking of David Gonzales as part of the Top Giver series. And he’s messaged me about you, Aaron Walker, Dan Kuschell, Ian Garlic. I did an AI interview with Joe Polish. It was not Joe Polish, it was his AI clone, actually, but he’s part of the Giver series as well. And also this is part of the top agency series. 

I’ve had a lot of, you know, digital agencies on the podcast talking about their journey. You know, Kevin Hourigan comes to mind. He started an agency. And you know Kevin.

Eric Berman: 01:20

I know Kevin. Yeah. Cool.

Dr. Jeremy Weisz: 01:21

Good people know good people. Kevin’s amazing. He started his agency in 1995. And so he you probably knew each other back then because I know you had an early startup in, in The.com area, but, you know, just one of the nicest human beings. And he talks about the evolution of the agency world, the internet and business since 1995.

So how do you guys know each other?

Eric Berman: 01:46

Through a mastermind. Actually, an agency mastermind.

Dr. Jeremy Weisz: 01:48

There you go. Yeah, it’s.

Dr. Jeremy Weisz: 01:50

All about we’ll get into Speakeasy Mastermind as well, because I know y’all are all about community. So anyways, check out those episodes before we get into it, this episode is brought to you by Rise25. It Rise25. We help businesses connect to their dream relationships and partnerships. We do that by one or an easy button for a company to launch and run a podcast.

We do the strategy, accountability and the full execution number two or an easy button for a company’s gifting. So we make gifting staying top of mind for clients, partners, prospects, even staff. From a culture perspective, simple, easy and affordable. Just give us a list of addresses. We do everything else, and it’s not like you’re like a one off gift. 

 We like to send a campaign of gifts. So think three gifts a year for five years type of thing. So for me and Eric is much the same. The number one thing in my life is relationships. I’m always looking at ways on how I can give to my best relationships, and I found no better way over the past over 15 years to profile the people I admire and share with the world. 

 We’re working on the podcast and send them sweet treats in the mail so you can go to rise25.com or email support@rise25.com. I am really excited to introduce Eric Berman, serial entrepreneur. As I was mentioning, he’s founder of Speakeasy Mastermind. Speakeasy mastermind is a global community of growth minded entrepreneurs. They’re focused on marketing, sales, and business development. 

 He also runs Celebritize. They partner with top influencers to build and scale businesses that monetize their audiences. Right. And he’s going to talk about some examples around even someone with 6 million followers. And what do you do with that? 

 And he’s also CEO of Brandetize, which is a digital marketing agency. They help experts grow their empires through performance based strategies. One of my favorite stories, which hopefully he’ll tell, is one of the ways he started in this, is he offered his services for free. Okay, I love that approach. We’ll talk about it. 

 Over the years they’ve consulted with you, name it, Clickfunnels, Club Med, Phoenix Space, Troy Capital Partners and many, many, many more. So Eric, thanks for joining me.

Eric Berman: 03:59

Wow, that’s an amazing introduction. Thank you so much for having me. I’m excited to be here today.

Dr. Jeremy Weisz: 04:03

It’s just the truth. So why don’t we start off with Speakeasy Mastermind? Because we’re going to kind of go in reverse, right? Yeah. But like it comes to speakeasy mastermind, what you do I’m going to pull up the site.

So if you’re watching the video, you’ll see us poking around there. But talk about Speakeasy Mastermind, what you do there.

Eric Berman: 04:20

Yeah. So I mean, really this actually the quick backstory of that is, is and I’m kind of weaving in all the different worlds I’m playing in, you know, having the agency branding ties. One of my first big clients that I got was Brian Tracy. By that, you sort of teased it by I was a big fan of Brian’s. He’s in the same city of mine in San Diego, and I got introduced to him and he said, I need help with this internet thing.

You know, we’re talking 2001, of course. And and I said, Brian, I can do this. But, you know, I’m not an employee type. I’ve been building companies my whole life. So I’ll do this and don’t pay me till I make you money, but I want a piece of the action. 

 He said, Eric, you’re my kind of guy. I love, I love that kind of personality. Let’s go. So that was a it’s.

Dr. Jeremy Weisz: 04:57

A no brainer offer and delivering value first.

Eric Berman: 05:00

Yeah. Like and I always even encourage people I’m like God it’s such so easy if you have if you have the cojones and the ability to do that like why not if you really know, you could do something pretty quickly. And that’s a whole other. I could spend 20 minutes talking about what to look for and not look for down that path, but we may not have time for that today. So now go.

Dr. Jeremy Weisz: 05:15

Ahead. What were you like? Give me an example of what you mean by that. What to look for now look for.

Eric Berman: 05:19

Because I mean, even in our agency now, we still will partner up in a way which we’re taking a piece of the back end. But the lessons were and we learned this early on when I started doing this and we went beyond Brian Tracy, we just thought, oh, this model worked for everybody. So we just started offering that to everybody and we’re like, oh, this isn’t going to work all the time. And so now we now we essentially say we have four steps before we get married. Brian got married right away, but that was because he had he had the things and I and I already, you know, without even knowing he already had the things and and the four things I look for, I say, you know, I say tell clients, hey, let’s date before we get married.

For things I’m gonna look for before we go all in and be. Performance number one is do we like each other? And that seems obvious, but, you know, I call it the quick cell phone test. When somebody calls your phone or text you, do you get energy or do you basically say, oh my God, I don’t want to talk to the person? So that’s number one. 

 Do you like the number two? Is do you like the product? Like, you know, are you selling stuff that you really get excited about? You know, is it just nonsense and BS, or is it really making an impact out there that you’re going to want to be, you know, really leaning into that matters? Number three. 

 And those are sort of like, sure, those are the obvious, but you really need to think about that. Number three I like to say is do we know the real numbers of the business. Oftentimes you’ll run into somebody like in almost every time they’re trying to sell you. Oh we’re amazing. And you know, we’re doing, you know, X thousand dollars, you know, in business and we’re on pace to do blah, blah, blah. 

 I’m okay. Well let’s see the numbers look like. And oh, you’re bragging about the one month you had that you’re and you’re multiplying by 12. And that’s not your business, which, you know, isn’t necessarily what.

Dr. Jeremy Weisz: 06:48

We’re on a run rate of x, y, z. In that run rate was based off.

Eric Berman: 06:51

What are we really at? Yeah. So so let’s understand you know, where the true numbers are. And then last but not least, can you actually scale it and can you make an impact. So yeah maybe the business is doing well, but do I have the skill set with me and my team to look at somebody and say, you know what, let’s say I have been working on a retainer or small basis.

You’ve been paying me five, ten grand a month. Can I really is it worth me doubling my labor and and and staff? Because I’m going to take we’re at now and really go above and beyond that. And the answer is yes and all those things. Then you can. 

 It’s a lot easier to make that offer and even making it more of a no brainer offer. Once you have that, say, all right, we’re here, we’re at this number, making this number, you know, over the last average of last six months. We’ll just take a piece of what we build. I mean, how does somebody say no to that when you’re like, okay, this is money you wouldn’t have had. So you in or out and don’t pay me until I get you there.

Dr. Jeremy Weisz: 07:37

Each one of those steps is you like I find in my life. Each step I have is because I made a mistake somewhere, and so that gets added in as like a step. So are there any good stories and okay, we have to like each other. We have the product we have. Do you know the numbers and scale it?

What would be a good story? And first of all, I don’t know. Do you have a book coming out on this or anything. Because there should be a book on how do you.

Eric Berman: 08:01

Yeah.

Dr. Jeremy Weisz: 08:02

Do performance marketing. And these are the four steps. You know.

Eric Berman: 08:05

Maybe maybe that’ll be book three. I got two other topics out of that. So I’m actually going to be off next month to work right on my first book through a workshop. And that’s going to be more on kind of the conversation of your net worth. Your net worth is net worth your net worth?

Net. Sorry.

Dr. Jeremy Weisz: 08:19

I always get this wrong.

Eric Berman: 08:21

Your network is your net worth. I gotta learn how to say it before I write a book around that. But yes, that would be sort of the you know, it.

Dr. Jeremy Weisz: 08:25

Just won’t be the title. You’ll have a different.

Eric Berman: 08:27

Title, something around that. But yeah, we could get into that. Going back to your first question, when I’m going to try to slowly close the loop on that and get over there. But, you know, having started working with Brian, Brian Tracy quickly met other thought leaders. One in particular, his name is John Assaraf really well named guru out there as well, who’s also in San Diego.

And we were doing JVs together and he said, hey, Eric, you know, all this the stuff you’re doing with Brian. You know, I’d love to learn what you’re doing. And why don’t we share what we’re doing? Why don’t we get together and just mastermind and and and really just help lift each other up? And that was the first time that I kind of really got exposed to that deep level of, you know, you talk about it, but what does that really mean? 

 And so he said, well, let’s grab Mike Koenigs and Darren Hardy. And, you know, these are all Mike’s. It was a marketing legend. And Darren Hardy, who now he was running success magazine, is now a huge thought leader in his own right. He had written Compound Effect and a bunch of other books and a couple other guys in San Diego. 

 Let’s get to. So we got we had this dinner meeting and, you know, five guys, everybody was was, you know, considered sort of gurus or got paid a lot of money for their time on stages and all that. And we sat out a room, had some dinner and, and we were just opening up the playbook like what worked and what I found interesting in talking to other people since then is the industry we’re playing in. It’s like, wait, so you get people who you’re sort of competing with to get around and share secrets, like, what is that? That seems so weird and foreign. 

 And then you realize this, this, this, the world that, you know, you and I play plan and others. It’s like there’s also there’s a bit of an abundance mindset that, you know, we all have products that are about doing good for consumers, and we’re trying to make make an impact in the world. And if my consumer is going to buy from me, Brian Tracy, well, then why not offer somebody else? And at the end of the day, they just need help. And if my product doesn’t deliver on that, I got my own problems to deal with. 

 But at least let’s serve that client. And so there was never this, this concept of, of of hiding behind your secrets. It was always, let’s get out there and, and let’s be better together and, and and have those conversations. So I, you know, there was five of us that quickly turned to to 8 to 10 to to 15 to 20. And no longer could we have meetings in restaurants because we were getting interrupted about, can I pour you some more water and can I bring you something else? 

 And can I take your order? And we’re like, wait, we’re like in a really good flow state. Can you, like, go away for an hour? And that just felt awkward. So we went back into into houses and offices and, and, and then guests would show up from different cities and say, well, can you, can you do this? 

 You know, in my city over here, and I ignore that for a while. But but really, what the magic was, was the the way about we organize these, these dinners and the flow and the conversations and the meat of the content to really make it worth people’s time to show up month after month. And for me, looking back in hindsight, I realized sometimes we all have a natural skill set that we’re good at and you call it whether it’s the genius matrix and you say, what do you what do you love to do? And you’re good at? You know, sometimes we realize these are just natural to me, but others look at you and say, wow, this person’s a genius in hindsight. 

 And because I’ve been told this and I don’t like to sort of say like, talk about the things I’m great at, this is just what I learned through through conversations is I had a really natural knack for being able to wrangle entrepreneurs. I’m more I happen to be more of the organized entrepreneur, the high follow through entrepreneur. And I think John Assaraf kind of detected that early on and said, Eric, let’s get these. You know, almost like Eric, you organize like it’s almost like he just instinctively knew. And sure enough, I was the guy that always said, all right, let’s go. 

 Like everybody this time, this meeting, who’s in, who’s out. And just it just ended up being my mastermind group by by sort of default to keep it going, that those conversations were so impactful that how much we were learning and growing together about, like, what’s working in your business and can you make an introduction and just knowing this group is there for you. You hear the concept of sometimes you hear the concept. It’s lonely being an entrepreneur. And at first I heard that I’m like, I’m extroverted guy. 

 I’m not lonely. And then I realized what it really meant. Sometimes making these decisions. If you don’t have a partner, these are tough decisions. If you don’t have a certain partner to talk to, you can’t necessarily talk to your employees. 

 You often can’t talk to your significant other. And even when you go out with friends, do you really have permission to talk business with you, out with other friends? Sometimes it’s just like, let’s get together and I’m so exhausted. Let’s just grab a drink and I can’t hear. There’s noise and there’s the game on TV and you know. 

 ET cetera, et cetera. So just realizing that, wow, this it felt special. And I think and I’m sorry, I’m making a long answer to your question. So as I was in agency land and I’ve been in agency land for 20 plus years looking for my next pivot, I started asking myself, what’s next? And I’m like, well, wait a second. 

 Everybody keeps saying, you should do this mastermind in other cities. And I ran some numbers and I’m like, well, wait, okay, well, if I can repeat this formula, this is really interesting business model out there. Obviously there’s other groups out there in this world, and I have been a member of EO Entrepreneur Organization forever who has a successful model. Why couldn’t I take a play a page out of that playbook, keep what I love about EO, and then add all the elements I loved about this and build out something there. And there we have the Speakeasy mastermind was born.

Dr. Jeremy Weisz: 13:24

I do want to touch on a few of these points. And by the way, in the video here, we’re we’re looking at the speakeasy mastermind. I do you know, I was actually listening to you, you were talking to Matt Wolf and Jo Fear. This was several years ago. And they were saying I, you know, they were raving about your event and like it was the best event I’ve been to.

It was, you know, it was great. The people there were amazing. I’m curious how the format has evolved. You know, from that first meeting, you know, you rang, you know, John Assaraf was there and a bunch of other people. How have you refined the format over time?

Eric Berman: 14:00

That’s a great question. And and it was one of the struggles is figuring out really, really how to do a format because it became just sort of natural and organic. People would show up. But there was such familiarity with the people in San Diego that I realized as I expanded, I the first couple of years, it was just really interesting grind. I’m like, oh my God, my mind needs to go to massive SOP mode because it’s not like I can just people naturally understand what I’m talking about.

I have to really give them a playbook. And then what made matters worse is I’m bringing in entrepreneurs to run cities. And once again, I realized quickly that the entrepreneur high follow through skill is lacking in many entrepreneurs. The it goes back to the same point. A lot of entrepreneurs are very good visionary. 

 They’re kind of on the fly. Just throw me in a room and I’ll figure it out kind of thing. And I’m out over here trying to push SOPs and there’s a little bit of a conflict. And that sort of had me initially in the early on, why I even had some cities come and go is I had.

Dr. Jeremy Weisz: 14:55

You know, Mark winters on and then Gino Wickman on separately. And then if people know they wrote Rocket Fuel together and it’s the visionary integrator and maybe everyone needs to take an integrator score or whatever, I’m not sure. I think I think he sold rocket fuel at this point. But yeah, I totally hear what you’re saying. With that.

Eric Berman: 15:17

It was so just learning.

Dr. Jeremy Weisz: 15:19

What it takes.

Eric Berman: 15:20

A different skill set and saying, okay, well, if you are this person, you need to be paired with this other person. Like we can’t launch unless these things are there. So a lot of that stuff sort of happening. But to to your question, how it’s evolved, I think it was just a lot less, hey, I’m going to free flow content this month and we’re going to talk about these topics. And what we used to do is we’d go around the room and everybody sort of takes a turn.

They already knew what to say to, okay, I need to actually have real framework for how these meetings go. You know, first session we have dinner, you know, then we do introductions and then we have a presentation or a topic, and then we have some roundtables, and then we have a hot seat. And then we, you know, do housekeeping. And then it’s like there’s like literally like six sections of our meeting. And I have to rinse and repeat. 

 And as much as you put it out there, you know, sure enough, people still aren’t following the formula. So now I’m like, okay, now I gotta like, fly to San Diego and watch a meeting, or I gotta have somebody look in. It’s just it’s just insane how how it’s these are all obstacles. And when every time I get frustrated and then I immediately I turn around and say, okay, this is good. This is another mode in the business and making it more difficult for others to model what I’m doing because it’s not easy. 

 It’s freaking hard to take that model and just rinse and repeat.

Dr. Jeremy Weisz: 16:26

I’m curious, you mentioned, you know, SOPs, okay. And I feel like sometimes I’m the SOP police, which I, I don’t mind, actually. I’m curious what you use to format them house them? I mean, maybe it goes into kind of the tech stack, but I remember I had the founder of Sweet Process on and we use Sweet Process to just keep in one place. And I want him to come talk about it’s just so important.

I feel like the, you know, standard operating procedures in general. And then I had a client who talked about how do you, you know, put these on hyperdrive, because for me, it’s about productivity. Like if I can, you know, create a process, you know, that could be more productive. So I’m curious, how do you handle the the SOP world?

Eric Berman: 17:12

Yeah. Well, for this business with my city leaders, it’s it’s it’s it’s painful because it goes back to the same avatar like I’ll have I have like a playbook on a Google doc. Does everybody read it and study it. Probably not. They might have.

They might have. They might have glanced at it. It’s just the same routine. They’re going in there and just saying, I’ll figure it out as I go. And I try to show them the playbook. 

 So me Honestly, the playbook is unfortunately, it’s a lot more. I got to really just get on the phone with him and walk him through a few times until they get it. It’s just it’s it’s weird. So technically I do. I mean, to answer your question, it’s technical basis. 

 I have Google Docs, we all use circles, our platform and we refer to that. We have things pinned so they have reference guides. But with my avatar and the leaders I can have playbooks up up the but but you know it’s just it’s like anything else. Like how many entrepreneurs running companies, they all intuitively know they need to build SOPs, but how many of them actually never even go in their own SOPs?

Dr. Jeremy Weisz: 18:06

There’s an accountability for sure. I mean, like, I know how to work out, but I hire a personal trainer because they make sure I do it and I do it right, and I do it harder and more frequently. So I get it. What about from the agency side from brands? What is the tech stack look like there?

What kind of tools and software.

Eric Berman: 18:27

Teams using I believe I mean it’s it’s it’s changed over time obviously from Google Docs into then we went into a sauna for a little while, and now we’re out of that. And now, as far as a lot of SOPs, it’s there’s some on notion and Coda have been two different stacks we’ve used internally. You know, still some of the Google Docs back in various file folders and all that.

Dr. Jeremy Weisz: 18:46

What made you decide to expand? I mean, you have this amazing core group starting in San Diego. Where was the first expansion and why?

Eric Berman: 18:57

You mentioned his name, DG. David Gonzalez over in Austin. So was Alex Mendoza and and Scottsdale and David and Austin. And it really was because I wanted to test the model out. And I knew those guys well.

I knew they could bring us a group, group of founding members to help test out the model. The way I did test it out initially was San Diego was always a that was the biggest thing I had to test is would people pay for this thing? San Diego was never paid. It was like everybody throwing 500 bucks to cover your dinners for the year, so I didn’t have to go chase you down to get receipts to get reimbursed. So it was like, do that. 

 And when the money runs out, I’ll let you know. So so that was so I tried the same thing with with those two cities. Like first let’s not worry about paid. Could people actually go into a room, show up and still deliver and have a good experience of connecting? And then that was quickly proven. 

 And then when then I went out to other cities in Salt Lake, was my first sort of paid city mastermind, and then and then so so I think what your question, I think was what I think it was just finding two cities that I felt confident in, the relationships with the people running it, that I can fill up a great group of people to quickly vet it.

Dr. Jeremy Weisz: 20:01

Yeah. You know, I’m curious going back to because it’s it’s your relationship. You know, the relationships are obviously, you know, super important to you. And I’m wondering early on you studied I mean, you worked with Brian Tracy and you were a fan of his work. I’m curious who other you know, works.

Are you a fan of back then and now?

Eric Berman: 20:26

Yeah.

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