Josh Gammon headshot

In this episode of The Close, Craig and Josh Gammon discuss the growing litigation funding market and how Wealth Docket, a litigation funding company that Josh co-founded, focuses on complex commercial and patent litigation for individual claimants and small law firms. The conversation covers the challenges of valuing intellectual property, distinguishing between assets with true standalone value versus those only valuable within a business context. Josh emphasizes the importance of client service and shares entrepreneurial advice about balancing confidence with accountability when building a business.

  • Chapters Include:

    Welcome and Introduction to Josh Gammon

    The Birth of Wealth Docket: From IP Monetization to Litigation Funding

    David vs. Goliath: How Big Tech Outspends Small Inventors

    Market Size and Scope of Litigation Funding

    Keys to Success: Client Service and Partnership

    Finding Clients in a Niche Market

    Remote Partnership: Building a Business Without Meeting

    The Future of Wealth Docket: Law Firm Funding and Industry Evolution

    Personal Philosophy: Fear of Losing vs. Love of Winning

    Contact Information and Wrap-up

LISTEN TO THE CLOSE

Exploring the Art & Science of dealmaking

Welcome to The Close M&A Podcast with Caber Hill Advisors, where we bring you exclusive insights from M&A experts, business owners, and industry leaders navigating the complexities of buying and selling businesses. Hosted by Craig Castelli, this podcast demystifies the dealmaking process, shares success stories, and offers invaluable lessons for business owners and investors.

Craig Castelli headshot

MEET YOUR HOST

Craig Castelli, Founder & CEO of Caber Hill Advisors, is a trusted M&A expert with decades of experience advising business owners through successful transitions. Alongside a rotating roster of advisors, entrepreneurs, and investors, Craig brings engaging conversations that illuminate the world of middle-market M&A.

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ABOUT THE EPISODE
Josh Gammon headshot

In this episode of The Close, Craig and Josh Gammon discuss the growing litigation funding market and how Wealth Docket, a litigation funding company that Josh co-founded, focuses on complex commercial and patent litigation for individual claimants and small law firms. The conversation covers the challenges of valuing intellectual property, distinguishing between assets with true standalone value versus those only valuable within a business context. Josh emphasizes the importance of client service and shares entrepreneurial advice about balancing confidence with accountability when building a business.

  • Chapters Include:

    Welcome and Introduction to Josh Gammon

    The Birth of Wealth Docket: From IP Monetization to Litigation Funding

    David vs. Goliath: How Big Tech Outspends Small Inventors

    Market Size and Scope of Litigation Funding

    Keys to Success: Client Service and Partnership

    Finding Clients in a Niche Market

    Remote Partnership: Building a Business Without Meeting

    The Future of Wealth Docket: Law Firm Funding and Industry Evolution

    Personal Philosophy: Fear of Losing vs. Love of Winning

    Contact Information and Wrap-up

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LISTEN TO THE CLOSE

ABOUT THE PODCAST

Exploring the Art & Science of dealmaking

Welcome to The Close M&A Podcast with Caber Hill Advisors, where we bring you exclusive insights from M&A experts, business owners, and industry leaders navigating the complexities of buying and selling businesses. Hosted by Craig Castelli, this podcast demystifies the dealmaking process, shares success stories, and offers invaluable lessons for business owners and investors.

ABOUT THE HOST
Craig Castelli headshot

MEET YOUR HOST

Craig Castelli, Founder & CEO of Caber Hill Advisors, is a trusted M&A expert with decades of experience advising business owners through successful transitions. Alongside a rotating roster of advisors, entrepreneurs, and investors, Craig brings engaging conversations that illuminate the world of middle-market M&A.

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Craig Castelli (00:04):

Welcome to The Close M&A Podcast with Caber Hill Advisors. I’m your host, Craig Castelli, and today my guest is Josh Gammon. I consider Josh an extended member of the Caber Hill family. He’s never been a full-time part of the team, but he is one of our experts that we tap on anything related to intellectual property. So we’re going to talk a lot about that today. And I think I want to start, Josh with your new venture. So [00:00:30] you decided to take the entrepreneurial step yourself and create a company called Wealth Docket. Tell us what was the idea and why did you think it would work?

Josh Gammon (00:40):

Sure. First off, thanks for having me on, Craig. It’s a pleasure. Good catching up with you. Nice to chat with you always. Wealth Docket has been through a couple of different iterations. My business prior to that was around intellectual property and monetizing intellectual [00:01:00] property assets, frequently assets that had not had success as part of a business or were not core to a business. And we did large deals. We would acquire large portfolios of intellectual property for eight and sometimes nine figure sums of money. And oftentimes in the diligence process for those assets, the meets and bounds of the assets themselves got lost, [00:01:30] got lost in the conversations and deals that were already in place around the portfolio of assets. And so I wanted to invest more in small portfolios of assets and around certainly by 2010 litigation funding was a real industry here in the United States.

(01:55):

It was larger in Europe first, and wanted to deploy capital into that space [00:02:00] because from the diligence side, looking at patent portfolios, which is my specialty, and the diligence is more about the assets themselves when they’re smaller portfolios as opposed to ongoing licensing discussions. The other issue that was attractive to me is that small portfolios of patents tend to be owned by inventors or founders. And I wanted to help those folks because the pendulum [00:02:30] has been swinging against patent protection for a long time here in the United States. And I think a lot of people have been hard done by big tech, other large corporate interests with their intellectual property rights trampled all over. So couldn’t make much headway as part of the organizations where I worked previously at deploying capital there, but started learning more about it and realized that while there were few advisors in the space helping [00:03:00] owners of IP and other legal assets to be smart about going out to the market and finding funding to help them enforce their claims around those assets.

(03:14):

You could go out and find litigators and find litigation funders, but typically people were talking to one or two litigation counsel oftentimes was in the middle of those conversations, which isn’t where they should be given that the funding is going to pay their invoices. And [00:03:30] identified the gap. And I wanted to crowdfund it at first, backed away from that. But as I continued to learn about the space, realized that I had been correct, that that advisory gap existed and there was room for folks like me to advise on those deals and do what for all intents and purposes, sell side investment banking around litigation funding. So I’ve talked a lot.

Craig Castelli (03:59):

It’s [00:04:00] fascinating. As you know, I’ve been fascinated in this concept since you first told me about it. If I wanted to dumb it down a little bit, is it fair to say that in a lot of cases the big tech companies, whoever they may be in each instance, just simply have deeper pockets and the ability to outlast the little guy when it comes to litigation? So if I want to enforce my patent, they can string things out, they can [00:04:30] appeal, they can file motions, and eventually if I’m just funding it myself, I either run out of the money to keep fighting or the will to keep fighting and then they get away with this?

Josh Gammon (04:41):

Yeah, or both. And I didn’t want to get political right off the bat, but here we are. That’s exactly what happens. Big tech, certainly in the United States has long had as part of their playbook, intellectual property theft, and they do get away with it because it [00:05:00] costs millions of dollars to support the types of litigation to combat intellectual property theft. Litigation funding is beginning to stop that. I don’t know if you were paying attention to the news, but a couple of months ago, as part of the big beautiful bill, there was actually an excise tax that would’ve put many funders out of business. Tom Tillis introduced it. No doubt. Large corporations had his and the other folks ear who [00:05:30] were interested in passing that legislation because they don’t like it. Meritorious well-funded lawsuits are being brought because of litigation funding. It’s growing, it’s large.

Craig Castelli (05:44):

So playing off of that for the target market that you’re focusing on, how big of a market is it?

Josh Gammon (05:53):

You hear various numbers, Craig. I think $16 million in assets under management [00:06:00] is a common one that’s bandied about. It’s really difficult to know how large the market for complex commercial litigation and patent litigation, which is where we sit, is I would say certainly it’s hundreds of millions of dollars per year, likely single digit billions. I couldn’t give you firmer numbers than that though, because there’s litigation funding around product liability claims, class actions, [00:06:30] mass torts. It’s very difficult to know which funders are doing which things. I could tell you which litigation funders do patent litigation, for example. But I couldn’t tell you, they don’t do those other things too. But for some perspective, it is very, very small relative to real estate. For example, as an asset class that institutional capital invests in.

Craig Castelli (06:59):

Of course, and [00:07:00] tougher to track and peg a market size. It’s not like there are annual reports filed by these funders that are disclosing where they’re spending their money.

Josh Gammon (07:09):

Well, Burford for example, is publicly traded, and so they do file, but they are global. Certainly we are fairly US based and they are invested in all kinds of things, including some litigations that are larger as a single matter [00:07:30] than the sort of corporate rock throwing that you might find in the United States alone.

Craig Castelli (07:36):

Yeah, that’s interesting. So you’re a couple years in, things seem to be going well. What’s been most credible, most critical to the success so far?

Josh Gammon (07:48):

Well, we are a client service business. Most of our clients are claimants. They tend to be individuals or small partnerships, [00:08:00] not formally partnerships necessarily, but groups of between two and five individual people who have a business and have been done wrong by someone. And the rest of our clients are law firms. Most of those law firms are also quite small. I think from the beginning as we knew it was very, very important to be responsive to our clients and to care about them and to make them understand that we cared. We fairly quickly [00:08:30] put in our wake several clients who had had a great experience with us because of those things that we now are able to point potential clients to, and that gets engagements for us. The other thing I would say is Alex Lempiner, my partner and I, we probably argued about our operating agreement for a couple of months and worked a couple of deals before we actually signed up. But I still think that both of us feel that we got fortunate with who each [00:09:00] of us turned out to be the right partner is key, obviously.

Craig Castelli (09:04):

Absolutely. How are you finding your clients or are they finding you?

Josh Gammon (09:11):

I think that the clients are very, very interesting. We do do a lot of patent work and they tend to be inventors and engineers, which are my very favorite people. I think the smartest people out there are the engineers. I’m a lawyer by training and a financier, and lawyers [00:09:30] and financiers tend to think they’re quite intelligent. And I always kind of shrug and say, you’re not an engineer, but so engineers tend to have a little bit less of the business and legal savvy. There’s a human element to them that guys like you and I don’t always get in the conference rooms that we’re in. So I enjoy those clients very much and all of them very much. In terms of how they find us.

(10:00):

[00:10:00] I think that when they hire us, much like when Alex and I hired each other, they don’t really know what to expect, but they’re hearing good things. I think they come to have a great deal of respect for in aggregate the amount of expertise that Alex and I have because I’m on the finance and economic side of the house and he’s on the transactional lawyer side of the house. But I think the clients find the process frustrating because this is the most difficult kind [00:10:30] of sell side investment banking I’ve ever done. It’s time consuming. The funders are difficult cats to herd. So I like to think we take a process that is frustrating and make it less frustrating and make friends along the way.

Craig Castelli (10:48):

Did I see correctly, since you’re talking a bit about Alex, you guys are business partners, but you’ve only actually met each other a couple times at least in person.

Josh Gammon (10:57):

That’s right. That’s right. [00:11:00] My wife and I flew to Philly where he sits before we signed our operating agreement and met Alex and Tracy, his wife, and had dinner together and that was it. And then I went by myself and spent a weekend with Alex and met his family recently. But we’re on the phone three, four hours a day probably.

Craig Castelli (11:22):

Sign of the times, man.

Josh Gammon (11:23):

Yeah, it’s very odd. And I think people locally here, I live in a small community in South Carolina [00:11:30] and the people that I talk to about that who are friends who run local businesses, bricks and mortar businesses, they think that that is absolutely insane.

Craig Castelli (11:44):

And 10 years ago, I think everybody would’ve, but the world has changed. We all work differently right now. We’re chatting about that before we even hopped on here. And so the fact is it’s working and when you have two professionals who have the capabilities [00:12:00] that you have, as long as the personalities and the visions align, you guys will make it work. So where’s Wealth Docket in five years?

Josh Gammon (12:09):

That is a good question. We’re always trying to stay agile. Litigation finance is relatively new. It’s changing quickly, and we’ve got a good thing going. And that means a couple of things. One, it means that come competition is coming. [00:12:30] Not that there isn’t any now, but there are new entrants just this year in the space that are doing exactly what we’re doing. Well, they’re not doing exactly what they’re doing, but they’re in the category. It means that change is coming and it means that the industry can quickly shift away to something else. So one of the things that we are seeing is law firm funding facilities, and this has always been a thing where a law firm can go to the bank and get a bank loan, but more and more this is trending toward [00:13:00] funding for law firms that’s collateralized by the proceeds of multiple or all of their cases.

(13:08):

And I’ve talked to probably three law firms in the last month that have told me, yeah, yeah, we’re closing a deal like that. And closing isn’t the same as closed, but it’s coming. And it’s not that we don’t do any of that work, but the place for an advisor is a little bit different on those deals. So over the next five years, I think [00:13:30] that Alex and I, and more, because we’re not hiring right now, even though we desperately need to, Alex and I will be doing more of that work, I think more law firm clients. And I do think we’re going to be doing more legal and consulting work as well. We’re in the process of standing up a law firm to get some of the legal work that we think is leaking away from us on deals where we don’t get [00:14:00] selected to do advisory work, but somebody’s got to do the deal documents, somebody needs to help with diligence. And I think that’s coming.

Craig Castelli (14:09):

Sure, that’s fascinating. So let’s shift gears here. In the past when we’ve worked together, it’s typically when we at Caber Hill have started working with a client that’s usually a startup or has some very unique intellectual property. And while we do [00:14:30] a decent amount of evaluation work, those are areas that are just completely outside the realm of our collective skill sets. And so we’ve worked together on some very interesting things. We were helping to raise capital for a pre-revenue company that was bringing AI to the collectible space. And we’ve looked at some other similar opportunities like that where the valuation is completely disconnected from the P&L in that venture capital technology [00:15:00] sense of things. I guess just talk a little bit about how you go about valuing these companies, especially the really, really early stage that have all the potential in the world, but maybe they have a beta version of a test product at best.

Josh Gammon (15:15):

Yeah, I’m appreciative, Craig, that you always call me when somebody does not have a P&L disconnected from the P&L.

Craig Castelli (15:23):

I dunno what that says about you, but you’re my guy for it.

Josh Gammon (15:28):

I think [00:15:30] the first thing that you think is who is the target audience for the valuation? Because I think there has been work product that has been called the evaluation, whether or not it was a formal appraisal in all of those engagements. And my first thought is who’s going to be looking at this? Usually when we’ve worked together, it’s been investors and investors that invest in pre-revenue or near pre-revenue [00:16:00] companies. If they do it frequently, if they do it well understand that really what they want from us is not an appraisal with a number or a tight band of numbers.

(16:17):

And so I would tell you how do you value that? The answer is with difficulty. I view what we were doing is sort of helping to paint the [00:16:30] various paths and scenarios that the company might proceed down and a VC or a sophisticated private equity or hedge fund or individual investor that’s investing in companies like that is going to be sufficiently diversified, that informed by such valuation analysis on each of those deals across all of them, they’re going to make money. And I think the other way they know is because they have a relationship [00:17:00] with management. So the way you do a valuation or appraisal of that company is the same as any other company. It’s heavily discounted cashflow based, and you’re forecasting revenue and expense for the business as a whole and making qualitative calls about how the business is going to penetrate or create this or that market in large part because of their intellectual property on the stuff that you and I are working on.

(17:30):

[00:17:30] But I think part of the question is not just how do you value it, but how do you have any faith in your valuation? Part of it is diversification on the investor side because usually this has been for investment decision making, but if you look at the VC community in Silicon Valley and elsewhere for a very long time, the management team was the key factor that was assessed. And Brad Sarna, who we also worked alongside [00:18:00] and I both look at that as well. In fact, I think the most recent thing we looked at together was in the life sciences. It was an optical solution. I won’t go further than that for confidentiality purposes, but I think you, Brad and I were in agreement there that the executive leadership team, their skills, knowledge and experience, and probably most of all their Rolodex, their connections, were going to let them take something that was almost [00:18:30] inarguably from an IP perspective, superior.

(18:34):

And they had the clinical testing results to back that up and give the additional confidence that they were going to be able to productize, monetize. So long answer to recap, how do you value it? Certainly with difficulty, how do you have confidence that it’s going to be successful? You never communicate too much confidence. I think as an appraiser, [00:19:00] you need to be realistic when valuing early stage companies, particularly technology companies, but you have to take into consideration the qualitative factors to have confidence of success. Who’s management? What are their relationships? What’s their specific plan?

Craig Castelli (19:17):

Yeah, I mean, there are certain management teams out there that you can look at and say, I will back you to do anything. Because within a category, they’ve just shown the ability to [00:19:30] stamp out success after success after success. How much of the approach to valuation is trying to predict whether the company will actually be successful and how much of it is just playing into the Dutch tulips game, for lack of a better phrase, where you just show the help the investors see, as long as these certain things happen, I can get my money out of it and then it may be someone else’s problem.

Josh Gammon (20:00):

[00:20:00] I think that goes to knowing the audience for the deliverable, and that’s a function of what is communicated to me that is desired. And it depends on is this an equity investment we’re contemplating? Is it credit? Because of course, downside has different meanings in those two scenarios. I like to think that downside protection [00:20:30] and downside scenarios isn’t the reason that I as an expert and brought into deals. I think it’s more for me about giving credence to the base and the high case that there’s going to affirmatively be success rather than just a deal an investor doesn’t get burned on.

(20:53):

I operate in Excel still. Do I still stay handy with Excel? And I think we’ll talk about why that is a little bit later on [00:21:00] in the show, but it isn’t just the numbers. I think I like to think when you bring me in, it’s because folks look at my CV and many of them have asked for it, and they see a long track record of doing valuation and strategy work around intellectual property and early stage companies and are not just looking for the downside protection story, but are looking for the what do you think about whether this is going to be a winner.

Craig Castelli (21:27):

And there are so many variables of it, you can have the best [00:21:30] idea or the best solution in the world, and if you can’t get capital to scale it or you capitalize it poorly, you don’t have a business and it doesn’t matter how great the idea is.

Josh Gammon (21:40):

Yeah, yeah. I mean the pre-money and the post-money valuation are different for a reason. And I think that self-fulfilling prophecy that self instantiation exists with both the management team and with the money. There are management teams that you would trust to succeed with anything because of the track [00:22:00] record and because you and I and others would trust them, people do trust them after we invest in them and that momentum gets things done. And likewise with the investment, you raise a really important point when you’re valuing intellectual property or tech companies, A major question is, well, how much money are they going to have to do what they need to do? Because without the capital, it’s worth nothing.

Craig Castelli (22:27):

Yeah. We will also sometimes [00:22:30] see more traditional mature businesses that claim to have a technology component that has value to it. And it’s always something that I rolling my eyes at. It might be a gentle way of putting it, and I don’t want to get too specific because I don’t want anybody to recognize if I’m talking about them, but they will substitute what everybody else in their industry is buying off the shelf and they will develop it internally. [00:23:00] And so without saying too much more to forecast any sort of answer, what are the points where you would say that that might actually have some intrinsic value versus just being a part of the business itself and not necessarily enhancing or having value on a standalone basis?

Josh Gammon (23:23):

The biggest one is going to be exclusionary rights like patents where you can go out and [00:23:30] stop someone from doing something, even if you separate the asset entirely from the business. And then a marketing intangible like a trademark where once the consumer recognition or the recognition in the buyer market, whether that’s consumers or businesses or some mix is large enough that it would be saleable on its own. And I know that answer maybe got a little bit circular, but you point out an important problem [00:24:00] I’ve run into in the past. I have been a purveyor of IP valuation and strategy consulting full time at the beginning of my career, and folks would hire us and say, can you value the intellectual property? And we would say, well, of course we can come up with a means of isolating the economic utility that’s attributable to that intellectual property and giving you a theoretical view of what the value is.

(24:27):

And [00:24:30] I had engagements where we would get through the engagement and they would say, well, it’s great to know that in a downside scenario we could sell the intellectual property for that. And I would say that that’s not what we said. We very pointedly didn’t go with a fair market value standard of value here. It doesn’t have intrinsic value, its value as an assemblage of assets in the context of your business. So unfortunately sometimes in my career, there was a mismatch between what the client [00:25:00] was asking for and what they thought that they were asking for. But exclusionary rights, patents are the quintessential example. If they are infringed outside of your company, if they’re implemented outside of your company, they have value outside of your company. But I have a CRM, for example, that I developed in Excel because I wanted control and I’m an Excel creature and I didn’t want to pay, who’s the big one?

Craig Castelli (25:27):

Salesforce.

Josh Gammon (25:28):

Yeah, thank you. I didn’t want [00:25:30] to pay Salesforce or anybody else to develop it, and it’s this crusty tool that works for me. But I think you come across and I come across companies that have software that’s been internally developed, like you said, because they didn’t want to pay for somebody to do it or to buy the off the shelf one, and it doesn’t have value outside of the assemblage of assets that is the company. And they think that it does because spent time on it.

Craig Castelli (25:56):

And I think that there may have been a point at its inception [00:26:00] where it did have a unique, but at the end of the day, they’re still an operating business doing whatever else they’re doing on a full-time basis. And let’s say it’s the example of a CRM because we have seen this a few times with CRMs or CRM like technology that’s homegrown. They don’t continue to develop it the way that the pure CRM companies are pouring millions, if not tens or hundreds of millions in developing their product and adding the latest features and bells and whistles [00:26:30] and these days, AI to what they have to sell. And so that product falls behind. We’ve seen it to the point where it’s actually a detriment to the business that it’s either holding them back in their operations or it’s just viewed as something that’s substandard for their scale by a potential acquirer.

Josh Gammon (26:50):

Yeah. Yeah, that makes sense. And in a deal context that really can hold you back. I mean, it may be working, but I think it detracts from the credibility [00:27:00] of management when you get people under NDA and start showing them under the hood, and you’re using tools that are crusty and old because they may be functioning, but the risk of them collapsing and ceasing to function is high. And there might be problems around information security, privacy, cybersecurity, all of these things with using homegrown software that you wouldn’t have if you were using something that wasn’t on premises and was in the cloud but [00:27:30] was hosted by a reputable company like Salesforce, for example.

Craig Castelli (27:36):

Yeah. I look forward to the day that you call me and you say you’re ready to sell Wealth Docket, and I ask you if you’ve graduated from your homegrown Excel based CRM to Salesforce or something else. We’ll see if you’ve taken your own advice along the way.

Josh Gammon (27:52):

Yeah, we will. We will. And honestly, I don’t use it that much anymore. I will tell you though, our IT [00:28:00] had been in-house until recently and we were briefly compromised by a phishing exploit, no harm done, but it was a reminder to stay vigilant and also a reminder that we’re a growing company with increasingly important relationships with access to increasingly sensitive information and doing anything technology based, unless you are the specific type of engineer who does that as their day job, nine to five, [00:28:30] is not a great idea.

Craig Castelli (28:33):

No. Like most things and most entrepreneurs, you are really good at a couple things, and then there’s all the wraparound services that you need to run your business. And I was certainly guilty of this and probably still am to a certain degree. As you’re building a company, you look at ways to reduce cost. You think, well, maybe I can just do this on my own. I mean, we’re entrepreneurs because we thought we could do things on our own in the first place. And so that extends to other [00:29:00] functions of the business. I’ve said this a hundred times. Every time I finally let something go and outsource it or hired somebody to do it, I end up thinking, why didn’t I do that five years ago?

Josh Gammon (29:15):

We haven’t outsourced much yet, but I hear you and hope to continue to have that experience. Let’s say

Craig Castelli (29:23):

You’re early enough that we will let that slide, that seems normal. It took me many more [00:29:30] years than you guys have been around to outsource things like IT and marketing. So I fully appreciate that.

Josh Gammon (29:36):

Well, I mean, it was the first one and I am glad not to be dealing with it. It is funny though, because you can hire a platform company like Microsoft and sort of set it and forget it, and it’s enabled a whole lot of folks to start businesses, particularly during the pandemic and the years after. But just because you’ve forgotten [00:30:00] it and it doesn’t seem to be doing anything, doesn’t mean that it’s doing what it’s supposed to be doing.

Craig Castelli (30:05):

Right. Yeah, that’s a great point. So I want to wrap here with the final question and I want to hear a piece of advice that you would give to the business owners in the audience here today.

Josh Gammon (30:20):

Yeah, sure. And it goes to what you were saying about understanding that you’re an entrepreneur, you’re a business owner, presumably [00:30:30] you have accomplishments, you can do a couple of things. Well, and some of the most dangerous folks I’ve encountered in business are folks who have had a good run of success doing one or two things well and get the idea that they can do everything well. So with that as setting the table, I will tell you my advice is you have to be two people to be an entrepreneur or a business owner, particularly a small [00:31:00] business, particularly a business that you started yourself, which is my experience. There’s fairly good literature out there showing that a little smidge of sociopathy, narcissism goes a long way with entrepreneurs. You almost have to have an unrealistic expectation for what you can do. And certainly in my own psychological makeup in the way that I get myself going for particular meetings, I am in my head thinking to myself, I can do [00:31:30] this very well.

(31:30):

We’re going to crush this meeting. Whatever the context is, you have to have the confidence to believe that you can go out and play the most competitive sport that’s ever been played with real money, real time, time that you could be working for somebody else, collecting a paycheck time you could be spending with your partner, spouse, your children, and go put that on the line and bet it. And so you better believe that you can do something better than somebody else can, but the other person [00:32:00] that you have to be, because everything is your fault when you’re an entrepreneur, is a person who can accept the times that you didn’t do a great job or made a mistake. And a specific example I’ll give you is in our Wealth Docket iteration, we brought in a third party who we knew to be very good at what they did to assist one of our clients.

(32:28):

And that third party [00:32:30] didn’t do work with the same client service ethos that Wealth Docket would’ve done it with and maybe didn’t leave the client of ours disappointed, but not as pleased as we would like for them to have been. It would be easy to blame the third party and assume it was their fault, but really that wasn’t their fault. I had an imperfect understanding of how that relationship was going to go, and my client is looking to [00:33:00] me to know. And so you have to be at the same time, the sort of sociopathic narcissist that thinks you’re going to go out and win this very difficult competitive game with so many smart people in it. But at the same time, you have to be a person who’s humble enough to recognize when you did something wrong or when you need to outsource something to keep your cybersecurity safe. And I think that’s one of the things that I have learned. It’s difficult to have those two personas in one head, but you [00:33:30] need to be agile at trotting out the right one at the right time.

Craig Castelli (33:34):

Yeah. It reminds me of a question I used to ask people in a prior career when I would interview new hires, you can’t say you’re both. Would you classify yourself as somebody who loves winning or hates losing?

Josh Gammon (33:51):

What was your answer, Craig?

Craig Castelli (33:54):

It was definitely hating losing. That I would say has always driven [00:34:00] me more. The wins are enjoyable, but they’re fleeting. The joy dissipates. I have to, we make a point to celebrate every single deal that we close, but then in this business, it’s onto the next one and it’s on to the next one. And so you can’t just sit there and bask in that glory. I don’t really think there’s a right or wrong answer to the question. At the end of the day, you should have an element of both. But that’s what makes it a fine debate, is you have to just choose one side.

Josh Gammon (34:29):

Yeah, [00:34:30] I agree. And I’m with you on that one. And that may just be about where I am in life right now. I hate losing. I’ve got little kids, and so I need to not lose, I guess financials, security, and that means different things to different people is something that I’m running towards. But I read an interesting piece about what separates American capitalism [00:35:00] from the rest of the developing world. And an expert made the point in this country, if you aren’t gainfully employed, you don’t have healthcare, right? And the politics of that situation aside, I do think that there’s some truth to the fact that we in America here maybe work harder, maybe work longer hours, maybe are more averse to potentially losing our jobs because there is [00:35:30] less of a safety net than in much of the developed world. And in my own present circumstance, I am quite averse to losing because of the folks that are counting on me to win. Now, I think later in my career, that might be the time when I’m like, no, no, no. Now I love winning. I’ve earned my financial security, and now it’s time to knock it out of the park and live for the wins.

Craig Castelli (35:54):

Right now. You just need to know how to turn that off when you’re playing basketball against your 6-year-old and let them get a win every once [00:36:00] in a while.

Josh Gammon (36:00):

Yeah, it’ll be a while before he can beat me in basketball. Although basketball, he might be able to beat me right now. It’ll be a while before he beats me in a foot race of let’s say three miles or longer.

Craig Castelli (36:10):

Yeah.

Josh Gammon (36:10):

Let’s hope 20 years or so.

Craig Castelli (36:12):

Nice. Well, Josh has been a lot of fun. If anybody listening or watching here wants to get ahold of you or just learn more about what you’re doing, where should they go?

Josh Gammon (36:22):

So our website is simple. It’s www.wealthdocket.com, and actually [00:36:30] our email addresses and phone numbers are on the website as well.

Craig Castelli (36:34):

Perfect. So that’s wealthdocket.com. Check ’em out. Josh, thanks for joining us here on The Close.

Josh Gammon (36:40):

Hey, thanks so much, Craig.