Episode #610: Navigating Legal Challenges in Fitness-Cory Sterling on Waivers, Compliance, and Scaling Safely
Welcome back to HALO Talks! In today's episode, host Pete Moore sits down with Cory Sterling, founder of Conscious Counsel, legal advisor, and entrepreneur dedicated to the health, active lifestyle, and outdoor (HALO) sectors. After starting his career in professional sports marketing and feeling uninspired by traditional corporate law, Sterling pivoted to blend his passion for movement and wellness with legal expertise, serving gym owners, studio operators, and wellness entrepreneurs across North America.
In this episode, Cory explores the changing landscape of proactive legal strategies, the critical importance of customized waivers, and the pitfalls of cutting legal corners, especially in a sector known for its rapid innovation and ever-changing service offerings. From emerging liabilities in fitness centers offering pseudo-medical treatments to the impact of new click-to-cancel regulations and best practices for contract scalability, Sterling delivers actionable insight for operators looking to protect their business and reputation. If you're building or scaling a business in the HALO sector, you won't want to miss this conversation!
When it comes to using AI in place of real, boots-on-the-ground legal expertise Sterling says, "ChatGPT is helpful to some extent, but the thing is that AI doesn't have is the history or the experience of having done this very, very specific thing over and over again to understand what sort of problems will come up and to produce a document that, A, you understand, that has the things that you need, and B, proactively goes against the issues that a law practice that's been doing this for 10 years."
Key themes discussed
- Proactive vs. reactive legal strategies for fitness businesses
- Importance of industry-specific, customized legal documents
- Scaling legal services via referrals and word-of-mouth
- Impact of technology and AI on legal processes and pitfalls
- Evolving liability waivers due to new wellness services
- Click-to-cancel laws and compliance challenges
- Structuring agreements for med spas and new offerings
A Few Key Takeaways
1. Proactive Law Is Essential for Scaling and Protecting Your Business: Cory emphasized the critical distinction between "proactive law" and "reactive law." Investing in legal documents and compliance up front empowers business owners to resolve issues quickly—sometimes with just a single email—rather than scrambling after a crisis hits 05:10.
2. Industry-Specific Legal Agreements Create True Protection: Sterling underscored that generic contracts, including those generated by AI tools like ChatGPT, are not sufficient. Only industry-specific, lawyer-drafted documents ensure full coverage for unique risks in the health, fitness, and wellness sectors. Customized waivers and agreements need to reflect actual operations, activities, and equipment used 19:19.
3. Rapid Industry Evolution Demands Ongoing Legal Updates: The sector's expansion into new areas, such as hormone therapies, IV drips, contrast therapy, and recovery modalities, means that legal documents must be routinely updated to reflect expanding services and regulatory changes (e.g., ADA requirements now extending to online platforms, click-to-cancel laws).
4. Strong Relationships and Word-of-Mouth Drive Growth: Sterling built Conscious Counsel through deep niche expertise and authentic relationships in the HALO community. He highlighted that word-of-mouth and referrals, backed by stellar client experience and reviews, are the engines of scalable legal services in this space 04:10.
5. Cutting Corners in Legal Can Derail Your Brand and Exit Strategy: For executives with aspirations to scale or exit, Sterling's advice is clear: legal is not the place to cut corners. "You can pay me now or you can pay me later," he said, recounting common scenarios where avoidable legal oversights, like hiring misclassifications or poorly drafted waivers, led to major operational and reputational headaches 22:30.
Resources:
- Cory Sterling: https://www.linkedin.com/in/corysterling/
- Conscious Counsel: https://www.consciouscounsel.ca/
- Integrity Square: https://www.integritysq.com
- Prospect Wizard: https://www.theprospectwizard.com
- Promotion Vault: https://www.promotionvault.com
- HigherDose: https://www.higherdose.com
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This is Pete Moore on Halo Talks NYC. I have the pleasure of
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bringing a very qualified legal professional, also
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quite frankly a great entrepreneur, uh,
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Corey Sterling, coming in from Conscious Counsel. Good to have you on the
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Halo Talks and, uh, introducing you to our audience. Pete, thank you
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so much for having me. I'm so happy to be here on Halo Talks and
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excited for a great conversation. Awesome. So, why don't we first
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talk about your background, your career,
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and how you've pivoted into a very interesting niche that
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we believe is a full-time job serving the health, fitness, and active
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lifestyle industries? Happy to start there. I used to
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work in professional sports. I did marketing for the NFL
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and the Oakland Raiders in a different lifetime, and I did a
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lot of informational interviews when I was there, including with Roger Goodell, the commissioner of
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the NFL. And, I was quite young. I was
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23, 24, and I said, what advice would you give to your
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younger self? And, all the executives I spoke to or met with said, I would
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get an MBA or I would go to law school. So, I went to law
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school later in life, became a lawyer, worked
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downtown in a suit and tie, was absolutely miserable as you can
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imagine. Not me. I'm all about people. I'm all about movement. I'm all about
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health. At the same time I was working at that law firm, I was teaching
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yoga classes and cycling classes and group fitness classes at
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Equinox and other gyms in Vancouver, British Columbia, Canada.
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And, one day I went to a yoga class, one of the students in class
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got injured. We didn't sign a waiver. I asked the teacher who was my
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friend. I was like, hey, what happened? Where's the waiver of
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liability? And, they just didn't understand what it was about. And
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then, I started having more conversations with other friends of mine who were
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health and wellness professionals, gym owners, studio owners. And I
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realized no one really knew anything. This was in 2016. And
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so I was just like, cool. I was ready to quit being a lawyer because
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I was so unfulfilled working in the corporate space. And I thought,
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before I quit, I might as well just try to serve a community that I'm
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a part of and a community that I'm passionate about. And I started Conscious Council
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and just began serving, started very, very low scale
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working with yoga studios, gym owners. And since then,
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it's It's grown a lot, a lot, a lot. And 9 years later, here we
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are. Yeah. So when you started doing this, were you trying to get
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on as their power of attorney,
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their lead lawyer, or did you just say, hey, look, let me just
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come in here and basically make sure that all your documentation is in
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order? Yeah, it started really from help and pro bono,
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right? I had a full-time job. I was wearing a suit and tie. And so
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These people are my friends, and I saw them doing things incorrectly. And
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so I just thought, like, yo, let me look at what you're doing, and
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let's set you up to do it correctly. And I probably had 3 or 4
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of those sorts of experiences where I just helped people, and then I realized
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suddenly, actually, there's a need. Yeah. This is
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the truth. Now, in 2026, maybe it's a very little bit
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different, but in 2016, no lawyers were paying
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attention to Boutique fitness studios, 2 Pilates
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studios, 2 gyms, 2 yoga studios.
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And so, for me, it just was a natural niche. And then, yeah,
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I've spent the past decade essentially just
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fixing the same problems that a studio will go through that a health
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and wellness outdoor business will go through. And, that's really been
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my passion. And, how's word been getting
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out or how have you kind of morphed the business into
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more scalable— I know you could download some
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templates and things, right? It's really the— and
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for all entrepreneurs who are listening, I think it depends what your intentions are. Some
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people build businesses to scale and sell. That was never for me.
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I always wanted to have a business that was my unique offering to the world
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that I thought the space needed to apply my particular technical
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skills to help people in a way that's in alignment with the vision I have
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for the person who I am and the community that I want to build. And
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word of mouth is just like, if you're in that game, word of mouth is
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everything. Right now we've got 466
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5-star Google reviews. All of our clients give us 5-star reviews, and
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a lot of our business comes from referrals from existing clients.
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We've won some awards in the past, which helps, and usually just doing
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partnerships or joint ventures. A lot of the time I'll get on a call and
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the first thing a client will say is like, Wow, I'm so happy that you
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exist. I had no idea about this. So, like, for most businesses out there,
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the question is, how can you create awareness and attention so that people can
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understand the gift that you have and the ability to
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work with and use your services? Does that answer your question? Yeah, it does.
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Are you focused on the front end when
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people are starting their businesses, or are you
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typically coming in when something happened? Well, there's
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proactive law and there's reactive law. And that was one of the first
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concepts that I understood when I started doing this. Proactive law
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is I'm about to open. I know I'm going to hire. I'm not sure
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if they're employees or contractors. I'm not sure if my waiver of liability will cover
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supplements, all those sorts of questions. I don't know how to come up with
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a membership guide or behavioral expectations for my members.
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Proactive. You draft the documents first, you invest in legal
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upfront, and then when there's an issue down the line, it can be resolved with
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one email. Right. Conversely, reactive law is, hey, I'm going to cut
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corners. I'm starting this thing. I don't really want to invest in legal right now
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or to do things properly. 8 months down the line, you have a
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contractor who you— you have an employee who you were calling a
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contractor who now is threatening to call the
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IRS against you. I went through this last week. Not fun.
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For all of my clients, I always want them to be in control of the
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situation. And the way that you control the situation is by having
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industry-specific documents drafted by a
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lawyer who understands your business and the specific relationship you
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want to have with your clients. So proactive law has to be the way.
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This is Pete Moore. I want to let you in on a little secret. There's
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this company called Promotion Vault, and what they do is they give out rewards
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from retailers that allow you to incentivize your
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members without having to do zero down and one month free,
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or giving away shakes or giving away t-shirts. What you want to do is
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build a rewards program that lasts, that people value,
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and that doesn't discount your own products and services. So here's the deal.
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There's something called Rewards Vault. The Rewards Vault is going to allow
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a member to set up their own profile. They are going to answer
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questions. You are gonna get those answers. You're gonna be able to target those
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members and you're gonna reward them inside your club,
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inside your spa, and outside of the club and outside of the spa
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to get them to become loyal, to get them to pay their monthly dues,
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and to be rewarded properly for the actions. A lot of companies
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are cutting back on rewards. You shouldn't be. Promotion Vault's your answer.
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Trust me, this is real.
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When you get on board with an entrepreneur, and I've been an
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entrepreneur many times, they are very hesitant to invest
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in things that they don't think are, you know, core to like launching the
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product or the service. And, you know, probably
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even now worse with, you know, ChatGPT and Claude, thinking you just ask a question,
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you know, you get your answer and you're covered. My point of that was, are
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you seeing smarter entrepreneurs that are being
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proactive now? And is your service so
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scalable to an extent that, you know, it's not like you don't need
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100 hours of your legal services to get
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somebody up and running? Okay, 2 questions there, and I'll break them
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down individually. Am I seeing smarter consumers? Are people— are
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entrepreneurs getting smarter? Entrepreneurs are becoming more dependent
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on technology, and the limitation with that is like,
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ChatGPT is helpful to some extent, but the thing is that
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ChatGPT doesn't have the history or the experience of having done
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this very, very specific thing over and over again to understand what sort
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of problems will come up and to produce a document that,
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A, you understand, that has the things that you need, and B,
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proactively goes against the issues that a law practice that's been doing this
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for 10 years has in place. The other big pivot on the first front.
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So I'd say that entrepreneurs now will be more— the questions I get are different.
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because I can tell clients are using ChatGPT. But also, for me, it's
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helpful because sometimes my clients have issues,
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and the contract in question is drafted by ChatGPT. And then it's very
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easy for me to challenge it and overcome it. Your legal position is connected to
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the strength of your legal documents, always. Right. That's how your business runs.
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If you have contracts that are specific, drafted for you, the industry that
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you're in, you're in great shape. If you don't understand your contracts, or you're
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just letting ChatGPT draft it, there are going to be holes. And when those holes
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get exposed, it's the same as not having something. In terms of
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the scalability of the business, I've always had a philosophy
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of doing like, I want to do one thing best in the
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world. You know, Good to Great by Jim Collins. Sure. You know, the
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hedgehog principle? The hedgehog principle
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is like, choose something that you can be the best in the world at. And
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so, what for as a legal, as a the legal practice that I've grown,
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we basically draft 5 types of agreements and we help clients with
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trademarks and licensing, and that's it. And there's a lot of work
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that I refuse because it's outside of my zone. And so, it's scalable in the
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sense that now it takes me
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10% of the time that it used to take me a lot longer.
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So, onto the agreements and obviously state
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waivers, you know, there's, there's liabilities,
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there's, you know, precedent transactions that people are, you know,
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lawsuits or settlements that people are trying to, um,
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you know, ensure that they are, they're covered on. Um, so
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are there any, you know, are there like 2 or 3 things that,
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that have happened, you know, like in the last 3 or 4 years,
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let's say post-COVID, where you're like, well, this is kind of like part of the
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waiver now that maybe wasn't, or here's like a new thing that we've
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Inserted in for clients because we've gotten some issues
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related to something that was missed? Yeah, it's a great
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question. And one thing that we've seen has been with health clubs
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and health services and gyms that now sort of offer
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alternative— they're definitely not medicines, but pseudo-medicinal
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practices of coming up with protocols that
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include hormones or different types of things or injections or
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blood works or Ozempic or all of those different things that are taking
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place. We've had an issue where sometimes that can be construed as
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pseudo-medical services, which invite a whole
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plethora of legal liability outside the scope of what a normal
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gym would have, as well as— and so the changes that
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have need to be taken place for that are in the
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waiver and in the service agreement, and also working with businesses
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specifically to structure in a certain way so that they're shielded from
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liability in those situations. And, the other
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thing that I'd say that I've seen is just
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increasing the scope of all the different activities that
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gyms will do, not only just with supplements
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and the pseudo-medical services but a lot of stuff around breathwork,
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around contrast therapy, around saunas.
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That's something where a lot of the times a studio owner will offer
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new services but keep their documents the same. That's it, I guess. And so,
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it's really important. And then, the last piece
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I'll just add, last year was the click-to-cancel laws, which really,
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really threw a big wrench in the system because it
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changed how autopay works. It changed how people can cancel
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annual subscriptions and working with my clients to make sure that
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if someone cancels something early, you still get paid the amount that you would've
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got paid if you agreed to that particular timeframe
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at the start. So, a lot of changes, really interesting.
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And yeah, it's dynamic and it's flowing.
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Have you dealt with anything related to gift
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card expirations and/or
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prepaid sessions that have been, you know, that people try to burn
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off, let's say, and not fulfill? Not that they wouldn't honor it in the right
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situation, but— Nothing specifically
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around gift cards. I did have a client who
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sold certain sessions They followed up with the person who
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bought from their studio, and the person just delayed, delayed, delayed,
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delayed, never responded. And then that person issued
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a chargeback for the amount. And it was quite a number of
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sessions. But look, this is why you need the agreements. In that situation,
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we drafted the membership agreement for that particular
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type of service. We said that there was an expiry, that every 90
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days, any unused sessions will expire and you'll have to buy again.
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And so we submitted the claim and we won. So it's— that's why you just
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want agreements to reflect the relationships you want to have. Got it. So
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Corey, what have you seen on the click-to-cancel and how
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vigorously is that being enforced? Or
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what's the compliance like on this so far from your viewpoint?
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So click-to-cancel is federal, so it's going to apply to all
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businesses. And where I've seen the majority of click-to-cancel issues come
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up has been someone disputing contract or a membership agreement.
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So they're supposed to pay a certain amount, they sign up annually, so they're paying
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$200 a month when they should be paying $400 per
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month. And then after 3 months, they just decide, oh, actually, I don't want to
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pay this anymore. So now I'm out and I cancel.
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And when that situation comes up, you need to demonstrate that your legal
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documents reflect all of the click-to-cancel rules that you followed. It's
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just about compliance. You did A, B, C, D, The agreements are
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correct. The agreements have all the legal elements. If that person,
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you know, when you're challenging the chargeback, you're able to
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show in the contract that you followed everything. And also, I often send
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emails to people saying, hey, I understand that you terminated this agreement.
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Legally, you're not permitted to. This is the amount that you have to owe. If
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we have to pursue this, we reserve the right to counterclaim plus interest
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plus fees. So it's not— I haven't seen it so
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much enforced governmentally. like by a governmental entity or
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body that's going after people. But in day-to-day, anyone
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who has subscription services, you, you have to be on the right side of that.
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This is Pete Moore. Here's the last tip for you of the podcast.
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We are partnered up with a company called HigherDOSE,
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higherdose.com. They are the leader in
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LED light masks, neck enhancers, and
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other products such as PEMF mats and sauna
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blankets. If you have not gotten on the workout
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recovery train yet, your time and your stop
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is now. You gotta get these products in there before these workout recovery
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and spas end up saturating your market, having your
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members walk outta the club and going into one of their locations for
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$200. Per month where they're paying $39 to you.
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Let's become an expert in workout recovery if we are already an
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authority in workouts. HigherDOSE, check it out.
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There's a wholesale code and we look forward to
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helping you augment your products and services to meet the demands
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of your members. And hey, let's get people happy, healthy,
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and sweating, and the recovery should be just as good as the workout.
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A question for you about GLP-1s,
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longevity, IV drips, um,
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Botox, barometric chambers, those types of things. I think there's going to be
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a wave over the next 12 to 24 months of med
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spas going inside of a health club or
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studio, or potentially like a franchised
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situation where you run a yoga studio, you got an
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extra, you know, 500 square feet, you bring in a serotonin
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center that's inside. How do you view—
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could I, could I sign a sublease and like say, hey, this is a,
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you know, a separate entity, um, and they, they handle the
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liabilities? Or do you have to get, you know, additionally insured? How do you
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view that? It's, it's complex, but it's You
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can navigate it. It's navigatable.
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Everything's going to come down to the paperwork, how things are
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structured and organized, what written agreements are done between
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the parties, and what an actual party is legally allowed to do, and if they're
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allowed to provide those services. Because what I learned about lawsuits
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very early in my career as a lawyer was something that's called
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a fishing expedition, which means someone goes for treatment somewhere,
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even if it's in a yoga studio, let's say there's an IV drip and they
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have an adverse reaction, they have an allergic reaction, something goes wrong,
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whatever it is, that person will be suing everyone. They're
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going to sue the building, they're going to sue the yoga studio, they're going to
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sell the business. So, you have to anticipate that all of
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those things are going to happen. And, that's why it's important to have certain provisions
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in the agreement when you're designing to say, in the
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event that this happens, this is who's responsible. And, to have
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communication with your clients that say, hey, before you participate in this
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service, you understand A, B, and C. So, at Conscious
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Council, we call it a space rental agreement or it can be a sublease or
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a sublet. Yeah. And, those agreements are very, very, very important to have.
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And, I think that as the nature of these activities get more in the
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gray area of what's permissible, we'll see higher legal issues
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around it, which stresses the importance of having those documents in place.
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Gotcha. On a number of these
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waivers, is there anything either related to
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maybe the growth in strength training and Olympic
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squat racks and maybe some of the more
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strenuous
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activities? Have you seen people try to tighten up their waivers to
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say, you know, if you drop like a 500-pound bar on your
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back and you get paralyzed by doing that, like, it's really not on
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me. It's already covered. So the
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important thing is that the waiver reflects the activities that you do,
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the risks of those activities, and the equipment that you use.
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So typical situations that we've had problems with,
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equipment being mounted on a wall and falling off, mirrors
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falling on people, cutting people, and people getting injured
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while working with a trainer and saying that the trainer pushed them too far
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or something like that. But the waiver contemplates all of that. And the
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reason why we do specific agreements, customized
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specific agreements, is because, like, cool, if you're an Olympic
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lifting space, there are certain exercises
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we're going to specifically include in your waiver of liability as
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opposed to a CrossFit waiver and a Pilates waiver. are
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completely different. And they should be because the activities are different. So
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liability waivers of liability are always about what are the activities that you're doing
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and what are the risks of those activities and what equipment are you using in
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providing those services. Gotcha. And then from a
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standpoint of the waiver, just to stick with this
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for a minute, is that something that someone does with
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you as an example and then annually
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we have an arrangement where you guys go and update it for me, or
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do you send out notices to people saying like, hey, there's been a change in
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your state for XYZ of something that might affect your
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legal documents? Or is any of that going on or should that be going
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on? We started a membership at
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Conscious Council called Conscious Council Plus, and I started this
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in August of last year.
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And the whole idea of that is that we let people pay a membership
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And they have a constant ongoing relationship with us. So it includes unlimited
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consults, unlimited support, discounted
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prices on future services. And most of our clients
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who will get a package with us eventually will get into the membership
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because then when there's an update, we automatically reach out to them and send
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them. And then we just— like most of my clients I speak to
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on WhatsApp on a consistent basis. But to answer the question more
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directly, What you can do is anytime your
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services change, you have to update your legal agreements. So that's something that's
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really important to know. And then secondly, sometimes there is a change that will
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take place. Like recently, there's been a change with the Americans with
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Disabilities Act, the ADA, that requires
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compliance both online and in person. Whereas it
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used to be just the ADA applied to in-person wheelchair ramps
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accessibility, now it's online as well. When something like that happens, we
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send out an email to our whole community and we let people know. But specifically,
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as it relates to the waiver, the thing that you want to be in, you
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want to make sure is that so long as the activities stay the same and
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the law doesn't change, then you can keep going. But once
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you add new activities, or if there's a change in law, we always send a
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reminder out to our clients. Gotcha. And then
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in closing here, what
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would be the one word of advice for someone
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who's maybe cut some corners
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and wants to kind of get back on track, what does that
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conversation look like? Or what is my takeaways?
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It's really simple, and it's just understanding the
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value proposition of investing in law the same way there's a value
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proposition to investing with the right bookkeeper or the right accountant,
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in the same way that there's the right way to invest with anything in your
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business. And with law, eventually, it's like the one piece of
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advice I got from my mentor. He said to me, he's like, Corey, when you
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get clients, you're going to tell them, you can pay me now or you can
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pay me later. But if you want to grow a brand, have a business,
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potentially exit it, not have legal issues, be in control of the
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situation. The one piece of advice I'd say is you want to be in control
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of the situation. So many of my studios, there's
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the star teacher that decides to leave and solicits all the clients. There's
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the owner who misclassified employees and
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contractors. There's the person who's about to get sued because the waiver of
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liability didn't include something. It's like, cool, you're running a business, you're going to be
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great. Work with professionals that really understand what
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you're doing and have experience to preemptively
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evade any of the issues. And for everyone who's listening on the Halo
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Talks, the best thing to do is you can just connect with us on Instagram
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@consciouscounsel and just write HALO, H-A-L-O, in caps
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letters. And we'll know that you came from the podcast and we'll be happy to
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have a conversation and do whatever we can to support you and learn about what
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you're doing. Awesome, man. Well, we love what you're doing. We
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deal with a lot of contracts when we're doing mergers and acquisitions.
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Some of them you have a sigh of relief on and others you kind of
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scratch your head. So we're a big proponent of just get it done right
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correctly the first time, and then you actually can scale and
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you don't have that should have, could have, would have. would have, uh, if you
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actually looked at the documents prior. So thanks for coming on, man. Good to meet
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you. Safe travels. I appreciate you guys having me. Thanks so much.
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Awesome. This is Pete Moore on Halo Talks, your captain
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speaking. I am the founder and managing partner at Integrity Square.
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We've been around now for 15 and a half years. We have been
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helping people like yourselves
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00:24:14,200 --> 00:24:17,819
get capital through mergers and acquisitions, consulting, strategic
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00:24:17,819 --> 00:24:21,170
advice in the health, active lifestyle, and outdoor
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halo sector, trying to help as many entrepreneurs as
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possible get to the next level and take that inflection point
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and be the force behind your growth. We are helping companies that
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have at least $3 million of EBITDA, around $10
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00:24:36,339 --> 00:24:40,092
million of revenue, and we are positioned to help you get
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institutional growth capital. or to
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negotiate deals with strategic partners. If you go to integritysq.com/ISQ,
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you can see our capabilities deck. Happy to set up a consultation at any time
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that is free of charge, and we look forward to helping
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solve obesity, loneliness, and diabetes. Go Halo!