AccelPro | Intellectual Property Law
AccelPro | Intellectual Property Law
On Trademarks, Small Business Owners and Side Hustles

On Trademarks, Small Business Owners and Side Hustles

With Pablo Segarra, Trademark Attorney and Founder of SideHustle.Law | Interviewed by Neal Ungerleider

Listen on Apple Podcasts, Spotify and YouTube

Welcome to AccelPro IP Law, where we provide expert interviews and coaching to accelerate your professional development. Today we’re featuring a conversation with Pablo Segarra, trademark attorney and founder of SideHustle.Law.

Segarra discusses trademarks from the perspective of an attorney serving a client base of small businesses and side hustles. 

We talk about Segarra’s transition from NYPD officer to lawyer, going to law school in his thirties, misconceptions small business owners have about trademarks and how lawyers can structure their offerings for the small business market.

“Most of the clients that I work with, they're just trying to get off the ground,” Segarra says.

“I definitely recommend that attorneys that want to work with this specific clientele offer flexible pricing models, flat fee services for specific services, maybe lower your monthly retainer or give a specific amount of hours for package deals. I do that often with ideas like a startup package which includes various documents and various templates.”

Listen on Apple Podcasts, Spotify and YouTube.

Interview References:



Neal Ungerleider, Host: What are some common mistakes small businesses make specifically regarding trademarks that can be easily avoided?

Pablo Segarra: The most common mistake that small business owners make when it comes to trademarks is a failure to conduct a comprehensive trademark search. To take a step back really quickly, one of the factors that the USPTO uses to analyze your application is what's called the likelihood of confusion test.

So this determines whether one's party's use of a mark is likely to cause a confusion with consumers with another mark. Business owners often come to me and they say “Why can't I just add an ‘S’ to the name? It's different if it's Apple with a ‘Z’ or an ‘S’ if instead of just ‘Apple.’” 

But the courts take several factors into account. Things like similarity of marks and appearance, sound, connotation; similarity of the goods or services being offered; the strength of the plaintiff's trademark; evidence of actual confusion, and there are more factors. 

That's the main thing, and then I would just quickly say that when choosing an actual name, a lot of clients come to me with generic marks. Generic marks are common names for products or services that can't be trademarked because they need to be available for all to use to describe their products.

Think of milk. You can't trademark milk because everybody needs to be able to use the word. 

The advice that I always give my clients is to not be married to one name and be extremely creative with it. The way I always say it is “Think of what's the most original name that you want to give your daughter, and then give it to your product.” For some reason with daughters specifically, we get very creative when it comes to names. 

And then don't be married to that one name either. We can go down a list of products that have started as one name and changed and became something else.

Your product is not going to continue in the same manner as when you first had the idea. Don’t be married to one name because if somebody else is using that name, it may be more costly to go through litigation for the name as opposed to just rebranding.

NU: What are some steps that lawyers can take to get a better understanding of their clients’ business models and long term goals, in order to tailor trademark advice and strategies to clients’ specific needs?

PS: One step is implementing a monitoring service for our clients. I use a company that uses AI to help me do the search and implement the monitoring service.

Legal professionals can set up a trademark monitoring service for small businesses using software to scan for new trademark filings, new domain registrations, and online usage that may infringe on their trademarks. 

That's one really important step. The other one is having regular review meetings with our clients and establishing regular check-ins between the small business and legal teams. This can be vital. Understanding our review of any potential infringements that are brought up by the monitoring services is important, as is discussing the strategies for them—do we need to update any changes in the business as a result of trademark law? How does that affect the business? 

Also, just educating is important, and I like to create this kind of content. One of the things that I've learned is that clients often don't have access to attorneys every day. I think that educating clients and just simply creating 30 second, 40 second, one minute videos on social media is important. I do it to empower my clients to know more about intellectual property. It can include things like “How do I get a trademark?” It could go as specific as “Can I trademark my name?”

NU: Smaller businesses and startups might have more limited budgets. How do you reconcile providing meaningful protection for their trademarks when the client might have potential financial constraints? 

PS: My firm is called SideHustle.Law for a reason. I focus on those that have that second gig. Over 50% of millennials and over 70% of generation Z have a side hustle. They have limited budgets and limited time.

Budget constraints are super important. I take that into account anytime I offer services. I focus more on flat fees because I really do believe that a trademark is one of the best ROIs that you'll ever get with your company. It's less than a couple thousand dollars upfront and yet it protects you for possibly forever, as long as you are continuously staying up to date with it. I can't see any other ROI higher than that when it comes to business. 

The other area that I focus on a lot is this interesting intersection of technology and entrepreneurship. You have artificial intelligence coming into play that's changing the world. I do a lot of talks on that and always tell clients to use AI. Be a fan of it. Jump right into it. Use it as a thought partner. Think of it that way. 

You have some ideas that you want to run through and you don't really know who to talk to? Maybe your mentor is busy, maybe your wife is busy? Go to AI and use this as a thought partner. But in that world, it's now more important than ever that we protect the work. 

If everybody is using artificial intelligence along this linear path and it's creating the same type of results, then it's more important than ever that you protect your actual work and your authentic voice. 

I speak a lot about incorporating artificial intelligence and other emerging technologies such as NFTs. I've been working in that industry for a long time and I think there's really interesting ways to be able to conduct business in 2024, where even venture capital is looking at it differently and they're saying, “We're not going to give you as much money as we were before.” 

I think a lot of that has to do with AI, because you can incorporate artificial intelligence and other technologies into your business plan and into your business model. Before, it may have taken you a team of eight or 10 people to do it. Now, it only takes two to three people.

NU: Are there misconceptions you see from clients about artificial intelligence in a legal context?

PS: I just came back from giving a handful of talks on artificial intelligence and the law and how they intersect. A lot of clients that I deal with are definitely afraid of it, and I blame Hollywood.

You see the Terminator on the screen and we think the Terminator is coming for all of us. In reality, I don't believe that's going to happen. But if the Terminator walks in the door, we're done. What are we going to do at that point? My viewpoint is that you can look at it from two ways. 

You can look at it with a pessimistic view where the Terminator is going to control your emails, or you can look at it as an opportunity. 

I spoke to a lot of younger lawyers and a lot of law students, and explained that they are at a point in their career that not a lot of us have been at. They can enter into this path as an expert on artificial intelligence; they can bring it to the partner and incorporate it in their offices. The advice that I give them is not to look at it in such a negative manner. 

You can use AI for very simple things. For example, I put a lot of my emails to clients through AI and I just say to clear this up for clarity and make it a little bit cleaner. However, I do leave out confidential information. That is an important piece I have to stress for attorneys—not to put confidential information into these language learning models.

NU: What advice do you have for small businesses in managing trademark portfolios as they grow?

PS: Along with implementing a monitoring service, it is important to check consistently because there does come a point with trademarks where if you don't use it, you're going to lose it. We have to make sure that we pay attention to if other people are using the trademarks and then enforce your rights.

You don't necessarily have to go straight to litigation, but sending out cease and desist letters is a good example. Have conversations with the person that is about to use it. Make sure that you're speaking to your trademark attorney and that they are actually type checking the TMOGs, which are bulletins that come out every Tuesday and say that these are the people that are getting trademarks. 

Also, plan strategically. I always say that if you have an idea for a new product and you're 70 to 80 percent sure that the new product is coming out within the next couple of months, you need to trademark it because you need to protect it.

At the end of the day, we don't know what that product will morph into. It may be a huge success. It may be an overnight success. It may take five years. But if you start with the point of I'm protecting this intellectual property, then you're in a much better situation than having to look back and say I didn't trademark it three years ago and now it's a multi-million dollar business. People left and right have been stealing the idea and using the name and creating and mimicking products and infringing on my work.

NU: Do you have advice for lawyers and firms on how to package services and offerings for a small business or a startup clientele?

PS: I think that focusing on budget constraints is of importance. When it comes to small businesses, these are startups. They're dependent on where you work and who you work with. Their budgets are different.

Most of the clients that I work with are just trying to get off the ground. I definitely recommend that attorneys that want to work with this specific clientele offer flexible pricing models, flat fee services for specific services, maybe lower their monthly retainer or give a specific amount of hours for package deals. 

I do that often with ideas like a startup package which includes various documents and various templates for them. 

Also, offer educational resources such as webinars, workshops, and guides on legal topics relevant to small businesses. This not only helps educate our clients, but builds trust and positions your firm as a go-to resource for clients. 

I like to work with incubators and with women's resources groups. I just go to them and say “I want to do a webinar with your organization, I'm not going to charge you because you're going to get me in front of 20 to 30 interested clients.”

Nine out of ten times, they're interested and we do it. Having that talk, you're consistently getting in front of people and showing what you could do. They're going to reach out to you because they're going to have you top of mind when a legal question pops up.

NU: How can legal professionals best explain to clients and potential clients the consequences for small businesses that neglect trademark management?

PS: I like to focus on the risk and the benefits and highlight trust. The risk—it's definitely going through and saying “There are legal and financial repercussions if you don't properly manage your trademark. This can lead to costly litigation, potential loss of rights, and the need for rebranding if infringement occurs.”

This can significantly drain the resources of the company, but there are also benefits to it. If you have your trademarks, what are the things that you can actually do with them? 

I've worked in the crypto space, specifically with NFTs and NFT owners. I'll give a great example of the most successful NFT project in the world which is called the Bored Ape Yacht Club. They changed the game when it comes to this. They actually gave the owners of their NFT a digital piece of art that has an authenticated token attached to it which verifies that art. 

They gave them full rights. They said that as a buyer, you can have commercial use to license, use, copy, and display the purchased art for the purpose of creating derivative works based on the art.

What did the holders do with that? They created t-shirt lines. They created coffee lines. They created beer lines. They created waters. It became so popular that the Bored Ape Yacht Club actually created what's called Made by Apes. Made by Apes is a license platform where all of these licenses are on the blockchain.

It's a club where basically all of these people can go in and say “I want to buy water for my event from this other Bored Ape Yacht club holder. I'm going to go onto this website and buy that.” You can't do that if you don't have the actual license. Bored Ape Yacht Club gave the power to the holders. 

I would also say that when it comes to trust and goodwill; there's the Edelman study that came out and said over 59% of people are more likely to purchase new products when they trust the brand, even irrespective of price. When I hear that, I say “What better way to gain trust than to get a literal seal of approval from the government of the United States?” 

There's no bigger way to earn trust with your client, with your customers than to actually say “We are trademarked, we are official from the United States, there is nobody else like us, and we're going to go to lengths to protect our intellectual property.”

NU: Do you find many clients initially assume that registering a business name or domain name provides official trademark protection, or are they aware of monitoring and the other things they have to do out of the gate?

PS: I think that sometimes clients come to me with some confusion. They say “I have bought the domain name for this company, so therefore I'm protected.” But that's just not the truth. Those are two completely separate issues; you need to have both of them. I don't think there's one without the other. If you're going to create a company and create your business, then obviously you need to also get the associated domain names. 

Once the business is created, once you have that paperwork to show that you've already created it in your state, then you start going through the process of buying this digital real estate. We have to buy the domain names. We have to create social media handles. Lawyers can also come in and help out, saying that you need to get this trademark search done even before you register the business name.

I like to tell clients that before you even get to that point, give me a call. Once you have the idea, we can work through the idea and then put something to paper. I always tell them to make sure that you give me multiple names. Don't just rely on one name and say “This is the name that I'm going to use.”

Create three to five names and let’s work through them before we put something down on paper. There's a really interesting intersection here with domain names and trademarks. If a domain name is distinctive enough and used to identify the goods of services, it may qualify for trademark protection.

The name of my company is SideHustle.Law, PLLC. That is the name of the company, registered in New York. Of course I applied for Side Hustle Law as a trademark and we're in the process of going through it. I think that it's of almost equal importance when it comes to domain names as the name of your business.

NU: You mentioned, reaching out to professional associations and interest groups. Do you have any recommendations on how to find professional potential partners to work with?

PS: The first place that I started was my local bar association. I am registered in New York as an attorney. I went straight to the New York State Bar Association and the New York City Bar Association and became a member of the New York State Bar Association's task force on emerging digital finance and currency.

Through that task force, we've educated 400 to 600 international attorneys on emerging technology. Right away I'm speaking to other attorneys and I'm speaking to business professionals that are in the room. I am also a part of a few organizations that look to help out fellow Latino lawyers.

Latino lawyers in the United States are less than 6%. Latina lawyers are less than 2%. I've been blessed that my mother is part of that 2 percent and I'm part of that 6%. I like to keep that front of mind when I meet with other attorneys to let them know that there are a lot of other associations that need your help as well.

Go to your local Chambers of Commerce and just simply offer help and your services. I speak a lot with the Dominican American Chamber of Commerce and I'm working out deals to do more webinars with them. I have done webinars for local entrepreneurs that are focusing on real estate and starting a business and how to protect their intellectual property.

I would also say that going to non-profits that help empower young entrepreneurs and empower those that want to give back and create their 501(c)(3) organizations is helpful. They also need protection on intellectual property. 

NU: You were a NYPD officer for more than a decade. Can you tell us about your career path to becoming a lawyer?

PS: I joined the police department at 21 years old. At 21 years old, I thought that this was going to be my linear path in life. I was going to be a police officer, do my 20 years, retire, move to Florida and get chubby. I thought that was going to be my life.

I then had a really bad car accident at work that completely changed what I thought my life was going to be. I had to relearn how to walk, I had multiple surgeries, in and out of physical therapy for almost six years. Towards the end of my career as a police officer, I physically knew that I just couldn't do the job anymore.

I consistently ended up in the hospital from fights and chasing people. I worked most of my career in Washington Heights and it could get a little rough up there. I said, “I'm going to go to law school. I have to get out of this job.” I absolutely loved being a cop. It was one of the honors of my life. But I knew I couldn't do it anymore. 

So I went to law school at night and I was a police officer in the daytime. I graduated law school and I didn't practice law right away because I had the opportunity to organize these large scale political conferences in Puerto Rico, New York, and the Dominican Republic.

I took that experience and created a travel tech startup. I actually got into Travel and Leisure magazine for the top 50 most notable people in travel right after Mickey Mouse, which I'm super proud of.

From there, I had a really bad business partner and a really bad breakup. I needed something completely different. I got into emerging technology. I've always been a fan of crypto, but I never found the right entry point for me.

So I dove right in and I was working with a company that had to figure out Muhammad Ali's intellectual property rights and how to get them on chain in the blockchain. We went onto deal with over 50 more athletes and figuring out how to get their names, images, and likenesses created on chain through NFTs to get them new streams of income. 

With SideHustle.Law, I took a lot of that previous experience, and I felt that I have enough to be able to confidently advise founders. At this point, I’ve had about 80 to 90 founders under my belt.

NU: Do you have any tips for our listeners who might be attending law school while having stressful day jobs?

PS: Breathe. That's number one. It is very stressful. I did it for about three and a half years, and would basically say “Goodbye” to my wife on Sunday night, and then say, “I will see you Saturday, right?” You just do not see each other during the week.

Be very intentional with your time. As a part-time student, you don't really have time for internships or the traditional route that a lot of younger students may have where they have time to do internships or work in some offices that are not going to pay enough to make the rent.

Once you graduate, be extremely intentional in saying, “I am going to join these associations that I could not join when I was a student, because I now have more time.” Join your local bar associations and find the committees that really interest you.

What has gotten me through this really interesting point of being 34 years old with a whole new career and not knowing how to be an attorney to then dive head first into my own firm a few years later has really been the support of attorneys around me that mentored me.

I met them because I joined my local bar associations. You have to be extremely intentional when you come out of law school to find these events and people that you want to talk to.

NU: Can you give the AccelPro community an example of a time when a peer and not a boss or a teacher gave you help with a challenging problem in your career?

PS: My best friend, Carlos Martinez, is also an attorney. He’s a bankruptcy lawyer who helped guide me as to how to be a lawyer because I didn't have a traditional legal background.

I've been studying law since I was 20 years old, but not as an attorney. I called Carlos right away because I said “I have this job with this company called Blockasset. We have a lot of athletes on the roster and we need to figure out how to piece together their licensing deals. That way they're getting paid to be able to give us their name, image, and likeness to create these NFTs for them, this artwork”

I was working with one of the attorneys for the company, which was based in England. But Carlos was the one that really stepped in and helped me a lot. He's the first person I called.

I said “How do I approach this client? How do we have these conversations? How do I even figure out how much my time is worth?”

Listen on Apple Podcasts, Spotify and YouTube.

This AccelPro audio transcript has been edited and organized for clarity. This interview was recorded on March 18, 2024.

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AccelPro | Intellectual Property Law
AccelPro | Intellectual Property Law
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