Jamie Lieberman Transcript

Ever signed a contract and realized later you missed some legal fine print that cost you dearly in your business or life?  Sadly a lot of entrepreneurs don’t get the advice they need at varying stages of their business growth.


I’m Melinda Wittstock and today on Wings of Inspired Business we meet an inspiring entrepreneur who is leveraging her legal expertise as an entrepreneur helping other entrepreneurs avoid the sort of legal landmines that can stop you in your tracks.

Jamie Lieberman is the founder of Hashtag Legal serving influencer marketers, creatives and e-commerce companies. A practicing lawyer and entrepreneur for 15 years, Jamie understands the unique needs of business owners at different stages in their organization’s growth and scaling.

Hashtag Legal helping entrepreneurs, in particular influencer marketers, avoid legal landmines. She believes the traditional legal system is broken, so she has innovated an integrated approach to servicing her clients – understanding their business objectives and providing legal advice and support to ensure they can protect their businesses. Jamie brings extensive experience drafting and reviewing contracts, advising clients on intellectual property issues, drafting website and mobile application terms and conditions, advising on business formation and negotiating on behalf of clients.

Prior to founding Hashtag Legal, Jamie worked for a large, international law firm in New York City as a commercial litigator and for a Federal District Judge on both civil and criminal federal cases – as well as Director of Operations and Chief Counsel at an influencer network.

She regularly speaks about legal matters, the art of negotiation and entrepreneurial topics at leading industry events such as Alt Summit, Podcast Movement, and FinCon and she is the co-host of The FearLess Business Podcast.

So let’s put on our wings Jamie Lieberman.

Melinda Wittstock:         Jamie, welcome to Wings.

Jamie Lieberman:            Thanks for having me.

Melinda Wittstock:         I’m excited to talk to you. You’re disrupting the whole legal establishment. So many industries are changing so fast, but you’re virtual, and you’re all women. What was your inspiration to take on the law, if you will?

Jamie Lieberman:            So, I’ve been a lawyer for about 15 years. And the first half of my career was the very traditional legal practice. I worked at big law in New York City. I worked for the federal government. And while I loved law school and I loved being a lawyer, that didn’t fit me. It just felt off. And so I was searching. You know that you have that feeling that you have when you’re like, I know I’m on the right path, but I’m not quite sure I’m in the right space.

Jamie Lieberman:            And so I just left. I decided I’m going to try to figure out what I want to do. And for a little while I thought that meant leaving the law. And so I freelanced for a while. About seven years ago I left. And that coincided with the birth of my first son. So that was really the catalyst. I knew there had to be a different way. So I just freelance because I didn’t honestly know what it looked like, but I knew I needed to make a change.

Jamie Lieberman:            And as I started to freelance and look around, I realized that there were so many lawyers out there that were just not happy. And I started looking at what that looked like. And what that really looked like was this lack of autonomy and this lack of feeling that you had sort of control over your schedule, your life, what area you practiced in. So much it felt like was being fed to young lawyers as you just have to be happy with whatever you got because you’re lucky you have a job. I didn’t like that, and I thought that there needed to be more power in it.

Jamie Lieberman:            And so when I started deciding that I was going to take on clients and create my own law firm, I remembered back to a conversation I had with a boss when I went to them, and I said, “Hey, I had just had my first son, and I would love a little more flexibility. I’m totally into work. I want to work. I want to work full time. I’m willing to put in the hours, but I’d love maybe a day a week at home.” And that lawyer looked at me. And said, “It is impossible to make a profitable law firm where people are flexible.” And I thought, challenge accepted.

Jamie Lieberman:            So I did that. And I decided, you know what, I think that’s wrong, and I actually think you’ll be more profitable if you give people autonomy and flexibility and trust, and allow them to, knowing that there’re strong standards and that this is a business and clients need to be served, but allowing them to do it in their own space, and giving them the tools to do it. And as it turns out, that lawyer was wrong.

Melinda Wittstock:         Absolutely. I mean I see that transformation happening in a lot of businesses that the best team members are not motivated only by money. And that’s not the only way to reward. So things like flexibility is so critical for women especially, but I think increasingly for men too, and other benefits besides. And so did you find it quite easy to then find top female talent because of that in your firm?

Jamie Lieberman:            So yes and no, which is very interesting. When you’re hiring virtually, it’s really harder to connect with people. So we have a lot of interest. Anytime we post a job, we get a lot of interest. But my job, the thing that I need to do and the responsibility on me is to get through all of that, and find the actual right fit. Because it really does take a special person who is able to work on a virtual team who you can trust as much as I need to be able to trust them.

Jamie Lieberman:            So lots of people are interested, but when you dig deeper, you can sometimes find they actually need to go into offices, or want to go into offices, or think that they’re going to be able to do the work while having a young child at home, which is not possible. Or that they’ll have flexibility, meaning they can just take off for the day and not tell anyone. So we have to have clear boundaries, and it takes a lot of effort on my part to make sure we find the right fit for the team.

Melinda Wittstock:         Yeah. And so do women in law generally operate differently from men, or is that just such a big generalization? When I think about when we’re really leveraging our feminine power, so I’ll define that kind of in an archetypal sense of our intuition, our empathy, our relationship, our collaboration skills, all these sorts of things. How does that play out in your law firm, virtual, women only as opposed to all your experience in the big New York and federal government kind of scenario.

Jamie Lieberman:            In my experience, all of those things that I think make women great is squished in the very typical traditional law firm. It is not encouraged, or it wasn’t at the time. I haven’t been in those places in quite some time, although I do talk to a lot of lawyers, and I’m not sure it’s changed very much. But that type of feeling and thinking and the way of doing business was never encouraged.

Jamie Lieberman:            And frankly, you were really basically told to act like a man, which I thought never made sense to me. I think a lot of those traits are actually what makes us great counselors, and truly makes us great partners with our clients. And so if you come from a place of empathy and problem solving, it really allows you to form really strong, loyal relationships with clients. And I think that’s what being a lawyer is all about. The focus in many of these traditional law firms is so much on the bill, bill, bill, bill the hour, bill the hour. And that, I think doesn’t do great service to many clients.

Melinda Wittstock:         No, it doesn’t. And my goodness, you’re actually talking about putting the customer first. They actually matter. I mean I know that because you’re legal bills, especially in business, they can just, oh my goodness, just escalate so fast just on terms of documents, or whatever it is. And you get that feeling like, oh my God, you’re being billed. And to me it feels like, because I’m so woo-woo, it just feels like scarcity mindset.

Jamie Lieberman:            Yeah. I 100% agree with you. It offends me when a client comes to me and tells me something. I’m not kidding. I actually feel really upset by it. I see these quotes that clients get from other lawyers, and I’m like, that is robbery. You should not be paying. I’ve had clients come to me to fix problems that other lawyers have done, and they’ve told me what they’ve paid these lawyers. And it just guts me. I’m like, that’s not right.

Jamie Lieberman:            A lot of my clients are small business owners, entrepreneurs. I mean many of them have large businesses that are really lucrative. Definitely seven, eight figure businesses. Some nine. And so they have the money, but that doesn’t mean that that’s the best place for them to spend it.

Melinda Wittstock:         So many things are kind of, I don’t know, templatized now. I know in the early stages of some of my startups, being in an accelerator or shared office space, “Hey, anyone have a good independent contractor agreement that you can share?” Right? And you had to do that because in the startup phase you didn’t have money for all these big kind of legal bills. So how do you see the law evolving in the sense of where is it lucrative, and where is it being disrupted just by technology, and the fact that we can easily kind of templatize some of the more basic aspects?

Jamie Lieberman:            Yeah. I actually encourage my clients, for the things they can do themselves, to do it themselves. But I think it’s important to have a good working relationship with a lawyer you trust who will say to you, “Don’t do that yourself,” or, “This doesn’t quite work with the template,” or, “Yeah, I’m okay with that template,” or, “If you’ve got a template, let me at least take a look at it and see how I can customize it for you.”

Jamie Lieberman:            I’m not a huge believer in templates. I do understand that sometimes that it’s either a template or nothing, and I’d rather see a template than nothing. Because really truly there are certain boiler plate things that go into, say, an agreement. But there are also some really customized parts of that contract. And that is sometimes where the contract rises and falls.

Jamie Lieberman:            So I think where lawyers need to give them most value, and where many lawyers fail at this, is the counseling, is the honest plain language. Tell it like it is. I have an understanding of what your business is. I know where you’re going, and I know how I can best help you. And that is a true equal partnership. I think a lot of lawyers, and frankly many business owners, put lawyers on a pedestal. And they think they’re better, or they know more. And that’s just not true. You should truly be partners. Your lawyers should understand your business. You shouldn’t have to explain it to them, and you certainly shouldn’t have to pay them to explain it to them. And they should really know what needs to get done to protect you.

Melinda Wittstock:         What do you think are some of the biggest mistakes that people make in the early stages of business? We’ll start with the early stages, and then move up, right? But so say for instance, anyone who’s listening to this podcast is a solopreneur. They’re in the kind of early phases. They’ve turned their side hustle into their dream thing. They’ve quit their job. They’re really on the entrepreneurial up ride, right? They’ve got some customers, that kind of stuff. What are some of the mistakes that you often see folks like that make?

Jamie Lieberman:            It really is ignoring legal. I mean, usually that’s what happens. Money has to be spent. And so sometimes I’ll see someone spend money on another service that they need, and it could be a really expensive service, but they haven’t taken the time to really balance that with there are legal needs, or accounting, or some of the less sexy things that make you feel like, oh, I’m not making any money from it.

Jamie Lieberman:            And so I see people choose names without clearing them. I see people utilizing template contracts that maybe don’t fit the relationship. And then, it gets bigger and bigger and bigger, and suddenly someone comes and says, “Oh my gosh, I’ve been in business for three years, and I’ve never had a lawyer look at any of this.” And then it ends up costing more because we’re undoing a whole bunch of things that could have been done correctly the first time for a lot less.

Jamie Lieberman:            And I think because of there’s so much fear around talking to lawyers, and because people don’t even know where to start, right? You don’t want to Google your lawyer even though people do it. And so sometimes you don’t even know where to look or who to ask. Or maybe you are doing something different. Maybe you have a nontraditional business, and you’re like, I don’t even know that there’s a lawyer that knows what to do. And that is really where I see, they just ignore it rather than trying to tackle the problem head on.

Melinda Wittstock:         Right. So it’s so important to do this right out of the gate. I mean, just even your organizational documents, things like trademarks, if you have an online business, making sure all your privacy bit is done. I mean, there’s so many things that are really important to get right.

Melinda Wittstock:         We have a lot of listeners who are really busy scaling their businesses. So in that they’ve gotten to $1 million, they’re in that thing between a million and three. Or, they’re in the zone between three and ten. I know from scaling businesses, it’s also, you got to be different people at these different stages. And so at those different stages, what kind of legal do we really need, say, at the one-to-three, as opposed to the three-to-ten, and beyond?

Jamie Lieberman:            Yeah. I love how you put those. Those are so perfect. The one-to-three, three-to-ten.

Melinda Wittstock:         It’s true. Right?

Jamie Lieberman:            It’s so true. That was so good. There’s really two ways that you’re doing that, right? You’re scaling based on workforce, or you’re scaling based on partnerships because you’re not doing it alone. Even if you want to, or you try really, really hard, there’s just no way to do it by yourself.

Jamie Lieberman:            Scaling in a workforce, particularly in these online businesses, there’s a lot of virtual workforces out there. And so if you have employees/contractors, one, knowing the difference. So many people start off with a workforce of contractors, and then quickly they hit one million, and they’re like, oh wow, these are probably employees. So converting from contractor workforce to an actual employee workforce.

Jamie Lieberman:            And then what does that look like? What are the HR legal implications? So having someone who has good employment background who can help advise you, particularly if you have employees all over the country because every state is different. We all know California in particular is a…

Melinda Wittstock:         No, you can’t have freelancers there anymore.

Jamie Lieberman:            Not so much. It’s a pretty narrow definition for that now. So yeah. So I think workforce and really being on top of what that looks like and making sure that you have really good documents in place, manuals, employment handbooks, policies, knowing what’s going to happen. I’ve definitely had clients who’ve scaled and hit that moment, and then something happens. Whether there’s a harassment issue, or things start to come up. And so that really blindsides people.

Jamie Lieberman:            And the other is just the larger the deals that you’re entering into, say whether it’s suppliers, or you’re partnering with someone, and these numbers are getting bigger and bigger as your income goes up. Just knowing those contracts are going to get more and more complicated. So having someone who can read them with you and talk to you about not only the terms of it, but help you negotiate those terms. Because every contract should be negotiated. So someone who truly understands your business is really important. And those are the two big ways I think that people tend to scale in those ranges.

Melinda Wittstock:         Yeah, that’s such great advice. So when you were a little kid, Jamie, did you know that you were entrepreneurial? Because I have to ask this because sometimes the idea of a lawyer and an entrepreneur is kind of an oxymoron to a lot people. Right?

Jamie Lieberman:            True.

Melinda Wittstock:         And so, I’m curious which one came first in your life, as a little girl you were going to be a lawyer, or were you really entrepreneurial? Did you have the lemonade stand and all that?

Jamie Lieberman:            I was neither as a little girl if you can believe it. I was really artsy, I took photographs, and all I wanted to do was create, which is really funny. But I was also really good at math and science. So my brain always went in 100 directions. So I guess I would say I was probably more inclined to be entrepreneurial even though I really pushed against starting my own business. Even in law school when I finally figured out… I didn’t go to law school till I had about five years of working experience. So I had a whole career prior to going to law school. And so I really pushed back against law school. And then I also really pushed back against opening my own business. And then eventually I’m like, well you know what, nobody’s going to do this so I got to do it.

Melinda Wittstock:         Isn’t that interesting that so many of my businesses have started that way too? Because you look around for something and say, wait, we really should have this, or somebody should do something about that. And then you realize that nobody is. And then you sort of think, God, well there’s actually a real market for that. Hence, my fifth now is a podcasting network because as a podcaster I realized, God, I don’t know anything about my audience. I know they’re entrepreneurs, but I don’t actually necessarily know them, and what they like and dislike

Melinda Wittstock:         It’s that lack of data to be able to monetize with advertising and sponsorship because it’s total guesswork for the advertisers. and nobody shares the data and advertisers aren’t getting it either.

Melinda Wittstock:         And I’m like, wait a minute, someone should do something about it. Oh, I know, me. My media tech background. Right? And so as a result now of this gamified podcaster engagement network will be the first to share revenue with podcasters. And it’s interesting you sparked something when you said, “God, I looked around and no one else was doing it.” And people ask me things like, “How come this doesn’t exist before?” I guess my only answer is you haven’t met me. Right?

Jamie Lieberman:            Exactly. I mean, I will tell you that my husband’s an attorney, and he’s a partner at a very traditional law practice. And sometimes I go to events. And his partners look at me like I have six heads. They’re like, “Your practice is what? Who do you represent? What do you do?” I’m like, keep not knowing. It works for me.

Melinda Wittstock:         Yeah. Well you know what’s interesting about that actually that a lot of men, you know their brain, I don’t know, they’re very singularly focused, right? Tend to build businesses that are kind of A to B. And then women though tend to see the connections and connect the dots. And so I’m beginning to see that women create slightly different business models where all those dots connect and it makes sense in our brains.

Melinda Wittstock:         We know where the hubby’s socks are, and we know where the kid’s thing is, whatever. Our brains work a little differently. And so when describing this to men, they’ll often say things like, “Oh, that’s too confusing,” or, “Can you focus?”

Jamie Lieberman:            Yes.

Melinda Wittstock:         I am focused.

Jamie Lieberman:            Exactly. Yeah. No, I think I’m also leading with the empowerment of my employees and my clients, frankly. And I don’t typically think men think that way because they honestly don’t have to. They’ve been empowered their whole lives. So I’m just coming at it from a different viewpoint because I’ve sort of had to fight to be able to be myself in a profession that has a very specific archetype of what you’re supposed to be when you’re a lawyer. When people meet me and see me, the first thing they say is, “You don’t look like a lawyer.” And I’m like, “Thank you.”

Melinda Wittstock:         So they’re expecting somebody really kind of hard charging and aggressive? It’s almost like-

Jamie Lieberman:            Conservative.

Melinda Wittstock:         Right. All the TV dramas about kind of how you’re supposed to be.

Jamie Lieberman:            Correct.

Melinda Wittstock:         So that’s interesting. So how do you navigate that? So if you come at it in a more kind of authentically feminine way, and I don’t think feminine and power are an oxymoron.

Jamie Lieberman:            No,

Melinda Wittstock:         Right?

Jamie Lieberman:            They’re hand in hand.

Melinda Wittstock:         Hand in hand. So when we’re really in that 100%, we actually are unstoppable, I think, right, when we actually leverage it. I think we can get really derailed when we try and be men. I don’t think that works for us. It’s inauthentic first of all, right? But those skills were always sort of demeaned a little bit. It’s like, oh, those are soft skills, or whatever. Right? And so how do you navigate that? I can imagine you get misjudged quite a lot.

Jamie Lieberman:            All the time. First it’s whether or not I’m somebody’s assistant. Get that a lot. Or the court reporter as when I was a litigator. To be honest, I find it funny now, but only because it’s been so long. I mean, when you’ve been doing something for 15 years, and I now have the confidence in the fact that I am a great lawyer, that doesn’t even derail me.

Jamie Lieberman:            But really what I find so much strength in it is because I’ve really learned that I’m not for everyone. And that’s okay. And that’s great. If I am a fit for you, I am definitely a fit for you, and we’re going to work together for a really long time. If I don’t resonate with you, that is completely fine. I can’t be everything to everyone.

Jamie Lieberman:            And once I stopped trying to be, it was the most freeing thing. I became so much more vocal in who I am, and what I can offer, and why what I offer is great. And if that works for you, we’re going to be great. And if it doesn’t, let me help you find someone who it will. I don’t want that for either of us. It’ll be frustrating for you, it’ll be frustrating for me, and it just won’t work.

Jamie Lieberman:            So once you embrace that and you say to yourself, okay, this is who I am, I’m strong in that, and if it works for you, let’s do this. And if it doesn’t, it’s not personal. It’s business. It’s okay. It’s also not a statement on my personality, or who I am. It just means we’re not going to fit in this way.

Melinda Wittstock:         That makes so much sense. Yeah, that makes so much sense. And I think people respect that as well. It’s just really having the courage to be authentic and be yourself. And what better a way to do that then to be an entrepreneur because you get to do that.

Jamie Lieberman:            It’s my company. I can do whatever I want.

Melinda Wittstock:         Exactly. So what’s the sweet spot? What’s your area? Does your firm have a specific area of expertise that you focus on, or are you basically do all kinds of things?

Jamie Lieberman:            We really act like outside general counsel to clients who don’t have an attorney that’s in-house. And that can be someone who’s just starting up. Two companies that have been around for a while, and they’re in that scaling that you’re talking about. Or they’ve scaled, and they kind of are where they’re going to be and want to be.

Jamie Lieberman:            So we do anything from business formation to business structure, contracts, intellectual property, we do employment, all of that. We do work in the online space. So we do a lot of privacy as well. Privacy is a very hot button topic right now. Terms and conditions for app developers or tech companies. We do a lot of that as well. So really, it is we’re all across the board. And I have specialists that work for me. I have an intellectual property attorney that works for me. I have a privacy attorney that works for me. So we’re able to provide those services.

Jamie Lieberman:            My background was, like I said, litigation. I did complex commercial litigation and employment litigation. So I have an employment law background as well, which serves us well. So really wherever the client is, we’re sort of able to meet them. And if I don’t have someone on staff, I will partner with another attorney to make sure we can get that happen. So we have a really good network of contractors and other experts who are able to help us out. If a client comes to us with something, and we’re like, “You know what, that’s not a good fit for us, but we’re going to find you someone who is.”

Melinda Wittstock:         And so what’s the big vision? Where do you see your firm going over the next decade? I mean we’re here in 2020, and we’ve got 2020 vision. Where do you see yourself a decade from now?

Jamie Lieberman:            These are the questions that make my heart hurt.

Melinda Wittstock:         I’m sorry.

Jamie Lieberman:            People ask that, I’m like, oh my gosh, 10 years from now. I have no idea. I am really big in education. I’m really big in when people have knowledge, I think they have power, particularly around the legal field and generally in business. Because I have clients from beginning to scaling to failure to thriving. I see it all. So I actually have a really unique position as an attorney who partners with growing entrepreneurs that I get to see everything because the lawyer hears everything.

Jamie Lieberman:            So I’ve learned a lot just about growing and scaling businesses. So my hope is we continue to grow as a law firm. We’re in a really great position now where we get to pick our clients. So I feel very lucky about that, that we’re not in the scarcity mentality like you talked about that we’re able to say, you are a fit, you aren’t. So not everyone that comes in the door is going to sign with us. And that’s a good feeling. Because I know my clients are a great fit.

Jamie Lieberman:            But I want to be educating people more. I want to be talking more about these topics like negotiation. That’s a big one for me. I give a talk about negotiation, and I really want to expand how much I’m talking about it. I want to create information products for people that are not only legal in nature, but also in business. And a lot of the things that I’ve learned as an attorney over the last 15 years that I think can be really beneficial to someone who’s starting and scaling a business.

Jamie Lieberman:            And I also want to create something, because a lot of times, like you talked about earlier with people don’t have money sometimes when they’re starting up, but they need information. And so I want to create certain information that people can get when they may not have the money to hire us, but they do need something, something to guide them. And I feel like there’s just nothing there. It’s either you hire the lawyer, or you got nothing. And a lot of the template and really sort of inexpensive groups, they just don’t work. And I’ve seen them, and I’ve looked at the information they’re giving, and it doesn’t work. So I think there’s something missing there, and I think we’re going to create it.

Melinda Wittstock:         That’s amazing. Well thank you so much Jamie for putting on your wings and flying with us. I want to make sure that everybody knows how to work with you and find you.

Jamie Lieberman:            So the firm is Hashtag Legal. Our website is hashtag-legal.com. You can find us on Instagram at hashtag_legal. And you can email me directly as Jamie, J-A-M-I-E, @hashtag-legal.com.

Melinda Wittstock:         Fantastic. Jamie, thank you so much. It’s been a delight to talk with you.

Jamie Lieberman:            Thank you. This was great.

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Listen to learn the secrets, strategies, practical tips and epiphanies of women entrepreneurs who’ve “been there, built that” so you too can manifest the confidence, capital and connections to soar to success!
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Review on iTunes and win the chance for a VIP Day with Melinda