Small Business Spotlight: Reporter and Entrepreneur Lindsay Hoffman on Chasing Success

Jul 10, 2020

The inspiring Lindsay Hoffman recently joined us for an episode of Small Business Spotlight!

Lindsay is an award-winning entertainment/wellness journalist, motivational blogger, and entrepreneur. As a reporter and host, Lindsay has been working in the field for over 8 years and her work has been featured in InTouch Weekly, Life & Style Magazine, Closer Weekly, US Weekly, and more.

Lindsay produces a motivational blog and show called Dose Of Bliss, where she interviews celebrities, influencers, professionals, and everyday people for their tips in personal growth,wellness, and manifestation.

Lindsay also owns the media company LBH media. There, she acts as an influencer marketing consultant and produces experiential influencer events. Lindsay works with companies like Adobe, IMAX, Patron, and more.

It’s Lindsay’s mission to bridge the gap between traditional and new media and while doing that, she hopes to inspire the world one person at a time.

On this episode of Small Business Spotlight, Lindsay shares some excellent tips for success, including the power of persistence, building and growing a professional network, staying on top of taxes, and adapting to changes brought on by the Coronavirus.

Andrew also joined Lindsay on Dose of Bliss to share the Money Habits of Successful People. Watch the interview here and read the blog post here!

Navigate the Video

  • 00:34: Career beginnings and working as an entertainment reporter
  • 01:52: Applying journalism skills to marketing and freelance life
  • 03:04: Inspirational guests on Dose of Bliss, including Brandon Farbstein
  • 04:04: Tips for success: Make your time worth more money
  • 05:48: Pitching yourself and building your network
  • 08:19: How the power of persistence led to a $100,000 opportunity
  • 09:19: Handling taxes as an independent contractor
  • 13:11: Adapting to Coronavirus: How to creatively maintain revenue streams
  • 16:35: Turn a “no” into a “yes” & keep the money coming in
  • 17:04: Tips for success: Trust yourself and take risks

Full Video Transcript

Andrew Gordon: Hi everyone. My name is Andrew Gordon, and welcome to another episode of our Small Business Spotlight. Today, we’ve got another great guest, Lindsay Hoffman. Lindsay is an entertainment and wellness journalist and an entrepreneur. Lindsay, welcome to the show.

Lindsay Hoffman: Thanks for having me.

Andrew Gordon: So Lindsay, I guess to start, why don’t you tell us a little bit about what it means to be an entertainment and wellness journalist, and also about some of the entrepreneurial activities that you do?

Lindsay Hoffman: Yeah, as an entertainment and wellness journalist, I started my career working for a couple of national magazines: In Touch Weekly, Life & Style, Us Weekly.

I was full time for a few years, and then I decided to go freelance. And once I went freelance, I decided to work on my blog, which is a motivational blog called Dose of Bliss. I created my own business called LBH media, where we do influencer events with digital influencers and we bring brands together.

It’s been a really cool dynamic, once you go freelance, that you can also become an entrepreneur and have your own business and get the best of both worlds.

Andrew Gordon: Tell us a little bit about your background and your path. How did you arrive in these fields?

Lindsay Hoffman: I went to college, actually, to be an interior designer. It was always my dream to do that. But the school, they said, I talked too much and I… Not in a bad way. I just liked to present projects to the class, and they could tell I was so passionate about doing that. They said maybe I should find a career where I’m presenting and talking to people more.

When I met with my advisor at school, they said I should go to the journalism school because it seemed like I wanted to do some sort of marketing. I remember when I was younger, I always wanted to be a TV host. I just thought you had to have an agent—that you had to be lucky. I didn’t know journalism was a thing.

The journalism school was a way to learn how to be a journalist, but also learn how to do marketing. They’re very similar because when you’re a journalist, you have to be a go getter. You have to cold call people, just like anything in marketing when you’re wanting to get a deal. You have to learn to negotiate with people who don’t want to tell you their story.

Especially in entertainment news, you’re dealing with people at the top of their game, like in Hollywood with celebrities, with people who want something from you. So you have to figure out how to be a resource to other people to make them tell you what you want to know, but make them feel like they wanted to tell you that and feel happy with it in the end.

I took all of those skills. And once I went to go freelance, I now knew how to negotiate with people, how to talk to high-profile people, and I had also met all the big players in the industry and wasn’t afraid. So that’s kind of how it all went together.

I kind of just copied the people I admired at work who would always get these big, exclusive gossip stories for the magazine. There’s this method of talking to people so you get what you want, and if you can deliver what they ask for, that’s where the sweet spot is.

That’s where I kind of took everything I learned into my own business.

Andrew Gordon: Sure. Sure. So, your video series and your blog is called Dose of Bliss, right?

Lindsay Hoffman: Yeah.

Andrew Gordon: Can you share with us some of the guests that you’ve had?

Lindsay Hoffman: Actually, my favorite guest I’ve had so far was someone named Brandon Farbstein. He’s a motivational speaker. My dream is to be like a millennial Oprah, and Brandon Farbstein is—he’s like the next Tony Robbins. I’m so happy I got to meet him.

He’s, I think, 20 years old now. And he was bullied for having a rare form of dwarfism and wanted to commit suicide because it was so bad, but he got the help that he needed.

And because he got the help he needed, he was able to use himself as a voice, become a motivational speaker. Now he talks to major businesses and the people who were bullying him are asking him for a job.

So we have people like that on the show, sharing their story and how they got to where they  are.

Andrew Gordon: And it sounds like overcoming adversity and still achieving great things.

Lindsay Hoffman: Yeah, nothing can stop you if you want to achieve something.

Andrew Gordon: Yeah. Yeah. It sounds like you’ve talked to some very impressive people and gotten some great life tips along the way, but what is some business advice that you’ve picked up and applied to your own business?

Lindsay Hoffman: My favorite tip I ever got, actually, was make your time worth more money. Every person I’ve ever talked to, who I look up to, says that. And the reason for that is everyone’s always trying to work more and more and more, so they make more money. But if you make your time worth more money, you can work less and you can make more money.

All you have to do is be really good at what you do and build relationships with other people. Once people trust you, the money is there. They want to give it to you. You just have to prove to them why.

So that’s what everyone says, like do less, get more. Work smarter, not harder.

Andrew Gordon: Yeah, and show value. People are willing to pay you for that.

Lindsay Hoffman: Yeah. As long as you can show that value, because at the beginning of doing this, I was working in the influencer industry in, like, 2014 when no one really knew what an influencer was; there was no regulation.

I didn’t completely know everything I was doing. People don’t always trust you and they want to know that you can deliver. But now that I’ve been doing this for about five years, now I’m on phone calls with people like Disney and they’re like, “I’ve heard of your event. I really respect what you do and I want to invest in it.”

Versus the beginning, when I started, I was also nervous, ‘cause I was like, “I really want to make sure I deliver. I don’t 100% know what I’m doing, but I know enough to make something happen. I’ve done enough research. I know enough people. I’m sure I’m going to deliver.”

But now I have the respect that people will now give me the money and I can get the big brands, and now people are talking about it. Once you can deliver and prove, and you don’t give up on what you’re doing, then people start coming to you.

Andrew Gordon: Right. It sounds like now, over time, you’ve developed the experience, the portfolio that you could present people, that Disney will answer your calls. But do you have any advice for people that are perhaps just starting out that don’t have those experiences yet and are trying to get people to answer the phone?

Lindsay Hoffman: You really have to just go for it. What I do is I make a spreadsheet and I Google everybody I want to know. You can usually Google, like, “Disney press release,” and at the bottom it will say their email and their phone number and their name. So I just make a whole spreadsheet of everybody I want to know.

And then it’s really important you make a deck. You don’t want to just email people and not know what you’re asking for and not sound professional, because they get millions of emails every day. There are all these people who are fake and lying, like Fyre Fest, or just sending random stuff. They’re going to ignore that email. You don’t want to be that person.

There’s something called the deck, which I didn’t even know what a deck was. I asked someone in the marketing industry to give me an example of one from Coachella. I basically just copied it at first until I started realizing different things. And you can Google what to put in a deck.

I look at it and I think to myself, what am I delivering to this person? I ask all those questions to myself. Once those questions are answered within myself, that I would pay the money to do it, then I know that someone else will. So I put it all together and I just cold call people. I just mass email lots of people.

It’s still not easy. For every, like, 600 people I email, like three people will respond and maybe one of them will sponsor my event. And you have to email some of them, like up to 10 times to get an answer. So even if you have experience, it’s not necessarily easy. You can do it any time, but you really do have to back up what you’re saying and have evidence of why they should do this and to show them what it is.

Andrew Gordon: It seems like persistence alone and volume isn’t enough, right? You can send all the emails you can, but you need to also be able to set yourself apart and use things like decks. If you have someone’s attention only for a short period of time through an email, those types of things can really set you apart.

Lindsay Hoffman: Yeah, they really do. I also make my emails really short. Like one or two sentences and something they can answer “yes” or “no,” because no one’s going to read a big email.

I make my subject headline exactly… like I literally just will call it, “Time-sensitive influencer event.” So that way they’re like, “Oh, this is a time-sensitive influencer event. Let me open it.” I make it simple like that.

Being persistent also does work over time, as well, because I had been emailing someone I had met who worked for Pizza Hut for probably five years. I had met him in person just once and had his contact information. He would read my emails, but I don’t know if he fully took me seriously, because he didn’t know me really well.

Finally, after like five years of emailing him, he connected me directly with the people at Pizza Hut and let me do a pitch for a $100,000 deal. He just said, “Hey, we have budget, $100,000 to use up by the end of the year. Do you want to pitch?”

So the more you email, like if you email someone for five years and you’re being relevant and they see you’re doing the same thing, and you’re constantly growing, they are seeing it. Then a meeting comes up and they say, “Do you know someone who does this?” They’ll give you that chance after all that time.

I had that opportunity, and this happened from sending emails.

 Andrew Gordon: Yeah. You never know when that opportunity may arise.

Lindsay Hoffman: Yeah, it took a couple years, but they’ll think of you.

Andrew Gordon: So let’s talk a little bit about everyone’s favorite topic: taxes. It’s my favorite topic, so it must be everyone’s favorite.

You’ve been a freelancer, which means, just by its nature, you’re an independent contractor rather than an employee. You’re not getting a constant paycheck with taxes withheld, but you’re considered an independent contractor for tax purposes. And this is a challenge for a lot of people that we come across.

Did you have to learn any lessons the hard way, or how did you stay on top of your own tax requirements?

Lindsay Hoffman: I’m really lucky that I personally didn’t experience anything the hard way, but that’s because I’m fortunate enough to have a dad who’s an accountant. He’s always in my ear of what to do, ahead of the game. I kind of have my built-in personal finance person who can give me insider information that not everyone can have.

But I want to learn to be really good with all of these things as well, because I’m not going to have my dad to do this forever. And whether or not someone gets their own personal accountant, you should always understand what’s happening and know that you can ask questions.

So, what I do as an independent contractor is I do my estimated taxes. I estimate how much I’m going to make for the year, and I pay that quarterly.

The way I estimate it, to make it easy, is I make an Excel spreadsheet, which is like my favorite thing to do, and I write down as I make money. Whatever I’m making, I just put down what it is, what day I got it, where it’s from, if I’ve deposited it. And I just add up the sum.

And I also… save all of the documents. I put a date of when it’s paid and I put it inside my drawer so I can always look back into it. Because sometimes, the IRS or somebody will come back to you saying you didn’t pay something and I can just pull it out and be like, “Here it is,” you know? And then sometimes you get money back, and that’s nice.

But back to how I estimate it: I go through that and every year, when you’re looking at it like that, you know how much money you’re making. For example, this year I started making more money than I had made the other year, so I can kind of project what it’s going to be through the year, what I’m going to make. I’ll put in the estimated taxes and then I’ll pay that quarterly. And I’ll estimate a little bit more. It usually even evens out by the end.

If I’ve estimated a little bit too much, then you get a nice refund at the end, which is nice because you feel like you’re making more money.

In LA where I work, a lot of people are independent contractors, and I know a lot of people in the YouTube world, and it’s surprising that people don’t know that you can pay your taxes quarterly.

A lot of people out here, they’ll wait till the end to pay their taxes and they’ll have a huge lump sum that they have to figure out to pay. Some of them can pay that and some of them can’t, and then you get penalties. And it’s just a big problem, when you can just be taking it out, almost like how a job does, throughout the year and then not worry about it or get your money back. So that’s what I do.

Andrew Gordon: Yeah, and that’s great advice. We see those same issues all the time, especially with independent contractors, sometimes those in the entertainment field, because there isn’t anyone taking money out of their paychecks. It’s up to you to budget for yourself and put money aside for taxes.

And you’re absolutely right. Some people, at the end of the year, can pay it, but sometimes you can’t.

Some businesses, actually, you’re required, as an independent contractor, to pay it quarterly. And that is something that people don’t even know.

Lindsay Hoffman: Yeah, it’s mind blowing, especially people I know in the YouTube industry, and those people started really young. If you’re like 17 and you’re making $30,000 a month on YouTube, you have no idea anything about taxes. I’m still learning things about it, but there really are these hacks.

Andrew Gordon: And it just makes life so much simpler and without fear of taxes at the end of the year. I think that’s great advice. Thank you for that.

So, we’re on Zoom. Maybe, had this been a year ago, we would have been in person. Things are definitely changing and have changed as a result of the Coronavirus pandemic. How have you and your businesses adapted to the pandemic, both in terms of your blog and your website, and also the event company?

Lindsay Hoffman: I’m glad that I’ve diversified in different places because as a journalist, I mainly cover events, and those are all gone. And from the event aspect of what I’m doing, it’s kind of on hold because legally, I can’t have an event.

However, what I’ve done to work with this is one, I was really fortunate that this year, I was bringing in more money than the previous years to kind of sustain myself further at the beginning of year. So I’m really grateful, and obviously not everyone has that.

But what I’ve learned during the event is I’m staying on top of it with the brands that are sponsoring, because are they going to stay on board? You know, that’s the big question for my mind, is how do I keep them for a who-knows long period of time until next year?

What I am doing as this is happening is, I just pick up the phone and call them. I ask them where they’re at, how’s their company doing, what are their thoughts? Can they stay on board? Sometimes people need to spend money by the end of the year. I just ask these questions. Instead of being afraid, I ask them.

Luckily, pretty much every brand has stayed on board. But what has been really cool is the support I’ve noticed from the people I’m working with, because they know that my partner and I make our money off this. Some of our sponsors have offered us a retainer to do some work for them over the course of time.

And other brands—maybe the smaller ones—there’s about one or two who need to spend the money by the end of the year. Instead of just letting them pull their money out, what I am doing is saying, “Okay, well, what can I do for you that we can reuse this money right now? We can do a collaboration.” And all of them are a hundred percent on board for that.

So, instead of thinking my money is leaving me, I’m thinking, “How can I still make this money?” And continue to build this relationship and trust so that next year, my event will be even easier because everybody will sign back on board. We’ll be able to have more people and it’ll be like a ready-made event. It’s all about, for me, not thinking about money leaving, thinking of how I can retransform that money.

As for my blog and my YouTube channel, I’ll always tell people it’s good to diversify because now that that [event] money, which is where I make the bulk of my money every year, is kind of at a low, I have other areas that I can focus on.

My blog and YouTube channel, that’s never affected. While I don’t make as much money off of that yet, now I have a lot of time to really dedicate to it. And because I’ve saved money, I have the freedom to do that. I’m putting more time into that to grow it, because everyone’s dream is to have their own thing, to have their own platform.

So, I work harder on that. And since everyone’s home, the views are going up, the money’s going up on YouTube. I’m trying to make everything work as a well-oiled machine. While it sounds like I do multiple things, they all really work together.

Being a journalist, I meet celebrities who, once I build a relationship, I can have on my show. During my events, I meet brands like Disney. The brands will sponsor me, sponsor my events, or could hire me to do journalistic things with them.

I’m always finding a way to keep this wheel in motion so that it never stops, and always preparing that if something like a pandemic happens, I don’t have to worry about what’s happening because I have this motion going.

Andrew Gordon: It sounds like it’s great to be diversified, have these different revenue streams, but also just to be creative with the ones that you have.

Lindsay Hoffman: That’s what I learned about being a journalist. You have to be able to think on your feet. Say you want to do a story and someone says no. How do you make that become a yes?

Before I got on a call with the brands, I already knew that if someone needed to take their money out, I would offer them a different service for that same price. That way you’re always finding a way to make money.

Andrew Gordon: Great. So, you’ve obviously accomplished a lot over the years, but if you were to talk to your younger self, when you were just starting out, what advice would you give?

Lindsay Hoffman: My advice would just be to not doubt yourself and to believe in yourself, that everything that you feel in your heart is right.

You just have to go for it, because there were a lot of times that I just felt like I wasn’t confident in myself or wondered, “Am I going to achieve the things I want to achieve?”

Sometimes I wouldn’t speak up for what I want. I’m sure everyone’s been there. You’ve thought a thought and you wanted to say it, but you were afraid to say it. And then someone else said it, and then they got the opportunity and they got the credit. You’re like, “I shouldn’t have been afraid to speak up for what I wanted and to go for what I want.”

No one’s going to do anything for you except for you, and if you fail, that’s okay, because is it really failing that you tried? What’s wrong with just trying your hardest? You can always get back up and learn again. It’s just worse to not even try, because people respect that you try. Even if you’re not perfect, they admire that.

So just go for what you want and eventually you will figure it out.

Andrew Gordon: Lindsay, that’s great advice. I guess, in signing off, for those out there that want to continue to have their daily Dose of Bliss and want to follow you, how can they find you?

Lindsay Hoffman: Across all platforms, I’m @lindsaybhoffman and then my blog is www.doseofbliss.com.

Andrew Gordon: All right, well, thank you very much, Lindsay. It was great having you.

Lindsay Hoffman: Yeah, thanks, Andrew!

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