Personal Branding Strategies Every Entrepreneur Needs

0:00Anytime I've made a mistake that I don't want to happen again, I put it in that document. So somebody else doesn't make that mistake. You have to live in that mindset of there's no way you can know everything. It's impossible. And so therefore, you have to go through, unfortunately, all of the highs and all of the lows to become the best. Hey, what's going on? I'm Schweng Esther Shan, and you're tuned in to Shopify Masters, your companion for starting and building a business. Sometimes we become entrepreneurs because there's no other choice. Your ideas and goals don't exist anywhere else and you have to bring your own vision to life.

0:39My guest, Alexa Curtis, never felt like she fit in growing up, so she turned to blogging at the age of 12 and started to build her own personal brand. This passion project eventually led her into podcasting, where she began her lifestyle brand, Be Fearless. Alexa is one of the first creators to sell her show to Radio Disney, and she secured partnerships with brands like T-Mobile and British Airways, all through cold pitching. Alexa is here to share how you can forge your own fearless path. Welcome to the show, Alexa. Thank you so much. What a lovely intro. Thanks for having me. So excited to chat.

1:18So your journey starts so early with blogging and then eventually selling your show to Disney. You truly had to hone in on your personal brand and make it unique. what's your advice for some exercises people can do to set themselves apart great question my advice is that I think people really need to hone into a niche it's so hard now with how saturated content creation has become and I started back in 2011 so looking back then I started my blog because I was a kid from no money no connections and I wanted an outlet so when people come to me now and are like what do I do? I want to be a famous TikToker or YouTuber.

2:00And I remember being young back then, I literally just wanted to make a friend on the internet. And so I say to somebody who wants to start, you need to get back into that mindset of how I was. You can't just go into this wanting to become famous or make a name for yourself. There has to be a why. And I think those are the most lucrative career paths in this particular niche that somebody can embark on is when they've really come to terms with why they are pursuing this personal brand. And then this is a journey you had throughout your teenage years. You actually cold message executives at Disney.

2:35Tell us about that process. And what do you think that really caught their eye? It's so wild, actually, looking back. So I was living in Boston. I moved out at almost 17. I was 16, did the whole starving artist thing there in New York City, and then moved to Boston and was essentially doing and pitching TV segments and doing the same thing with the cold emailing, figured out a way to start getting sponsored by brands who would pay me to go on these TV segments that I would pitch.

3:05And one day, I'm like kind of notorious for going into these deep dives on Google. And I came across this producer list. And I even actually sell it on Shopify shop now, the list of these brands and these producers. And I just thought to myself, you know what? I mean, it was everyone from MTV executives to Hulu to Netflix to Disney. And I, like a real immature person back then, did a BCC to about 466 people from across the board from all of those networks. And it was just a basic intro email. I remember writing it, sending it out. And about a week later up in my inbox comes in the subject line, you know, intro from Radio Disney.

3:50And it was the assistant of the VP. And at the time, his name was Phil. And he said, I would love to take a meeting with you. I've seen your work. Please let me know when you're next in LA. And within literally 72 hours, my gut was like, you're moving to LA.

4:08So I'm not even kidding. I listed the apartment on Facebook Marketplace. I subletted it for three months and I, within that next week, had a meeting and moved to LA to try and get the show. This is really astounding because I think people need to take note that actually you didn't secure a contract yet and you just went with your intuition, but also you were very bold. You took care of like your own finances, your own way there. Like talk to us through that process because a lot of the times people feel like I can't do this until Y is achieved and I'm financially secure where I'm set in certain ways.

4:46But yeah, talk to us about taking that bet on yourself. Well, financial security now for me at 26 is so different than it was for me at age 17, 18, 19. And I think also coming from my background, I didn't grow up with any money. I didn't grow up with any connections. So that mindset, unfortunately, was never instilled in me. So at the time I pitched that show, I mean, I was in a significant amount of debt, probably $25 ,000, which is how I was able to really get through running this blog, doing these TV segments, being paid a lot of the times by these larger corporations on net 60, net 90, which means you're not paid for 60 or 90 days.

5:25And for whatever reason, I was able to get credit cards from Delta Airlines and American having no idea like what I know now about the points and how to properly use credit cards. And I remember, I remember within, I think, three months of getting approval from Disney for that show, I was actually walking down Venice Boulevard, going to Blue Bottle in LA because I love their oat milk lattes. And I remember I called my mom and I said, I have something to tell you, like, I'm in a lot of debt. And I just remember, and it never went through my mind. And this may seem weird if you're listening to this and you're not an entrepreneur.

6:00I never had that fear of something going wrong because I had taken and continued to take so many risks all based on the confidence that I have in myself and my ability to hopefully achieve that success. So to me at that time, the debt and the risks I had taken, it was all leading up to the goal that I would ultimately become successful. So I remember it was a rough conversation with my mom because she said, you know, what's your plan? And I said, I have no idea. And I was able to work myself pretty much out of, I would say 90 % of that debt within the next five or six years after that first phone call we had when I moved to LA.

6:38And so I just, I took the leap. And I also am very aware even more now as my career has progressed, the face-to-face connection that you have with somebody in that meeting. And this was pre-COVID, like there was no Zoom conversation back then. But I knew if I emailed back and was like, I don't live in LA, but like when I'm next there, like you're done, you're forgotten. And that is one thing I think from just a young kid, I was always quite aware is you get one chance to prove yourself. And if you screw it up, you screw it up. And if you don't take the leap, you don't get the chance. I think this is something truly like valuable because when you're young and that hope and that optimism, life is going to chip away at it.

7:18And sometimes you really need to hold on to that because it gives you the confidence to take that risk and be fearless. I would love to talk about that pitching process, even from the message to those meetings. What's your advice now for either founders or creators when they're going through that process? They have to iterate their pitch deck or they have to iterate their conversations with executives to actually make something happen. There's so much to unpack in that. And I forgot to actually answer what you said about why do I think that they replied to me? And I think I had spent years building up my personal brand.

7:55And again, thinking back in like 2017, 2018, personal branding was not a thing. Like TikTok was not even out there. So looking back, that's what I was doing was really building a name for myself in that way. But I was the first person to get in the door with Disney like that. I'm not an actress. I came from a background of essentially this girl from the middle of nowhere who wrote a cold email. But I also think from my work now also having a podcast, I do think that there's certain talent who just have the it factor. And I would say that in that moment, that executive saw something in me. And that's the only reason why.

8:31And I see it now with people that I interview. Sometimes you just have conversations and you're like, that person's got something, right? You're also, you were so dedicated, right? You started in 2011. So by 2017, 18, it's almost like a decade of writing. So I think, like people say, overnight success takes a decade. You show that you were committed to actually sharing your story, like invest in mental health. Like those are all like signs of commitment that the executive saw. And I think right now, if you were to do that, I don't think you would necessarily get in the door. I mean, I talk to young, predominantly women a lot, 12, 13, 14, 15, 16, and they're like, how do I get that?

9:12Had I had no experience, hadn't pitched any of those TV segments, I don't think I would have gotten in the door. I think everyone needs to, you have to put in the work and the grind. And unfortunately, if you don't come from connections, you have to work even harder to prove yourself. And so I had spent 10 years doing that up until that email. but I think now if you're a creator and I wouldn't say if you were just starting to go to a network I mean I won't go on for ages about that but I would say that I think you have to start with producing your own content to try and get in front of say a Shopify right like this media side that you guys have as somebody who has no experience you have to think that you need them more than they need you and I was very well aware of that even on that first meeting when I entered with Disney is like, they did not need me.

9:58Like I knew, like I'm literally nothing. Like I still have that mindset in the way of if I was to get an opportunity like that again, I needed them. And so obviously they saw something that was mutual in that. But at the end of the day, those are the networks. They do this for a job. They pump out talent like that. So if you are a new creator and you want to get in the door, whether it's pitching a show like that or a brand, I think you need to come from a very humble side of what do you think that you can give with your platform to that particular brand or media company. And then throughout the pitching process and negotiation process, it's so hard to speak up to yourself because you're like, wow, these are big brands.

10:40I'm just grateful to be even in this room. But yeah, how do you speak up for what you believe in, negotiate for yourself and advocate yourself in those situations? It's hard. And what Disney put me through the ringer, I'll say, they did not give me that show lightly. I mean, there was months there where there was just a lot of stuff that happened where I thought I was just on the edge of, number one, losing my mind, but also losing the show. So that's a whole other thing. But I think most of that comes from experience, right? Like, the deals that I did when I was 16 and pitching brands are night and day different than now.

11:12I mean, the contracts, the terms. So I think that there's actually a framework called an SOP that a lot of executives use when they hire, especially valuable if you're hiring a VA. Every time you learn something or you screw something up, put it in this framework. And when I have an SOP now for really every element of my business or if I'm ever hiring someone, it is based on everything I've seen somebody who works for me do wrong or that I've done wrong and I want to prevent from happening again. And so when you go into those negotiation deals, I mean, aside from a Disney, because that's a whole other beast with like lawyers and you really can't negotiate on your own for that.

11:49But these one-on-one deals, I mean, at the beginning, you're going to make a lot of mistakes. You're not going to know what your rate is, but I think it's great to always go in with what your gut tells you is fair and then let them negotiate. And a lot of times I find people will say something too high and the brand will say no, and that closes the deal and unfortunately closes that door. But I can almost guarantee you that they were on the brink of saying no anyway. And if someone's not willing to negotiate with you based on the first offer you put in, they probably weren't a good partner from the beginning.

12:20Yeah. And it's important to have good partnerships when you're collaborating. Explain to us what the SOP framework and how it works and how people can approach it when they're going through a process like that. Yeah. So I'll use one, for example. So I have a career development company and I hire every time we host a summit, either freelancers or just like some people who work for me more consistently part time. And it's a framework. So essentially, it's as many pages as you need it to be. And I'll give an example of for my VA, anytime I hire a virtual assistant who sends out, say, my calendar invites or does research, it in there says this is how you approach an email or how you reply to somebody who says this back.

13:02So if it says, you know, I'm interested in scheduling a time, are you available? It says like VA to message Alexa, am I available? But to check this first. And then it says, if somebody says, can I reschedule? The proper thing that I would like somebody who works for me to say back is this. And it's just, it's really streamlined. And it says so that if somebody, it reduces what I like to say, the BS in business. I hate when somebody is like, what do I do about this? What do I do about this? So I'm giving you all the answers to your questions. if you're an employer, a freelancer. And of course, if you have questions, you have to ask.

13:35But for the most part, the answers to everything you want to know for like the basic email etiquette or making a Zoom invite, etc. are all in this framework. And I think if you're a business owner, that it's very valuable. Yeah, it's actually really similar to a lot of frameworks like people in Shopify deploy as well. Like we'll talk about like how we like to communicate on Slack or in meetings. So it just brings a lot of clarity in relationships as well. I think my big question, which a lot of people have is they have these dreams. They would love to do all of this pitching, but there's also like mental hurdles they have within themselves to even get themselves started.

14:16Because again, it feels intimidating. It feels like me, solopreneur, or one person shouldn't be emailing big brands. What do you say for people who are in that position that have those goals, but something is making them feel a little intimidated to start? Well, if it helps, I'll give an example of right even before I came into this, I cold pitched a brand. I honestly have to say I think I sent out the email a month ago and they just got back to me. And the person replied in the email and said she had read an article randomly that I did for Rolling Stone years ago. And she said, I love your work.

14:51We'd love to work with you. Went back and forth on email over the past few days. She was like, well, we're happy to do an affiliate, et cetera, with you. I don't personally do affiliate things. So I said, I'm not interested in that, but would love to proceed with a sponsored post. And her response as of an hour ago was, unfortunately, due to your metrics and the numbers on your social media pages, all we can offer you is affiliate, but would love to, like, continue to watch you grow. And so I think if anyone is watching this, number one, if you want to talk about imposter syndrome, that is, like, the epitome of imposter syndrome, right?

15:21How can I get that and then be sitting here with you who's so accomplished with this incredible platform? And I would say because of my trajectory in my career, number one, I'm not defined by the number on my Instagram. It is out of my control unless I wanted to be a little shallow and buy followers, which personally is not what I want to do. It's out of my control to be judged by that. And number two, it is 100 % up to you to figure out how you define yourself as a business owner, right? if you are looking to be an influencer or you're looking to be a content creator, which means that perhaps you are viewing yourself as pitching a deal to create content for a company where they're paying you to create content for their pages, but it doesn't need to go on your pages.

16:05So you don't necessarily need to be the one that's having to constantly sell your personal pages and be judged by that following. So again, it's all trial and error.

16:20I think that story, you know, I deal with it all the time. And 1 % of people amass that a million followers. So you kind of have to figure out what works for you. And you have to think outside the box and find the brands who really value you as a person and not necessarily what your social media following is. And I feel like you're building more of like a tight-knit community. People who followed you when you were younger all the way till now. And also you've built a community and like a tight knit team of people who you like to work with. Like what's your advice there, right? Whether you're building community online or in person where it's genuine connection and not just numbers on a screen.

17:03Well, two pieces of advice. Number one is that it is essential that anyone who I think wants to embark on entrepreneurship, whether they're creating a D2C company or a B2B creates that community. One of my friends actually started Beehive, which is a newsletter platform. And what they've done, and they're now really in competition with, for example, a MailChimp, is remarkable with the community side that they've built out. And I think it has helped them scale to this company that I think is evaluated now at maybe multi-millions, 40 million plus, close to a billion. And I think what they've done with building community is incredible.

17:37And then second upon that, I would say that those in-person, again, connections are so valuable. when somebody comes to a Be Fearless event. When I host those events, I mean, it still puts me in the red. I very rarely net anything from those. But I always leave with coaching clients or people who want to do more with my work, et cetera, or at least a new follower. And so that's very practical. And then the other second piece of advice is it's very hard to scale community. I think people look at community and they're like, it's such a buzzword. I'm going to scale community. You can't scale community.

18:09There's too many free communities out there. I don't think you can scale it to be the only selling point for you as a content creator. However, you can use it to leverage, right, for how many people or eyes are on your page when you go about pitching companies or trying to get your foot in the door because, you know, you don't just have your social media following. You've also got one-on-one communication with people who are also able to communicate without you as the creator involved. Yeah. And sometimes I feel like, you know, a few attendees into an event, they've dedicated their time in their days to spend with someone versus like just a follow on social media.

18:47So it's really all about like framing how you present yourself. I'm going to take a quick pause to thank our listeners for tuning into the show. Wherever you get your podcast, follow or subscribe to Shopify Masters and write us a review if you haven't already. Thank you so much. So switching gears a little bit, talking about content creation and managing your brand, what are some apps and tools that you really enjoy and suggest to our listeners? Some of my favorite apps that I would say business-wise and then personal. I really like TaskRabbit and WeCossa because I'm mostly in London now. WeCossa is great, but TaskRabbit also is quite practical, I think, especially for finding freelancers or people to help with events.

19:35that's really incredible. Canva, of course. There's one for newsletters that's called MECO that allows you to have all of your newsletters. And I love newsletters in a separate inbox. And then DocuSign also is really helpful. So anytime I'm on the go and I need to brief a contract or send a contract, I can do it from my phone. And I feel very safe being able to do that and not necessarily need to be at my laptop to send a contract. I love it. I also love Substack. Yes. Okay. Yeah, I love Substack too. Yeah. I mean, outside of content creation, your personal brand or business has evolved a lot.

20:12And I think you also believe in this philosophy where your brand has to be in constant evolution. How does someone like think about that as you have to go through a lot of change as your business develops and as your own brand develops as well? Well, you almost answered it right there. You have to go through the changes. I mean, everything that's happened, all of the mistakes. I genuinely believe that people live in a mindset of almost holding themselves so accountable for mistakes they've made and then regretting it. And I prefer to live in a totally opposite mindset is I actually love the mistakes that I've made.

20:48I live with very, very almost no regrets, quite frankly, but I have observations. And it's the same with a business. Anytime, again, even with an SOP as simple as that, anytime I've made a mistake that I don't want to happen again, I put it in that document. So somebody else doesn't make that mistake. So whatever type of business, I mean, entrepreneurship, if you want to be solely a content creator, you have to live in that mindset of there's no way you can know everything. It's impossible. And so therefore, you have to go through, unfortunately, all of the highs and all of the lows to become the best, most successful version of yourself that you can be.

21:24Yeah. Yeah. It almost feels like a multi-stage process too. Sometimes it's like the self-realization of change, communicating it to your friends or family, and then also like sharing it with the wider community. How do you make sure like you're communicating in a way that you want with the community and making sure that they feel included and engaged through your chapters of change? I don't think too much about it, to be honest. I take a lot of pride in very authentically showing up to this platform. I think there's a harsh reality and I've learned very hard this year that when you're going through the motions of being an entrepreneur, and I say entrepreneur and not content creator because I think there's a huge difference between running a business that has the potential to scale very large.

22:12Whereas when you're a content creator, for the most part, that will, it will, it will always go down because there will always be somebody new, right? I have just gone through these motions and made mistakes and learned the hard way, some of them that have really slapped me in the face, that I had no idea the platform that I had built. And I think because when you're a founder, what really sticks out is the rejection. So even the email that I mentioned earlier, it's very hard to not take that so seriously and then never celebrate the wins. And so again, I take a lot of pride in being able to just show up and say really everything that I'm thinking.

22:49Maybe sometimes you say too much and maybe sometimes you could say more. But again, that's the same way as like I hope anyone that follows the content side of what I do is for the most part, I think it's a lot of aspiring entrepreneurs, kids that probably grew up like I did and want to escape a small town and make yourself into something. And if you take anything away, it's just you have to take you have to take a chance on yourself because a lot of times people are not going to take the chance on you or for you. You have to find it in yourself to do it. And that's what, through all of these stages, I've hopefully conveyed.

23:19Yeah. I think a big part with change is also letting go and being excited about the change, welcoming of new things. Sometimes it's hard, though. You're like holding on to old projects, old partnerships. How do you get into that mindset where you're excited about the new and not kind of like lagging on or holding on to the nostalgia? I have to almost take myself out and think of I will say that I mean there's a lot of things I do wrong but that kind of thing I don't really hold on to things like that I don't because I live in that mindset of I don't live with those regrets so I don't hold on to them I just think they shaped me the good things the bad things into who I am today so you really can only move forward however if somebody struggles with that I would say that you know until you really find that thing that makes you so excited to wake up most of the time.

24:11It's really hard to not think about your past. So instead, you need to create almost a new future for yourself. Try something different every day. Go to a different coffee shop. And I think slowly you start to realize there's always layers of confidence. And I think everyone can always work a little bit harder to find that confidence in themselves to no longer think about the past and just solely think about the future. You have to. And I think a lot of that comes from trying different things until you really figure out what is it that makes you wake up every day. And then, you know, you've been a solopreneur all your life and it comes with a lot of solitude.