You're listening to Cubicle to CEO episode 236. We're switching things up today and putting me in the hot seat. Listen to my guest interview on Season One of Honeybook's independent business podcast, the show that uncovers the science of self made success. Previously hosted by my dear friend Natalie Frank, who's guested on Cubicle to CEO in bonus episode 27, where she shares her gutsiest moments, as well as spilled the secrets to a fast growing community in episode 57. Both links below in the show notes. Season Two of the independent business podcast is hosted by another one of my favorite humans Akua Konadu, highly recommend adding the independent business podcast to your show rotation.
In my conversation with Natalie, we get into the science of asking good questions that get responses and get you paid, including the best way to end every email how to approach collaborations combating doubt as a business owner, and the biggest differentiator between the businesses that succeed and the ones that fail. Not only do I draw from my own experiences to share these insights, but Natalie pulls in the proof with science backed stats. This episode is filled with actionable insights for all independent business owners. By the way, if you're looking for an all in one platform to book clients, manage projects and get paid faster, have business flow your way with Honeybook, try Honeybook free for seven days, no credit card required, and save 50% off your first year. When you go to ellenyin.com/honeybook that's ellenyin.com/honeybook will also drop a clickable link below in the show notes. All right, enjoy this replay.
Welcome to Cubicle to CEO, the podcast where we ask successful founders and CEOs the business questions you can't google. I'm your host, Ellen Yin. Every Monday go behind the business and a case study style interview with the leading entrepreneur who shares one specific growth strategy they've tested in their own business, exactly how they implemented it, and what the results and revenue were. You'll also hear financially transparent insights from my own journey bootstrapping our media company from a $300 freelance project into millions in revenue.
I'm gonna kick us off with a fun stat. Okay, we're gonna we're gonna bring some numbers right off the bat here because I know you and I both love, love our numbers. We recently ran a survey. And in that survey, we found that nearly three quarters of independent business owners say that they did not always intend on being a business owner. 72% didn't always intend on being a business owner. And for about two in five that own independent business today. It just started for them as a side hustle 43% Just started as a side hustle. And I'm curious in your journey, first of all, did you always know you were going to be a business owner? And what did that journey look like from your first freelancing project to where you are today?
I love that stat. It's so interesting to me. But it also makes me feel so seen because I myself am also an accidental entrepreneur. So to answer your first question, no, I did not intend on being a business owner. In fact, I was so I guess unacclimated to this idea of being a business owner that in high school, I remember there were two business classes that some people took. And I honestly, Natalie, I'm almost embarrassed to say this. But I honestly didn't even understand what the like what you would learn in a business class. I was like, Is it like a form of math? Like, are you learning accounting? Like, I just did not understand this concept. And so my journey into entrepreneurship, really were a series of steps where I just felt curious about something leaned into it, and then it sparked something else.
So what happened is back in 2017, I was 23 years old at the time, I had been in this corporate job for about 10 months. And I just knew that was not the place I was supposed to be. At that point. I did not think, Oh, I'm going to quit this job and start my own thing. I just thought I'll quit this job and look for another role that's a better fit for me. So I actually did something pretty drastic. I quit this full time job without a backup plan. I had nothing lined up not even an interview at another company. And it was a couple of days before Christmas. So I kind of just took the holidays. And I was like you know what, we'll figure this out in the new year.
And then what ended up happening is, after the holidays, I ended up connecting with an old colleague of mine, someone I had worked with on teams at this corporate job, but we didn't know each other that well. So he actually was like, hey, through your work at this corporate job. I heard through the grapevine that you know a thing or two about Instagram marketing and my wife and I on the side we actually have a family business. We own these two coffee stands. We don't have a lot of presence on social media and we'd love for your help with this. So that was my first freelance project that started at all, Natalie, it was a $300 invoice, I remember that clearly, I had to go to dinner with them to like propose the thing in person. It was a whole ordeal. But it really opened my eyes to this opportunity that I have a skill set that I can monetize outside of a traditional job structure. And that's what started it all. Wow.
So truly from a $300 invoice to a what, seven figure business?
Yeah, I mean, seven figure business, I always hesitate how that term is used, because different people think of it differently. We made more than I think at this point $2.5 million in the business over the course of the last five years. I have not made seven figures in a single year. So it depends on how you define that. But yes, either way, it's just mind blowing to me, because standing there with that client, when we signed, you know, the paper, I would have never pictured being where I am today.
That's amazing. What were some of the challenges that you faced in that experience of going from, you know, first freelance project, all the way to the company that you've built. Now, what what were some of the hurdles and obstacles?
I think this might be not exactly the answer that you would expect. But my naivete was a big superpower. For me, I think I didn't know what I didn't know, because I wasn't one of those people that carefully prepped and planned to exit the corporate life and start a business, I kind of just didn't have a whole lot of fear in a weird way going into this because I didn't have a whole lot of expectations.
And so therefore, all the challenges that came were more things that were just learning curves of Oh, like, okay, taxes became so much more difficult, that's frustrating, or like, Oh, this is how you hire someone, or these are the things that could potentially cause challenges. In the workplace as someone who's new to hiring or new to being a leader new to being a boss, just roles that I had never anticipated for myself and roles that I was woefully, you know, untrained and unprepared for. So like any business owner, I've had many challenges, you know, months where we lost money, and there was no profit in the business. So things like that certainly have come up. And I don't want to paint this picture of, oh, you know, business is perfect, and everything is sunshine and rainbows.
But I think the one thing that I did not struggle with as much as most people that I've talked to maybe have struggled with, especially towards the beginning was the imposter syndrome, I think because of my ignorance. And quite frankly, I just didn't have a chance to be, I guess, insecure about what I was doing, because I really didn't know what I was doing. And I didn't know what was normal or not normal. So therefore, I just kind of like blazed ahead, you know, full sail.
And in Blazing ahead, you've learned a lot You really did, you had the courage to take those leaps. And in doing so you've learned an immense amount. And one of those things I had come across my feed very recently and it and I've been doing this for 15 years. It hit me it just hit me. So we're gonna talk about that in just one second. But I want to tee up a little bit of science into what we're about to talk about. So the reality is questions hijack the brain, the moment you hear a question, the moment you are asked a question, you can't think of anything else, your brain immediately goes to answer that question. If I asked you, you know, what did you have for breakfast? And I give space for that you're immediately trying to remember what did I have for breakfast and you lose sight of all the other parts of the conversation. And that is a very powerful tool.
Back in 1993 social scientists Vicki Moore with Eric Johnson, David Schmidt line conducted a study with more than 40,000 participants that revealed that simply asking someone if people were going to purchase a new car within the next six months, increased the likelihood they would purchase a car by 35%. asking them the question. And by the way, this isn't the only study that has shown that an even earlier study was published in the Journal of Applied Psychology asked citizens whether they were going to vote in an upcoming election. Now asking them that question, just asking them if they're gonna vote, it increased the likelihood that they would vote by 25%. And I say all of that to say questions are incredibly powerful as you're moving into this independent business CEO mindset. And so you were sharing what you call it a conversion killer. I believe in how a lot of us are ending our emails. And so you said stop ending your emails with let me know if you're interested. Why why should we not end our emails with let me know if you're interested and what should we do instead?
Natalie, I am so excited that you are equally as passionate about this as I am and the fact that you took the time to do all of that research. So cool. I didn't know some of those days. points, but it makes complete sense as you're sharing them. So the reason why I recommend people do not end their emails with let me know if you're interested is because a statement does not invite conversation write a statement, essentially, when somebody reads that you're giving them permission, or essentially, you're automatically giving them that leeway to be like, oh, I'll just take a mental raincheck on responding to this. Because there's there's no open loop, right?
We as humans, we are primed to respond to questions, as you said, and we don't want to leave people hanging. It's the reason why when you said, Hey, if you ask someone a question, like, what did you have for breakfast? Based on social norms? It would be really weird for you to sit there and just be completely silent, right? Like, of course, you're going to respond to that question. It's kind of the same thing digitally. If you ask someone a clear, direct question, especially at the end of the email, the likelihood that they will respond as much higher because they don't want to leave you digitally hanging, right? They want to close that loop. And answer that question. A statement does not work the same way. Because a statement is essentially saying, okay, somewhere down the line, if you remember that you're interested. And if you've been remembered to respond, let me know, let me know. And it's, it's just such a closed ended way to, to end an email, but I see it happen all the time.
And it's not just let me know, if you're interested. It's all of its variants, right? Let me know if that works for you. Let me know if you want to meet all of those things are examples of someone reading that and going, Okay, I'll take a mental rain check on your question or your statement rather.
And I'm guilty of doing that myself. When I get an email that ends in that way, I will very likely leave it unread in my inbox, thinking that maybe one day, maybe one day in the future, when life isn't so chaotic, I will get back to that email and spoiler alert friends, is life ever not that chaotic? No, I never go back. And then so much time passes, that I feel so much guilt about never responding that unfortunately, I become the ghost that we all dread, where I just archive it and move on with my life. So you are nailing a very key aspect of human behavior. Now, for the person who normally ends the email that way, okay, who says okay, just let let me know, if you're interested in I'm using my passive voice here, intentionally, because that's how I read it. When I when I read that in someone's email to me, what should we do instead? What how should we close out that email? Do you have any recommendations for us?
I do, I want you to think of yourself as a guide. Okay. Think of yourself as how can I make this the easiest possible for someone to respond for them to burn the least amount of brain calories to know what they should say? Because that's another thing too, is when you place the responsibility on someone else to respond, sometimes because their lives are chaotic, or because they have a lot going on. It can almost feel overwhelming, like, oh, I better wait to respond for when I have time to really sit down and think about what I'm going to say right? We've all felt that way before. But when someone asks us a very clear, specific question, it reduces that friction of responding because we don't have to sit there and think about all the possible things we could say we only have to answer that one direct question.
So a good question you could ask is, would you like to move forward with this? Is this a good fit for you? Which of these options do you prefer? What time would you like to meet all of these? Do you see all these are very specific. And again, like you mentioned earlier, Natalie, in that study about car buying, when someone was asked, Are you going to buy a car and the likelihood that they did was much higher? I think it's because you are placing a direct intention in someone's mind right at the forefront of their brain. So again, if you're asking someone, would you like to move forward with this? That intention is now sitting in the front of their brain? They're thinking, well, I need to decide, do I want to move forward with this? Yes or no. And I think helping someone make a decision. Facilitating a decision is one of the most powerful moves you can make an business, especially when it comes to conversion and sales.
I love that. So, so much. This is a great reminder for anyone listening, this is the time go back, revisit your client flow, look through those email templates. Are there little tweaks you could make based on all of that advice that Ellen just shared? Right now today? It can take two minutes. That's it, jump into a template and conclude it with a question and with a strong question. I love how tactical and actionable that advice is. One thing that I really love about you, Ellen is just how innovative you are in marketing yourself, your business, you aren't afraid to try new things, you take risks, you are constantly paying attention to, you know what's happening on different platforms. And so I'm really curious, is that something that comes naturally to you? Is that something you've had to learn as a business owner and any tips you have for us in just being so innovative ourselves when it comes to marketing our independent businesses?
Well, thank you for that huge compliment Nat I think, honestly, I think it's something that has always come naturally to me, mostly because I'm a very curious person. I think curiosity is one of the most underrated strengths that you can have as an entrepreneur. So it's not that I know everything, or I'm this genius, or you know that just everything comes easy to me, it really is because I'm willing to get curious and ask a lot of questions. And therefore in conversation with people, ideas, spark, and so I think that's the key to creativity is actually collaboration.
And so even, for example, when we're talking about, let's say, partnerships, partnerships, especially between brands is a huge part of our business model as a media company. So we have to talk to brands all day long and really understand what are their goals for this year? What initiatives are they working on? What incentives can we align on? And that requires a lot of curiosity requires a lot of question asking and thinking about, okay, so this is your goal over here? And this is our goal over here? How do we meet in the middle? How do we find fun ways, creative ways, unique ways to pour both of our resources and our communities together in order to achieve one shared common mission.
So, you know, we've had the pleasure of working with Honeybook before as a partner, and it's so much fun, I think, if you treat business like a game, and you don't think inside this rulebook of, okay, it's always been done XYZ way, therefore, I need to follow this formula. But instead you look at it like, Okay, if I put, you know, roll this dice and move my character over here and color this a different thing, what could happen, and just staying very open to those possibilities is such a game changer.
When I hear you say that I hear and I'm reminded of the fact that when we experience immense amount of pressure, in business, when we feel the weight of that pressure on us, it increases a lot of the stress hormones in our bodies, cortisol, for instance. And that actually makes our brains more more rigid, it actually inhibits us from kind of having that plasticity that allows us to think beyond the bounds of what we know, I think of it a lot like a GPS, like it's kind of saying, you know, when we feel that pressure, we feel like we have to zero in and go from point A to point B and there are no room, there's no room for detours, no room for exploration, innovation, adapting none of that. But what I'm hearing you say is instead of feeling that pressure, you've had this mindset of curiosity, and play, and that curiosity and play what it actually does to the brain as it increases levels of cannabinoids and opioids that are endogenous to our bodies, right like that aren't from the outside, we're not talking about drugs here, friends, we're talking about actual hormones you already have inside of you, it increases levels of those sorts of things.
And what it does is it actually makes your brain more plastic, it enables you to see possibilities that you wouldn't have seen before to put yourself in positions that maybe you wouldn't have put yourself in before will link to some really cool science on play in the show notes if that's something you're interested in. And I know, the Hebrew in podcasts has an amazing episode on this highly recommend listening to as well, the point being, I'm hearing that that level of play and curiosity kind of abound in your overall approach to business and life. And you can see how that has played out in your ability to grow, you know, in a multitude of ways.
Now leaning into that growth that you've experienced, you've gone from just being, you know, one, a team of one your own boss, and that, as we all know, is hard enough, that is a challenge as a solopreneur. If that's the position you're in, that is hard. But you've expanded your team you've grown and brought on employees. I want to talk a little bit about that one. When did you know it was time to hire and to what have you learned as a leader in that experience of going from just leading yourself which again, we know is hard to leading a team.
Oh my goodness, we could talk for hours about this. And I'm still I'm still very much in the trenches learning as a leader on this particular topic. I think it's actually my weakest area as a business owner. In terms of my own skill set and aptitude for you know, it does that part like friendship connection comes really easy to meet management does not come easy to me it is like not something that I enjoy or that I thrive in. So I would say my first year of business 2018 Completely solo, I did all the projects, all the things wear all the hats. In 2019 My second year of business, I hired a part time contractor to start helping me with some of our client accounts.
At the time, our business model was still a boutique marketing agency. So we were doing done for you social media management for a multitude of clients. And so I brought her on to help with you know, small things at first, I think actually, her first project was literally putting together like kind of like a capstone report for this influencer marketing campaign. We had run for a client, and then it kind of delved into Okay, could you help with hashtags here? Could you populate some captions here and it just kind of snowballed, you know? And actually, by that summer of 2019, she had really taken on a lot in that business and then soon after, became my first full time employee. And then it's fun Looking back, because you know my business, although we're more than five years now, in the grand scheme of business, we're still very much a baby, right?
When you look at Legacy businesses that have been around for generations, but it's really one thing that I hold very dear is that very first employee eventually went on to create and start her own business. But she still is part of our team to this day, in a different role, her role has changed many times, she's now a Community Manager in one of our programs. But the fact that we've kept that relationship so strong Over the years and have been able to adapt to each other's changing lives, and changing businesses, I think speaks volume to the privilege that we have as independent business owners to not do business, the expected or corporate way to not have to, you know, completely cut ties with someone because their ambitions may change or whatever it may be. So we have that adaptability as independent business owners that I think we really, really need to lean into.
So anyways, from that point, fast forward to this day, I have two full time employees, and a few amazing contractors that I work with on a regular basis to help produce all of the content that we put out on Cubicle to CEO to help with client work. And I think the biggest lesson that I've learned in leadership and hiring is, when you are starting out as an independent business owner as a solopreneur. Everything in your mind, speaking of questions, everything that you come across your natural question is, how do I do this? Or what do I need to do? Right? You're asking a lot of how and what questions, the more you evolve as a leader, the more you have to train your brain to not ask so much how and what but instead, who, who would be the best fit for this, who could lead this project who could whatever it may be, right. And that's a totally different approach. It's a totally different mindset. And it is a transition, especially when you're used to doing everything yourself.
And so I really had to learn that. And I've really had to learn how to allow people to make mistakes, and to figure it out on their own in the same way that we had to figure it out on our own, because you can be there as a guide and a mentor and a support. But it does not mean that you have to treat you know your employees really any different than how you treat a business, you can allow them that same room for safe play and for failure and for all those things, because that's how they're going to learn as well.
Google did a study on what makes the most effective teams. And what's interesting about Google is you have Rhodes Scholars, you have MIT graduates, you have the brightest oftentimes in the world coming into those rooms to work. And yet, they found that it wasn't intelligence that created incredible teams, they found that it was psychological safety, the ability for people on a team to do exactly what you just described, which is feel safe, to make mistakes, feel safe to voice their thoughts and opinions, bring their lived experience to the table, right show up as their true selves and know that they're going to be met, not with well, if you screw up, you're out of here, you make one mistake, you're gone, right? That's that pressure we're talking about. They're actually encouraged to be curious to explore and to learn on their own so that they can grow into those roles and have success.
So I, I hear a lot of wisdom in your leadership, even though you're saying, you know, I'm learning everyday, and we all are. But again, it's that endless curiosity that is so so, so powerful. Now, I want to talk for a second about doubt. Because we've talked a little about some aspects of the CEO mindset, whether it's leadership, it's question asking even how we shift our questions, like you said, from the what the how to the who, gosh, what a CEO hat that is, I want to talk about the doubt aspect of the CEO mindset.
Because the reality is, from the outside looking in, it can be easy to assume that someone like you who's had this success, who's growing this team who's built this profitable business, you know, doesn't feel doubt, doesn't feel fear or insecurity in any way. However, I'm willing to bet that that's not always the case. And so I'm curious how you confront doubt. How do you navigate it when you know you're launching something big or you have a massive goal, and there's that insecurity that starts to creep up and creep in? What do you do in those scenarios? How do you push past it?
One thing that has helped me a lot in combating doubt, is reminding myself of the impermanence of many of our decisions. I think, as CEOs as business owners, we often attach too much to our expected outcomes of something because we feel that we have already risked so much to even be here building our businesses. So every further risk we take feels like this has to work out or else right. But I think one of the things that has actually aided me most in our trajectory, and our growth has been this willingness to realize that many of the decisions we make in business and in life, quite frankly, are not permanent in the sense that they can be reversed, right? They're not so final as we would make them out to be.
And so I find a lot of comfort in that when I doubt in times of doubt, and and when I'm unsure, is this the right move? Are we doing this the right way? I think, okay, I can sit here and think all day in my head. But the truth is, and you and I both really align here, the data is going to tell the true story, right? You have to put it out there to gather the information to get the data to make more informed decision, if you're just the blind leading the blind in your own head or, or you know, hypothesizing with your team or riffing with friends, although that is valuable, if that's the place that you remain stuck in. The truth is, no one really knows until until you put it out there. And that data is so valuable.
And so these days, I don't feel as fearful of just like doing things, even if I'm not sure what the outcome will be. Because I find so much value in the information that is collected from that experience that regardless of whether it turned out the way I thought it would or doesn't, I still feel like it was a win. I'm like, awesome, I have data now, that will help me make a smarter decision next time. And that to me is worth the try.
I love it, you do a lot with transparency as well. So you talk about, you know, the data you're getting internally and how you're kind of navigating that. But I do want to shine a light on the fact that you are incredibly transparent. When it comes to numbers, and you even share on your podcast, you know, income reports, for example, you are not one to shy away from getting real about the numbers. And I'm curious as to your why there because I have a suspicion there might be something deeper going on here to see someone at your level to just be so transparent with numbers talking about it, bringing that into how you educate. Why do you feel like that's important?
Oh, my goodness, this is like this is what our entire media platform is built around Cubicle to CEO was created to bring a transparent lens to business stories, right, we want to tell the stories a of underrepresented entrepreneurs. But two, we want to do it through a financially transparent lens. Because I think when we're afraid of talking about money, when we keep people in the dark, it only hurts us in the end, right all of us. And I think as we collectively share data, share information, share transparency, we collectively raise our financial IQ, which again empowers us to make smarter decisions to ask for, you know, the right rates for the work that we're doing to advocate for other people. There's so many I think benefits of coming to the table and normalizing talking about money in in industries, with your peers, with your bosses, with your friends with your family loved ones, you name it.
And so really though it started out I mean, that's the mission now, but it started out like many things in a much simpler way. For me, what encouraged me to first start sharing my income reports was actually other women, other women who had trailblaze away, when I first started as a solopreneur, I was just a freelance social media manager with again, no context for what business really was what I should be charging, I feel like everything I was doing was kind of just flying by the seat of my pants. But then I started to find some income reports, mostly on blogs that it wasn't super common still isn't super common today, but becoming more and more common, which is great.
But at the time, I found, you know, a couple income report blogs, and I just started reading them and realizing things that I don't think I would have become aware of as quick or maybe ever had I not been exposed to that information, things like, Oh, I didn't realize like, this is how you allocate the money that you earn, like how you actually spend it, like what are the expenses that I should be investing in to help me grow my business, or, Oh, that's really smart that you aim for this percentage of profit, so that you can save X amount for taxes and then X amount for reinvestment and growth and X amount to pay yourself. Oh, that's how you manage that cash flow. Or oh, like, I didn't know that you could charge this much for this type of service, or this type of work with a client.
So it was all of these new input things that would have taken me years of experience to come across myself, but because someone else was willing to open the doors, and, you know, give me a peek inside their business at their books, I was able to learn these things at an expedited rate. And so in having experienced that myself, Natalie, I was just overcome with this desire or this urge to pay it forward. I was like if someone else did that for me, how cool would it be if I could share what I'm learning in my business, what my business is actually making but not just making what what we're spending on and what we're profiting and what we're learning on the way and the strategies that we're trying that work and don't work. If I could bring people with me into that conversation, maybe I could do for someone else what they did for me.
And so that's how it started. It was just these emails, these written reports that I did in 2019, until I switch to doing quarterly income reports on our podcasts on Cubicle to CEO and now every 90 days, for four years, I've shown up and shared exactly what our business makes, spend some profits, and all of the lessons along the way. And it has been, honestly one of the most favorite things I've ever done in my business.
That's incredible to hear. As we close this out, I first want to say, there have been just nuggets on nuggets of wisdom with each question I have just been blown away, and I know you very well. And here I am, like wishing I could be taking notes, I have to be re listening to this one and take some notes myself. There's a question that I love to ask at the end of every episode, because this is a podcast about the science of self made success. And so, Ellen, I'm really curious, what do you think is the biggest differentiator between the businesses that succeed and the ones that fail?
Oh, easy. It is an affinity for failure, a love for it actually the desire to fail as often as possible, because like we talked about today, Nat, data, drives everything right? And you cannot, you truly cannot become the person you want to be or grow the business you want to have. If you are basing everything, filtering everything through the lens of your own lived experience, because what you know, limits what you can dream, right.
And so until you put yourself out there and experience a lot of things meet a lot of people fail a whole ton. It's not possible for you to think bigger. And so when I look at all the most successful entrepreneurs I admire, they are hand in hand with failure. They are linked together and they're excited about it. And so I think if you can fail forward and fail fast, you are going to do so much for your business compared to just trying to, you know, navigate everything with as much perfection as possible.
What an answer. Ellen, thank you so much for joining me today. This has just been incredible.
Thank you so much that you're the best.
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