What if your business could thrive even when your world is falling apart? Imagine breaking free from hustle culture and building a business that’s in alignment with your life. That’s exactly what Sam Vander Wielen did. After a difficult season revealed how unsustainable her pace was, she reworked her business so that it could run even when she didn’t have her foot on the gas.
Listen in as she shares how her evergreen content system generates leads and sales for her, her top tips for a successful webinar, and what grief taught her about success.
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Building a business that runs without you
In 2018, Sam’s dad was diagnosed with Leukemia, and she became his caregiver. She started her business the year before, and it was already thriving. However, with less time to devote to it during her dad’s illness, her business started to falter.
Sam realized at that moment that her business only did well when she had her foot on the gas, and she wanted to change that. She wanted to build a business that supported her life and kept moving forward without her daily presence.
The first thing she changed was her approach to content creation. Sam was creating what she now calls “toilet content,” AKA content that didn’t have longevity or a call-to-action. She shifted her focus to her email list instead and created content that purposefully drove people to her list.
Instead of creating content with a short lifespan, Sam started focusing on evergreen content that could continue generating leads weeks and months after she posted it. No matter what type of content it was or what platform she posted it on, it always included a call-to-action that guided people to her email list.
Utilizing her email list, especially when she ran sales, played a huge role in increasing Sam’s business’s revenue. She was able to stop screaming into the social media void and reach her ideal clients.
Step-by-step guide to creating an evergreen content system
To create your own evergreen content system, you need to become extremely aware of your customer and their needs. What are they struggling with that you have a solution for? Dig deep into customer research to figure this out, because the next step is to design a product that resolves their issue.
Lastly, you’re going to create a freebie that leads them to your product. For example, let’s say your freebie is a webinar. If your evergreen content speaks to their needs, it will naturally bring them into your webinar. Your webinar will also speak to their needs and offer a solution, which will naturally take them to your product.
Sales come more easily with an evergreen system because it creates an organic progression through your offerings.
How to create a webinar that converts customers
The first step to creating a revenue-producing webinar is to lead with value. Too many webinars are all fluff until the sales pitch at the end. Flip this on its head by packing the webinar with value so that your audience feels like they spent their time well.
You can also build trust with them by letting them know up front that there will be a sales pitch at the end.
Another tip is to stay engaged with the comments and make sure you are addressing your attendees’ needs. You want to make people feel seen and appreciated for taking time out of their busy schedules to show up live.
Engagement should start before the webinar begins. For example, when someone signs up for one of Sam’s webinars, they get added to an email sequence that leads up to it. In one of the emails, they’re asked to share what they’re hoping to get out of the training and any questions they have. Sam will then send a message back, often via a voice note, addressing their question and assuring them that it will be covered during the training.
The more you engage with your audience and address their real needs, the more like they are to engage with your content, show up to webinars, and make a purchase.
How an evergreen content system can help you focus on what matters
Ever since she made the switch the an evergreen content system, Sam’s business has allowed her to refocus on what really matters. She lost both of her parents in the same year and didn’t have the capacity to focus on business growth. However, her business maintained steadily during that time and still provided for her life.
Since 2019, Sam’s business has brought in seven figures every year, and she’s also able to take beach vacations and prioritize other aspects of her life. Instead of the constant hustle, she gets to define what success means to her.
As a business owner, it’s crucial to understand your capacity. It’s common to say yes to every opportunity that could grow your business, but it’s also a recipe for a quick burnout. It’s okay to slow down and focus on what you actually care about. If you need to take a break, trust that your audience will be there when you return.
A helpful analogy is to treat your business like an athlete’s mentality. They go hard during the season and then rest during the off-season. In between sets, tennis players even put a towel over their heads to block out all the sights and sounds around them.
Remember that you get to define what success looks like for you and your business. Detach your worth from your business’s vanity metrics and focus on building a life you love.
What does having an unbreakable business mean to you?
For Sam, having an unbreakable business means having a business that supports her lifestyle and isn’t dictated by anybody else’s definition of success.
Important sections of the conversation
- [1:46] The Origins of When I Start My Business, I’ll Be Happy
- [3:14] Sam’s story: Building a business that runs without you
- [10:23] The value of evergreen content
- [12:48] Step-by-step guide to creating an evergreen content system
- [18:27] How to create a webinar that converts customers
- [21:22] How an evergreen content system can help you focus on what matters
- [24:21] Navigating grief while you run a business
- [27:40] Treating your business with an athlete’s mentality
- [30:55] Sam’s next steps and what she’s learned about herself
- [36:00] Rapid fire questions
- [40:54] What does having an unbreakable business mean to you?
Connect with the guest
- Sam’s Sidebar newsletter: samvanderwielen.com/sidebar
- When I Start My Business, I’ll Be Happy book: samvanderwielen.com/book
- On Your Terms podcast: samvanderwielen.com/podcast
Episode transcript
Akua: Today on the Unbreakable Business Podcast, we have the incredible Sam Vander Whelan, who is a lawyer turned entrepreneur, podcast host, and author of When I Start My Business, I’ll Be Happy. Sam opens up about how her personal challenges from grief and trauma reshaped not only her life, but also the way that she built her business.
She shares how those experiences pushed her to create a business that’s sustainable, flexible, and able to run even during life’s hardest moments. And not only that, we also talk about how she stays aligned with her capacity as a business owner. This conversation was so powerful because Sam’s story is a true testament of what it really takes to be a successful business owner.
Now let’s get into the episode. Welcome to Unbreakable Business, the podcast where we uncover the untold stories behind entrepreneurship. This isn’t about polished success stories. It’s about the sleepless nights unexpected roblox and unshakeable grit that builds businesses that last. Every week we sit down with entrepreneurs who faced it all, sharing raw, honest conversations about challenges, growth, and the moments that made them unbreakable.
Whether you’re just starting out or chasing your next breakthrough. This podcast is your reminder that you have the strength to keep going. Hello, Sam. How are we doing?
Sam: I’m doing so well. I’m so glad to be here. How are you? Happy to have you. First off, congratulations on your new book. How does it feel?
Thank you. It feels great. I, it’s been like, it’s been a longstanding dream for me to have a book, to be able to just, even the process of like writing the book. I really loved the whole process, so like. It actually coming out was just one part I was excited about, but I was also really excited about writing it and like developing it too.
Yeah.
Akua: Okay. Well let’s, let’s talk a little bit more about that. Like what initially inspired you to write this book and how was that whole experience like?
Sam: I wanted to write a book that was. Yes. Kind of about business in terms of like, here’s how you can start a business, or here’s how you can grow a business online, especially from the like marketing angle that more spoke to me, which was like not super hustle culture, like anti girl boss, like all this kind of stuff and, and really just like maximizing the use of my time when I was working because for me, I wanna have a business that lets me go live my life.
But then all this stuff happened to me in my life, and that’s then when I was like, well, I wanna write a book that’s for, yes, for business owners, but also for people who have all this other stuff going on in their life, whether they’ve experienced grief like I have, or they’ve just gone through a hard time, or they just had a baby and like, they’re like, how am I going to survive this?
How am I going to grow a business and do this other stuff? So yeah, that’s what I really hoped that the book would do.
Akua: Yeah. I love that so much because, you know, I, um, I gave a keynote last week and I shared that, you know, I think a lot of the times as business owners, we’ve been taught to compartmentalize that business is here and like our personal life is over here.
Yeah. But to me, business is personal. Like there’s so many aspects of our life that can drastically affect our business, like. Pours into our business like, you know what I mean? And I think like your book is just a perfect testament to that. And you’ve mentioned like some of the things that you’ve gone through, but you do have like, what was that one moment for you that really trigger this major pivot?
You have a very interesting story. So do you mind sharing any of that?
Sam: Yeah, it was really when my dad got sick. My dad was diagnosed with terminal leukemia in 2018, and I had started my business about a year before, and my business was doing pretty well, and I could have kept kind of going like that. The problem became when my dad got sick and I became his caregiver, and I’m attending.
Chemo sessions and driving him into Philly and like doing all these things to take care of him. I couldn’t show up for my business the way that I used to. And what I saw happen was almost immediately my business started to not do as well as it was before. And that’s really when I made that connection of like, oh, my business does well as long as I have my foot on the gas.
How do I start to build a business that’s doing well, even when I don’t have my foot on the gas? Or at least like don’t have it on the gas on in like a daily way, especially with things like social media. So at that time it was so common and so popular to be like on Instagram stories every single day doing like.
Instagram story trainings every single day. You know, that were original content that disappeared in 24 hours, but I, you know, I realized like there had just had to be another way. And so that’s when I really started to dig into creating evergreen content and also creating an evergreen funnel in my business that drove consistent revenue to my business all the time.
Akua: Yes. I think that’s such a, a powerful testament of like. You know, when life just unexpectedly happens and how you’ve had to really just adjust and pivot. And it’s true. Like we always, uh, we’re at the center of our business and I think a lot of the times we really need to realize again, that things can happen.
So the questions that we need to be asking ourselves of like, as we’re building our, our business to be sustainable, how, what are places that we can remove ourselves to where like when things happen, it’s still running, it’s still making an income to where like, you know, that’s. It’s a such a hard piece of like when life hits you, the last thing you wanna be worried about is making a living.
Yeah. And so, and that’s something where I feel like a lot of the times it’s not. A popular thing to think about, but I think it’s such an important thing to think about as business owners of like, as you’re building whatever season that you’re in, asking yourself, okay, can this run without me? And if not, like, I need to be looking at the systems.
I need to be producing evergreen content. I need to be, you know, where again, it’s, it’s on autopilot. And I think that’s such a, a good testament to that of like if you’re a business owner and you’re like, okay, like I have been creating content, I’m finding myself on this hamster wheel, really leaning into.
Evergreen practices, I think overall in just like your business, I think is so key. And one thing that was really interesting with you that we learned is that you’ve also had like a plane cry, like a near like. What can you please? Well, also, well, it felt like it.
Sam: Yeah. Thank God it did not actually crash, but I was on a plane that felt Yes.
Well that what the experience, like one of those, uh, like really violent, violent, turbulent issues that you like, tend to hear about on the news. Yeah. And so it was really bad and you know, obviously everybody on the plane thought it was going to and. We, I don’t know. I, I literally this, so this was before I started my business.
Mm-hmm. And it, at that time when I was on that plane, I was really just operating from like a very victimy place, thinking like everything had happened to me up until that point, and it really took that plane ride home from Amsterdam back to Philadelphia. That really shook me, literally awake. To be like, you have way more control over at least your path, like what you wanna do.
I can’t control how it goes and I can’t, you know, control the outcome and the success and all of that. But I was acting like my path was happening to me, and that’s really what shook me to like, thank goodness taking action.
Akua: Yeah. But I think that’s so powerful. I love that you, you shared that piece as well, because like life is just consistently hitting you and like you said, like.
You know, having that victim mentality doesn’t serve you. And one thing that for me, that I have been leaning more into is when things don’t go my way or things are, I feel like are crumbling, I always say like, this is happening for me, not to me. It’s making space for the things that I truly want. It’s making space for the things that I really need.
You know what I mean? And I think that’s such a, a good testament to that. And I know that sometimes it’s easier said than done, especially when you have bigger. Circumstances that happen, um, like a near death experience, like, like turbulence. I mean, that’s intense either, like, you know what I mean? Like that’s a lot.
Yeah. And you know, but I think again, it’s like just the fact of it’s taking more of control of your life. And I think we have more control than we give ourselves. And so for you as you’ve, you know, have dealt with like your dad being terminally ill, and then having this, like how did you approach building and running your business?
Sam: Yeah. You know, I was talking to a friend yesterday who she recently had a baby and we were saying how similar it was in that you have like these two very distinct like moments and paths of realizing all of the things that you used to do that were a waste of time. And then showing up and maximizing the time that you do have.
And so both in her case, which was the happy case of having a baby, and then like my case of having all of this stuff was, you know, I like you’re saying like kind of this beautiful opportunity. So I think that I spent that time being like, okay, what can go right? And a lot of that was the, what I call now toilet content.
Like. Creating a lot of content. I was creating way too much content and then creating a lot of content that didn’t have a lot, lot of longevity, or creating content that didn’t have a call to action. That moved people to a place where I can nurture them in a more automated way. So like for example, creating one piece of social media content that had a call to action.
To like watch my free legal workshop, which then sent people down an automated path of emails and watching a training and then buying my product, which is what ultimately brought in those consistent sales versus before, just like creating content for entertainment and for fun and whatever. It was both a waste of time and not bringing people in.
So that’s really like the mindset. It shifted it. It also, I would say shift in my mindset on my email list, just being like the number one thing that I wanted to focus on. And so even it like that way you could plug in any platform, like if Instagram was most popular or TikTok was most popular, it didn’t matter what the thing was.
I wanted to get those people onto my list, and then I was able to build up my list so much. That when I went to go run a sale or something like that, I was able to generate so much more revenue than just screaming into the void on social media all the time.
Akua: Yeah, I love that. Like I really want us to break that down of, you know, you focused a lot more on revenue, revenue generating tasks, and I think a lot of us as business owners, we need to really keep realizing and doing those check-ins with ourselves of like, is this specific task going to make me money?
And if it’s a yes. Great. And if not, like, no. And so, and I, I love that you shared that, like really maximizing your time, making sure that every single time that you’re spending on your business truly does count and truly does make an impact. And so let’s kind of talk a little bit more about that content.
When you are creating this evergreen content, how are you like, I think a lot of people with Evergreen, right? Like I think we, there might be some misconceptions and so when business owners are thinking about evergreen content, what are some misconceptions that we’re still holding onto?
Sam: Yeah, evergreen content.
I guess the way that I mean it or the way that I create it is that first you have to zoom out and think about whatever your top of funnel things are in your business. Yeah. So if you have, if you’re using a webinar, if you have some sort of other freebie, I also go straight to my email list, uh, with a lot of my calls to action.
So kind of picking what you’re like, imagine as if you were running a restaurant. And you were creating like a really tight menu with only a handful of like, just really good entrees. That’s the way that I like to think of it, about it. And then for me, when I save a green content, I mean content that has a call to action to one of those things, so that regardless of whether somebody watches my reel today or six months from now.
They’re opting into something that’s still relevant and that will still send them somewhere. I need them to go in my business to take the next step. And so, yeah, sometimes I have to create content that’s about something that’s timely or trendy or a hot take or, um, even something like, I just recorded a bunch of content today for free live legal workshop I have coming up on October 20th.
And so, you know, obviously that’s not gonna be as useful once it’s over. But in general, my rule is like. That it, whatever I’m creating, has a call to action that it’s consistently sending people in that direction. I think one of the other big myths about it is that it’s like boring or stale or like you talk about the same things and I always am like, yep, news slash you do and that means that you’re doing a really good job and that you’ll be consistent and you’ll be known for whatever it is that you teach.
And yeah, I just, I really believe that this stuff is like little deposits that stack up over time and gain interest.
Akua: Yes. I love that. And I, I’m, I’m glad that you like shared that because I think, you know, a lot of the times with content, because especially social media, Instagram, I mean the shelf life on posts are not that long.
And so really thinking strategically, okay, like what is evergreen content that is always going to drive results for me. And it may not be trendy and it may not be currently timely, but again, like it’s that messaging piece, right? Consistently being consistent with your messaging so that you’re able to make the sale so you’re able, so people are able to take that step that you’re needing to so that you can make the sale more.
So, yeah. And so for steps of business owners really building out this kind of evergreen machine that can really run on its own. What are some three like key things that business owners need to be thinking about?
Sam: So you need to make sure that you’re really, really aware of what your customer. Really is looking for like what they’re struggling with and what they’re looking for.
Like what, not necessarily if they’re looking for a product, kind of depends on like where they’re at in the awareness scale, but in terms of what solution they’re looking for of like what, what do they want to resolve in their life? What do they think it will bring them, what do they think? It will stop for them and once you’re clear about that or take that first step of like spending a lot of time really getting to know it, I would say.
Then the second step is to design the product that resolves. This for them. And then the third step is now to create some freebie that leads to the product. So this is essentially how I did it. So to use my, like my business as an example. One of the things that I did was really spend a lot of time getting to know so many customers, knowing, talking to thousands of people about what legal questions they had about starting an online business, what hiccups they were running into, what were they afraid was gonna happen, all of that kinda stuff.
Once I understood what they really needed, which was. Basically a set of contracts, plus they needed trainings on how to legally start an online business. I created my main product, the Ultimate Bundle, and then I created a free webinar that was essentially like a skeleton version of the bundle. So it was like the five major points that I teach about in the bundle so that when I would create that evergreen content to attract people to the free training.
Those people automatically needed the bundle. That was like the next natural step. So I was able to use the exact language in my evergreen content to call them in to watch my free workshop in the free workshop. I then used that same language to be like, that’s why I created the bundle. And so the sales came very, very naturally.
Akua: Yeah. And I also wanna highlight of like what you shared, like you talked to thousands of people.
Sam: Mm-hmm.
Akua: Like I think we need to really, we had an episode that we just released a couple weeks ago with a messaging strategist and we were talking about that, about how you need to ask your audience. And I feel like a lot of the times and like.
We have to realize that we have to work in order to earn people’s trust. And I love that you’re like, I talked to thousands where you got super clear on the messaging to where again, it was the natural step for them to take. Like, I mean there’s been so many changes with business owners and I know like leads are something that business owners are trying to, to gain more of.
And for you, you are still currently seeing success with webinars. Correct? Because I have seen like a little bit of conversations with like. Uh, webinars aren’t the best, like, you know what I mean? And so for you, you are still seeing success with webinars today in 2025.
Sam: Yeah, we’re seeing major success with webinars.
We had almost 5,000 people sign up for my live webinar in, uh, February alone. Mm-hmm. But we have thousands of people sign up every month on through my Evergreen funnel as well. So we are still seeing a lot of success with it. I mean, I definitely see a dip over, like, one thing I think that people in the online business industry need to stop doing is like comparing everything we did in 2020 if people, if people weren’t in business back then, because it really, it was just like the heyday and, you know.
So it’s like if we just keep comparing everything to that and being like, it’s down, it’s like, it’s not necessarily down compared to normal years, maybe over that. But I, I do agree like that things have changed. I mean, first of all, like my ads have changed a lot, which, uh, like pitch the, the free webinar, but.
Even within the webinar itself, like I would be open to, or I would encourage other people to be open to playing like, well, first of all, never use the word webinar. I never use the word webinar. You’ll never see me say that anyway. And so like that’s one way to get people to make sure if, if you create something that’s free, that’s really helpful to people and it speaks to the pain that they’re in and promises the solution that you know that they’re looking for.
You can get people to sign up for it. It like this idea that there’s like a grand conspiracy that people are watching our stuff and being like, wait, it’s a webinar. I’m out. Like pe, people want the resolution so. To me, this is more of a marketing problem of like how we’re talking about it, but we can also like change up how you offer it.
Like they can become shorter. I know like some of my friends have experimented with shorter ones. There’s different like things that you can do throughout the webinar to like keep their attention and like, because we struggle with retention of attention. So you know, things like that. Like it doesn’t mean that webinars the way that we did it in 2019 or 2020 have to stay the same.
But I, I think in general, like the concept still works even if you try to do it differently. Like for example, one thing I’ve done that’s worked really well, which is new, is that with my webinar, they also get a podcast only version of it. I never did that before. I was so intent on like, they have to see it.
They have to see it, people love it, and we always get hundreds of downloads in addition to the people who come live. So I think like, that’s really interesting, like just offering it up in a different way. We put it on YouTube, we go live on YouTube, like we just do. I don’t know. I’m always like, open to trying and doing things differently.
Yeah, I, I love
Akua: that. I think that to your point, that was such a good thing to call, to call out of like, yes, webinars are still a, a thing, but like, we’re not doing it the same way. Right? Mm-hmm. Then like you even said, like, you don’t even call it a webinar. I think again, like really getting clear on that language, in that messaging piece, but also the fact of like, instead of most people just send a replay.
But I listen to podcasts, so I would be more likely to just listen to it as a private podcast and go, go from there. And I love, that’s such a brilliant idea. But again, it’s like that innovation of like, how can we try different things that we’ve never tried? And then you’re, you’re leveraging the data that you’re getting to be able to determine your next, your next steps.
So I think that’s like. That’s absolutely brilliant. And so in regards to webinars for business owners that are wanting to, you know, leverage more of that and like ForeverGreen, what other ways would you say like have been like really successful for you with webinars?
Sam: Yeah, I would say that. You know, again, the way that I structure the webinar even, uh, is still working, but like, leading with value.
I think like the, the reason that webinars, you know, have gotten bad raps in the past is because people will come and they’ll get hardly anything and then they just get pitched all the time. Um, yeah. Telling people upfront that they are going to get pitched at the end, uh, benefit. I think that it builds some trust and also you can like, ask for consent in a way of just being like, Hey, is it cool with you if for the next hour I’m gonna teach you how to legally start an online business?
At the end I’m gonna share about the ultimate bundle. If that’s not cool with you, it’s probably a good time for you to go. Everybody else, let’s hop into it and everybody stays. So I think just like being upfront about it, I’m not trying to like do smoke and mirrors or something like that. People will often ask me, like in the comments like, is this actually live?
Are you here? I’m like, yes. I, so I make sure that I stay like really engaged with the chat and everything too. Like just making people feel seen and like, I think appreciating that people are busy, that they have a lot going on, and that they’ve taken time outta their day. And so. That’s part of where the podcast idea came from was like trying to meet people where they are for the commuter, for the busy parent, for the person who’s trying to get food on the table and like also start a business on the side.
I’m like, okay, let’s do podcasts. Like that’s fine. You know, just meeting people where they are. So I think those have been. Some of the ways, the other thing that I would, that that’s been working really well is like we send out an email before the webinar. So after someone signs up and then there’s like a, a show up sequence that goes out to them and we ask people, what are you hoping to learn about on this webinar?
And that’s really helpful for yet again, another source of like. Voice of customer kind of research, but also it’s an opportunity for me to now start engaging with them. So either writing back or sending a video back on, like video ask or something, um, saying, Hey, that’s actually something we’re gonna talk about in the training.
That’s a really good question. I hope that means you’ll show up. So, increases show up rate and increases engagement.
Akua: Okay. I love that so much because one of the things that I wanna highlight that like that just popped in my mind is of how much personalization and accessibility you’re giving your audience.
And I think that’s so needed now more than ever, people are craving that connection with the person that they’re buying from. And so also to like making them feel seen, making them feel like they’re one of one, like the only person that you’re talking to. And I love that you shared that because I think that’s such an important thing for business owners of like, how can we make things more personable?
And then also too, like how do we. Give more of an accessibility to where we can connect with our audience deeper to where they’re more excited to be a part of the webinar because they feel seen and they’re like, oh my God, this person just answered my question. I wanna know what else they have. You know what I mean?
And I think that’s such an important thing. I wanted to know more about what like evergreen looks like to you. Because again, like these steps, all, all of the work that you are putting into these webinars, everything has, again, to your point of like this compounded interest to where now you were able to have a business that runs on its own.
And so for you, like now that it’s. You have that? What is, what is, what does your business look like now? What does life look like for you now?
Sam: Yeah. I would say like my business has been relatively the same for about the last two years, which I’m okay with because both of my parents died within the same year, two years ago.
So then that just completely knocked me out, to be honest, and was like, I just, I just don’t want to grow at this point. So it was really like a, I’ve been in a maintenance phase ever since, but what that looks like is creating. High, hopefully high quality, but high quality, um, content that again, has that call to action to either watch my workshop.
I still have the same workshop. I have other freebies. I have 50,000 people on my email list, so like driving traffic to that list and nurturing that list. Um, I have a free newsletter that goes out every Tuesday called Sam Sidebar, so like, just nurturing the heck out of them and really like, again, it was another one of those time periods where I’m like.
What matters, what doesn’t matter? Like what can go, what do I actually wanna focus on? And then just like really pour more of myself into fewer things. So I have a lot of time and flexibility. It’s funny, like the next couple weeks are actually super busy, but that’s not typical for me because I’m just getting all the prep work done for the live webinar that will be on October 20th.
Mm-hmm. Um, but that’s not con, that’s not usual for me. So that’s the way I want it. Uh, to be honest, I. I have had a multi seven figure business every single year since 2019, but I take beach days when I feel like it. I travel, I am not on my phone a whole lot, uh, trying to be on my phone a whole lot less.
Even I just bought a cottage up in Vermont, like trying to get off the grid as much as possible. And so, uh, yeah, I’m, I’m pretty like slow and chill. I don’t wanna, I have no desire to like. Do anything crazier than this. Yeah,
Akua: but I,
Sam: yeah,
Akua: but I love that. I think, yeah, you know how you just like defined. What success truly looks like for you.
And I love that you should have like, look, I’ve already had a multi seven figure business and I realize that that didn’t work for me. And that is okay. I think a lot of us as businesses and we see these big names with like these major successes and like, we think we want the same thing. And I love how you’re like, you know, I’ve experienced all of that and.
I don’t, you know? Yeah. And I think, and I love that you’ve really truly built something that aligns with you where you’re like, all right, like I have my beach days, I have this cottage. I can just truly be like, where you don’t need to be more, you’re just Sam. And I think that’s just such a beautiful thing, like honestly, and I think that’s one of my goals too, even as a business owner, just to have that like, and so for you, especially like you’ve experienced so much where you said that you’re maintaining your business, grief is such an interesting complex.
Thing. Mm-hmm. You know what I mean? And like how do you navigate grief also too, while still managing your business?
Sam: Oh man, it is so hard. It’s so hard because I think the biggest thing, I actually, I have a podcast episode coming out about this next week, about like how grief has impacted me as a person, which then like trickles down, like how it’s changed me as a person, but I think permanently, my therapist says no, but we’ll see.
But I, I don’t I to differ. Yeah. I tell her every week. I’m like, I don’t. Think so, Susanna, but um, yeah, she, but she, she claims it’ll get better, but we’ll see. But it’s changed me a lot as a person and then that obviously has changed how I show up as a business owner. So like mm-hmm. I think one of the hardest things is that, especially for our job and like what we do is so oddly unique.
That it’s so outward and like, you know, you’re supposed to be like happy and chipper and like be on camera and look good and like look put together and face to camera, video and mm-hmm. There’s just a lot. And it’s also a lot of outward energy, like beyond just the content creation. I then have like 5,000 customers, so it’s like I’m supposed to also hold all this space for a lot of other people.
Oh. And then I have a team too, so like a whole, that whole situation. So that’s, that’s just a lot. And like I realized that. The way that I think of it now, maybe this is a really bad analogy, but the way that I think of it now is almost as if I’ve had an injury that has left a permanent mark. So like if anybody’s ever had an injury that then you have surgery for like, I don’t know, you tear your rotator cuff and then you have like rotator cuff surgery.
It’s never the same. Like it’s just not the same. And so you have to like compensate and do things a little differently and rehab it. That’s, to me how grief feels as a business owner is. Like, I’m just not the same. I don’t have the same output, I don’t have the same capacity or flexibility. Um, and. I have to, like, I’ve really had to like get to know my new self essentially of being like, oh, old me.
Like, talk about not comparing yourself to being like, I was really hard on myself for a long time. Be like, oh my God, I used to be able to record like four podcast episodes in a day. What’s wrong with me? You know? And now it’s like, I can’t do that anymore. That’s okay. Um, so kind of just getting used to that.
And yeah, learning my limits with like, I travel a lot to give talks and do all this stuff, and now I know more about, you know, kind of what I need on those trips and how I’m gonna feel and all of that. So yeah, it’s, it’s really, it’s really changed me I think a lot.
Akua: I, I, I really appreciate like your transparency with that because you know, especially people who have experienced such tremendous loss, like you aren’t the same person, and you said like, I have to get to know the new person, which in turn changes completely how I run my business.
And I love that you share two of like being a lot more intentional with the capacity. I think that’s, I think that’s been been the biggest piece. I know like for me, like I’m recovering from burnout and. Uh, I think that’s something a lot of business owners struggle with is understanding their capacity.
And so, and I, you know, obviously two very totally different situations of course. And so like for you as like you’re navigating, how have you been much more aligned with understanding your capacity? Not only understanding it, but also honoring it? Because I think sometimes we’re like, well, I gotta really get this done, or people are really relying on me.
You know what I mean? Like, like to your point of like where. We’re not having that grace for ourselves. Like for you, what, what, how did you, how have you navigated that and any advice that you have for business owners of just getting more clear about our capacity and honoring it?
Sam: Yeah, I think it’s about working on your detachment from, like tying your worth to your output or tying your worth to your business.
Any of your business’ metrics, uh, any vanity metrics that are associated with your business, like. Because the moment you start to do that, you start to have this kind of like, so what conversation? Like I wanted to take a couple of weeks off my, I’ve never taken a break on my podcast before, and so I had done four years of weekly episodes and had many periods during those four years where I’d actually posted more than one episode a week and mm-hmm.
Yeah. It was just like, I wanna take a break from, I wanna have like a little summer break from the podcast. It’s okay. And like, but, but old me and, and I had this come up, but I’m just able to quickly squash. It would’ve been like, but the downloads and the, you know, and I have momentum. Like my podcast started to grow more recently and like, so now if I stop posting, then everyone, oh my God.
I think it’s just like starting to realize like, so what? Like it doesn’t, the stuff just doesn’t matter. It’s okay. And I guess I got more confident too that like people will stick around. You also realize like. People don’t care nearly as much as you think. Like we build ourselves up in our head and think we’re the center of the universe, but news slash we’re not.
So, you know, it’s, I think working on some of that was the most helpful. Mm-hmm. Um, and just really taking what I call like an athlete mentality to being a business owner as well as like caring for yourself in a way like a professional athlete would, like blocking yourself off more from what’s going on around you.
Like kind of, I always give the like an analogy of how tennis players, when they are in between sets, they’ll sit on the sidelines and they’ll put a towel over their head so that they actually can’t see or hear like all of what’s going on. That’s kind of what I picture. Like we need to do to protect ourselves in addition to the normal stuff like eating well and like drinking enough water, fueling our bodies, like being outside every day, taking walks.
Like I, I considered that stuff to be equally as important to like getting that podcast episode done. So I think that’s what really helps to shift that mindset. I,
Akua: I love that. I think having that athlete, like you said, having that athlete mentality of, and that people just don’t care as much as you do.
Like the right people are going to stick with you through, through and through, and like they know, like as business owners, like you’re also human. And so life happens. You know what I mean? And the, again, to your point of like. Uh, people are gonna ride with free regardless. And I think that’s such a beautiful thing.
And like how you say like, to it’s equally just as important, um, to go on walks to take care of yourself. And like for me, like that’s something too, like, I literally, like, to me now, I feel like it’s even more important sometimes. Mm-hmm. Yeah. Than my business. Like, you know, like today before I had my interview, I was like, okay, I woke up a little bit later than usual, which is fine.
Like this is obviously later in the day, but I was like, I gotta get my workout in and I gotta take my pup for a walk. Like, I have to do that before anything else because that truly. Is like how I can function and have this conversation with you. Yeah. You know? And so again, like really making, like, the thing is, I think we forget too as business owners that we really do deserve the life that we like, like the life that we want.
You know what I mean? And I think that’s just such an important thing of like, you matter in the process. And so continuing to honor yourself and, and, and your capacity. And so when you, I know you mentioned too earlier, like obviously like your life is. There’s been so much that’s happened in the past two years and you said like you’ve been maintaining.
When you look at the future of your business, do you see yourself maintaining or like where do you see like what’s next for you as a business owner?
Sam: Yeah, I’m, I’m kind of curious and open, like I, I can see what I do expanding a little bit that like, especially since my book came out, um, in April called when I Start My Business, I’ll be Happy.
I, you know, the book really, like we talked about is about business and so I. I gotten like a lot more of demand and requests for talking about more business work, like a lot of the stuff that we’re talking about today. Yeah. And not so much the legal stuff, so I can see it expanding in that direction. But I also think writing my book then gave me a little bit of this like, fever for like, wait, what if I wrote another book, but maybe even like a different topic.
So I, I think I, I would like to write more. I’ve been writing more like privately and. Really just trying to develop more of the craft. Also teaching myself how to write more for fun and not for consumption, just to like get in more of a creative act and habit. Mm-hmm. Um, so yeah, I could see it expanding in that way.
I think my, like big dream would be for my podcast, uh, on your terms and whatever I write to be my main thing that would be, I, I love to write and I love podcasting, so that, that would be like my hope for the future.
Akua: Yeah. No, I love that. It seems like, you know, like you’re leaning into the things that light you up and bring you joy.
Yeah. And when you think of your whole journey of craving this book that really just is a testament to everything that you’ve been through, what is the major thing that you say that you’ve learned about yourself?
Sam: Yeah. That I, I am, uh, tenacious. That’s for sure. I mean, I will get stuff done. I’ve been through so much and I.
Don’t seem to get knocked down. I mean, part of that is like a admirable, I mean, the whole thing is admirable, I guess. But I, I guess I should say that part of it comes from like, I experienced a lot of trauma as a child and so I’m also kind of used to having to continue to operate, which can mean skipping over like, and processing and not processing and like not talking about what’s happened.
And that can lead to a lot of burnout. So like I am also somebody who’s trying to be like. You know, sometimes when my life gets like a little quiet, I then will add on things. Or even when it gets busy, like when I got my book deal, I all of a sudden was like, oh, you know what I should do, sign up for my first High Rocks competition in Chicago, which is what I just did back in November in Chicago.
And it was like, who on Earth thought that this was a good idea? Well, I was writing this book, I did. So I think it’s like really. Yeah, just working on that.
Akua: Yeah. I just have, I, I really like, have loved, just like, just hearing about your whole journey in general because I think it, like, again, it’s a true testament of what it really takes to be a business owner.
Yeah. And just shows again, the layers to being human and how you just consistently navigate that. And I love that you talked about the trauma and the grief because if you are not right here and if you are not right here, you don’t have a business. You really don’t. Yeah. Like at least a sustainable one.
You can only get so far. And I just love that you just highlighted that. I think like everything that you’ve shared and even too with your book, it’s a, it’s a perfect testament of that. It really is of just like you yourself have to be whole. You yourself have to be aligned and also to like really, um.
Honoring yourself and where you’re at I think is the biggest piece because we put such unnecessary pressure on ourselves. And I think the biggest thing for me has been like accepting myself that as I am right now. Mm-hmm. Because I also found myself also too, like which, have you ever felt that way as well?
Of like where you are, you like, I can’t celebrate until you this, a certain version of yourself, like this perfect version or whatever. And I’m like, cool. Like how I am now is good so I should, I should celebrate that lot. Like now. Is that like pretty common for you as well?
Sam: Yeah. I think for so many of us who are, I mean, I think it’s probably no coincidence that like people who wanna start their own businesses are also like overachiever, perfectionist tendencies, you know?
Yes. And so we constantly, I mean, that’s why I titled the book what I did. Like when I started my business, I’ll be happy because I know that when I started my business, I thought that was going to be the answer to all of my happiness. And so, and then it’s like. Hilarious. You know, in a non hilarious way.
What ha what has happened to me in my life since then? It was such a beautiful opportunity to realize like, oh, it’s not going to be that thing. And it’s never mattered how much my business made, like my business, making a lot of money, didn’t make anything about my dad’s situation be any better. It didn’t make the fact that my mom was killed right after my dad any better.
Mm-hmm. Like none of it mattered. So it really pushes you to focus on what actually matters. But yes, I can. I can totally relate to that.
Akua: Yeah, and I love that. I love that you shared that it really forces you as a business to focus on what matters. Because like I said, we get caught up. We get caught up all the time, like, I gotta hit this specific revenue goal, I gotta do this, and I gotta do that, or I gotta speak on this stage, and all of those things.
When life happens, like it does not matter. You know what I mean? It’s like those hard moments that nobody sees. Like, can you still show up? Like, you know what I mean? Like, and you’re forcing yourself to have to show up still. Like those, that’s a hard, that’s a hard thing. And you know, and I think we, I, I just, I appreciate you so much of just like sharing your story in this book.
Like, you know what I mean? I think it’s gonna truly, truly, like it’s been making an impact and I think that’s incredible. And so we’re gonna play a game like, because I just. Yeah, this is fun. Kill it. I love this conversation so much and so we do it rapid fire and so I’m gonna ask you a series of questions.
Don’t think about it.
Sam: Okay. Ready?
Akua: Just whatever instinctively comes to you. Okay. So obviously you were, you’re lawyer, and so one belief that you had as a lawyer that you now totally reject.
Sam: That being a lawyer makes you a lot of money.
Is that on par with what we’re going for?
Okay.
Akua: Okay. Okay. What is your go to coffee order?
Sam: Oh, I love cappuccinos and in the summer I’ll take an iced cappuccino. Ooh, okay. Okay. I like that. If you had to describe yourself in three words, what would they be? Oh, god. Dry. Sense of humor. I mean, not like physically dry, I meant dry sense of humor. Um, adventurous in food motivated.
That’s me
Akua: too. I’m always like, when I’m upset, just feed me. Always forgiven. Oh my gosh. Okay. So what’s a totally random skill or hobby? People would be surprised to know that you have?
Sam: Hmm. Well, I can wiggle my ears. That’s one what? I can wiggle my ears. That’s a good, like, skill. Not I can see it, but you have your headphones in so I can’t see it.
Yeah, I know. And I can, I can’t do it when I’m smiling. That’s the other problem. But no, that’s one, that’s to the skill that I have. I, I was a volleyball player my whole life and I got to go to China to play volleyball, um, when I was 16. Oh gosh. Amazing. Okay. What position did you play?
Akua: I
Sam: was a setter. You were set?
Or how tall are you? Yeah, very short. I was five four, so I worked my butt off. I worked my butt off. I can jump through the roof though. Oh my gosh. Okay. Uh, hi. We’re twins. Did you play, did
Akua: you play volleyball? I did. That’s awesome. I did. Um, I played one year collegiate college, like in college, collegiate.
And um, I’m also five for, and I was right side. Because I could jump. Oh, that’s cool. Very high. That’s yeah, yeah. Right side. And so, um, but then obviously get to college and I’m too small, so I had to be libero, so same. But yeah, I know you get it, so, yeah. No, that’s amazing. Okay. Okay. Love that. Okay. What is the boldest decision you made that would’ve terrified your past self?
Uh,
Sam: leaving the law to start my own business. Yeah.
Akua: Yes. Love that. Okay. What’s one daily habit you now protect, like your life Depends on it.
Sam: My bedtime routine, I have a killer bedtime routine. Okay. Now I wanna know. It’s not, it’s not that crazy or anything, but I, I am, you know, like usual, I have my little, little like skincare routine ’cause I do my more intense thing at night.
The idea of being that in the morning, all I do is like splash water and put SPF on. Yeah, so I do my skincare routine. Obviously I brush my teeth. I’m good in case my dentist is listening. And then, um, I do a 10 minute meditation on the Peloton app. I love Peloton so much, but I love their meditation teachers.
I love a Didi Shaw. And so I always do hers. So I do a 10 minute sleep meditation, and then I usually read, um, until I fall asleep and I have like a special little like reading light that goes around my neck so that it doesn’t like stimulate me too much. Yeah. Um, and usually I just start to get really tired and I’m like out like a light very quickly.
But yeah, nothing too crazy, but that’s my routine.
Akua: I love that though. Okay. Okay. And skin is glowing, honey, so it’s working for you. Thanks. Thanks. Hard work is paying off.
Sam: Yeah. I know Shout out to Primarily Pure. I love their stuff.
Akua: Yes. Oh, I love that. Okay. Guilty pleasure. TV show or podcast you’re obsessed with.
Sam: I love Great British Baking Show on Netflix. I don’t know if that’s a guilty, but it’s like. It’s the Coziest show in the world. It just like makes me feel like everything’s gonna be all right, which I am not currently feeling. So I, I feel like when I watch great British Bacon, I’m just like, wow, the world is good.
People are nice. Everything’s gonna be fine. I know. Yes, yes.
Akua: My show is Abbott Elementary. That’s, oh, I love it. I know that puts me in a good mood. My Quinter Brunson
Sam: and I went to the same undergrad, and she’s from Philly and I’m from Philly, so I love her. Yes. Yes. I
Akua: know
Sam: that show.
Akua: You know, that puts me in a good mood.
I’m like, yeah, I was saying every little thing. All right. Like every single time. I just think that’s what I myself all the time. I’m like, oh my gosh, you guys. I’m sorry. I just saying that was really cheesy. I might have Hailey cut that out.
Sam: I love Ava so much. I was hoping she was gonna win the Emmy the other night.
I know. Uh, I know she
Akua: deserved it. She really did. Yes. Mm-hmm. Oh, this has been so fun. I’ve loved this conversation and, um, thank you so much for, for. Entertaining me with this rapid fire. That was fun.
Sam: No, thanks
Akua: for
Sam: doing it.
Akua: Yeah. Okay. So every single, uh, episode, we’d love to end with this question is, what does having an unbreakable business mean to you?
Sam: Mm. Having an unbreakable business to me means not having a business that’s dictated by anybody else’s definition of success or what I should be doing, and really doing what you know is in alignment with me and my values, but also what supports my, my life, and my lifestyle.
Akua: I love that you kept it short and sweet.
Okay, girl. I love it. And Sam, this conversation has been, honestly, I think I, I definitely needed it because I, I just loved how honest you were, how real it was. And I think just showing. The really behind the scenes of what it truly takes to run a business, especially when life is so unexpected, when life just comes and can, hits you hard.
Um, you know, because it, these are things that we can’t avoid as business owners. Life will, will, like, all of us will experience grief. All of us will experience a lot of these things. And I think that I appreciate you so much and also you writing this book because it highlights that and I think that’s something that we need to remember as business owners.
What matters is that resiliency and how we continue to show up even when life is attempting to knock you down. So I appreciate you so much for coming on the show.
Sam: Thank you so much for having me.
Akua: Yes. And for those that wanna connect with you, where can they find you? Where can we buy your book? Please tell us all the things.
Sam: So you should definitely sign up for my free weekly newsletter, Sam Sidebar. You can just head to sam vander melon.com/sidebar, or obviously the link will be below. You can grab my book, um, when I start my business, I’ll be happy anywhere books are sold and come over and listen to my podcast on your terms.
Um, since you love listening to podcast.
Akua: Yes. Oh, well, Sam, thank you. Thank you so much. I’ll be putting all of this in the show notes you guys, so make sure to connect with Sam and for everyone listening. Until next time, thanks for tuning into Unbreakable Business. If you love today’s episode, don’t forget to subscribe, leave a review and share it with someone who needs a little extra inspiration.
Remember, no matter what life throws your way, you have the power to. To keep going and your business can be unbreakable too. Until next time, keep building, keep growing, and stay unbreakable.


