Young and Profiting (YAP) with Hala Taha
Krista Williams & Lindsey Simcik: When Friendship Is a Business Superpower | Entrepreneurship | E353
Mon, 02 Jun 2025
Starting a business with your best friend might sound like a recipe for disaster to many entrepreneurs. But for Krista Williams and Lindsey Simcik, that’s exactly how their journey into entrepreneurship began. With just a $15 recorder and a tiny closet, they launched Almost 30, a podcast that quickly grew from a side hustle to a thriving business. In this episode, Krista and Lindsey reveal how they navigate their “business marriage,” scale their podcast, and achieve lasting success as both entrepreneurs and friends. In this episode, Hala, Krista, and Lindsey will discuss: (00:00) Introduction (01:12) The “Business-Marriage” Dynamic in Partnerships (07:12) Building Healthy Communication as Entrepreneurs (13:45) Almost 30: Scaling a Podcast from Scratch (19:39) Balancing a Side Hustle With Full-Time Work (27:13) The Power of Community in Podcast Success (37:47) What Is the Saturn Return? (41:55) Navigating Friendships in Entrepreneurship (45:41) Pivoting Your Career With Purpose and Clarity (56:26) Shifting Your Money Mindset for Financial Freedom Krista Williams and Lindsey Simcik are the co-founders and co-hosts of Almost 30, a top-rated podcast focused on personal development, relationships, wellness, and spirituality. Individually, Krista leads It’s Krista, an online business with coaching services for women, while Lindsey runs New Mom on the Block, a platform dedicated to supporting new moms on their motherhood journey. Their debut book, Almost 30, offers practical tools for navigating change with confidence. Sponsored By: Shopify - Start your $1/month trial at Shopify.com/profiting. Indeed - Get a $75 sponsored job credit to boost your job's visibility at Indeed.com/PROFITING Mercury - Streamline your banking and finances in one place. Learn more at mercury.com/profiting OpenPhone - Get 20% off your first 6 months at OpenPhone.com/profiting. Bilt - Start paying rent through Bilt and take advantage of your Neighborhood Benefits by going to joinbilt.com/profiting. Airbnb - Find a co-host at airbnb.com/host Boulevard - Get 10% off your first year at joinblvd.com/profiting when you book a demo Resources Mentioned: Krista and Lindsey’s Book, Almost 30: bit.ly/Almost30-LK Krista and Lindsey’s Podcast, Almost 30: bit.ly/Almost30-apple A Happy Pocket Full of Money by D.C Gikandi: bit.ly/AHappyPocket Active Deals - youngandprofiting.com/deals Key YAP Links Reviews - ratethispodcast.com/yap Youtube - youtube.com/c/YoungandProfiting LinkedIn - linkedin.com/in/htaha/ Instagram - instagram.com/yapwithhala/ Social + Podcast Services: yapmedia.com Transcripts - youngandprofiting.com/episodes-new Entrepreneurship, Entrepreneurship Podcast, Business, Business Podcast, Self Improvement, Self-Improvement, Personal Development, Starting a Business, Strategy, Investing, Sales, Selling, Psychology, Productivity, Entrepreneurs, AI, Artificial Intelligence, Technology, Marketing, Negotiation, Money, Finance, Side Hustle, Mental Health, Career, Leadership, Mindset, Health, Growth Mindset, Startup, Passive income, Solopreneur, Founder, Networking.
Chapter 1: What is the 'business-marriage' dynamic?
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Being an entrepreneur is not easy. The entrepreneur has a different type of mindset. The number one thing that you can remember and accept in life is that your friendships are going to change and that's okay.
We started recording on our closet floors. It was not perfect. It was not organized. It was a mess, but it felt so right. So if we had waited to start until we got a studio, had the business all set up and the strategy right, like we would have never started.
A lot of people want to be an entrepreneur for the idea of what being an entrepreneur is. They kind of see what's happening online on social media. They're like, oh, you work from home or you work on the beach or it's sexy. It's not like that. Why do you feel like most of these business marriages don't work? If we just love each other, this will be fine, right?
But then you get into the marriage and you're like, oh, this is a lot of work. The most important thing that people need to look for in relationship for entrepreneurs is... When we first started, I was so insecure about it.
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Chapter 2: How do Krista and Lindsey communicate effectively?
But I think what I realized was that as an entrepreneur, you're meant to... I know if I can make this much here, if you give me 40 hours a week, like, watch me.
Like, there's no limits how much money I can make.
If you guys go do your own things, do you get jealous or competitive ever? It's all gonna come out right now. Young and Profiters, welcome back to the show. Today, we've got an in-person episode with Krista Williams and Lindsay Simsek, who are the hosts of the Almost 30 podcast. Now, this is a podcast that they started nine years ago on their closet floor.
Now, it's one of the top podcasts in the world. They've got a thriving online community. They've got so many different revenue streams. They've built an incredible business around their podcast. So in this episode, we're gonna talk all about that. We're gonna talk about career pivots, the pivotal period of your Saturn return right before your 30s and how you can navigate that.
We're also gonna talk about relationships, work marriages, and so much more. We get really deep in this conversation. I think you guys are gonna love it. Without further delay, here's my conversation with Krista and Lindsay. Welcome to Young and Profiting Podcast, Krista and Lindsay. Thank you. We're so excited to have you guys. So excited.
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Chapter 3: What are the challenges of scaling a podcast?
So as I was researching for this interview, I found out that you guys say that you're in a marriage. And you guys recently joined the App Media Network. You know that I also have a business partner, Jason. I always feel like we're married even though we're not romantically married. But talk to me about why you guys call yourself a marriage and what does that really entail?
When you're in business with your best friend, especially, there are so many layers to the dynamic. And in a marriage, as you know, when you get married, you share finances, you share just deep growth and learning in all aspects of your life. And when you become entrepreneurs as best friends...
you start to share finances first and foremost, and then you get into the deep work of becoming confident, successful entrepreneurs, which requires you to really look at every aspect of yourself and every aspect of how you are in relationship. So Krista and I have been through therapy. Oh my gosh. Through coaching.
We have had really, really hard conversations about finances, about our vision for the future. Yeah.
about what's working and what's not working yeah and so there have been many times where like the lines are blurred i'm like i kind of want to be more of your friend right now yeah we're in a business conversation yeah and vice versa so it's been something we always have to actively participate in and actively work on yeah if you think about our marriage almost 30 is our baby
So with parents, sometimes we prioritize almost 30 our baby over our relationship. And so we're more in that role of the parents of our baby than we are as friends. And so it's sometimes felt like we've lost sight of friendship because we're so focused on the business and the growth of the business. And we also have to focus on aligning our dreams and visions for the future.
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Chapter 4: How did they balance a side hustle with full-time work?
In a marriage, you have to continue to come back to like, where are we going? How are you feeling? Where are we going? And we have to do that all the time. So whenever people want to start businesses with their best friends, I'm always hesitant to tell them to do so because most of the time it fails when people do that. And we've been really lucky.
We put in the work during the process and it's been the most beautiful relationship of my life, but it's not easy.
Wow. I love that you guys are sharing this with us because it's so interesting. Why do you feel like most of these business marriages with your best friends don't work? What makes you guys work?
So I think for most of us, the ideas that we were told about marriage were from Disney movies, were from media, were these ideas of marriage and relationships that are not actually real or supportive of healthy dynamics and relationships.
You know, we could essentially be in an unhealthy marriage forever, she and I. But what we want for our lives is to be happy, to be fulfilled, to do something great.
So now we came into our relationship, our marriage, with the idea of marriage being something where you sacrifice, you're not in alignment, you don't speak your truth, you don't ask for what you want, you don't create something amazing. And so a lot of people go in with that thought, like, this will just work without work.
I went into my previous marriage, I was married, and I kind of had that idea, if we just love each other, this will be fine, right? But then you get into the marriage and you're like, oh, this is a lot of work, a lot of checking in with myself, checking in with you, realigning our values.
And so if you go into a business partnership without checking in on the relationship, checking in on the values, checking in on the direction of where you're going, you're it's not going to work. Something's going to happen. You're going to build up resentment and you're probably going to end up breaking up.
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Chapter 5: Why is community important in podcast success?
I think the most important thing that people need to look for in relationship for entrepreneurs is being able to communicate. Just like a marriage, the number one thing in relationship is communication. You need to be talking about how you're feeling, what's coming up for you, what you want, where you want to go, what works for you, what doesn't work for you.
And we've really focused on our communication and communicating respectfully and with love and with intention. And that's been the biggest thing that's really kept us together.
That's so interesting. Talk to me about the communicating with love and respect. So if you guys are having a disagreement, how do you guys approach it?
Yeah, we coined this phrase called clearing conversations. So this practice where there's usually something funky in the air, we're kind of feeling like something is off. And we will schedule a walk and a walk because I think sitting down across from each other staring into each other's eyes can be very intense.
and kind of activate the body in a way that doesn't really support honesty and flow in a conversation. So oftentimes we'll go on a walk, we're moving our bodies, we're next to each other, and we're able to look at each other, but also like give each other a break.
And our intention in these clearing conversations is to bring truth and respect, to be a great listener and really have it be an experience of us against the problem rather than Chris does the issue. We got to get to the bottom of it. And that's really helped us because we all have egos. It's a thing.
Yeah.
And so when you approach a problem, it's easy to be like, you know, you did this to me and you made me feel this way. But in these clearing conversations, we are very intentional to use I statements. The story I'm telling myself is that you don't care about this part of the business and I have to take it all on by myself.
And in sharing these I statements, I'm able to see under the hood of like, what's been turning in Krista's mind. And then I'm able to say, oh, wow, if I believe that I would be feeling that way too. And it just gives us an opportunity to not only share our experience, but then to listen.
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Chapter 6: What is the Saturn Return and its relevance?
So I got a chance to get to know you guys because we were doing negotiations for Yap Media. You just joined my network, which is just so exciting. We're so excited. And it seems like you guys wear totally different hats. Like I remember at one point, Lindsay was like, I'm going to handle the contract stuff. And you have your own stuff that you're handling.
So talk to us about how you divide the labor and how you think of that with your company.
Yeah, I think getting clarity on that is really important for any business in general and for really any business partners, especially. For us, the way that we delegated roles happened naturally, but happened very early on. So my experience was in the corporate. I worked in finance management consulting, and I actually was doing some brand deals on the side as a blogger.
And Lindsay was an actress. She worked at SoulCycle. She was an amazing performer. She knew a lot about production. She knew a lot about performance. She brought a lot to the table from... the aspects of the business of creativity that I didn't really have access to. So early on, I was like, I'm going to take on more of the business strategic part because that's where I was living before.
Chapter 7: How do they navigate friendships in entrepreneurship?
So I actually had it backwards. You're more of the business. Got it.
Okay. And then Lindsay brought more of the creativity. So when we started building the business, it was like... both of us working together. And then we saw where we were fitting naturally and we claimed the domains. And over the years, we had to reclaim domains of where we are and where we work because we were trying to overlap for quite a bit. And that doesn't really support us.
You know, it doesn't really help for us to both be two cooks in the kitchen. So I'm more strategy. I'm more of the partnerships. I'm more of the overall ideas that we have that move the business forward. And Lindsay is so helpful with the creativity. She's so helpful with the relationship with the team. She's a great communicator with the team.
So there's just stuff that she's naturally good at that she brings to the business.
Yeah. Do you guys, have you ever heard of Mind Pump, the podcast? Yeah, we love them. Okay, so Adam Schafer came on my show. Love them. And it's four guys that talk about fitness, health, And he was telling me that they're invested in all of their businesses together outside of just the podcast. So they all invest in real estate, stocks. One of them wrote a book.
They all get royalties, even though they did nothing for the book. And they're just embedded in business together, no matter what the endeavor is. So how do you guys look at it? I saw you have like a new YouTube channel. If you guys go do your own things, how do you think about it? And do you get jealous or competitive ever?
I know, honestly. You know, I've been thinking about this.
Well, I think what's so interesting, you know, when we started Almost 30, we were going through a very specific time in our life and the show has evolved as we have evolved. And I think with that evolution too comes our own very unique gifts and how they want to be expressed in the world.
So Krista has an incredibly successful coaching business, retreat business, and so many of her gifts that could not be truly fully expressed in Almost 30 are now being expressed through those businesses. And I'm exploring this new season of my life of motherhood and what that might look like in a community and brand sense. So thankfully, we've always just been very, very supportive of the other.
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Chapter 8: What mindset shifts are needed for financial freedom?
So that type of business model wouldn't really feel good for me. But Almost 30 has helped us as a foundation show us what we're good at and show us what our audience wants more of. For motherhood, obviously they're going to see her. She's an amazing mother. She's built an amazing family around that. So they want more from her in that. So she's like, okay, cool.
I'm noticing this thing that Almost 30 is providing for me. What can I do more of in that? For me, it's the coaching and retreats. How can I build more of this? And so it just allows us to be more robust of who we are and evolve in the business and pour more into the business because we're happier.
You know, if you're kind of just looking to the business to feed and satisfy every one of your creative needs or pursuits, that doesn't feel true for me. I think having creativity spark and then going where it needs to go is what I like to do instead.
Yeah. I like that you guys are doing your own things outside of just almost 30. Because you have been doing this for, what, nine years now? Mm-hmm. Has there ever been a moment where you're like, I just don't think we can do this anymore? Was there ever like a struggling point? Because I know in entrepreneurship around the seven year mark gets really tough. Did you guys have a tough moment?
You know, what's funny is we've been honest with each other about what life looks like past almost 30. But we've never had a moment where we fought or something happened where we wanted to throw in the towel. Like, yeah, we've always been very conscious about where this process is. And thankfully, we have a book coming out. So like,
The book feels like such a beautiful rounding of the 10 years we've been doing this. It's like all of our life's work. So we've really trusted that. And I think it's normal to feel like quitting, but it's actually just weird. I think that's what happens for me when I'm expressing myself creatively in other aspects of my life.
And I'm not holding this relationship to be the only thing that sustains me. It's just like romantic relationships. If she's supposed to be everything to me, if almost 30 is supposed to be everything to me, I'm not going to be satisfied. I need other things. I need other people. I need other creative outlets. And because we've both done that, we both feel satisfied.
And we come back to the relationship excited to be here.
Yeah. So let's talk about how Almost 30 started because I think there's a lot of life lessons that we can learn in that in itself. So tell me about how you guys first met and came up with the idea to start the podcast.
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