Introduction to Perfect Pitch Podcast
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There has never been a more true axiom in the startup world than this.
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The only constant is change.
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And when things need to change, it's up to the founder to get it done.
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Today, we're talking with CEO and founder Rachel Nilsson of Rags and investor Kurt Roberts from Kickstart to give you both sides of a perfect pitch.
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What is Perfect Pitch?
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It's a podcast from Kickstart that reveals the minds of both investors and entrepreneurs throughout a startup's journey.
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So whether that's uncovering what everyone's really thinking during a startup pitch or learning how entrepreneurs like you have managed their first major roadblock, Perfect Pitch offers an honest, quick, and tactical guide to help you on your startup journey.
Meet the Guests: Rachel Nilsson and Kurt Roberts
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I'm your host, Karen Zelnik, and you're going to love today's guests.
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First up, Rachel Nilsen of Rags.
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We're so excited to have you here today.
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So we're going to get into the details of your founding story in just a second.
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But basically, in summary, you took the pain point of parents having to get their kids, you know, sometimes multiple kids, very wiggly kids, dressed, and you solved it better than anyone else out there.
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So I'm really excited to dive into that.
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So glad you're on the show today.
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Thanks for joining us.
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I am so flattered to be here.
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I listened to the hook and it's like, I can't wait to listen to all the other episodes.
Kurt Roberts on Investment Focus
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Hopefully everyone else feels the same way.
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And then returning to the conversation this week is our investor from Kickstart, the guy who makes things happen, Kurt Roberts.
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Kurt, thanks for being here again.
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And for the people who are just joining us, give us a quick rundown of your investment focus.
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So I tend to focus on companies that are in the space of consumer products, marketplaces, health technology, and general business software companies.
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Well, we're really excited to have you here.
Founding of Rags by Rachel Nilsson
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You also join companies on motorcycle trips too.
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We've got one coming up in two weeks.
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That's so exciting.
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Kurt has this need for speed that is absolutely mind-blowing.
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We've gone skiing before and it's like...
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You see him at the top and then you get to the bottom and he's just been chilling for five minutes.
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And then he just, I'm not surprised.
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Well, I've heard you're an amazing mountain biker too.
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I've heard you also love speed and you're an amazing mountain biker.
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I can do the down, but I get smoked on the up.
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We already know this.
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I wait for her at the top and she waits for me at the bottom.
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It works out well.
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So let's just dive right into the discussion.
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Rachel, why don't you give us a little bit of background on your founder story?
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Where did the idea come from?
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Yeah, I mean, you kind of nailed it.
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It's a kid's clothing line.
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And my biggest focus in the beginning was just how do I create clothing that is comfortable, that functions well for both the kid and the parent.
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And really, there was nothing in the market that was like rags.
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So I made it myself, literally like in my parents' basement, out of my husband's t-shirt and put it on my toddler and posted it on social media.
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And back then, social media was like Wild Wild West.
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Everybody saw your content.
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And I started seeing this reaction with other moms and I knew immediately like there was something there.
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And not only have you made a really amazing product, but you also have this amazing community of your consumers who interact with each other and it's like a collection.
Rachel's Shark Tank Experience
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So I love... They've not built only a product, but a community around that to support that.
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I think that's really impressive.
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That was definitely secondary.
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I didn't expect that to happen, but it's also been just such a cherry on top.
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So what was the funding process like for you?
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The funding process?
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We're just going to jump right in.
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So I actually did Shark Tank.
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And that was really great for rags.
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And I knew going in that we were in a really good cash position.
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And I knew that the story would be intriguing.
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And I knew that the product was something that was interesting for people to watch.
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I wasn't fully sure I wanted the money.
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It was really, honestly, more just the network that I wanted to tap into.
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And obviously, when you go on Shark Tank, you're tapping into some pretty incredible networks when you're dealing with those sharks.
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And so at the end of the show, we talked back and forth and they did their due diligence and I did my due diligence.
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And they actually came back and offered me more money for less of a percent in the company.
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Who led your offer?
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You might mention... Robert Herjavec.
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I chose Robert mainly just because I saw that he understood the vision of the brand.
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And that is obviously what was important to me and still is important to me.
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And we were having these conversations.
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And really, the bottom line was, how much time could you give me?
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Can I tap into your resources and your network?
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And then I also called people that they invested in as well, which is shocking because nobody
Networking and Connections with Jeremy Andrus
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had ever done that.
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Nobody had ever asked, hey, can I talk to the other people?
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And so everybody that I reached out to, it was like, hey, if you don't need money, I wouldn't go that route because they're so busy.
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It would be really naive of me to go in and expect that Robert Herjavec is going to get on the phone with me anytime I need it.
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And that's really what I was craving.
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That's really what I needed.
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We parted ways and it ended up being really great.
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And we got the exposure.
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And I think it was ranked one of the best pitches on Shark Tank.
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That's not surprising.
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It's like purple hair, weird mom.
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They got their great ratings and we benefited because we got good exposure and I learned a lot.
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It was really, really scary.
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So it wasn't until like seven months later where I was at an event and I met Jeremy Andrus, who is the CEO of Traeger.
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We just started talking about rags and the business.
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And I could tell that he was genuinely intrigued.
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At the time, I really didn't know who I was talking to.
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Jeremy is a consumer king, and he understands that business and he understands branding.
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And I think it was almost a blessing that I didn't know that because I was very unfiltered and it was really natural.
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And so we just stayed in touch.
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And Jeremy at the time, his wife was pregnant with two twin boys.
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And it was kind of perfect because once she had her babies, I was able to... A package of rags arrived at the door.
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He was kind of in that same phase where he understood just dressing a kid could be annoying and stressful.
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And there was really nothing in the market that functioned like the rag did.
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So it kind of naturally evolved that relationship.
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And finally, I approached Jeremy and was like, Hey, I want you to help me.
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We battled back and forth because he wanted to invest.
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And I was like, Oh, I don't know if I want to take your money.
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It was like, I know that I'm in a healthy cash position.
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But I also know that when you take money, it gets really real.
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And I wasn't totally sure what I wanted to do at that point.
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And so I think Jeremy said you were probably the hardest person to close.
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So Jeremy actually is really close friends with Gavin and Kurt and the Kickstart crew.
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And they introduced me probably two weeks prior to closing.
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And I remember Kurt coming down and Gavin coming down and the rest of the gang to the office.
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I spoke to them about rags and it went well and obviously we're here so they
Role of Kickstart and Rachel's Investor Hesitations
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And I was like, there's just this is like another investor that I have the answer to.
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Like that already was stressful for me, you know.
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Bringing in Kickstart, it was unexpected.
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But the first year since we had brought Kickstart on, it was like, wow, they're so invested and so involved in a healthy way and so willing to help that it hasn't been investors being big, scary bosses.
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So I kind of feel that need of the relationship with the network you were hoping for with Shark Tank.
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That's why I did it.
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And then obviously, I think as an entrepreneur, you're faced all the time on the edge of this cliff where it's like, you're going to jump.
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I have never raised money.
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I have two great guys with an unbelievable network.
Hiring All-Stars for Company Growth
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I'm going to jump and see how this goes.
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Kurt, were you immediately interested in rags or was it immediately apparent that you wanted to invest in rags?
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At that first meeting, I think we got some sense about how crazy Rags' customers are.
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Like, truly crazy.
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Rachel showed us a video of some feedback from some of her customers, and we also got to see some pictures of
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that her customers have taken of their collections of rags sitting on bedroom floors at home.
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Which fill rooms upon rooms.
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Literally have people who have hundreds of these things for one child, right?
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So it's obviously like cocaine for moms.
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And so the fact that that was so crazy and that we were so impressed with Rachel and Rachel's vision for the business, it was a pretty easy decision.
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Rachel, I must have felt really good as a founder.
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Did you love all the interests that everyone had in you?
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Yeah, I think at the time I was super naive and this whole world was just so new.
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But that is immediate validation.
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So now you've got venture partners, your business is growing and scaling.
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As a CEO, what came next for you?
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What needs did you identify within your company?
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Oh my gosh, there's so many needs.
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I think the biggest thing for me was team, honestly.
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And I would say still in the phase that we're in now, we're still so little.
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The team is such a big deal.
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We have to have all-stars.
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We have to have starters.
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We can't have bench players yet.
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We need everybody to be a starter.
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And I would say that has been the biggest challenge and also something that I've seen once you hire well, you can scale so much quicker.
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And so you were looking to bring people onto your team.
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Can you tell us about some of your first hires and we'll kind of get into lessons learned with building a team.
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But can you walk us a little bit through that process?
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I mean, first hires, obviously, when you're a startup and you're working in your basement, it's going to be like family and friends.
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But I would say the first real hire was maybe a couple years in.
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And absolutely a million lessons learned.
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It's almost like one of those things that you don't want to learn, but you do.
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And you kind of have to go through it in order to be better.
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And it can be super painful, but it also can be really rewarding too.
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It gives you almost this confidence that you really do know what you're doing.
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So it sounds like there were some real problems that required some adjusting.
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Do you want to talk us through what that looked like a little bit?
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You know, I'm young.
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And this is like the first real business one too.
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I have investors now.
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And I think everybody suffers with a little bit of imposter syndrome.
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And the longer I've been in business and the more I've talked with people that are really successful, it's almost shocking to hear people that you look up to say, Oh yeah, I deal with the same thing.
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Like I'm such an imposter.
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And I still would say I struggle with that, which I don't think is a bad thing.
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I think it will constantly be pushing me.
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Which is so funny because Kurt, to hear him talk about you're like the most amazing CEO.
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So it's funny that even you still deal with imposter syndrome.
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That's a lesson for listeners, I think, that everybody will deal with that.
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And there's a way to kind of keep moving.
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It's a real thing.
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And I think I'm getting to a point now where I just want to use that to my advantage.
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But you hear as you grow that you want to hire people smarter than you.
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And I have zero problems with hiring people smarter
Dealing with Problematic Executive Hires
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I love to get people in there and let them go.
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And not only does that make them feel empowered, but it also gives me freedom to go and do what I'm really good at.
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So I made my very first executive hire and it was one uber nerve wracking, you know, because suddenly you're paying a lot more for somebody.
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But also I was like so excited to have somebody that was passionate that I felt was really smart at the time that was kind of grasping the business that had more of a leadership brain than the people that I was currently surrounded by.
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So in the beginning, it all was very exciting and it was a fun, cool, new thing.
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Things started to get a little dicey, I think, when I started to realize that this person wanted more than just to be an executive employee.
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It was almost like they wanted so badly to be the CEO of RAG's.
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Where I knew that would be detrimental to the company.
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And Kurt, what was your perspective on this?
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I could tell from the very first meeting that that dynamic was developing.
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And the way it evidenced itself is we, as Rachel mentioned, we went down to Rags' offices to hear about the company for the first time.
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There were several of us from the Kickstart team.
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The two people there were Rachel and this executive that she had recently hired.
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Throughout the course of the entire time together, I would say he took 90% of the airtime.
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And Rachel was really only allowed to comment from time to time.
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And the impression I walked away with as we left was that this person was either the CEO or Rachel intended that the person would be the CEO because there was almost no other conclusion we could draw by the dynamic we saw in that meeting.
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When Kurt talks about it, it's laughable.
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It is... Does your blood boil a little bit?
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It's almost like I think I just have no ego almost to a fault.
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It's like, oh, well, if that makes you feel important, and if that's what you need to feel important, go for it.
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At the end of the day, I know where my value is.
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Here's what's challenging about that, though, Rachel.
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We invest in founders.
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businesses, when we invest, are small.
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Most of the best days are yet to come.
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And so I'm looking, and I think this is true of every investor, really looking for those signals that say, is this a person I want to back?
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We came to the meeting wanting to make that assessment about you, and we didn't get it.
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I also think that that was a lesson learned in that as the entrepreneur and no pressure entrepreneur, but it's true.
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It's like you, you know, especially in the stage that we're in, you really are investing in the leader of the company.
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And I also think shame on me because that should have been very obvious to this executive.
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You know, he should have understood that as well.
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They're here to hear from the founder and the visionary.
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And if I could note, I think it was obvious to that executive.
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The reality is he had motivations about his own role in the company and where he wanted that to go that became pretty clear at that point in time.
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And it was, I don't think that was lost on him exactly what he was doing.
00:15:03
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I think you're exactly right.
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I think at the end of the day, it all stems from just immense insecurity.
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Like Kurt said, he was helping me with the pitch to an extent where Kurt and Kickstart thought, oh, well, maybe this is a CEO.
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To when we got to the end, when we wanted to fund everything, it was like, no, no, no, don't do that.
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And it was almost because he was afraid that it was so transparent.
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That it would be uncovered.
00:15:25
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That it would be, yes.
00:15:28
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That's how I felt.
00:15:29
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So Kurt, how did you, so you invest in founders and you were already excited based on, you know, the reference of Jeremy about this company.
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How did you get to know Rachel as a founder and be excited about her?
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Did that inhibit your willingness to invest for a little bit or?
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No, it just meant we were that much more determined to have the conversations in a forum and a format where we could get to know Rachel and not have somebody trying to play the role of a go-between.
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So it didn't create problems from that standpoint.
00:15:58
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But what it did do, which I think was really helpful, is that in the process of then getting to know Rachel before we invested, the reservations that we felt started to come out in Rachel as well.
00:16:09
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So before we even closed the financing round, we were already having conversations about this developing problem with this one individual and how the company might have to deal with it.
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And that also was really good for me to go through prior to taking on the money because of what I mentioned earlier.
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I wanted somebody that I could call that would help that would actually be useful.
00:16:33
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And it wasn't just a bank.
00:16:35
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I was craving that mentorship.
00:16:38
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And it was nice to go through that in the beginning because I could tell that Kickstart really could be that for me.
00:16:43
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And that was like the missing thing, the missing link.
00:16:46
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Kurt, those are tricky conversations to have, especially as before you funded.
00:16:51
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As an investor, how do you navigate that situation?
00:16:53
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Well, there are circumstances where a company in a similar situation with a problematic senior executive would be a deal killer for us.
00:17:04
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In this case, because we believed so much in Rachel and because we had tested the waters, I think, with each other in our conversations about this individual, I knew we were aligned about what needed to happen.
00:17:18
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And so we were signing up for a difficult piece of work together right out of the gates.
00:17:25
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But since I knew we both knew what needed to happen, we were ready to go do that together.
00:17:31
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It was like scary for me because I was thinking this could totally blow the deal.
00:17:35
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But at the end of the day, I care the most about rags.
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And I know what's best for rags.
00:17:41
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I think investors could see, hey, she'll do whatever it takes for rags.
Significance of Executive Hiring Decisions
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And even at the chance of losing our investment.
00:17:47
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That really was where it got to.
00:17:50
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So tell us what happened.
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But, you know... Let me get the popcorn out.
00:18:00
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We ended up parting ways.
00:18:01
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And I'm such a fan of just being able to part on good terms.
00:18:06
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And I feel like that as harsh and as hard as that was, I remember sitting across the table just crying.
00:18:18
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I got the business to where it was and I learned to believe in myself.
00:18:25
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And Rachel, you are important in the business and you're important and you understand where it should go.
00:18:33
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One lesson that I relearned in watching Rachel go through this is for a CEO,
00:18:43
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there is nothing more transformational than a great hire in an executive role.
00:18:50
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Also for a CEO, there is nothing more catastrophic than a bad hire in an executive role.
00:18:58
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And oftentimes, people that are challenging when they're in the job will also be challenging going out the door.
00:19:06
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And I think we found that to be the case here.
00:19:10
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It shouldn't have to be difficult to part ways when it's not working.
00:19:14
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In this case, it was incredibly difficult just to get the process completed.
00:19:20
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And it wasn't because Rachel wasn't earnest and attentive and working to make it happen.
00:19:26
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It's you have to have a party on the other end that's also cooperative and understands why it needs to happen.
00:19:32
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In this case, it was one of the hardest processes of terminating an employment relationship that I've ever witnessed or have gone through myself.
00:19:42
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I think it is so tempting, especially in a startup when you're resource starved and every person is wearing three hats.
00:19:50
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And in Rachel's case, more than that, to just want to get a position filled.
00:19:55
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And you see a good resume, you see somebody who's got some experience, they present well, they're polished, they're articulate.
00:20:03
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It's very tempting to say, when can you start?
00:20:07
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I'm not in this case suggesting that Rachel didn't do her due diligence, but I think the best CEO recruiters, if you want to call it that, are people who spend an inordinate amount of time in the decision process before they actually make that decision.
00:20:25
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I'm watching right now one of my companies that has to hire a CFO, and the timing of this is absolutely essential.
00:20:32
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They're about to go through a very, very large fundraise.
00:20:35
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They need the CFO, and the CEO is going to take whatever time it takes.
00:20:40
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And it might be months, but the quality of the candidates, the quality of the process, the certainty with which and confidence with which you make that hire, if you do all the homework up front, is significantly better.
00:20:55
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And then would you kind of go with the adage of you hire slowly, but fire quickly?
00:20:59
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Yes, without question.
00:21:02
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Yeah, because I was about, I want, I would love to know, like, how much time do you think you should give for adjustment and onboarding and that stuff before you make that call?
00:21:09
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I will say I've had to do, unfortunately, a fair amount of firing in my career as well.
00:21:14
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There is not a single time where I, in retrospect, believe I did it too quickly.
00:21:21
Speaker
Most of the time when it's not going well, you know.
00:21:25
Speaker
And as soon as you know, make the change.
00:21:29
Speaker
Bad hires don't age like wine and cheese.
00:21:33
Speaker
They only get worse.
00:21:36
Speaker
And the amount of damage that can be caused until that change is made can be very challenging to recover
Mental Self-Care for Leaders
00:21:43
Speaker
And so I think when it's evident, you do it.
00:21:48
Speaker
I think it's so much harder said than done because of imposter syndrome.
00:21:55
Speaker
You know, it's like, am I conflicted with your ability to trust your gut?
00:21:58
Speaker
And like, when you get that conflicting with each other, how do you know which voice to listen to?
00:22:03
Speaker
I think Kurt makes a good point, you know, where it's like, when you're feeling that there is an issue, almost never is it going to go away.
00:22:12
Speaker
Don't wait until it gets so bad that it's destroyed your business.
00:22:16
Speaker
So it's kind of like pain now or pain later, right?
00:22:18
Speaker
Like pick when you want your pain.
00:22:19
Speaker
And that is painful.
00:22:22
Speaker
In this case, the beauty of the relationship that we had established as we were investing in the company and we got to know each other is Rachel didn't have to go through this alone.
00:22:32
Speaker
As she was feeling these doubts, she could immediately place the phone call.
00:22:36
Speaker
And to the extent she was feeling imposter syndrome, at least she had somebody else who's been through the battle multiple times and could say, yeah, you're right.
00:22:46
Speaker
This is a problem.
00:22:46
Speaker
You are not misreading this.
00:22:48
Speaker
That would not have happened with Shark Tank.
00:22:50
Speaker
No, that is absolutely what I was craving and needing.
00:22:53
Speaker
And that is the role that Kickstart and Jeremy had played.
00:22:59
Speaker
So this has been an amazing discussion.
00:23:01
Speaker
And I think the biggest takeaways for me are, Rachel, as you pointed out, trust your gut.
00:23:06
Speaker
And then Kurt, hire slowly, fire quickly.
00:23:10
Speaker
And so Rachel, just to wrap it up, I have one final question for you.
00:23:13
Speaker
And that is, what is the single most effective practice that you've implemented that has had the biggest impact on your success?
00:23:20
Speaker
taking care of myself mentally.
00:23:23
Speaker
Because if your cup is empty, how do you expect to fill anybody else's cup as a leader?
00:23:28
Speaker
As a mom, as a friend, as anything.
00:23:32
Speaker
And you and I went through, I remember this clearly, you're going to remember it as well.
00:23:36
Speaker
We went through an experience literally in January.
00:23:42
Speaker
where we were at a conference together and we left the conference for what we thought was going to be 20 minutes to a half hour to sit down and chat at a coffee shop across the street.
00:23:53
Speaker
It turned into two hours and your cup was empty.
00:24:01
Speaker
I mean, massive lesson learned was quality of life trumps all.
00:24:10
Speaker
I love my business.
00:24:12
Speaker
I am passionate about it.
00:24:14
Speaker
But there was something missing.
00:24:16
Speaker
And I think it was, I wasn't fully taking care of myself and my mental health.
00:24:22
Speaker
And that still is a struggle.
00:24:23
Speaker
And I think for any CEO that will be, it's like you become so fixated that at some point you risk burnout.
00:24:31
Speaker
And it's like, that would be probably the biggest thing that's helped me be successful in life.
00:24:38
Speaker
It's not selfish to take care of yourself.
Choosing Supportive Investors
00:24:40
Speaker
It's actually like, so that you can be a good leader, so that you can be a good CEO, so that you can be a good mom in my case, so that you can be a good partner, so you can be a good friend.
00:24:49
Speaker
And what little steps have you tried to kind of implement to make sure that that's happening moving forward?
00:24:54
Speaker
Hire the right freaking team.
00:25:00
Speaker
That is the honest truth though.
00:25:02
Speaker
Higher right so that you can have that.
00:25:05
Speaker
Kurt, any last words?
00:25:07
Speaker
No, I just, I remember when Rachel and I had that moment back in January, the conclusion I took away from it is Rachel was really asking for it to be okay to be spent and exhausted and to have an honest conversation about what do we do now?
00:25:29
Speaker
And those conversations will happen at various times.
00:25:33
Speaker
Every founder will go through the highest of the highs and the lowest of the lows.
00:25:37
Speaker
And I think one of the benefits I think that Rachel has commented on about having some partners at the table is that load can be shared.
00:25:46
Speaker
You don't have to go through it alone.
00:25:48
Speaker
I love, I just read a stat recently about 72 or 73% of all founders at any given point are experiencing some sort of mental exhaustion and fatigue and need help.
00:25:58
Speaker
And that is freaking isolating.
00:26:01
Speaker
That is so isolating.
00:26:02
Speaker
And so it's kind of to Kurt's point.
00:26:04
Speaker
And most, maybe people would be like, don't do that to your investor.
00:26:08
Speaker
Like they're going to lose faith in you.
00:26:10
Speaker
They're going to be like, whoa, this chick is off the rails.
00:26:13
Speaker
But then again, to Kurt's point, we're investing in people, right?
00:26:16
Speaker
And that means you care about the whole person.
00:26:18
Speaker
And I guess that's the biggest benefit with the partners that I've chosen in Kickstart and in Kurt is I have never felt like I couldn't be authentic.
00:26:28
Speaker
That probably is such a no-no.
00:26:30
Speaker
But the really refreshing thing for me is that I know at any moment I can knock on Kurt's door and be like, hey, I am at that point.
00:26:38
Speaker
Even just saying that and being allowed to say that has been game changer.
00:26:43
Speaker
Which is another great takeaway for all the listeners too.
00:26:46
Speaker
Choose your investors wisely.
00:26:49
Speaker
Hire slowly, fire quickly, pick great investors and trust your gut.
Conclusion and Call to Action
00:26:54
Speaker
Thank you both so much for being here.
00:26:55
Speaker
Thank you, Rachel, for being our founder guest on the episode today.
00:26:59
Speaker
And thank you, Kurt, again, for always being our expert voice on this podcast.
00:27:03
Speaker
I really enjoyed the discussion.
00:27:07
Speaker
So happy to be here.
00:27:09
Speaker
for listening as we dive deep into what it takes to create the perfect pitch.
00:27:12
Speaker
If you want to learn more about our investor, Kurt Roberts from Kickstart or our CEO, Rachel Nilsen, and what she and her incredible team are doing at Rags to continue making Rags so obsession worthy, we'll have a link to the company and a longer bio in our show notes at kickstartfund.com slash perfect pitch.
00:27:29
Speaker
We'll be back next time with more insights from entrepreneurs and the investors who fund them.
00:27:34
Speaker
So be sure to subscribe so you don't miss a thing.
00:27:36
Speaker
You can listen to more episodes of Perfect Pitch wherever you listen to your podcast, Apple, Spotify, Stitcher, wherever.
00:27:43
Speaker
And if you've liked what you're learning, leave us a review or a rating.
00:27:46
Speaker
We'll catch you next time.