Preview Mode Links will not work in preview mode

The Blogger Genius Podcast with Jillian Leslie

Jan 9, 2019

The tables are turned in this episode. Paula Rollo, community manager of MiloTree and founder of Beauty Through Imperfection, is interviewing me!

I this episode we talk about my background as a blogger and entrepreneur, how I stepped away from a career in Hollywood when my daughter was born, what it's like working with my husband, and why I try to embrace failure as much as possible!

Please reach out and let me know what you think. I hope you like it!



Catch My Party

Beauty Through Imperfection





Host 0:03
Welcome to the Blogger Genius Podcast, brought to you by MiloTree. Here's your host, Jillian Leslie.

Jillian Leslie 0:11
Hey guys, welcome back to the show. I am approaching my one year anniversary of doing the podcast and so this week, what I decided to do was to have Paula Rollo (who is our community manager at MiloTree and my very good friend) interview me and ask me all the questions that she's been wanting to know, and maybe you guys have, too.

So I think you'll like this. It was really fun to do. I love this podcast, I am super committed. And so here we go.

Paula, welcome back to the show. This is really exciting for me because this is signaling the end of my first year as a podcaster. And all of a sudden now that the the seats are switched and you get to interview me and ask me anything that you want, so I don't know, I'm excited and nervous to get started.

Paula Rollo 0:42

I'm excited too. It's like pulling back the curtain, you know?

Jillian Leslie 1:06

Paula Rollo 1:06
You know? And seeing like all the magic that happens behind the scenes. And I'm excited for everybody listening, because I feel like I have this inside track to Jillian, that like we talk about things all the time and like I'm always talking to your brilliant mind.

But on Blogger Genius, we only get you talking to other brilliant minds and little tiny glimpses of your genius shining through sometimes. But I think this is just going to be a treat for everybody to get to hear the real you and how brilliant you are at this.

Jillian Leslie 1:37
Oh, thank you. Thank you. Okay.

Paula Rollo 1:43
So, are we ready?

Jillian Leslie 1:44
I'm ready.

Jillian Leslie's background as an entrepreneur and blogger

Paula Rollo 1:45
Okay, so I want to start with your background and your entrepreneurial journey. I know in various podcasts we've heard that you have a business degree and you used to be a writer in Hollywood, which is so cool.

But I want to know how you pictured your life as a kid or as a teen, whenever you started saying like, "This is what I want my life to be." And then you've changed careers, you've gone from working for someone else to owning your own business.

So how did you go about building a life that you loved, and how did that morphing change as you have grown up?

Jillian Leslie 2:22
Wow, okay. When I was younger, I always wanted to be creative and I always wanted to be entrepreneurial -- and I didn't know what that meant. But I had this feeling that I didn't want to work for other people.

But again, like, you know, it was all just kind of mushy. And I would say that there are always these two parts of me and they're not in conflict as much as they kind of like, as you know me, you kind of know these two sides.

One, I am incredibly analytical. I love numbers. You know, I love digging in. And I love research. I nerd out in so many ways in my own free time. And I am incredibly creative, and being creative really feeds my soul that if I weren't creating every day, in some capacity, a part of me would die inside.

So I've gone back and forth in both of those areas like going deep in one and then deep in the other. So when I was younger, all I did was dance and draw and write and do things like that. And then as I got into high school, for example, I got really academic because it was what was demanded of me.

And I went to college, I went to Stanford, and I was really academic. That's what I cared about. Because somehow I knew that my goal was I wanted to be financially independent. And again, I didn't know what any of this meant, but it was like that was the way to do it.

So I did that, and I got out of college, and I got a business job at Disney working in their strategic planning department, which was this organization that was making all these big decisions for Disney. And it seemed cool, and I hated it.

Working at Disney and hating it

Paula Rollo 4:11
Oh, my gosh! How did you hate working for Disney?

Jillian Leslie 4:14
Isn't that weird? It was so funny because I'd call people up from my job and I'd be like, "Hey, this is Jillian Tohber calling from The Walt Disney Company." And people would say to me, "Oh, my God, you work at Disney! You must be so happy, you must love it." And I'd go, "Oh, my God, I totally do."

And I'd get off the phone with them and my day would be so crappy that I would just be crying at my desk. So it was this weird disconnect. And I thought to myself if this is what work life is like, I am really unhappy.

And I felt like they rented my brain Monday through Friday, and anybody who was kind of smart could do this job, but it had nothing to do with me. It was so inauthentically Jill. So I said I need to find another job.

And I ended up getting a job working for Bette Midler. She had a production company on the Disney lots. Because I thought to myself, "I need to be creative. This is the least creative job ever. I need to go that way."

I started working for her and I kept always in life looking to people and going who has the better job and who has the more casual clothing. That was always the way that I thought about it. I'm working for Bette Midler and, by the way, I was like, a scrub, I was getting coffee, I was making copies. I was that person.

But the writers would come in, they would be in jeans. And everybody would listen to the writer and I'd be like, "Ooh, that looks cool." Like, maybe I could do that. But kind of as an aside, I had gotten into business school during this time.

I had applied and I had even deferred it for a year because I was like, "Hey, I'm working for Bette Midler. Sorry, guys." But ultimately, I decided, you know what -- because again, I have these two sides to myself that I would go to business school. I went back to Stanford and I got my MBA.

And by the way, I loved it. Because I went back to Stanford and it was very different than the first time I was there because I just kind of thought, "I'm going to do something creative." So I don't really have to care that much about like my classes. I did things like I took directing and improv and acting and all these.

Becoming a writer in Hollywood

I was like the weird business school student. Yeah. When I got out, I was like, "Okay, I know you guys really like business but I'm going to go to Hollywood and become a writer."

And I did. I went to Hollywood. By the way, I lived in my crappy apartment. All my friends were getting these really big jobs and I was really struggling and writing scripts. And yet then I ended up like getting back working at Disney as a writer and it was really cool.

And as a writer, I was like my own little business person because it was like my own career and I was navigating my own career. And then as I shared previously, I had my daughter, and that changed everything for me.

And all of a sudden, I said to my husband David, "I want to take my fate more into my own hands, into our own hands and let's start a company." My husband at the time was working at MySpace. He was like a senior person at MySpace.

How we built Catch My Party

And we started Catch My Party. And I think I've shared this previously. It was a sight for teen girls because that was how we conceived of it, because all my husband was doing was, you know, who was on MySpace. Teens, teen girls.

Paula Rollo 7:38
Right. That's the audience you knew, yeah.

Jillian Leslie 7:40
That was it. And I was writing teen comedies. So it was like, we own this space, this is it. We get our audience. And, lo and behold, teen girls did not care about Catch My Party. They didn't want to share their party photos. But moms did.

Paula Rollo 7:57

Jillian Leslie 7:58
That was like our first moment of saying, "Whoa! Wait a second. We had this all planned out and it didn't work." But we found another audience to serve.

Paula Rollo 8:09

Jillian Leslie 8:10
And that was how it evolved. So I'd love to say that this was all planned, and that it has this great linear path, but it doesn't. And then now we have MiloTree on top of this and the podcast. And what I would say is, they've all been what I like to call "emergent", meaning they are authentic to where I am in my life.

And they don't necessarily make sense in terms of just like if I had a plan, "Oh, this would be the next piece." No, not at all. But they've all been organic and I always am listening to what I feel is the right next step, and what people are kind of informing me is the right next step.

Paula Rollo 9:01
That's so interesting. I think you brought like a second piece to the average, normal advice that you hear because people always say I guess like when you when you're graduating high school, they're always like, "Go towards what you love and you'll never work a day in your life."

And like "Follow your dreams, follow your heart, just do what you love." For entrepreneurs, that stream of advice doesn't stop, right? That's always what we're hearing and we're always trying to get to this special day where it doesn't feel like we're working.

Jillian Leslie 9:33

Paula Rollo 9:33
Then those of us who are actually entrepreneurs are like, "No, that doesn't happen. I do stuff I don't like all the time."

Jillian Leslie 9:40
All the time.

Paula Rollo 9:41
Because your business is you and you have to do those things, and that has to happen. But I think that what I hear you saying is that you identify things that you love to do and that are life-giving, and those set your direction so you're always headed in a direction you love.

Sometimes you have have to do things that you have to grit your teeth through. But because it's on the way to a direction that you adore, that's okay, and and you're willing to grit your teeth. And that doesn't make it fun to do the little jobs that are just menial and that are not fun you know your direction is you.

Like starting MiloTree, starting a new business is not fun, but going towards something that's organic and that's creative and that has all of these strategic numbers, that makes sense for you.

How being an entrepreneur challenges you

Jillian Leslie 10:26
Absolutely. What I would say is being an entrepreneur looks so cool on the outside and it is so challenging on the inside.

Paula Rollo 10:39
For sure.

Jillian Leslie 10:40
It will challenge you though on a whole host of levels. It will challenge you in terms of one, that you have to work when you don't want to work, and you have to do crappy stuff. And you don't have a boss necessarily, so all of that motivation has to somehow be intrinsic. And that can be a struggle.

It will challenge you in how you see yourself and it will question everything about you. But for me, it's also like the most satisfying path I could ever choose. And it's very humbling.

Because we talk about this all the time. You can think you're really smart and you can think you have a brilliant idea. Then you start working on it, and you start hitting walls, and it can be so demoralizing.

Entrepreneur depression, what is it?

You know, there's something I read a lot about other entrepreneurs and I read about entrepreneurs at these huge companies raising all these rounds of money. And I don't know if people know about this, but there's something called like "entrepreneur depression."

Paula Rollo 11:46
No, I don't know about it.

Jillian Leslie 11:47
And I would have thought, "No, no, these people..." Like, "Oh, my God, I just raised $60 million," like, I should be on top of the world. And there's a real thing where entrepreneurs hit these walls and get really depressed.

And, again, I thank God we have not raised $60 million but there are times where I'm like, "Oh, my God, why did we set out on this path?" I mean not every day is puppies and rainbows And in fact, there are times where it's really cool. Like, you get to speak at stuff or people come to you for advice or they email you how much they love what you're doing.

But that's like such a small piece of it. It has to be some place inside that is feeling satisfied by what you're doing day in and day out.

Paula Rollo 12:41
Yes. I think one of the things that like -- not to try to psychologize all entrepreneurs, but I think that, at least for you and I both, one of the things that has helped with the entrepreneurial depression, and maybe avoiding that a little bit is that we've never made our business define our life.

How not to let your business define your life

Jillian Leslie 13:02

Paula Rollo 13:04
We have our business, like we have this entrepreneurial thing that we're doing, and that's wonderful. And we love it most of the time. And then we also turn it off and we have our life over here. We have our kids, we have our family, and we have those two separate things.

So thinking about that from that perspective, I would think kind of helps you prevent that depression and prevent that burnout. Because it's not my identity, it does not rise and fall on my business. My identity is over here with my family with things that I love to do outside of making money.

And so there's less stress of like, "Well, I raised $60 million, but next year, I've got to raise$ 70 or I'm a failure." But that doesn't matter. My failure or success is not just my business.

Jillian Leslie 13:47
I would totally agree. You know, it's funny, because so many people were like, "Wait, you were a writer in Hollywood?" and I go, "Yeah, I really was." And they go, "How could you have ever left it? It's so glamorous!"

And I said because my whole worldview shifted and it was no longer as satisfying for me. I always have gone toward what feels right. I mean, I try to make very informed decisions, but I'm willing to jump.

It's funny because David, my husband, who's also my partner, is much more grounded than I am, which is great because he kind of holds us down on the earth. But I'm the one who says, "Let's do it. Let's go. Let's do it."

I would say that that's probably one of my best skills, is I'm willing to jump into the unknown with, again, with preparation, but you can't ever fully prepare.

Paula Rollo 14:45
Right. You can't know for sure what's going to catch you because things change so quickly. Especially in our industry, things change so quickly.

Making micro adjustments in your career

Jillian Leslie 14:52
Oh, my God, all the time. And I believe this. Somebody said this to me when I was in my 20s, and they said life should be about micro adjustments because that way, you don't end up with a midlife crisis.

Paula Rollo 15:04
Oh, interesting.

Jillian Leslie 15:05
And I have lived by that, which is, "You know what? This isn't fitting me anymore, so I'm going to go this way." Then I'll see how that feels and if it doesn't work out, guess what, I can always course correct. So I'm a big believer in course correcting.

Paula Rollo 15:19
Right. Just don't do something that can't be changed later and then you can go forward a lot easier.

Jillian Leslie 15:25
Exactly, exactly. Like don't get yourself into a lot of debt or... I don't know. But just kind of making those smart choices but then be willing to say, "I'll try it. And if it sucks, I can change."

So we just recently, as you know, moved to Austin and the way that I could do -- and by the way, we have no family in Austin. We barely knew anybody in Austin but we liked it, and we're like, "Let's do it!" And my daughter was like, "What are we doing?" And I said if we hate it, we can always move back.

And again, that would have been a big deal, you know, but something about it made us braver and that we can do it. And guess what? We're loving it. I'm so happy we did this.

Paula Rollo 16:10
I love that. I love that. Welcome to Texas.

Jillian Leslie 16:13
I like Texas,


Paula Rollo 16:17
Yes, y'all. I end up saying 'y'all' on so many interviews and in professional settings because it's just the word I've grown up with and I get laughed out a lot for that.

Jillian Leslie 16:28
I think it's like the cutest, sweetest word ever.

Paula Rollo 16:32
It's just our word. I don't even have a Texas accent but I do say y'all."

Jillian Leslie 16:37
I love it. I love it.

Paula Rollo 16:38
But in light of these shifts and these leaps, I want to ask kind of two questions at one time -- and that is, what has been your biggest business success and then what has been your biggest life success? And I'm asking them that way because like we just talked about, it's not the same.

You have these two sides to yourself and keeping those things in view I think is really important, and really encouraging to those entrepreneurs listening that if you haven't reached your business success yet, remember all of your life successes like "this baby I have" or "this house I bought" or those things because it's not just your business. And that's life.

My biggest life success

Jillian Leslie 17:21
My biggest life success is my little family. It is my husband and my daughter and our extended family as well. But we are this really fun threesome and there is nothing I like better than spending time with them.

And it is weird because again, I work with David, so we're together all the time. But there's nobody that makes me laugh more than he does.

Paula Rollo 17:49
Aww. Love it.

Jillian Leslie 17:52
So, by far, what has given me purpose is definitely having my daughter, and I would say my husband feels the exact same way. Again, people can't believe that we work together. Because they're like, "I would die if I had to work with my husband." But we met working together during the dot com bubble.

And so we bonded over work and so I knew exactly what he was like to work with. And there's nobody I think that's smarter or more committed or engaged than he is. So that made perfect sense for us. But I feel like our biggest creation, our best creation is our daughter who's just so fun and awesome.

Which by the way, does not mean that she can't be a huge pain in the butt, and that it hasn't been difficult at times. It is. Parenting is one of those things where I always say this, like the least sexy thing you could ever do is have a child.

Paula Rollo 18:52

Jillian Leslie 18:53
But I think it is one of the most meaningful things you could ever do.

Paula Rollo 18:59

Jillian Leslie 19:03
It brings natural happiness to your life -- it can. But it also can bring a lot of pain, but I think it does bring meaning.

Paula Rollo 19:14
Yeah, yeah. It doesn't magically fix things, the problems that are there.

Jillian Leslie 19:20
No. And it can make a lot of things worse.

Paula Rollo 19:22
Right. It makes everything deeper.

Jillian Leslie 19:26
That's a great word.

Paula Rollo 19:26
Pain is deeper, love is deeper, happiness is deeper... all of it.

Jillian Leslie 19:30
Exactly. When I compare that to, say, my businesses which are like babies, we talk about this, I am so happy to have them because they are outside of... I mean, they are kind of part of my family because I work with David but they are also separate.

There's something that I'm building, they're very personal to me. I would say that those are also a big success and are like a big satisfying piece of my life. But having both does balance me.

And that I am not one who just wants to be a bazillionaire and who doesn't care about my family. I care about them all so deeply, you know. So I don't know if that answers the question.

Paula Rollo 20:22
It does. So what was your biggest business success?

Jillian Leslie 20:26
I would say that my biggest business success was really making it happen, that we've we've done this and we built now two businesses. I look back and I go, "Oh, my God," you know, we didn't know when we started Catch My Party whether anybody would ever add a party to our site.

And we now have tens of thousands of parties that people add and tons and tons of content and millions of people who come to our site. So I think that when I think back --

Paula Rollo 20:59
Which is crazy.

Jillian Leslie 21:01
What did you say?

Paula Rollo 21:02
That's crazy that that happens, you know.

Jillian Leslie 21:04
Yeah! Like when I think back when we were like... I remember my mom going like, "How do you think you're going to do this? And I was like, "I don't know. The teen girls are going to show up."

Paula Rollo 21:15
They're going to come in droves.

Jillian Leslie 21:17

Paula Rollo 21:18
And then they didn't.

Jillian Leslie 21:19
And then they didn't!

Paula Rollo 21:19
Yeah, it's just incredible.

Jillian Leslie 21:22
So that's what I would say is, when you're in it, it's very difficult to see your successes because you only see what's in front of you and what needs to be done. You think, "Oh, if I only get to this point, then I'll be happy." I fall into that trap as well.

So I do do those things that seem kind of cloying where I do force myself to come up with what I'm grateful for and to continually use that as my narrative. Even if I'm saying "Well, I'm super grateful for X," but in my heart, I'm going "Yeah, but if only I had Y."

Because I do feel like just even putting it out there and making myself go through that exercise is really helpful and loosening the grip of the grasping, of the wanting, of the longing, of the thinking I'm not full or complete.

Paula Rollo 22:16
Yes. I think because entrepreneurs are such dreamers and visionaries, we do get stuck on what could be. And we miss like "I created something out of nothing." And that's amazing.

Jillian Leslie 22:30
I totally agree.

Paula Rollo 22:31
Even if you haven't taken off yet, even if your business is still strong, like there was a website that didn't exist and now it does because of you. There are people that you're speaking to that weren't being talked to now before and now they are because of you. And that's amazing. it's incredible.

I remember one day, like the numbers we throw around, you're like, "Oh, yeah, millions of people come," like it's no big deal. But if you try to picture millions of people in your head, that's insane.

Jillian Leslie 22:57
I know.

When you know you've arrived as a blogger

Paula Rollo 22:58
And if you try to talk to all of those millions of people that you literally talk to every day, you couldn't.

Jillian Leslie 23:03
I know. We were living in LA when we started Catch My Party. And my husband is the biggest realist in the world. I think that our page views hit something like 30,000... our unique visitors, 30,000 unique visitors a month.

And David goes, he goes, "You know, that's the size of, I don't know, some place in LA like Santa Monica or something." And I go, "Oh, my God, that would mean like every single person at Santa Monica has come to our site?

And he goes, "Yeah," and I go kind of like, "We've arrived!" And I remember him go, "No, no. That number, in order to make any money has to get However, many times bigger." I remember being like, "Oh." But I did have that moment of like, "Oh, my God! Everybody in Santa Monica has come to my site?"

Paula Rollo 23:48
Yes. And I think it's important to have those, like we need to have those goals we're ruling but also be like, 30,000 people, like that's such a small number in our industry, right? We're like, 30,000? You can barely get into MediaVine with that.

Jillian Leslie 23:59

Paula Rollo 24:00
But like, 30,000 is crazy.

Jillian Leslie 24:02
Crazy. Pretty crazy. And so I think you're right, which is, you know, we all sit at our computers in our own little worlds and we don't really understand the impact that we have.

Because there are all these people who are coming to our sites who are learning or getting entertained, or whatever it is. And you're right there is that... So I do recommend everybody out there to take those moments and force yourself to be in gratitude, to force yourself even if it feels really icky and uncomfortable.

Paula Rollo 24:32
Yeah, yeah.

Jillian Leslie 24:34
To make that a habit.

Paula Rollo 24:37
It's so encouraging. It's so encouraging to do. Even I remember one time I was really down on myself I think it was after a algorithm switch, so my page views went like cut in half. They probably went from like 300,000 a month to 150 or something like that. And I was like, really kicking myself about it. I felt horrible.

And my husband was like, "Wait, you're at 150,000 people a month? Do you know how many people that is? I talked to like 10 people this month. You talked to 150,000 people this month about something that you care about? That's a pretty big deal."

And I was like, "Oh, right." I'm just thinking of it in terms of like, "Well, Jillian talked to a million and I only got 150,000." And they're not people in my head. They're just a number because I have my avatar in my head and that's it. I'm not thinking about there's 150,000 of my avatar that I get to talk to and that's amazing.

Jillian Leslie 25:30
And touch.

Paula Rollo 25:31
Yes. And change for the better whether it's with a recipe or a craft or whatever it is that you're doing, you're impacting these people or they wouldn't be on your site.

Jillian Leslie 25:40
Exactly, exactly.

Paula Rollo 25:42
So, I love it. I love it. I love our job.

Jillian Leslie 25:45
I do, too. I really do. And by the way, remember I'm always looking for the people in the most casual clothes. I am sitting here in my sweatpants and my sweatshirt. I have not showered and I couldn't be happier.

Paula Rollo 25:59
Same situation.

It's like the entrepreneur dress code.

Jillian Leslie 26:05

Paula Rollo 26:06
Lack of shower -- that's how we roll.

Jillian Leslie 26:08
Yes. And I do that thing, which is really funny, like I compare myself to Steve Jobs, which is I buy the same sweat pants in every color, even the same color, just so I have a uniform.

Paula Rollo 26:21
Yes, I love it. That's hilarious. Okay, so pivoting a little bit from successes, the other thing that you and I I feel like talk about a lot is how our failures are not just necessary or a necessary evil but they're actually a vital part of our business.

Talk about a little bit how specific failures have shaped the way your business looks today and what failures have propelled you into something great.

The need for more "at bats" in your business

Jillian Leslie 26:53
Ooh, okay. The one thing that I would say -- David and I talk about this a lot and we call them "at bats," like you're at bat as a baseball player. That instead of thinking about something as a success or a failure, we think of it as an "at bat" and the goal is to have as many as you possibly can, realistically speaking.

I was reading this article about Nestle. I think this is right but it could be no. But Nestle hit it out of the park, with Nespresso and it grew their business incredibly and they have not had many successes since then. The reason is because they captured lightning in a bottle, it was like the right idea at the right time and it, boom, exploded their business.

But catching lightning in a bottle and betting your whole business so you're going to find another one of those is not a good business strategy.

Paula Rollo 28:01
Oh, that's good.

Jillian Leslie 28:02
So not many things you try are going to work, and somehow recognizing that makes it feel less personal. And I've started to really think that.

So we had this idea recently where with MiloTree, we're way into this, you know, remember we're geeks, so we're into the technology. And what we realized is lots of people were using sites that were not secure, right? We know about HTTPS versus HTTP.

We noticed a lot of our users were not using secured sites. So we decided, "Hey, here's an idea." What we could do is we could help these people get on to I think, we were looking at SiteGround because we really like SiteGround.

That we would help them move their blogs to SiteGround off of, say, Bluehost or something, a site that wasn't secure at the time. And we're like, "Hey," and that could be good for us because we could make affiliate money by doing this and what we would offer is we move your site for you.

So we looked through our data and we found all these people who did not have secured sites and we reached out to. I reached out to maybe 100 of them. And I said, "Hey, here's the deal. Just, you know, your site's not secure. This is not a good thing." I explained why.

"And what we'll do, we believe in this host called SiteGround and will help you do this." And we thought, "Wow, this could be a great income stream for us" and we'd be providing our users a service and, you know, it would be a win-win. Nobody wanted to do it.

Paula Rollo 29:48

Jillian Leslie 29:49
Nobody. In fact, people were a little, I want to say, kind of almost offended. What we realized is that it's kind of risky for somebody to move their site.

Most of us, except for David, are not super technical. And that's like, "What? who are these MiloTree people coming in and saying, "Hey, well, you know, you got this problem and will help you, but why would I trust you?"

Even though, again, they might be using MiloTree. They might know me still. And I noticed, I started to feel bad like, "Oh, wow, that didn't work." And then I thought like what a dumb idea. I started to personalize it. Then what I realized was, "No, no, that was just one at bat."

And by framing it that way, I thought, "Oh, okay. We need to come up with more ideas." So this one didn't work, well, okay, but we're looking. And then what you do is, ultimately, you do find stuff.

It's like, you know, dating. You kind of have to date a bunch of people until you find that right one. And so that's really the frame through which I think David and I have pivoted our thinking about failure. The more failures I have, the better, because that means I'm on my way to finding that thing that will work.

Paula Rollo 31:12
What did you get from that specific example? Were there things that you learned from it that helped you with your next at bat that you framed the next one differently or something from it?

Jillian Leslie 31:25
What I would say is it taught me that that it showed me again, that our customers, they're much more creators than they are interested in the technology. So again, that's something that we're always thinking about.

And so when we build MiloTree, we're always trying to take the technology piece out as much as we possibly can and not focus on our features and all this cool stuff we do. We want to do that in the background so that the creators could go create.

Paula Rollo 32:04
Yes. And in framing it that way means more responses, more purchases.

Jillian Leslie 32:11
Exactly. Like we've got your back. So what we're trying to say in these emails was, "We've got your back." But, ultimately, it was too big of an ask.

Paula Rollo 32:18
Right. You just overwhelmed me with technical jargon. I have no way to check if you're lying to me. I have no way of understanding. And that's ultimately not what I come to MiloTree for either, right? It's shifting in this direction that you're thinking, "Oh, I can help all these people," and these people are thinking like, "I just want you to get me Instagram followers."

Jillian Leslie 32:40
Exactly, exactly. So that's what I would sa,y like how we learned about it and how it has helped inform us. So my husband is a typical guy. He loves the data and he's like, "Maybe we could create a dashboard for people's Google Analytics." And I'm like, "No, I don't think that our users would have any interest in that."

Paula Rollo 33:03
Right. I'm sure some people would but it's not like the next step you need to take because the percentage isn't there.

Jillian Leslie 33:09
Exactly. So it helps us, again, further define who our customer is and that even though we identified the pain point, they didn't perceive it as such.

Don't solve a problem people don't think they have

Paula Rollo 33:21
Yes. That's so important to like, if you solve a problem people don't acknowledge, it doesn't matter that you've solved that problem.

Jillian Leslie 33:29
Exactly. It's like creating, you know, like think about in your own life, I don't know, like do you need a better way to sit down than a chair? You know, a chair is pretty good. So it's like that.

Paula Rollo 33:44
It's like the people who invented the banana slicer? It's like, yes, your product is more efficient. But did I need it?

Jillian Leslie 33:52

Paula Rollo 33:53
And you created something that did work better than a banana slicer and it would have helped, but the way people are looking at it is just like, "No, this could cause me just as many problems as it solves because now I have to wash it, then I have to store it somewhere. They don't understand enough to know that this is actually going to help.

Jillian Leslie 34:12
And typically what I have read is that if you have a new solution to a problem that already has a solution, it has to be 10 times as good for somebody to switch.

Paula Rollo 34:22
So true. We've seen that with every new social media platform that has tried to launch like Ello tried to be a thing and all these other places. And because they're just Facebook but Ello.

Jillian Leslie 34:35
Right, right.

Paula Rollo 34:37
I'm not going to go over there because you only have one new for each feature, two new features, and all my friends aren't there yet. And there's nothing to get me there.

But with Instagram, when Instagram came out, it was new, it was shiny, it was completely different. When Pinterest came out, same thing. It was new, it was shiny, it was completely different. And so people came over because it was 10 times better or different even though at the end of the day it's just social media.

And my same friends who are on Instagram are also on Facebook. And my same friends are on Snapchat and all the other ones. But it's different enough that I'll do it.

Entrepreneur advice: Make sure you're solution is 10x better than the next option

Jillian Leslie 35:08
Absolutely. So think about that. Just if there's a problem that you're trying to solve, how much better is your solution than what's already out there?

Paula Rollo 35:17
That's so good. That's so good. I guess that that can be like a way... a follow-up question is just like how can entrepreneurs look at their failures and so they don't just ball it up and throw it in the trash and forget about it. But what keys do you look for to say, "I'm going to take this small thing from the failure and try my next at bat." Like, how can we not waste those failures?

Jillian Leslie 35:40
Ooh, that's a good question. I think depersonalizing them which is the more you can say, "I'm not a failure," the more you're willing to be curious about why this failed.

And to use that curiosity to say, what does this tell me about my assumptions and does it tell me about my customer, my avatar, and how are they not connecting.

Paula Rollo 36:12

Jillian Leslie 36:14
And then there is always this piece that you won't know. You will make these assumptions but then that's why you need the at bats because you think, "Okay, I'll go this way then" and you try that. And if that doesn't work, okay, what is my next hypothesis?

But the more things you can be testing and trying in the most down and dirty way, the better. So, for example, and don't be afraid to do stuff that doesn't scale.

So in this experiment, to see if we could help people secure their sites, all I did was I said, "David, please send me..." I think I went to our most recent customer, something like that. And I went to every single site and I looked to see if it was secure or not secure.

And if it wasn't secure, I took a screenshot of where it says "not secure" in the browser and then I came up with an email, and then I would email these people with using the screenshot where it says "not secure", and like this was not scalable. But I wanted to see what feedback I got.

Maybe I went through 100 accounts, maybe I sent 25 emails and got almost no responses. I think I got one... No, I don't think I got any positives and I got one kind of nasty email back.

Paula Rollo 37:48

Jillian Leslie 37:50
So that was a very strong signal.

Paula Rollo 37:52
Yes, this is the wrong way.

Jillian Leslie 37:55
This is the wrong way. Don't go this way, go another way. So again, it's like, maybe I spent a couple hours on this but I was in there mining. You know, I've written about this which is you're a miner when you're an entrepreneur, looking to monetize. And again, there's a lot you won't know.

Paula Rollo 38:19
Yes, but it's worth looking at, to see what you can identify.

Jillian Leslie 38:24
And there are times where you go, well, maybe these were the wrong people you reached out to. Maybe if you reached out to the next hundred people. And that's the thing. I don't know. Maybe that's true. So you don't ever really know whether your test was a good test or whatever but you kind of have to make a lot of assumptions and kind of figure out what your next at bat is.

Paula Rollo 38:46
Right. And then from there, see if maybe you need to start back at the first one or not.

Jillian Leslie 38:50
Yes, exactly.

How is your avatar different from you?

Paula Rollo 38:51
I think what's interesting in what you identified from this failure, it sounds like to me, is that, okay, so most entrepreneurs, we have our avatar like this is a common common phrase we know. And for most of us, we are our avatar, right? It comes from, "This is what I know and so that's what I can speak most to."

But I think what's key that you identified there that we don't talk about as much is how your avatar is different than you. And you have this really unique thing where you like numbers, which is very foreign to me, by the way, I hate numbers. If it involves a number, I'm not going to remember.

Like, no, I feel like my brain just rejects it as soon as I hear a number. My brains is like, "No, I don't like it."

Jillian Leslie 39:32
That's funny.

Paula Rollo 39:33
I just like creative and I like strategy. I like charts that have pictures, not charts that have numbers and just that's how I am. But you were able to look at this and say, "Okay, I am my avatar. I'm reaching these entrepreneurs."

But there's this big key way that your avatar is different than you and then finding that is really helpful for your success going forward because next time, you can frame it in a different way that, "oh, maybe they don't like the number but they would like this."

Maybe they don't like this technical jargon but like you're saying, they like hearing how it frees them up to be more creative.

Jillian Leslie 40:08
Exactly, exactly.

Paula Rollo 40:11
With Jillian as my avatar, you would have never realized that.

Jillian Leslie 40:14
No, and in fact, it makes me more empathetic. So what I want to say is you can trust me because I've got David. I like numbers, yes, but I've got this technical powerhouse behind me, and we're trustworthy, that maybe there's a way I could take more of the technical burden off your plate.

Paula Rollo 40:41
Right, exactly. Instead of sending them an email chock full of numbers and nerdiness and geekiness of how this works.

Jillian Leslie 40:49
But also, I think too by sending them an email with a screenshot where it says "not secure with your URL," there's a little bit of shaming that I might have done.

Paula Rollo 40:59

Jillian Leslie 41:01
Like, "Ooh, I don't want to look at that. Why are you doing this?" I think it was not received in the way that I anticipated it was. And again, did I have a moment of shame and ickiness? I totally did. But then I was able to go, "No, no, this is just what you do as you test stuff," and you see.

Paula Rollo 41:24
Right. Well, and it was also where the only thing you lost was your time because it's not like those 25 people went and deleted their MiloTree accounts and demanded refunds because, "how dare you?" They were just like, "I don't see what she's doing."

The one person got mad. But it wasn't something you couldn't take back. It wasn't something that was going to be, like we were saying before, like go ahead, jump out, try it. But make sure it's something that you can just completely retreat on.

Jillian Leslie 41:53
Exactly. Exactly. So that was definitely a really good learning. And I want more at bats. And the hard part too as an entrepreneur is where do you find the time for that, to carve those out. So what we do is we try to, you know, have a list of ideas and go "We need to test these things."

What does Jillian's typical day look like?

Paula Rollo 42:16
That's good. Well, I was just going to say like, in that, what does your typical day look like? How many at bats do you try? How many days? Is it just like, "I have to share on Facebook. I have to pin on Pinterest"?

Jillian Leslie 42:31
Okay, that's a really good question. And I wish I could tell you that my days are more kind of structured and organized. I live with Post-It's and I have Post-It's all over my desk because they're immediate. I've tried all these all these places like Trello.

And I do use Trello but just in terms of what's most immediate, I have like my days set out in Post-It's. And I have really neat handwriting.

Paula Rollo 43:04
I didn't know this about you. This is very interesting.

Jillian Leslie 43:08
Okay. I have like my most important tasks up on Post-It's. What I typically do is, first of all, I drink a lot of green tea during my day because I find it very calming and soothing. But I have different teams.

Jillian's Catch My Party and MiloTree teams

So I've got you as my MiloTree team, so you, David, and me. And then I've got my Catch My Party team, which right now is my assistant, my lovely assistant in Portugal, Ana. And then I have another assistant in the Philippines named Marie who kind of comes in. And I've got different Slack channels. So I've got Catch My Party as my Slack channel, and I've got MiloTree.

And then I also have another group of designers who live in South Africa that we work with a lot. Then I also have some consultants that we work with. We're working right now with Deepak who has been a guest to work on SEO.

So we've worked with ad consultants, or SEO consultants, or different designer consultants. And so I always have some kind of project working. I'm usually working with some outside help.

And I usually then check in in the morning with my teams and see what's going on. Ana does a lot of the heavy lifting for Catch My Party, but together, we are coming up with strategy. We are coming up with blog posts, she's creating them, and then I'm editing them and pushing them out.

What I have found is it's all about the quality of the people you work with. And that if you can find people who you jibe with, who you like to... it's a little bit like, "Hey, how was your day? How was your Thanksgiving?" That kind of thing. Like, I like my team personally and I like them professionally.

Paula Rollo 45:03
That's good.

Jillian Leslie 45:04
And I feel like they've got my back.

Paula Rollo 45:06
Yes, we do.

Jillian Leslie 45:09
Yeah. So therefore it's a little more ad hoc than you would think it would be in that I don't... you know, some people block out days. "Today, I'm going to work on blog posts. Tomorrow, I'm going to work on social." All that stuff. I wish I could be that organized.

But it's typically a little more, "Okay, this week I know I want to do these certain things" Also, all these blog posts are going live. We do three blog posts a week on Catch My Party, I do a podcast episode every week that goes live that has a whole host of stuff that has to happen.

So there are a variety of things that keep kind of moving forward and that in the midst of this, I'm trying to, in the cracks, figure out what the next at-bat is or working with a specialist. Right now we're experimenting with SEO and Pinterest ads -- and those are the two things kind of running in the background.

Paula Rollo 46:05
You've almost transitioned from this one-man show that we all start out as to a manager.

Jillian Leslie 46:12

Paula Rollo 46:12
And having teams of people that work for you and still doing a lot of the legwork yourself because that never goes away. But there's just management aspect that makes your day, it sounds like a little more chaotic.

Jillian Leslie 46:24
It does. And what I found is, the fewer people I have to manage, the better. I've grown my teams bigger and I shrink them down to the bare bones. But what I would say, and we talked about this before we started recording, is like, how do you know when to hire somebody or when not to. That kind of thing.

Advice: How to hire VAs

And what I would say is start with something like Upwork which I use, which is where I can find, or Fiverr something. I've got a task, I need help with this task, I will hire somebody to help me. And if I find a gem, I will then give them another project.

Paula Rollo 47:04

Jillian Leslie 47:05
I don't go, "Oh, I need a VA for everything." Uh-uh. I need a VA to do this task."

Paula Rollo 47:12
Right. And then you scale your VA.

If I like my VA, if we work well together, if my VA is responsive and responsible and kindhearted, then I'll go, "You know what, I've got another project."

So I think in terms of projects. And that way, I don't know, I can budget, I don't know, $100 to try them out and and see how how it works before I'm willing to commit, I don't know, thousands of dollars.

Right. Yeah. And then you can slowly grow that team.

Jillian Leslie 47:44
And then I can pull back. So again, I think of it as emergent more than I think of it as top down.

Paula Rollo 47:55
How did you know it was time to hire your first VA test?

Jillian Leslie 47:59
I was drowning. I was drowning and I was making enough money that I could justify it.

How to know when to hire someone for your business

Paula Rollo 48:06
Okay. What does enough money look like then? I think a lot of people are in this position like "Should I? Shouldn't I?" I think that it does help breaking it down to a project because normally the decision is, "I'm going to hand over all social media forever" and it's going to be like $900 a month.

And that's too much. How do you know that you have enough money and how do you identify that first project when you are drowning, and you have to have time to hand something off?

Jillian Leslie 48:33
Okay, here's what I would say. How much is your time worth? And if in fact, if your time -- and again, I like numbers. So you can figure out how much your time is worth by thinking about how much you make, how many hours you work.

Okay, so I make let's say $20 an hour. If I can hire somebody for less than $20 an hour, it's worth it because I can then use myself in that hour to do something of higher value.

Paula Rollo 49:06
For the first one, it may not even be taking hours off your plate. It may be more changing what you're doing with your hours.

Jillian Leslie 49:14
Yes, yes. If I can move to a higher task, let's say social media. My social media is kind of this rote job, and it's not using all of my brain in terms of my creativity, or my ability to go mining for other opportunities. It's worth it for me to hire that out.

And then I can use my own resources, my own brain for something that could bring in more value. The problem with kind of what we do, is we get on these like hampster wheels, and it's hard to get off of them. And I struggle with this as well, like, "Oh, I'll just go do it."

And then what I realize is, you know, there's three days have gone by and all I'm doing is social media, and I haven't been able to elevate above it, and really do some strategy or reaching out, or whatever other things are that will push my business forward, not just keep me in the same place.

Paula Rollo 50:19
That's so good.

Jillian Leslie 50:21
And again, here's what I would say, for the people I work with, I typically create little training videos.

Paula Rollo 50:30
That's good.

Jillian Leslie 50:32
That I then add to YouTube as non-public or whatever, so that there's a link so that I don't then... let's say I'm going to try somebody out for a project. And this is how I want to do a task like do Facebook posts or something like that. I will make a video and go through step-by-step how I think about it, how I do it, post it so that VA can see that video.

Then let's say I hire this person, and you know what, it doesn't work out in, here's what I would say, too. Cut your losses early. If it's not working at the beginning, it's not going to work at that end. So move on, in a kind way, but find somebody else. And I've already got the training video.

Paula Rollo 51:13
Right. You don't waste "I talked to her for 45 minutes and I hired her the next day."

Jillian Leslie 51:17
Exactly. You already invested. There's this thing called sunk cost which is, you know, let's say you're at a restaurant and they say it's an hour wait, and now you've waited an hour, and they say "oh, it's another hour," or whatever and you go, "I've already waited an hour."

Well, that's gone. Evaluate whether you still want to wait another hour.

So it's like, well, I've already trained her and it's 45 minutes, but it's not wort... you know, you spent all this time already. I've invested all this energy I can't pull up. No, you can pull up. So therefore systematize things in very down and dirty sort of ways.

Paula Rollo 51:57
Yes, because it's not worth the mental load to keep on somebody who's failing.

Advice: Work with people you like. Life is short.

Jillian Leslie 52:03
It is so not worth it. Like work with people you really like. Life is short.

Paula Rollo 52:08
Yes. One of the best benefits of working from home is you don't have that annoying coworker you hate.

Jillian Leslie 52:16

Paula Rollo 52:17
You get to pick your coworkers and you can learn.

Jillian Leslie 52:19
I will share this. We talk about this. I am a huge introvert. And I get enough social interaction just by like chatting with you on Slack. And then I can just go away and just be quiet and not have that co-worker come into my office. So that really works for me.

Paula Rollo 52:37
Yes, you can mute me when you need to.

Jillian Leslie 52:40
Exactly. Exactly. And that's what I would say. So systematize, do things in projects. And I will say this. I think we did this. I don't know if we did this. I think we did. Like let's start with two weeks.

Paula Rollo 52:52
Yeah, we did.

Jillian Leslie 52:53
See how it goes.

Paula Rollo 52:54
We did.

Jillian Leslie 52:55
See if we're both happy.

Paula Rollo 52:56
Yes. And take the mental load off too. Because if it hadn't worked out, it wouldn't feel like, "Oh, Jillian fired me. I'm not going to talk to her again."

Jillian Leslie 53:05
Right, right.

Paula Rollo 53:06
It could have just been like, "Well, it didn't work. My expectations were different than her expectations." And, you know, maybe she's too picky. But I'm not going to feel bad about myself because it was only ever a trial.

Jillian Leslie 53:17
And we can still be friends.

Paula Rollo 53:19
You can do the old breakup, "it's not me, it's you."

Jillian Leslie 53:21
Right. Exactly. So that's what I would say which is, you know, be flexible. I think that as we're talking, the theme that I keep hearing is this idea of being an entrepreneur is all about being flexible. And it's all about not taking things personally, which I struggle with.

Paula Rollo 53:40
Yes. Oh, it's so hard.

Jillian Leslie 53:44
But if there are a couple things that I would say it's more at bats, like really put yourself out there, just try because who cares? And, you know, don't beat yourself up as much as we all like to do and personalize it. The other stuff. And to notice -- notice the stories we tell ourselves because so many of them aren't true.

Paula Rollo 54:09
Yes. I feel like you tell me that every week. This is true Jillian right here, guys.

Jillian Leslie 54:17
Yeah. And I don't know. Like just even I say it to my daughter all the time. She comes up with these elaborate tales of how tomorrow at school is going to be a bad day. And I go, "Wow! What a story."

Paula Rollo 54:29
Right. And it's so helpful to hear that like rational... You're right. This is one possible outcome of an infinite number of possible outcomes.

Jillian Leslie 54:41
Right. And how do you know you're right when that's going to happen.

Paula Rollo 54:43
Why would I pick that one?

Jillian Leslie 54:44
Right. Absolutely, absolutely.

Paula Rollo 54:47
So good. Okay. So as we're ending here, I do want to know this is a year of Blogger Genius, which is amazing. And so I want to know what inspired you to start The Blogger Genius Podcast in the first place and then also what information gap do you feel like it's filling in our industry.

Jillian Leslie 55:08
Ooh, okay. I am a huge podcast listener, so I am my own avatar.

Paula Rollo 55:14

Jillian Leslie 55:17
And I love the intimacy of it. Again, I love to learn. So the idea that by having this platform, I can invite people on and learn from them, and then share it with other people. Like, there could be nothing better for me.

Paula Rollo 55:32
Love it.

Jillian Leslie 55:33
And I haven't done any podcast where it's just me talking and maybe I will get there. But I feel like having a guest and kind of getting to ask the questions that I want to ask, it gives me this excuse to even ask the more personal questions or the question that, you know, you wouldn't necessarily ask at a cocktail party.

Paula Rollo 55:53
Right, yes.

Jillian Leslie 55:56
So weirdly, there's a selfish component to it which is I'm learning along with you.

Paula Rollo 56:00

Jillian Leslie 56:04
And that has been incredibly satisfying. I went to a conference called Podcast Movement. And I had been toying with the idea for a long time. And I took a workshop, a one-day workshop that said you could start a podcast really easily. And I have to say you can, but it's not as easy as I thought it would be.

But I did it. They said that most people quit before their eighth podcast episode. So I made it like a thing that I was going to get past eight, and I loved it from the get-go.

Paula Rollo 56:41
That's so cool.

Jillian Leslie 56:43
And I guess the gap that the hope of what I'm providing -- and please reach out to me and let me know if this is true -- is I'm hoping to shine the light on the hard lessons or what people are doing, or that there is no one right answer. And to hopefully make it not as lonely.

And that you can hear other people's struggles or other people's successes and see what you can then take into your own business. And I hope to be a friendly voice in your ear cheering you on.

Paula Rollo 57:25
Yes, I think you can do that. And I think to connect it with what you were saying too, it almost gives listeners ideas for their next at bat. Like SEO wasn't on my radar and then Deepak gave us a thousand ways to grow in SEO.

Maybe this or that business plan, depending on where people are, they can listen and they can hear from somebody else's at bat and go, "I want to take a crack at that ball. I'm going to try that."

Jillian Leslie 57:52
Absolutely. Then the thing that we always talk about is, just because it's working for somebody doesn't mean it will necessarily work for you. And this has been a hard lesson for me to learn.

Paula Rollo 58:05

Jillian Leslie 58:07
So therefore, hopefully, the guests give a whole host of ideas, and you can see if -- I'll try that in my business. And again, this is the piece that I'm always working on, which is, if it doesn't work, it's not personal to me. It's like when people personalized like, "Oh, Facebook doesn't like me."

Paula Rollo 58:27
I've said that.

Jillian Leslie 58:30
Yeah. But it's like, "Okay, this might not align for my audience or my customers. But I can find something that does align, and I'm going to keep searching."

Paula Rollo 58:41
Yes. Because even somebody else's fail story, there could be somebody listening right now who their audience would have resonated with an email, with a screenshot of your site is not secure, and they could go, "I'm going to send that email to my audience."

And all hundred of their people would say yes, because their audience is different. Or the same happens with somebody sharing this epic success, and then somebody would go, "I'm going to try that" and then it's an epic failure for them because our audiences are different.

But it's helpful to hear what other people are trying and experimenting with, and we can kind of create our experience or our experiments with the benefit of their experience.

Jillian Leslie 59:21
Totally, totally. And I guess the thing is, to know that we're all struggling. We're all in this struggle, but it's okay to be in the struggle. And we all wake up sometimes and go, "Oh, God, I don't want to work today." And then there are days where it's effortless.

And that's the thing that I think is so interesting, is that you show up and it just... who knows what you're going to find?

Paula Rollo 59:53
Right. It just clicks.

Jillian Leslie 59:55
It's a little bit like having children and every day, they're different. Like, some days I turn to my daughter, I go "Who are you today? I don't recognize you."

Paula Rollo 1:00:07
Yes. I had a friend use this analogy for something last night, actually. Se said it was like starting a gas stove, and how you turn the crank and it clicks, and it clicks, and it clicks. And then at one moment, you've just got this flame, and it's on and you've got it. But you had to click it so many times at first.

Jillian Leslie 1:00:25

Paula Rollo 1:00:27
That's how it works. But we just want the flame immediately -- and that's not how a stove works.

Jillian Leslie 1:00:33
Yes, yes. So I would say that if, in fact, you are willing to work hard, you are willing to do crappy stuff, you are willing to be in the unknown, you're willing to face yourself and your own demons, there is nothing better than this job. And chances are, you're not going to get rich tomorrow.

Paula Rollo 1:00:56
No, but your life could be rich tomorrow.

Jillian Leslie 1:01:00
But your life could be rich, yes. It's funny. I will say this one thing, which is, so during the dot com bubble, I was writing television shows. Remember there were hiatuses in television season.

So I was on hiatus and I went to my agents and I said, "There's this thing called the internet, guys. And there are these new internet companies that are doing entertainment content and I want to write a show for one of these companies.

So I don't care about money, I want stock options. Because guys, we're going to get rich." And my agents looked at me like "You're crazy!" And I looked at them like, "You guys are just so... you don't get it."

Well, I went to work at this company. It was called I met David and we started working on a project together, and we really hit it off. Ultimately, the company burned through something like $35 million and went out of business.

And I always say I didn't get rich in the way, I thought I was going to get rich, but I got rich in a whole different way.

Paula Rollo 1:02:16
I love that. And that's the entrepreneur journey right there.

Jillian Leslie 1:02:21
And there it is, there it is. You don't know what's going to show up in front of you, but it could totally change your life.

Paula Rollo 1:02:31
Well, I don't know how we could end a podcast better than that.

Jillian Leslie 1:02:34
Awesome. Well, I have to say, this has been really fun. And thank you to you, Paula, for being my partner -in-crime. and I always call you my best thought partner. And I'm always saying to David "Isn't Paula so smart? Like, look what she came up with."

So I want to just thank you and let you know how much I appreciate you and all that you do.

Paula Rollo 1:02:58
I appreciate you and being on this team, it's a lot of fun.

Jillian Leslie 1:03:02
And also I want to say thank you to my audience for showing up every week and listening to me and please reach out to me, let me know what you like, what you don't like -- I won't take it personally, maybe a little bit. but still, please do it. And let me know what you want to hear for the show. And just thank you for coming along on the journey.

Get MiloTree to grow YouTube and Instagram and Pinterest and Facebook and your email list and remember, get your first 30 days free. I welcome you to join the family.

Sign up for MiloTree now and get your first 30 DAYS FREE!