How to go From $200 to $16K in 3 months with Kelsey Kerslake

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The feast and the famine are two staples in running your business, right? It’s doesn’t have to be! That’s the message from Kelsey Kerslake, who went from $200 to $16,000 in her bank account in 3 months! Kelsey shares her story, tips, and what you need to do to grow your business and avoid that feast and famine stress.

Show Notes


Joe Casabona: Hey, everybody. Real quick before we get started, I want to tell you about the Creator Crew. If you want ad free extended episodes of this podcast in the form of a podcast called Build Something More, as well as access to a community, live streams, bonus episodes, and deals, check out and sign up for just $5 a month. You’ll get a bunch of great content and you get to support the show directly.

Today on Build Something More, I talked to Kelsey about what it was like working in the stationery field—I’m a huge stationery nerd—and then we talk about what it’s like being business owners and parents in the time of a pandemic. So it’s a really good conversation. We went over time a little bit, but I think you’ll really enjoy it. Again, that is You can sign up for $5 a month or $50 a year. And everybody who signs up gets an exclusive membership. That’s a customized poker chip to show that you are a member of the show. Head over to today.

Hey, everybody, and welcome to Episode 220 of How I Built It, the podcast that offers actionable tech advice to small business owners. I’m trying on that new tagline. It used to be the podcast that asks: how did you build it? But we’re shifting a little bit. We want actionable advice for people who are actively building things.

Anyway, my name is Joe Casabona, I’m your host. Our sponsors for this week are TextExpander, Restrict Content Pro, and The Events Calendar. You’ll hear about them later. But first, I want to bring on our guest for this week. Her name is Kelsey Kerslake. She is the CEO of Pinegate Road, and The Aligned Business. And we’re going to be talking about how she went from zero to hero, how she went from $200 to $16,000 in three months. I’m excited to tell her story. Kelsey, how are you today?

Kelsey Kerslake: I am Great. Thank you so much for having me.

Joe Casabona: Thanks so much for coming on the show. When I saw this topic I thought it was great. I know that a lot of small business owners now, as we record this, we’re still in a pandemic, they’re trying to think of unique and creative ways to grow and pivot and how to optimize their business. I am one of those people. So this will be as much for me as it is for the listeners. But before we get into all of that, why don’t you tell us a little bit about who you are and what you do?

Kelsey Kerslake: Yeah. My name is Kelsey Kerslake. I come from a background of graphic design, brand design, brand strategy. I have my BFA and MFA in graphic design. So that has always been my background—the artist. I kind of picked graphic design because I was like, “Oh, it’s going to be on computers. Maybe I can make money one day.” So I always knew I wanted to be artistic, creative, that kind of thing.

I actually started my business while I was in grad school as a lifestyle blog. I was freelancing and doing all this kind of thing on the side. And then I went into corporate America as a stationery designer for American Greetings.

Joe Casabona: Nice.

Kelsey Kerslake: I was doing my hand lettering, all of that kind of stuff. And then I took my business… I’m kind of skipping over the stuff. But I took my business full time in 2016. That is really when I realized, okay, I have to take this business and turn it into something that’s beyond me just doing my passion. I actually have to learn how to run a business. And I really failed that year. I was basically spending money in all the wrong ways, I didn’t understand sales, I didn’t understand marketing. I knew how to do my craft and my skill, but I didn’t actually know the business of running an online business.

So by the end of, you know, it was the summer of 2017 at that point, I’ve been running my business for one year full time and I ended up with $200 in my bank account because I did not know how to run a business. That’s kind of where I ended up after one year on my own. And it was a really rough place to be. So that’s kind of where I think the story begins.

Joe Casabona: I think that is really something a lot of listeners will be able to resonate with. I know this is the case for me. When WordPress became super popular, a lot of listeners are in the WordPress space, a lot of us just kind of thought, “Oh, I’ll just build something for… I’m a developer, I can make plugins or I’m a graphic designer, I can make websites and I’ll just do that stuff for clients.” But we never thought about running the business the right way. So I think that this is going to be lots of great advice for people.

You mentioned stationary—and we can talk about this and Build Something More—but I am a huge fountain pen nerd and stationery nerd.

Kelsey Kerslake: Amazing.

Joe Casabona: My current notebook is from The Well-Appointed Desk. I don’t know if you know Ana Reinert. It’s like this vintage typewriter writing paper. I’ll put a picture in the show notes over at But maybe we could talk about that in Build Something More because I am a giant stationery nerd.

Kelsey Kerslake: Yes, we can go into it.

Joe Casabona: Excellent. But for now, let’s pick up with your story. After a year in business, you had 200 bucks to your name or maybe to your business’s name. How did you turn that around?

Kelsey Kerslake: The first thing I did was I cried in the shower. I was like, “I don’t know how I’m going to pay my rent the next month.” At that point, I was engaged to my husband and we were living together. And he was like, “Kelsey, you’ve reached the end of this experiment where you’re running your own business. It’s time to go find a job.” And I thought my whole dream of running my own business was coming to an end. It sounds dramatic but that was one of the roughest parts of my life, because it was my whole dream to be able to run my own business.

I actually started applying for jobs, and I made it to some top interviews and some pretty big companies. One in particular, I didn’t make it. And that was when I was… I’m not going to share names or anything. But that’s where I was like, “Oh, my gosh, I guess I have to go all in in my business.” So it was almost like my plan B was my actual plan A. And I’m just really thankful for God and the universe for pointing me in this direction. Because even though it was a really low point, it all really worked out. And I’ll kind of share what that looked like.

So for that first, knowing that I had to go all in in my business from that point, it was really how do I get out of this survival mode? I think that when you just need to make the money in order to get by to the next month, you go into that hustle mode. You go into “how can I make money? What can I even do? I don’t care if it’s within my expertise. I just hope that I’m able to make it by to the next month, or the next week even.” And so that’s where I was.

Thankfully, because of my background, I had a lot of design friends. I’d worked for a lot of agencies. And in my corporate career, they hire freelancers at American Greetings. So basically, I went into this, like, “I don’t know if everybody has the access to those people, but I think if we look hard enough, we can go connect with the right people to get us the opportunities that we’re desiring. So what I did is I just emailed everybody that I knew asking for work, whatever it could be.

One of my big tips is when you are in that phase, get creative. Don’t let anything hold you back. Figure out where you can get income to get you by with the time that you have. I thankfully was not in a pandemic. I didn’t have children at the time. All I had was time and energy to be able to make this work. So basically, as I was doing that, there were a couple of transitions that I made in those three months without really realizing it, because I was so nose down, “Let’s get this done, let’s get money in.” But there were two things that I was doing during that time kind of subconsciously.

I started taking on retainer work. That meant that I had some stability in the work that I was doing. So I was taking on monthly retainers. That started piling up where I was getting $2,500 retainer or $3,000 retainer, and I was able to start making my monthly income increase a little bit there. And then as I was getting out of the hustle mode, I was taking on higher value lower time work. So booking more bigger website packages, booking bigger brands, really trying to get more income coming in instead of doing these hourly jobs. So they were more of my expert level work that I was getting done.

I remember it was right before Christmas, the beginning of December, I looked at my monthly income for what happened in December. And I’d hit $16,000 that month. It almost shocked me. I was so just like, “Kelsey make the money, Kelsey, survive,” that I didn’t even like look up to see what the numbers were. I just knew that I was in that hustle mode. So by doing those things, I was able to hit my first five-figure month and hit $16,000 that month. You have a question?

Joe Casabona: Oh, yeah. That’s great. If it’s not going to mess you up too much, I want to point out…

Kelsey Kerslake: No.

Joe Casabona: Cool. I want to dig in on a couple of things.

Kelsey Kerslake: Yea.

Joe Casabona: First of all, you mentioned that you emailed your whole network, your connected people asking for work. One of the pieces of advice I got going from college because I went to grad school to basically build my business, one of the best pieces of advice that I never took that I didn’t realize until later—because youth is wasted on the young—is to get a real heavy quotes or a corporate job, and see how professionals in your field are doing it, make those connections, and then go out on your own and use what you’ve learned.

I’m not saying that that’s great advice for everybody, but it is something that I learned was definitely good for me. Because when you’re doing high-level coding stuff, self-taught can only get you so far. And when you’re working remotely at home all the time, it’s different from being in an office and meeting people and making those connections. I just wanted to point that out because I think some people are like, “I don’t need to get a real job or whatever.” But there’s value in that if it’s a way to build your network and learn your craft.

Kelsey Kerslake: There definitely is. And I will say because I built my business from a… I was blogging back in the day when I started, I built a really great network of online friends. I think what is cool about what you’re doing, you have your community, people are getting to meet each other, when you get in those like-minded places online, that can build your network too. So even though I did have people from my corporate job that I was reaching out to, a lot of the agencies I was working with were people that found me on Pinterest.

So it was like the side work that I was doing that I met from people online. That was not something that happened because of corporate. So corporate is just one avenue, but because of what we have available in community building online right now, that can be huge too.

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And now let’s get back to it.

Joe Casabona: My story relates to about 10 years ago… when I said my corporate job. And communities were still a thing. I remember FreelanceSwitch but they were not as big as they are now, and they weren’t needed as much as they are now. But you also mentioned Pinterest. This is the third time this year as we record this that Pinterest has been mentioned on the show. I really, really need to start doing more Pinterest. I think the big takeaway there from your stories, and my anecdote is get out there, build your network. Even if you have a corporate job now go be part of communities, build a community in your side hustle somehow, be on Facebook be active because having a network and good connections will pay off. And don’t be afraid to ask. I think that’s another thing that a lot of people need to learn.

Kelsey Kerslake: There is a quote I always remember. And it’s “for every 10 nos, you get one yes. And that’s how you win at everything.” So don’t be afraid of getting that no. As long as you’re getting the nos and putting yourself out there and asking for things, you’re bound to get one yes over time. And that’s going to build for you. So I think that that fear of failure and rejection is something that we just need to at least squash while we’re hitting the email send button and just go ask for it.

Joe Casabona: Yeah, for sure. I mean, if someone says no, they’re not going to talk about it later. “Somebody just asked me this. I can’t believe it.” It’s going to weigh on you more than it weighed on that person.

Kelsey Kerslake: Exactly.

Joe Casabona: So that’s an important point to remember

Kelsey Kerslake: Totally.

Joe Casabona: And then you said you did two things that maybe you were doing subconsciously. Taking on retainer work. I think that’s super important. Whether it’s like services or monthly subscription product or something like that, it just makes your income more predictable.

Kelsey Kerslake: Absolutely.

Joe Casabona: And then you were taking on higher value, lower time work instead of hourly jobs. I feel like maybe you were about to launch into this. But I’d love to know how that happened. Because I feel like people get stuck in the… well, I charge $2,000 for a website and nobody’s willing to pay more than $2,000 for a website. So I’m afraid to ask for more because I’d rather have the 2,000 than lose that job.

Kelsey Kerslake: Absolutely. I think if you’re in survival mode, please go take that job. And if you have some of that cushion built up, then it’s time to see what are the offerings and at the prices that are actually going to get you to the business that you want to be building. So I realized that once I kind of got out of that survival mode, I had a few retainer clients, I knew my bills were going to get paid and I wasn’t looking, like, “Oh my gosh, I hope I can pay for my things next week,” then I started realizing like, okay, I can start to turn down some of these other things and really focus on the ones that are going to have the most impact and actually built to this business that I’m desiring. And that’s really that December in that timeline was when I started focusing only on those projects.

Joe Casabona: That’s great and super important. I’ll tell this story now, several months after the fact. But I took on a job in early 2020 and I got a down payment, and then the client disappeared for a year. I don’t have a kill switch in my contract. I do now. But they came around a year later and they were like, “Hey, we’re ready to pick this up again.” I just refunded them. I was just like, “You know what? This is not in my purview anymore. This is not what I’m focusing on.” I should have protected myself a little better. But I know that doing this work now will hurt me more than harm me. Even though I’m saying no to money, I’m in a good space for that. And I know that even though that down payment was nice and paid taxes on that for 2020, I knew it would have cost me more in the long run. So looking at the type of work you’re doing and focusing in on it, when you can is I think really important.

Kelsey Kerslake: Absolutely. It feels hard and weird at first, but you have to be making those decisions for that future version of you. And once you’ve decided like, this is how much I need to be charging in order for my business to be the way that I want it, you have to start making decisions in alignment with that.

Joe Casabona: Yeah, for sure. In December 2017, you’ve realized you’ve hit this milestone, it must have felt amazing, what was… I guess I have two separate questions here. I’ll ask this one first. What did your expenses look like? Because running a business does cost money. People either spend way too much or not enough. So what did that look like for you? You’re building up this cushion, did you cut expenses as much as possible? Or did you spend money smartly?

Kelsey Kerslake: I cut expenses as much as possible. I will say for a web design business, and you probably get it, our expenses aren’t crazy compared to some businesses. And I had invested a lot that year before. So I was investing in team and all of the stuff that I thought I needed support with, but I didn’t actually have the business know-how in order to make it more profitable or to actually put those investments to work. So that year… I’ll get real with numbers. I can’t remember my exact expenses, but my revenue for 2017 was $44,000.

Joe Casabona: Nice.

Kelsey Kerslake: So that 16,000 was like a quarter of what I’ve made coming in just at the last month, which is like, you know, that’s where the whole rest of the year, like, what was that looking like? I don’t know. But probably like half of that was expenses. Compared to me and my corporate life and being profitable with my side business, I was making six figures then. So to go down to that for where I was, that was like, “Oh my gosh, I gotta get stuff working for me again.”

Joe Casabona: That resonates with me so much. That’s such a tough revelation. Because when I left my agency job, there was some payroll issues. It was rampant across all WordPress agencies at that time. I was bringing in money with my side hustle, I was newly married, my wife was pregnant. And I was like, “I don’t need a full-time job. I’m making so much money. I can support us just on my side hustle.” And then I went out and like towards the end of the year, I’m like, “Where’s all this money I thought I was going to make?”

Kelsey Kerslake: Yes. We’re in the same spot after one year. Yeah.

Joe Casabona: Luckily, I had really good friends in my network and my wife went back to work. I started my own company three months after my daughter was born. Best time to start a business really is when you have a new mouth to feed. And I had the savings. In a couple of weeks, we’re going to hear an episode from Travis Hornsby about the financial aspects of starting a new business. But that just resonates with me so much. Because when you have the safety net of a full-time employment job, your side hustle looks like it’s so good, because you don’t really need to run a business that well. It’s just extra money that’s coming.

Kelsey Kerslake: Yeah, exactly. So when it became this actual thing that I had to make to survive, things really changed and I ended up where I ended up. So it was a big switch for me.

Joe Casabona: My second question here… first of all, you cut as much as possible. You’re right. As web designers, we don’t have that many expenses. It’s like hosting is my biggest expense. Maybe I pay for some WordPress plugins annually, but other than that it’s like…

Kelsey Kerslake: I think my business expenses at that point were probably around $300 per month. When it came down to that bare essentials for like my invoicing system and just my website hosting and things like that, it was $300, which is nothing compared to a lot of other businesses.

Joe Casabona: That’s like 1/6 of rent for a brick and mortar store.

Kelsey Kerslake: Exactly.

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And now let’s get back to it.

Joe Casabona: The second part of this is, once you made this realization and you did two of these things, what did you do to continue that trend? Did you put a system in place or some rules in place?

Kelsey Kerslake: Oh, yeah. I actually started watching my finances all of the time. And then I really said, “Okay, what happened here that made this successful.” That’s really when I looked back and realized it was retainers, and it was these expert-level offerings. So I just went all in really in those two areas. And I also decided… and I’m big into energy and woo a little bit. So I was like, “Okay, what does the future vision of Pinegate Road look like?” And when I envisioned that, like a year out, three years out, I knew that it was an agency style model, but where everybody was working virtually on their own time. But I knew that I needed to bring on team and that I wanted to be the one doing the sales and the marketing and getting the new clients and that I’d have team doing.

So even though I’ve made $45,000, the year before total, or 44,000, or whatever it was, I decided, I was like, “Okay, like, I am trusting in this future version of myself and where I want to be heading. And even though it feels really, really scary right now, I’m going to invest in a team and I’m going to do this right.” And right then and there I decided to not just become Kelsey the freelancer, but become Pinegate Road the agency. I hired my first two team members who are still with me today and scaled from there, even though I was barely paying myself.

Joe Casabona: That’s amazing. Are these full-time employees? Are they contractors?

Kelsey Kerslake: They are contractors. I’ve actually built my team to 15 contractors over the past… So, that was 2017 and obviously, now we’re in 2021. So that’s been three years. Actually, this month is the first month where we are transitioning. I now have a full-fledged coaching business. And we are finally transitioning people to employees three years later. That’s something I’ve been really scared about as well is “Oh, my gosh, it’s not just me that I’m taking care of. It’s these team members and their families and all of that.” So I’m finally at a place where that is where we’re heading.

Joe Casabona: That’s amazing. I’ve kind of gone through a similar thing over the last year or so where I have a couple of contractors on a… not really full-time basis. I send them work as I can. But one is a virtual assistant who I feel like I need to regularly send her work so she doesn’t leave me. But it’s a scary thing. But you made the investment. I should say that you knew what you did wrong, and so you were able to kind of course correct. What were some of the changes you made in hiring a team? Because I know that that’s something a lot of people are scared to do. But if they want to grow you, there’s only one you and there’s only a finite amount of time you have.

Kelsey Kerslake: Oh, yeah. The first thing that I did was I figured out what was the thing that was taking up a lot of time that I didn’t love doing. And for me, that was developing the websites funny enough. I mean, I love doing the creative stuff, but the actual sitting there and like developing was… I wanted to cry on my keyboard. That was not something I like to do. So I hired a developer who came on to develop all of our sites. And that saved me about 40 hours per site that we were doing. And then the second thing was what is taking up the most mental energy? Because that is actually holding you back from being the business owner that you want to be when you have all those spinning thoughts in your heads, the what-ifs and the client details and the emails and all of those things.

Even though writing my clients and email and sending the contract and doing these little things here and there didn’t add up to a ton of time, the energy that it took inside of my brain was massive. So I knew that in order to clear that up, I needed to bring on somebody who was going to take care of my clients as well or better than I would and they would own that client experience. So I brought on my account and project manager. She is the one that as soon as somebody books, they work with Janet. And Janet manages the entire team of contractors and gets them all set up. But that was kind of me. She was basically re-contracting out to Kelsey the brand designer, Kelsey the website designer, Kelsey the art director. But we built those systems and processes in as if I had this full-fledged agency even though it was three of us.

So I think that first thing is, you know, get some of your time back and your energy back. And then as soon as you have that time, start to design the business as if it is that future version of your business, you know, a year from now, five years from now. What decisions can you make today that actually get you to that vision?

Joe Casabona: I love that. What decisions can you make today that will get you to the vision of the business that you want? I think that’s super important. Now, you mentioned that bringing on the contractors was scary because you were paying them and you were barely paying yourself. What steps did you take to manage your money appropriately to start paying you like what you should be paid? Because if we’re not paying ourselves in the business, we might as well have a full-time job.

Kelsey Kerslake: Totally. I think then I also realized, like, “What is the minimum income that I need to live off of and that I need to pay myself?” So I started doing an automatic checking draw to my personal account from my business account. I pay myself as an employee. I actually am the employee of my business. So it’s just making sure that I have that covered at first.

And then I also went through our offerings, and again, visioning out what that quote-unquote, “agency” looks like? If Kelsey were gone, if I were gone, who would need to do each step of the process and how much would that cost? And so mapping out how much our offerings actually cost the business and then pricing them to be profitable so I’m making money on top of that was a game-changer.

And I did that as soon as I brought on team. I made sure that what we were selling are projects at were actually profitable for the business so that even if I had to hand off everything and I’m out of the business, which is where I’m at now, I don’t really do anything in the business, and it runs, I do some kind of direction, but everything else is handed off to team and we’re still able to be profitable. So just doing that and selling at those rates over and over again, it just eventually make sure that you’re covering you as the CEO, and then the entire team as the pieces and parts of the agency.

Joe Casabona: What an incredible piece of advice or an incredible story that you mentioned here! You went through your offerings, took yourself out of it, and then figured out: “How much am I paying somebody to do this? Now let’s make this profitable.” I’m sure that somebody said something like that to me at some point, but not quite in the way that you said it. And it really sticks. I love it.

Kelsey Kerslake: Awesome.

Joe Casabona: So now I’m going to get to play that game later with some videos that I make and things like that. Just to belabor the point a little bit, at least for me, the contractors are replacing things that I don’t want to do or that I don’t do as well. So like my podcast editor, Joel, thank you, you are invaluable to me. My video editor, Fred, does a great job. I can edit videos just fine, but Fred does them great. And it’s worth it. As I start to productize more of my services, that’s something to think about.

I do want to ask you one thing that I noticed you do. You keep saying team, not the team or my team. Is there a reason for that? Or am I pointing something out to you right now that you never noticed?

Kelsey Kerslake: I never noticed it.

Joe Casabona: Most people I talked to usually say like, “My team does that,” or “the team does that.” But it sounds like team is a proper noun for you.

Kelsey Kerslake: Oh, you’re getting grammatical here. I don’t know. The thing is, is now I’m a mentor to so many designers and coaches and people that I use team in a way I’m not ever talking just about my team. I’m usually giving advice and we’re talking about their teams, this team, that team. So I think that’s probably why I just say team because I’m not always mentioning my team. I could be talking about your team.

Joe Casabona: Yeah, true. I like it a lot.

Kelsey Kerslake: You made me think there.

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And now let’s get back to it.

Joe Casabona: I can’t believe we’ve been talking for as long as we have. First of all, before we get into tips for the listeners, is there any other part of your story that you want to share? I’ve asked I think a lot of really good questions. I think the listeners have a lot to think about. But is there any big part of your story that we didn’t cover that you think would be important or interesting.

Kelsey Kerslake: We did cover this, but I would say the biggest thing that I always go back to is envisioning where you literally want to be in 12 months from now. And when we’re making decisions from a place of just trying to get to the next day or our heads are down and we’re just like making these decisions that aren’t adding up to where we actually want to go or we haven’t actually thought about that bigger vision, we won’t get there.

So really think about that future vision. And don’t just say, “Oh, it would be nice to have free time one day. It would be nice to do this.” It’s this kind of like fluffy vision. Get really, really clear and take that time to imagine what your days look like. What does the team structure look like? What are you actually doing day to day? What does your calendar look like? And what are you able to do on your time off? And then you can design the business to get there. I think I’ve been able to do that every step along my career and it’s always gotten me to where I want to go. So it’s intentionally designing your future instead of letting things just happen to you.

Joe Casabona: I love that. It makes me think about if you have a deadline you actually need to hit, you’re more likely to hit that than when somebody says, “Just get it done whenever.” When someone says, “Get it done whenever,” I’m probably not going to do it until you say you need it by that date. Right? The other thing I thought was Bo Burnham Are you familiar with Bo Burnham? He’s like a musical comedian. He’s very funny and vulgar.

Kelsey Kerslake: I feel like I’ve heard of him, but I don’t know know him.

Joe Casabona: In the middle of one of his bits, he says like, “Tomorrow’s a relative term.” Like tomorrow is today or whatever. And then he makes a joke about how that makes the Annie’s song a lot more depressing. But, like you said, if you just say like, “Whenever” or “someday” or whatever, you’re never going to get to that. But if you say, “In March 2022, I want to be able to take Friday’s off but still have the business running or whatever,” like whatever that looks like for you, then you know, “Okay, well, if I want to take Friday’s off, I need to hire a content writer to write that blog post that always comes out on Friday or whatever.”

Kelsey Kerslake: Now that you’re speaking about deadlines, I did kind of forget a part of my story. I actually was pregnant with my son. And that’s when I was like, “Okay, gotta get team ready and set so I can actually like take a wonderful maternity leave.” And I pictured, “What do I actually want to be doing on maternity leave? How does the business need to be structured in order to get there?” And that was my big deadline. I don’t know if I would have everything set up the way I do if it weren’t for that deadline.

Joe Casabona: That’s absolutely amazing. That is an immutable deadline. I love that. My son was born in June and I was able to take a couple of… July, gosh. My son was born in July 2020. I was able to take a couple of weeks off, but the pandemic and my daughter being home from daycare and all that, that was the big catalyst for me making some hires because I was not working half of the week because I was watching my kids and the business still have to run.

Kelsey Kerslake: I just worked nap times for a while, because we’d had daycare, and then all of a sudden, it was gone. I’m really glad that I did structure my business to run without me because it basically was at that point, and it was still able to support our life.

Joe Casabona: Likewise. I’m grateful for everything I’ve learned on this show to help me do that. I have two now and simultaneous nap time is like the most coveted. When I get it, I’m like, “Thank you.”

Kelsey Kerslake: We’re planning for number two. And I’m like… I just don’t even know how… I just don’t know.

Joe Casabona: You do it. I don’t know. You’ll rise to the occasion. Two was very different than one for me. Maybe we could talk about parenting too in Build Something More. Speaking of if you are not a Creator Crew member, then you’re going to miss out on this great nerdy stationary conversation that Kelsey and I are going to have, as well as all of this other great content. So if you want to sign up for just $5 a month, you can go to But right now, Kelsey, do you have any… You know, I say tips for the listeners. You’ve given us so many. So I’ll just cut right to my favorite question. Do you have any trade secrets for us?

Kelsey Kerslake: So I actually wrote this down before, and my biggest trade secret is higher now for where you want to be in six months.

Joe Casabona: Awesome. Hire now for where you want to be in six months. I love that. I mean, you’ve given us a wealth of examples. But I guess the example I gave earlier, if I want Fridays off and I know that something needs to be published on Fridays, I should hire somebody to publish on Fridays for me or whatever. The transition I’m going through currently is that in six months from now I want employees who are working 40 hours per week in my business doing a lot of the doing that I feel like is on my heart right now.

And so I knew that in order to get there for my coaching business I wasn’t going to be able to pour into contractors with my training and my guidance the same way that I can pour into employees who were in it with me. So I just went through a big reorg and transition from moving from contractors to employees. And that was because I had to hire now for where I envisioned my business in six months. And that scared me. Things have been running really well and I had wonderful contractors that have been with me for a long time. And I took my own advice, and we’re transitioning. I think for the long term, it’ll be a lot better even though it’s hard right now. It’s not hard, it’s just it’s a big change. So there’s feelings that come up with all of that.

Joe Casabona: Yeah, absolutely. And you’ve mentioned this multiple times throughout the show. These things scare you, but you do them anyway. And they genuinely pay off, right?

Kelsey Kerslake: Yeah.

Joe Casabona: Because you’re not just gambling.

Kelsey Kerslake: No.

Joe Casabona: You’re taking calculated risks based on your gut feeling, but data and things like that as well.

Kelsey Kerslake: But you’re also taking a risk on yourself. And what better risk can you take? Can you trust anybody else as much as you can trust yourself when you almost back yourself up against the wall to have to do the things? I think this is a weird reason why coaching works so well, especially high-end coaching. Because when you invest in some of those things, it’s like, “Oh, crap, I gotta go do the thing now. I have no other choice.” And when you can put yourself in those situations, as scary as it is it, you literally energetically become that future version of you when you make those choices.

So I’ve done it time and time again enough to know like, “Oh, crap, here’s this weird, scary feeling.” Then I jump in with both feet because I know it’s where I want to go. Even though I’m probably going to cry about it now, but I’ll be really thankful in the future.

Joe Casabona: Yeah, amazing. Amazing. Take a risk on yourself. Friends, that’s not the last time you’ll hear this in upcoming episodes. So a little peek into the future, you’re going to hear that again. So remember it. Kelsey, this has been absolutely amazing. Again, your story just resonates with me so much so I know that your story resonates with the listeners too, because we’ve all been there. Running a business is hard. But if you have the gumption and the wherewithal to see your vision through, then it’s going to pay off for you. If people want to learn more about you, where can they go?

Kelsey Kerslake: They can go to I actually have some little freebies that you can grab to help you on your journey. Our most popular one is about 25 profitable offering. So if you’re kind of stuck in that, like, “How do I raise my rates? And are people actually going to pay for XYZ service?” this gives you 25 services that are tried and true that I’ve done that I know people purchase that will get you to 10k months by implementing these into your business.

Joe Casabona: Love it. I will link to that and everything we talked about in the show notes over at If you are a Creator Crew member, a builder if you will, you’ll get to hear the second part of this conversation in Build Something More. If you are listening on the regular feed, thanks so much for joining us. And Kelsey, thanks so much for spending time with us today.

Kelsey Kerslake: Thank you so much. This was awesome to get to know you and chat with your listeners.

Joe Casabona: Likewise. Likewise. And thanks to our sponsors, TextExpander, Restrict Content Pro, and The Events Calendar. Until next time, get out there and build something.

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