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Things To Consider Before Quitting Your Job To Start A Business

In Conversation with Ashley Segura

For this episode of Ecoffee with Experts, Matt Fraser hosted Ashley Segura, vice president of global operations at Top Hat Rank. Ashley offers guidance to people wishing to make the transition to entrepreneurship during the chat and shares her experience as an entrepreneur. Learn some crucial lessons by watching this now.

Don’t be afraid to pull the plug and take the lead. There’s so much opportunity out there, hone in on what you want to offer, and what you’re passionate about it and go for it.

Ashley Segura
Vice president of global operations at Top Hat Rank

Hello everyone. Welcome to this episode of Ecoffee with Experts. I’m your host, Matt Fraser. And on today’s show, I have with me Ashley Segura. Ashley is the vice president of global operations at Top Hat Rank. An award-winning SEO marketing agency headquartered in Sherman Oaks, California. She has a bachelor’s degree in journalism from Humboldt State University. And over eight years of experience in the digital marketing industry, working with marketers, entrepreneurs and business owners from around the globe. She is also an in-demand international speaker, teaching at digital marketing workshops and speaking at industry conferences like Pubcon, Brighton SEO, Search Lab, Digital Summit, Retail Global and the prestigious SMS Sydney. In addition, she has also co-authored the bestselling book The Better Business Book, Volume Two, and is a contributing writer to industry blogs such as Search Engine Zero and Authority Labs. When not working on the running operations of Top Hat Rank, Ashley enjoys mountain biking in the mountains of Oregon and spending time with friends and family. Ashley thank you so much, it’s a pleasure to have you on the show.

Thank you so much for having me.

Hey, right on. So, Ashley, I would like to ask this question. How would your university professors describe you as a student?

As a student, I suppose that would be ambitious because I was the only one in class who actually volunteered to head over to Japan when the tsunami hit. Other than me not a single person raised their hand.

Wow. What was that like? That must have been interesting.

It was very interesting and it was very powerful to be able to be there on the ground telling the stories of people who were just impacted.

Yeah. I remember when that happened because I was working at a massive dealership and inventory was greatly impacted in regards to us being able to get that. So, what would you say is the biggest difference between the person you were in university and the person you are now?

Business operations.

Business operations?

Yes, marketing has always been there. It’s always been top level and I think from a business standpoint, I was in three different agencies. I’ve worked in-house, I’ve worked for agencies and the amount of operational learning has just been extensive.

Absolutely. That’s amazing. So, based on that, do you think that the experience you gained at SEMrush has helped you in your development as an entrepreneur and overall digital marketer?

100%, that immersion was absolutely vital to me because I was able to learn so much and literally travel around the world and get to speak to other marketers, learn what agencies and brands are doing, contribute strategies to them, and definitely get around things.

Do you think that other entrepreneurs, like people who have ambitions to start an agency, should go and work for someone else first before throwing their hat into the ring and launching their own agency from scratch?

Yes, 100% is the difficult route, which is why so many people don’t do it and just say, I’m going to open my doors today, cross your fingers and wish me luck. But I worked full-time in-house then I worked full-time at agencies. I wanted to learn how to really market a brand, truly. And then I wanted to learn the agency operations of things like those full-time positions. Nights and weekends were when I was operating my own company and started to build it.

Wow, that’s awesome. Have you always wanted to be an entrepreneur?

I’d say so. I think it’s pretty safe to say.

Yeah, well its sounds like it because it’s pretty ambitious to put your hand up and go to Japan after the tsunami. Were there indicators as a child that you like you know, they say a lot of people have like newspaper outs or lemonade stands or whatever the case may be? Were there things like that going on in your life at a younger age?

Very much so. I had my first job when I was 12 years old. I wanted to work, I wanted to make money and that just opened up this whole new space in my mind of what it means to make money on your own, and be independent. Obviously, I had an amazing family to support me but to show up and actually start working at that young age while still balancing school really taught me how to do that. Multitasking while instilling entrepreneurship.

Yeah, that’s pretty remarkable. I had my first job at when I was 14 at a restaurant. But anyway. So, that being said. In the Better Business Book-Volume Two, you wrote a chapter titled How to Know When It’s Time to Take the Leap, in which you shared how it took over five years to leave the stability and security of your job. What was it that held you back and do you wish you had made the leap to entrepreneurship sooner in the five-year period?

Such a great question. So, it took five years because I wanted to make sure I actually had a good grasp of what it meant to really market a brand, and what it meant to really run a business. Could it have been faster? Maybe, yes, but of course, I don’t know if you have this, but there’s that little voice in your head that has that self-doubt every once in a while, and sometimes you produce a little bit more experience or you should learn more about this part of business operations. It wasn’t until I felt like, okay, I’ve done what I could at the top of the agency. I moved my way up to the director position and checked that box. I marketed the in-house brand to its max capacity where I built out the marketing department, and both those boxes were checked. So, it just felt secure that if I take this leap, yes, it’s going to be challenging, but I at least have all the toolsets now to be able to deal with those challenges as they come.

Absolutely. You know, you talked about that small voice of doubt or whatever. I personally suffered from imposter syndrome for many years. And there was an email that went out from Jeff Sauer of Data-Driven U, that kind of awakened me to that whole idea of was that thing even real. But was that something you ever struggled with as well?

100%. It’s one thing to have the safety and security of a paycheck and knowing that you’re working for someone else’s business versus when it’s on you, it’s 100% just on you. If you make a really big mistake with a client that could ruin your entire agency, you can ruin your reputation. It can just crumble everything. And so that imposter syndrome definitely comes up. But I started working with business coaches and entrepreneurship coaches, and that really helps kind of fight back those thoughts and pursue them.

Wow. So, do you think it’s important for entrepreneurs to have a mentor, as you mentioned having a coach?

Yes, definitely. And that mentor can look like a lot of different things because it depends on mentorship. So, for example, in the first agency that I launched, I thought I had my pricing structure down, I thought things were great and then I saw other single individual agency owners like myself were charging for services and I was so underpriced. So, I reached out to a business coach who specializes just in pricing services and they actually structure my pricing.

Oh wow. To be frank with you, I never thought about hiring someone, but that was one of the biggest challenges I had when trying to launch my agency. Especially when it comes to web design because in web design each and every single website is so unique and there’s so much opportunity for scope creep. And you literally have to guess what it’s going to take to do this and the number of hours. Sometimes you could be wrong. Like I know one agency in my city, they don’t even do e-com anymore. They tried building e-comm sites like Magento or WooCommerce or whatever. And he’s like, Matt, no matter if I charge 60, 80, 90, or 100 grand, I still sometimes lose money. Now they are just Shopify consultants, we just consult and it’s hard to push back on those things. So yeah, pricing services is really hard. You mentioned in the book how you decide to try and find your ideal client and how you raise your prices. So, what was your process for identifying your dream clients to work with?

A whole lot of trial and error in order to make this my dream. After a couple of years, I started to recognize, here are clients that are taking up way more time than what we’re billing and what we’re actually putting out in terms of support and whatnot. And then there’s that are those quote-unquote, dream clients, and I write about that brand that looks like what your dream customer is. And so, I can identify that profile by first acknowledging what it looks like on a negative basis.

That’s really smart.

And then recognizing what a positive dream client would be. Then how to attract that client and that also kind of aligns with the pricing of services because like certain services, bring certain types of clients with them. An expert in price point, I will attract that level of clients as well. That’s not to say you always have to charge tend to have a great client, definitely not. Small mom-and-pop can be amazing clients as well. But in my agency experience, that really helped me hone into what services I wanted to offer and at what price range, because I was able to identify a certain client now.

Did you take a look at the annual recurring revenue of a dream ideal client is one of the factors in regards to who you want to work with? Like, for instance, mom and pop shops, I had a plumber who wanted to work with me and he just can’t afford me. He’s a startup plumber and doesn’t have any money. I don’t know what he’s going to do, but he can’t afford a marketer. Sometimes I think people should give up equity in their business to have someone like us be able to work for them. And I know that’s a trend right now in the industry to have someone like us contribute to their business just in the same way as a CFO or CMO. But did you use revenue as an indicator of what the ideal client looked like? Was that a factor?

Revenue was definitely a factor, but also resources. So, if there is a one-stop shop. Are they the only ones in this business who have to run the business, manage the business, and do whatever? I strategize for them or whatever the service was. But if they had to have a marketing department, comms department, or even a sales department. That would even be fantastic if there was just a sales department. So that would be an indicator that the work and effort that I’m going to produce for this client could actually be executed because they’re selling it.

Okay. You also talked about scaling back your services, which is something that people get afraid to do. People think that they have to be all things and everything to everyone. But yet you found your dream client and then there were certain services that you decided to scale back, in other words, that you decided to offer. So, how did you determine whether or not a service was worth offering to clients?

Well, to be honest, it was quite terrifying of a process because I started being at one stop shop. I was doing everything from web development, landing page optimization, and email marketing. Like literally doing it all. But once I realized that some of my happiest clients are from the social media services and the content marketing services that I’m doing, I’m also happiest doing those services. That was all this synergy that I needed, to get rid of web development and email marketing. Let’s focus on specific content marketing services and social media marketing services. And then that also helps dictate, help me zone in on pricing again and restructuring my pricing now that I’m specializing in just these two services and then attracting clients who need and know that they just need these two services.

Wow. You know, a lot of people would be afraid because they think, well, if I don’t offer everything, they’re going to go and get somebody else. They’re going to hire somebody else that’s going to steal them from me. How did you solve that problem?

Again, just making the leap. Kind of crossing my fingers. Having enough clientele already that we’re requesting and meeting those social media and content marketing services. So, I knew it was something terrible that happened and I wouldn’t be able to get a lot of new clienteles. I at least had a strong baseline. I always wait till I have a baseline to make a leap and cross my fingers that it works out. And then once that’s published, that’s exactly where I went down the rest of my career path. To this day, I’m still specialized in just content and social media marketing services.

That’s amazing. Because, like you, I didn’t do everything for clients, but when I was at the dealership, I did everything from Google ads, Facebook ads, SEO, local SEO, analytics, everything. Everything that there was to do. Photoshop, video creation, video creation planning and so on and so forth. It was insane. And I realized that if I was to try and scale that and do that for other agencies, it would be impossible. So, do you think it’s important for us as marketers? I think I don’t know who made it popular, but someone did. Being a T-shaped marketer, where you go deep on one facet channel of digital marketing, you see yourself in basic knowledge or whatever of other aspects of the channels. But then going deep, like you’ve gone deep on social media and content. If you could go back in time, would you start out that way right in the beginning? And would you recommend another aspiring digital marketer or somebody else who’s in journalism school and wants to become an agent? Is that the advice you would give?

I actually don’t think I would get that advice. It’s a little bit argumentative right now. I started doing everything there is now in digital marketing and I was even doing prints in PR because I did that. It allowed me to have this well-rounded base to understand content needs to support SEO. Yes, I do content, my original content stems from writing blog posts in creative writing. Back then, we would write 45 blog posts a day and just publish as much content as possible.

As you could.

Certainly, but also have an understanding of how to build a website. I know and I’m so incredibly comfortable working in the back end of WordPress. And so, like you said in the beginning, like rough basics of all of the fundamental aspects of digital marketing, not only will prepare you to really be an expert, but it also shines a light on what you like best. You may think you like social and then dive into social and go, oh no, that’s changed way too much for me.

I agree with you. Getting experience in everything first, doing multiple positions, learning multiple things, and then figuring out what you want. I think that’s a good strategy to take. Only things I wish I learned. I learned front-end marketing first and then I learned the analytics side of things because I had to have a necessity to prove that what I was doing was working. But in some ways, I wish I may be learned a little bit more about web analytics and KPIs and so on and so forth, earlier in my career than later. But anyway, how did you solve the problem, did you work with referral partners or did you find referral partners in regards to fulfilling some of those other services in your agency that you had stopped offering email marketing or you mentioned you stopped doing web design and so on and so forth.

Yes. That I totally wish I would have done it a little bit sooner because it creates such fruitful relationships with people in the industry who already did establish themselves as web developer or graphic designer. This is what I do, this is what I signed on, and was able to either create relationships on a white label basis or literally in some cases to where this needs to be completely hands-off. You need to be communicating and getting support directly from this other business or this other person. So, then passing over and creating referral relationships like that, that meant all of those other referrals were also coming back to me because now I have relationships. These people trust me, they see the type of clients I’m sending them there. They send me clients as well because they understand that not only do I say I specialize in this, but they’re understanding the relationship building that I do actually specialize in.

You’re not going to poach their business here. What did you find was the best way to find these potential referral partners?

A lot of the relationships I found with them were in conferences. I started talking in conferences in the first year of my own agency, and that’s how I actually generated my first round of clientele. That’s where I found all my partners, that’s how I discovered which brands I wanted to work on or not work on or things like that. In these conferences, there is a huge chance for building these relationships.

Absolutely. Hey, how did you get started so quickly speaking at conferences? I think a lot of people want to speak at conferences, but they don’t know how. What was your secret?

Just applying, applying, and yes, you’re going to get rejection. Having a speaker website definitely helps. That gets social support for what you do, and why you’re an expert in there. Gets some testimonials, and gets some great photos.

Okay, some branding.

Hire a photographer. I built my site, I knew how to do it. But yeah, you need someone to build your speaker site, get as much expertise and authority on there as you can. Not for Google but for the conference people that are looking for speakers, they’re going to go and check out your site and see if you really know your stuff. They’re going to want testimonials on there. They’re going to want to see any videos of you. One little speaker that I can totally pull this off is finding someone in your hometown that has a stage. Get a tripod, press the record button on your phone and just start talking. No one knows how many people are going to be there, 5000 people, or no people. But it’s showing that you can actually speak and present and the conferences are going to see this and be like, oh, I love their stage performance. I love how they’re presenting this information. I’m going to confidently reach out to them and tell them the pitch.

That’s brilliant. It’s such a great idea. So, I was going to ask you. What made you finally decide to start your own marketing agency Madhouse Matters?

Well, I guess the entrepreneurship drive was definitely in the back of my mind, and that’s where I knew I always wanted to be because I come from a background of wanting personal freedom. Starting a job at 12 years old to make money, buy a vehicle when I finally get a license, and be able to do things on my own. And so being a business owner comes with a tremendous amount of freedom. What people very rarely talk about is all the headaches and the lack of freedom.

Yeah. Michael Gerber talks about that in his book, The E-Myth Revisited, how this baker who owned the bakery had more freedom when he worked for somebody else than when he had his own bakery.

Yeah, it did take time. I eventually found the happy medium point. But, you know, when you start a new business, especially when you launch an agency, you are hustling and you have to keep hustling. Unless you want to make bones and you’re good with that, then you can do that four-hour workweek, and all power to you. But in the beginning, it’s a lot of work. It’s all day, it’s evening, and this weekend. You’re going for it?

What do you think are some key things that should be in place before someone decides to quit their job and make the leap into entrepreneurship?

Having a foundation already established. Since we’re talking about agency, I’ll use that as an example. Having one or two clients already.


That’s going to give you some kind of security if you are able to get those clients. You’re going to be able to get more clients. That also gives you an established testimonial base, you have experience and you understand how to do basic operations like invoicing, and things like that.

Things they don’t teach you. It’s one thing to be good at Google Ads or SEO. It’s another thing to be able to still run the operations side of things. Like, no one teaches you this and if someone wants to learn business stuff like the operation side of things that you learned hands-on as a result of working for other people, is that the only way to learn these things, or is there an agency operation manual out there?

I’m sure, with how many agencies are out there. Someone had to publish some kind of E-book.

Yeah, there got to be. Anybody listening to this who knows about it, come on the show and tell us.

That’s first-hand experience working at agencies. Once you’ve done it in-house and you understand the basics. To be more well-rounded as a marketer and then you got to have the mindset. Even though there may be an accounting department that’s doing things like invoicing and making sure your corporations are up to date all the time, you’re going to have a little bit of an understanding of what, and then you’ll dine with programs like Gusto or Cornet.

So, what were some of the biggest challenges you faced when first starting your agency in the early stages?

I say establishing what I really wanted to offer when I made that call to cut back on services, to identify a pricing structure, and then figure out how to keep new clients coming. That was really where the focus went after the probation was there. And for me, the best way to do that was to keep speaking, to get on stage. I would speak at California Chiropractic Association Conference. I’d go to the Assurance conferences. Finding niches in industries, becoming an expert in those, letting them know that not only are you an expert in X, Y, Z marketing field, but you also know how to do marketing for insurance agents or to fill in the blank.

Wow. I mean, you know, more people fear public speaking than death. But I think if an entrepreneur you need to learn how to public speaking, most definitely Dale Carnegie courses, you take lots of stuff. So, you would say though, that public speaking was definitely a way that brought in business for you, and in some ways, is that what you would recommend others to do?

Yeah. That was my number one market. I didn’t even do marketing for the agency until my third year because of my public speaking and then by year three, I want to really amplify in terms of volume on everything. But before you can even speak, you need a brand identity, your own personal identity, building that and absolutely speaking is definitely a way to do that.

So, your presentation that you developed, how did you go about the development of that? Was it based on thinking about what you were interested in content marketing and social media in regard to strategies and so on and so forth?

Yeah, actually my first speaking engagement was when I had just graduated college and my insurance agent was like, hey, you’re young, can you fix my website and help me with my marketing? You probably know about these things and I had no idea I was a journalism PR student. I did it for the college, but all everything else was totally out of my wheelhouse. So, my entrepreneurial mindset was like, yes, I can do all these. I can figure it out. So, I did figure it out. Did marketing for his company while I was working in-house for another brand, I had my first clients and so after a few months of doing marketing for him and building him a new website regularly creating blog posts and social media forum, he’s like, there’s a big insurance conference coming up and I’ve been telling people about what you’ve done. Can you come and speak? We have an open speaking slot in marketing and so I get an entrepreneur mindset. I said, yes, sure. I’ve never done a presentation like that before, but I did it. And so that one was very specific to insurance for me, but I just showed what I was doing for him and how it was.

Wow, that’s so smart. So, you started off in journalism school, and then now you’ve pivoted entirely to marketing. Was that what guided you down the path?

I was going to be a National Geographic journalist. That was the goal, that was the plan, circled back to that one day. But when I pivoted, I graduated and finished my schooling in December. And literally in January, he reached out to me. And so, I started right away down this marketing path and I found that it was a way to still tell stories but from a brand perspective instead of just a human demographic perspective. It was completely different storytelling. But it was also a way to craft stories and get paid to do it. Whereas Prince was going through this really weird transition. So, I was like, all right, let’s adopt, let’s try this out and I loved it.

That’s awesome. Your education still came in handy because I mean, how could it not? You developing stories for brands and learning how to do that. That’s amazing. You know, many experts say that the ability to pivot is one of the most important skills an entrepreneur can have. Can you share a time when you had to pivot and how you did it?

Definitely so pivoting from in-house to agency life was a huge change, it was so different. In-house I was everything. I did all of the marketing hats or of them. And then I realized if I really want to take my side business somewhere, I need agency experience like we chatted about. And so, I then went into an agency environment and decided I’m just going to specialize in social and this agency environment. Because that’s what I was most recently doing for clients is social. And that’s when Facebook started doing advertising, too. And so pivoted, I paused on everything content and just focused on social. For about two years, I worked at one agency just doing social for them. And that’s where I was able to at that point, I was no longer talking about content marketing. I was presenting, I was just talking about paid social. And it was at a time when two years into Facebook paid. It was huge and everyone was talking about it.

Oh, that was amazing.

An expert on this. I could still generate content in the background, but I went instead of being content and social, I was just social for a while.

Wow. That’s amazing. Yeah, pivoting is so important. Hey, what are some tips for finding a balance between personal and professional life as an entrepreneur that you’ve gleaned over the years that you could share?

It’s a fantastic question. It’s very different for everyone because everyone’s personal lives are so different that when I was juggling, working full time and working nights and weekends, I eventually learned how to prioritize what really needed to be done that day and what didn’t need to be done that day, what could wait. And so then that helped me to actually schedule out my tasks over certain days instead of working every single day these long 12, 14 hour days. We’re really honing it down and just prioritizing. This absolutely needs to get done and needs to get sent out today, these others can wait until two or three more days. And so that’s on me to really clear our calendar. Mentally I would be able to say, okay, I don’t have to work every night this week in order to make this work.

Did you find time blocking helpful, like sending a set schedule?

Yes, time blocking is still what I do to this day. I dilute it to the point where I will literally put a block on my calendar and say, for this hour, I’m focusing on this thing, and in the next, I’m focusing on this thing. So, I have a project management system that I use, I have a notepad, I have a to-do list, and I have a virtual to-do list as well. I’ve got all of the project management systems in place. It’s really powerful seeing it in your calendar and saying, okay, this hour is up. Time to move on to the next thing before you rabbit hole down this.

Yeah, exactly. And spend too much time. I do that with email. Like once there’s a certain amount of time scheduling emails and if it doesn’t get done and then I prioritize the email even. I use our active inbox HQ.com. I’m not sure if you’ve heard of that big shoutout to them. If anybody uses Gmail, it turns their inbox into a project management system. Not a full-blown one, but at least for individuals. So, I don’t know if you use Gmail, but if you do it’s like a must-have for me anyway. That being said, I noticed it, and this question we can edit this if you don’t want to answer. but I notice that your agency Madhouse Matter, closed it up, and you’ve chosen to go on, go and work for Top Hat Rank, which is owned by Arsan.


Would you care to share the story around that?

Of course, not headquarters. I had that agency for eight years. It started as marketing then became a completely different agency, then rebranded over to Madhouse Matters. And towards the end of the agency, I was working with a SEMrush and that just completely consumes my time, energy, and my focus. After SEMrush I decided, okay, I’m going to go back into agency life a little bit, but I also don’t want it at the level that I had before. I had done agency ownership for eight years and was really burnt out on it. As many systems that I put in place, I was just simply burnt out on agency life. And so, when arson and I were good friends, we both speak in the industry, and he and I gather and he approached me about doing operations now, business operations that I never got burnt out on. I love operating businesses. I love figuring out how to optimize a standard operating procedure for a client’s success, all of that. That is totally wheelhouse. I love all of that and so there is just great synergy there to take off the agency owner hat and this also goes back to just focusing on the specific services that I liked. This is a chance to focus on one specific thing in agency life and at that moment, operations were where my heart was at. So, that’s where I’m at today. Still doing operations and absolutely loving it.

That is awesome. So, what’s one big takeaway you want listeners to get from this episode?

To not be afraid to pull the plug and to take the lead. There’s so much opportunity out there. Really hone in on what it is that you want to offer. Like a tight race, we narrowed everything down to just SEO services, and technical SEO services.

Yeah, I noticed that.

Narrow down that and what you are passionate about, then, by all means, go for it.

Right on, right on. Hey, Ashley, how can our listeners connect with you online if they choose to do so?

Certainly, you can find me on LinkedIn or you can find me on Twitter at Ashley Segura.

Right on. It’s been an absolute pleasure having you on the show. Thank you so much for being here.

Thank you so much for having me. This was really fun.

Right on. Right on. Have a great day.



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