Kyle Elliott is the career coach behind He is also an official member of an invitation-only Forbes coaches council and has been featured on Forbes, The Muse, Fast Company, and many other publications. His goal is simple: to help people find jobs they love. This help takes many forms ‒ career and life coaching, cover letters, interview prep, and a lot more.








In This Episode

Kyle Elliot left a full-time job to pursue a side hustle that kept eating more and more of his time. He created a business as a career coach helping people find jobs they love, teaching them to stand out by being authentic.

Topic Timeline:

1:15 Becoming an Entrepreneur

How a side hustle turned into a full-time business.

2:45 Breaking Rules on LinkedIn

Post on LinkedIn like you do on Facebook, with status updates 15 times a day.

4:00 Be Authentic and Real

Share quality content about careers, life or even Starbucks. Give free advice and share tips that are different.

5:00 Interviewing Personality

Be who you are; they will figure it out eventually.

6:00 Employee Responsibilities

Give staff members a target of bringing in enough revenue to cover their salary and then some.

7:20 Do What You Are Good At

Don’t waste time doing things you’re not good at. Stay within your specialty, and hire people who specialize in everything else.

8:30 Try Everything

LinkedIn ads may not have worked where Facebook ads and email marketing did. Have no regrets about things you could have tried.

9:15 Making Passive Income

Create courses so you aren’t always coaching one-on-one.

10:15 On Legacy

Take control of your own life and using that experience to help people, make an impact and change lives.

I like breaking rules. A lot of people who are LinkedIn experts say, ‘Okay, post on LinkedIn twice a week, three times a week.’ I post, like, 15 times a day.

– Kyle Elliott


Show Transcript:

LR: Welcome to Modern Ontrapreneur. Today we have Kyle Elliott, who is the career coach behind He is also an official member of an invitation-only Forbes coaches council, and has been featured on Forbes, The Muse, Fast Company, and many other publications. His goal is simple: to help people find jobs they love. This help takes many forms ‒ career and life coaching, cover letters, interview prep, and a lot more. Thank you so much for being on our podcast today.

KE: Yes, thank you so much for having me.

LR: We are here to talk more about your experience building a business than helping people get jobs, because our viewers are entrepreneurs who are starting a business of their own, like yourself. Tell me about how long you’ve been doing what you’re doing and the experience you’ve had getting to where you’re at today.

KE: Yeah, so I did career coaching on the side as a side hustle for about three and a half years. Then, a year ago in June, I quit my full time job in San Francisco, including free rent and a meal plan to do career coaching full time. Then, the last nine months it’s blown up. It went from me just doing it myself to now having three staff, so it’s really blown up pretty quickly, especially for just career coaching, which is a one-on-one business.

LR: Yeah, awesome. Congratulations. What was the thing that shifted or what level did you see that allowed you to take the leap from the side hustle to full time?

KE: Yeah, I was just getting more clients than I could handle. A lot of my business was from referrals, so I spent $0 marketing when I went from side hustle to doing a full time business, and then all of a sudden I was just getting all these referrals where I was doing 20 – 30 hours a week of coaching while also doing full time and I was like, “Okay, I have to either choose my full time job or do full time business,” and I decided to do full time business.

LR: Then it sounded like, once you decided to do full time, it blew up even faster. Is that right?

KE: Yeah, it blew up even faster.

LR: What caused that?

KE: A lot of it was LinkedIn. I’m big on LinkedIn, and every time I posted something on LinkedIn, I just had more people showing up and saying they wanted services. Then once I just put a few dollars into marketing, it would just come back even more. Every time I just ratcheted it up a little more, it just blew up even more.

LR: Uh huh, you make it sound easy. Tell me about your LinkedIn experience. You get on there, and you just hang out and, I don’t even know. I don’t use LinkedIn, so tell me about it.

KE: I like breaking rules. A lot of people who are LinkedIn experts say, “Okay, post on LinkedIn twice a week, three times a week.” I post, like, 15 times a day.

LR: Oh my gosh.

KE: I treat it like Twitter and just post all the time. If I have random thoughts, I put them on there.

LR: Okay, hold on, stop. Again, I’m not a LinkedIn expert at all, I don’t go on there. It just seems to me that the posting situation on LinkedIn is more like a blog post. Is that the thing you’re talking about, or is there another part of it that I’m not aware of?

KE: There’s blog posting on LinkedIn, you can write an article, and then there’s also status updates.

LR: Oh, status updates. That’s what you’re doing.

KE: Yeah, so I’m doing that 15 times a day sometimes.

LR: Oh my goodness, okay.

KE: People are like, “Oh, you can’t post all the time,” but I do it and people seek me out. They log into LinkedIn and look for my posts. People are reaching out saying, “I’ve never done that before. I don’t go on LinkedIn and look for one person,” but they’re doing that and looking for me, and they’re continually doing that. I’ve been getting thousands of followers every week just by posting that quality content, because people aren’t used to that on LinkedIn. They’re not used to getting free quality content, they’re used to paying for that through a course.

LR: Yeah. What are you posting?

KE: I’m just posting tips about careers. I’m also posting about life. I’m posting about Starbucks. I think people appreciate me just giving out this free advice, and then being authentic and real and sharing tips that are different than what they’re used to. I share, “Hey, when you go to an interview, bring a cup of coffee so then if you get nervous or you don’t know what to say, spill it on yourself and run out.” I just post stuff like that, and people aren’t used to that advice so I think they appreciate that.

It’s usually like, “Okay, if you go to an interview, you need to wear a tie, you need to do all this.” I like breaking down those rules and being like, “How about we try something different?” I give advice that people aren’t used to and I think that’s really resulted in some amazing results. There’s been some pushback here or there, usually from an older crowd, but a lot of people have really enjoyed that. It’s something different they haven’t seen before and people like something that’s different and unique.

LR: Sure, and it’s also, they’re resonating with you, and this is clearly a personality play. Right?

KE: Mm-hmm (affirmative).

LR: It’s you being authentic and kind of putting yourself out there, and people are just kind of like, “That’s the guy I want to learn something about.” Do you talk to people about how to be more authentic in their communication, in terms of interviews?

KE: Instead of going in there and being like, “Okay, I need to be professional,” whatever that means, just being authentic and answering questions authentically because they’re going to figure out who you are. It may be your first day on the job, it may be 90 days in, a year in, but they’re going to figure out who you are.

LR: Now, you then, sounds like pretty quickly made a leap from guy who was hustling to guy who was full timing to now guy who’s employing three people. Tell me about how you decided to take on, because I know personally that having that kind of overhead, being responsible for somebody’s paycheck, makes things a lot different. Right? You feel responsible and sort of burdened and almost scared in a certain way. It’s not just your rent you’ve got to deal with now, it’s somebody else’s. That’s a big leap to go from zero to one, and then from one to two and two to three. What gave you the confidence to make that investment?

KE: The money was definitely coming in, so that helped. I was able to secure my own rent in the Bay Area and all of that. Then also with my staff, I let them know and I was transparent from the beginning, “Okay, I plan to hire you, and then I want to be able to cover your salary plus some,” so I let them know from the beginning that was one of their measurable targets. I had very clear targets saying, “Okay, here’s how much you’re making. You have to be able to make that back plus some.”

One of my staff actually started her own agency recently helping people like me, and she’s going to help more people and entrepreneurs really make their own money back. I don’t remember her exact tagline, but it’s virtual assistants who help people cover their own salary plus some. That’s what I tell each of my staff that I brought on, and they have taken that under and said, “Okay, I’m going to do that. If I’m going to write an article and spend two hours on it and you pay me two hours, Kyle, I have to bring back 10 clients,” or whatever it is. They really enjoyed it and they’ve found it fun to not just be doing admin tasks but do sales and marketing and bring in new business and help clients.

LR: Interesting, so you’re creating kind of an entrepreneurial experience for your employees, it sounds like.

KE: Yeah, it’s really fun being able to mentor and coach them and help them grow and not just give them tasks that are tasks. “Okay, you’re going to do my calendar.” It’s so much more. It’s really helping them grow as business leaders.

LR: Wow, interesting. Okay, cool. If you could go back to maybe when you just first started, thinking about this side hustle, and give yourself a piece of advice that would have, I mean shoot like I said, you make it sound so simple, but if you could have made it even simpler, what would that piece of advice be?

KE: I think I would have hired staff sooner.

LR: Oh yeah?

KE: I definitely waited to hire staff or with my website for example, me and one of my assistants tried creating the website ourselves, and we’re like, “Oh, we can do that. It’s not that hard.” They have a plug and play or a cookie cutter, and I was like, “Mmm …” After spending several hours on it, and then her spending like 40 hours on it, we got it and we were like, “This is not good.” We wasted all that money, and then we had to hire a professional after all. I think really realizing what I’m good at sooner, and then everything else hiring other people for.

LR: Yeah, cool. What is it that you are good at?

KE: I’m really good at branding and helping people brand themselves. I’m really good at coaching people and helping them with that. I’m really good at leading people. Then, everything else I’m not really good at. My dad said I have very few talents, but the things I’m …

LR: Thanks dad.

KE: Thanks. The things I’m good at I’m really, really, really good at. It’s either, I’m an A-plus or I’m like, a D, and I’m okay with that. I focus on the A-plus, and then I hire other people for everything else, and it’s worked. Then I find other people who are A-pluses. One of my assistants is an A-plus at Facebook, so I let her do that.

LR: Yeah, awesome. Now, you talked about deciding it was time to actually invest in advertising, too. You put some dollars into LinkedIn ads?

KE: I tried LinkedIn ads, and they actually didn’t work. Facebook ads worked for me. That was the main place where I really saw a return on the investment. Some email marketing where I saw it. I tried magazine ads, nothing. I like trying a ton of different things, and then if it works I keep going with it; if it doesn’t work, oh well. It’s hard at first when you spend, like, two grand on magazine ads and you’re just starting out. You’re like, “That’s a lot of money.” Over time, I’ve learned to just try things, and it can’t hurt. I don’t want to regret it later and be like, “Oh, I wish I would have tried something.”

LR: You seem to be a natural. What is your kind of like, cutting edge right now? What are you learning about? What is the next hill you need to climb?

KE: I’m trying to make passive income. Right now, a lot of it is me having to coach people one-on-one or do workshops to make money. I just created a small little course, and I want to create more courses or do some group coaching, something where I can make more money and not have to just be coaching one-on-one. I think a lot of business owners want to do that, they don’t want to always be working. They want the business to be working for them. That’s kind of my next goal, and I’m trying to figure out how to do that exactly.

LR: Yeah. You think that, like, an online course is going to do that for you, and that you’ll be able to drive people to some kind of recurring income source that way?

KE: Exactly, exactly. I think annual recurring revenue or monthly recurring revenue is kind of where it’s at, but my background’s not in business so that’s something I’m trying to learn. I’m like, okay, maybe I need to hire a business coach for myself to help me with that.

LR: Man, you’re a young guy. Obviously, you have a whole career ahead of you, and normally I ask, “What is your legacy going to be?” Maybe it’s a little early for that. What is it all about? What motivates you to, apart from paying the rent, what motivates you to continue moving forward the way you have?

KE: I love helping people and I think when I help people, with a resume for example, it’s so much more than a resume. When someone says, “Hey, I got a job and I’m able to afford my kid’s college,” or, “I’m not going to lose my house because I was unemployed,” or someone recently reached out to me because they had, like, two months left to live here or they had to leave because of their visa, and they said, “I’m investing $400 in a resume, and if I don’t get a job in the next two months I have to move back to my home country.”

I’m their last chance, sometimes, and I think that’s really exciting when they’re able to work with me and get a job and stay in the US because they worked with me and I was able to help them on that journey. I think that impact, that me working with them for an hour or two hours results in them changing their life, that really impacts their life. I think that’s what’s exciting.

LR: That’s amazing. What do you feel like it means to be an entrepreneur today? What does it mean to be a modern entrepreneur?

KE: I think it’s really just taking control of your own life, and then being able to use your power and your experience to help other people. I think that’s what it really is all about. Any business has to do with people at the end of the day and helping them.

LR: Awesome, hey Kyle, this has been so great. Thank you so much for joining us. Would you sign our wall?

KE: Yes, absolutely. Thank you for having me.

LR: Awesome, that was so good.

Want more Modern Ontrapreneur Podcast?

Check out the previous episode featuring keynote speaker and best-selling author Carla Johnson.

About Wilson Kwan
Wilson Kwan, Ontraport's Traffic Manager, is from California's Bay Area and received degrees in Asian American Studies and Statistics from UCSB. Wilson has enjoyed many roles and apprenticeships at Ontraport in customer support, tech support, email delivery and marketing. He finds enjoyment in experiencing new cultures and adventures, but is also very much devoted to his hometown basketball team and future dynasty, the Golden State Warriors.