From Rock Star Dreams to Business Success: Tarra Stubbins’ Journey 🚀

Martin Rowinski (00:00.75)
Welcome to another episode of Boardsi Leadership Talks podcast, where we delve into the minds of industry leaders to uncover their secrets to success. I’m your host, Martin Rowinski CEO and co -founder of Boardsi Our mission is to connect companies with top tier executives, talent and foster leadership excellence. Today, we have a very special guest who brings a unique perspective on goal setting, time management,

and entrepreneurship. Please join me in welcoming Tarra Stubbins, a renowned celebrity assistant with over 20 years of experience and founder of two multimillion dollar businesses. Tarra, it’s a pleasure to have you on the show.

Tarra (00:47.161)
Thanks so much for having me. I’m excited to chat about all the things today.

Martin Rowinski (00:52.398)
Awesome. Well, I’m excited and you have an incredibly diverse background, especially as a celebrity assistant and also obviously entrepreneur. Can you share with us how you got started in your career and what led you to work with some of the world’s most famous individuals?

Tarra (01:11.993)
Yeah, for sure. So it actually started when I was really little. So when I was about six, seven, eight years old, I had a t -shirt that said, remember me, I’m going to be a star. And I wore that shirt everywhere to the point where it disintegrated. I really wish I still had it today. It’s pretty comfy. But the problem was, is in my very like little undeveloped mind, I always thought that being a star was being a rock star.

So singing, dancing, performing, playing a musical instrument. And the problem was, is that I have very little musical talent. I try to play instruments, but they sound like dying animals. I really love music and get a lot out of listening to it and being surrounded by music, but I…

Martin Rowinski (01:57.006)
You

Tarra (02:08.089)
just have no talent at all when it comes to anything musical related. So when I was younger, I thought, well, that’s it. I’m never going to achieve my dream. I’m going to just throw it out. I’m just going to be this like useless human being. But for some reason, and I tell this story a lot, something inside of me told me not to throw away the entire dream and to hold on to a little tiny percentage of it.

And so I did, I threw away most of it, but when those kind of pivotal moments in life came up, you know, when you have to make those like decisions, am I gonna go this way or am I gonna go this way? That’s when I would remember, yeah, I wanted to be a rock star. Still can’t dance, still can’t sing, still can’t play this, you know, guitar, but maybe I should make kind of this decision.

And in all that craziness, it kind of led me to not necessarily being on the stage performing and singing and dancing, but being behind the scenes supporting some of the world’s most successful people. And, you know, it kind of sounds easy when I say it, I just kind of had a dream and went with it. But obviously I started out, you know,

very small doing the grunt work, getting coffees and cleaning gross dressing rooms and gross tour buses and living in horrible, ugly hotel rooms and all of that sort of thing. But from the very moment that I kind of dove into that world, I knew that it was where I wanted to be and where it made me the happiest.

And that’s why I continued on. And I think a lot of times people will continue on in a dream because it was a dream, but it’s not really making them happy, but they’re like, well, this is my dream. So I’m going to keep doing it. And then they’re not as successful, but because it was my dream and I absolutely loved every minute of it, even, you know, the smallest little, you know, getting coffees or cleaning up after discussing rock stars.

Martin Rowinski (04:16.75)
you

Tarra (04:18.361)
I was happy and that’s how I could kind of climb up the scale.

Martin Rowinski (04:23.214)
That’s awesome. That’s funny. You sound just like my daughter. She used to always say, I’m going to be famous one day. And she’s in that world too. She’s in her twenties and she does social media for DJs.

Tarra (04:30.009)
Yeah!

Tarra (04:40.121)
I love it. Yeah, so and it shows that you don’t necessarily have to be the DJ up on the stage There’s so many different opportunities and I feel like if you are going to be successful You know it and you don’t have to fight it. You just know within you that this is what’s gonna happen

Martin Rowinski (04:59.15)
Absolutely. Well, you you transition. So I’m curious what inspired you to transition from being a celebrity assistant to actually launching your own business or businesses.

Tarra (05:11.929)
Yeah, so it’s actually interesting because I was so fascinated with why these rock stars. So I obviously had the opportunity to work with some people like Mick Jagger and the Rolling Stones and Lady Gaga and Sandra Bullock. And I was always fascinated as I was embedded in their lives of why them.

why did they seem to win this, you know, lottery of life to be so successful and have all this, you know, talent and why not me? And so because I was so fascinated in what they did on their day to day basis to build success and maintain success, I was like a sponge and you know, everything that they were doing and trying to figure out like, what is this kind of secret

formula. And I had a bit of a aha moment one day when I was helping a client with one of a crazy rock star with one of his crazy requests. And he always wanted his toothbrush to be sanitized in hotel dishwashers every time it came out of a suitcase. So

I don’t know, people always ask me, did I do it? Of course I did it. I never thought twice about it. And people always ask me, well, why didn’t you just throw out his toothbrush? I don’t know. I never asked these questions. I just went ahead and did it. So I was standing there one time trying to communicate in a language that I didn’t speak that to these hotel staff that I had to put this toothbrush in the dishwasher. And I just remember standing there going, this is not going very well at all.

and thinking, I remember the exact moment where the thought came into my head that there’s gotta be more to life than this. And it was kind of my like moment of, I really love helping people, but maybe not this anymore. And I just kind of wanted to help more than one crazy rock star at a time. And so I came off the road and I decided that that’s…

Martin Rowinski (07:08.43)
Ha ha.

Tarra (07:26.937)
what I was going to try and do. And I opened up my first business in 2007 with zero business background at all. I had no experience. It was this dirty roadie who like lived with the circus, as I like to say. And I didn’t, I didn’t understand. I remember trying to put ads in back then it was the yellow pages and people were like, why are you doing that? I’m like, I don’t know. I feel like this is what I have to do. And obviously not going anywhere.

So, but then when I was struggling, I remembered, yeah, I have this whole information of how these people have become a success. And this is what I’m going to use to leverage my day to day and build my business. And that’s what I did. And then I was able to build another business on top of it, being able to leverage the same principles that I witnessed on the day to day.

Martin Rowinski (08:24.27)
That’s awesome. So before I get to the next question, just curious, did you ever stay at the Phoenix Hotel in San Francisco?

Tarra (08:31.801)
Of course I did. Yes. Why?

Martin Rowinski (08:33.262)
That’s funny. I know that guy that used to own it. He sold all his boutique hotels, but pretty good friends with him.

Tarra (08:42.841)
trying to remember his name. I probably even knew it. It’s been a while, so.

Martin Rowinski (08:49.23)
Yeah, and depending on how long ago, I know he sold it a while ago, but he’s the guy that restored it from being a really crappy hourly hotel to being, you know, used by a lot of stars and it became known for that. So he kind of told us that story. So it was kind of cool. But working with people like, I mean, Brents and Lady Gaga, you named a lot of names there.

Tarra (09:00.249)
Yeah, yes.

Martin Rowinski (09:14.958)
What are some of the key goals, setting and time management strategies you’ve learned from them?

Tarra (09:21.689)
Yeah, so that’s a bit of a loaded question and I can go on for three hours on all of that. So I will try to sum it up as best I can. But basically it comes down to three principles that I was able to kind of witness and put into practice myself. And so I know that it absolutely works. And it’s all common sense. So it’s actually really interesting.

Martin Rowinski (09:25.838)
Ha ha ha!

Tarra (09:44.313)
When I started my business, you know, with no business background, what did I do? What does everybody do? They Google it, you know, how to run a successful business. And in 2007, Google wasn’t as sophisticated. There was no chat GPT to help me, you know, make a business plan. And it came up with two things that I’m pretty sure probably will tell you today. It’s all kind of very generic information. And it told me to hustle.

which I absolutely hated because I didn’t understand what they meant. I wanted something that was tactical, you know, send 100 emails a day or talk to 26 people a day or whatever it is and hustle. I couldn’t grasp onto that concept of being busy just to be busy.

The other thing it told me was to network. And that was something that I was like, yeah, I have this amazing network of people. Why am I not leveraging it? So that’s something that I still hold very close and very true for anybody who’s struggling is make sure that you leverage your network. And I truly believe that you are only as good and as powerful and as successful as your network. So I think it can only get you so far.

So make sure that you surround yourself with the right type of people. And we hear that a lot too. Again, nothing I’m gonna say today is anything that, you know, different or that we haven’t heard. It’s just actually bringing the concepts together and not overcomplicating things. So one, leveraging your network is absolutely probably the most important. And then the second is I started realizing that these successful people

even the athletes that I’ve been able to support, the professional athletes, they are the most focused and determined individuals I have ever met in my entire life. And they are extremely obsessed with their goal. So they set a goal and they focus on that goal. And you know, a lot of times it’s not

Tarra (11:57.689)
acceptable or available, for, you know, kind of the average person to be able to focus and obsess on a goal as much as they do. But I think it determines, and it depends on how high you want to go and how successful you want to go and what, how big your goal is of how, to determine the amount of focus that you have to strive for. obviously,

You know, the Olympics are coming up right now and we see all the athletes and the trials and all we hear their stories of, you know, the four years that they’ve been putting into focusing every single day, every single moment on the gold or being the fastest or jumping the highest or, you know, whatever it is. So, making sure to absolutely set a really strategic and big goal.

And then being able to focus on that and become truly obsessed with that goal is also key. It’s interesting because a lot of times people will read books from the new habit forming books or time management books or the book from this new famous CEO.

which is great. I love that they’re putting it out there, but then they come back to me and they’ll say, well, Tarra, I tried exactly to copy these people’s morning routines and I’m still not as successful as them. I’m not making $3 million this hour. And it’s interesting because their morning routines are really great for them, but not necessarily for me or you or any of the listeners because we’re all our own individual people.

and we all have our own individual lives going on and we’re all in kind of a state of where we are in achieving our goals. So being able to, you know, get up at 4 a and meditate and exercise and drink a smoothie or whatever it is that, you know, is making these people successful isn’t necessarily what’s gonna make everyone successful. But the common thread between all those books and what everybody talks about if you listen to

Tarra (14:17.497)
Every single motivational speaker or anybody that talks about setting goals and achieving them is having a very, very clear concept of your goal and becoming incredibly focused on that.

Martin Rowinski (14:18.766)
Thank you.

Martin Rowinski (14:31.438)
Yeah, I always say have a mission, vision, and values and stand by him and always move towards him.

Tarra (14:38.457)
Yeah, and it’s interesting too, because I talk to and I help a lot of people through goal coaching and setting and being accountable for their goals. And you know, it’s so easy for us to sit here and talk about it. And for, you know, my incredibly famous celebrity clients to achieve their goals because they have help. You know, they can put money behind it.

It’s easy for me to sit here and say, all you have to do is focus and set your goal and you’re going to be successful. But actually doing it is another thing. And so the other kind of skill technique that I witnessed that helped all these successful people become successful was that they create their own motivation. So they’re not sitting back for that lightning strike moment. They are determined.

They are, as I said, they’re focused and they’re not letting any of those excuses that we always make up of, I’m too tired or I’m not smart enough, I’m not rich enough, I don’t have a sob story, life story behind me, I can’t do it, whatever it is. And it’s actually interesting that 80 % of the reasons why we can’t do things are all those internal triggers that we make up.

basically. And so if we can just get past those 80 % triggers, then, you know, there’s really nothing stopping us. And so there is no trick, there is no hack, there is no app. It’s just really you being able to just, as I always say, just do the thing we know what we need to do. And it’s just being able to sit down and do it.

Martin Rowinski (16:27.246)
Yep, get it done. And speaking of the guy that owned Phoenix Hotel, he’s also a great author now. And his name, by the way, is Chip Conley, if you knew him. So.

Tarra (16:39.961)
I don’t think I don’t think so maybe but the name rings a bell maybe I’ve read his books

Martin Rowinski (16:43.63)
Okay, I take it easy group, you focus on helping overworked founders and CEOs build scalable companies. What are some of the common pitfalls that startups face and how can they avoid them? I mean, they can’t really avoid them, but help them.

Tarra (17:05.209)
No. Right. So as entrepreneurs, everyone, even myself, we are all prone to the shiny thing. So I would say that every single entrepreneur and founder that I help, it is again, helping them stay focused. So let’s set very clear goals, whether you’re using the OKR system, KPI system.

US system, you know, whatever it is, please use one of them, set your goals and make sure that you and your team are tracking the priorities of those goals daily. So a lot of founders, they again, they get stuck in their own way. So there’s so many things to do, I get it. And a lot of us don’t have the resources to be able to outsource a lot of those things. So they fall on our plates as as business owners and founders.

And again, I get it. But it’s deciding what task is an absolute priority for your end goal. And I always like to call them, what is going to move the needle? What are needle moving tasks today? Sure, renewing my passport and making my kid’s dentist appointment and maybe fixing my flat tire is extremely important.

But are those things going to move the needle on my big goal? Probably not, unless your big goal is to travel and you need your passport, but probably not. Okay, so let’s make sure that today, if I don’t do anything else, if I get sidetracked, I do one thing that is going to achieve or move the needle on the goal. And then I can concentrate on all those busy tasks.

Martin Rowinski (18:42.35)
You

Tarra (18:58.009)
so I think it’s like prioritizing that a lot of people get confused with and they, they think that like life tasks are tasks that a hundred percent need to be done, on a day -to -day basis. Another thing that I help founders with is, they’re, you know, just general calendar management. So again, a lot of us have our own systems. we’ve heard of time blocking. We’ve heard of, you know, there’s a million different ways to run a calendar.

But again, I think it’s like setting up systems and sticking to them and not over complicating things. So again, there’s a million apps out there. And if you’re an app person and they help you absolutely go for it. But I see a lot of people, especially CEOs, even ones running really large companies who will get bogged down in the, well, let’s create this system. And then this system feeds into this system. And then this

And we’re not actually concentrating on the tasks that are moving the needle. We’re concentrating on these confusing systems that we’re now angry that the team isn’t picking up, where it could just literally be three tasks in my calendar and I’m done type thing. So not over complicating things, making sure that you use a system that works for you, but continue to use it.

and really making sure that you’re just focusing on those needle moving tasks on a day -to -day basis.

Martin Rowinski (20:30.83)
Yeah, like I like to say the old saying because I’m an old guy. Keep it simple.

Tarra (20:35.641)
Keep it simple. Absolutely. And yeah, and I really think that now, you know, with technology and all these fun apps, like I love a good productivity app and I will get in the weeds and you know, I will go down all these rabbit holes, you know, when a new one comes out. But then I go back to my exact same system of putting my tasks on my calendar because I know exactly when I’m going to do them and I can see them all laying out in front of me.

And I don’t want to, you know, click between all of these different tasks. And I’m old school too. I love a good list. I will write lists for the grocery store on a piece of paper, not in my phone. I love a good list. But again, I think that to -do lists are another thing that we get a little sidetracked on. And I really believe that to -do lists, I always like to say kind of beat us up as human beings because they’re never ending.

And we can never be successful. We know we’ll write a to do list for the day we go out into the world and you know, life happens and then we come back and like, have we done anything on our to do list and then we feel horrible about ourselves. So lists are great, not necessarily to do lists.

Martin Rowinski (21:44.91)
You

Martin Rowinski (21:51.406)
Awesome. So I know your mission is to help others set goals that create the life that they want to live. And a quote coming from you. How do you encourage and guide individuals to become the quote, Beyonce, Taylor Swift or Drake of their own lives? Obviously, I can never be Taylor Swift, but.

Tarra (22:13.689)
Yeah, so you could, anyone can for sure.

Martin Rowinski (22:19.982)
Not exactly Taylor Swift.

Tarra (22:23.833)
I’m sure you could. It’s all again, it’s all about setting the right goals for you as an individual. So if we go back to like my original goal, I always thought that I wanted to be, you know, the actual Taylor Swift. But you know, maybe you’re not that rock star or you know, that massive celebrity or maybe a celebrity status, you don’t want it at all, which is, you know, a lot of people would could just, you know, absolutely leave that out of their their goals.

But is it, you know, are you being the Beyonce of, or the best, you know, person that you could be in your parenting group or the best darn mother or father that you can be, or, you know, the best volunteer or the best CEO in your, you know, class of, you know, your group of whatever you’re running or, you know, whatever it is, are you being

the best person that you can possibly be on a day -to -day basis. And you know, us as leaders and us as CEOs and founders, we go through a lot through the day. You know, I run two companies. Sometimes I get sued. Sometimes I have cranky client. A lot of times I have cranky clients or cranky staff. And it’s always about, you know, okay, that can be, I feel bad at the end of the day. Like that was a bad day, but

Was it a bad day or was it a bad one thing that happened? And then I did get all these deliverables out and I’m still living to achieve my big goal and I’m still being able to push the needle forward. Okay, yes. Okay, so maybe it wasn’t as bad of a day as it seemed.

Again, I’m not naive. I know a lot of us have really, really bad days, especially when running companies. And it’s just kind of par for the course and something that kind of sets us apart from other people, you know, if you can continue and if you can kind of brush off those bad days and, and, you know, continue on to the next step.

Martin Rowinski (24:31.374)
Awesome. Well, switching gears a little bit, I’m a huge, huge person when it comes to executive branding. I believe it throughout. I mean, it’s so important. And I know you’ve been featured in numerous media outlets and you’ve shared your expertise through keynote addresses. But how has your media presence and public speaking experience contributed to your professional growth?

Tarra (25:01.465)
Yeah, so for me, it’s it’s actually about personally, I’ve always said that I have been put on this planet to help others succeed. And I truly know and understand that I am the happiest when I know that I’ve been able to do one thing to help somebody else achieve their goals, or get closer to their goals. So me sharing my story and trying to help

motivate people who kind of feel stuck and share, you know, that if I can do it, anybody can do it kind of scenarios and also shared the behind the scenes secrets that I’ve been able to learn from these really successful people. You know, I have stories for days that I love to share in my longer keynotes and

Being able to do that and kind of, I always felt that I was like holding on to this like massive secret of success and I just wanted to get it out there and I just wanted to share it as much as I could so I could really, as I said, like help as many people as I possibly can achieve their goals. So for me, it’s not necessarily about branding or about going out there and getting new clients. Obviously that is wonderful and nice.

obviously about building my network because I am a huge believer in that. But it really truly comes from a place of me just wanting to help as many people as I can achieve their goals and as we were saying become the Beyonce, Taylor Swift or Drake of their own lives.

Martin Rowinski (26:35.054)
The funny thing is Tarra, the more you give, the more you get back.

Tarra (26:39.417)
It’s very, very true karma. Karma is definitely working for us or against us depending on how you’re living your life.

Martin Rowinski (26:42.094)
Yep.

Martin Rowinski (26:48.014)
Any tips for entrepreneurs looking to build their personal brand and gain some exposure?

Tarra (26:57.945)
Yeah, so people ask me this a lot and I have the, you know, kind of wonderful background of being able to drop some celebrity stories. So the press and everyone kind of come to me. So I never really had to fight to get out there. However, my, what I do tell people is that make sure you’re able to tell your own unique story. As we, and I know, again, we’ve heard this a lot. It’s just, you know, making sure that you understand and

actually set time and commitment to be able to understand your own unique story. And we were talking about, you know, making sure that you understand your kind of why and your big goals and weaving those into your unique story is also really helpful as well. Being as authentic as possible. And, you know, as we were talking about the books with

CEOs and everyone who writes them and then us trying to kind of copy along Please don’t copy anyone else’s keynotes or inspirational talks or try to be like somebody else You know, it’s it’s so interesting these days the hermosis so Alex, you know, he’s taking off He’s he’s everywhere and then you see that every single YouTube, you know short looks exactly like him and you can buy the fonts that go

that look exactly like Alex’s and you know, it’s great, yes, it works for him. But it’s not going to work for everyone if you try to copy along exactly what he’s doing. I love what he does. I love what he talks about and I love that he’s trying to help, again, as many people as he can achieve their goals. Let’s just be our own unique person and trying to accomplish them.

Martin Rowinski (28:23.118)
You

Tarra (28:49.913)
Again, you’ve heard me say that nothing I’m going to say today is unique. It’s just kind of the way that I package it and be able to tell stories of my background and how I’ve been able to experience what works for the majority of successful people around me. So don’t be shy that you might be copying little things, but again, turn them around into what is true to you and you’ll go so much farther.

than trying to be a person that you’re not.

Martin Rowinski (29:21.262)
Absolutely, be original. Just like we were born. So as we wrap up, any final piece of advice you would like to leave with our listeners?

Tarra (29:24.825)
You got it. You summed it up in one word. I took five minutes to say the exact thing.

Tarra (29:38.681)
So I am a big believer in the word multitasking and how it should be erased from the English language. Again, going back to me first Googling how to be a successful business owner and seeing the word hustle. My tagline actually for take it easy is quit the cult of busy because a lot of us now I’m not saying that we are not going to be busy and that you don’t have to be.

Martin Rowinski (29:48.59)
You

Tarra (30:07.577)
extremely busy to be successful. Sometimes we have to make a lot of sacrifices and work long hours and really, really hard. I absolutely understand. But there’s no point in being busy just to say that I’ve hustled today or I was busier than you today or I worked longer hours than you today, making sure that you are working hard on your goals and what those needle moving tasks that we talked about are.

and not necessarily just being busy to be busy to try and outperform somebody else. Again, being your own unique person and following your own unique goals. So please let’s not multitask, let’s not hustle. Let’s try to quit the cult of being busy just to be busy and actually try to achieve our own goals and stay focused on them as well.

Martin Rowinski (30:58.51)
Or like, I like to summarize that, I’d rather be productive than busy any day.

Tarra (31:04.441)
Absolutely, and there’s a huge, huge difference in it. It’s actually, in my opinion, why we’re so tired as a society, because we’re constantly switching context, context switching between our phones and social media or the different feeds to, now I have to send an email. now I have to jump on a Zoom call or, now I have to get in my car and drive to this meeting or, now I’m gonna look at my phone again.

You know, all this context switching is really making us incredibly tired because we’re not, our human brains can only think of one thing at a time. So we’re actually think we might be doing two or three things at once, but we’re just switching back and forth really quickly or more slowly as we get more and more tired.

Martin Rowinski (31:53.55)
Yeah, absolutely. How can our audience connect with you and learn more about your work?

Tarra (31:59.801)
Yeah, so my website or my business is takeiteasygroup .com. I have a personal website, Tarra with two R’s, stubbins .com. And on socials, I’m Tarra’s Time.

Martin Rowinski (32:15.118)
Awesome. Thank you, Tarra, for sharing your incredible insights and experiences with us today. It’s been a pleasure having you on the show. To our listeners, thank you for tuning in. Stay tuned for more episodes featuring industry leaders who are shaping the future of business and leadership. Thank you, Tarra.

Tarra (32:34.521)
Thank you.