When you need to be inspired as an entrepreneur…

January 23, 2022

I was GOING to start this post off by telling you my story.  BUT, my story is LITERALLY the story of every single small business owner in the history of small business owners. 

I launched my business with big dreams 5 years ago...

I changed that dream, pivoted my message, and found my new audience at LEAST three different times over that 5 years...

I had moments of being on cloud nine...literally cotton candy and unicorns...

And I've had days of being curled up in the fetal position, not knowing how to take the next step.  

As we move forward with this SERIOUSLY kick ass blog post, just know...I've been there!  And I totally expect to be there again!! Owning your own business will NEVER (let me repeat that...NEEEEEVEEEEER) be easy.  

You'll ALWAYS have problems, and your job as an entrepreneur will ALWAYS be to solve those problems.  Whether that's learning a new program or tool because you're diving into a new adventure....or you're hiring a new team member because you don't know HOW to solve your problem.  (Hint...that's still problem solving. Good job!) 

Being an entrepreneur isn't learning how to create a business...it's problem solving.  Simple as that...day in and day out.

But...that doesn't mean you don't need a pick me up

Recently, I've become OBSESSED...no LITERALLY OBSESSED with YouTube.  (I know...I know..."Welcome to ten years ago, Terra!".  *sigh*  

My only excuse?  I've been SO hyper focused on other areas of the biz for the last five years, that there was no room for YouTube, until I was ready for it. 

Baby, I'm READY for it!! 

So, for this post, I want to give you a list of my top ten tubers to watch right now for a small business pick me up.  They will LITERALLY strong arm you out of your fetal position on the couch, get you hyped to ACTUALLY put on human clothes (I'm talking to you, chick in your unicorn onesy that you haven't taken off in a week), and will EVEN get you to on the road to meeting those balanced life goals. 

So...let's jump in!!! 

the most inspiring small business youtubers on the youtubes

This is NOT just any list of Business YouTubers.  This is a list of YouTubers that are actually SHOWING their work. (Thank you Mr. Leshin from grade 7 math class...). 

MOST of these guys are vloggers.  They'll take you behind the scenes of their work days, strategy sessions, organization, and more.  What inspires ME isn't just hearing someone tell me what should be doing...but seeing them take the action as well. 

Lilly Singh - SuperWoman Vlogs: 

In the last two weeks, I've asked EVERYONE and their mother if they've "Ever heard of Superwoman on YouTube...". 

Apparently, I'm new to her game, but DAMN do I love it! 

Lilly Sing, A.K.A. Superwoman, is a comedian and sketch artist on YouTube. More than that, though...she is a Hustler (capital H) and hosts a DAILY vlog that shows you behind the scenes of her multi-million dollar (and SO down to earth) business. 

I recommend, specifically, binging her "best of the vlog" list!  With five years of vlogs, you'll see her state her dreams, achieve her dreams (oh, hello Dwayne "The Rock" Johnson and a Tesla), and make some serious lady business history. 

Casey Neistat:

World, meet my new husband. (Don't tell Josh about my secret life.) 

I...love...this...man. I love his drive. I love his curiosity.  But more than anything...I love his kindness.  This week, I heard an interview with Gary Vee (also an inspirational dude) that really talked about "drive" in a sort of negative way.  He said that if you haven't made it yet, you suck.  You aren't working hard enough. 

That might work for some folks...but not for me. Casey, in the same week, gave an interview talking about about learning to recognize the need to pivots...for recognizing that "feeling like a failure" is completely different than actually BEING a failure.  He said that if you're still putting skin in the game...you're more successful that most at life. 

Guys...just...all the love. He has AMAZING vids on his channel, but I recommend his vlog for some serious motivation!! 

Peter McKinnon -

I was a photographer for a long time...and although I don't pick up the portrait camera much anymore...I'm still more inspired by imagery and video than EVER.  It's something I miss dearly.  (Yay vlogging!!!  I feel like I'm getting back!!) 

When I found Peter McKinnon a few years ago, I was mesmerized by his "cool" way of teaching, his adventures, and his AMAZING videography.  

Two years later...the man still gots it. 

For inspiration on tech and just...wow...video, this man is your one stop shop. Although he doesn't post daily, his vlogs are ALSO a great window into his behind the scenes processes with shoots and just...fun

The Anna Edit - 

Let's change the pace just a little, shall we?

Anna Newton is a small business bombshell, with a TOTALLY different speed.  The daily life of this British business owner consists of organization, make-up, health, friends, family and...you guessed it...vlogging. 

So, why is she such an inspiration? 

In her vlog, she'll take you behind the scenes of working with larger brands, endorsements, writing her first ever book (bought it!!! It's amazing!! I feel so organized!!), and so much more.  She focuses more on the balance of life and business...which, incidentally, is her business. 

For a breath of fresh air, and to feel like you're slowing things down just a tad, Anna is your gal. 

Behind the Brand with Bryan Elliott -

Have you EVER wanted to take a sneak peak into the workings of some of your favorite brands? (ME TOO!!  Ps...this is also why I love shows like "The Profit" with Marcus Lemonis.) 

In "Behind the Brand" Bryan Elliott takes you on a tour through the inner workings of the brains of folks like Casey Neistat...lol, Simon Sinek, Seth Godin and Demi Lovato (she's a brand too!).  It also goes behind the scenes of brands like Toms shoes, Paramore, SoulCycle, Hootsuite, PatFlynn (OMG!), and hundreds more. 

Sure...these might be the beautiful beasts of business, but Bryan helps them become relatable.  

To tackle THIS channel, I recommend just pouring through the "Most Popular" list

Amy Landino - 

What is there to say about Amy Landino?

One word...strong. 

I've been a fan of Amy since her Schmittauer days...and have loved every second.  Through moving, marriage, growth, and loss in 2018, she's showed the digital world how to keep moving forward with strength and honesty. 

If you're looking to launch your own YouTube channel OR simply get your small business head on straight...Amy is a Swiss Army knife you'll want to keep in your back pocket. 

I recommend just tackling her channel from the uploads list.  She's a grab bag of inspiration with every video! 

Simone Giertz -

Robots are awesome to begin with...but SHITTY robots are even better!!! 

A few years ago, Simone Giertz began making completely pointless, but adorable robots.  (My personal favorites are the Soup Robot and the Applause Machine).  With humor, and some fun behind the scenes vlogs, she's set out to inspire all of the "women nerds of the world" (ok...and a ton of men too...Josh introduced me to her channel a few years ago!), that you CAN.  

In 2018, her adventures took a serious (but it's Simone...so "serious" will always involve a few puns) turn when she developed a benign brain tumor.  (Unfortunately, she announced this week that Brian (the tumor) back).  

For inspiration and "OMG IT HURTS" laughter...Simone is a daily go-to. 

Trena Little -

Trena is one of my new loves on the YouTubes!!  Yes...she has a vlog, but more importantly, she (in the most adorable and friendly way possible) invites you into her office...and PERSONALLY walks you through launching your YouTube channel. 

She's generally on rotation on my TV...and I GENERALLY get ZERO work done when she pops up. Her tips, tricks and conversation style always have me looking up, updating something on my channel, or getting ideas for brainstorming and organizing new content. 

If you're just about to start YOUR first YouTube channel, I recommend starting out with her "start your channel" list

Terra Dawn - Uncork Your Dork:


I would be SILLY not to throw my name in here is well!! In 2019, I started vlogging.  Yep...I'm still learning how to do it well, but remember EARLIER in this post where I told you that "learning" is ALWAYS going to be the name of the small business game? 

I am SO excited to see what it looks like a year from now!! 

In the vlogs, I'll walk you through my daily agenda (LET'S GET STUFF DONE!!), my thought process behind the decisions I make, my excitement...and my disspointments.  

All of it, baby!! 

In addition to the vlogs, I also throw up a video every Tuesday that will walk you through creating your very OWN subscription product!! 

And as a bonus...

Gary Vee:

Ok...so I ALMOST didn't include Gary in this list. (I know...he'll be heartbroken when he finds out.) WHY was I thinking of leaving out THE ultimate business blogger of all time?? 

Primarily, because this list was supposed to be a inspirational list. Generally...I love this man.  He's like a drill sergeant, screaming "GET UP YOU MAGGOT, OR YOU WON'T BE WORTH THE CHIPOTLE BURRITO YOU'RE CURRENTLY SHOVING IN YOUR PIE HOLE!!" 


Some days, it's what an entrepreneur needs (hence he's being included)...but most days, for me at least, it's actually depressing.  In Gary's most recent video, he says blatantly, if you've been trying for three years and haven't made it in business...you suck. 

I'm not breaking up with the man...but I don't think we'll be getting hitched any time soon. 

the most inspiring small business ebooks you should be reading right now...

I've been a book worm since birth...but I'll be the first to admit, in this crazy time known as "adulthood" (the quotes are appropriate if you know me) that I have VERY few minutes in the day to just sit and read.  

I DO, however, have a shit ton of time to sit and LISTEN!! So, between the vlogs on the TV while I work...and the audio books I devour in a 7 day stretch, my inspiration over-floweth.  

SO, in this section, we are tackling some of my FAVORITE books (the media format is up to you). Again, these are NOT just "how to start a business books"...these are books that ACTIVELY take you through the process of owning your small (or large) empire.

How to Be a Bawse - Lilly Singh:


She's a BAWSE, so YES!! Always yes!!! 

In this auto-biography, Lilly will kick your butt into high gear as she walks you through her experience planning world tours, becoming a celebrity vlogger, working with celebrities like The Rock, Will Smith, Selena Gomez (and literally hundreds more), and working through the depression that a TON of small business owners know and HATE. 

I listened to this book read by the author...and it was AMAZE-BALLS. 

"Rhinoceros Success" - Scott Alexander:

THIS, is one of the cheesiest business books you'll ever read.  But there is LITERALLY no way I can overstate it's value. 

Since reading this book a year ago, Rhino's (and an amazing mind set) have been popping up ALL over the place in my life.  

Rhinoceros Success isn't about "how to succeed", it's about just. plain. SUCCEEDING.  

This book (in any media) will take you 1-2 hours to get through.  It's a small book that packs a BIG ol' cheesy punch. 

"You're Never Weird On the Internet" - Felicia Day:

The Guild (seen in the background of a few of the vlogs this past winter) is a YouTube series I've been a fan of since it's inception in 2004.  SO...by association, I've been a fan of it's nerdy creator, Felicia Day for a while as well!! 

In her book (with a forward by Joss Whedon....eeeeeee!) Felicia walks readers through her journey from shy, homeschooled nerd...to internet cool cat...to the center of one of the biggest feminist controversies of the interwebs.  

The audio book is read by Felicia herself, so I'd recommend tackling this one with media you're comfy with! 

"She Means Business" - Carrie Green:

SHE is not kidding!! I'm not going to lie...I've been in business for a while, and I THOUGHT this book would be a little too 101 for me.  But last year...I got hit with a month long depression (my longest bout yet)...and this book is what pulled me through. 

It's not just a book of sound business advice, it's a compass to loving what you do.  This book DOES appeal more to women, but the advice and love could be for ANY entrepreneur. 

This is a quick read, but I would recommend hearing it directly through the voice of author.  You can grab the audio book via audible! 

"You Are a Badass" - Jen Sincero:

Alright...you've had your "sweet nudge" with Carrie Green's book, but now you're ready for a little kick in the ass, no punches held, tough love?  

Entre Jen Sincero.  

There are a few books in her series, but I HIGHLY recommend you start with "You Are a Badass". This book/memoire, will help you STOP doubting who you REALLY are on the inside...and learn to embrace it. (Not to mention, make money from it.) 

Grab this one in all the mediums!! 

"The One Thing" - Gary Keller:

Gary Keller changed my life. 

Before "The One Thing"...my life consisted of "All the Things" + confusion, unfocused determination, and stall in growth. 

The second I got CRYSTAL clear on my one thing (LITERALLY THE SECOND), my business began to take a turn.  I started feeling confident, seeing growth, and even better...seeing those sales. 

Although I read this one on my iPad, I can vouch for the audio book as well!!!

Just...make this your one thing until after you read it!! Then get a new one thing.  0_0

"The Bullet Journal Method" - Ryder Carroll:

I'm not gonna lie...this book is amazing BUT, it's not a game changer? 

Why?  Because Ryder Carroll (the amazing man that he is) has made it SUPER easy to implement the bullet journal method simply by watching his 101 video. (Plus, I mean, the thousands of Bujo videos available on the YouTubes.)

BUT, because he's been so generous (and the book REALLY is great), I recommend supporting his work with a purchase of the book...OR an official Bullet Journal notebook! 

The Bullet Journal is a new (super cheap...and SUPER maleable) method of keeping your agenda, journals, notes, and logs all in one place.  

No more organizing your life in 10 places!!!!  

"The Essential Habits of 6-Figure Bloggers" - Sally Miller:

As a kid, you're asked "What do you want to be when you grow up?" a LOT.  Your teacher brings "parents" with "careers" into your class to help you make your decisions.  Your parents bring you to museums, field trips, bring your kid to work day, and lock you in holding cells (no? Just me?) to help you really SEE what it's like in the shoes of other professionals. 

Have you EVER said you "want to be a blogger"?  

You're in luck!! Sally Miller has interviewed 17 bloggers making a full time income with their craft...and she asks them to break down some of their biggest tips!  (Ahem...I MIGHT just be one of the bloggers interviewed...just sayin'.) 

So grab this easy read...and get to implementin'!! 

I know...I've missed SO many books and YouTubers!!  I have LITTLE doubt (and I sincerely hope) that I'll be getting a TON of suggestions from you guys below!!  I tried to keep the list to bloggers and vloggers who aren't just talkin' the talk, butting walking the WHOLE damned 1,000 mile walk!!  

There are SO many voices and "gurus" out there who say we should be "doing this", "doing that", or "doing YOU"...and while it's all good advice, it's a TOTALLY different thing to actually SEE that hustle happen. 

SO...tell me below, who inspires your hustle?  What are you inspired to do today?? 

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