Pretty Okay Podcast

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A podcast for creative women hosted by Samantha Welker (Harvard MBA, Business Manager Glitter Guide) and Julia Wheeler (Gunn & Swain, Seaesta Surf). We hope this podcast will use our collective skills and years in both the corporate world and self-employed one to educate, inspire and connect with wo…

Pretty Okay Podcast


    • Jan 27, 2025 LATEST EPISODE
    • monthly NEW EPISODES
    • 38m AVG DURATION
    • 90 EPISODES

    4.9 from 46 ratings Listeners of Pretty Okay Podcast that love the show mention: actionable steps, sam, business owners, finance, apply, creative, witty, smart, info, advice, experience, excited, knowledge, love, talk, real, need, funny, thank, good.


    Ivy Insights

    The Pretty Okay Podcast is a must-listen for anyone in the business world, whether you're a seasoned entrepreneur or just starting out. I have personally been in business for over 5 years and after giving this podcast a few listens, I am confident in saying that you will definitely come away from each episode with concrete tools and applicable advice! The hosts, Sam and Julia, make for a great dynamic duo, each bringing their own unique perspective to each topic. It's not just banter like some podcasts can be; I always leave inspired and entertained!

    What I love most about this podcast is that it covers a wide range of topics that are relevant to all aspects of life, work, friendships, and everything in between. Whether it's organization, finance, or building relationships, Sam and Julia tackle it all with wit and intelligence. They have the ability to break down tough topics into actionable steps that take the intimidation out of things that small business owners need to know.

    The hosts keep it real throughout every episode. They understand the juggle and struggle of running a business and genuinely want to provide help and resources to their listeners. Their experience and education in the industry shines through as they offer practical advice based on real-world scenarios.

    One potential drawback of this podcast is that it may not cater to everyone's taste. While I find the humor witty and intellectual, others may not appreciate the style of delivery. Additionally, some listeners may prefer more in-depth discussions on specific topics rather than broad overviews.

    In conclusion, The Pretty Okay Podcast is an excellent resource for anyone looking for advice on entrepreneurship, finance management, organization skills, or even just a good laugh. Sam's expertise combined with Julia's perspective creates a truly valuable listening experience. I highly recommend giving this podcast a listen if you're ready to learn and be entertained at the same time!



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    Latest episodes from Pretty Okay Podcast

    So you want to be an educator?

    Play Episode Listen Later Jan 27, 2025 40:46


    What happens when two former classroom teachers step into the wild world of business education? A lot of laughs, some unexpected shade, and serious insight into what it means to truly teach. In this episode, host Tayler sits down with Laylee Emadi, founder of The Creative Educator Conference and Educator's Lounge, to tackle the big question: Are you really an educator or just a motivational speaker in disguise?Together, they explore the rise of self-proclaimed "educators," the blurred lines between storytelling and actual teaching, and how to turn real expertise into transformative learning experiences. They also dive into why educators should never use paying customers as guinea pigs and the critical difference between professionals who speak and professional speakers. Oh, and did we mention the hard-core auntie energy? Get ready to feel inspired, learn something new, and maybe even join Laylee's exclusive Educator's Lounge. Press play and discover the plan for your world domination (no crying required).

    Simplify It the F#%! Down: Tackling Marketing Overload

    Play Episode Listen Later Dec 16, 2024 42:02


    Are you feeling crushed under the weight of all the things in your marketing to-do list? Join Tayler and her ultimate podcast BFF Samantha Welker as they break down the marketing madness and teach you how to focus on what actually matters. Discover why you're doing too damn much, how to audit yourself like a pro, and why simplifying it the f#%! down is the mantra we all need. Don't miss this one—it's equal parts therapy and strategy.

    You Gotta Stay Close to the Money

    Play Episode Listen Later Nov 25, 2024 33:19


    Do you feel like marketing your business is an endless to-do list of Instagram posts, email campaigns, and reels—with little to show for it? Join Tayler and revenue strategist Frenchie Ferenczi as they tackle the real goal of marketing: staying close to the money. Frenchie shares her no-nonsense money-first philosophy, reminds us what the five core functions of marketing are (it's easy to forget), and why overthinking your to-do list might be the biggest thing holding you back. From busting myths about needing to "market at scale" to finding your bare minimum marketing strategy, this episode is perfect for the solopreneur or service provider looking to break free from the feast-or-famine cycle.

    Just Do the Damn Thing

    Play Episode Listen Later Oct 28, 2024 31:43


    Most entrepreneurs sit on their ideas for way too long. You know, waiting for the "right time" to start their business. The thing is, there is never a "right" or "perfect" time to start a business—you just gotta do the damn thing! In this episode, Tayler teams up with her longtime friend and powerhouse entrepreneur Marina Pannell—owner of Harper & Ivory bridal boutique. Together, they dive into Marina's wild journey from almost starting a coffee shop to finally opening her dream business, even as the world was shutting down. Whether you're stuck overthinking or just waiting for someone to tell you to hit go, Tayler and Marina are here to remind you: the time is now. Strap in, it's time to get uncomfortable (in the best way possible)! Want more Pretty Okay? It's all right here!Turbocharge your brand's exposure and become a sought-after podcast guest with PodcastAlly.com!Pretty Okay is hosted by Tayler Cusick Hollman, founder of Enji, and produced by Earfluence.

    You Too Can YouTube

    Play Episode Listen Later Sep 30, 2024 33:22


    YouTube isn't just for influencers and cat videos any more—but you knew that. The thing you might not know though, is the fact that being on YouTube is a smart move for pretty much any small business! And in this episode of the Pretty Okay Podcast, Tayler chats with YouTube expert LaShonda Brown, who shares how service providers can harness the power of YouTube to grow their biz and (gasp) maybe even work less! From 20-hour work weeks to leveraging long-form content and YouTube Shorts, LaShonda talks all about her top tips for getting started on YouTube—even if you're camera-shy. Want more Pretty Okay? It's all right here!Turbocharge your brand's exposure and become a sought-after podcast guest with PodcastAlly.com!Pretty Okay is hosted by Tayler Cusick Hollman, founder of Enji, and produced by Earfluence.

    No Time? No Strategy? No More Excuses!

    Play Episode Listen Later Aug 26, 2024 42:23


    We're trading the soft kid gloves for brass knuckles in this episode! Tayler teams up with the ever-fierce Candice Coppola to dish out some tough love on the excuses they hear about why you can't get to your marketing. From "I don't have time!" to "I need a strategy first!", your marketing aunties expose the lies you tell yourself and offer a hearty cuddle of wisdom to get you back on track. Tune in, laugh, cringe, and (most importantly) start doing the damn thing! Want more Pretty Okay? It's all right here!Turbocharge your brand's exposure and become a sought-after podcast guest with PodcastAlly.com!Pretty Okay is hosted by Tayler Cusick Hollman, founder of Enji, and produced by Earfluence.

    Irresistible Offers and Unfiltered Truths with Braden Drake

    Play Episode Listen Later Jul 29, 2024 33:10


    It's not often you get to sit down with a lawyer let alone someone like with Braden Drake—a lawyer for creatives, business owners, and drag artists. But this episode isn't what you'd expect because most lawyers aren't entrepreneurs. And we dug into one of the most important things any entrepreneur can do—create irresistible offers. From what to think about when you're coming up with the best offer you can to how to handle it when the haters show up because your offer is just that good, we talk strategy, the absurdity of overpriced templates, and why sometimes shaking up the market is the best move you can make. But don't get it twisted! This is not legal advice. Turbocharge your brand's exposure and become a sought-after podcast guest with PodcastAlly.com! Pretty Okay is hosted by Tayler Cusick Hollman, founder of Enji, and produced by Earfluence.

    How to Unlearn Your Way to the Top

    Play Episode Listen Later Jun 24, 2024 50:19


    Ever felt like you're juggling between getting things done and trying to lead effectively? You're not alone! Your host Tayler Hollman is back, and she's got Audrey Kwan in the hot seat to talk transitioning from being a doer to a leader (there's a lot to unlearn here, folks). So get ready to embrace the gray areas of leadership and discover how to motivate, delegate, and support your team like a pro. Turbocharge your brand's exposure and become a sought-after podcast guest with PodcastAlly.com! Pretty Okay is hosted by Tayler Cusick Hollman, founder of Enji, and produced by Earfluence.

    You Can Totally Run Your Own Social Media Ads

    Play Episode Listen Later Jun 10, 2024 36:53


    Regardless of where you currently sit on the I-hate-Meta spectrum, it's hard to deny the fact that social media ads are a fast and pretty cheap way to get in front of your ideal customers. But wanting to run social media ads is one thing. Actually knowing it's the right thing for your small business is another—let alone whether you should do it yourself or hire someone. So, in this episode, seasoned social media advertiser, Jaymie Tarshis, joined me on the pod to chat about the age-old dilemma: to DIY your social media ads or hire an agency for ad campaigns?  Turbocharge your brand's exposure and become a sought-after podcast guest with PodcastAlly.com! Pretty Okay is hosted by Tayler Cusick Hollman, founder of Enji, and produced by Earfluence.

    Build it and they will shop

    Play Episode Listen Later May 27, 2024 40:34


    It takes guts to start a small business, but it takes real guts to start one that's brick and mortar. And in this episode of the Pretty Okay Podcast, Tayler sits down with shop owner, Katherine Oyer of Francis Henri, to talk about her experience going from an online baby store to a brick-and-mortar haven for little ones. If you've ever wondered what it's like to run a retail store with overhead or what it takes to make your online store work IRL, grab your favorite stuffie and listen in! Turbocharge your brand's exposure and become a sought-after podcast guest with PodcastAlly.com!Pretty Okay is hosted by Tayler Cusick Hollman, founder of Enji, and produced by Earfluence.

    Is your copy badass or just...bad?

    Play Episode Listen Later Apr 29, 2024 34:02


    Get ready to break all the writing rules and unleash your inner copywriting genius with Gillian Griffith! Join Tayler and Gillian, longtime professional partners and masters of the written word, as they spill the tea on how to transform your writing from drab to fab. From overcoming the fear of judgment to embracing the power of the ugly first draft, they're demystifying the art of copywriting. Plus, unlock the secret to finding inspiration in unexpected places, from Pottery Barn catalogs to Reformation emails. Turbocharge your brand's exposure and become a sought-after podcast guest with PodcastAlly.com!Pretty Okay is hosted by Tayler Cusick Hollman, founder of Enji, and produced by Earfluence.

    Live, laugh, lead generation!

    Play Episode Listen Later Mar 25, 2024 41:15


    In this episode, Tayler and Davey Jones of Sumo are spilling the tea on what it takes to have a good lead generation strategy for your small business—we promise it sounds more corporate than it really is! From helping you understand what lead gen is and why small businesses can find themselves in a lull without enough leads to quick and long-play lead gen tactics you can try, there are plenty of "aha" moments in this episode. So grab your favorite beverage, settle in, and get ready to become way better at lead gen with Tayler and Davey! Turbocharge your brand's exposure and become a sought-after podcast guest with PodcastAlly.com! Pretty Okay is hosted by Tayler Cusick Hollman, founder of Enji, and produced by Earfluence.

    Influencers, man

    Play Episode Listen Later Feb 26, 2024 45:05


    The Pretty Okay Podcast is back b*tches! And in this episode, Tayler and Sam dive straight into the deep end of the influencer pool—because while some of them are great partners, others make us think "Whyyyy?" From the frustrations faced by many small business owners to how influencers can do a better job of approaching them, get ready for a candid conversation filled with rants, revelations, and more than a few spicy takes. Buckle up for an unfiltered journey into the business of being Pretty Okay

    How To Make More Money in 2023

    Play Episode Listen Later Jan 10, 2023 37:59


    *spoiler alert* it's time to raise your prices. Whether you've been in business for yourself for a while now or the COGS for your production are on the rise, consider this your roadmap for when to raise your prices and how. 

    How Small Business Owners Can Make It Through The Recession

    Play Episode Listen Later Dec 8, 2022 37:56


    Even though recessions are "normal", that doesn't make them suck any less. If your business made it through the pandemic, a lot of the things you thought about and did for that are applicable here. In this episode, we talk about how not to freak out later and what you can do when people around inevitably do start freaking out. 

    Ho-Ho-Holiday Promos That Will Convert

    Play Episode Listen Later Nov 7, 2022 38:15


    The time to start planning your holiday promos and offers was this summer. But if you're a little late in the game there's still time to make the most of your marketing strategy this holiday season.

    Guess who's back in the house?

    Play Episode Listen Later Oct 19, 2022 25:29


    We're back from summer break! Come see if we remember how to do a podcast!

    Why Your Best Answers Will Always Come From Customers

    Play Episode Listen Later Jun 22, 2022 48:44


    In our last episode before summer break, Tayler sits down to interview friend, entrepreneur, and all-around inspirational babe Martha Bitar, founder + CEO of Flodesk. Tayler and Martha dig into how you can (and should!) use customer feedback to help your business thrive while still staying true to your vision. 

    4 Ways To Become a Thought Leader In Your Industry

    Play Episode Listen Later Jun 8, 2022 37:46


    *spoiler alert* it isn't about being the "smartest" person in the room. In today's episode, we're breaking down the characteristics of a "thought leader" and sharing 4 efficient ways you can become one in your industry.  

    This Meeting Could Have Been An Email

    Play Episode Listen Later May 25, 2022 37:38


    Don't schedule meetings for meetings' sake. On today's episode, we're talking about how to know when meetings are beneficial (for everyone), how to gracefully move them along, and the steps you should be taking to lead them effectively. 

    Why Vanity Numbers Are Bullsh*t

    Play Episode Listen Later May 11, 2022 34:56


    We're just going to say it…vanity numbers are bullshit. Your follower count and number of likes don't matter if your social media content isn't converting. You can't take little hearts to the bank, you guys. In today's episode, we're digging into the social media metrics that do matter and which ones are just vanity numbers that aren't indicative of how your brand is doing.  

    Navigating The First Year In Business with Jasmine Smith

    Play Episode Listen Later Apr 27, 2022 53:25


    In today's episode, Tayler is joined by entrepreneur and strategist Jasmine Smith to discuss the ups and downs of navigating that first year in business. From founding her own marketing agency to her newly launched event space, Jasmine shares her experience with learning as you go, the importance of community and navigating those “oh, shit” moments as a business owner. 

    Girl, Do Your Taxes!

    Play Episode Listen Later Apr 13, 2022 53:28


    Like B. Franklin once said, "Nothing in life is certain except death and taxes". At least it was something to that effect. We promise to only talk about taxes once, but this episode is it. Put on your big girl pants and saddle up. It's not fun, but it's required, so let's go. 

    How To Write Copy That Converts

    Play Episode Listen Later Mar 30, 2022 28:37


    Ready to become your brand's very own wordsmith? You don't have to be a professional copy editor to make your voice heard when it comes to your website. Reach your ideal customers and share the heart of your brand with Tayler's foolproof strategy. 

    The Anatomy of a Bitchin' Website

    Play Episode Listen Later Mar 16, 2022 54:18


    What does it take to have a website that converts? Tayler is breaking it down step-by-step so you have all your boxes checked. 

    Planning For Business Growth

    Play Episode Listen Later Mar 2, 2022 30:33


    In today's minisode, Tayler is taking you through the necessary steps of planning for business growth. Because no one wants to be caught with their pants down right when things start taking off. 

    How To Hire The Right Person The First Time

    Play Episode Listen Later Feb 16, 2022 44:47


    Whether you are hiring an employee, a contractor, or even a consultant, it's crucial to have your ducks in a row before pulling the trigger. We're breaking down what to look for, red flags to avoid, and common mistakes many small business owners make. 

    So You've Decided To Make A Career Change...Now What?

    Play Episode Listen Later Feb 2, 2022 50:02


    If any of our signs from last week's episode resonated with you, then you may be wondering, “now what?” In this episode, we're walking you through what you should and shouldn't do before making a career change, including what numbers to crunch, goals to set, and more.

    Signs It's Time To Make A Career Change

    Play Episode Listen Later Jan 19, 2022 44:41


    There are a lot of different reasons to make a change in your career, but which ones should prompt an immediate departure and which ones should be a gentle nudge? Whether you are self-employed or working a corporate 9-5, we're breaking down all the red flags that you should consider before making any life-altering decisions. 

    All About That New New

    Play Episode Listen Later Jan 5, 2022 44:09


    We're back after an extra-extended summer vacation. Not only that, we've got a new look, new jobs, new babies—it's nuts!

    School's Out For The Summer!

    Play Episode Listen Later Jul 7, 2021 60:42


    It's our last episode of the season as we take a summer break to recharge, birth a baby and things like that. In today's episode Sam and Taylor recap this season, our favorite episodes, popular topics + more. 

    How To Say No Without Being A Complete Asshole

    Play Episode Listen Later Jun 23, 2021 47:45


    Saying "no" to a client, friend or coworker is easier said than done...Especially if confrontation makes you want to run and hide. In today's episode we're sharing our best advice for strategically saying no - which means assessing each ask, formatting the conversation, and sticking to your guns. 

    Newsflash: You Don't Need To Reinvent The Wheel

    Play Episode Listen Later Jun 9, 2021 45:09


    Every creative entrepreneur wants to be known for disrupting the industry, but sometimes it does more harm than good. In today's episode we're pinpointing the specific systems and processes that don't need reinventing and how you can allocate your resources more effectively as a business owner. 

    It’s Time To Be Vulnerable AF

    Play Episode Listen Later May 26, 2021 48:41


    Vulnerability is often viewed as a weakness in the "business" world, but we beg to differ. In today's episode, we're talking about the power of vulnerability, how and when to recognize the opportunity for it, and why it might just be the best thing you can do as a business owner.

    Trust Me, I'm an Influencer

    Play Episode Listen Later May 12, 2021 51:43


    Can we all just admit that the "influencer" world is a mess? And yet, they are somehow still a necessary tool for your marketing strategy. In today's episode, we talk about the good, the bad and the ugly of working with influencers, how to find one that aligns with your brand, and how to create a fruitful relationship. 

    Metrics or It Didn’t Happen

    Play Episode Listen Later Apr 28, 2021 43:35


    If you own a business and you aren't using Google Analytics, what are you even doing with your life? Today we're sharing why you absolutely need to utilize Google Analytics for tracking and growing your business and what Google Analytics can do for you. 

    Which Social Media Platforms You Need To Be On

    Play Episode Listen Later Apr 14, 2021 54:27


    Do you really need to be on every. single. social. media. platform out there in order to maximize the benefits? The short answer? NO. We’re breaking down the different platforms, their pros and cons, and what you need to be looking for in each one before dividing up your resources.

    Convincing Clients You're Worth The $$$

    Play Episode Listen Later Mar 24, 2021 10:14


    This week's (mini) episode is Tayler ridin' solo as she gives you a quick and dirty breakdown of how to convince clients you're worth what you're charging. Listen to the episode for her 4 best tips on what action steps you can take to make that money (honey).

    Our Biggest Pet Peeves in Business

    Play Episode Listen Later Mar 10, 2021 52:03


    In this week's episode of Pretty Okay Podcast, we're cover the next requested topic from our IG audience: Pet Peeves. What bugs us most when working with people or people who work for us? Don't worry, we have plenty to share. 

    How To Work With Friends Without Screwing Each Other Over

    Play Episode Listen Later Feb 24, 2021 57:14


    For our 50th episode (!!) we’re diving into the topic you voted for on IG...working with friends! We’re going over the good, the bad and the ugly of going into business with your buddies to make sure your business is successful and your friendship doesn’t crash and burn. 

    Can We Finally Hack The Instagram Algorithm in 2021?

    Play Episode Listen Later Feb 10, 2021 52:21


    In this week's episode, Sam and Tayler tackle Later Media's recent article breaking down how to "hack" the Instagram algorithm in 2021 based on advice directly from the source. 

    How To Have Confidence In 2021 When The World Is A Clusterf*ck

    Play Episode Listen Later Jan 13, 2021 44:44


    Happy New Year! Or is it? We all know the world is upside down right now and many businesses are struggling through this pandemic. But confidence as a creative entrepreneur matters more than ever. In today’s first episode of the new year, we’re breaking down all the ways you can grow your confidence as a business owner, creative, and human…even when the world is a sh*t show.

    Good Riddance, 2020.

    Play Episode Listen Later Dec 16, 2020 55:12


    We're closing out the year the best way we know how-talking about sh*t. Tayler and Sam put a bow on 2020 by going over the trials that this year brought, the power of gratitude, and how business owners can thrive in 2021.

    Bonus Glitter Guide Q&A Episode with Taylor Sterling

    Play Episode Listen Later Dec 14, 2020 46:17


    Sam sits down with her Glitter Guide wife to answer all of your Q's!

    glitter guide taylor sterling
    Soft(core) Skillz

    Play Episode Listen Later Dec 2, 2020 54:11


    Soft skills aren’t the same as being good at your job. Having a a full-rounded set of soft skills makes you not only a better business owner or worker, but a better human.

    How To Give Yourself An Annual Review When You're The HBIC

    Play Episode Listen Later Nov 18, 2020 52:04


    When you're running your own business, you're often tasked with giving employee reviews. But what about your own review? In today's episode, we are sharing how you can review your own performance (prompts included!) to make sure you're on the path to continuous growth + success in 2021!

    Tips For Blending Personal Politics + Business

    Play Episode Listen Later Nov 4, 2020 31:41


    It's the day after the election but we're still talking politics. This entire election season has brought up an important question: How do we blend our personal politics into our business? Do we have to? Do we even want to? Tayler breaks it down and shares her best tips for incorporating your political beliefs and values into your marketing. 

    Giving Constructive Criticism Without Sounding Like An A$$hole

    Play Episode Listen Later Oct 21, 2020 44:56


    As business owners, collaborators and creatives, you will have to give constructive criticism to people you’re working with. And the way you handle giving criticism and feedback can make or break a project. In today’s episode we’re breaking down how you can effectively dish out constructive criticism to get the results you want, as well as tips for accepting it when it comes your way.

    How To Maximize Your Content

    Play Episode Listen Later Oct 7, 2020 64:41


    As business owners and creatives we spend so much time creating content for our brands. Rather than spending 10,000 hours trying to create new pieces of content, we’re sharing our tips for maximizing your content and getting the most bang for your buck.

    How To Stop Giving Away Your Brain 4 Free

    Play Episode Listen Later Sep 23, 2020 53:18


    In this week's episode we're chatting about how we as business owners can stop giving away our time for free. Whether it's from friends who are asking for freebies (advice or product) or overzealous clients, we're sharing our tips for setting boundaries, covering your ass and how to protect yourself moving forward. You've spent a lot of time and resources growing that beautiful talent of yours, don't give it away for free!

    How To Launch A Business Without Losing Your Goddamn Mind: Part 6

    Play Episode Listen Later Sep 9, 2020 54:49


    In the 6th and final part of our How To Launch a Business series we're diving into all the random shit that no one tells you about running a biz.

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