Small Business Series – Introduction

Since I've been working at my small business for a few years now, I thought it would be great to jot down what I've learned so far, in hopes it may be of some interest to anyone else in a similar position. 

Let me preface this entire series by saying this is not a tutorial on creating a small business (let along being successful at it). If I've learned anything from my failures, it's that every circumstance is different. Every business owner works differently, customers respond differently, heck the period of time we're in changes how a business will operate (looking at you 2020). A super successful month in February doesn't imply that March won't tank. So I can't tell you how to become rich quick while making your hobby your career. I haven't done that, and honestly I don't want to.


I can tell you about my successes and failures, though. And most importantly, I can explain what I've learned from them. I can describe the emotional toll this takes on not just the owner, but the family. We can talk about community and taxes and logos and oh-my-goodness should I be on ETSY?! I'll tell you everything I wish I'de known before I started a small business years ago. And I'll tell you right now that it might be completely useless information

But it might not. 

To kick off the series here's a brief run down of my history:

OklaRoots started as a public Instagram account in 2016, so that I could participate in a quilt block party. It was 100 blocks in 100 days and I'de never made a quilt, but all of a sudden I was overcome by a strong desire to sew. 

After participating in the quilt along, I become absolutely hooked. Not only did I want to spend more and more of my time sewing, I wanted to create my own patterns. So I drafted up a free pattern, and started this website ( to have a place to share it.

So "selling free items" doesn't require much. You need a way for people to download it, but you don't have to worry about financial information. However, if you want to get paid for your work, now it's time to think about security (you aren't going to ask folks for their credit card numbers) and making sure you're following all tax rules for your state. After researching as much as I could, I created an online shop (using Shopify and Etsy, we'll have a whole post about that later). 

Spoiler alert: my pattern writing (more like pattern selling) life was short lived. About a year after I opened shop, I shut it down.

And then made a video for YouTube.

Which lead to another video, which 6 months later lead to an exponential increase in my subscribers. 

And about a year and a half after shutting down the doors of shopOklaRoots, I opened them right back up. Except this time I had physical items to sell, and an incredible community who wanted to support the work I was doing. 

And that's where I am now. YouTube videos every week, shop openings (with the hard working help of my mother) every month, quilt patterns back in the works and who knows what's next. 

We'll dig into each of these events and lessons deeply over time. I just wanted to show you the roller coaster, and I've only just gotten started. Imagine what we'll add to this over the next 5 years. 


About The Author

Jessica OklaRoots


  1. Heather Dries | 8th May 21

    Thanks for sharing your story, looking forward to reading your next post.

  2. Jen C | 10th May 21

    HA!…I’m backwards!…had a dog grooming business for over 15 years along the way added a retail shop and lastly a pet bakery…great times and great stress at times. Thanks 2020 I abandoned the dog house and now I’m grooming only out of my house. Cheaper than therapy I bought a sewing machine about 4 months ago stared at it and talked to it for a few weeks and now I have a pile of wallets bags etc. And a kicking kam rivet press. Thanks for the Jumpstart now where’s the Monday video ๐Ÿ˜‰

  3. Claudia Hughes | 10th May 21

    Thank you for your honesty and candid nature! I recently found you on YouTube and love watching your videos. You explain the sewing process wonderfully. Thank you for inspiring me to try new patterns!

  4. Denise | 14th May 21

    Thank you! I discovered your YouTube channel (and subscribed) a few months ago. So far, I have made two Clematis bags and have almost finished a third. Iโ€™m a fairly new sewer and really appreciate the time you have taken to help all of us to learn the skills, tips and techniques in your tutorials. I especially appreciate your excellent closeups to the stitching area which must require a lot of time to get so perfectly angled.

  5. Lauren Messina | 15th May 21

    Jess, I sincerely love watching all of your youtube videos. After long days with work and twins at home listening and watching your videos keep me sane. I look forward to your next post!

  6. Stacey | 17th May 21

    I really enjoyed this post!! It’s nice to learn a bit about my FAVORITE Youtuber! Love your videos and how REAL you are! Keep up the awesome job!! Starting a business can be so daunting… (I type this ON tax day, while avoiding hitting the submit button to Uncle Sam!) Live and Learn… We all go through the trials of small business. Hang in there and just keep plugging away. You have such wonderful ideas and a terrific personality. You’re gonna soar!

  7. Sheryl Jackson | 21st May 21

    I just “discovered” you as you had a tutorial video for one of my patterns I was going to make, one the designer didn’t have, Sallie Tomato’s $2 Lucky wallet. I love your videos. I just completed Emmaline’s Road Trip wallet by watching your video. I want to say thank you. I didn’t start sewing until my mid-50’s, and I love your honesty and enthusiasm. I love that you show we don’t have to be “perfect”. It is all right to make mistakes. Anyway, thank you.

  8. Jaime | 22nd May 21

    I love your story! Thank you for sharing!

  9. Luz | 26th May 21

    Thanks for sharing…Iโ€™ve been sewing since I was a kid but could never find something to sew that I could be passionate about until I saw your tutorials. I love watching your tutorials and now Iโ€™m making pouches and bags, with your help. Keep teaching, youโ€™re awesome at it!!!

  10. Melanie Hargreaves | 4th Jun 21

    I am looking forward to reading about your experiences ๐Ÿ˜Š

  11. Laura Sandy | 8th Jul 21

    Thank you for taking the time to share all of your pearls of wisdom that you’ve gathered over the years. I look forward to this series!! I found your YouTube channel shortly after I was laid off last March due to the pandemic. I was able to find a Singer machine, refresh my skills, and have been watching your channel ever since. Thank you!! ๐Ÿ˜Š

  12. Amanda Lisbony | 11th Jul 21

    Thank you so much for this! How inspiring!

    I’ve recently started following you on YouTube and Facebook. I’ve learned so much. You have an engaging and thorough teaching style. As a teacher of 20 years, I can honestly say that you’re a natural.

  13. Vonnie | 17th Jul 21

    I am 75. I am a guilter and a sewer. I saw your YouTube and decided to do bags. I am now collecting patterns and am starting to sew. My goal in the have a booth in the market in the town square where we have tourists from all over. You are my inspiration. You have my sense of humor and I love to watch you. Thank you for keeping my life interesting and giving me a new adventure to try

  14. Amy | 22nd Jul 21

    Love you’re tutorials! I am new to your tutorials and I have just come back to sewing. I’ve been crocheting rugs and coasters etc. and I needed another project to get excited about! I have a suggestion, maybe you could make a page showing all of the product you use on a regular basis. I really do love your tutorials, but I get confused on which one had what products I needed, and I spend an hour trying to find it… I take notes, but… some of us old people are forgetful! Lol…. Thanks for being there and explaining everything so well…

  15. Vonnie | 1st Aug 21

    Hi. I am a 75 young. Long time sewer and quilter. Live making bags now. I am going to get a booth at upper scale farmers market in old Spanish town in New Mexico. I could not do this with out your help with the patterns. Thank you so much. You are a blessing and a wonderful teacher.

  16. Danise Shields | 1st Aug 21

    I have followed you for the last year or so. Your tutorials have taught me how to make bags and to quilt. I would not have attempted this sewing without you. You saved my sanity through the COVID isolation.
    I look forward to and enjoy all your videos.

    You should be proud of what you have created. Thanks.

  17. Elaine Thompson | 2nd Aug 21

    An inspiring story, I always look forward to your daily updates, things coming up, sneaky peaks, and things you have purchased or been sent. Your enthusiasm for anything sewing is infectious and had encouraged me to get back to sewing after very many years

  18. Beverly George | 4th Aug 21

    It may be a roller coaster but it’s help all of us DREAM bigger! Thanks for your continuous videos, blogs, live chats etc.

  19. Candice Gander | 5th Aug 21

    Thank you so much for your videos. I found you while I was searching for mask tutorials. You made it feel so easy to start sewing. I hadn’t sewn since I made Disney costumes for my kids when they were young. Minnie and Snow White. My sister and I have started making bags and many other things and selling at markets and Etsy. Your videos and business information have been very helpful. Thank you so much and I look forward to your videos everyday.

  20. Erin Robinson | 12th Aug 22

    Thank you for all you do and all the inspiration you give. This blog gives me hope! I am just starting my own business “edelweiss studio” and I am reading ALL the things and probably a little obsessive about my favorites (LIKE YOU!) You have helped teach me how to improve my skills and your positive attitude is infectious. We all have our own beginings – Im so glad you shared yours!

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