The CEO Teacher® Podcast

Episode: CEO Teacher® Success Stories: How to Get Your Products Selling on TpT (Hall of Fame Episode)

Host: Kayse Morris
Date: August 27, 2025
Guests: Kiana Funderberg, Jocelyn Hubbard, Sydney Lafriends

Episode Overview

In this Hall of Fame episode, Kayse Morris brings together three powerhouse CEO Teacher® School alumni—Kiana, Jocelyn, and Sydney—to share their real and relatable journeys in building successful online teacher businesses through Teachers Pay Teachers (TpT) and CEO Teacher® frameworks. The conversation dives deeply into their unique paths, setbacks, breakthroughs, and the transformative power of coaching, community, and mindset shifts. If you’ve ever wondered how everyday educators turn passion and experience into sustainable businesses, this episode delivers both practical strategies and heartfelt inspiration.

Meet the Guests (02:40–06:21)

• Kiana Funderberg (@theartofphonology): 4th grade teacher outside Atlanta, started her TpT journey in 2019.
• Jocelyn Hubbard (@teachcustom): Former 7th & 8th grade ELA/social studies teacher in South Carolina, transitioned to coaching/consulting for culturally responsive teaching. TpT store & business: "Custom Teaching Solutions". Opened her TpT store in 2013 but only got serious recently.
• Sydney Lafriends (@learningwithlafriends): Former 4th grade teacher in Iowa, now staying home with her kids and supporting new and student teachers alongside her TpT business. Started TpT in 2013 but didn't focus on it until joining Casey’s course.

Key Discussion Points and Insights

1. Getting Started: “I didn’t even know this world existed”

• Discovering Teacherpreneurship: Each guest described how they stumbled upon the teacher business world, often via “teachergram” and Instagram communities.
• Taking the Leap: Hesitation about investing in Casey’s program was universal, but all found the decision life-changing.
• Sydney: Found Kayse via a side-hustle handbook and was “convinced” after reading her story. Joined CEO Teacher® School as a birthday present from her husband.
• Jocelyn: “My husband kept saying, Jocelyn, if you would just take this thing seriously, I know you can be successful.” (12:21)
• Kiana: Purchased the course with a teacher friend at the start of the pandemic, calling it “the start of the rest of our lives.” (08:02)

2. Balancing Roles: Teacher, Parent, and Business Owner

• Scheduling & Time Management:
  • Kiana carved out 2 days a week for course videos and Saturday for creating, likening it to grad school. “If you want to accomplish something, you’ll get it done.” (09:49)
  • Sydney’s work-from-home schedule: “Kids go down for a nap, get as much work as you can get done...work until midnight.” (22:21)
• Motherhood & Business: All reflect on the unique challenges of starting/running a business with young children, especially during the pandemic.

3. The Power of Coaching and Community (10:41–14:39)

• Game-Changing Accountability:
  • Sydney: “The coaching calls are a game changer for sure. I couldn’t miss them.” (11:14)
  • Jocelyn highlighted how staying connected via coaching calls combats isolation: “Once you get out of the classroom...this journey can be really lonely. Not that many people understand what you’re doing.” (13:26)
• Lifelong Friendships: Friendships and collaborations grew organically from the coaching call chat and DMs—supporting professional growth and reducing the sense of “going it alone”.

4. Transformative Personal Growth

• Clarity & Confidence: Jocelyn credits Casey’s mind-mapping module with giving her clarity and direction—“that right there was transformative.” (16:19)
• Limitless Mindset: Kiana: “I now see there literally is no ceiling to what I could do even while I'm still a teacher...knowing I’m limitless is a very exciting and liberating feeling.” (17:25)
• Sydney: “You will make the money back. I was floored that I made it and then some in two months.” (38:09)
• Empowerment: All three speak passionately about how the program and surrounding community helped them see themselves as entrepreneurs, not “just” teachers.

5. Applying Business Skills: Beyond TpT

• Brand-Building:
  • Kiana transformed “The Art of Phonology” from a hobby to a full-fledged brand.
  • Jocelyn applies design and marketing lessons from CEO Teacher® School to her consulting practice.
  • Sydney jokes they all deserve a “degree in marketing design” after completing the course (25:50).
• Multiple Revenue Streams: The program’s lessons are relevant to consulting, coaching, content creation, not just TpT.

6. What Actually Drives TpT Sales? (Instagram ≠ Dollar Signs)

• Social Media vs. Email & SEO: Kiana’s IG following doesn’t necessarily translate to direct TpT sales—her email list and SEO work are far more effective. (19:25, 20:45)
• Creating for Your Own Classroom: All three focus on making resources they themselves use, which then sell well to others.

7. Practical Takeaways: Step-by-Step System > Random Googling

• System over Scattered Info:
  • Jocelyn: “You share a ton on your blog and podcast—but that’s just the surface. There’s a whole other level and the system.” (26:47)
  • Kiana: “You see people at the end, but you don't know all that is a part of making that happen.” (27:22)
  • Sydney: “I would spend way too long googling things if I had to do it that way.” (28:10)

8. Search Engine Optimization (SEO): The Real Game Changer (29:58–33:53)

• Learning SEO: All three had no idea what SEO was before the course.
• Coaching Calls = Clarity:
  • Kiana: “SEO took me a while to understand...Once you get your SEO down...it really does help you with the competition.” (30:55)
  • Sydney: Describes how fun and rewarding it is to google a long-tail keyword and see her own product at the top.
  • Jocelyn: “When there’s more than one mind thinking about things, your end result is better.” (31:58)

9. If You’re On the Fence About Investing

• Do it—even if you’re scared:
  • Jocelyn: “This is your season for this...If I can do this with just half the things she taught me, what can I do with the rest?” (35:04)
  • Kiana: “This was the cost of a new beginning...it gave me the motivation I needed to keep going.” (35:48)
  • Sydney: “There’s no losing. You will make the money back...I have never heard of a single person regret joining your course.” (36:52, 38:09)

Notable Quotes and Memorable Moments

• "I started my TPT journey January of 2019… but you would never ever think that after looking at your Instagram. You've got it going on." – Kayse to Kiana (03:01)
• "My world has definitely changed…A lot of that I learned through the CEO Teacher School. Back to school last year, I made over $1,200 in August." – Kiana (08:10)
• "The coaching part might be easily one of my favorite parts… I couldn't miss them." – Sydney (10:41)
• "This journey, once you get out of the classroom, can be really lonely… having that community has been a game changer. Lifelong friends." – Jocelyn (13:26)
• "The CEO Teacher School has made me realize that I am limitless." – Kiana (17:25)
• "I checked all the numbers before I came on. It was like a 375% increase from October 2019 to October 2020...my husband watched me work as hard as I could because it was important to me to see this through." – Sydney (21:51, 22:21)
• "I was able to make The Art of Phonology a brand after being a part of the CEO Teacher School. The lessons aren't just limited to Teachers Pay Teachers—you truly are making us entrepreneurs in all different assets." – Kiana (25:08)
• "You see people at the end, but you don't know all that is a part of making that happen… I would not even know to Google that." – Kiana (27:22)
• "I feel like if I were to Google back before I did the course, it would have been like 'how to be successful on Teachers Pay Teachers.' In my head, your face would pop up because I literally don't know what else we could possibly learn." – Sydney (28:10)
• "SEO took me a while to understand...Once you get your SEO down and those long tail keywords, it really does help you...I was able to stand above the crowd because I was able to be found easier." – Kiana (30:55)
• "There's no losing. You will make the money back. I was floored that I made it and then some in two months." – Sydney (36:52)
• "If you're here watching this or listening to this for a reason, that's your reason. I say go for it." – Sydney (38:09)

Timestamps for Key Segments

• Introductions & Backgrounds: 02:40–06:21
• Getting Started on TpT & Joining CEO Teacher® School: 06:59–10:16
• Coaching, Community, Accountability: 10:41–14:39
• Personal Transformations: 15:00–18:36
• Building a Brand, Not Just a Side Hustle: 24:16–26:32
• Can’t Google Your Way to Success: 26:32–29:00
• SEO Breakthroughs: 29:58–34:09
• If You’re On the Fence / Final Advice: 35:04–38:09

Takeaways for Aspiring CEO Teachers®

1. Community and coaching are as important as business strategies.
2. Investing in yourself often pays off quickly both financially & personally.
3. A systems-based approach is far more effective than patchworking free advice.
4. SEO and email lists drive sales more than social media followings.
5. Everyone starts as a beginner, and limitless is a mindset cultivated through action.

This is a must-listen for educators dreaming of more—financially, personally, professionally—and proof that your “side hustle” can become your dream career.