Digital Social Hour: Harrison Hightower – From Pharmacy to CEO: My Bold Career Pivot

Episode: DSH #1510 | Host: Sean Kelly | Guest: Harrison Hightower
Date: August 27, 2025

Episode Overview

In this episode, Sean Kelly sits down with Harrison Hightower, CEO and founder of High Prep Tutoring, to discuss his striking transition from a career in pharmacy to entrepreneurship in the education space. The conversation delves into Harrison's early life, the value of standardized test prep, the impact of technology and AI on learning, lessons in confidence and fulfillment, and actionable advice for the next generation.

The episode is filled with candid reflections, motivational insights, and actionable takeaways for aspiring entrepreneurs, educators, students, and anyone pondering a bold career change.

Key Discussion Points and Insights

1. Harrison’s Journey: From a Small Town and Pharmacy to Tutoring CEO

• Early Background:
  • Grew up in Jacksonville, Alabama, attending a small rural school with 70 students in his class ([01:09]).
  • Parents did not have a college fund, so he realized he needed scholarships to afford university ([01:17]).
  • “I found out in about 10th grade that...if you had a certain ACT score and GPA, they would pay 100% of your tuition.” ([01:23] – Harrison)
• Mastering Standardized Tests:
  • Started with a 22 on the ACT and, through relentless self-study and strategy, improved to a 32 composite and earned a full ride to Auburn ([02:49]).
  • Began helping others—including his brother—boost their scores, seeding the idea for his eventual business ([03:02]).
• Career Pivot:
  • Originally pursued a PharmD at Auburn but launched the tutoring company during pharmacy school in 2021 after discovering his passion for student mentorship and business ([03:42]).
  • “I was way more passionate about helping students and kind of felt like that was my...real calling and passion.” ([03:38] – Harrison)

2. The ROI and Value of Test Prep

• Financial Logic:
  • Preparing well for standardized tests is one of the best financial investments for college-bound families ([04:06]).
  • “Invest something in standardized test prep because the ROI is better than any kind of college fund you could start.” ([04:16] – Harrison)
• Test Strategies Over Content Mastery:
  • High-performing students often struggle on standardized tests due to lack of strategy ([04:30]).
  • “It’s knowing how to take the test and having the right knowledge about the correct content.” ([04:30] – Harrison)
• Benefits of One-on-One Tutoring:
  • Personalized attention is crucial—something lacking in big public schools. Both host and guest recall personal gains from tutoring ([05:20]).

3. Regional Differences in Testing, Declining Scores, Digital Age Effects

• ACT vs. SAT by Region:
  • ACT is more common in the Southeast, SAT in the Northeast, but most universities accept both ([07:29]).
• Decline in National Test Scores:
  • Average ACT/SAT scores are at a 30–40 year low, likely due to shortened test formats and diminished student attention spans ([08:19]).
• Social Media Impact:
  • The present digital generation has fundamentally different attention patterns than previous ones ([08:37]).
  • “These kids in high school...they’ve had an iPhone in their hand since they were three years old.” ([09:08] – Harrison)
  • Importance of intentional use of technology for personal growth ([10:04]).

4. The Real Role of Tutors: Accountability, Confidence, and Mentorship

• Beyond Just Academics:
  • Human touch in tutoring provides accountability and emotional support that AI can’t match ([11:21]).
  • “What I don’t think [AI] will ever solve is the accountability where it’s like when people have a real person, you know, live tutor...it’s the accountability...that helps a lot.” ([11:21] – Harrison)
• Building Student Confidence:
  • Tutors can help shy or struggling students build self-assurance and find community ([13:22]).
  • Stories shared about students who blossomed socially and academically due to ongoing mentorship ([14:19]).

5. From Book Smarts to Real-World Skills and Entrepreneurship

• Mentorship and Real Experience:
  • Value is placed on personal experience over age or hype—hire mentors who have done the actual work ([16:32]).
  • “I only hire mentors with experience...it’s all experience.” ([16:34] – Sean)
• Fast-Paced Learning in the Digital Era:
  • The 10,000-hour rule is questioned in today’s environment where tools like ChatGPT have accelerated skill acquisition ([17:14]).
  • “I don’t believe in the 10,000 hour rule anymore...You could get really good really fast with all the information these days.” ([17:14] – Sean)

6. Favorite Books, Learning Methods, and Podcasts

• Influential Books:
  • Sean’s top reads: “$100M Offers,” “How to Win Friends & Influence People,” Tony Robbins’ “Life Force”—plus “Rich Dad Poor Dad” and “Atomic Habits” ([18:34]–[20:03]).
  • Harrison’s go-to recommendations for students: “How to Win Friends...”, “Rich Dad Poor Dad”, “Atomic Habits” ([19:19]).
• Learning Styles:
  • Both guests prefer audio-based learning (podcasts/audiobooks) for multitasking.
  • “That’s why I’ve been so huge on podcasts. Always.” ([36:09] – Harrison)
• Top Podcasts:
  • Diary of a CEO, Alex Hormozi, Bradley, Rob Dyrdek (for systems thinking/time management), School of Greatness, Huberman Lab, Rogan ([36:38]–[38:32]).

7. Fulfillment, Money, and Life Lessons

• Happiness & Fulfillment:
  • Both Sean and Harrison warn against tying self-worth to money or external achievements; process and purpose matter most ([20:02]–[21:23]).
  • “Realizing...you’re never going to be happy when you reach the destination. It’s realizing that it’s the process of getting there.” ([20:29] – Harrison)
• Giving Back Through Leadership:
  • Harrison shares how fulfillment now comes from impacting his team and students—helping them achieve their own breakthroughs ([26:31]–[28:12]).
  • “When I see...a young person gain that confidence...that’s the most fulfilling thing to me.” ([27:26] – Harrison)
  • Both hosts note that helping others—staff or students—brings greater satisfaction than financial success ([28:38]).

8. Business Models, Growth, and Staying Authentic

• Selling a Business?
  • Harrison is uninterested in selling to larger tutoring franchises or private equity for now—prefers maintaining quality and personal fulfillment ([29:39]).
  • Sean parallels this with podcast network buyout offers ([30:14]).
• Downsides of Selling:
  • Loss of control, purpose, and creativity cited as major drawbacks to selling out ([30:44]).

9. Mindset, Confidence & Small Wins

• Overcoming Fear of Judgment:
  • Harrison details the apprehension of switching careers and confronting public perception ([25:44]).
  • “You just kind of quit giving a shit what people think, and you gotta put yourself out there and do it.” ([26:32] – Harrison)
• Chain of Small Wins:
  • Success in fitness or coursework builds the confidence required for bigger undertakings, whether it’s entrepreneurship or personal growth ([25:16]–[27:01]).

10. Practical Advice for Aspiring Students and Entrepreneurs

• Significance of Mentorship and Proactive Outreach:
  • “Lean into mentorship, find somebody that’s kind of been there and done that and let them help you and guide you and save you time.” ([46:01] – Harrison)
• Personal Brand Matters:
  • Building a personal brand is vital as AI disrupts the workforce ([39:21]).
  • “People want to do business with people they relate to.” ([39:51] – Harrison)

Notable Quotes & Memorable Moments

• On ROI of Test Prep:

  • "Invest something in standardized test prep because the ROI is better than any kind of college fund you could start." – Harrison ([04:16])

• On Human Tutors vs. AI:

  • “What I don’t think [AI] will ever solve is the accountability where it’s like when people have a real person, you know, live tutor...it’s the accountability...that helps a lot.” – Harrison ([11:21])

• On Confidence and Career Change:

  • “You just kind of quit giving a shit what people think, and you gotta put yourself out there and do it.” – Harrison ([26:32])

• On Fulfillment:

  • “When I see...a young person gain that confidence...that’s the most fulfilling thing to me.” – Harrison ([27:26])

• On Mentorship:

  • “Lean into mentorship...find somebody that’s kind of been there and done that and let them help you and guide you and save you time.” – Harrison ([46:01])

• On Process vs. Outcomes:

  • “You’re never going to be happy when you reach the destination. It’s realizing that it’s the process of getting there.” – Harrison ([20:29])

• On Business Buyouts:

  • “I’m enjoying this too much.” – Harrison on not selling his company ([30:04])
  • “I don’t want someone telling me who to have on, who I can and can’t work with. That would defeat the whole purpose of a podcast.” – Sean ([30:20])

Additional Timestamps for Important Segments

• 0:56 – 3:42: Harrison’s educational journey, ACT mastery, and origins of tutoring
• 4:16: ROI of test prep for parents and students
• 7:29: ACT vs. SAT regional trends
• 8:19 – 9:39: Test scores declining and impact of social media on attention spans
• 11:21 – 14:19: Human tutors vs. AI, tutoring as mentorship, fostering student confidence
• 16:32 – 17:14: Importance of experience in mentors and accelerated digital learning
• 18:34 – 20:03: Most influential books and learning recommendations
• 20:02 – 21:23: Chasing fulfillment versus money
• 26:31 – 28:12: Overcoming fear in career pivots, building confidence through small wins
• 29:39 – 31:02: Industry consolidation and the downsides of selling a mission-driven business
• 39:21: The necessity of personal branding in the era of AI
• 46:01 – 46:14: Harrison's closing advice to young listeners

Tone & Language

• Conversational, direct, motivational
• Sean is candid, self-effacing, and open about his journey and lessons
• Harrison is earnest, encouraging, and passionate about helping others achieve their goals

Closing Message

Harrison’s final words to listeners:

“To any young people out there...just stop caring what people think. Do what you’re truly passionate about...Lean into mentorship, find somebody that’s kind of been there and done that and let them help you and guide you and save you time.” ([46:01])

For Parents and Students:

• Visit highpreptutoring.com to explore self-paced virtual courses and personal tutoring options by Harrison’s team.

This episode is a must-listen for anyone interested in education, entrepreneurship, personal growth, and navigating unconventional career changes with confidence and impact.