Podcast Summary: Digital Social Hour – Harrison Hightower: From Pharmacy to CEO: My Bold Career Pivot | DSH #1510
Date: August 27, 2025
Host: Sean Kelly
Guest: Harrison Hightower (Founder, High Prep Tutoring)
Main Theme
This episode explores the inspiring journey of Harrison Hightower, who made a bold pivot from pharmacy school to building a rapidly-growing tutoring company focused on standardized test prep. Host Sean Kelly and Harrison dive deep into the cultural, educational, and entrepreneurial lessons learned, the changing landscape of test prep, and the power of mentorship, mindset, and personal growth.
Key Discussion Points & Insights
1. Harrison’s Background and Career Pivot
- Small-town roots: Grew up in Jacksonville, Alabama, attended a rural county school, small graduating class (70 people) [02:24].
- Overcoming barriers: Parents couldn’t fund college; Harrison discovered ACT/SAT scholarships and self-studied to raise his score from 22 to 32, earning a full ride to Auburn University [03:29].
- Entrepreneurial spark: Started tutoring brother and classmates, founded High Prep Tutoring in pharmacy school, transitioned to full-time entrepreneur upon realizing his passion [04:22].
2. Standardized Test Prep as a Game-Changer
- ROI of test prep: Investing in test prep provides a greater return than most college funds due to scholarship impacts [04:56].
- Test-taking skill gap: High-performing students often struggle with standardized tests due to lack of targeted test strategy training in school [05:09].
- Regional differences: ACT vs. SAT preference varies by region; most universities accept both [07:27][08:09].
- Changing landscape: National test score averages are the lowest in decades; test length and format have changed to match attention spans [08:59].
3. Influence of Technology & Social Media
- Attention spans: Societal shifts, social media, and constant tech exposure have impacted students’ focus and study habits [09:14].
- Education on TikTok: Harrison leverages social media to offer educational content amidst the entertainment noise [11:04].
- AI tutors vs. human connection: While AI is growing in capability, Harrison argues human tutors provide irreplaceable accountability and motivation [12:01–13:19].
4. Mentorship, Mindset & Personal Growth
- Value of mentorship: Real-world mentors and experienced coaches are vital in both academia and entrepreneurship [16:51][17:12].
- Measuring fulfillment: Both Sean and Harrison agree that fulfillment comes from impact—helping students, clients, and team members grow rather than chasing financial milestones [22:24][29:31].
- Confidence through action: Small wins, whether at the gym or in academics, build lasting confidence [25:56][26:01].
5. The Trap of “I’ll Be Happy When...”
- Shifting mindsets: Both discuss escaping the “I’ll be happy when” mentality, emphasizing process over destination and recognizing the emptiness of tying happiness to income or achievement [20:43–21:42].
6. Business Models & Company Culture
- Personal over transactional: High Prep focuses on deep, personal relationships with clients and staff, in contrast to franchised, transactional tutoring models [13:20–14:59].
- Private equity & acquisitions: Both share wariness over selling out to larger companies or investors due to loss of control and passion [30:12–31:43].
7. Productivity, Learning & Personal Branding
- Leveraging AI and content: Sean discusses using ChatGPT to summarize books and optimize learning, as well as the importance of quality prompts [35:38].
- Top book recommendations: “How to Win Friends and Influence People,” “Atomic Habits,” “Rich Dad Poor Dad,” “100 Million Dollar Offers,” “Life Force” [19:14–20:01].
- Podcasts as learning tools: Both host and guest cite digital shows as major sources of inspiration and practical business education—Rob Dyrdek, Bradley, Huberman, Hormozi, Diary of a CEO, etc. [38:04–39:17].
- Personal brand necessity: Strong personal branding is crucial in the age of AI for relationship-building and business resilience [40:01–40:37].
Notable Quotes & Moments
On Career Transition & Self-Confidence
“You just gotta quit giving a shit what people think, and you gotta put yourself out there... When I started winning in business, then I got more confident, and that's one thing we try to do for our students—help them get those small wins.”
— Harrison Hightower [27:12, 28:52]
On ROI of Test Prep
“The ROI [of test prep] is better than any kind of college fund you could start.”
— Harrison Hightower [04:56]
On Mentorship & Authenticity
“People will always benefit from the human interaction and explanation … one thing that AI will never solve is the accountability.”
— Harrison Hightower [12:01]
“I only hire mentors with experience. For me, it doesn't matter about age or what you look like. It's all experience.”
— Sean Kelly [17:12]
On Fulfillment
“It's always when I'm focused on helping other people. Anytime I start thinking about me too much, that's when things are not aligned.”
— Harrison Hightower [29:31]
On Chasing Money vs. Impact
“I always tell people it's good to be book smart, but you want to translate those skills into the real world. It's making money, right?”
— Sean Kelly [15:04]
“I'll be happy when I hit this amount. At first it was 100k. Hit that. Then it was a million. Wasn't happy. Then it was $10 million. Most depressed I've ever been… It's never going to be enough, even if I'm a billionaire.”
— Sean Kelly [21:25]
On Overcoming Self-Doubt & Sharing
“Don't care what people think. Do what you're truly passionate about. Lean into mentorship and reach out—even if you think they won't help, most people are happy to do it. The first step is just sending the DM.”
— Harrison Hightower [46:06]
Timestamps for Major Segments
- 00:44 – 04:22 — Harrison’s backstory, academic journey, and founding the company
- 05:09 – 06:00 — Why test prep is essential, test-taking vs. being a good student
- 07:27 – 08:26 — Regional ACT/SAT preferences
- 09:14 – 10:57 — Impact of social media on attention and learning
- 12:01 – 13:44 — AI vs. human tutors and the importance of accountability
- 16:51 – 17:19 — Mentorship, experience vs. age in hiring
- 20:43 – 21:42 — The “I’ll be happy when…” trap
- 25:56 – 26:25 — Using fitness and small wins to build confidence
- 27:12 – 28:52 — Overcoming fear of judgment during career switch
- 29:31 – 30:12 — Fulfillment from seeing students and staff grow
- 31:22 – 31:58 — Challenges and risks of selling a business
- 34:51 – 36:09 — Learning to speed read & making book summaries actionable
- 38:04 – 39:17 — Favorite podcasts as growth tools
- 40:01 – 40:37 — Importance of personal branding in the AI era
- 41:29 – 43:32 — The story of how Harrison connected with Brad Lea & built his course
- 46:06 – 46:54 — Closing advice: “Don’t care what people think; lean into mentorship”
Memorable Moments
- Sean’s analogies on confidence: Comparing hiring a trainer at the gym with hiring a tutor for accountability [13:44].
- Harrison’s impact stories: Parents’ feedback about tutors being life-changing for their children, confidence blossoming in students and staff [14:59, 28:52].
- Both hosts reflecting on their introverted pasts and growth through fitness, action, and content creation [24:20–25:56].
- Harrison’s story of connecting with Brad Lea via his live call-in, which led to a mentorship and business opportunity [41:29–43:32].
Closing Messages
- Action over validation: Don’t let fear of others’ opinions dictate your path. Pursue your passions and put yourself out there.
- Mentorship matters: Seek guidance from those with experience, and be proactive in reaching out.
- Fulfillment over money: Shift focus from external benchmarks to internal impact and purposeful work.
- Personal branding is the future: In a world facing AI disruption, genuine personal connections and reputation are more valuable than ever.
Guest Links:
- Instagram: @harrisonhightower
- Company: High Prep Tutoring & Test Prep
- High Prep Academy (online self-paced ACT course)
This summary brings together the episode's motivation, practical advice, and human stories—perfect for listeners seeking inspiration for career pivots, entrepreneurship, or educational success.