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Side Hustle Pro

514: From Tutoring Classmates in High School to $1M College Prep CEO w/ Janae Young

Side Hustle Pro

Nicaila Matthews Okome | Side Hustle Pro Media

Blackpodcast, Sidehustlepro, Blackwomenownedbusiness, Entrepreneurship, Nicailamatthewsokome, Blackentrepreneurs, Sidehustleshow, Smallbusinessshow, Smallbusinessowners, Smallbusinesspodcast, Marketing, Sidehustle, Blackownedbusiness, Blackwomenentrepreneurs, Business, Sidehustles, Businesspodcast, Blackwomen

4.7 • 1.8K Ratings

🗓️ 15 May 2026

⏱️ 76 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

In this episode, I sat down with Janae Young, founder and CEO of Young College Prep, who started her first business at just 15 years old, tutoring classmates out of her school library in Wilmington, North Carolina. By the time she graduated high school, she had a team of eight tutors. By the time she graduated from Stanford, she had hit $300K in annual revenue. And by 2025, she crossed her first million.


But Janae's path was anything but linear. COVID wiped out the SAT/ACT prep market practically overnight, and her company went into negative profit. She was a freshman in college, going through a breakup, studying computer science remotely and somehow she held on. What she shares in this episode about staying stubborn in the quiet moments, investing $25K in herself as a 19-year-old college student, and pivoting her business model to serve parents instead of students is the kind of transparency you don't often hear.


Janae also opens up about navigating the college admissions landscape in a post-affirmative action era, why she believes the college application process is a metaphor for life, and how she's helping students of color tell their stories powerfully. If you're an entrepreneur in a side hustle chapter or a parent thinking about your kid's future this one is for you.



Main Takeaways

  • Invest in yourself before you feel ready: Janae wired $25K to a mastermind as a 19-year-old college student with almost nothing left in her account and that bet changed everything.


  • Know who actually holds the decision and the wallet: When Janae shifted her focus from students to parents, her revenue took off.


  • Real urgency comes from the problem, not just the deadline: Make your client deeply aware of what inaction is costing them for Janae's audience, that's potentially $100K+ in lost merit scholarships.


  • Selling is just teaching: When you see yourself as an educator first, the "sleazy" feeling disappears and you become a genuine guide.



Highlights Include

  • (0:38) Janae started her tutoring business at 15 because she was too young to work at Chick-fil-A
  • (3:26) Hiring and firing her first employee at 16 -- including a tutor who poached a client and cited contract law to get away with it
  • (11:12) How COVID wiped out the SAT/ACT market overnight and sent her business into negative profit
  • (22:43) Screen recording a webinar, then closing 4 out of 5 people at $500 the very next night
  • (27:28) Wiring $25K to a mastermind at 19 -- and the phone call her mom got from the bank
  • (31:21) Why shifting her target from students to parents changed her revenue trajectory
  • (36:27) How she structured her Stanford schedule to be a student Mon-Wed and a CEO Thu-Fri
  • (39:30) Breaking down her two offers: Ivy League Score ($2,500) and Ivy League Acceptance ($12K)
  • (51:00) Her organic and paid marketing mix: podcast, ads, and live and evergreen webinar funnels
  • (1:03:46) Her response to the affirmative action ruling and how she helps students of color own their story



Links Mentioned in This Episode



Watch & Listen

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Transcript

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0:00.0

It's in those quiet moments with yourself.

0:01.6

There's no one around.

0:03.1

And that's when you could give it.

0:04.4

And that's where you could quiet quit. That's when you could say, I'm just going to move on from that chapter of my life. That's when your most audacious belief is required. That's where you have to dig in. That's where you have to talk to yourself. And so I'm going on these walks with myself and in my head. And I'm like, if you just don't quit here, you'll build the

0:21.1

grit that you need for every chapter after.

0:24.5

You're listening to Side Hustle Pro, the podcast that teaches you to build and grow your side hustle

0:30.4

from passion project to profitable business. And I'm your host, Nikaela Matthews Okome. So let's get

0:36.8

started.

0:48.3

Today's guest is the definition of start where you are, use what you have, and do the damn thing, no matter how old you are. So at just 15 years old, Janay Young started tutoring classmates and turned that into a business before she even graduated high school.

0:56.3

She went on to attend Stanford University, scaled that side hustle through college, survived a full business crash during COVID, and rebuilt it into a million-dollar company.

1:07.4

Today, through Young College Prep, she's helped students earn over seven million in scholarships

1:11.8

and getting to top schools across the country. In this episode, we talk about building before

1:17.4

you feel ready, what it takes to keep going when things fall apart, and how Jenae turned her own

1:23.8

journey into a business. So let's get right into it.

1:34.2

So, Janae, welcome, welcome to the guest chair. I am delighted to have you here.

1:42.5

So excited to be here. Now, I am just so incredibly impressed by your journey. I cannot believe it.

1:47.8

I just in reading over your background and everything about you again, I just cannot like believe that you got started so young.

1:50.8

So you started your business at 15 years old, right?

1:53.9

Back in Wilmington, North Carolina.

1:55.8

Yes.

1:56.1

Can you walk us back to that moment?

1:59.0

Like what did you actually see in your community that made you say,

...

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