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Side Hustle Pro

Side Hustle Pro

De : Nicaila Matthews Okome | Side Hustle Pro Media
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 Side Hustle Pro spotlights bold black women entrepreneurs who have scaled from side hustle to profitable business. Join Chief Side Hustler turned full-time entrepreneur Nicaila Matthews Okome for your weekly installment of Side Hustle Pro and learn actionable strategies to start small and get going–wherever and whoever you are. Side Hustle Pro features interviews with inspiring Black women entrepreneurs who started out as side hustlers, including interviews with Myleik Teele, Morgan DeBaun, Tiffany "The Budgetnista" Aliche, and more!

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

    514: From Tutoring Classmates in High School to $1M College Prep CEO w/ Janae Young
    May 15 2026
    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 TakeawaysInvest 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 storyLinks Mentioned in This EpisodeYoung College Prep website: janaetutoring.comStacey Boehman -- 2K for 2K program: staceyboehman.com/2kfor2kDielle Charon -- Six Figure Liberation mastermind (formerly called Sales Queen): diellecharon.comClaire Pelitro (Claire Pels) -- Get Paid Marketing: clairepells.comAmy Porterfield -- amyporterfield.comBrooke Castillo -- The Life Coach School: thelifecoachschool.comWatch & ListenListen to the Side Hustle Pro podcast on Spotify, Apple Podcasts, and wherever you stream podcasts. Watch full video episodes on the Side Hustle Pro YouTube channel.Social MediaInstagram: @JanaeTutoringFacebook: @JanaeTutoringPodcast: The Get Accepted Podcast Hosted on Acast. See acast.com/privacy for more information.
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    1 h et 16 min
  • 513: Tiffany Aliche on What the Hard Years Teach You About Money and Resilience

    513: Tiffany Aliche on What the Hard Years Teach You About Money and Resilience
    May 8 2026

    This week in the guest chair is Tiffany Aliche, known to millions as the Budgetnista and the author of the New York Times bestseller Get Good With Money. Tiffany is back for a deeply personal conversation about what burnout actually looks like when you’re at the top of your game, and what it finally took for her to listen to herself.


    She opens up about the physical and emotional signs she ignored for too long, the scary truth she finally admitted to her therapist, and how a solo trip to Sedona shifted everything. She also takes us inside the business pivot happening at Budgetnista, from being the face of everything to stepping back and watching her company grow 74% in a single quarter.

    We also get into the deeper financial conversation: the difference between financial freedom and financial wholeness, how to release financial shame, and the two questions Tiffany now leans on in even her darkest moments. This one is rich from start to finish.



    Main Takeaways
    • Burnout is misalignment, not overwork
    • Why stepping back from being the face of your brand can grow your business
    • Financial wholeness vs. financial freedom: which goal actually serves you
    • How to release financial shame and start your money journey without going it alone



    Highlights Include
    • 00:00 - Tiffany’s burnout: blood pressure spikes, Oura Ring stress alerts, and a back that gave out
    • 03:00 - The thing she finally said out loud and how it shifted her physical pain
    • 08:10 - Why her COO reframed burnout: it’s not hard work, it’s misalignment
    • 10:54 - Zone of excellence vs. zone of genius
    • 21:17 - Transparent look at Budget Nista’s revenue journey from a $10M peak to today’s upswing
    • 23:41 - The B2B contract pivot: Newark schools, United Way, and NYC Dept of Education
    • 43:38 - Wealth guilt, giving beyond the overflow, and learning to drink from your own cup
    • 48:08 - A three-part framework for starting your financial journey: community, voice, and vision
    • 56:50 - Financial wholeness explained: the 10 pillars and why this goal is for everyone
    • 01:01:30 - Two questions to ask in your hardest moments: Is this true? Is it the only truth available?
    • 01:03:34 - Tiffany previews her upcoming book, The Gifts of Grief, and her 2027 sabbatical



    Links Mentioned in This Episode
    • Get Good With Money: getgoodwithmoney.com
    • The Big Leap by Gay Hendricks (recommended by Tiffany)



    Watch & Listen

    Watch this episode on YouTube and listen on all podcast platforms:

    • Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323
    • Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8t
    • YouTube: https://www.youtube.com/sidehustlepro



    Social Media
    • Tiffany Aliche's Instagram: @thebudgetnista


    • Side Hustle Pro - @sidehustlepro

    Hosted on Acast. See acast.com/privacy for more information.
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    1 h et 7 min
  • 512: How Leah Collins Turned Financial Mistakes Into a TV Show, Multiple Income Streams, and a Purpose-Driven Career

    512: How Leah Collins Turned Financial Mistakes Into a TV Show, Multiple Income Streams, and a Purpose-Driven Career
    May 1 2026
    This week in the guest chair is Leah Collins, financial coach, speaker, and host of Maxxed Out, a powerful series helping people confront their finances and the relationships tied to them. But Leah’s journey didn’t start on TV, it started with a moment of truth: making the most money she ever had… and realizing she had nothing to show for it.In this episode, I sit down with Leah to unpack how she transformed her own financial struggles into a thriving business, paid off $40,000 in debt, and ultimately landed her own show. We talk about the behind-the-scenes reality of building a personal brand, why communication is the foundation of financial success, and how she leveraged every opportunity to create multiple income streams.Leah also opens up about one of the most pivotal moments in her life: calling off her wedding due to financial incompatibility. That experience reshaped her entire mission and led her to focus on money and relationships, helping others navigate the conversations so many of us avoid. This episode is a masterclass in turning pain into purpose and building a life that aligns with your values.Main TakeawaysTurning personal financial struggles into a business can create powerful impact and incomeFinancial compatibility and communication are critical in relationshipsYour personal brand is always working for you, even when you don’t realize itMultiple income streams, including speaking, media, and passive products, create flexibility and freedomHighlights Include00:00 – Why money affects every part of your life02:10 – 20 years in corporate finance but struggling personally04:05 – Wake-up call: high income, no results04:40 – $100 bootcamp → $40K debt paid off05:20 – Calling off her wedding over money misalignment07:06 – Prenups, communication, and financial expectations09:05 – Turning personal pain into a business niche10:53 – Launching her brand → getting discovered for TV12:11 – Building a strategic personal brand that attracts opportunities14:17 – TV journey: rejection, delay, and eventual greenlight16:46 – Scaling after motherhood and shifting business model20:43 – Behind the scenes of Maxed Out and building trust23:03 – Leveraging TV into multiple income streams24:55 – Values-based finances and smarter decision-making26:51 – Balancing a 9–5 while growing a business29:37 – Storytelling as a tool for impact and connection31:27 – Pitching yourself and understanding media monetization34:11 – “You’re always being interviewed” mindset38:13 – Why quality beats quantity in content41:02 – Burnout, boundaries, and protecting your time41:42 – Final advice: build your business without quitting your jobLinks Mentioned in This EpisodeMoney Moves Makeover: https://www.amazon.com/OWN Network: https://www.oprah.com/ownHBO Max: https://www.max.com/Discovery+: https://www.discoveryplus.com/Save the Date: Start the Podcast That Builds Your Exit Plan (Friday, May 15)Watch this episode on YouTube and listen on all podcast platforms:Apple Podcasts: https://podcasts.apple.com/us/podcast/side-hustle-pro/id1126021323Spotify: https://open.spotify.com/show/13qDj08lBR4ymzGhXIKy8tYouTube: https://www.youtube.com/sidehustleproAnnouncementsIf you’re ready to build a podcast that becomes your exit plan from your 9-to-5, sign up for my next live class: Start the Podcast That Builds Your Exit PlanSave your seat here. Social MediaInstagram:@theleahmariecollins Side Hustle Pro – @sidehustlepro#SideHustlePro Hosted on Acast. See acast.com/privacy for more information.
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    44 min
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