Side Hustle Pro

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

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 TakeawaysBurnout is misalignment, not overworkWhy stepping back from being the face of your brand can grow your businessFinancial wholeness vs. financial freedom: which goal actually serves youHow to release financial shame and start your money journey without going it aloneHighlights Include00:00 - Tiffany’s burnout: blood pressure spikes, Oura Ring stress alerts, and a back that gave out03:00 - The thing she finally said out loud and how it shifted her physical pain08:10 - Why her COO reframed burnout: it’s not hard work, it’s misalignment10:54 - Zone of excellence vs. zone of genius21:17 - Transparent look at Budget Nista’s revenue journey from a $10M peak to today’s upswing23:41 - The B2B contract pivot: Newark schools, United Way, and NYC Dept of Education43:38 - Wealth guilt, giving beyond the overflow, and learning to drink from your own cup48:08 - A three-part framework for starting your financial journey: community, voice, and vision56:50 - Financial wholeness explained: the 10 pillars and why this goal is for everyone01:01:30 - 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 sabbaticalLinks Mentioned in This EpisodeGet Good With Money: getgoodwithmoney.comThe Big Leap by Gay Hendricks (recommended by Tiffany)Watch & ListenWatch 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/sidehustleproSocial MediaTiffany Aliche's Instagram: @thebudgetnistaSide Hustle Pro - @sidehustlepro

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

I sat down with Monica Cornitcher, CEO and co-founder of Medase Cocktails, a premium non-alcoholic beverage brand redefining what it means to drink without alcohol. What started as a simple desire for a real cocktail experience without the after-effects turned into a six-figure investment and a fast-growing brand that’s now catching the attention of major retailers.Monica shares how she and her co-founder Inga Dyer went from Zoom conversations during the pandemic to building a fully developed beverage company. Instead of rushing the process, they leaned into research, worked with a food scientist, and built a five-year strategy before launching. Their focus was clear: create authentic, full-flavor cocktails that people actually recognize and crave.In this episode, Monica opens up about the real cost of building a physical product, navigating grief after losing her co-founder, and the strategy behind growing through direct-to-consumer before entering retail. This is a powerful conversation about resilience, intentional growth, and building a brand rooted in purpose and community.Main TakeawaysWhy taking time to validate your idea and build a strategy can save you costly mistakesHow to approach launching a physical product without cutting corners on qualityThe importance of direct-to-consumer growth before entering retailHow resilience, grief, and purpose shaped the future of Medase CocktailsHighlights Include00:00 – Introduction to Medase Cocktails03:00 – Monica’s first business and corporate background06:00 – The idea sparked during COVID and building with intention08:00 – Why they worked with a food scientist instead of DIY10:00 – Creating a 5-year business strategy before launch13:00 – Identifying their target consumer and product positioning21:00 – Funding the business with $100K+ of personal investment26:00 – Attending Expo West and attracting investors29:00 – Navigating grief after losing her co-founder30:00 – Growth on Amazon and direct-to-consumer success33:00 – Why retail is expensive and how to prepare for it45:00 – Lessons from production mistakes and product quality control47:00 – Competing in a growing non-alcoholic beverage market50:00 – Lightning round insights and toolsLinks Mentioned in This EpisodeSave the Date: Start the Podcast That Builds Your Exit Plan (Friday, May 15)Watch & ListenWatch 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: @medasecocktailsTikTok: @medasecocktailsFacebook: Medase CocktailsSide Hustle Pro – @sidehustleproSideHustlePro

In this episode, I’m joined again by Monique Shields, and this conversation felt like therapy, coaching, and truth-telling all in one. We went deep into something I’ve personally been navigating: what it actually looks like to move out of survival mode as a high-achieving woman, especially when life has been life-ing.We talked about the invisible weight many of us carry, from parenting to business to unexpected life challenges, and how that impacts the way we show up, make decisions, and even spend money. One of the biggest shifts for me? Realizing I wasn’t telling myself the full story about what I had been carrying and surviving.Monique breaks down how our mindset around scarcity, energy, and outsourcing can keep us stuck, and what it really means to “resource yourself” instead of just pushing through. If you’ve been feeling stuck, foggy, or like you’re doing everything but still not moving forward, this episode will hit home.Main TakeawaysYou’re not behind, you’re likely operating without acknowledging everything you’ve been carryingScarcity mindset after a hard season can quietly shape your decisions and keep you stuckYour energy, not just your time, is one of your most valuable assetsResourcing yourself (mentally, physically, strategically) is essential for growthHighlights Include00:00 – Reconnecting with Monique and what she’s been building02:30 – Why intimate spaces and coaching containers matter04:30 – Starting YouTube and breaking through creative burnout06:00 – The hidden impact of hard seasons on decision-making08:00 – Why you’re not telling yourself the full story10:00 – High-achievers and the trap of self-pressure12:30 – Why “feeling less overwhelmed” isn’t the right goal15:00 – Scarcity mindset after financial or life shocks18:00 – Why cost-first thinking keeps you stuck21:00 – The “delusional belief” successful people hold about their future27:00 – The real value of your time and energy33:30 – What actually changed after hiring support36:00 – Mental fog and why you don’t even realize you’re in it40:00 – Why stability is not the same as hoarding43:00 – What it really means to “resource yourself”46:00 – The importance of having multiple “brains” supporting you50:00 – Why your nervous system needs support in today’s world52:00 – Reframing “I can’t afford it” into a choiceLinks Mentioned in This EpisodeSave the Date: Start the Podcast That Builds Your Exit Plan (April 17)Watch & ListenWatch 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: @moniquershieldsPodcast: Ambition Without CompromiseSide Hustle Pro – @sidehustlepro#SideHustlePro

This episode is one of the most personal and vulnerable conversations I’ve ever shared. I’m opening up about my journey as an autism mom, from the early days of pregnancy and motherhood during the pandemic to navigating the realities of developmental delays, diagnoses, and advocacy. What started as subtle concerns about speech delays turned into a life-changing journey through early intervention, therapy, and eventually receiving an official autism diagnosis for my son. Along the way, I’ve had to learn how to advocate fiercely, navigate complex systems, and redefine what motherhood looks like for me and my family.This episode is about the hard moments, the emotional weight, and the unexpected beauty in this journey. It’s also about community, resilience, and learning to see strength in a path that looks different than what I once imagined.Highlights Include00:00 – Why this episode is deeply personal02:00 – Pregnancy, birth, and early milestones during the pandemic04:30 – First signs of speech delay and comparing developmental milestones06:30 – The emotional impact of early evaluations07:30 – Starting early intervention: speech and occupational therapy09:00 – Transition to specialized preschool and navigating the system11:00 – The hidden challenges of parenting a child with special needs12:30 – Communication barriers and emotional regulation as a parent14:00 – The moment I realized how much I’ve been carrying16:40 – Understanding gestalt language processing19:30 – Getting an official autism diagnosis21:00 – Advocating for my son within the school system23:30 – A “guardian angel” moment that changed everything27:00 – The role of faith in navigating this journey29:00 – Finding community and learning from other moms30:30 – Lessons autism has taught me about boundaries and perspective31:00 – A real-life parenting moment at the barbershop33:00 – Choosing celebration during Autism Awareness MonthLinks Mentioned in This Episode• Save the Date: Start the Podcast That Builds Your Exit Plan (Friday, April 17)Watch & ListenWatch 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 MediaSide Hustle Pro – @sidehustlepro#SideHustlePro

If you’re a side hustler or solopreneur, taxes can go from simple to overwhelming real fast and the truth is, many entrepreneurs are quietly losing thousands of dollars just by not knowing what they don’t know. In this episode, I sat down with CPA and TurboTax Expert Lisa Greene-Lewis to break down the most common tax mistakes side hustlers make, from choosing the wrong business structure too early to missing out on key deductions and failing to stay organized throughout the year. We also unpack what actually makes taxes more complex as your business grows and how to stay ahead of it before tax season hits.This conversation is all about helping you feel more confident, more prepared, and more in control of your finances. Because the goal is not just to make money in your business but to keep more of it.Main TakeawaysLack of consistent tracking is the biggest mistake that leads to overpaying taxesMany solopreneurs miss deductions simply because they are unaware of what qualifiesStaying organized year-round is the key to reducing stress and maximizing savingsHighlights Include00:00 – Introduction to tax season for solopreneurs02:00 – Lisa’s journey into tax expertise and entrepreneurship05:20 – LLC vs S corp: what you actually need to know08:20 – When taxes start to feel complicated09:30 – Why tracking income and expenses is critical11:40 – Common deductions people miss13:00 – Home office deduction explained14:20 – Section 179 and equipment write-offs15:10 – What you can’t deduct (clothes, hair, makeup)16:40 – Business credit card interest deduction17:20 – Employing your kids as a tax strategy18:00 – SEP IRA and retirement savings for entrepreneurs19:00 – Qualified Business Income deduction20:10 – Key tax law updates and 1099-K changes23:20 – How to stay organized with QuickBooks25:40 – How TurboTax experts support business owners27:10 – Lisa’s personal system for staying organized Links Mentioned in This EpisodeTurboTax: https://turbotax.com/business QuickBooks: https://quickbooks.intuit.comWatch & ListenWatch 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 MediaLinkedIn: https://www.linkedin.com/in/lisa-greene-lewis-7721b815a Website: https://turbotax.com/business Side Hustle Pro – @sidehustlepro#SideHustlePro

If you’ve been waiting for the perfect moment to finally start that thing you said you’d do this year, this episode is your wake-up call. Because the truth is, that moment isn’t coming.This week, I’m pulling back the curtain on a very real, very messy week in my life and sharing why I decided to hit record anyway. From sick kids to mental clutter to a house that is far from organized, I had every reason to wait. But instead, I leaned into a powerful reminder: progress doesn’t require perfection.In this episode, I walk you through the mindset shifts that have helped me move through overwhelm, take action with limited time and energy, and stop letting the idea of “feeling ready” delay my goals. Because sometimes the real work isn’t the task itself, it’s learning how to show up before everything feels aligned.Main TakeawaysWaiting for the perfect time will keep you stuck longer than just starting messyYou have to work with the time and energy you actually have, not what you wish you hadNaming what’s holding you back helps you move through it fasterThe real growth often comes from managing your mindset, not completing the taskHighlights Include00:00 – Why I recorded this episode despite not feeling ready02:10 – How “unexpected” life moments keep disrupting plans04:18 – Learning to work in chaos instead of waiting for order05:30 – Lowering the bar to get started06:10 – Work with the time you have, not the time you wish you had08:00 – Managing your energy to show up at your best10:15 – Why naming the problem helps you move forward11:43 – Recognizing the season you’re in and adjusting expectations14:00 – Are you truly blocked or just thrown off?16:12 – How accountability helped me launch Side Hustle Pro18:36 – Overcoming imposter syndrome in a career leap21:22 – The hidden cost of needing to “have it all together”23:21 – Why perfection delays your income and growth26:24 – Maybe the real goal is mastering your mindset29:19 – Adjusting expectations so you can move forwardLinks Mentioned in This EpisodeSave the Date: Start the Podcast That Builds Your Exit Plan (Friday, April 10th)Watch & ListenWatch 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 MediaSide Hustle Pro – @sidehustlepro#SideHustlePro

One of the biggest misconceptions I see when it comes to making money is the belief that you need to start from scratch. A new certification, a brand new idea, or a completely different skill set. But the truth is, most of us already have everything we need. The real problem is not a lack of knowledge, it is not knowing how to package and position what we already know.In this episode, I break down five simple and practical ways to turn your existing skills, experiences, and knowledge into income. Whether you are in between roles, exploring a side hustle, or just trying to make extra money right now, this episode is your reminder that there is value in what you already bring to the table.I also walk through a key mindset shift. You do not need to be the top expert. You just need to be a few steps ahead of the person you are helping. People are not just paying for information. They are paying for clarity, speed, guidance, and confidence. And that is where your opportunity lies.Main TakeawaysYou do not need new skills or certifications to start making moneyThere are five core ways to monetize what you already knowPeople pay for clarity, speed, and guidance, not just expertiseStart with one path and keep it simple instead of trying everythingHighlights Include00:00 – The biggest misconception about making money01:30 – Why you already have valuable, monetizable knowledge02:00 – The 5 ways to make money with what you know03:00 – The mindset shift you need before starting04:00 – Service and coaching as the fastest path to income06:00 – Done-for-you services and why people pay for convenience08:00 – Creating simple digital products that sell10:30 – Workshops and why people pay for real-time learning13:00 – Why reminders are key when selling anything15:00 – Using content to create opportunities and income18:00 – How to use AI without losing your voice21:00 – Why you should pick ONE path and start nowLinks Mentioned in This EpisodeSave the Date: Start the Podcast That Builds Your Exit Plan (Friday, March 20)Watch & ListenWatch 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 MediaSide Hustle Pro – @sidehustlepro#SideHustlePro