Josh Simons has been building businesses since most kids were just building sandcastles. Lemonade stands. Go-karts he leased out. Hustles that taught him early how money moves and how people work.

At 17, Josh dropped out of school and made a feature film, not just for fun, but as a real business. Budgets. Hiring. Deadlines. Pressure. It was his first crash course in entrepreneurship, and it burned him out just as fast as it lit him up. In his early twenties, he hit reset mowing lawns, cleaning toilets, and actually living life for a minute.

Then music pulled him back in. Josh started a band and naturally ran the business behind it too. That’s when he saw a massive gap in the industry: musicians had platforms to stream, monetize, and build audiences… but nowhere to actually connect. LinkedIn wasn’t built for creatives.

So he built what didn’t exist.

VAMPR - the “Tinder for musicians.” A hyper-granular networking platform that grew to over 1.7 million users and changed how artists collaborate globally. That success eventually led to a strategic exit into Australia’s public music tech ecosystem with Vinyl Group, turning VAMPR into part of a broader music technology portfolio.

But Josh’s real superpower isn’t just ideation, it’s evolution. He knows teams change as companies scale. Skillsets shift. Ego gets shelved. Transparency wins.

From bootstrap hustle to tech exits, Josh Simons proves one thing: the path isn’t clean but resilience compounds. And the entrepreneurs who survive the dark chapters are the ones who end up rewriting industries.

Subscribe to Young Boss with Isabelle Guarino wherever you get your podcasts, and be sure to like, share and follow on Instagram and TikTok.

And remember, youth is your power.

Jealousy in leadership is rarely loud. It is subtle, quiet, and often disguised as “being careful.” But underneath it is fear. Fear of being replaced. Fear of being outshined. Fear of no longer being the smartest person in the room.

In this episode, we unpack why that mindset is one of the biggest threats to business growth and why hiring “safe” might feel comfortable but ultimately caps your potential. When leaders choose assistants over experts, delegate tasks but not authority, and hoard decisions to stay irreplaceable, they do not become indispensable. They become the bottleneck.

True leadership looks different. It means hiring people who challenge you. People who are stronger where you are weaker. People who can take their hands off parts of the business so you can focus on building what is next.

Scaling requires trust. Freedom requires letting go. Legacy requires a team that does not need you in every room.

This conversation is a call to audit your leadership honestly. Are you hiring to grow or hiring to stay in control? Are you surrounding yourself with comfort or with excellence?

A real Young Boss is not trying to be the best in the room. They are building rooms where greatness thrives.

Drop the ego. Hire the A-players. Let them raise your ceiling until it becomes your new floor.

Subscribe to Young Boss with Isabelle Guarino wherever you get your podcasts, and be sure to like, share and follow on Instagram and TikTok.

And remember, youth is your power.

From layoff to $2M, Elina's Young Boss journey proves youth is your power in entrepreneurship! 🚀 In this inspiring conversation, Elina reveals how she turned job loss into the launchpad for Dude Woof, a 7-figure brand built on grit, creativity, and authentic connections. With no product, no plan, and just a dream, she tackled her challenges head-on, choosing to serve doodle owners with innovative, chemical-free grooming solutions. 

Discover practical advice on leveraging social media, connecting with your audience, and scaling your business strategically—even with limited resources. From overcoming self-doubt to using AI and community feedback to drive growth, Elina shares actionable lessons for young entrepreneurs looking to turn passion into profits. 

This episode is packed with unique experiences, financial literacy tips, and the mindset shifts needed to thrive in business. Whether you’re just starting out or looking to scale, Elina’s story will empower you to embrace your potential and take bold steps toward the success you deserve.

Join the Young Boss movement and celebrate the power of ambition and innovation! Don’t forget to like, share, and follow us on Instagram and TikTok for more empowering stories and success strategies. Your youth is your power—make it count!

#tiktokgrowth #femalefounder #tiktokmarketing #youngentrepreneur #ecommercesuccess

CHAPTERS:
00:00 - Intro
00:34 - Elina's "Now or Never" Moment
01:34 - Interview with Elina, Founder of Dude Woof
05:31 - The Power of Social Media Marketing
06:31 - TikTok Shop Strategies
08:40 - Calculated Risks and Financial Understanding
10:30 - Growth Through Feedback and Improvement
12:07 - Financial Success and Business Performance
13:48 - Personal Pride in Entrepreneurial Journey
15:48 - Biggest Personal Growth Moments
16:56 - Family Support in Business Journey
18:13 - Mentorship and Community in Entrepreneurship
20:24 - Future Plans for Dude Woof
22:28 - Youth in Business: Advantages and Disadvantages
25:00 - OUTRO

Subscribe to Young Boss with Isabelle Guarino wherever you get your podcasts, and be sure to like, share and follow on Instagram and TikTok.

And remember, youth is your power.

Let’s be real: every sales pro has slipped into at least one of the 7 Deadly Sins of Sales. I sure have. I’ve over-talked. I’ve rushed into price. I’ve gotten too friendly and completely sabotaged my authority. And every time, it cost me the sale.

These sins are sneaky. They creep in when you’re nervous, excited, or unsure. They derail deals, weaken confidence, and leave you replaying every word wishing you could redo the call. But here’s the good news: if you can spot the sin, you can stop the sin.

The fastest way to lose a deal? Leave a question hanging. If an objection lingers in your client’s mind, they won’t buy. And blurting out pricing before the value is crystal clear? That’s a revenue death sentence. Clients don’t inherently know why your price makes sense — you must build the value first.

And yes — your clients want to like you, but they need to respect you. Leading like a friend instead of a professional makes pricing feel negotiable. Suddenly, you’re discounting and defending instead of confidently closing. Because if you’re talking more than your client, you’re selling yourself… not the solution.

Sales is a listening game. And if you’re not uncovering a real pain point — a reason to buy today — don’t be shocked when they say they “need to think about it.” Even worse? Waiting until the end to handle objections. By that point, you’re on defense.

The thread that ties all seven sins together? Not listening deeply enough.

When you avoid these traps, selling becomes smoother, stronger, and way more successful. You’ll stop chasing, start leading, and close with authority every single time.

Subscribe to Young Boss with Isabelle Guarino wherever you get your podcasts, and be sure to like, share and follow on Instagram and TikTok.

And remember, youth is your power.

Uncover how young entrepreneurs can turn everyday interactions into recruitment opportunities. In this inspiring conversation, Isabelle Guarino shares practical advice, unique experiences, and actionable strategies to help you build your dream team and break through the barriers holding your business back. Learn why youth is your power and how adopting a talent scout mindset can transform your business journey. From spotting potential in unexpected places like drive-thrus and webinars to asking the right questions even when you're not hiring, this episode is packed with success stories and insights that will empower you to recruit top talent and thrive in entrepreneurship. You’re not just running a business—you’re building a legacy. 

Stay inspired, stay sharp, and always be scouting for talent! Like, share, and follow Young Boss on Instagram and TikTok for more empowering episodes. Subscribe now to fuel your ambition and take your business to the next level!

CHAPTERS:
00:00 - Introduction
01:09 - Interview Tips for Success
04:37 - Identifying Talent in Real Life
06:38 - Everyday Life Recruiting Strategies
09:40 - Finding the Right Candidates
11:19 - Conclusion and Key Takeaways

Subscribe to Young Boss with Isabelle Guarino wherever you get your podcasts, and be sure to like, share and follow on Instagram and TikTok.

And remember, youth is your power.

Growing up in a traditional Hispanic household, Jeanette Miranda Davila was taught the “safe path”: go to school, get a stable 9–5, and never risk security. But deep down, she always felt called to something more - something creative, something freeing, something hers.

She chased that calling into the entertainment world, but motherhood shifted her again. She wanted presence, purpose, and a community that didn’t yet exist. So she created one. Rooted In Her was born from her desire to support women navigating life transitions with honesty, vulnerability, and real connection.

But her journey wasn’t linear. After rapid growth (monthly events, community building, countless women served) Jeanette hit burnout. She felt drained, unseen, and taken advantage of. So she stepped back. Prayed. Journaled. Asked herself what she truly wanted.

And the answer was clear: Build a real business. Build her own path.

Leaving Divas Local was her wake-up call. Women weren’t showing up for the brand—they were showing up for her. That realization fueled her comeback.

Today, Jeanette is a paid speaker, community builder, and the visionary behind a thriving membership of women committed to collaboration over comparison. With a growing team and expanding events, Rooted In Her is becoming more than a community, it’s a movement.

Her mission? Inspire women to recognize their worth, break cultural cycles, and embrace bold dreams.

Because when women feel seen, supported, and rooted in who they truly are, anything is possible.

Subscribe to Young Boss with Isabelle Guarino wherever you get your podcasts, and be sure to like, share and follow on Instagram and TikTok.

And remember, youth is your power.

When Snawing Alvarado came to the Bronx from the Dominican Republic at eight years old, he thought snow meant success. Instead, it meant Section 8 housing, roaches, and a basement that smelled like broken promises. The “American Dream” wasn’t what it looked like on TV — it was crowded apartments, tired parents, and the quiet pressure to make it out.

Snawing became the first in his family to graduate college and land a “good job” as an ICU nurse. But three months in, the dream cracked. Long hours. Miserable pay. No freedom. He realized he wasn’t chasing purpose — he was chasing a paycheck.

So he bet on himself. He left nursing, flipped his savings into real estate, and built multiple care homes that now cash-flow over $20K a month. But the bigger the numbers got, the more he realized: money isn’t peace. The grind cost him relationships, sleep, and moments with the people who mattered most.

Today, Snawing’s success isn’t defined by dollar signs — it’s defined by balance. Coaching others, salsa dancing, spending time with family — that’s the real wealth.

Because the American Dream? It’s not free. It’ll take your comfort, your time, and sometimes your heart.

But if you pay the price with purpose, it’s worth every cent.

Subscribe to Young Boss with Isabelle Guarino wherever you get your podcasts, and be sure to like, share and follow on Instagram and TikTok.

And remember, youth is your power.

Are you ready to embrace the mindset every young boss needs to win? In this inspiring conversation, Isabelle unpacks the lessons from "Who Moved My Cheese?", a masterclass in mindset for young entrepreneurs. Discover how adaptability, curiosity, and innovation are key to navigating the ever-changing maze of entrepreneurship. Whether it's shifting platforms, evolving products, or understanding market trends, this episode offers practical advice to keep your business ahead and thriving.

Through unique experiences and relatable scenarios, Isabelle empowers you to identify your "cheese," recognize when it's moving, and pivot with confidence. Learn how to fail fast, stay alert to change, and turn discomfort into growth. From financial literacy to personal development, this episode is packed with actionable insights every young boss needs to conquer their business journey. 

Youth is your power, and success is about staying curious, brave, and ready to explore the maze. Like, share, and follow us on Instagram and TikTok to join the Young Boss community and keep pushing forward!

#findingsuccess #businessmindset #overcomingbusinesschallenges #businessstrategies #youngentrepreneurs

CHAPTERS:
00:00 - Intro
01:12 - The Cheese Moved
03:18 - The Cheese Didn’t Disappear
05:46 - Adaptability Equals Abundance
07:38 - Get the Book List
09:52 - Who Moved My Cheese
12:45 - Protect Your Ability to Find the Cheese
14:15 - Innovation Thrives on Momentum, Not Perfection
14:54 - Comfort Zone Challenges
16:03 - Outro

Subscribe to Young Boss with Isabelle Guarino wherever you get your podcasts, and be sure to like, share and follow on Instagram and TikTok.

And remember, youth is your power.

At 26, Hannah Kesler is teaching entrepreneurs how to build wealth like banks do — by controlling where their money lives. But her story started at Cracker Barrel, not in a boardroom.

Waiting tables at 18, Hannah learned her first business lesson: the harder she worked, the more she earned. That independence became her addiction. When college and accounting didn’t stick, her dad invited her to join The Money Multiplier — starting at the bottom doing paperwork and applications.

Then came her turning point. At 20, she got a last-minute call to replace her dad on stage in Scottsdale — 65 seasoned real estate investors waiting. Nervous but determined, she delivered. That night, she found her passion for public speaking and helping others understand money.

Today, Hannah travels the country teaching Becoming Your Own Banker, a philosophy built on using high-cash-value life insurance to create uninterrupted compounding and total control. Her message? You don’t need to work harder — you need to make your money work smarter.

But her path wasn’t handed down. Working in a family business meant hard lessons, boundaries, and proving she earned her seat. “Family dinners aren’t for business,” she says. “The business can wait.”

For Hannah, wealth starts with mindset. “You’ll never get your time back,” she says. “So take the leap, trust yourself — and get out of your own damn way.”

Subscribe to Young Boss with Isabelle Guarino wherever you get your podcasts, and be sure to like, share and follow on Instagram and TikTok.

And remember, youth is your power.

Ready to turn your freelance side hustle into a booming $20K/month studio? In this inspiring conversation on Young Boss, Isabelle Guarino chats with Ben Jackson, a solopreneur who transformed his creative hustle into a thriving boutique web development studio. Youth is your power, and Ben’s story proves that ambition, strategy, and persistence can lead to incredible success.

Learn how Ben prepared for his leap to entrepreneurship, navigated the challenges of building a business in a competitive field, and positioned himself as a standout developer in a world of cheap labor and AI. He shares practical advice on financial literacy, finding your niche, and balancing creative control with scaling your business. Whether you're a young entrepreneur or just dreaming of breaking through barriers, this episode is packed with actionable insights and motivation to fuel your journey.

Discover the power of valuing your craft, attracting the right clients, and creating a business that aligns with your lifestyle and goals. Don’t miss this success story filled with unique experiences and lessons for anyone looking to make their side hustle a full-time reality. 

Hit play, and be inspired to chase your dreams! Don’t forget to like, share, and follow us on Instagram and TikTok to stay connected with Young Boss and more episodes celebrating youth, ambition, and innovation.

#scalingbusiness #businessadvice #creativeentrepreneurship #webdevelopmentstrategies #youngentrepreneurs

CHAPTERS:
00:00 - Intro
00:35 - Preparing for Career Leap
03:20 - Selling Your Value in Competitive Market
05:45 - Scaling and Growing Your Business
08:40 - Challenges of Going Solo

Subscribe to Young Boss with Isabelle Guarino wherever you get your podcasts, and be sure to like, share and follow on Instagram and TikTok.

And remember, youth is your power.