FeastFast only launched in 2025, but the story behind this brand started long before its first sale. The company was founded by two doctors who were struggling with weight loss and shocked by how every store-bought “healthy” snack spiked their blood sugar. After testing product after product, they created their own — snacks that didn’t create glucose spikes. They lost over 100 pounds, discovered a massive market in diabetic and pre-diabetic consumers, and teamed up with seasoned entrepreneur Joshua Sizemore to bring FeastFast to life.

But the path has been anything but smooth. Just weeks into launch, a breach in their ad account triggered a $100K/day spending error — forcing the entire team to rebuild their ad ecosystem from scratch.

Josh’s background makes him uniquely equipped for moments like these. After scaling Shinola from $30M to $300M, relaunching Original New York Seltzer, and building a water company that once landed a $1M investment inside a bar at 2am — he’s learned what it truly takes to bring consumer products to market.

In this episode, Josh breaks down the realities of retail vs DTC, why story drives conversion, and how founders should think about margins, distribution, influencers, and affiliates. He shares unfiltered lessons from raising capital, surviving entrepreneurial lows, and why authenticity from the founder outperforms any influencer strategy.

His advice is simple: if you believe in your product, go all in. Get feedback, trust yourself, and don’t look back.

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.

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.