Most health tech startups crash and burn within months. So what separates the ones that actually make it?In this episode, Cassie DeWalt breaks down her wild journey from selling luxury fashion at Saks Fifth Avenue to building Jooshi — a first-of-its-kind startup combining fashion psychology with mental health care. We talk about why most founders get healthcare completely wrong, the red flags she looks for when evaluating startups, and why copying someone else's playbook is a death sentence in mental health.We also get into the AI hype vs. reality in healthcare, why having a clinician on your team is non-negotiable, and how vibe coding tools are letting non-technical founders ship real products in a weekend.If you're building in health tech, thinking about starting something, or just want to hear one of the most unique founder stories out there — this one's for you.🔗 Connect with Cassie:→ positivelycast.com→ LinkedIn & Instagram: Positively Cass⏱️ Timestamps (adjust to your actual video):0:00 – From fashion to healthcare2:30 – The moment everything changed6:00 – Why most health tech startups fail10:00 – AI hype vs. what actually works14:00 – The signals of a winning company18:00 – Fashion x mental health: introducing Jooshi22:00 – Vibe coding & building without a tech background25:00 – Where to find Cassie#GoToMarket #HealthTech #MentalHealth #Startup #Entrepreneurship #AIinHealthcare #VibeCoding #FounderStory

Devreet Dulay has seen hundreds of companies chase AI tools they don't understand—and waste thousands doing it. As employee #2 at an AI automation startup and now founder of Internal Automations, she's learned the hard way: the most cutting-edge tech means nothing if you can't explain why it matters. In this conversation, we cover:→ Why "tool chasing" is killing your AI strategy→ The surprising return of in-person sales (yes, golf is back)→ How to become the AI expert at your company—even if you're junior→ What most founders get wrong about automating their workflows→ Why simplicity beats complexity every timeIf you're a founder trying to figure out where AI actually fits in your business, this one's for you.

B2B SaaS has changed. Your GTM org probably hasn’t. In this episode, I sit down with **Lissa W. Cox** (15+ years in B2B SaaS marketing, Executive MBA, former “early influencer”) to unpack how social, sales, and GTM have evolved—and what most teams are still getting wrong. We get into: - The collapse of brand trust and why polished corporate feeds don’t move the needle anymore. - Why founder-led content works… until it doesn’t—and how audiences sniff out inauthentic “personal brands.” - The trap of automation for automation’s sake (7,000 emails a day, zero revenue) and why GTM engineering should start with manual work and customer interviews. - Lissa’s hot take: GTM Engineering as the natural evolution of the SDR, not RevOps—and why the “junior” role often understands the market better than leadership. - A practical lens on product–market fit vs. go-to-market strategy, explore vs. exploit, and how over-rotating on either leads to chaos or stagnation. - Why AI and compute scarcity will force founders into real prioritization, cross-functional collaboration, and big-picture thinking. Listen in for practical GTM strategies you can use today.Larissa has also written an 86 page GTME Guidebook that gives the end-to-end process of creating a sustainable revenue flywheel. Which can be found at https://gtme-academy.com/

Are AI tools really the game-changers they're hyped to be in B2B sales, or is human touch still irreplaceable? Join us as Christian, founder of SalesSubs and seasoned B2B sales expert, shares his insights from over a decade of experience in the startup landscape. In this episode, we explore the evolving dynamics of sales strategies, the balance between traditional pipelines and AI automation, and the pivotal role of foundational sales strategy that AI simply can't replicate. Christian delves into why cold calling is making a surprising comeback, and how simple, person-to-person connections could be your secret weapon in a tech-saturated world. Discover actionable tactics, from leveraging LinkedIn for authentic outreach, to weaving human touch into automated processes.Does AI mark the end of human-led sales, or is it a tool that simply enhances well-laid strategies? Listen in for practical GTM strategies you can use today.

Brendan Herjavec: https://www.linkedin.com/in/brendanherjavec/

Website: https://brendanherjavec.com/

Kristan Servidad: https://www.linkedin.com/in/kservidad/SalesSubs: https://www.salessubs.com/