Cut The Tie Podcast with Thomas Helfrich
Episode 268

Jayla Siciliano walked away from the entrepreneurial dream everyone chases—funding, Shark Tank success, high-growth business—only to realize she had built a life that didn’t align with what actually mattered to her. In this raw and relatable episode of Cut The Tie, host Thomas Helfrich sits down with Jayla to explore the emotional cost of chasing the wrong version of success, and how she pivoted to build a life—and business—on her own terms.

Now the founder of Atlas Group and host of the Seed Money podcast, Jayla shares insights from raising capital during a recession, navigating burnout, and helping founders rethink how they approach fundraising and alignment. This episode is a must-listen for anyone grinding through startup life and wondering, Is this really worth it?

About Jayla Siciliano:

Jayla is a corporate-turned-entrepreneur who built and exited a venture-backed beverage company, landed a deal with Mark Cuban on Shark Tank, and then realized she had lost herself in the process. Today, she runs Atlas Group, a luxury short-term rental company, and hosts Seed Money, a podcast that demystifies fundraising from a founder’s perspective. Through coaching and community, she helps early-stage entrepreneurs fundraise smarter—without losing themselves.

In this episode, Thomas and Jayla discuss:

• Why “success” can become a trap
  Jayla opens up about letting investor goals override her personal goals—and what it took to reset.
• How misalignment leads to burnout
  She describes the toll of building a company that didn’t match the life she actually wanted.
• The power of one courageous moment
  Jayla shares the exact moment she knew she had to change her entire trajectory.
• How she raised $1M with no traction
  From sticky notes to Shark Tank, Jayla unpacks the persistence it took to raise money as a first-time founder.
• What most founders get wrong about fundraising
  Hint: it’s not about more slides—it’s about clarity, confidence, and alignment.

Key Takeaways:

• If the dream doesn’t fit, it’s not your dream.
  Build a business that aligns with your personal values, not just investor expectations.
• Burnout isn’t a badge of honor.
  Hustle without purpose is just exhaustion in disguise.
• Your pitch must be simple, clear, and investor-ready.
  You’ve got 30 seconds—don’t blow it with jargon or ambiguity.
• Saying “no” is how you protect your “yes.”
  Focus is everything when the opportunities start pouring in.
• Alignment isn’t a luxury—it’s the foundation.
  Start with your life goals, then build the business around them.

Connect with Jayla Siciliano:

💼 LinkedIn: Jayla Siciliano
🎙️ Seed Money Podcast
📅 Book a free pitch deck feedback session via her LinkedIn

Connect with Thomas Helfrich:

🐦 Twitter: @thelfrich
📘 Facebook: Cut The Tie Group
💼 LinkedIn: Thomas Helfrich
🌐 Website: cutthetie.com
📧 Email: [email protected]
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