From Burnout to Bi Coastal: How Jayla Siciliano Reclaimed Her Vision and Built a Life Fueled Business
If you have ever wondered what it takes to walk away from your dream and start over from scratch, this episode is going to hit home in the best way.
Jayla Siciliano is not new to big leaps. She raised her first round of seed capital without connections, scored a deal on Shark Tank with Mark Cuban, and scaled a beverage company across the country. She also experienced the kind of burnout that comes from chasing someone else's version of success.
Today, she runs a thriving luxury short term rental company with properties in Santa Barbara and Vermont. She also hosts the Seed Money Podcast, where she helps founders navigate the wild world of funding their business ideas. Her story is full of hard-won lessons, sharp pivots, and brutally honest reflections about what it means to build something that actually supports the life you want.
Here is what we unpacked in our conversation with Jayla and why every founder should hear it.
You do not need the perfect background to get funding
Jayla did not come from money. She had no connections in the alcohol industry. She left a corporate job and went all in on a wine spritzer idea that she believed in, even though the path ahead was completely uncharted. For 18 months, she pitched investors and got told no again and again. She finally landed a lead investor and raised her first half a million dollars. Then came the inventory disaster that nearly took the business down before it even began.
This was not a story of an overnight yes or a viral moment that changed everything. It was a story of grit, resourcefulness, and showing up again and again even when the path was unclear. If you are in the messy middle right now, you are not behind. You are exactly where you need to be.
Burnout will cost you everything if you do not pay attention
After her Shark Tank deal and national growth, Jayla found herself completely exhausted. The business was running but she was losing herself in the process. High blood pressure, missed milestones with family, and a total misalignment with the lifestyle she originally set out to create pushed her to make the hardest call of all — walking away.
Burnout is sneaky. It does not show up with a warning. It builds slowly until suddenly you are a stranger to your own dream. Jayla’s story is a powerful reminder that success that comes at the cost of your health, values, and joy is not success at all.
Pivoting is not failure
After winding down her beverage company, Jayla gave herself time to rest. She had a baby. She took a corporate job. She sat in the fog of burnout and slowly started to reconnect with what she actually wanted. That clarity led her to real estate. What started with one short term rental turned into a portfolio of 30 properties and a full service hospitality business that gives her both financial success and time freedom.
This is not a story about failure. It is a story about evolution. Jayla followed the signs, trusted her gut, and built something that finally aligned with her life.
Build systems. Set boundaries. Protect your time.
We asked Jayla how she balances managing dozens of luxury properties and still finds space for travel, creativity, and quality time. Her answer was simple and powerful. Systems. Tech. Boundaries. She has a lean team. A strong operations engine. Clear communication channels. No one has her personal cell number. Everyone uses the company line. The structure gives her freedom.
If you are growing a service based business, this is your cue to stop being the bottleneck. Delegate what drains you. Automate what is repetitive. Protect your energy like it is a business asset.
Confidence matters more than a perfect pitch deck
Jayla now spends time on the other side of the table, talking to investors and mentoring founders on Seed Money. Her message is clear. You do not need to live in Silicon Valley or have an MBA to raise capital. But you do need to be prepared, confident, and aligned with your story and numbers.
What separates the yes from the no is not always the size of the market or the look of your deck. It is how well you show up and speak with clarity and belief. Investors are betting on you as much as the idea. Be ready. Be honest. Be memorable.
The investor comment she never forgot
At one point in her journey, Jayla was sitting across from an investor who asked, What happens if you get pregnant. It was a throwaway line to him. But for her, it planted a seed of doubt that lingered for years.
This moment is a reminder of how subtle and harmful some of these power dynamics still are. Jayla’s message to women founders is this. Do not let their fear become your truth. Call it out. Shake it off. Keep going.
Flexibility is not a perk. It is the point.
For Jayla, flexibility means being able to go to her son’s field trips. Take Fridays off when she wants. Spend three weeks in Italy and actually enjoy it. That freedom comes from structure, team support, and a willingness to let go of control.
You do not need to wait until you reach some business milestone to make this happen. You can define what flexibility means for you and start building around that vision now.
Her guiding philosophy
Jayla left us with this. Patience and persistence. Big things take time. If you stay focused and keep going, even when it feels impossible, momentum will build. It is not about pushing endlessly. It is about staying with it long enough to let the results unfold.
If you are building something new or wrestling with what comes next, this episode will light something up in you. Jayla’s journey is a powerful reminder that it is never too late to pivot, that success is allowed to look different, and that you always get to rewrite the rules.
Ready to tune in? Listen to the full episode here
And if you loved it, leave a review or share it with a friend who needs a reminder that freedom is possible.
👀 Mentioned in the Episode
Seed Money Podcast: seedmoneypodcast.com
Follow Jayla on Instagram and TikTok: @jaylasiciliano
YouTube: @seedmoneypodcast
