‘Knowing Your Worth at the Table’ with Dana Jacoby - Reward Podcast Episode 44
Over $2 BILLION of deals have crossed Dana Jacoby’s desk since selling her first company, and today her strongest mission is making sure other women own the full value of what they bring to the table. (And we’re honored she’s been an incredible advisor to many of us within The Trust.)
After learning the business fundamentals at Enterprise Rent-a-Car, a serendipitous meeting led her into the pharmaceutical and medical device world, where she built a rewarding and lucrative career. After experiencing several mergers and acquisitions herself, she realized she’d had more valuable counsel during those times.
In this candid conversation, Dana reflects on the deals that shaped her, the lessons learned from undervaluing herself early on, and how those experiences now fuel her work advising women navigating high-stakes decisions.
In this episode of REWARD: The Podcast of The Trust, founder Ali Brown sits down with Dana for an honest discussion about leadership, leverage, and the power of being in rooms where women tell the truth.
On this episode of the #REWARDPodcast, you’ll hear:
Why a high-value community isn’t just “nice to have” at higher levels — it’s essential
How Dana’s dual exposure to healthcare and business shaped her entrepreneurial instincts early on
The realities of building a consulting company from the ground up — and what limited resources can actually teach you
Hard-earned lessons around knowing your value (and what happens when you don’t)
Why powerful women need safe, strategic spaces to think clearly and support one another
Dana’s perspective on authentic connection as a catalyst for better decisions and long-term growth
This is a conversation for women who are done playing small — and ready to lead, negotiate, and choose from a place of clarity and confidence.
And, learn more about The Trust and Dana!
Learn more about The Trust – our tight-knit community for 7+8-figure women entrepreneurs
Learn more about Dana’s consulting practice, Vector Medical Group
Connect with us on social using the hashtag #RewardPodcast and share your key takeaways from this episode!