Are you letting everyone else's opinions shape your decisions?
On this episode of Don't Do That, Kelly Waltrich sits down with Penny Phillips, Founder of Journey Strategic Wealth, for a brutally honest conversation about entrepreneurship, motherhood, and building a financial advisory firm. Fresh off maternity leave with a three-month-old, Penny shares her unfiltered thoughts on the evolving financial services landscape, the challenges of being a woman in leadership, and why listening to too many opinions can derail your success. From the irony of independent advisors rolling up to PE-backed firms to the importance of trusting your instincts over external noise, this conversation doesn't hold back on the messy realities of modern-day business leadership.
Kelly and Penny cover:
00:00 Introductions and Penny’s return to work after having a baby
01:30 The productivity boost of new parents and Parkinson’s Law
03:09 Penny’s background coaching advisors and her founder journey
05:31 Launching Journey East to give advisors “the best of all worlds”
06:34 Industry irony: Independent advisors rolling into big firms
08:28 Why ex-independents leading mega firms might be the answer
10:26 Journey’s mission: Lifestyle practices that scale like enterprises
12:30 The model: Back/middle office infra + coaching
13:47 Would she recommend the industry to her daughter?
15:55 Critique of women’s conferences and prepping women for real challenges
18:14 Penny’s “Don’t Do That”: Don’t listen to too many people
20:13 Her story: How seeking too many opinions crushed her confidence
22:11 Telling real feedback from noise
24:44 Be obsessed with the problem, not the solution
25:52 The reality of PE money in wealth management
26:30 Smart vs. sloppy acquisitions
27:00 Final thoughts: Trust your instincts and form your own views
Connect with Penny Phillips
About Our Guest:
Penny Phillips has spent most of her career coaching and consulting financial advisors and institutions. She is the co-founder and President of Journey Strategic Wealth, a Registered Investment Adviser built for advisors seeking independence and hands-on practice management support.
Prior to founding Journey, Penny founded Thrivos Consulting, a practice management coaching company. She has worked in various leadership positions across the financial services industry and has authored multiple practice management training programs focused on helping financial advisors build better businesses and prepare for the next generation of wealth holders.
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