Kevin Caldwell
episode 8: How to Prudently Approach Company Stock
Welcome back to Finance Lab, we are thrilled to bring you this crucial episode centered around a topic that holds immense significance for many professionals, particularly those in the tech industry. Today, we're diving deep into the world of company stock ownership. Kevin Caldwell joins Finance Lab to discuss the topic of investing in company stock, specifically restricted stock units (RSUs). We explore the balance between the substantial rewards and risks associated with company ownership, shedding light on diverse strategies, especially when facing market uncertainties.
Unraveling the complexities of restricted stock units (RSUs), a popular form of equity compensation, Kevin also dissects the nuances between RSUs and traditional stock options. As we navigate hypothetical scenarios and real-world challenges, Kevin provides actionable advice on tax planning, emphasizing the importance of proactive rather than reactive strategies tailored to your unique circumstances. We work to explain the mysteries around taxes, discussing how to optimize your gains and offset losses, ensuring you make informed decisions, not just reactive ones.
Join us as we empower you with the knowledge and strategies necessary to approach your company stock ownership with confidence. Remember, your financial future shouldn't be dictated by market whims; it should be driven by a well-thought-out plan!
Listen to full episode:
Key Moments:
1:04: Importance of managing company stock ownership
1:59: Our guest today is Kevin Caldwell of Golden Road Advisors.
3:59: Taxes on restricted stock units (RSUs)
5:10: Importance of having a strategy for company stock
6:04: Proactive planning is vital for navigating volatile stock values and tax implications.
7:38: Plan what to do before shares vest
8:15: Hear about how tech stocks faced challenges in 2022.
9:32: What does Kevin mean by “behavioral tool”?
9:36: Strategy of selling shares at vesting to lower tax implications
11:16: Discussion on the current tech stock rally in 2023
12:44: Kevin argues that being proactive is essential; control your investments wisely, considering goals and diversification.
14:17: We are encouraged to develop a proactive plan and to avoid reactive market-driven decisions.
16:32: Kevin dives into a discussion around stock vesting.
18:19: Each RSU grant has unique tax consequences based on price.
20:47: We should aim to strategically time tax payments, considering market conditions and personal finances.
22:06: Tax-Loss harvesting can be used to offset gains in the future
23:40: The key is to develop a plan for company stock ownership and RSUs ahead of time.
About Kevin Caldwell:
With over a decade in the financial services industry, Kevin provides knowledgeable guidance in comprehensive financial planning services to assist our clients. He focuses on behavioral investment consulting, aiming to help clients make sound investment decisions while embracing emotions, but not succumbing to them at the detriment of their long-term financial well-being. Warm and genuine, Kevin enjoys distilling complex information into actionable advice to help the families and individuals we serve thoughtfully pursue their goals.
Before forming Golden Road Advisors, a registered investment advisor practice, Kevin was a financial advisor with Raymond James. Prior to that, he was a financial advisor with Morgan Keegan and a financial services specialist at AmSouth Bank. He earned a bachelor’s degree in finance from the University of Florida.
Kevin is an active member of his community and has been a member of the advisory board for The First Tee of Tampa Bay since 2011 and a committee member of the Tampa Bay History Center since 2013. He is also a board member of the Gasparilla Music Foundation, a charity he has been heavily involved in since 2012, and was previously the lead concierge for Safety Harbor SongFest. As a member of the Coppermugs, he is a community ambassador for the Valspar Championship at Innisbrook. Kevin is a member of the Propeller Club Port of Tampa and the Florida Gators Golf Boosters. He is also an alumnus of the Tampa Connection class of 2014 – members of which must be in or near middle management and destined for leadership in their community and company.
Originally from Clermont, Florida, and a sixth generation Floridian, Kevin lives in South Tampa with his wife, Stephanie, and their kids, Cole and Charlotte.