Welcome to the reimagined TradeWinds Money Courage, a monthly blend of TradeWinds culture, financial education, and real-world advice delivered to your inbox on the last Wednesday of every month.
We hope you enjoy our first edition.
February: Relationships & Money
February isn’t just about Valentine’s Day, it’s a reminder that the relationships in our lives are deeply connected to how we think about, use, and talk about money.
1. Money as a Relationship Language
- How couples communicate (or avoid communicating) about finances
- The importance of financial transparency vs. autonomy
- Common money conflicts and how to navigate them
2. Different Money Personalities in Relationships
- Spender vs. Saver dynamics
- Risk-taker vs. Security-seeker
- How opposites can complement (or clash)
3. Financial Conversations to Have (at every stage)
- Dating/Early relationship: When to talk about money
- Engaged/Married: Joint accounts, separate, or hybrid?
- Parents: Teaching kids about money through your relationship
- Business partners: The financial foundation of partnerships
4. Practical Framework
- Set regular “money dates” (monthly check-ins)
- Align on shared goals before debating tactics
- Establish boundaries and respect differences
- Create transparency without judgment
The best financial plans aren’t just about numbers, they’re about alignment, trust, and shared vision. And February is the perfect time to strengthen those connections.
🛠️ Helpful Tools to Get You Started
👉 Couples Finance Tool
Honeydue: One of many apps designed to help couples manage money together while maintaining individual autonomy. Track shared expenses, set goals together, and keep communication open.
👉 Conversation Starter Guide
Quick Reflection Questions for Couples/Partners:
- What’s one financial goal we both want to achieve this year?
- Where do we disagree most about money—and why?
- What does financial security mean to each of us?
- How do we want to model money habits for our kids (if applicable)?
- What’s one thing we could do differently to feel more aligned?
Added note: Check out Carl Richards Podcast 50 Fires. A Podcast About Money and Meaning, Carl has frank, funny, and often difficult conversations about money—the kind we were all told not to have!—with guests from all walks of life.
From the Studio
Beyond the Balance goes deeper than dollars and cents, exploring how our financial choices shape our lives, relationships, and happiness. Each episode features real conversations with guests from all walks of life: advisors, entrepreneurs, parents, and everyday people who talk about what balance really means in money and in life.
Newest Episodes:
Episode 3 with Matthew Snider: Matthew shares his journey into Bitcoin and Web3, explains why understanding blockchain technology matters beyond the headlines, and breaks down how digital assets fit into a broader financial ecosystem.
Episode 4 with Shannon Thomas: Shannon shares her journey from international finance and Wall Street to IT tech sales at Red Hat and Pure Storage—all while launching a family-owned deli rooted in community, tradition, and great food.
Pocket-Sized Advice is a short-form video series delivering clear, practical financial guidance, one bite-sized idea at a time. Each episode breaks down real-world money topics into simple, actionable insights you can actually use.
Newest Videos:
Pocket-sized Advice: Understanding Your Money Persona for Better Financial Decisions
Jeb Bowie introduces the concept of “money personality” on Pocket Size Advice, describing four common money personas: the saver, spender, avoider, and controller.
He explains that none of these tendencies are inherently wrong, but issues arise when people don’t recognize their patterns and allow one persona to drive every financial decision.
Inside TradeWinds
Welcome Emma Schneider!
We’re excited to welcome Emma to TradeWinds as our new Client Associate. A former high school math teacher and North Carolina State University graduate, Emma brings an educator’s heart and a gift for making complex financial concepts feel clear and approachable.
She previously worked in wealth management at Morgan Stanley, partnering with advisors and clients to deliver a thoughtful, personalized service experience. We’re grateful to have her dedication and care supporting our clients.
Welcome to the crew, Emma!
Tim at the Daytona 500
Our very own Tim Whitney recently joined Robinhood at the Daytona 500!
Tim and his son Ben had the opportunity to check out pit row, where they met Michael Jordan, a once-in-a-lifetime experience!
Nothing says February like high-speed racing and financial services. 🏁
TradeWinds Recommends
Jeb
Jeb is a big fan of Neuse River Brewing Company for dinner and highly recommends their rotating homemade pasta on Wednesdays and rotating burger specials on Thursdays. He also swears by the duck poutine and the roast chicken, both are hard to beat.
Tim
Tim has recently taken up boxing, a new hobby he enjoys sharing with his kids. It’s a great blend of discipline, focus, and endurance… watch out, Mike Tyson!
Ralston
Ralston is a big fan of iSmash when he needs to let off some steam and have a little fun. There’s something oddly satisfying about smashing a few plates or electronics and walking out feeling lighter than when he walked in.
Todd
Todd has restrung his guitar and is getting back to chasing his dream of becoming a rockstar one day. 🎸
Question of the Month
What does it mean to file an extension on my taxes?
“Filing an extension buys 6 more months to collect information as you prepare your tax return. The IRS requires Form 4868 as the formal way to request this extension; the major tax preparation softwares (like TurboTax) can help you file this. Please note: an extension doesn’t give you more time to pay your taxes; the IRS still wants you to pay the most reasonable amount of taxes by the Tax Filing Deadline in April. It is almost always better to file even if you don’t have the money to actually pay the tax. The penalties are much steeper for those who ‘Fail to File’ versus those who ‘Fail to Pay.'”
What’s Next?
The Calm Before March Madness… and Tax Season
February may be the month of love, but March brings a different kind of intensity: March Madness (brackets, buzzer-beaters, and Cinderella stories) and the final push toward the April 15 tax deadline.
Tax Season Reminders:
- Final tax documents should arrive by mid-February
- Schedule your tax prep appointment if you haven’t already
- Have questions? Reach out, we’re here to help you stay ahead of the deadline
Just like a great bracket strategy, smart tax planning requires preparation, flexibility, and knowing when to take calculated risks. We’ll help you navigate both.
Onward with Optimism,
The TradeWinds Team
