06/02/2026
After nearly 30 years as a financial advisor, one of the most common questions I've heard is: "Jeff, when can I afford to retire?"
In my latest article, I explore what really determines retirement readiness.
Read more: https://ow.ly/W9R150Z6Ny5
- ๐๐ฆ๐ง๐ง ๐๐ณ๐ฆ๐ฆ๐ฏ, ๐๐ช๐ฏ๐ข๐ฏ๐ค๐ช๐ข๐ญ ๐๐ฅ๐ท๐ช๐ด๐ฐ๐ณ & ๐๐๐ ๐ฐ๐ง ๐๐ช๐ฏ๐ด๐ต๐ฐ๐ฏ๐ฆ ๐๐ฆ๐ข๐ญ๐ต๐ฉ ๐๐ข๐ณ๐ต๐ฏ๐ฆ๐ณ๐ด
05/27/2026
In my most recent article, โFrom First Job To Real Wealth: What Actually Matters Early On,โ I walk through a few things that matter more than people realize when starting their careers.
Compensation, habits, and how you handle early opportunities can shape the path ahead more than most expect.
With graduation season upon us, I hope this is helpful.
Read more here: https://ow.ly/wxTN50Z19Ig
- ๐๐ฆ๐ง๐ง ๐๐ณ๐ฆ๐ฆ๐ฏ, ๐๐ช๐ฏ๐ข๐ฏ๐ค๐ช๐ข๐ญ ๐๐ฅ๐ท๐ช๐ด๐ฐ๐ณ & ๐๐๐ ๐ฐ๐ง ๐๐ช๐ฏ๐ด๐ต๐ฐ๐ฏ๐ฆ ๐๐ฆ๐ข๐ญ๐ต๐ฉ ๐๐ข๐ณ๐ต๐ฏ๐ฆ๐ณ๐ด
05/26/2026
We operate as a team here, so when you work with Winstone, you have multiple people working together behind the scenes on your account.
That means more perspective. More coordination. More support.
All of which is incredibly intentional.
But even though we show up as one cohesive team, each person plays a specific role in making sure our clients are taken care of the right way.
We thought it might be helpful to share a bit more about what that actually looks like and how each role contributes to a very cohesive team.
So we asked our team one simple question: โHow would you describe your role in one sentence?โ
Hereโs what Lauren Smith, our COO and a Financial Advisor, had to say:
โI make sure what we promise clients gets delivered, bringing together planning, service, and operations so everything works the way it should.โ
05/25/2026
As a veteran, Memorial Day has always carried a different weight for me. Itโs easy for this weekend to feel like the start of summer: time with family and friends, hanging out and grilling outside, a break from the normal routine. And I genuinely hope people do get to enjoy that.
But underneath it, Memorial Day is something much more important. And I hope people remember that, too.
Memorial Day honors the brave men and women in our military who made the ultimate sacrifice. Itโs not about all of us who servedโฆ itโs specifically about those who didnโt come home.
Over the years, Iโve found myself thinking more about themโฆ and the families who carry that loss every day. And how Memorial Day is one of the clearest reminders we have of the real cost of our freedom.
So wherever you are today, Iโd encourage you to take a moment to pause and reflect the true meaning of today. Because itโs worth remembering.
- ๐๐ฆ๐ง๐ง ๐๐ณ๐ฆ๐ฆ๐ฏ, ๐๐ช๐ฏ๐ข๐ฏ๐ค๐ช๐ข๐ญ ๐๐ฅ๐ท๐ช๐ด๐ฐ๐ณ & ๐๐๐ ๐ฐ๐ง ๐๐ช๐ฏ๐ด๐ต๐ฐ๐ฏ๐ฆ ๐๐ฆ๐ข๐ญ๐ต๐ฉ ๐๐ข๐ณ๐ต๐ฏ๐ฆ๐ณ๐ด
05/21/2026
This time of year, I always find myself thinking about graduates.
High school seniors heading off to college. College graduates stepping into their first real jobs. For many of them, itโs the first time theyโre truly starting to think about their careers and, whether they realize it or not, their financial lives as adults.
After nearly 30 years of helping families plan for retirement, Iโve had a front-row seat to how financial decisions play out over time. What rends to work. What doesnโt. And where things can get off track.
So, for those early in their careers, whether thatโs your child, your grandchild, or even yourself, I wanted to share a few things Iโve learned along the way and have even shared with my own sons.
Read my latest article โFrom First Job To Real Wealth: What Actually Matters Early Onโ for more: https://ow.ly/Op0750Z19tO
- ๐๐ฆ๐ง๐ง ๐๐ณ๐ฆ๐ฆ๐ฏ, ๐๐ช๐ฏ๐ข๐ฏ๐ค๐ช๐ข๐ญ ๐๐ฅ๐ท๐ช๐ด๐ฐ๐ณ & ๐๐๐ ๐ฐ๐ง ๐๐ช๐ฏ๐ด๐ต๐ฐ๐ฏ๐ฆ ๐๐ฆ๐ข๐ญ๐ต๐ฉ ๐๐ข๐ณ๐ต๐ฏ๐ฆ๐ณ๐ด
05/20/2026
This month marks Claire Holmesโ 6-year anniversary with Winstone.
As our Director of Marketing and a member of our leadership team, Claire has helped shape not just how we communicate, but how we operate. She brings a thoughtful, intentional approach to everything she does, paired with the ability to turn ideas into something real and meaningful.
Sheโs also someone who consistently shows up for the team: steady, organized, and always thinking a few steps ahead.
Weโre incredibly grateful for her leadership and all that sheโs contributed over the years. Thank you, Claire!
05/19/2026
The wealth management landscape is changing fast. And at Winstone, weโre building something that lasts.
Weโve invested in the right people, processes, and systems to give advisors the tools they need to grow faster and serve clients better.
From marketing and operations to compliance and succession planning, our focus is on taking the business burdens off your plate so you can do what you do best: serve families.
If youโre a financial advisor ready to align with a firm thatโs growing intentionallyโand thinking decades aheadโwe should connect.
Schedule a quick intro call with me: https://ow.ly/gS9c50Z19ph
Learn more about how we partner with advisors: https://ow.ly/mh0750Z19pn
- ๐๐ฆ๐ง๐ง ๐๐ณ๐ฆ๐ฆ๐ฏ, ๐๐ช๐ฏ๐ข๐ฏ๐ค๐ช๐ข๐ญ ๐๐ฅ๐ท๐ช๐ด๐ฐ๐ณ & ๐๐๐ ๐ฐ๐ง ๐๐ช๐ฏ๐ด๐ต๐ฐ๐ฏ๐ฆ ๐๐ฆ๐ข๐ญ๐ต๐ฉ ๐๐ข๐ณ๐ต๐ฏ๐ฆ๐ณ๐ด
05/14/2026
Some of the most important lessons I use today didnโt come from college or even my professional experience.
They came from my time in the military.
Lessons about discipline, decision-making under pressure, and not overreacting when things feel uncertain (which is especially relevant in markets like we see today).
I donโt share these stories often, but in honor of Military Appreciation Month, I pulled together a few that still guide how I show up for clients and our team.
You can read them in my latest article โLessons From My Time In The Military That Still Show Up Today:โ https://ow.ly/wlkC50YZJzK
- ๐๐ฆ๐ง๐ง ๐๐ณ๐ฆ๐ฆ๐ฏ, ๐๐ช๐ฏ๐ข๐ฏ๐ค๐ช๐ข๐ญ ๐๐ฅ๐ท๐ช๐ด๐ฐ๐ณ & ๐๐๐ ๐ฐ๐ง ๐๐ช๐ฏ๐ด๐ต๐ฐ๐ฏ๐ฆ ๐๐ฆ๐ข๐ญ๐ต๐ฉ ๐๐ข๐ณ๐ต๐ฏ๐ฆ๐ณ๐ด
05/14/2026
A lot of financial advisors talk about being โteam-based.โ But for us, itโs how we actually operate.
When you work with Winstone, youโre not just working with one person. Youโre working with a true team of us, all with the goal of supporting you and your financial plan. We operate as one team, with one voice, so thereโs alignment behind the scenes and consistency in every conversation.
But within that, each person plays a distinct role in how we serve our clients, and we wanted to share what that actually looks like.
So we asked our team one simple question: โ๐๐จ๐ฐ ๐ฐ๐จ๐ฎ๐ฅ๐ ๐ฒ๐จ๐ฎ ๐๐๐ฌ๐๐ซ๐ข๐๐ ๐ฒ๐จ๐ฎ๐ซ ๐ซ๐จ๐ฅ๐ ๐ข๐ง ๐จ๐ง๐ ๐ฌ๐๐ง๐ญ๐๐ง๐๐?โ
Hereโs what Dylan Daggett, one of our Financial Advisors, had to say:
โI act as the quarterback for our clients and team, bringing strategy, communication, and ex*****on together to make sure weโre all focused on what matters most and following through on it across their investments and financial plan.โ