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5 Independent Broker Dealer CEOs with the Best Hair

Here are the best hairstyles I see the top independent broker dealer CEOs pulling off, and how they brands they lead have benefited.

Hair matters. In no particular order, here are the best hairstyles I see the top independent broker dealer CEOs pulling off, and how the brands they lead have benefited.

By the way, thanks for joining me.

For those of you who are new to my blog/podcast, my name is Sara. I am a CFA® charterholder and I used to be a financial advisor. I have a podcast in which I talk about financial advisor lead generation topics is best described as “fun and irreverent.” So please subscribe!

Sara Grillo, CFA is a highly fun and slightly crazy marketing consultant based in NYC.
I am an irreverent and fun marketing consultant for financial advisors.

So if you’re looking for some straight up talk then you’ve come to the right place!

#1 Dan Arnold of LPL

Why he made the 2019 “Best Broker Dealer CEO Hair” list

I love how Dan Arnold has hair that moves.


It’s such a departure from the stiff hair that you usually see in people in this role. This look his bio picture is soft and free flowing, nicely complimenting his oval facial shape.

What it does for the firm’s brand

His hair makes him relatable.

In this clip of Dan talking about LPL’s culture change, look at how alive he is. He’s not going for superiority here. Sporting the “no tie” look well, his understated dress and dynamic, engaging body language convey the point he’s trying to make – that LPL wants to connect with clients on a human level.

Nicely done.

Style tips if you wear this look

When you go with a longer hair style, you’ve got to constantly keep up with it. This can cross over to shaggy or windblown motif if not maintained.

Set that recurring meeting up with the barber for every 2-3 weeks otherwise you may wind up looking like you drove to work on your motorcycle.

Paul Reilly of Raymond James

Why he made the 2019 “Best Broker Dealer CEO Hair” list

I have to give it to Paul Reilly for having the highest ratio of total hair per square inch than any other broker dealer CEO I have seen. He makes every strand of it work, though!

What it does for the firm’s brand

Just like RJ’s ability to be a publicly traded company yet avoid the bulge bracket-ish feeling that people run from, Paul’s hair and mustache combo has it all together. Neat and organized with a touch of character, Paul and his firm have style.

Style tips if you wear this look

Be aware that when you have a high volume of hair included in your look, you may have to tone down other aspects of your style to avoid being too busy. Paul does this well; for example in this clip of him speaking, he’s gone with glasses with no bottom rim. Nicely balanced.

Downplay the accessories, in other words. Beard or mustache are bringing enough character to the picture.

Penny Pennington of Edward Jones

Why she made the 2019 “Best Broker Dealer CEO Hair” list

I love what Penny Pennington’s hair does for her delicate facial features. Her wispy bangs add softness and are just the right length while accentuating her eyes to convey an expression of confidence. The whole look just works.

What it does for the firm’s brand

I love how Penny is able to represent her brand as its Managing Partner powerfully as a female leader and look so stylish at the same time. Diversity and inclusion are important for a financial brand in this modern age and are an inspiration.

Style tips if you wear this look

Anytime you are using a highly styled look involving product such as gel you want to make sure not to apply too much and making it obvious. This is especially important for shorter styles.

Philip J. Sanders of Waddell & Reed

Why he made the 2019 “Best Broker Dealer CEO Hair” list

Philip Sanders makes the best hair list because of his clean cut and versatile hairstyle. As shown on his bio page, he can wear it with a side part or slightly elevated and brushed straight back for more volume.

What it does for the firm’s brand

A conservative look for a traditional kind of firm.

Style tips if you wear this look

This is the Toyota of hairstyles. It’s durable and you can get a lot of mileage out of it. However it’s not the most dynamic style.

Consider adding short sideburns if you want to give it some vavoom!

Dennis R. Glass of Lincoln Financial

Why he made the 2019 “Best Broker Dealer CEO Hair” list

First of all, what a great bio picture. Dennis looks sincerely happy and his overall vibe is warm and inviting.

The long on top style works out okay here. He’s probably applied product, but it seems like the right amount. The hair falls nicely but doesn’t seem overly floppy.

What it does for the firm’s brand

This style reminds me of Leonardo DiCaprio in the 1990’s. This is cool, youthful style goes well with a brand that has over the years shifted its focus to be on empowering families rather than being the typical insurance broker.

Style tips if you wear this look

Long on top styles have to be carefully monitored to avoid poofing on the sides. If the sides get too long and start to extend past ear level, you risk losing the overall shape and having the whole thing balloon into a mushroom.

Sara’s Upshot

If you found this blog helpful, please subscribe to my podcast below which goes into the subject of financial advisor LinkedIn messages and sequences in fuller detail.

Or, you could download my e-book.

I wrote an e-book called, “47 Financial Advisor LinkedIn Messages and Sequences that will NOT make you look Stupid. “ If you are a financial advisor trying to meet new clients over LinkedIn or other social media sites and you need some scripts, you can download it here.

I wrote this e-book for financial advisors who want to be perceived as high quality people on social media. The e-book contains 47 messages you can use on LinkedIn or Facebook messenger to reach prospects, COIs, and other useful connections that would benefit your practice.

I also have a membership program, helping people to be able to develop business with these more sophisticated clients. This program talks about content creating (blogs, podcasts, newsletters, etc) as well as financial advisor strategies for using LinkedIn, Facebook, and Twitter for getting new leads. I also talk about how to relate your marketing and lead generation to certain financial advisor practice management topics. For example, the profitability worksheet I discussed in this blog is a tool that I provide to everyone on my membership.

Thanks for reading and please stay with me for the next one.


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Redesigning the Briefcase Bag

If I were to design a briefcase bag, here’s what it would look like.

For years I’ve been searching for a briefcase bag that is professional yet stylish at the same time – and I’m constantly frustrated. If I were to design a briefcase bag, here’s what it would look like.

Why the current options stink

I find it unfulfilling every time I have to buy a briefcase bag. I feel as if I have to sacrifice either style or functionality and can never achieve them both.

It is at the point where I seriously have considered starting my own bag line. I just can’t not seem to find a bag that looks stylish while at the same time does what I need it to do for me namely:

  • Carries my shoes. This is my #1 struggle in business commuting. I’ve come to the sad conclusion that it may not actually be possible to carry your high heels in the same bag as your business items. They always crush or soil the bag’s contents.
  • Has a “quick grab” place for my phone, keys, and subway card where these items can’t slosh around and get lost.
  • Contains a glasses compartment where my spectacles won’t get scratched or broken.
  • Has a place to put my touch up cosmetics such as lipstick etc. Things leak no matter how well sealed so this would have to be waterproof.
  • Stores my laptop
  • Stores my business papers without them getting crinkled or torn
  • Has a pen holder. Have you ever gone to get a deal signed and can’t find your pen? Ruins the whole close.

Every bag I find is either too heavy or too bulky and makes me feel like I’m getting ready to fly Delta out of LaGuardia. I am about to throw it all in my kid’s Disney Princess backpack and call it a day.

How’s that for de haute couture?

In store results – unfulfilling

I recently took to the stores. But do you know how hard it is to go briefcase bag shopping in Manhattan with kids? The high end places can see the circus coming.

“Ma’am please tell your kids to stop getting their fingerprints on the merchandise.”

To which my response is, “You’re right. Give me three tickets. I’ll pick them up in an hour – where’s your baggage claim?”

So it’s clear I have a limited capacity to shop in store. So I had to go online, but even then, here’s what I found to be the most viable candidates. And even these don’t really do it for me.

Michael Kors Whitney

This is a tote bag but from what I gathered you could probably get away with fitting a laptop into it. The strap length would allow me to carry it without making it too heavy. I like how the zipper is on the top invisible from the outside – too many zippers and I feel like I’m going skiing in the Swiss Alps.

The interior is spacious but there’s no real segmentation to accommodate my list of needs (see above). I envision crumpled papers and things getting crushed as a result.

Retails at $298.00

If you like this style but want a slightly lower price point see the Ralph Lauren Andover Tote.

Longchamp Roseau

If you’re willing to pay over $500 for a bag, this would be a good candidate. It’s made of high quality materials and seems like it can take a beating. Although it is roomy enough to fit all that you’d need, there’s only a zipper pocket and no compartmentalization. Crumpling and soiling likely.

Coach Willis Top Handle

This is a solid multi-unction bag. It would work well for business and personal life and it goes for a little less than $500. The flap gives it a little personality. I also noticed several compartments however if you want to take your laptop along this is probably not for you.

Bebe Janet Satchel

Having made ourselves unpopular in the luxury stores I ventured out to T.J. Maxx where I found this beauty on sale. I’m a sucker for quilted bags. Although this isn’t as roomy as the others I think you could maybe squeeze in your laptop. Not sure if you can get this in the stores anymore but I did find some entries for it on Pinterest.

Redesigning the briefcase bag

If I were to design a briefcase bag, here are two ways I would possibly do it.

Model One

One is a stacked model. The bag is lengthy with two layers, one on top of the other. The layer on the bottom is waterproof and carries shoes and makeup while the top layer is for papers and laptop with a “grab compartment” for the quick access items.

You’d be able to access the bottom layer from the side to avoid having to rummage through your top lawyer to get to the bottom layer. You’d have to wear collapsible shoes (such as slipper shoes) while commuting and carry your heels in a separate bag. Once you got to the meeting you change into the heels and store the commuting shoes in the bottom layer of the bag.

Here’s a rudimentary sketch. This is a side view:

Model Two

This one is a one layer bag wider than it is long with document/laptop storage in the middle and compartments on either side. One compartment is for the grab items while the other is waterproof and stores the shoes and makeup.

Here’s a view from the top looking down into the bag:

As for the styling of the bag’s exterior, there would be a see through panel where you can plug in different patterns depending on the meeting such as:

  • Leopard
  • Polka dot
  • Swirls
  • Your company logo and name
  • Geometric shapes

Sara’s Upshot

I would love to hear your thoughts on my designs and on business briefcase bags in general. Please kindly comment here or send me a message.

Authenticity is what matters most in any financial advisor who wants to get new clients. Learn the no BS way to use social media to get new clients by joining my membership here.

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Cash in Those Sock Options

Here are some great sock options that you can consider that won’t make you sacrifice your professionalism or your style.

Does anyone agree with me that pantyhose is perhaps the most uncomfortable piece of clothing on the face of the earth?  Here are some sock options that you can consider that won’t make you sacrifice your professionalism or your style.

Why I threw mine in the pail

I’ve never been a fan of nylons from a financial standpoint. I find it extremely vexing that they go for $8 a pair yet they tear as easily as tissue paper. How do they get away with this rip off? There should be a money back guarantee.

What finally led me to escape was my first pregnancy. I had never before in life stored something the size of a basketball in my stomach.  Oh, the bruised ribcage!

I got one of those pairs of pregnancy nylons (and believe me, those cost a fortune) but by the eight month, I felt like a tube of toothpaste being squeezed with the cap still on. I literally could not breathe.

I finally decided enough was enough, and emerged from the company bathroom leaving the dreaded things in the trash pail. I was stared down passing by the cubicle of a coworker who muttered, “That is so against company policy (eyes rolling)” loudly enough for the people around her to hear.

“So is making pregnant employees feel like a balloon that’s about to burst!” I responded.

It just slipped.

What can I say, I’m too “bad” for Corporate America anyways.

It’s not cool how women are expected to squeeze, cover, clip, dye, or cover up parts of our bodies 100% of the time so we can meet standards. We’re all worthy of feeling beautiful as we are.

What do you think about these options?

Going bare

Admittedly I’ve sported this look before, as the nylon section of my drawer has been vacant for several years. To be honest I’m not the biggest fan of bareleggedness in business. Especially if you are working in a conservative industry like finance, you never know whom you will offend.

You have to be really careful that you are wearing a long enough skirt – at least past knee length. Make sure you test this by sitting down.  The risk here is that any exposure of thigh skin is going to attract unwanted attention and you know what that does to your credibility.

If you go bare, consider that some people may be offended by this, even with the appropriate length of skirt. Consider how formal the company is that you will be keeping. If you aren’t sure, stash a pair of nude tights in your handbag as a safety measure.

Women’s trouser Socks: boring but more comfortable

Consider trouser socks. You’ve probably worn something like these before.

No Nonsense Women’s Flat Knit Crew Sock

Women’s 6 Pack Silky Sheer Knee High trouser socks

I’m still frustrated.

There were some interesting patterns such as polka dots and zig zags. Overall nothing too exciting. Plus, these sheer trouser socks often are lacy. I kind of feel like a doily when I wear lace.

What shoes do you wear with knit trouser socks? Maybe try Oxfords or loafers with a heel. Too masculine? I have some more feminine shoe options to discuss later in this article.

Men’s trouser socks: cash ’em in!

If you share my frustration with the lack of eye-catching women’s trouser socks, I would suggest throwing caution to the wind and purchasing men’s trouser socks.

I found some men’s trouser socks that make a statement. Although these were created for men, to me they don’t appear overly masculine.

Teal up the runway

Look at these beauties. Teal heatmap swirls with some yellow accents throw in there, zig zags. Fun!


Now we’re talking!

Value pack

Just be careful with the striped one; you don’t want to look like Where’s Waldo.

How to wear men’s trouser socks femininely

Now, let’s say you wanted to wear trouser socks with a skirt.


Yes, it can be done although consider your company. If you are going to be around people who have a heart attack over every little thing, this may not be the best look.

Here are some combos to consider:

  • Midi skirt with high heeled stiletto ankle boots. Leave a little sock (about an inch) showing up high and this looks great.
  • A-line skirt with pointy toe pumps. Match the pumps to the skirt and use a patterned sock.
  • Trouser skirt with t-straps or mary jane heels. If you wear a patterned sock, make sure it doesn’t look weird where the shoe cuts the ankle in half. Striped socks may be the best option here.

Sara’s Upshot

Authenticity is what matters most in any financial advisor who wants to get new clients. Learn the no BS way to use social media to get new clients by joining my membership here.