Episode 457: The Pickleball Playbook for Business Success with Lindsey Busfield

Lindsey Bustfield 00:00
The structure changes depending on where you’re at in developing your pickleball game. It’s a really great way to have that foundation, and it helps you focus. That’s one of the fun things about pickleball: you have structure that builds focus, so you can get into the zone, relax, put everything else aside, and just do what you’re doing.

Intro 00:21
Welcome to the Making Sales Social podcast, featuring the top voices in sales, marketing, and business. Join Brynne Tillman and me, Bob Woods, as we bring you the best tips and strategies our guests are teaching their clients—so you can leverage them for your own virtual and social selling. Enjoy the show.

Bob Woods 00:47
Lindsey Bustfield, thanks for joining me today. Really appreciate your time.

Lindsey Bustfield
Excited to be here. Thanks, Bob.

Bob Woods
You’re very welcome. So Lindsey has one of those stories that immediately grabs your attention. She’s the Vice President of Optimize My Firm, a legal SEO and content marketing agency that’s disrupting the way law firms market themselves.

She comes from a deeply entrepreneurial family, and after a career path that’s taken her from teaching to—yes—egg farming, to now building some of the nation’s most powerful law firm websites, she’s learned a ton about what it takes to thrive as an entrepreneur.

But here’s where it really gets fun: Lindsey is also an avid pickleball player. And if you’ve been following me on LinkedIn or Substack, you know I’ve developed… let’s call it a pretty serious pickleball addiction myself.

Today, we’re going to explore how lessons from the pickleball court connect directly to business, entrepreneurship, and even sales. I’m truly psyched for this conversation. Lindsey, welcome to the Social Sales Link virtual studios and the Making Sales Social podcast.

Lindsey Bustfield 02:00
Thank you so much for having me. I’ve been looking forward to this all week—thinking about pickleball, which I already do—but now I get to have a little bit of structure to it.

Bob Woods 02:09
Yeah. One of the things I like about pickleball—believe it or not, for people who don’t know—is that it really does teach structure. People on the outside looking in, or beginners, often don’t realize how much structure is involved.

Lindsey Bustfield 02:36
Right. That structure can look like so many different things, and it changes depending on where you are in your development. It helps you focus, and it’s one of the fun things about pickleball—having that structure helps you get into a zone, relax, put everything else away, and just play.

Bob Woods 03:02
Absolutely. As much as it pains me to do so, we’re going to save the pickleball talk for a little later because there are other things I want to discuss. Yes, there are other things in life—who knew, right? I wouldn’t have guessed it either, especially lately.

We’ve got you on a path that goes from the farm to eventually the pickleball court. Let’s start at the beginning—with your family. Tell me about your family and how it was entrepreneurial.

Lindsey Bustfield 03:36
Oh wow. So, growing up, I was born into a family of serial entrepreneurs. They were starting businesses before I was born. My parents had a unique skill: they could look at a market, identify a need, and then build a business around it.

They would often build out the business model in their heads just to see if it was viable. We’d be driving down the road, and they’d spot a gap in the market or see a retail space for lease and say, “This would be perfect for this idea. The demographic is over here, people could walk from the pizza shop to the arcade—boom, great hangout for teenagers.”

That’s just how their minds worked. It was their shared hobby. I grew up surrounded by those conversations, and those conversations often became real businesses.

When I was a baby, my parents had an arcade in a great location with lots of foot traffic. After selling it, they started the first large-print phone book for seniors—called The Senior Pages—because this was before Google, and seniors struggled with tiny print. They saw the need, built the solution, and the idea took off.

Then they started Teen Scene Magazine, literally cutting out pictures and pairing them with articles to create the first issue. And all of this was happening while my mom worked as a hospital administrator and my dad was a CEO of a psychiatric hospital.

They built these businesses on the side for fun. Once they grew them enough, they’d sell them—or, if the idea flopped, they’d shut it down. As entrepreneurs, they knew they’d win some and lose some. There’s definitely a pickleball lesson in that.

Their careers shifted constantly. My dad got his pilot’s license, so my mom opened an aviation supply store, and my dad opened the first day-trading facility. His company invented software that let people trade from a computer anywhere, instead of going to Wall Street.

My mom opened a donut shop next door to sell donuts to the day traders and nearby offices. That’s just how they were.

Then my dad went to seminary—yes, really—and earned his PhD in Old Testament and Near Eastern Studies. They moved to upstate New York, where he taught at Hartwick College, and my mom handled international payroll training.

While doing those day jobs, they opened a bed and breakfast on their farm. It became popular—featured on Good Morning America—and drew New York City socialites and Hollywood celebrities.

They had chickens, pigs, cows—your classic farm animals. The eggs from their free-range chickens tasted amazing. They realized the market potential, partnered with an Amish farm, and started selling eggs to a local grocery store.

That grew regionally, and eventually they created one of the nation’s first pasture-raised egg companies. They scaled it tremendously and later sold it.

Now, my mom works in international disaster relief, and my dad sails around the world with Viking Cruise Lines as a resident historian.

That’s the entrepreneurial family I grew up in, and all of that shaped the way I think about business, careers, and society.

Bob Woods 09:33
That is such a wild and wonderful path for a family. I love the synergy between your parents—how they’d create adjacent businesses, support each other, and still maintain their own careers. The creativity and collaboration are amazing. Truly impressive.

Lindsey Bustfield 10:08
They were a great partnership—another pickleball lesson. They played off each other’s strengths, especially with the egg company.

They entered a saturated market—when you go to the egg aisle today, you see tons of options. But they knew their product belonged there, just like many entrepreneurs listening feel about their own creations.

My mom was a brilliant salesperson. She believed in the product and could tell its story passionately. She could convince grocery buyers they needed it on their shelves.

My dad handled the operations—finding new Amish farms to partner with, scaling production, navigating the long lead times of raising chickens.

They motivated each other. If my dad produced a surplus of eggs, my mom needed to sell them. If she closed a big deal, he had to scale up quickly. They were a powerful, creative, strategic team that drove the business forward.

Bob Woods 11:58
So you grew up in this extraordinarily entrepreneurial family. Did you always know you’d end up running something on your own? Did you think it was in the cards, or did it surprise you? Were you inspired by them, or did you ever think, “Nope, I just want a 9-to-5”?

Lindsey Bustfield 12:27
That’s really tough. I think I need to give you a real, honest answer on that — where I didn’t know what to do because I was not a business owner at heart. When I was a kid, I did love the lemonade stands and the garage sales. There was even a time when I gathered a bunch of rocks, put them in paper bags, and sold them to neighbors as they were driving down the road because I ran out of lemonade. I thought, “Here, buy something from me,” and they did. It was cute and adorable — how could you say no? So the ability was there; I had fun with it.

But when it came time to figure out what I was going to do when I grew up, I was stagnant. I went to college and got my degree in philosophy. And when you have a philosophy degree, there aren’t many immediate options that come to mind. You can either be a lawyer or work at Starbucks. I had family who were lawyers, so that sounded appealing, but diving into that debt and responsibility, knowing the lifestyle that comes with it, gave me hesitation. So I thought, “Starbucks — I like coffee.”

I went to Starbucks, and again had this panic moment of, “What am I going to do with my life?” I couldn’t see my way out of it. I didn’t have the entrepreneurial bug. I didn’t have the resources to start a business, and it seemed like a huge risk. I also felt a lot of pressure because I had really successful parents who had the Midas touch — every business they started seemed successful.

I went through a few different iterations in my career. From Starbucks, I got my teaching license, became a high school English teacher, then helped the family grow the egg business doing agricultural compliance and project management. But I found myself traveling all the time, and I wanted to start a family, so I again had to figure out, “What the heck am I going to do with my life?”

Fortunately, I took a temp position at a law firm helping their marketing department update their websites. I said yes to the opportunity to learn something new — because what else did I have going on? I figured out that I enjoyed marketing, got involved with their SEO initiative, and discovered that I loved SEO. Everything started to click.

At the same time, I did aptitude testing at a place called Johnson O’Connor. It’s a two-day test that evaluates your natural abilities and tells you what careers you’d be great at, which ones you wouldn’t, and what drives you. My mom took the test with me. Hers came out showing she was a natural salesperson and project manager. Mine didn’t. My aptitudes were for project management, organization, and being a subject matter expert.

It was liberating, because it explained all my hesitation about being an entrepreneur — it’s simply not natural for me. So I leaned into my aptitudes and found a business partner who had already started the business we’re in now. He took on the risk and the entrepreneurial tasks I hated. He became a great partner, and I found my natural fit there.

Bob Woods 16:56
Yeah, so this is going to get into another question I had about creative pairs. It sounds like this is the real-life example of that and what it looks like in practice for you.

Lindsey Bustfield 17:15
It is. I think so much of success in business is finding your creative pair because none of us has all the skills. If you look at my parents, my mom is the extrovert. She can pick up the phone — which few people do today — and call people to say, “Hey, I’ve got a really great product.” She has no embarrassment factor, which embarrassed me as a teenager, but she got things done.

My dad is the organized one. He put systems and processes in place and built relationships with people on the ground. That was their creative pair. They understood their strengths and weaknesses and supported each other.

Len and I function the same way. He has an innate ability to understand the complexities and technical aspects of SEO. When he was 16, he built internet for his rural town in Pennsylvania. He’s that tech guy, but he’s also approachable — an outdoorsy guy who loves fishing, camping, and his dog. He’s super sweet, but he will be the first to tell you he’s scatterbrained.

We lean on each other. I’m organized, a project manager at heart, and I understand SEO and how it applies to law firms. I can build strategy based on goals and objectives. I put the pieces together based on his big creative ideas.

When you lean into each other’s strengths and compensate for each other’s weaknesses, you can create something very successful. So yes, I wholeheartedly believe in the creative pair.

Bob Woods 19:09
Let’s use that as a springboard to talk about what we’re both dying to talk about. And I’m noticing your earrings right now too — very nice! If you’re listening on audio only, she has a pair of pickleball earrings that are very cute.

Lindsey Bustfield 19:29
You get all these gifts as you get more into pickleball because it becomes your identity. For Christmas you get a lot of pickleball swag. I have too much shame to wear these out in public, but I thought this would be the perfect opportunity.

Bob Woods 19:46
Your debut of the pickleball swag — I love that. So, pickleball. I want to talk about creative pairs as it relates to pickleball. You can play singles or doubles, but unlike tennis — correct me if I’m wrong — most people gravitate toward doubles. Especially if you’re an older guy like me who doesn’t want to chase a ball around all day.

That’s when communication and knowing what your partner can or can’t do becomes important. I think your creative pairs philosophy fits perfectly into that.

Lindsey Bustfield 20:53
I agree. From my personal pickleball experience, there are a few courts I play at, and groups of people who show up consistently. On Tuesday nights, I know exactly who’ll be there. There are partners you enjoy playing with, and over time you learn each other’s strengths and weaknesses.

One beautiful thing about pickleball is the diversity of who shows up. On Tuesdays, I might have a few high school kids still learning the game. They’re new, but they have knees — they can work the court. Then there are older guys from my neighborhood. One had double knee surgery. He has finesse and great control, but he’s not covering the court as much. So when you’re playing with him, you know you have to be the mobile one.

So yes, knowing your partner, their strengths and weaknesses, and being ready to compensate is a huge part of the game.

Bob Woods 22:12
Yeah, yeah. So how did you first get into pickleball?

Lindsey Bustfield 22:17
I got into pickleball about seven years ago. That’s a while.

For those not familiar, pickleball really picked up popularity in the past five years. Anyone playing longer is considered an OG. I’m not quite OG — that’s reserved for the 10-year players — but close.

I got into it because there’s a pickleball court in the park behind my neighborhood. One day I was walking around and saw a group playing. It looked fun. I have a tennis background, so it felt familiar. I asked someone how to get involved — was it a meetup? He said, “Nope, we just show up and play.”

I asked how to learn. He said, “You just show up and play.”

One great thing about pickleball is that no one has been playing so long that they’re snobby about it. A few are, but most remember what it’s like to be new. We weren’t kids when we started, so everyone had to learn. Newbies are welcomed; people will play with you because they know it hurts your feelings if they don’t.

So I was that newbie. I elbowed my way in, irritated a few people because I kept hitting the ball high and getting smacked — but that’s part of the game.

Where I live in Cary, North Carolina, there are pickleball courts everywhere — throw a rock and you’ll hit three. It’s easy to get into here.

Bob Woods 24:24
Yeah. Proximity definitely plays a role. Here in Lexington, Kentucky, pickleball is starting to explode. We don’t have courts everywhere, but where we do, there are a lot. A new park, Shiloh Doe Park, opened with 20 outdoor courts. We now have three indoor facilities.

People are excited — either playing, learning, or thinking about it. So even though it’s been around seven to ten years, it’s really starting to pick up. Your parents will probably try to start a pickleball-related business too.

Lindsey Bustfield 25:37
They’ve always had ideas. I got them to play pickleball too. I’ve seen my dad run the numbers on indoor pickleball facilities to see if they’re worth getting into. I wouldn’t doubt it.

My parents divorced a couple years ago, and now they each have side projects. It gets a little competitive between them. One will have a business idea and ask me to talk it through, and the other will have something similar. I’m like, “Oh no, I can’t talk to you about this because Mom might have something similar going on.”

Pickleball even got caught in the middle once.

Bob Woods 26:27
Wow. So let’s pivot into pickleball and business. I’ve written two Substack pieces about this. There are so many parallels between the two. And it sounds like you’re exploring the philosophy of pickleball and business in a book you’re developing, right?

Lindsey Bustfield 27:10
Yes. The book I’m working on marries philosophy and pickleball. It explores the philosophy of life and pickleball — what you can extrapolate from the game and apply to life.

There’s so much you can learn about the world just by focusing on the principles of pickleball:
• Relationships with your partner — on and off the court
• Purpose — are you playing for fun or competition?
• Skills and how you handle yourself
• The “role play” of the game and how it applies to life

There’s a lot that can be unpacked and applied in a unique and positive way.

Bob Woods 28:28
Yeah, absolutely. Especially around the rules. You see YouTube and IG videos and think, “There’s so much going on.”

The rules can bend. You learn strange things, like the Nasty Nelson — am I saying that right? Where you serve and intentionally hit the non-receiving opponent. It’s legal, but unethical, and people frown on it.

I’m not saying people should do a Nasty Nelson in business, but it teaches you that rules can bend. You should stay authentic, but rules can be flexible.

Lindsey Bustfield 29:42
They can, and that’s true. Not everything you do on the court is “nice,” because the purpose of the game isn’t always to be nice. It depends on why you’re playing — camaraderie or competition?

If you’re playing to win, you will play to your opponent’s disadvantage. You’ll put the ball where they can’t get it. You might do a Nasty Nelson. You’ll target the weaker player. You’ll do things that aren’t inherently nice because that’s the strategy. You suspend ethics a bit to meet your objective.

Entrepreneurship is similar. You have competitors. Few people have a true monopoly. In the marketplace, you play to your opponent’s weaknesses. You hit where they aren’t. You sell where they’re not. You develop products where they’re not. Sometimes you hit them where it hurts. You must understand their weaknesses to put them at a disadvantage.

Bob Woods 31:21
Yeah, and I think that defense against those types of things is something to be thought about as well. I mean, you can’t really do anything about a nasty Nelson, and for some reason, I’m saying that—is that the right phrase? People who know the right phrase will probably comment later, and I will concede that point. But there are ways to combat that from the defensive end as well.

Lindsey Bustfield 31:56
There are, and it goes to the point that you have to pay attention. Just because you assume the other server is going to serve cross-court, if you see that ball coming, you have to get out of the way. It’s about having heightened awareness of everything happening in the space and almost expecting the unexpected. As an entrepreneur, you have to do the same—you expect your opponent to do what they normally do, but you need to keep your guard up just in case somebody throws you a curveball.

Bob Woods 32:33
Right. And every time we say “entrepreneur,” if you’re in sales, mentally substitute “sales” too. Sales is like running your own business within a company. You’re still an entrepreneur, regardless of company size. Everything we’re talking about applies to anyone running any size business.

In pickleball, sometimes the right move is to smash that little neon-colored ball, and sometimes it’s better to just dink it over the net. I want to smash the ball, but half an hour before I hit record, I got a newsletter from Fit Pickler titled “Seven Situations Where Speed Hurts Your Game.” The subtitle was “Sometimes Going Slower is the Fastest Way to Win,” which unintentionally applies to prospecting: slow down your reach to speed up the outcome. How do you think this translates to decision-making and entrepreneurship?

Lindsey Bustfield 34:20
I agree. I struggle with this because I enjoy slamming the ball on the court and making impulse decisions, thinking, “This will be the best thing for the company; let’s throw money at it.” Sometimes it works, sometimes it doesn’t. It helps to slow down. I’m the fast hitter in my creative pair, and my partner Len is the one who says, “Let’s hang back, think through this, and review the numbers before moving forward.” Having a creative pair helps you slow down and think about more angles than you would alone.

Bob Woods 35:25
Absolutely. In pickleball, there are “resets,” where you intentionally slow things down. It brings everyone back, pauses momentum, and prevents you from missing potential opportunities or pitfalls. Slowing down is a good thing.

Lindsey Bustfield 36:06
It is. Sometimes the slow shot is the killer shot. If the other team is on defense and expecting a fast ball, a soft dink over the net can catch them off guard. Executing it well requires self-awareness, both mentally and physically, because you have to release tension and slow your swing. Done correctly, it can win the point.

Bob Woods 37:38
Yes, and in business, that feels just as satisfying. You slow down at the right moment, and it works. In sales, slowing down can be the best move.

Lindsey Bustfield 38:15
With a soft dink, you have more margin for error. You don’t have to hit it perfectly; it’s less risky. Muscle memory from practice ensures consistency, which is why warm-up and preparation are so important.

Bob Woods 39:09
Exactly. Warming up in business, sales, or pickleball is training. You can’t go in completely cold.

Lindsey Bustfield 39:34
A warm lead is infinitely better than a cold call. It’s better to start the engine before diving into the big action.

Bob Woods 39:59
Yes, and you know which shots to go after. In pickleball, you conserve energy by skipping impossible shots. In business, you choose what to chase and what to let go.

Lindsey Bustfield 41:04
We’re intentional about this in our business. We focus on law firms for SEO, narrowing the balls we chase. We avoid wasting energy on clients that aren’t a fit. Choosing the right clients ensures better ROI and long-term partnerships.

Bob Woods 42:32
That makes sense. In business, sometimes deals have just enough uncertainty that you decide to let them go.

Lindsey Bustfield 43:01
Chasing the wrong clients wastes time and resources, and can damage your reputation. Just as in pickleball, you don’t want to injure yourself chasing the wrong ball.

Bob Woods 44:04
Exactly. Once your reputation is hurt, it’s harder to recover.

Lindsey Bustfield 44:15
Yes. Bad decisions compound over time.

Bob Woods 44:33
You don’t do contracts at your company, right?

Lindsey Bustfield 44:44
Correct. We focus on the right clients. If it doesn’t work, they can walk away anytime. This approach contrasts with most SEO agencies that lock clients into long contracts, often overpromising and underdelivering. Our model is client-first and results-driven.

Bob Woods 46:53
Everything you’re saying parallels pickleball. Sports and business intersect beautifully.

Lindsey Bustfield 47:50
Exactly. We could use other sports metaphors, but pickleball works well.

Bob Woods 47:59
It’s time for pickleball to shine. You said, “Pickleball meets you where you are,” and so does entrepreneurship. Can you expand on that?

Lindsey Bustfield 48:33
Pickleball is accessible to anyone, regardless of age or athletic background. You find your partner, your community, and it meets you where you are. The same applies in sales and business: meet your clients where they are and adapt your strategy to their needs.

Bob Woods 50:26
Yes, even with partners or opponents. Flexibility is key.

Lindsey Bustfield 50:45
Pickleball allows for adaptability. You can play any time and meet people where they are, unlike more structured sports.

Bob Woods 51:49
You could even network through pickleball. It’s approachable, unlike racquetball, which is faster, more dangerous, and less accessible.

Lindsey Bustfield 53:08
Pickleball is friendly and fun—it’s impossible to take too seriously.

Bob Woods 53:30
Pickleball and entrepreneurship can be humbling. How do you handle losses or setbacks?

Lindsey Bustfield 54:20
I practice letting go. Forget scores and missed shots. In sales and business, learn from losses, build muscle memory, and move on. Don’t let failures eat your confidence.

Bob Woods 56:09
Reframing losses as learning opportunities is critical. I learned this early in my career transitioning from journalism to business.

Lindsey Bustfield 57:49
Exactly. Identify what needs practice and let go of individual failures.

Bob Woods 58:11
We could talk for hours, but let’s wrap up. If an entrepreneur or salesperson could take one lesson from pickleball to apply in business, what would it be?

Lindsey Bustfield 1:00:10
Build relationships first. Don’t focus on the sale. Foster connections, and sales will follow naturally.

Bob Woods 1:00:23
Perfect. Where can people get in touch with you?

Lindsey Bustfield 1:00:10
Our website is optimizemmyfirm.com. You can email me at lindsay@optimizemyfirm.com, and I’m on LinkedIn as Lindsay Busfield.

Bob Woods 1:00:23
You’re also a podcaster, right?

Lindsey Bustfield 1:00:27
Yes, I host The Personal Injury Marketing Minute, covering hot topics in legal marketing.

Bob Woods 1:00:55
You’re also working on a second book?

Lindsey Bustfield 1:01:24
Yes. It’s about navigating a career and entrepreneurship while living under the shadow of highly successful parents. The book is called WTF to Do with a Philosophy Degree.

Bob Woods 1:02:17
That’s much needed.

Lindsey Bustfield 1:02:39
Thank you. I hope to inspire people with similar backgrounds.

Bob Woods 1:02:58
Fascinating. Thank you for joining me.

Lindsey Bustfield 1:03:13
Thank you for having me.

Outro 1:03:17
Thank you for streaming this episode of Making Sales Social. Remember, make your sales social every week. Join us for more guest instructors bringing marketing, sales training, and social selling strategies. Subscribe to get the latest episodes on  Apple Podcasts, Spotify, Youtube Music, and Amazon Music. Visit our website, socialsaleslink.com, for more information.