Grow Your Network: Brad Fisher Is The Ultimate Insultant

Here's HOW and WHY to connect with Brad Fisher

For years, I've been connecting with interesting people and documenting insights that might help my clients and myself. What was once private is now (mostly) public.

People often ask: "How do you know all these people?" and "How do you connect these (re: random) ideas?" The answer is simple: consistent relationship cultivation and thoughtful note taking. My north star is trusting my instincts, my maps are the constellations in these reflections.

This approach to multidisciplinary networking has helped dozens of clients, colleagues, and friends strengthen their networks and unlock new opportunities. Feel free to steal these ideas directly - that's what they're for! I can't promise you'll learn FROM me, but I guarantee you can learn something WITH me. Let's go. Count it off: 1-2-3-4!

Introducing... Brad Fisher!

Do you know Brad Fisher? He's Managing Director at Scalable Leadership, a consultant who specializes in structural scalability for mid-size companies and family businesses. But more importantly - and this is where it gets interesting - his own son once described what he does in four words that have stuck with him ever since: "My daddy's an insultant."

If not, allow me to introduce you. Brad works with business owners, CEOs, and leadership teams to help them navigate what he calls the "Second Leap" - that critical transition from stage one to sustainable, scalable growth. His approach blends business engineering with psychology, grounded in the belief that people don't change for strategies; they change when someone actually listens to them and tells them what they need to hear (not what they want to hear).

I wanted to connect with him because he embodies something I value deeply: the willingness to ask hard questions and the patience to sit in the discomfort while someone finds their own answers.

Our conversation is LIVE now on the Just Press Record YouTube channel (and this Cultish Creative Playlist). Listen and you'll hear two people who understand that real transformation happens through listening - but one does it through podcasting and storytelling, and the other does it through business strategy and leadership coaching.

THREE: That's The Magic Number of Lessons

In the meantime, I wanted to pull THREE KEY LESSONS from my time with Brad Fisher to share with you (and drop into my Personal Archive).

Read on and you'll find a quote with a lesson and a reflection you can Take to work with you, Bring home with you, and Leave behind with your legacy.

WORK: Tell Me Your Story (And Then Shut Up And Listen)

"I like to find a miniature version of that and really essentially ask, what's the most important thing for us to talk about today? What's on your mind? And if you get in the habit of doing that, and then just shut up and listen, then the essential bits will come out."

-Brad Fisher, Just Press Record on Cultish Creative YouTube

Key Concept: Brad has cracked a code that most leaders never learn - that progress isn't about having all the answers or imposing your framework on someone else's problem. It's about asking one good question and then genuinely listening for the answer. The "shut up and listen" part is the hard bit. When you let people think, when you resist the urge to fill silence with your expertise, something magical happens: they find their own path. That's not consultancy; that's enablement. In business, this matters because the people closest to the problem usually know the solution - they just need someone to help them see it.

Personal Archive Note-To-Self: Somewhere along the line, the Henry Ford quip that “Any customer can have any color they want - so long as its black” gets into most professional’s heads. They see, and pattern matching reinforces it, a common problem that they figured out how to solve, and make a profit by solving, and then every problem starts to look the same. It’s the man with a hammer thing. Where every problem looks like a nail.

This happens in the world all the time. We’ve all met these people. We’ve all bought insurance from this guy, or narrowly avoided buying it, and reflected on how compelling and confident they made it sound, all while realizing they did all the talking and we did none.

The Henry Ford car color solution is so practical. It makes tons of sense. But it also creates a massive opportunity to do the opposite. What if the person doesn’t even want a car, let alone a black one? What if they really want a bike? Or a wagon? How are you going to find out?! You just have to ask and listen.

For all the impressive people Brad has worked with and helped over his years of professional experience, it’s no mistake he comes back to this principle of listening over and over again now, and that it’s so closely influencing what he wants to do next with his professional life. Brad’s not a man with hammer. He’s a man with a toolbox.

Work question for you: When was the last time you asked someone a question and then gave them the space - real space - to actually think before answering?

LIFE: Island A vs. Island B - Defining What You Really Want

"You're sitting today on island A and it's a beautiful island. And you look across about two and a half, three miles across the bay. There's another island, island B. And that island is even better than island A. You've gotta figure out why and what your island B would be."

-Brad Fisher, Just Press Record on Cultish Creative YouTube

Key Concept: Brad's Island A and Island B metaphor cuts through all the noise of "success" as society defines it. He's seen it a hundred times - the hundred million dollar company, the huge bank account, the all the external markers of success - and the person sitting on top of it is miserable because they never defined their Island B. They're still chasing someone else's dream. Island B forces you to get honest: what do you actually want? Not what looks good. Not what your dad built. Not what society expects. The two and a half miles across the bay is the gap between where you are and where you actually want to be. Most people never even look. This is the work of the Second Leap - not scaling faster, but scaling toward something that actually matters to you.

Personal Archive Note-To-Self: The idea that most people never even look for where they want to be, they just let life happen, makes me a little sad. But then I remember what Brad’s doing. Because life is so busy, work is so hard, that stopping to actually work out where you want to get to and why takes a little outside influence sometimes.

Going back to the Ford and man with hammer metaphors above, successful people get really about doing a certain thing a certain way. It’s totally reasonable to imagine you can take that work ethic and logic, and train it on something new. Maybe it’s retirement. Maybe it’s your marriage. Maybe it’s your relationship with your kids. But - beware the everything looking like a nail. Beware the “everybody gets a car so long as its black” style of living.

Sometimes you need someone to listen to you so you can start to hear yourself. Brad’s got the gift for this. And, he’s got the gift of not trying to force one tool or template onto defining what to do once those stories are on the table.

When Brad talks about the islands, I find myself actually seeing them - the beach, the water between them, the effort it’s going to take to cross. That's the genius of his framework. He's not giving you a template of what to think, he's asking you to draw the map of your own territory. And somehow that makes the leap less terrifying, and more exciting to consider.

Life Question For You: What's your Island B? And more importantly - have you actually looked across the bay to see it?

LEGACY: You Don't Create Stories - You Discern Them

"When you're listening to someone's story, the natural human tendency is to try to connect the dots and create a narrative of your own. When there's another person involved, you don't create the story. You try to listen. You try to discern what the story is. It's not your story, it's their story."

-Brad Fisher, Just Press Record on Cultish Creative YouTube

Key Concept: This is the difference between being helpful and being destructive. When you listen to someone and start connecting dots to fit your own narrative, you're not helping - you're replacing their story with yours. You're filling in blanks that aren't yours to fill. Real leadership, real friendship, real legacy work is about learning to sit in the discomfort of not knowing the answer, not imposing the pattern, and trusting that the person you're listening to knows their own story better than you ever will. This is humility as a leadership skill. This is the foundation of enabling others to find their own path instead of dragging them down yours.

Personal Archive Note-To-Self: I’ll never forget a financial planning meeting I was in, as a junior team member, led by a senior (re: highly compensated, and celebrated as successful) partner of mine. The client came in and said, “I just got back from a vacation - I saw the Hawaiian islands!”

The partner proceeded to go on a 20 minute discussion of the last vacation he’d been on, how many more islands he’d seen on his trip, and how he flew his own plane between them. The client looked on, interested, but a little deflated. The partner steamrolled right through, and when he finished, dove into the report we were there to review.

I’ll never forget that meeting. In a sentence, I watched the partner take the clients story, impose his own story over it, and enjoy recounting his own travels because - because, I guess, he could? It was so awkward. But what did I know? He was successful, I was not.

Brad wasn’t describing this level of tone-deafness, but he was explaining the core idea here. People have structures for stories in their head. They have ideas of how things fit together. We have ideas too, for our own stories, and probably on theirs, if they share them, too.

But we have to keep that stuff to ourselves. We have to make space for stories to come out and sit. We have to, by listening and engaging, figure out what parts of the story should be questioned, focus-grouped, and analyzed for future purpose, and what parts should just be.

It takes way more skill to enable others to find their own path than to push them down yours. And the payoff of that skill is massive. The net benefit, on humanity, of fully actualized people living their purpose, and not just helping your profits, is a lesson I’m so grateful to people like Chris and Brad for helping me remember.

Legacy question for you: Whose story have you tried to rewrite when you should have just listened?

BEFORE YOU GO: Be sure to…

  • Connect with Brad on LinkedIn

  • Check out Scalable Leadership Group if you're working through a “Second Leap” in your business

  • Reach out directly to Brad at [email protected] if you want to explore structural scalability or leadership coaching

  • Read the books Brad references: Building a Story Brand by Donald Miller and Who Not How by Benjamin Hardy

  • Think about what you're trying to solve "how" for that you should be asking "who" instead

  • Take a moment to reflect on your own Island A and Island B!

You have a Personal Network and a Personal Archive just waiting for you to build them up stronger. Look at your work, look at your life, and look at your legacy - and then, start small in each category. Today it's one person and one reflection. Tomorrow? Who knows what connections you'll create.

Don't forget to click reply/click here and tell me who you're adding to your network and why! Plus, if you already have your own Personal Archive too, let me know, I'm creating a database.

Want more? Find my Personal Archive on CultishCreative.com, watch me build a better Personal Network on the Cultish Creative YouTube channel, and listen to Just Press Record on Spotify or Apple Podcasts, and follow me on social media (LinkedIn and X) - now distributed by Epsilon Theory.

You can also check out my work as Managing Director at Sunpointe, as a host on top investment YouTube channel Excess Returns, and as Senior Editor at Perscient.