What if the way you've been told to grow your business is actually the thing burning you out?
Tom Freedman, CEO of Defiant Enterprises, has spent 28 years owning businesses across industries ranging from health clubs to commercial cleaning companies. Over that time, he's come to a conclusion that challenges the conventional playbook: the traditional approach to small business growth can lead to exhaustion and failure.
Instead, Tom builds what he calls pipeline development systems for B2B service providers, helping solo, micro, and small business owners create an ecosystem that chooses them rather than forcing them to constantly hunt for business. We sat down with Tom to unpack his five-step pipeline system, the five relationship channels every business owner needs to manage, and why being "owner-dependent" might actually be the smartest strategy for 90% of small businesses.
Along the way, he makes a compelling case that authenticity alone isn't enough. You need what he calls "strategic authenticity" to actually grow a real business. He also shares one of the best pieces of advice we've heard in a long time: the rocking chair tactic. If you don't have a rocking chair, you're probably going to want to go buy one.
4:03 — Meet Tom Freedman
5:21 — Entrepreneur Roots
7:13 — Defiant Enterprises
8:49 — Favorite Businesses Lessons
10:30 — Five Step Pipeline System
13:59 — Five Relationship Channels
15:41 — Why Defiant Matters
17:49 — Marketing And Referrals Intersection
19:22 — Authenticity And Business Stage
21:38 — Owner Dependent Brands
26:08 — Showing Up As Yourself
30:31 — Heart For Service
32:35 — Strategic Authenticity
33:36 — People Remember Feelings
34:48 — Mountain Restaurant Lesson
36:24 — Micro Changes Win
38:59 — Values Driven Growth
41:38 — Learned Skills Empathy
43:35 — Rocking Chair Tactics
45:03 — Scaling With SOPs
47:47 — Grace Through Mistakes
49:44 — Behind The Brand Quiz
55:02 — Intentional Go Giving
62:04 — Redefining Success
63:41 — How to Connect with Tom
There's a tension every leader of a B2B service has to navigate: How do you scale without compromising the quality of your services - or the values that drive them? The CEO's Heart for Service is where accomplished B2B leaders share hard-won insights on walking that tightrope.
The CEO’s Heart for Service is a production of Brand3. If you’re a B2B service provider who delivers exceptional service but struggles to get your marketing to connect with the right people, find us at brand3.net. And sign up for our Brand3 Newsletter that only sends marketing insights worthy of your inbox - genuinely helpful stuff for the road ahead.
The CEO’s Heart for Service is also supported by Forge Podcast Company, a turnkey production solution for using podcasts to reach a wider audience, win new clients, and grow. Find them at forgepodcast.co
Matt Wolfe: Hi, everybody. Welcome back to The CEO's Heart for Service. Thanks so much for spending your time with us today. I'm Matt Wolfe, and I'm here with my business partner, one of the founders, and our amazing leader of all things, Orsi Herbein. Orsi, how are you today?
Orsolya Herbein: Where is the applause? Come on.
Matt Wolfe: I know. Where's my applause button for Orsi?
Orsolya Herbein: It's a great day. It's a great day. I'm doing just fine.
Matt Wolfe: Good. I always love when we get a chance to do this together. It's not often enough.
We had a great day because we were talking to Tom Freedman, CEO of Defiant Enterprises. His team is doing incredible work helping B2B businesses, pretty much the same businesses we work with, develop their sales pipelines and referral strategies in a way that's designed for B2B and for small business leaders who have a lot on their plates.
He's a remarkable guy. Orsi, I'm curious, what are some of the things that you picked up on today that you're excited for people to hear? What can they look forward to in this conversation?
Orsolya Herbein: I pride myself on being surrounded by a lot of people that I would call real. They're just really real.
But when it comes to Tom, the raw, honest brilliance that I experienced in the past hour chatting with him, the way he answers questions, the way he speaks, he's not afraid of saying what needs to be said, but says it with respect.
I think of Tom as probably the person that I would look up to for boundaries because of the way he speaks. He's not trapped in the questions or the emotional side of things, but you can see his heart all the way through.
It's another experience to listen to Tom. I'm super excited for our listeners to get to know him.
Matt Wolfe: I am too. When he makes a recommendation, this is what you should do, you believe you can do it.
He dropped a lot of great gems along the way. He's going to talk about learned skills. Often, especially if you're the owner or founder leading a small B2B service business, you feel like there are deficiencies you can't overcome. You score yourself harshly, and he really brings a lot of hope that there are truly learned skills that can overcome any shortcomings or things we need to work on.
We know that in the B2B space, we have to talk up and show up with authenticity. He's got some great ideas about what you need to do that. There are tools and learned skills that help you feel grounded and show up in an authentic way. It's not just this ephemeral thing that people are trying to grab. He makes these things possible.
And my favorite thing, keep an eye out for the thing about the rocking chair. If you don't have a rocking chair, you're probably going to go buy one. Hang in there for the rocking chair. It's some of the best advice I've heard in a long time.
And so, let's get to it.
Matt Wolfe: We're going to introduce you to Tom Freedman. Hi, Tom. Thanks for being here today.
Tom Freedman: I appreciate you having me on, Matt.
Matt Wolfe: The first question we like to dive in with is one that helps us get to know the human behind the brand, to get to know the people behind the services being offered.
Everyone we work with at Brand3 is a B2B service provider offering a service that is some version of, “Hey, let me hold your future in my hands. Let me take care of this really high-stakes, high-trust service for you right now.” Something in finance, something in tech, or, for you, a critical growth strategy.
We know those things don't move forward until a human meets a human, until someone gets a sense of, “I feel like this person really has my back and really cares about me.”
So we try to make sure we catch that part of the story too, along with what the business is doing.
The question we like to start with is: What did you want to be when you were growing up? Because you probably didn't think you were going to start Defiant Enterprises and run referral strategies for people.
Tom Freedman: I don't know.
Matt Wolfe: ...and run referral strategies for people.
Tom Freedman: Matt, we had this discussion earlier. My father was an entrepreneur growing up. He owned his own small business, and everybody around him and us were also small business owners.
It was very normal that by the time we reached high school, everybody around us was asking, “Is there something wrong with you? Are you going to open your own business or what?”
So I don't have the traditional story of working for a corporation and then hanging my shingle up. Mine was very organic from birth. I was already riding in a truck with my father's construction company and engaging in a lot of other small business community activities.
When you ask me what I wanted to be when I grew up, I have no clue. But what I did know was that I was probably going to own a business of some sort.
I didn't understand that it would be seven businesses over 28 years, and I have no idea what's going to happen next.
Matt Wolfe: That's incredible. Could you give us a sense of what kind of business you wanted to start?
Tom Freedman: My dad was my superhero, so I really thought I was going to the blue-collar side. I have the utmost respect for anybody running a general contracting business or any of the trades.
I found my way into owning all different types of businesses. I owned commercial cleaning companies, health clubs, and a slew of different businesses.
I love the chess match of owning a small business. I love that game.
Could I actually do different things? You bet. I think the general consensus is this: If you can add value and build awesome relationships, business is just fun, no matter what you're doing.
So I just love the small business space, period.
Orsolya Herbein: Do you want to tell us a little bit about Defiant Enterprises? Who do you serve, and what is it about on a high level?
Tom Freedman: I appreciate that, Orsi.
We decided to really hyperfocus. When I say “we decided,” it requires iterations. I don't think most small business owners know exactly who they're targeting in the beginning. They have to do A/B testing, play King of the Hill a few times, and figure out what the data is presenting.
You can probably take your best foot forward on that, but data is data. Let's agree on one thing: It doesn't matter what we think. It matters what the marketplace thinks.
For Defiant Enterprises, what we found is that the businesses that resonate with us the most are solo, micro, and small business owners. By my definition, that's $50 million in ARR and below, so we probably extend a little deeper into the maturity of small businesses.
They're in the B2B space, meaning they provide a white-collar service for other businesses. Think of services under the growth umbrella, operations and administration, finance, HR, or IT, which is a huge field for us.
That's our niche. For anybody outside of that space, we're probably going to push you to another partner who's hyperfocused in a different lane.
We've really gone through the throes of perfecting, or at least improving, our commitment to that ecosystem.
Orsolya Herbein: Awesome.
Orsolya Herbein: I do have a follow-up question regarding your many, many businesses, if that's okay with you, Matt. Since you've dabbled in so many different types of businesses, which one is your favorite? Is it the one you're doing right now, or was there a time when you thought, “Man, it was really cool to own a health club”?
What are some of the differences between the different types of businesses that you owned?
Tom Freedman: I would have to say this: My first and last are my favorites.
The first one is my baby. I was still a baby myself when I opened it, and it's still in existence today. That is the health club. My brother actually owns it outright now. He bought out all the shares of my original partner.
The business is alive and well. It's still family-run, and it's been going on for over a quarter of a century now.
I'm really proud of that whole thing. Starting something from nothing and still watching it exist is an incredible feeling.
With a health club, we're directly associated with improving other people's lives. Not to mention, it was a social atmosphere, so we were responsible for relationships, weddings, and all kinds of other things. Really, really cool stuff.
The other one I'm most proud of is the one I own today. I'm not just saying that for the sake of relevance. It's the culmination of what I've learned from other human beings, as well as what I've learned through my own journey over 28 years.
It's really a culmination of adding the most value I can to the marketplace.
Matt Wolfe: Let's dig in on that for a second. We got a great sense of who you serve. In fact, we serve essentially the same people for the most part, which is one reason I think we were so glad to meet each other.
How do you serve them? Can you tell us a little bit about the strategies you're running for people and what you're teaching them?
Tom Freedman: Of course. We've really ironed out our process over time. We have a five-step process that we take all our clients through.
What we're really trying to do is build a pipeline development system that manages all the essential relationships that are relevant, important, and strategic to growing your company.
But in order to do that, we have to start at the forefront. Before moving anyone forward, we always begin with modeling. We need to put numbers to the strategy or plan so everybody can hold each other accountable and understand how to operate with intentionality.
The second step is positioning, and you guys live and breathe in this lane. In fact, it's how we would engage you for some of our own client engagements, past referrals, and all that kind of stuff.
Positioning is about having the right solution for the right audience and the right message. If you're not positioned properly, you don't need me to tell you this: Best of luck to you, my friend. Positioning is key to pretty much anything in business.
After positioning, we move to infrastructure, making people small but mighty. You have to drive the daily rigor in order to drive sales.
Sales obviously starts at the front end, so we look at your marketing, business development, and sales. Then we look at what happens afterward, because you really need to control your client experience.
Finally, we move into the actual building of pipeline development. We're highly intimate with our clients as we build all five channels and make sure they master the ability to have full control over their opportunities, clients, and revenue coming through the door.
We can also build a full team of people around them, including virtual assistants, executive assistants, and all types of support they may need.
The last thing I will say, Matt, is that once somebody becomes a kung fu master or a black belt in pipeline development, they need to make a hard choice: Should I lifestyle the company? Should I exit the company, meaning position it for sale? Or should I scale it?
Whatever that choice is, Matt, we can build a team around you to help you do that. But you do have to make that choice because each strategy is vastly different.
Matt Wolfe: I really love this, Tom. I love that you're thinking about the whole journey with people, right? The foundations of it.
We talk about positioning in a very similar way. We say, “The right story to the right people.” You can't do anything until you do that.
But you're thinking about the middle and the future of where they're going. When I encounter a lot of these referral and pipeline-building strategies, they're really just thinking about the present, moving sales through the door.
You're thinking in a more considerate way: How do we help these people for the long term?
Matt Wolfe: What were the five channels? You mentioned keeping the five channels going.
Tom Freedman: The five channels look like this.
At the very top, obviously, everybody wants clients, so that's channel number one.
Going backward from there, you have your opportunities. These are people who are interested in working through the process to become a new client. That's channel number two: opportunities.
Channel number three is new people entering your ecosystem. In other words, through either a lead or some type of contextual introduction or referral, someone says, “Hey, Matt, meet Bob.” It's about managing that whole process.
The last two channels are partners and prospects.
Partners are all the people who could occasionally give you a referral or contextual introduction. Prospects are people you know who fit your target audience profile or ICP, or ideal client profile. They haven't raised their hand to express interest today, but they could potentially use your services in the future.
If you control all five of those relationships, they're the most intentional and relevant relationships for growth.
The problem I see most people having with all of this is figuring out what bucket people go in, how to manage those buckets, what the frequency should be, and what to say.
It's difficult to learn how to apply daily rigor, put people in the right spots, honor each relationship as it is, and add the most value to each person who fits into your ecosystem as you move along.
Matt Wolfe: That's incredible.
Matt Wolfe: I was looking at your website this morning, and Defiant Enterprises is the name. What does the “Defiant” part mean? Was it, “We're going to do this differently than everyone else. We're going to change the way this works”? Where did that come from?
Tom Freedman: Some people thought it came from my youngest daughter, but it did not. She is my little defiant one, but the name actually came from this, Matt.
After owning companies throughout my life and working with so many other entrepreneurs, what I found is this: The traditional way of owning and operating a company is set up for exhaustion or failure.
It really is.
What people say is, “Let's go ahead and hunt as much as we can for lead generation and take the volume play as our main focus. If we work hard enough, we'll beat the system. We'll grow the company to a level where it actually has the resources to become scalable.”
That's the normal methodology for most small businesses.
The problem is, look back at the data over decades and you will find that most people either struggle for the majority of their business journey that way or end up closing up shop.
So when we say “Defiant,” we mean this: Please don't look at growing your small business to the point where it is exitable or scalable.
Don't look at it in a traditional way. Look at it through a completely different lens. You're building your own ecosystem, and that ecosystem knows and loves you to death. They choose you instead of you hunting them.
Matt Wolfe: Geez, I love that. You're really helping people build a strong community around them, with support and real relationships. To me, that gets to the heart of what so many small business owners feel: They're just on their own and alone.
That's really powerful.
Matt Wolfe: I wanted to look at the intersection of our two services because it was interesting to talk about this the other day.
We've started a program called Scale Beyond Referrals. It's for B2B service providers in the same spaces we're both in: high-stakes, high-trust services.
Many of these business owners have given up on marketing because it became a major source of burnout. They spent a lot of time and money on it, and, to your point, that's just one of many areas where they can burn out. So they gave up on marketing and are living on referrals and word of mouth, very likely without a great strategy like the one you bring to the table.
Our dream for these people is that they learn what went wrong with marketing in the past. They probably weren't taught a relational way of marketing that presented them in all their humanness, including the wonderful sense of who they are, the face behind the brand, the founder behind the brand, and the beating heart behind it.
We reconnect that into their marketing so they can have a broader reach.
But when we say “Scale Beyond Referrals,” we're not saying they don't need referrals. We're saying, “Make more friends. Build a bigger community on the front end.”
Then we want them to find people like you who can help them make the most of that, nurture and develop that pipeline, and bring it to its maximum potential.
I think it's so important for people to have both. I'm curious: Where have you seen that intersection between referrals and marketing in your own experience?
Tom Freedman: You bring up something, Matt, that's really, really important, and that is this: We pass around the word “authenticity,” and when we talk about authentic relationships, nobody wants to meet a fake. Nobody wants to meet somebody who's not comfortable in their own skin.
That same concept also applies to you as an entrepreneur.
There's a confusion that happens when you're at the grassroots stage of a business but pretend to be Jeff Bezos. The strategies that a much more mature, larger organisation uses are not the same strategies you need to apply when you're bootstrapping a business from the beginning.
When I say “business authenticity,” I mean understanding your place in time.
Let's look at marketing. For somebody bootstrapping a business, marketing may mean something like, “I need the perception of my brand when I'm introduced or referred to be what I need it to be.”
In other words, when I meet somebody and they look at my website or LinkedIn profile, it shouldn't look like a three-year-old created it if I'm getting ready to charge them $5,000 a month.
Perception is critical at that stage.
Still, under the umbrella of marketing, you can look at a much more mature company that's leveraging SEO, GEO, and AEO strategies in a hyper-complex, data-driven format, making micro changes regularly.
Both are marketing, but you have to understand where you are in the growth pattern and life cycle of a business to understand what marketing means to you.
It's always important, but what's most important, Matt, is this: Apply your focus where it should be. Don't chase squirrels, and never pretend to be somebody you're not.
Orsolya Herbein: I heard you say earlier that, at some stage, you ask the business owner where they're going, whether they want to exit, sell, or own a lifestyle business.
From what I'm hearing, especially around relationships, humanness, and building a community around the owner, there's a lot of narrative out there that being owner-dependent is bad. There's no value in the business, and so on.
It sounds to me, correct me if I'm wrong, like you're saying that's bullshit. There are very good possibilities of making a lot of money while being owner-dependent if you acknowledge it and decide to capitalise on your own expertise, knowledge, network, and relationships.
You just have to know where you're going. As you said, the strategies for someone who wants to exit and someone who wants to create a lifestyle business, make as much money as possible while they're working, and eventually stop working are different.
Is that what you're saying? Is there actually a lie behind the narrative that you don't have a valuable business if you're owner-dependent? We're sort of on the same page if that's true, and I'm excited to hear your perspective on it.
Tom Freedman: Let me take a couple of different things on that point of view. Oh my gosh, we could have that conversation forever. I'm an uber-nerd about that conversation.
First of all, is it scalable? You bet. I can think of a couple of different names, whether you agree with them or not, that would beg to differ that you can't build a huge brand around a human being, such as Martha Stewart or Tony Robbins.
I think they probably did okay. They're probably affording their mortgages. They're okay, right?
On the other side, while that's not always the case for huge enterprise companies like that, let's look at the grassroots side of things, or the small business space.
Orsi, I would be willing to bet that 99%, maybe that's aggressive, but definitely 90% or more of companies in the small business space should be hyperfocused on revolving their brand around one or a few leaders on the team. It should be very personality-driven.
Why? Because in the beginning, most small businesses are chosen not for what they do, but for who they are.
That may change and mature as they get into the mid-market and enterprise space. But for 90% or more of small businesses, we choose Orsi, we choose Matt, we choose Tom, or fill in the blank, because ultimately, everything else is a commodity choice.
The hilarious part is that small business owners don't have the time or bandwidth, and certainly don't have the luxury of vetting multiple commodities to make a choice in everyday life.
So they rely on personality, trust factors, and things of that nature, or, as Orsi points out, the human behind the brand.
Matt Wolfe: Man, we are really aligned on that point.
Orsolya Herbein: Very aligned.
Matt Wolfe: This is literally something we teach in the Scale Beyond Referrals workshop. I couldn't have said it better.
I think what we've seen is that the marketing industry got a little lazy with all these new digital toys that came out. We thought we were winning in the marketing industry broadly by getting good information out into the world, especially for B2Bs.
If you're a thought leader, you have good information out in the world. There are blogs, social posts, and all these other things.
But to your point, nothing moves forward in this B2B space unless a human meets a human. They need more than the information. They need the human with a real sense of passion and purpose behind them to show up.
That's what we're reprioritising our marketing strategies around. How do we give people an experience of the human behind the brand and celebrate that in exactly the same way you just said?
Tom Freedman: I would...
Tom Freedman: I'd like to hear your opinion on this as well.
I've gotten a lot of pushback from people who aren't particularly charming or don't take to the idea of being the lead singer in the band. They want to stay in the background, so they say, “That's not my personality. I don't want to be the face of the company. Those are the exact things I hate.”
My pushback, and what I'd love to hear your opinion on, is this: You don't have to be vivacious, outrageous, or out in front of everybody with a magnetising personality to build a brand around a personality.
Maybe you're wickedly smart. Maybe you're really good at what you do. Maybe you're trying to attract other people who don't want that vivacious personality.
Nonetheless, your brand is your brand, and it still has to be built around why the company was created in the first place, which usually comes down to a single individual, if not a few.
Orsolya Herbein: I...
Matt Wolfe: Okay, now we're preaching. Now we're going to church a little bit here.
When you come to marketing in general, a lot of people, when you present them with great messaging, say, “That's not crazy or weird, or something people have never heard before.”
And we're like, “No, it's true, it's clear, people are going to understand it, and that's how you win.”
It's the same thing with the humans. People get confused and think, “I have to be like a talk show host. I have to have this vivacious personality.”
No, you just have to be you. People have followed you for five, 10, 20, or 30 years because of who you are. Just show up and be you.
There are a couple of things that make that easier. One is that when you're trying to find the ideal client and target the positioning we were talking about earlier, we're asking people to pull from their real lived experience, not a theoretical person they think they should reach.
Who are the people you've connected with best in the past? Who are your people? You're going to vibe with those people if that's part of the equation.
Orsolya Herbein: It's the clarity of the message, Matt. When you know what to say and what to say to that ideal person, I think it's easier to show up.
Sometimes, you're right, Tom. Especially when someone is an expert, they can sound overly technical. It's really difficult to decipher the technical language because the value they bring to the market isn't necessarily in gigabytes or bits or whatever. It's in time savings or something else.
How do we translate your message so it resonates with the person you're speaking to?
Once you have that key, which is also the positioning, how you show up, and the perception you create, along with clarity and an easy understanding of the value you bring to that community or person, I think that, married with knowing who to talk to and who you vibe with, is really going to make it much easier to show up and communicate.
Matt Wolfe: The clarity of messaging is huge.
The other thing I was going to say is that there are different ways to show up. People have different gifts when it comes to communication.
We had a friend of mine, Macy Robison, on several episodes ago. I'd recommend people look her up. She's doing great work helping people figure out, “What is my natural, native language as a thought leader?”
You might not be a public speaker, but you might be great in a workshop setting. You might be great one-on-one. You might be good on camera. You might be comfortable in a podcast setting.
There are going to be different environments and ways of communicating that are more native and natural to you. Part of our job is to help people discover what that is and lean into it, rather than force them into a place where they're uncomfortable. That could be counterproductive.
Tom Freedman: Yes.
Matt Wolfe: So, Tom, I think you have an incredible gift. We're talking about how we look for difference-makers, people with a heart for service, on this podcast. Every time I've met you so far, you show up with that engine revved up.
You hop on camera with somebody, and I immediately get the sense that this guy cares. This guy is digging in and really wants to make a difference. I don't know how you keep it going, but the engine is running.
What does it mean to you, as you translate that onto your team and think about your company as a whole, to deliver great service? We call this The CEO's Heart for Service. How do you know when you've really nailed it?
Tom Freedman: First of all, Matt, that's so kind of you. I really appreciate the kind words.
Some of it comes naturally, but the second thing is that it's a skill set I think every entrepreneur should have: Never forget that people will always remember more how they feel than what you say.
If you're not showing up, even if you're not having a great day, I would rather see you cancel the meeting and show up as your real self. Or, if you do have to show up, tell them ahead of time, “This is not my norm. I want to respect our time, but I'm not feeling like myself today.”
Try to bring it as much as you possibly can. In the world of marketing, networking, business development, and things like that, we're constantly inundated with new messages, new people, and everything else. It's exhausting.
The only ones that really stick out are the ones that bring it.
The second thing I'll say is that I love authenticity, but I'll add one more thing to it: Authenticity doesn't pay the bills.
Tom Freedman: It opens the doors but doesn't pay the bills, right? Controlled or intentional authenticity is what grows a real business.
If you understand how to bring your normal self at your best, but also control the entire performance, you can bring high energy or your best energy. But what do I say? What do I ask? What does my background look like? What does my website look like? What collateral documents am I going to follow up with?
Everything around it needs to be focused on the feeling you're bringing to the situation. If you ever lose sight of that, you're going to struggle immensely.
We're all emotional beings that thrive on feeling. So if you're not good at that, you really need to be a student of...
Matt Wolfe: Yep.
Matt Wolfe: That's what we're both working hard to do: make sure people feel they have a firm foundation and really understand the plan and the plays they need to make.
To your earlier point, where am I in the journey? And to Orsi's point, what is the story I need to tell?
All of that cumulatively gives people the confidence to move forward and feel grounded in where they are.
There's another thing you said just a second ago. We were talking about how people remember how they feel, not what we say. It reminded me that we also have to remember what moment in their story this is for them.
Whether they're developing their referral strategy with you or rebuilding their brand and trying to find the messaging that will grow the company, they're pausing to take stock of where they've been, where they're going, and how they'll successfully grow the business.
It's hard for anyone to pause and stop when they're running a small business. It's hard to take a break.
But they're in this very vulnerable position. They're risking a lot of time, energy, and money on the idea that this is going to improve their future.
Matt Wolfe: It reminded me of something. We were just talking about this because I took my family to a ski resort in Washington State. All the ski resorts do fun stuff in the summer.
I won't call this one out by name, but there's a resort that has a restaurant at the top of a mountain where you're face-to-face with Mount Rainier. You're just in heaven. You can have a burger and fries, or they have fancier food too. They have this lovely little vintage restaurant that's been there forever, and you go there and have this amazing experience.
We went up there, and it was great. The views were unbelievable. The food was great. But the servers, I think, were still doing business as usual. They were getting through it like they were running a bistro down in town or working at an Applebee's.
The only thing that let me down was realizing that they had lost their sense of how special this place is.
The gondola that gets people up there just keeps running all day long. It keeps pumping people out and dumping them off into this thing. So you could fall into that mindset. But everyone who gets off that gondola is seeing a view of the Earth, nature, and wonder that they've never seen before. Many of them, like us, have been waiting years to eat at this restaurant.
I took everything I wanted to take from the experience, but they missed the opportunity to lean into it with me.
So we have to remember that people are in this moment of great risk and great potential. It's not business as usual for them to sit with us and do this work.
Tom Freedman: The devil's in the details for all of that, Matt. And you know this, it's an evolutionary process. As a business owner, you have so many different things to solve. It's just so much, right?
The hard part is coming up with some type of process that allows you to isolate and correct things when they don't work out the way you want them to or when they need improvement.
I watch so many business owners get bombarded by the number of things they can change, so they change nothing. All they do is remain reactionary and run around like an idiot every single day.
But here's the other side of things: doing nothing is the wrong answer, but so is trying to do too many things at once.
And by the way, if you went to that restaurant a couple of times, Matt, you would applaud the fact that they just got one thing better, not that they did an entire overhaul.
I think a lot of small business owners believe people want progress and change. They don't need a complete facelift or an overhaul. So make these micro-changes and constantly commit to becoming a master of this over time.
It's not going to happen tomorrow, and I don't need to solve everything. But I am committed to service, and I'm open and aware that I just need to keep changing in small, tiny increments as I progress.
If you go with that mentality, it makes things more palatable. But here's the best part: your customers and your audience prefer it that way.
They don't want you to do too much. They want you to show them, "See? I listened, and I changed." And then again, "See? I listened, and I changed." Not a miraculous overhaul every so often.
Matt Wolfe: It's a wonder- that's wisely said.
Orsolya Herbein: Our coach told us that every morning he wakes up and tells his son, "Hey, are we going to be good or are we going to be better?"
Being better than yesterday is ultimately going to get you to good. But good is just so far out, you know? I love it. It reminded me of what you said.
Tom Freedman: That's it.
Orsolya Herbein: I do wonder where you put two and two together to get here. Like me, I bought into the 10X mentality and started delegating relationships. That's when my business started tanking, and I thought, "Wait a minute. Something's not right here."
Where was your challenge or lesson in your business career when you realized that growth shouldn't come at the expense of your values?
Tom Freedman: You mentioned it, Orsi: growth shouldn't come at the expense of your values. The reason I'm doing what I do today is that I want to give business owners access to the education they need to mature their small businesses in the right way, so they have optionality.
In other words, you can choose because you've built something great, right?
The way you do that is by having a clear understanding of what we talked about before: where you currently sit in the process of building your company and where you should focus your efforts. That is paramount.
My ecosystem consists of solo, micro, and small business owners in the B2B space. These people need to get the plane off the ground first by understanding how to build the relationship-based model they need.
They need to be able to develop and control their relationships so they can get contextual introductions and referrals. Not because that's going to be the be-all and end-all forever, but because they need to do that now so they have the capacity, power, and optionality to do other things down the road.
But if you never get there, all you do is live in a state of survival, trying a million things and then complaining about them not working.
"Well, I tried Google Ads. Well, I tried networking. Well, I tried this. I tried that."
Stop trying. Focus on what you're supposed to be doing at the right time, and you will continue to mature in a fashion that allows you to do all kinds of amazing things.
Pretend to be somebody you're not, and you will lose all your money. Have fun being exhausted and frustrated for the majority of your life as an entrepreneur.
Orsolya Herbein: So you're teaching your clients that some of the things people think are part of their personality are actually learned skills.
Tom Freedman: I'd say the vast majority of them are learned skills. And if something comes naturally to you, Orsi, like we talked about, authenticity may be one thing that opens doors. But without intentional, controlled, or strategic authenticity, it still doesn't get monetized in your company.
You need to understand how to leverage it properly.
So yes, some of these things may come naturally to people. Nonetheless, you still need to learn how to leverage them properly. That's typically not something embedded in your brain when you're born. It's a learned skill.
Orsolya Herbein: I love that. I sometimes say the same thing about empathy. I think a lot of people believe that to be empathetic, you have to have a certain personality.
But in branding, what we do all the time is place ourselves in other people's shoes. We see things from the outside in and pretend we're a customer of a particular company so we can understand their perspective.
I fully believe empathy can be practiced and learned. You can look at something from someone else's perspective and realize, "Oh, these were my blind spots."
So it's the same thing. Maybe what I'm saying is what you're saying: you might not be naturally empathetic, but you can add empathy as a strategy to your day-to-day work. That allows you to understand other people's perspectives and how they view you when they're interacting with you.
I love the idea of leveraging these skill sets, even if you don't have them naturally.
Tom Freedman: Orsi, that's what I call rocking-chair tactics.
One of my number-one tools for becoming a little wiser, although I'm completely an idiot in so many different ways, is adopting strategies like this in my personal and professional life.
If you're unsure of the answer, sit your tail in a rocking chair and think about it before you react or make a decision.
Empathy works the same way. If you truly want to be empathetic, you need to sit in a rocking chair. Maybe not an actual rocking chair, but take a step back. It's okay to breathe and let a conversation sit for a second.
Sit there in the moment, in your own little virtual rocking chair, and put yourself in their shoes before you jump back in with a response.
When you do that, you'll be much better at empathy.
Taking those pretend rocking-chair moments, even when a rocking chair doesn't exist, can be the best tool you can use in your personal and professional life. Or you can buy yourself a real rocking chair and sit your butt in it.
Matt Wolfe: That's a great image to hold on to. That's going to stick with me for a while.
Orsolya Herbein: For sure. I love it.
Matt Wolfe: As we talk about these learned skills, the things we learn along the way, I want to turn this examination back to your own journey for a second.
What we like to get to in this podcast is that we meet people like you who care so much about the people they serve. As you've grown, there's this question that lingers throughout your growth or scaling story: How will I keep taking good care of my people as I grow?
I'm curious, where have you seen the challenges along the way as you've grown and scaled this company? What lessons have you learned about taking great care of your people?
Tom Freedman: Standard operating procedures. As you start adding more people to your team, whether they're contractors, employees, or whatever, you can't do it yourself. You need people to join your team.
That includes vendors, partners, referral agents, and the whole thing.
As the business grows, if you don't take full control of your standard operating procedures and hold people accountable for culture, as well as everything else, then standards will drop. You'll lose your ability to serve your clients the right way.
Lean into this question: "If I want it done the right way, what is the right way? How do I map this out so other people understand it and it can be repeated?"
Your standard operating procedures don't have to be created alone. In fact, I highly recommend getting other people involved so you can bring multiple perspectives into the process.
Create standard operating procedures around two things: culture and performance.
When you have both of those pillars, you can do some pretty amazing things.
So, in short, if you want to continue growing and scaling while maintaining that level of service, good luck if you can't create awesome standard operating procedures.
Matt Wolfe: That's a great reminder. We keep finding as we talk to people that the answers to these questions about scaling and growth are usually very simple, very human things: discipline, awareness.
What else have you learned along the way? Have there been any moments when you thought, "I can't believe I didn't catch that sooner," or had one of those moments where you wanted to smack yourself upside the head?
Tom Freedman: That's everything, Matt.
Matt Wolfe: Oh.
Tom Freedman: I think you need to give yourself grace. That's one thing I've learned along the way.
So many people, especially entrepreneurs, are afraid. They're afraid of taking the next step, handing something off, filling in the gaps, and so on.
But you need to give yourself grace. If you want to add as much value as you can to the world, you must be willing to make mistakes. Sometimes those mistakes are really harsh.
But if you keep the intent in mind that this isn't selfish, that you're always doing your best for the people you serve, it's okay to make mistakes or fail.
That's how people mature and how people come to value them in the end.
For you and Orsi, when you meet somebody who really needs marketing help, they don't want to do it themselves for one big reason, and it isn't time. It's because they're trying to leverage you, a master of your field, someone who has dedicated their life to becoming great.
The one thing I've learned, Matt, is this: If you want to be great, give yourself permission to mess up or make mistakes, but under one condition: the only way you make a mistake is if you truly had others at the centre of your heart.
If it's about you, your mistakes will crush you, and they should.
But if your mistakes come from truly wanting to do the best for others, that's just part of the process.
Matt Wolfe: Very well said.
Orsolya Herbein: Love it.
Orsolya Herbein: So, Matt, are you ready to have some fun?
Matt Wolfe: Let's jump into our... Okay, so, like I said, we want to get to know the human behind the brand. We've both been saying that, right? How do we celebrate the person whose heart is really driving this mission and purpose forward?
We have a thing we call the Behind the Brand Questionnaire, and that's exactly what it is. If anyone has been listening to you this long, they're probably interested in working with you. This will help them move forward and get to know who you are as a person and what makes you tick.
It's seven questions about who you are and what makes you tick. It's pretty harmless. Are you ready to dive in?
Tom Freedman: Let's do it.
Matt Wolfe: Okay.
Orsolya Herbein: What's your go-to karaoke song, or what song do you wish you could sing?
Tom Freedman: Oh my gosh. It would be "Sweet Caroline."
My grandmother, who is represented by one of my tattoos right here on the moon, had a saying: "Love you to the moon and back." She said it sincerely to everybody she truly cared about for more than 90 years. She lived to be over 100 years old and was one of the best people in my entire life.
Her favourite song was "Sweet Caroline." Not only do I sing it, but my entire family and all our close friends will stop what they're doing when that song comes on and sing at the top of their lungs.
So that would probably be my number one answer.
Orsolya Herbein: Amazing.
Matt Wolfe: That is awesome. Now we know you're the guy with the grandma tattoo front and centre, where everyone will always be able to see it. Who wouldn't want to work with you now?
Tom Freedman: Let's go.
Matt Wolfe: Okay. What's the last thing that made you laugh out loud?
Tom Freedman: I think it was probably my daughter. She finished her shower, got dressed from head to toe, and it was the first time she needed no help.
She came downstairs and said, "See, Dad, I did it all by myself." She had her shorts on backwards, two different-coloured socks, and a different pyjama top.
I thought it was the cutest thing ever and burst out laughing, only to stop myself because I couldn't keep laughing. I had to give her a hug and say, "Awesome work."
So that was probably the last thing on the list.
Orsolya Herbein: That's awesome. And she probably picked those things because she liked them, right? We should all dress like that, honestly.
Tom Freedman: Right.
Orsolya Herbein: So what's your favourite way to get away from it all?
Tom Freedman: I like the mountains and the beach equally. But when I really have to get away, sitting beside the calming waves of a beach is hard to beat.
I think life is best lived in board shorts or a bathing suit. Finding different places to go doesn't have to be expensive or exotic. It's about finding an enjoyable spot where you can appreciate the weather and, in the evening, sit and listen to the methodical waves crashing.
I think that's probably the best way to spend your time.
Orsolya Herbein: You know what? A rocking chair on the beach.
Tom Freedman: It is, yes. Well said. I'd never thought of it that way, but you nailed it.
Matt Wolfe: That's a song title. There's a song in there somewhere.
Tom Freedman: That's right.
Matt Wolfe: "Rocking Chair on the Beach." Next question. I love this one. What smell reminds you of a specific place or time?
Tom Freedman: Okay, this is a really weird one, actually, Matt. We celebrated Christmas early on, and I remember being super young when we got this one book. I can't remember what it was called, but you opened every page, and each page had a scratch-and-sniff section where you could scratch the pine cones and things like that.
That smell, when we get around the holidays, immediately brings me back. Even if I smell it outside that time of year, it takes me right back to that same place.
It's all because of this little book. I think I was three, four, or five years old, and it's ingrained in my entire DNA. I find that extremely powerful.
Matt Wolfe: I definitely remember the pine-scented scratch-and-sniff sticker. You just took me back to grade school. We had sticker collections, and you'd get those. They were so big when I was in school, and all those scents bring me back to sitting at my little tiny desk.
Tom Freedman: Like the strawberry eraser and stuff that smelled like strawberries. That's wild.
Orsolya Herbein: I'm going to insert a question here, if that's okay. Are you a go-giver?
Tom Freedman: That's an interesting question, right? I think the concept of go-giving, at its heart, is a fantastic idea. I really do.
What I also need people to be aware of is the idea that if you give enough, it will come back to you, that you will receive. That's a falsehood.
If you aren't intentional about how you approach it, you rarely add enough value for other people or yourself. So the general concept that if you're genuinely trying to help others, they'll help you in return is correct. Just be very careful about how you apply it.
A great example is the networking world.
"Of course, I meet all these people and make 80,000 introductions, but I haven't received one good referral yet."
Well, be careful. You need to look back and figure out exactly what type of value you think you're giving and how you're actually interacting with the people you're giving it to in terms of reciprocity.
I hate to go off on a tangent, but that's a very touchy subject in our world. You want to be a go-giver, but not blindly.
Orsolya Herbein: So basically, what you're warning against is the intention. Don't give to receive. Give because you're a giver.
You don't make it your strategy in a way that's devious or dishonest. Is that what you're saying?
Tom Freedman: The other thing, Orsi, is that there's a difference between personal and professional life.
Whether you're a team of one with no employees or part of a very large team, you still work for your company. Everyone has roles and responsibilities within that company.
So be careful that your go-giver mentality doesn't consume all your time and resources while you're giving to the wrong people or in the wrong way.
If you're intentional with your go-giving and have a real servant's heart, you can take care of both sides, the intrinsic and extrinsic.
But if you're unaware and blindly give, give, give, then wonder why you never receive, receive, receive, don't be shocked.
Intentional go-giving is probably what I would say.
Orsolya Herbein: Tom, I haven't known you for very long. It's probably been about a month, but this is something I already love about you.
The straightforwardness of the way you speak is wonderful. I think one of your greatest attributes so far is that you're skilled at saying things in a way that comes across as nothing other than the truth.
It's refreshing to hear, so I appreciate it.
Tom Freedman: Very kind. I feel the same about you, which is why I was so excited to get this relationship going.
But the other thing I would say, Orsi, is that it took a long time, and I'm still trying to improve. This doesn't happen overnight.
Like most people, I had tons of fears about being comfortable saying what I wanted to say. I stayed reserved or said what other people wanted me to say.
It's all part of the process. But for anybody, the quicker you can get to authenticity with a kind heart and genuinely follow through with it, the more people will respect it.
And if they don't, that's an immediate qualifier or disqualifier for who you build your ecosystem around.
Trying to make everybody happy is a recipe for disaster. It's impossible.
Orsolya Herbein: Sorry, Matt. I went off script, but I needed to ask that question.
Matt Wolfe: No, that was wonderful. We've got three questions left in our questionnaire. You have the next one, Orsi.
Orsolya Herbein: What is one day in your life that you would like to relive?
Tom Freedman: One day I'd love to relive? I can think of multiple days, but one would be the first day we opened my first business.
My mom and I were sitting behind the front desk of Athens Health Club, our fitness business, and it suddenly hit us, just before the first members walked through the door, how dumb we really were.
I remember sitting next to my mom, about to open the doors, and we were looking at each other thinking, "What in the heck are we doing opening this business right now?"
I was just a kid, and she was helping me out. But we had a full-fledged business.
It was the absurdity of being a young, inexperienced kid. Nonetheless, it was the start of everything.
I still remember the feeling of looking at my mom right next to me before we opened that business. It was such a powerful feeling. This was the beginning of it all.
Orsolya Herbein: Wow, I love that.
Matt Wolfe: What three words would your loved ones use to describe you?
Tom Freedman: Pain in the ass.
I think they would probably use a variety of words, to be honest with you, Matt. But in my family, I got a combination of both my mother and father.
I've been relentless for 28 years, nonstop trying to do my best to create something great. It's been laced with the good, the bad, the ugly, and everything in between, and they've supported me all the way through.
They mean a ton to me, and no matter where I was, good, bad, or ugly, they were always there.
The wonderful thing about being a pain in the ass is that they genuinely admire the fact that I've never given up, and neither have they.
It's a nonstop, relentless battle of waking up every day and trying to do your best, or, in Orsi's words, becoming better.
I'm not sure if those are the exact three words, but it's crossed their minds.
Matt Wolfe: It's so funny. I'm surprised no one has ever thought of that before, but that was great. All right, Orsi, bring it on.
Orsolya Herbein: Last question. What would it mean to have truly succeeded in your work? Not your company, but you.
Tom Freedman: Personally, I don't think success exists. I think the closer you can get to letting go of the concept of success and saying, "I chose to commit myself to this. I can never be perfect, but I will do everything I can to become better every single day until I die," the better.
That, to me, is success.
But putting an actual definition on success only sets you up for gaps between where you are and where you want to be. I spent too many years of my life focused on the gap between where I was and where I wanted to be, and it's a really poor way to live.
The wisdom I've gained from those rocking-chair moments over the years has taught me this: Wave goodbye to the entire concept of success. Enjoy what you do, and do your best every single day at what you're doing and who you're serving.
Orsolya Herbein: So much wisdom.
Matt Wolfe: Tom, I have no doubt that, just from this experience, your clients look forward to their time with you every week, or however that's structured.
I know they look forward to spending time with you because they're going to feel better on the other side in a hundred different ways.
It's been a joy getting to know you and getting even a taste of how you work with people. The depth of your care for them is wonderful.
Matt Wolfe: For people who might want to contact you, what's the best way to reach you and Defiant Enterprises?
Tom Freedman: If you're a good human, I always have room for other good humans. You can email me. I'm sure Matt and Orsi will share my email address.
You can also DM me on LinkedIn or visit any of the resources on our website.
I'm accessible to any kind-hearted professional looking to do good work, so don't feel bad about reaching out.
Orsolya Herbein: Amazing.
Matt Wolfe: I love that. Thank you, Tom.
Orsolya Herbein: Thank you.
Matt Wolfe: And from our side, if you're a B2B service provider offering high-stakes, high-trust services but you've struggled with marketing or feel like you've wasted too much time, money, and energy on it, we'll help you understand why that happened and turn things around through our Scale Beyond Referrals programme.
The best way to engage with us is through our introductory workshop, which you can find at scalebeyondreferrals.com.
Spend 90 minutes with us. We'll help you understand why things haven't worked in the past, see how they can work in the future, and turn that corner by changing your perspective on how marketing can work.
It has everything to do with what we talked about today: how we celebrate you as the human and the face of the brand, and help people get to know you sooner through your marketing.
That's what we do over here.
Other than that, Tom, we're honoured that you spent this time with us.
My name is Matt Wolfe, and this has been Orsi Herbein. We have been your hosts for The CEO's Heart for Service.
We'll see you next time.
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