The High Cost of Not Knowing
The High Cost of Not Knowing
There’s a belief I hear far too often: “I should already know this.” It shows up in quiet corners of coaching calls, inside mastermind DMs, and especially when entrepreneurs start making real money. But this belief—this fear of looking stupid—could be the very thing that sinks your success.
In a recent episode of The Amanda Kaufman Show, I sat down with my friend and fellow coach, Justin Lund. What unfolded was a powerful, no-holds-barred conversation about what it really costs to not ask questions, to avoid the uncomfortable, and to run your business by instinct alone.
Let’s talk about the hidden expense of not knowing—and how to shift from panic-led decision-making to empowered leadership.
You Don’t Need to Know Everything—But You Do Need to Ask
Justin shared a story that stopped me in my tracks. One of his clients paid nearly $100,000 in taxes—money she could have saved if she’d just talked to a CPA four times a year.
But she didn’t. Why? Because she didn’t want to feel dumb.
Let that sink in. The cost of not asking was nearly six figures.
And Justin’s not just teaching this—he’s lived it. He built a business that scaled to over $50 million in revenue. But without the right support, without asking the “obvious” questions, he lost it all. He went through addiction, jail, financial betrayal, and four and a half years of legal hell—all because he didn’t know what he didn’t know.
His lesson? Don’t confuse being the visionary with being invincible. If you’re not asking questions, you’re gambling with your business.
Your Role Must Evolve—Or Your Business Won’t
As entrepreneurs, we usually start with a craft or skill—something we’re good at and love doing. But that skill doesn’t scale. At least, not on its own.
Justin broke it down perfectly: If you started your business baking cookies, your growth eventually has nothing to do with baking. It’s about managing people, building systems, navigating customer service, and integrating tech. In other words: business becomes about the business.
If you don’t evolve as a leader, your growth becomes your ceiling.
What got you here won’t get you there. And sometimes, holding onto “your thing” is what’s holding you back.
You Don’t Need a Silver Bullet—You Need a System
Here’s another trap we fall into: looking for the mythical “right person” to fix our business. The magical COO. The perfect operator. The unicorn hire.
Justin calls it unicorn hunting, and he’s not wrong.
We romanticize the idea that someone else is going to come in and clean up the mess. But if we don’t even know what we’re asking for—if we haven’t done the work to get clear ourselves—no hire is going to save us.
That’s not leadership. That’s delegation without direction. And it never ends well.
What You Can Do Right Now to Avoid the Expensive Mistakes
Justin’s advice is gold, and I want you to hear it loud and clear:
Meet with your CPA quarterly
It’s not about being an expert in taxes. It’s about knowing enough to ask smart questions and make informed decisions.Talk to six professionals before hiring
Whether it’s a lawyer, a bookkeeper, or a coach—don’t hire the first one who sounds good. Interview six. Compare. Decide from a place of clarity, not desperation.Don’t mistake silence for strength
Being afraid to ask doesn’t mean you’re weak—it means you care. Real leaders ask the questions that protect their team, their vision, and their legacy.
What This Means for You
If you’ve ever caught yourself saying, “I should already know this…”—pause.
That thought isn’t a red flag. It’s a reminder that it’s time to ask.
Because the real cost of not knowing isn’t just financial. It’s the missed opportunities. The burnout. The slow erosion of confidence because you’re carrying what you were never meant to carry alone.
Ask the question. Call the expert. Have the uncomfortable conversation.
That’s leadership.
That’s scale.
And that’s how we do what matters.
Chapters List
00:00 Introduction to Justin Lund's Journey
01:31 Breaking Through Invisible Ceilings
03:32 The Shadow Side of Success
05:33 Overcoming Personal Struggles
09:27 Navigating Financial Challenges
12:28 The Importance of Financial Awareness
14:38 Asking the Right Questions
18:09 Finding the Right Professionals
22:56 Connecting with Justin Lund
Full Transcript
Justin Lund (00:00)
as an entrepreneur, we've we get a little romantic and we're really good at solving problems. So we think there's somebody
out there I know what I just need to find them and they can make everything better so that silver bullet thing is dangerous
Amanda Kaufman (00:09)
Yes.
Well, hey, hey, welcome back to the Amanda Kaufman show. And I am delighted to introduce you to my friend, Justin Lund. Justin and I run in similar coachy circles. We believe in mentorship and we just hit it off inside one of our common mentors. And I was just blown away by Justin's story. So Justin is a very successful businessman, but he has also had somewhat of a roller coaster experience.
And so many of the people that I talk to in my community, they are afraid of that roller coaster. They're afraid of the dips. And Justin has a beautiful comeback story and some wonderful things to share. Hey, Justin, welcome to the show.
Justin Lund (01:12)
Thank you. Thank you for having me. I'm excited to be here and dig into it with you.
Amanda Kaufman (01:17)
I'm super pumped, super pumped. So Justin, just catch us up on like where we are today. You help founders to break through those invisible ceilings you call it, when just like hard work and hustle isn't cutting it anymore. So what does that really mean?
Justin Lund (01:31)
Mm-hmm.
means that typically we reach a point where the business that we started is no longer the thing that requires our time and attention to get to the next level. So if you start because you like baking cookies, you know, simple analogy, then your recipes and your ability to put flour and sugar and the mixtures and you know, that's what gives you that initial level of success. But if you hire three people and everybody wants your cookies and you're growing and you're in all these different stores all over,
You're now dealing with problems and issues and demands upon you that have very little to do with your ability to bake. So that's where people make a decision, sometimes not consciously, but they need to decide whether or not do I want to go to the next level of growth and start becoming a person that actually deals with building people, managing human resources, developing inventory management and customer service protocols and AI usage to like handle.
chat bot supporter, you know, whatever else might be part of the business, which again has very little to do with cookies. So, and people sometimes making those choices more conscious sometimes than others.
will often shortcut a few of the steps that they, that I think they should take, you know, so instead of trying to delegate an awful, some of the basic work that could keep them in the kitchen longer and keep them baking, which is their sweet spot, you know, pardon the pun, but.
They look at bringing in a COO right out of the gate. You know, like if I could just find my operator and I think I call that unicorn hunting. know, you're thinking that there's this mythical creature out there that's going to come in and just make everything better and you usually reach that point because you've had a year or two of just kind of smashing your head against the wall or that ceiling that I mentioned, you know, you just kind of bump into that. And so that as an entrepreneur, we've we get a little romantic and we're really good at solving problems. So we think there's somebody
out there I know what I just need to find them and they can make everything better so that silver bullet thing is dangerous
Amanda Kaufman (03:29)
Yes.
It is dangerous. I love this conversation. It's like the shadow side of success, you know, because if you spend four minutes on the internet, you're gonna see people screaming from the rooftops, you know, just do this to make money, just do this to make money. But it's a far more interesting conversation, I think, after that initial success of, okay, I'm offering a product or a service that people, you know, desire, they want, cash is starting to flow.
And I remember one of the first big bumps in my own business as a coach, I started out doing high ticket private coaching. My calendar filled up beyond capacity because I didn't really have the math done about how many spots I could really take. And it robbed my marketing time, my sales time, and I had none of the right kind of help, but I was spending so much money on the wrong kind of help for that particular challenge.
Justin Lund (04:24)
Yeah.
Amanda Kaufman (04:26)
I felt, think with that first big blip in my business, which by the way, I almost tanked it, because cash is king and if you run out of that cash flow, boy oh boy, watch out. And that put me in a pretty flat panic then because no one had really suggested to me that there was a dark side to success or rather that would, know, that money wasn't gonna solve everything, making sales wasn't gonna solve everything. So talk to a little bit about why you're so inspired to help.
you know, service based businesses with this shadow side of success and like helps them unlock their next level of potential.
Justin Lund (05:03)
Yeah, I guess one of the main drivers that I feel called to try to share some of my experience and story is because I've gone through, I well, I've had a couple of dark turns into the dark side myself. So maybe that's the dark side of business is kind of like my, my vibe, my sweet spot. But I got, had some trouble with substance abuse when I, in my just got married, had a very young family and was in sales to support going through college and
I got into drug addiction, pain pills, and so I had a habit there that was just atrocious, hard to, like virtually impossible to kick. And it was maintaining that facade and trying to keep everything looking like it was okay and going good. And then everything came crumbling down after a couple of years of that because I couldn't sustain it and the debts were out of hand and out of whack. And I ended up going to jail a couple of times and then rehab for a six week stint.
And I love that, like I because I was a fan of psychology. That's why I like sales, because I could use some of that psychology. I took psychology classes in college, but I didn't want to be a therapist or social worker or anything that didn't did nothing for me. But I like the idea of learning how to understand what's going on in our mind and how people think and what drives things. So sales was a good fit, but the drugs were not a good fit. Never are.
But the rehab gave me tools and frameworks that I could put my thoughts through and gained leverage over myself and my thoughts and what made me tick and knowing who I was and some of these things. So after that stint, I grew a business fairly rapidly over the next couple of years, reached multimillion dollar revenues, grew so fast that it scared the hell out of me. And I
looked for people to help me where I wasn't good. Like I'm not good with numbers. I don't really know how to do taxes. And so I brought people into my world willy nilly, like without due diligence, without any second thought, Amanda, like just like, okay, you can help sweet. Yes, I need to help. And they took advantage of me. It took me to the cleaners. The business grew. The third and fourth year, was like 30 million, 46 million.
Amanda Kaufman (07:08)
f-
Justin Lund (07:14)
50 something million dollars of revenue and I mean it was growing fast. was big. We had a hunt almost a hundred employees at one point and the short version of that story is as that began to wind down and we made an exit out of some of that I had no
that was all taken from me and siphoned away through a complex series of financial schemes and shell companies that took me four and a half years of litigation to just begin to understand where it might have gone. And I still don't know entirely all of it, but I was able to get out of that and settle that.
Amanda Kaufman (07:32)
and
Justin Lund (07:49)
lawsuit four and half years. It's all I did every day like eight hours a day. I'm reading stacks of legal briefs and financial reports. Remember, I'm not good with numbers. I'm not a good numbers guy. It was a forcing function like the world and the universe was saying, well, you better get good. You better start figuring it out and get your head out of the sand. So I think those two experiences of just dealing with that and then having to
Just do whatever. Both times, both with jail and the drugs and then with the financial situation, there was the potential with drugs. It was like right in front of my face. I could have gone to prison with the financial stuff. There were tax returns that were falsified and had somebody wrote my signature on tax returns and it clearly wasn't my signature. But it turns out the IRS doesn't really care. That's it was my businesses and therefore I was the one responsible. So
Amanda Kaufman (08:44)
yeah, it's the ownership accountability, right? But then that means that after building a business to have 100 team members and, you know, have have millions and millions of dollars of revenue success to then have to essentially live in it. And you didn't even get to keep the business, right? Like you you had to liquidate and separate from that experience and then to spend nearly five years just every day reliving.
Justin Lund (08:44)
I had
No.
Amanda Kaufman (09:12)
That nightmare, my gosh. And so.
Justin Lund (09:15)
Yeah, it
was five years before that I relived in very much as minute of detail as I could put together for the next five years. So it was a weird time of life for sure.
Amanda Kaufman (09:27)
Very challenging. Now you're obviously on the other side of it. So what happened? Did you get things kind of to a place of resolution in the end or what ended up happening?
Justin Lund (09:30)
Mm-hmm.
Two degree. Yeah.
So what I had to do is I filed different tax returns that basically said this is the best that I can do with the data that I have and I'm going to try to go get more data. And those tax returns said that I only IRS millions and millions of dollars in unpaid taxes. So and the counsel that I got at the time was you could hope that nobody ever looks and then you just, you know, just stay quiet and slip off.
I'm like, well, what happens if they do? What if I'm somebody? What do you mean? If somebody looks like, well, if you get out of it, you'll probably go to prison because I mean, it says their tax returns filed say very minimal income. And you know that it was tens of millions of dollars like that doesn't just get swept under the rug. mean, it's it's going to all come back and point to you. like, but I don't have any of the money, like zero of the money I have.
And that's where I had to file the returns and to just try to cooperate and work with the IRS. And they're not the easiest to cooperate and work with.
You think taxes are complicated and they're they're they're pretty clear cut when they know you owe them money. This is pretty straightforward. So anyway, after four and half years, I was able to settle and get right up to the edge of going to trial where I was able to wrap that up and conclude that and get the IRS paid with some of the settlement dollars and not without an extraordinary amount of like just finagling and working these details. Even the IRS was involved in the settlement because
Amanda Kaufman (11:02)
Holy.
Justin Lund (11:05)
they really wanted to make sure that they got their money. it was it was a tough situation to navigate. But again, coming back to why I feel like that could be useful because I just didn't look command. I never looked at the numbers and people in my life after the fact were like, well duh, if you would have paid a tent, you know, I was like, did I really miss all the signs? Man, I'm a knucklehead. What am I doing? And now?
Amanda Kaufman (11:09)
Mm-hmm.
Justin Lund (11:32)
working with entrepreneurs, they're not often as dumb as I was. Most of them aren't. mean, that's good. But one of the key things that I teach people today is if they're that ignorant, like they just want to kind of head in the sand sort of thing, then I just tell them, OK, 1.0, our first version is you're just going to set a meeting with your CPA every quarter. Once a quarter, you meet with your CPA. something as simple as a simplest framework that we can come up with that gets them on the phone.
Because they have this misconception that I don't know. I'm here. I know nothing about numbers to know something about numbers. I need to be up here. got a huge get up here. They picture a CPA or somebody like a Masters degree with accounting, you know, and all these 10 years of that. No, there's like steps. A lot of them that go from here to there. So by getting that and I still do the same thing. I follow that version 1.0. I talked to my CPA. It's usually it's just like a conversation like this.
So one of those couple of years ago, um, was I was telling him about how I was turning in the lease and the lease was going to be due like to turn in in just a few weeks. It was November, the end of November staff for Thanksgiving. And I was like, you wouldn't believe it, man. My wife's driving this car. We're turning into the end in less than a month and there's an early snow. We hadn't put on the snow tires yet and
She slips a little bit off the road and hits a mailbox and does damage to the front, the side, the side, the side, the back like every part of the $15,000 damage. And he's like, wait, when did you say you're turning it in? So I'm telling him a story just about what happened last week. And he was like, hang on. What? When did you say you got turned in? What are you going to get a new car? I'm like, I don't know, man. I'm just I was just telling you that I'm just frustrated with that. It costs so much money. It's going to be such a huge repair. He's like, could you buy a car before the end of the year?
Is it for your business? And I said, yeah, yeah, yeah. OK, he's like, because accelerated depreciation is still in effect and you can take it all. And he tells me about this. so I bought a $57,000 Ford F-150 and wrote all of it off that year, took my taxable income from the highest bracket to the lowest bracket with all my deductions, including that truck. And if I wouldn't have talked to him, I would have turned the car in on January 10th when it was supposed to be turned in. I would have found a replacement sometime thereafter. And I would have just been with
Amanda Kaufman (13:39)
Wow.
Justin Lund (13:50)
my head in the sand paying lots more money in taxes. So those exchanges, you don't need to know what you're doing. You don't need to have a strategic agenda to talk to your CPA. We could talk just like you and I are talking and they will pull things to have context to your life and your business. That'll make a huge difference.
Amanda Kaufman (14:08)
I love this. you know, I think a lot of shame gets attached to our identity, you know, like maybe I am dumb or maybe I'm not smart enough or I was supposed to already know or, you know, we can assign these identity traits if you will and then say like, well, what does it say about me if I don't know all the rules or what does it say about me if I made a math error or something like that? And I'm like, it's not making it about you. You know, one of my most empowering things I've done as I've built my business is just be dumb as possible.
Justin Lund (14:22)
100 %
Yeah. ⁓
Amanda Kaufman (14:38)
Meaning like when you sit down with a CPA, ask the dumb question, right? That's what they're there for. They are there to know answers. And guess what? If you ask dumb questions and they're like, I don't know, and you're getting a sense of like, wait a second, like they're they're kind of making things up. Like our human ability to perceive other humans is a really powerful tool to find out, like, is somebody trustworthy?
Justin Lund (14:43)
We're sure. We're Yeah.
Amanda Kaufman (15:06)
and credible and able to really lead you through a thing or are they building a huge facade? And you I really appreciate, you know, the story and your candor and everything because I think a lot of business owners, to your point, they have a lot of, I think some of it's cultural, you know, as Americans, very, very independent, you know, I got to do all this all by myself. But again, like kind of worrying about, you know, I'm...
Justin Lund (15:27)
yeah.
Amanda Kaufman (15:32)
I'm doing this because I couldn't hold down a day job. Like, what are you talking about? You know, with these other requirements. But I also think that there's certain skills that good entrepreneurs generally have. And one of those things is knowing your numbers. So it's okay to be intimidated by that. And like another one would probably be being influential and being able to have great personal relationships and things like that. And every one of us has to learn
Justin Lund (15:55)
Mm-hmm.
Amanda Kaufman (15:59)
skills and especially if we've never had exposure to those skills in the past. So you can make it a matter of identity that's like a fixed mindset. I'm never going to change. Nothing's going to be different. Or you can do what you've done and just like grab those experiences and say, wait, the cost of not knowing, right? What is the cost of not knowing? That's real high. So what if I let myself
Justin Lund (16:11)
Hmm.
Amanda Kaufman (16:25)
start to learn and what if I let myself really own my knowledge and lack of knowledge so that I'm empowered to really make some change here? Yeah.
Justin Lund (16:29)
for sure.
Yeah, and I would say,
you I don't know that I...
embody this, these traits that you're so kindly speaking of, but I they've been done to me and it's been a forcing function upon me. Like, and I would say you don't have to do it that way. You can do it. What Amanda's saying. That's, that's a better way to just work on the flexible growth mindset aspect of it. And as you were speaking, it reminded me of a young woman that I was talking to just starting a business. She's, and I gave her this, this prescription, like talk to your CPA four times. She didn't have a CPA. And so I gave her some advice on here's how you
can go look for one. I followed up with her a couple weeks later and she said, yeah, I don't know. I don't think that's for me. I'm like, oh no. What do you mean? She said, well, they're like 250, 300 bucks an hour. And they're just like, I think they're kind of talking down to me. And be like, little girl, you don't know what you're doing. I'm like, all right, cut the shit. Hold on. We got to stop that right there. Okay. And first of all, you didn't follow what I said to do. And second of all, how much did you pay in taxes last year?
She said, well, like, what do you mean? said, how many dollars were withheld and or total amount paid to the state and the federal governments combined? She said $97,000. And I said, you are telling me that you don't want to pay 300 bucks an hour four times a year if you could cut that in half. I mean, don't be stupid with your. And it was what you just said, Amanda. She just didn't want to feel dumb.
She don't want to feel, but she'll pay 97,000 bucks to not feel that feeling. Like, oh, that breaks my heart. hurts. It actually hurts me. Yeah. Yes.
Amanda Kaufman (18:10)
That is an expensive fee for not working
on our influence. And the other thing too is like with things like accountants, lawyers, experts, real pros, to your point, like, yeah, their fee is high, but they went to school forever. They've practiced, they've earned their fee when they charge that fee. And the thing is, is that if you get heebie-jeebies and like big shout out, especially to the female entrepreneurs who kind of...
Justin Lund (18:27)
Mm-hmm.
Amanda Kaufman (18:40)
don't want to be made to feel even worse, you know, of ⁓ like, you're not good with math. you're not good with this. And men too, right? Like, don't let someone else have that power over you. I don't care how much money they make. I don't care what their degrees behind their heads say. If they're a jerk, they're a jerk. And there's a lot more people out there who are kindhearted, who have great souls, who care about the success of their clients. You know, I actually,
Justin Lund (18:43)
Mm-hmm. Yeah. Yeah, yeah, yeah.
Amanda Kaufman (19:10)
You'd be so surprised. And I'm sure you know this, but saying saying out loud for the sake of the podcast that like I had a question and I called around to a few lawyers. I got my question answered by a high, like a high ranking lawyer, a well-to-do lawyer. And he was like, I'm going to talk to you like you're my little sister. And here's what I would say. And and the thing is, at the end the at the end of the day, he wasn't the right person to help.
Justin Lund (19:27)
You
Amanda Kaufman (19:34)
for the thing and, and it actually prevented me from making a very costly decision and he didn't charge me a single penny. And, and the thing is, is the good ones, they know that when you, when they serve like that, that you're going to be the referral source. You're going to tell the story. Like I'm talking about it on my podcast, like right now. And, and you know what I mean? So never settle for a butt head ever. Yeah.
Justin Lund (19:39)
Mm-hmm. Mm-hmm. Yeah.
Yeah.
Right. Yeah.
For sure. But you're touching on something
that's important, I think, to bring up because as entrepreneurs, you remember that old TV show, MacGyver? that you ever seen anything? OK, the guy could fix anything with a piece of bubble gum, duct tape and a ballpoint pen. Right. So as entrepreneurs, we have similar traits where we look at everything through this lens of, OK, how can I solve that? What can I
Amanda Kaufman (20:04)
Mm-hmm.
Justin Lund (20:18)
Give me one of those. I'm going to put an act out. I'll just get up an hour earlier. OK, I got this. No big deal. So that can color your choices when you start looking at professionals like this. OK, you may talk to a butt head like you just described, but because you like to put lipstick on pigs and solve problems, you and that's just a trait that.
the world needs more of, but you need to know yourself too. It's something I learned in rehab, right? Know thyself and to thyself be true. So the way to offset, I've got a simple playbook for this that just cuts through that noise that taps into the energy of who you need to work with, like you just described. And the simple version is you call 10. Like don't stop. A six is the minimum. Don't.
And it's not six phone calls that you make. It's six conversations because every lawyer, every CPA will give you 30 to 60 minutes as an initial consult. That's kind of like their sales pitch. And if you compare one to another, to another, to another six times, you will know for sure who you want to work with. But if you call one and I did this when I started all my legal problems, I started with a lawyer, I got a recommendation. I called them. I was six months into it before I realized
This is terrible. This is not at all what I need or who I need. And that's how I began to learn how to bring
real skit because I'm not a lawyer. So how am I going to interview a lawyer? How am going to interview an accountant? I can barely add two plus two. So what am I? So those are the limiting beliefs that are below the surface. So that when I call a lawyer like this young lady I mentioned, she's calling an accountant and she's got these limiting beliefs and tries to ask a few questions. Anything is easily perceived as
Amanda Kaufman (21:52)
Mm-hmm.
Justin Lund (22:05)
You are foolish. You must be dumb. And so up comes the limiting beliefs. Down goes the phone. And we're like, yeah, I'm OK. I think I'm OK. I'll pay the $97,000 in taxes. It's ridiculous. All you need to make is 10 more contacts. Talk to 10 lawyers and see what. And you'll find a lawyer, just like you said, because there are plenty of. There's a few bad apples out there. I've dealt with them.
But more of them than not are good apples and they will help you. They want to support and serve you and they realize, yeah, I'm not going to try to nickel and dime this lady for this because she may need me in the, you know, like that's just good karma. And most of them are like that. Yeah. Yes.
Amanda Kaufman (22:42)
That's it. That's it. Be a pro, right? Like look for pros and be a pro and professionals call
around. I love that so much. So Justin, what's the best way for people to follow you, to connect with you after this episode?
Justin Lund (22:56)
yeah, probably Instagram is I'm on all kind of the platforms. I think it's the same username everywhere. It's it's Justin Lund. So yeah, I'd love to love to connect with you there. And if you are, if any of this stuff resonates, I do have that playbook that I'd be happy to share. So if you just send me a DM there, professional Amanda and that will get I'll just send it to it's a Google Doc. You don't have to opt in or log in or give me any of your blood samples or anything. Just I'll send you the Google Doc that I use.
Amanda Kaufman (23:22)
No DNA
required.
Justin Lund (23:24)
Yeah, that my team uses. We all use the same thing like we needed a different little specialty work with an accountant on one of our clients that has a special pension plan and we're like, well, this is way outside of our scope. So we just pulled out the playbook and she sat down and went through the calls and I mean it just it just works. It's simple, straightforward, but it works to get your results. So if that is something that anybody out there needs, I'm happy to share. No problem.
Amanda Kaufman (23:51)
I love it. And listener, we'll make sure to have Justin's links below so that you can very easily find those and give him a follow. And hey, if you love this episode, make sure you smash that subscribe button before you move on. And if you found this conversation helpful.
enlightening, encouraging, motivating, disillusioning, whatever it was for you, grab the link and share it with three of your friends. know, can text it over to them, send it over a DM, however you guys normally communicate. Just grab the link to the episode and send it on over so that they can have a listen. And hey, if it really did make a big difference, the biggest difference you can make back to us is a review. So if you leave us a honest review on wherever you're listening to, it'll help other people decide whether they want to listen.
to the Amanda Kaufman show. We're gonna be back with another episode very soon, but until then, make sure you do what matters.
