459 Mark Herschberg

[00:00:00]

Jeffrey Feldberg: What if the skills that truly determine your success? Were never taught in school, but were the very ones that shaped every major turning point in your life. Mark Hirschberg isn't just a career strategist, he's a code switching visionary who's thrived as a cybersecurity expert. Startup, CTO and MIT instructor.

He's navigated boardrooms and server rooms with equal fluency, and along the way, uncovered a hidden truth. Technical skills may get you in the door, but it's leadership, networking, and strategic thinking that carry you to the top. Mark is a bestselling author of the Career Toolkit, essential Skills for Success that No One Taught You a book.

Born from two decades of teaching at MIT's acclaimed. Career Success Accelerator program. But what makes Mark stand out isn't just his resume, it's his mission. He's taken lessons forged in the startup trenches, honed in the Ivy League, and pressure tested in Fortune 500 companies, [00:01:00] and turned them into practical tools that help professionals build reMarkable careers.

On their own terms, whether you're pivoting, scaling, or searching for purpose, Mark's, insights illuminate the blind spots. Most leaders don't even know they have. This is more than a conversation. It's a recalibration of how we think about success. 

And before we hop into the podcast, a quick word from our sponsor, Deep Wealth and the Deep Wealth Mastery Program. We have William, a graduate of Deep Both Mastery, and he says, I didn't have the time for Deep Both Mastery, but I made the time and I'm glad I did.

What I learned goes far beyond any other executive program or coach I've ever experienced. Or how about Bruce? Bruce says, before Deep Wealth Mastery, the challenge I had with most business programs, coaches, or blogs was that they were one dimensional. Through Deep Wealth Mastery, I'm part of a richer community of other successful business owners.

The idea shared forever changed the trajectory of the business and best of all, the experience was fun. And we'll round things out with [00:02:00] Stacey. 

Stacey said, I wish I had access to the Deep Wealth Mastery before my liquidity event, as it would have been extremely helpful. Deep Wealth Mastery exceeded my expectations in terms of content and quality.

And you know what, my Deep Wealth Nation, why they're saying this is because Deep Wealth Mastery, it's the only system based on a nine figure deal. That was my deal. And as you know, I said no to a seven figure offer, and I created a system that we now call Deep Wealth Mastery that helped myself and my business partners, welcome from a different buyer, a different offer, a nine figure exit.

So if you're interested in growing your profits, preparing for a future liquidity event, if that's two years away or 20 years away, and you want to optimize your post exit life, Deep Wealth Mastery is for you. Please email success at deepwealth. com. Again, that's success, S U C C E S S, at deepwealth. com. We'll send you all the information about Deep Wealth Mastery, otherwise known as Scale for Ultimate Sale. That's where you want to be. You want to be with other successful business owners, entrepreneurs, and founders just like [00:03:00] you who are looking to create market disruptions.

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Welcome to another episode of the Deep Wealth Podcast. Well, Deep Wealth Nation, let me ask you a question when it comes to where you are in terms of your business, your success, either from a technology side of things, or from leadership, from networking, taking your game, your team's game to the next level.

Where are you on that? Are there some gaps? And I suspect you're saying, yeah, Jeffrey, there's some gaps in those areas. What can I do? Stop your search. You've come to the right place. We have a very special guest in the House of Deep Wealth today. Mark, welcome to the Deep Wealth Podcast. An absolute pleasure to have you with us.

You're a fellow entrepreneur, a thought leader, an author, a speaker, an advisor. You're doing all these things, which you're gonna talk about. But that said, there's always a story behind the story. Mark, what got you from where you were to where you are today?

Mark Herschberg: I have a very interesting [00:04:00] dual career. I came out of MIT back during the.com era. And start as a software developer, I realized I wanted to become a CTO. A Chief Technology Officer. And I've achieved that goal. These days work as a CTO, often a fractional CTO, where I help multiple companies as an Advisor or part-time as a CTO to help them really get to next level or turn things around.

And so there's a lot of technology work I do there. But in that journey, where I realized early on was to become a CTO. It wasn't just about being a great engineer. That was certainly important, but to be that type of leader, I need to develop a number of other skills that we don't typically teach in college.

Leadership, networking, negotiation, team building, hiring, all these skills. We've heard them. People tell us they're important, but no one stops to teach us. I said, well, I have to figure this out now. We didn't have great podcasts like this one. [00:05:00] Back then. I was kind of on my own. It was a lot of reading books and trying to find mentors.

And along my journey I realized these skills are not just for C-level people. We want everyone in our organizations to have these skills, to be leaders, to be good at networking, at negotiating. And so I began to upskill my team. As I was doing that, MIT got similar feedback. Companies were saying, when we hire, we have challenges finding these skills, not just with new college grads, not just with your students in general.

And we heard that and said, we need to incorporate this into our education. As MIT was doing that, I said, I found the same problem. I began to upskill my team as I was learning myself. I was creating training programs for my team. Said, maybe I can help you out. Here's some content. Maybe this will be useful.

I said, great, thanks. But before you go, please stay and help us develop more content. So I spent a few months working with them, developing more training. Said, [00:06:00] fantastic, but before you go, can you actually stay and help us teach? And so now, in addition to all my experience building startups from classic startups to helping Fortune five hundreds play startup and launch billion dollar startups, I have also been teaching at MIT for over 20 years, coming up on 25 now, teaching our students at MIT as well as at other universities.

And now in my corporate speaking and training. How to develop these critical skills that we never teach people.

Jeffrey Feldberg: Wow, Mark, that's quite the story. There's a lot to unpack there. So before we get going, I'm just curious with what you're doing, and I guess it'll be a stereotype that I'm gonna put out there when. I think of, or at least in my experience, when I think of technology people, I don't necessarily put them out there in terms of some of the leadership things that you're doing and finding the gaps and being able to help people fulfill that and helping to become a better leader.

So where is that coming from? Because that's very unique, at least from my perspective and in my [00:07:00] experience.

Mark Herschberg: I'm going to share an analogy. I learned this from my friend Charles Verson, who I teach with at MIT. We're gonna do a little bit of math here in this analogy, but don't worry, it'll be very easy. Imagine you have a rectangle. That is four by 10, and you need to increase one of the sides by two units to maximize the area.

Which side do you increase? And feel free to pause the podcast a moment if you need to. The answer of course is we go from four to six to get 60. The other way is 48. Okay? There's some middle school math. Conceptually, what are we doing? We're taking those two extra units on that short side and we're amplifying them.

By the long side, by the 10. Now, if you think about what this means in terms of our capabilities, we all have long sides and short sides, often more than two. And for many people, we have a very long side. That might be our domain. In accounting, in sales, in technology, whatever it is, we're extremely [00:08:00] long and we have to keep up with that.

Certainly in technology, I have to constantly learn new technologies or I become a dinosaur, so we're making that long side longer. But if you've got a very long side and your other sides are really short. You are relatively small in terms of area, in terms of your overall capability. In fact, by working on the short sides for the per unit of effort, the ROI on that development, we get a much better return.

 And now let's think about this practically. You've probably all met technologists who you presume are brilliant, but you can't tell because they just throw around all these buzzwords and they're so technical and you can't follow them. And they might be brilliant, but they can't communicate ideas effectively.

So by helping them to be a little more effective as a communicator, we're not saying they're ready to go on that TED talk stage and deliver a world class talk. We're just saying they communicate. More effectively. Now, that long side becomes more useful, and this is true for all of [00:09:00] us. Maybe you're great at understanding your industry and how to drive your business, but you're not such a good leader.

Or maybe you're not great at networking. And so again, by working on these short sides, by getting a little bit better, we become far more capable overall. And I recognized early on I needed to be capable in multiple areas to really be effective at what I wanted to do.

Jeffrey Feldberg: Well firstly from you being the math guy, to me not being the math guy, I've always been more the Marketing guy and definitely not on the math side. I thank you for explaining that math and being very graceful for me on that. And by the way, Deep Wealth Nation, please go to the show notes because in the show notes we're gonna have all the information, but there's gonna be a link to Mark's book, the Career Toolkit and I love the subtitle, Essential Skills for Success That No One Taught You. And what I love about the book, which we'll talk about, Deep Wealth Nation, this is from a fellow entrepreneur. You heard Mark in startups and technology, and when you had the.com boom, he's been there, done that. He's [00:10:00] been on this journey.

He can save you a few hiccups along the way. Pick up the book, go through that. There are some incredible strategies that are in there. And before we get to that, Mark, let me ask you a question, because when it comes to people and the short side, the long side, as you've been talking about, there's one school of thought that said, okay, take.

A particular person, Jeffrey, myself, play to Jeffrey's strengths, have him forget about his weaknesses, find other team members or automate that or other things that will do what Jeffrey simply can't do, and have what he's good at. Have him become great at that. So where does that fall with your system?

How would that work? Mark?

Mark Herschberg: There's that classic question, should people be eyes very long and deep versus tease where they get a little more broad at the top? And that analogy has been. Really twisted and tortured. We see people talk about ES and M'S and dashes and every possible letter. People seem to have an analogy here, but again, I use that rectangle analogy.

Let's suppose you are really deep in [00:11:00] area well, getting better at networking, and that's a skill I universally hear from people. I wish I was better at networking. Now, networking doesn't mean collecting lots of business cards. Networking is about relationship building. It's a very different mindset when you improve your ability to network.

A few things happen if you are looking for new jobs in the future, certainly you do get more opportunities, but also if you are looking for customers for partners. For suppliers, you get more access to opportunity and better opportunities. If your entire organization is better at networking, they are bringing in as well.

We often think, well, of course, as the CEO, as the founder, I need to do this. But do I need my team to do it? And the answer is yes, but it's not even directly for deal making. By having stronger networks, you hear about other opportunities and challenges. Ai, for example, is disrupting all of our [00:12:00] businesses.

Wouldn't it be great if you had someone in your network who is an expert or realistically. Two or three or half a dozen people because honestly, we're all doing our best guesses about what's going to happen, and it's really hard. So I wouldn't just take one opinion. If you've got a strong, extensive network, a diverse network that can bring you ideas from other areas, that can bring your whole organization, because everyone has now been trained in networking now you can be much more effective and have a lot more opportunity coming to you. So all of these skills, by developing them, we become more effective.

Jeffrey Feldberg: Okay, got that in. So lemme ask you this because as you're talking about networking in my books, networking would be, and I'm using air quotes. It would be a soft skill. It doesn't show up in a balance sheet or in a profit and laws, and in fact, some people would even dismiss that. Particularly with your background on technology.

I love hearing you talk about that. And in fact, we talk about this in the Deep Wealth nine-step roadmap in our [00:13:00] flagship program. A shameless plug here, the 90 day Deep Wealth mastery program. Same system, I use to say no to seven figures and to later, less than two years later, walk out with a nine-figure Exit deal in step two X-Factors.

It's what differentiates one company from the competition, and a lot of times it's soft skills that's showing up. So with that in mind, Mark, when it comes to soft skills, are there any other soft skills at once upon a time, perhaps you would simply have dismissed, but you've now come to realize later on that hey, yeah, that soft skill there, that's really a game changer not to be ignored.

Mark Herschberg: and you're right, these are soft skills. First, before I address the question, lemme just talk about why this is becoming more important. We are recording this in the summer of 2025. AI is really starting to permeate across a lot of different industries now. It's still nascent, it's not completely replacing us, but it is starting to take more and more of our work and hiring someone who knows how [00:14:00] to create pivot tables in Excel.

That's less important because even if you don't know how to create a pivot table, AI can soon do it for you. It can start to do financial analysis. It can start to do coding. And I'm not saying here in 2025, you don't need software developers, you don't need people doing your financial analysis. But as it gets more powerful, that differentiator of having better people starts to go away.

And so it's these softer skills that are really going to give you the edge. It's having that more extensive network so you can find the customers sooner. You can find the opportunities and partnerships before other people do. So let's talk about some of the other skills I. Communication is key, especially as AI starts to put out a lot more content for us.

We need to learn to be more effective in our communication, more succinct, and being able to communicate effectively to a specific audience. Communication's really key. [00:15:00] It's not just having the right answer, it's being able to communicate that answer effectively to the people who need to buy into it.

Likewise leadership, and that doesn't mean you have a fancy title. That means you see an opportunity, anyone, any level of an organization, and you get buy-in for it. You convince other people to go in that direction. If you don't have good leaders, even when they have good ideas, you're not going to execute on because people won't buy into it.

And then finally negotiation. Now, this trips up a lot of people because negotiation people say, oh, I don't wanna teach my team to negotiate. Maybe the salespeople, but boy, if they learn to negotiate, imagine every employee is going to come to me and demand a higher raise, and that's taking a very fixed mindset.

Imagine if everyone in your organization got even just two, 3% better at negotiating. Well, first, every contract you have. Customer contract, vendor contract partnership, two 3% better. All of a [00:16:00] sudden your bottom line is better. You've got the money for raises, but in fact, there's a lot more going on, a lot more negotiations that happen.

In fact, most negotiations we do are with our coworkers, with people inside the company. It's not about money. It's about, ah, I don't wanna do the boring part of this, and neither do you. How do we work together? Okay, well I'll do this part, and you do that part. Or how do we think about your team and my team are both competing for the same resources.

How can we get along and not butt heads and then dislike each other later and learn to be more effective in those negotiations? Makes your whole team more effective. If you can get every negotiation to be a little bit better, that two or 3% raise that they might be able to negotiate for at the end of the year.

That's peanuts compared to how well your company is doing. So all of these skills and some others we can get into as well, really do impact your bottom line in a positive way.

Jeffrey Feldberg: Absolutely am my goodness so much there. And Deep Wealth [00:17:00] Nation, there is a method to the madness. We're gonna go a little bit off script here because I did have AI for a little bit later on, but you brought it up and it's a terrific segue. So why don't we talk about that? Because Mark, you're right. As we sit here and we're seeing what artificial intelligence, ai.

What it's doing and where it's going. My goodness. Life as we know it continues to change. The headlines by the day are coming out and by the time this episode comes out, it'll probably be obsolete in some of the things that we're talking about with where AI is and what it's doing. But it's been interesting because when AI first came out, just like when the web first came out, I'm dating myself.

It was very utopian. All the web, it's gonna change the world and it's gonna be roses and poppies everywhere. And in some ways it is, but there's always a dark side to. Just being human in what we do. And we saw some of the dark sides with the internet. And when AI first came out, oh, there's gonna be no job loss.

This is just gonna make everyone better, more efficient. And now we're starting to see headlines of, oh, massive job layoffs and job loss is coming down the pike. But [00:18:00] headlines aside, high Syria aside with that. Where we are today versus where you think we're gonna be. And I know it's anyone's guess, and it's not really a fair question to ask you this, but you're right there as CTO and you're hobnobbing with yourself and some of the best minds that are out there.

What's your take on AI above and beyond what you've already shared of, hey, get the softer skills at AI doesn't have at this point. To help distinguish yourself out there, what do you want us to know about ai?

Mark Herschberg: So here again, my take in the summer of 2025, I put the data in just because you do need to think about when is he saying this? Three years from now, you gotta say, this guy's totally off. Well, it's a prediction. There's a couple different outcomes. There's no one, this is exactly how it's going to be. So when we look at certain areas, let's take legal and we hear, oh, this is going to make legal work so much better.

One of the challenges we have is with the hallucinations.

You can't get a 95% solution in legal, you can't have it. Well, [00:19:00] it got 95% of the contract, right? But boy, it missed a key term. This happens in the contracts. My company has not acceptable. You still need a hundred percent of your legal team to review everything and make sure it's a hundred percent buttoned up.

So we can gain some efficiency. Sure. For drafting certain motions. It's gonna be a little better, but it's not going to be necessarily a replacement unless we can get rid of those hallucinations. Now in other areas like customer support, I. 95% is great. If you could handle 95% of your questions. With ai, you just saved yourself 95%, right?

You got huge efficiency gains. So it's going to vary a little from the particular discipline. In a lot of disciplines, we will see efficiency gains, and then it's a question of how much impact. There's something called Jevons Paradox in the mid 19th century as engines got [00:20:00] more efficient, you might first think, well, engines more efficient, we need less coal.

But the opposite happened. People said, it's more efficient. It's cheaper to create and use an engine, so I'm going to use in newer places. And coal production went up. We needed more coal for the new engines we saw with software. If you think back to the 1990s, the.com era, we are easily 20 to 30 times more productive today.

This is because of advances in software languages and frameworks, open source tools. Non open source tools. The fact that I can go to AWS or other clouds and spam a server in minutes and not weeks. Everything's cheaper and faster, but demand has gone up. People said, great, that 20 million project is now 2 million.

Now it's cost effective to do we saw an increase in demand. There may be limits in certain areas. Right now, talking to my peers in the summer of 2025, we're seeing ballpark a 25% efficiency [00:21:00] improvement from generative AI in software coding. Your mileage will vary a lot depending on the nature of your software.

From 0% to far more than 25%. If it's just 25%, vin's Paradox probably still applies that great. We'll just keep creating more software. We're not gonna lose a lot of software jobs. If it improves and we get to a hundred percent, 200% maybe, then we start to see software jobs disappear. And now in the past we've talked about the creative destruction of capitalism.

We destroy jobs, we create jobs. What's happened in the past is that destruction has taken place over years, possibly decades. It's either been very concentrated. So elevator operators, we got rid of most of them over about 10 years, but they were very small farmers. We got rid of most of them, but over a hundred year period.

So there was time to adjust the threat here, and I've written a lot about this and when we talk about the website later, you can see my writings and [00:22:00] other resources. The threat here is that we're going to eliminate millions. Tens of millions of jobs systemically eliminated over a very brief time period on the order of about five years.

And we're not going to have enough time to retrain and adjust those people, even more so because when you eliminated some of those blue collar jobs, someone who was a toll booth collector, they can become a Walmart greeter. But someone who was a software developer, a lawyer, an accountant, they've put a lot of time and effort into their.

Profession, it may not be so easy to switch them to a new one. And I'm worried that we're gonna see systemic unemployment for a number of years. And societally we are not set up to help those people transition. This is gonna cause a lot of societal problems that I think we really need to face, and no one's talking about.

Jeffrey Feldberg: Interesting. And so as you're talking about that, I've heard the counter to that, all kinds of [00:23:00] jobs have been created that didn't exist five years ago. We didn't have titles for them.

And yes, there'll be a large displacement because of ai. At the same time though, new opportunities, new positions will be coming up and the argument goes on to say, and do we really think it's the best use of our abilities to be driving people point A to point B, where if that were automated, we took the human element out of it.

We can be having people work in much more fulfilling kinds of jobs that don't exist yet. We don't know what they are, we don't even have the titles for them, but they're on the way they're coming. What would you say to that fact or fiction?

Mark Herschberg: Long term, 10 to 20 years out. Yes, new jobs will come up. And we will find new demand, new things we haven't thought of that will employ the people. My concern is that there's a gap that the number of jobs that get destroyed will be destroyed. Those people will be unemployed for a number of years before the new jobs start.

So the counter example at you are giving, let's think about [00:24:00] online advertising. The number of people who are doing advertising. For TV and radio was declining, but then the number of people doing online advertising. Online and layer of social media increased. And so we saw a decrease in one area and offset in the other.

And so yes, for any individual, it may have been a tough transition, but we could see that new jobs were being created roughly around the same time that the old jobs were being destroyed. The risk that I see with AI is we're gonna destroy the job so quickly. There's gonna be a period of a number of years before the new jobs really come up and get created, and it might only be three or four years, but imagine if you've got 15% national unemployment for three or four years, that can really put the economy into a tailspin.

Jeffrey Feldberg: What I'm hearing you say, yes. New opportunities, new jobs are gonna be here, but it's the gap of how long it's gonna take for them to come [00:25:00] on stream, even if it's faster than it has been in other kinds of disruptions, there's still gonna be a gap, and that's the issue.

Mark Herschberg: That's my main concern, and I think we need to. As a society, think about how we change education and employment, including secondary things like healthcare to be able to help people transition through this. I had spent some time working in a program for New York's Economic Development Council. Back around 2009, 2010, where we saw during the Great Recession, New York said, we've lost a number of jobs and we know they're not coming back.

This isn't a normal recession where just wait for things to turn around and then they get jobs again. Their jobs are gone. And so we proactively work to transition people into new careers because the sooner we can get them back into a new job, the less they took from. Societal resources like unemployment and the faster they could start contributing, paying taxes on their income and purchasing again and helping in a net positive way.

[00:26:00] We need things like that at a national level.

Jeffrey Feldberg: Okay. And so Mark, as we're talking about, this is actually a terrific segue now for your book, the Career Toolkit, because really what I'm hearing you say is massive disruption. It's ahead for us and what I love about the Career Toolkit, yes, I can apply it to me as an employee. I. At the same time though, I can also apply to me as an entrepreneur because really it's one in the same thing.

And coming outta this conversation, Mark one thing loud and clear. I'm hearing you say, Hey Jeffrey, with AI now on the scene, you've gotta become so good. That people can't forget you. They can't ignore you because you stand out above all of the noise. And the Deep Wealth Nation may be saying, okay, yeah, I hear you.

I agree with that, but what do I do? Where do I start? And so this is where we turn to the Career Toolkit, whether I'm, again, a team member, an employee or an entrepreneur, a founder, starting a new company, or looking to create a Market disruption with a new service or a new product, or a new offering. As we look at the Career Toolkit, let's take a step back for just a moment.

Very high level, if I were [00:27:00] to come to you, okay, Mark. Yeah, become my CTO, but at the same time, be my company's Advisor to help on the leadership side to help me train the team. Let's roll back the curtain. What's your secret sauce here, Mark? What's going on in terms of your process, in terms of what's going on?

How long does it take? What can I expect to get with the proviso? Every company's different. I get that. Every company's on its own journey. I get that as well. This is big picture back of the envelope.

Mark Herschberg: What I'm going to briefly describe here, you can download for free from my website, which will give you at the end of the episode. Download completely free. I'm not here to sell you, oh, buy my process. You can download this and do it yourself. I don't even ask for your email because I'm not trying to sell you anything.

You can easily create an internal training program. Now, certainly if you want, you can bring in people like myself who are experts. We come into speakers, we have workshops, we can do training, and you are more than welcome to do that. But if you're saying, well, money's tight. I want to do [00:28:00] something more sustaining, not just a one and done.

You can download the Career Toolkit Professional Development Program. What you're going to do is internal to your company. You can create peer learning groups. These are groups I typically recommend somewhere around six to eight people, but there's ways, if you wanna do larger groups or smaller groups, and you put them together and you provide them content.

Now, yes, you can use my book for content. You can use other books. You can use free resources. Episodes from great podcasts like this one or articles or videos online, and you have the group watch the video, read part of the book, whatever the assignment is for that period. Periods are usually about two or four weeks, so you're gonna meet maybe every other week or once a month, and then you discuss it.

You have that discussion as a group. And here's why this works. If you think about sports, I can't just say, Hey, I'm gonna turn you into a great basketball player. Here's the [00:29:00] rules. Oh, and remember, you should shoot three pointers in this case, not that case. And here's what you need to know to be good.

Fantastic. You're done. Go play. That's not how we learn sports. You need to have drills. You need to have scrimmage, you need to have coaching. You need to watch the tape. When you have these peer groups, what you're doing, you're reading some content, so that's the training. That's like the drills, because you can talk about, here's a leadership situation, here's a negotiation situation.

This, by the way, is how top business schools do it. They do the case studies, they do the analysis and discussion, but you can do that yourself. And so that's giving you the drills and then people are going to bring in different perspectives. Hey, at my last company I had a kind of similar leadership challenge, and here's how it worked and here's what worked and here's what didn't.

And this is how you learn. That's like scrimmage, because what you can't do is I can't go to my team and say, oh, I'm gonna try leading differently. And then if it doesn't work, oh yeah, time out doesn't count. Forget [00:30:00] it, do over. We don't have that practice time, but this group gives you that chance to practice.

And you get two other benefits by the way. One is that you're gonna create a common language in your organization. If you choose a book, for example, good to great. When everyone's read that, you can say, let's use the hedgehog strategy or the Fox strategy, and everyone knows exactly what you mean because you all have the same tools and analogies, and most importantly, you're going to foster internal networking because the groups you create should be from different parts of your organization.

Don't put all your engineers in one group and all your salespeople in another. You want that diversity of perspective, and these are people who often don't talk to each other, so that's gonna create a fantastic way for people to get to know each other. If by the way, you are a very small organization, I'm only five people, go find other small orgs.

You are probably part of peer groups, maybe through Deep Wealth Nation, maybe through others. You say, [00:31:00] Hey, I've got five people. You've got five people. She's got five people. Let's have different people come together and talk and just give those different perspectives so you're not all in the same company where it could be a little awkward if you're that small and you don't wanna be in the same group with your boss.

Jeffrey Feldberg: Now it's interesting, Mark, and I completely agree. What I'm hearing you say is it is not enough to hear it or even take some notes about this, or I'm typing it out to put it away in whatever digital collection that I have. I've gotta go from the student. To the teacher, to the master, because if I can teach it, then I know it.

And you're right. How many times in an organization, even if they have a reading book club where they're all reading through it, are we really implementing that? Are we really putting that into the culture? And to that end, you created an app, the Brain Bump. And so with the Brain Bump app, why don't you share with Deep Wealth Nation, and I love what you've done, but why don't you share with them as a creator, what is the brain bump, what's it all about, and Why would I want the brain bump to be embedded, not just with myself, but my entire team [00:32:00] as an app, as a strategy?

Mark Herschberg: It addresses the challenge you brought up that you can't just read it once. Forget about it because where we read information isn't where we need information. And so the Brain Bump app, which is completely free for Android and iPhone, it takes the key ideas, not just from my book, but from scores of other books, podcasts, blogs, all these different sources.

They're in the app, they're in the pocket with you, and so you'll use it one of two ways. Perhaps you're trying to be a better leader. What? You can't just read it once and say, I hope I remember it. We know that doesn't work. We know you need to be exposed to it multiple times. This is why we had flashcards as a kid, but as adults, we're not gonna sit there and go through a flashcard app.

There's no test. The Brain Bump app basically takes these key ideas. So imagine from a book like mine, someone highlighted the key points, they're all already in there for you, and then you say, I want to get that [00:33:00] leadership tip. Right At 9:00 AM because that's my walk into the office. Then I want to get a strategy tip.

Every Wednesday at 2:50 PM because I have a strategy meeting Wednesday at 3:00 PM and so what it does, it delivers the relevant content when and where you need it. So it's exactly when you need to be thinking about, and you get the reminder when it's relevant, not just in the middle of the day where I'm running between meetings.

Yeah, that's a good point. But not now. Not now. It's always timely and relevant. You can also use it in on demand fashion. So at first fashion, I think of it like. A daily affirmation. You decide what type of content and when that content's relevant, so you get it at the right time and place. The second is on demand.

So imagine you're walking into a conference, you're thinking, oh, I read Mark's book on networking, and there are all those tips. I wish I could remember them. You're not gonna carry my book with you, but they're all in the app and they are tagged by category, think like [00:34:00] hashtags. So as you're about to walk onto the conference floor, you open the app and you tap networking.

You filter all the tips by networking. Boom. There's all the networking tips right there. You flip through it, go. Okay, right? Yes. Okay, good. Yep. Got it. And now you're ready to hit the floor. So whether you use the tags, whether you create your own favorites list so you get what you need when you need it, you always get relevant content and that helps reinforce it and helps you apply it.

And Brain Bump is a hundred percent free.

Jeffrey Feldberg: What I love about brain bump, in addition to the price is right. Right now in my own digital library, sure I have all the strategies, but I'm not remembering, oh, Jeffrey. One year ago you took this note about this book that you read or this podcast that you listened to, but with Brain Bump, I can have it as you say, okay, Jeffrey, remember this, or go, back to this, or, I'm gonna do a quick filter on that.

It just makes it so effortless and so easy. It's really one of the few apps that has the technology. Work for us instead of the other [00:35:00] way around, which is typically what we tend to find out there. And I just love how you've put that out there and embedded it into how we can just take our leadership game to the next level.

And so thank you for doing that.

Mark Herschberg: You hit the nail on the head there. 'cause I had the same problem. I'd read something, I'd take notes, I'd forget it. There's a lot of great note taking apps out there. It's the retrieval and that is the key. And please keep using your note taking app. Apps, and you don't have to use brain bump, but whatever note taking you're doing, make sure you have a way to regularly access it because that's where most people fall down.

Jeffrey Feldberg: Exactly. Again, all the best strategies in the world unless you execute them, unless you master them. They're not worth the paper they're written on or the space that they're taking up in the cloud or wherever the strategies may be. So couldn't agree more with that. And Mark, as you're helping out there, either as a CTO or an Advisor to companies, let's face it, as entrepreneurs, the glass is usually half [00:36:00] full to our own expense, and oftentimes we call them inflection points.

Other people call them blind spots. We just don't see it. And by the time we do see it, it's too little, too late. And so again, the question I'm asking is not a fair question because every founder, every company is on a unique journey. No, to our alike, but is it perhaps like a Frito's law? The 80 20 principle where 20% of these actions either done or not done, are creating 80%.

Some people call them problems. I call them opportunities that companies can perhaps struggle over that they don't have to any. Oddly speaking, patterns that you're seeing out there.

Mark Herschberg: A number of them, we see some common ones. Scaling is a big one because what works for your first million dollars has to change for your next 10 million, which needs to change for your next a hundred million and. Whether it's money or team size or product diversity, there are what I call inflection points in that area where you need to change.

'cause your [00:37:00] behaviors on one side are different from the other. We know there's challenges, funding, and that's going to really vary by macro economic conditions and your industry. But still, it's the same process with some adjustments. It's like driving. Driving is driving. Driving through snow is different than driving off road.

Different than driving on a sunny, nice pavement, but it's still driving. There are going to be challenges with technology, and AI is the big one right now. Generative ai, but all sorts of technologies and other technologies are still disrupting industries. And then of course, macroeconomic changes again, summer of 2020.

We're looking at issues with trade and disruptions in supply chain, so we can see these over and over. These have happened in the past. They will happen in the future. Yes, they're going to be a little unique this time versus the other times I. The important thing about any of these is they have been solved by other people.

And to your point, you can [00:38:00] get 80% of the solution by talking to someone who's been there. And that's why listening to podcasts like this where you'll hear from experts, is fantastic. 'cause that's going to give you insights. As well as having these one-on-one conversations as well as having that network.

And again, I wanna emphasize with your network, don't just say, well, I'm in the medical field, I only want to talk to people in the medical field. Certainly have a good portion of your network in your field, but you might meet someone in manufacturing, in SaaS, in customer service, and they've been through fundraising, they've been through scaling, they've been through other challenges.

And their solution, you might say, oh, it's a little different for me, but I can take that key idea. I can take that 80% and apply it. So really go out and source lots of ideas through this podcast, through your network, through other resources.

Jeffrey Feldberg: And as you're talking about that, I'm going back to the entrepreneurial journey because as founders. It's lonely at the top. That [00:39:00] saying is so true, and oftentimes we just corner ourselves in where we don't really have anyone else to talk to or we're talking the same industry, talk to everyone else. It's the group thing that's going on as opposed to looking at my own journey.

When I finally figured this out, and it was much later than it should have been sooner when I began to, to your point Mark, add people from other industries. Some of my biggest breakthroughs. It came from other industries, nothing to do with what I was doing, but it got me thinking and I began to do some things differently that weren't done in my industry.

And lo and behold, wow, it worked. And it worked amazingly well. So what you're saying is spot on, and that reminds me when you talk, and we talk a lot about this in the book, you talk about managing up and across and down, and I hear you on that. As founders though, how do founders need to manage themselves, particularly when, hey, they're the ones in charge, they're calling the shots.

They don't necessarily have that accountability partner [00:40:00] because they get to do what they wanna do sometimes for better, sometimes for worse.

Mark Herschberg: You. Certainly need to match down. Obviously if you have investors or a board, you are very actively managing up, and this is something I see a lot of first time founders. Stumble on. So definitely talk to peers to find out how do I manage up? How do I set expectations with my board? How do I communicate effectively?

You're going to have problems that as a given, and a good board will understand that if you can effectively communicate with your board, Hey, we have these challenges. Here's how we're addressing it. Your board will understand if you do it badly. Your board may lose confidence in you, not because you have a problem, but because they don't believe you can handle it well.

But if you don't have either of those, or even if you do, you still want to create a peer group, as you've pointed out, you want a group of other entrepreneurs or CEOs. I'm part of a number of [00:41:00] founder groups and entrepreneurial groups. I'm also part of CTO and technical groups. Both of those communities really help give me answers and support, and when I find a challenge I haven't faced before, even if it's one I face, but.

It's always challenging because as you pointed out, it's always unique. Say, Hey, here's what I'm thinking. Again, you've got this peer group, you've got this support. You don't have to do it alone. So that's why finding that group now, whether you're going through a formal program like YPO, you can find formal groups where you're paying a fee and they've got actively matched. You can create informal groups of just peers, maybe local to your community. Maybe it's just others.

Maybe it's virtual, but keep a regular cadence that might be monthly. Maybe it's weekly, if that's what you want. Keep that regular cadence, support each other and use them as your accountability partners. Help each other out because we're all gonna stumble. And especially as founders, we get distracted.[00:42:00]

It's so easy to say, ah, I've got this employee. He's difficult. But sales. Sales, I'm really focused on sales and that just festers and it's easy to get distracted. So these accountability partners say, it's been two months. It was fine. You had to get that sale closed. Now you have to address it.

Jeffrey Feldberg: Absolutely. And from the CEO peer groups, even the Deep Wealth community where exactly what you're talking about happens. But it reminds me from one of the quotes in your book, and I loved it. Always have a plan. Even a bad plan is better than no plan at all. And that's Professor Jason Rosen Hills. I highlighted that and put that off to the side because, hey, something's better than nothing.

We can always adapt and change. And before we go into wrap up mode, question about the Career Toolkit. So Mark, when you were writing that, was there one part that it was hard to write, not because it was hard. Intellectually you're a smart guy, but it was hard because it was something personal that you are perhaps facing or is challenging yourself and let me think this over here.

Or is that really where I want [00:43:00] to be with that? Anything like that ever happen to you as you're writing the Career Toolkit?

Mark Herschberg: I would say maybe the last chapter, which is ethics

And the challenge. There I have read hundreds of other business books and books on the various topics I write about ethics barely gets mentioned. I feel very strongly about, we have to be ethical in our businesses. Unfortunately, it gets no mention or maybe a little lip service.

The skills in the book, by the way, this comes from lists. This isn't just Mark dreamt it up one night. This comes from surveys of companies where I say, these are the skills we're looking for. And these lists, maybe they're five long, maybe they're 50 long, depending how you break it up. And while ethics is on the list, I always feel it's the redhead stepchild.

Of corporate values, it's always Oh yeah. Nice to have. But we're gonna sacrifice that first for anything else, for profitability, for stability, for anything. And so writing it, there was [00:44:00] maybe a lot more emotion. Not that the book itself is emotional, but I feel very strongly, and I provide a lot of cases of, look, here is how businesses compromise their ethics, and here's how it's going to one day potentially impact you or your children.

When you take these ethical shortcuts, I point out how would you feel if someone else took that shortcut on your child's toy or on the subway system or something else. And in fact, we are often incentivized to take that shortcut. So there was. Maybe a lot more emotion. Hard to be dispassionate when writing that chapter.

Jeffrey Feldberg: Words to the Y is and Mark, as you're talking about that I'm actually going back to my liquidity event and we had myself, my business partners ahead of time. Thank goodness we did this. We had our deal points and our no-fly zones. So either if it's not gonna be in the deal, we're walking away from the deal table, or if this isn't the deal, we're walking away from the deal table.

But the reason I mentioned that there was so much pressure on us to meet the projections and to get to the [00:45:00] profitability levels and the certain KPIs that we had projected out there, it would be very easy. And I saw firsthand to cut corners or to go against who we are or against our ethics. Oh, it's just this one time.

And if we do this, we're gonna benefit from personally no harm, no foul. It's a slippery slope, and once you start that, there's no going back. And thankfully we had our north star and we kept to that, but having not done that, it's so easy to just start small and boom. Before you know it, you're in a whole heap of trouble.

Mark Herschberg: As such a great example, and this is why I talk about in the. Ethics chapter, creating guardrails so you don't start to go down that slope. You also illustrate a fantastic technique in negotiations, which is before you go in, you do some pre-planning, and you have, what are we aiming for? What is our batna?

The places where we would walk away? What are some of the boundaries or the things we really wanna fight for or not? So really fantastic [00:46:00] example of key skills are going to help you be more successful with your business.

Jeffrey Feldberg: Absolutely, and what I love about the Career Toolkit, it's an embodiment of everything we talk about. Going back to step two X-Factors of how do we identify those X-Factors in our business that makes it insanely valuable to our existing customers, to our future customers, to our future buyers from.

Buyers who are gonna be buying our existing products and services, buyers who perhaps are gonna be investing or buying into a company. And one of our X-Factors, it's the team. Another X-Factor is the culture. And to me, they are linked together. If you have the right team, that's usually a great sign.

You're gonna have a rich and thriving culture and vice versa with that and the tools, the strategies in the Career Toolkit. Absolutely help us hit it outta the park in terms of not having to figure this out on our own or trying to, well, I'll do an experiment on myself, and years later, we're still doing it.

You've already done that for us. You've done the heavy lifting. We can now take what's there, make it our own, and now [00:47:00] apply those best practices to take ourselves, our company, our team, to the next level. And speaking of that, Mark, before we go into rapid mode. I have a whole list of questions I haven't yet asked as we bump up again some time.

That said, is there a question I didn't ask or a topic theme or message that we haven't perhaps gotten out there yet that you'd like to share with the DU Both Nation before we wrap things up and go into wrap up mode? I.

Mark Herschberg: I would just like to note when you think about the skills in the book, again, they apply universally to everyone. Because you do want even your junior people to be good at communication, at leadership, at networking, and even for you as a founder and owner, I get so much Well, your first chapter's career planning.

I don't need that. I'm A CEO. Career planning isn't just about changing your titles. For many people, that is part of it, but the titles really represent a different set of skills. And even as a founder, [00:48:00] you need to grow and evolve. Your title might not change, but you need to say the skills. I need to run my business at five people and a million dollars in revenue.

It's. Going to be different from the skills I need to run a team of 500 people and a million dollars in revenue, and creating the career plan to develop yourself to get to where you need to be, to where the puck is going as you grow your business. Critically important and often overlooked.

Jeffrey Feldberg: It's a great point. And Mark, as you're bringing that up, is one of the things I didn't have a chance to speak with you about, and thank you for sharing that because what I saw in the Career Toolkit, and you're right, a founder and entrepreneur. Entrepreneur's gonna say, well, yeah, I don't, I'm not an employee, I don't need this.

Actually you do because it's called your Exit. And like myself or so many other founders, I failed post Exit. That's where my biggest mistakes came, not pre-ex Exit, it was post Exit. And when you have that way of thinking, the strategies, the best practices that you talk about in the Career Toolkit, I can begin to prepare today.

For my Postex Exit life [00:49:00] and be very well prepared and confident. Okay, I have a life outside the business. I am not the business. The business is not me. The business runs without me. And when I'm no longer part of the business, as crazy as that may sound, I know what I'm gonna be doing and I know what my life looks like because I have my identity.

And it's a terrific tool for being able to do that. And thank you for taking that message and putting that out there and deport Nation again. We're not wrapped up here, but do go to the show notes, click on the link, and pick up the Career Toolkit. You'll come out of it a whole lot better than when you came into it.

So Mark that said, we're gonna go into wrap up mode and it's a tradition here on the Deep Podcast. It's my privilege, my honor. Every guest I ask the same question and it's a really fun question. Lemme set this up for you. When you think of the movie Back to the Future, you have that magical DeLorean car that will take you to any point in time.

So Mark, it's tomorrow morning. This is the fun part. You look outside your window. Not only is the DeLorean car curbside, the door is open and it's waiting for you to hop on in which you do, you're now gonna go to any point in your [00:50:00] life. Mark, as a young child, a teenager, whatever point in time it would be.

What would you tell your younger self in terms of life wisdom, life lessons, or, Hey Mark, do this, but don't do that. What would it sound like?

Mark Herschberg: I would find myself probably as a tween or teen and go back and say. Soft skills matter. I was such a hardcore eighties nerd stem. I have multiple degrees from MIT. I did really well in that left brain stem approach, but I stumbled early in my career because I didn't have some of these skills, and that's why I set out to learn them for myself and quickly realized I wanted other people to have them.

If I could go back, if I could have learned these skills. Much earlier. I think I would've come out of the gate much faster and would've been further along on just certain things I hope to achieve in life. Now, the good news is we might not have a time [00:51:00] machine, but you can always start today. You can always move forward.

Whether it is getting better at these soft skills or whatever skills you are trying to develop, you can start today and you'll be better off tomorrow for having done it.

Jeffrey Feldberg: These are truly words of the Wise in Deep Wealth Nation. Again, this is coming from, I know you know him as Mark, but he's a startup, CTO an MIT instructor. He is done cybersecurity. He's been an acclaimed author best. Selling author. This is really words to the wise, and it's something that's so easy to overlook again because it doesn't show up in a spreadsheet or a complicated formula, but it's what makes those formulas work out so well when we master those soft skills.

That's the irony of all this. And Mark, before we wrap this up, someone in the audience, someone de Both Nation, they have a question for you. They wanna speak with you. Maybe they even want you to come speak to their group, or have you advise them or become their CTO. Where would be the best place online to reach you?

Mark Herschberg: I'm going to give you three different places because there's three different sets of resources. You can [00:52:00] certainly find me on LinkedIn and because my name can be hard to spell. Hirshberg, H-E-R-S-C-H-B-E-R-G. If you just remember. linkedin.com/in/hershey, like the candy bar, H-E-R-S-H-E-Y. That's my LinkedIn profile.

You can certainly find me there, but then you can find me on my other websites along with a bunch of other resources. The first is the Career Toolkit book.com, and on that website you can of course, see where to buy the book. There is a contact form whether you want the form, my email, social media. It's all there.

There's also a resources page with a number of free downloads, including how to create that internal career development peer group. Completely free to download. And I have hundreds of articles that I've put on the website. I go a lot more into ai. I reference that, but also all these other skills I get deeper into negotiating communication, leadership, [00:53:00] and these other skills.

All completely free. That's all at the Career Toolkit book.com. And then finally there is brain bump. And if you go to Brain bump.app, you can go to my website there and you'll see where to download the free brain bump tool from the Android or iPhone store. You can also go to the store and just search for brain bump.

Download the tool there. There's also a contact form on there, so brain bump, the Career Toolkit, book.com and LinkedIn. You can find me in any of those.

Jeffrey Feldberg: And deport nation allotted links to. Every, but here's the great news. Go to the show notes. It's all there. It's a point and click. It doesn't get any easier. Well, that said, Mark, congratulations. It's official. This is a wrap, and as we love to say here at Deep Wealth, may you continue to thrive and prosper while you remain healthy and safe.

Thank you so much. 

So there you have it, Deep Wealth Nation. What did you think? 

So with all that said and as we wrap it up, I have another question for [00:54:00] you.

Actually, it's more of a personal favor. 

Did you find this episode helpful? 

Have you found other episodes of the Deep Wealth Podcast empowering and a game changer for your journey? 

And if you said yes, and I really hope you did, I have a small but really meaningful way that you can actually help us out and keep these episodes coming to you.

Are you ready for it? 

The dramatic pause. I'll just wait a moment. Drumroll, please. Subscribe. Please subscribe to the Deep Wealth podcast on your favorite podcast channel. When you subscribe to the Deep Wealth Podcast, you're saving yourself time. Every episode automatically comes to you, and I want you to know that we meticulously craft Every one of our episodes to have impactful strategies, stories, expert insights that are designed to help you grow your profits, increase the value of your business, and yes, even optimize your post exit life and your life right now, whatever you want that to look like.

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So all that said. Thank you so much for listening. And remember your wealth isn't just about the money in the bank. It's about the depth of your journey and the impact that you're creating. So let's continue this journey together. And from the bottom of my heart, thank you so much for listening to this episode.

And as we love to say here at Deep Wealth, may you continue to thrive and prosper while you remain healthy and safe. 

Thank you so [00:56:00] much. 

God bless.