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Index/Finance/Behind The Numbers With Dave Bookbinder
Behind The Numbers With Dave Bookbinder artwork

How IT Strategy Impacts Business Value, Risk, and Exit Readiness - Keith Tessler

Behind The Numbers With Dave Bookbinder · 2026-05-19 · 28 min

0:00--:--

Key moments - from our scoring

Substance score

44 / 100

Five dimensions, 20 points each

Insight Density10 / 20
Originality9 / 20
Guest Caliber10 / 20
Specificity & Evidence7 / 20
Conversational Craft8 / 20

Keith Tessler of CMIT Solutions discusses why small-to-mid-sized businesses (10-150 employees) must treat IT strategy as a value driver rather than an expense. Most critical insight: cybersecurity threats now target smaller companies preferentially, with email breaches posing the greatest risk - yet two-factor authentication and password managers remain drastically underdeployed despite being inexpensive. Tessler addresses practical vulnerabilities including malicious use of legitimate remote-access software like Splashtop and emphasizes how corporate culture shapes security outcomes. For business owners planning exits, IT documentation gaps emerge as major friction points: many lack basic records of where systems are hosted, passwords, or configurations, creating institutional knowledge risks that directly impact succession planning and valuation. The conversation explores how AI is democratizing automation and code-generation capabilities while simultaneously eliminating junior-level information worker roles - mirroring the PC revolution's impact on clerical jobs. Most relevant for mid-market operators weighing managed services adoption, M&A due diligence, and leadership development in an AI-augmented workplace.

Key takeaways

  • →Two-factor authentication and password managers are zero-cost or minimal-cost cybersecurity measures that significantly reduce breach risk compared to outdated antivirus-only approaches.
  • →Email compromise represents the highest cybersecurity risk for most businesses, yet many remain stuck in decade-old security paradigms that leave them vulnerable.
  • →Undocumented IT infrastructure and tribal knowledge create major succession planning and exit readiness problems when passwords, hosting details, and system access aren't centrally tracked.
  • →AI is accelerating talent development and automating low-level information work, but struggles in fields requiring high accuracy tolerance like law, making the human-in-the-loop model critical.
  • →Small businesses are now preferred targets for cyber attacks because large enterprises have hardened defenses, and bad actors use AI to efficiently target many small firms simultaneously.

In this episode

  1. 1Introduction to IT Strategy and Business Value
  2. 2Overview of CMIT Solutions and Target Market
  3. 3Common Cybersecurity Vulnerabilities and Email Security Threats
  4. 4Bare Minimum Security Measures: 2FA and Password Managers
  5. 5Transition from Break-Fix to Managed Services Model
  6. 6IT Strategy and Succession Planning for Exit Readiness
  7. 7AI Applications in Business Automation and Talent Development
  8. 8People, Culture, and Cybersecurity Risk Management

Mentioned

CMIT SolutionsKeith TesslerDave BookbinderSplashtopPC AnywhereMarcus LemonisGallup

Guests

Keith Tessler

Topics in this episode

Password managersTwo-factor authenticationemail securityCMIT Solutionsremote control softwareSplashtopcybersecurity due diligencemanaged services modelsAI accuracy limitationsM&A IT integration

Questions this episode answers

What are the two most important cybersecurity measures that cost small businesses little to nothing?

Two-factor authentication on email systems and password managers. Two-factor authentication (a text or app-based code requirement) significantly reduces breach risk at zero cost, while password managers cost a couple dollars per user monthly and eliminate weak password reuse.

Why are small businesses now more targeted by cybersecurity threats than large enterprises?

Large businesses have invested heavily in cybersecurity defenses over the past five years, making them harder targets. Threat actors have shifted focus to small businesses, which typically lack sophisticated security measures, and AI now enables attackers to target many smaller organizations efficiently at scale.

What is the biggest IT mistake Keith sees with businesses preparing for sale or succession?

Lack of IT documentation and organization. Critical information exists only as tribal knowledge - nobody knows where websites are hosted, what passwords are used, or how systems are configured. When knowledgeable employees leave, this institutional knowledge walks out the door, complicating transitions and reducing business value.

When should a growing company transition from a break-it-fix-it IT model to managed services?

The threshold is when downtime becomes unaffordable. If computer downtime for two days would cost thousands in lost productivity or revenue, it's time to proactively manage IT rather than react to failures.

How is AI impacting job development and junior-level positions in professional services?

AI is eliminating traditional junior-level information worker roles (like junior developers and junior lawyers) that historically served as talent development pipelines. This mirrors the PC revolution's impact on administrative jobs, forcing organizations to rethink how they groom future leaders.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

10 / 20

A handful of useful operator nuggets (remote-control software as a new attack vector, dirty data killing M&A integrations, AI pushing automation capability down-market), but much is standard SMB advice like 'turn on 2FA' and 'use a password manager' padded with rapport chatter.

bad actors are sending emails with links...it is, let's say Splashtop, you install on your computer
AI has made both writing code and interconnecting software easier and cheaper

Originality

9 / 20

Mostly familiar framing (people/process/technology, keep-it-simple, IT-as-strategic-advantage), with a few slightly fresher observations like AI stripping out entry-level 'information workers' analogous to the PC revolution and the remote-control-software trend.

what AI is doing is stripping out the next level of those information workers
the high performing asshole I think is a trap that I think a lot of business owners fall into

Guest Caliber

10 / 20

Guest is a genuine practitioner running an MSP serving SMBs and a serial entrepreneur who sold a business, but the scale and seniority are modest and the perspective stays at the small-business franchise level.

we're in the business of, uh, helping small to mid sized businesses with their technology
I sold a business about seven, eight years ago. I was the integrator

Specificity & Evidence

7 / 20

Very light on hard evidence: employee-count rules of thumb and vague pricing ('couple of bucks per user per month') but no named companies, dollar figures, or data; anecdotes stay generic ('a client recently').

you get to around 10 employees...around 125, 150 employees, time to have an IT department
a couple of bucks per user per month

Conversational Craft

8 / 20

Host asks reasonable structured questions and adds his own anecdotes, but it's a warm, softball chat with repeated 'great segue' praise and no genuine pushback or challenge to any claim.

Man, another great segue. Thank you for that.
No pressure here. But what is one thing that you wish every business owner really understood

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker B69%
  • Speaker A31%

Most-used words

businesses21system17systems15today13call13seeing12data11small11keith10cybersecurity10frankly10computer9interesting9part9level9owners8

Episode notes

Technology problems rarely start with technology. They start with leadership decisions, culture, and treating IT as an afterthought instead of a strategic asset. In this episode of Behind The Numbers With Dave Bookbinder , Dave speaks with Keith Tessler of CMIT Solutions about why smart companies are shifting from reactive IT support to proactive technology management and how those decisions directly impact risk, resilience, scalability, and enterprise value. The conversation explores the biggest cybersecurity threats facing small and mid-sized businesses today, including phishing attacks, business email compromise, and the growing misuse of remote-control software by bad actors. Keith shares practical, low-cost protections every business should implement, including two-factor authentication, password managers, employee awareness training, and stronger internal controls.

Full transcript

28 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Foreign mhm. And welcome to behind the Numbers. This is the show where we go beyond the data to explore the people, the stories and all the insights that really drive business success. I am M. Dave Bookbinder. I'm known as a business valuation expert and bestselling author. And I thank you for joining me today. Most business owners don't really think about it until something breaks or sometimes even worse, until there's a security issue. And by then the damage is already done. The reality is your IT environment plays a critical role in your company's risk profile, operational efficiency and overall value. And ignoring it can be a very costly state. I'm joined today by Keith Tesler of CMIT Solutions, who helps businesses take a more proactive and strategic approach to IT and cybersecurity. Keith, it is great to have you here on behind the Number.

Speaker B: Thanks for having me, Dave. I really appreciate it.

Speaker A: It's a pleasure. For those who may not be familiar, why, uh, don't you give us a quick overview of CMIT Solutions and the types of clients you serve?

Speaker B: Yeah, we're in the business of, uh, helping small to mid sized businesses with their technology. You know, I usually describe it this way. You know, as, as a business, you get to around 10 employees, you realize you can't do it yourself. You need a little help, you need something professional. Usually when you get to around 125, 150 employees, time to have an IT department. We live in that space there. Companies that are too big not to have help and too small to do it themselves, we're there for them.

Speaker A: Yeah, and the risk for those folks is tremendous. We're going to talk about that today, but before we do that personally, what drew you into the IT services space and what keeps you passionate about today?

Speaker B: You know, I can't say I know what drew me in because frankly, I was in third grade when I saw my first computer. I was that kid who loved computers from a very early age. By fourth grade, the teachers were pulling me out of class to help them with their computer problems. So I like to say that's when I got my, uh, start in tech support.

Speaker A: Everybody needs one of those. What keeps you inspired about doing it today?

Speaker B: You know, I love the fact that I'm always learning. I find so many people, you know, they get into a rut. They do the same thing over and over. And for me, I love exploring new worlds, if that makes sense. You know, very excited when the new thing comes out because I want to see how this work, how does it tick, you know, I'm the kind of person some people fear going from Android to Apple and Apple to Android. They couldn't imagine making the switch. I'm excited by it. I want to see how the other op, how the other world works. It's all fun and games to me.

Speaker A: Yeah, I'm perfectly fine living uh, in my own little operating system and not uh, willing to make the moves most of the.

Speaker B: I totally get that.

Speaker A: I'm glad you're there for the rest of us. So Keith, one of the things that I'm sure you see. I know I see it all the time when it comes to, we'll call it professional services. A lot of business owners still think of it as an expense. How should they be really thinking about it as a driver of enterprise value?

Speaker B: You know, that's a really interesting question because if you treat your um, IT as an expense and do the minimum, you know, the minimum required just to get by, then you're really not going to get much value out of your it. But it can be a, ah, real differentiator for businesses if you use it right. You know what's interesting is today every software package you use has more features, options, switches than anybody actually uses. And if you spend the time to actually really explore these packages, learn what really will make your business sing, what will really drive your business, and then most importantly, get your team to use them, do the trainings, get them integrated, get them to be habitual parts of what you do, you really can make your business sing and have an edge up over your competitors that don't really know how to use the packages they're paying for.

Speaker A: Yeah, isn't that fascinating? So kind of dovetailing from that then, what are some of the biggest mistakes that you see companies making when it comes to their IT strategy?

Speaker B: You know, a lot of people I see are stuck in old paradigms. I, uh, you know, I talk getting onto cybersecurity. You know, people say, oh yeah, I've heard about this, but I've got antivirus, aren't I good? And the sad part is, is they're like two decades behind and they don't know it. You know, frankly the biggest risk most clients have out there, most businesses have out there, is not their computers, it's your inbox. You know, the big hacking today is breaking into your email. And to put some thought on it, if someone broke into your email, think about how much they could learn about you, your business, what you're doing, and how they could leverage all that information for nefarious means. Um, so it's a really good example where a lot of people are stuck in old paradigms.

Speaker A: Yeah, I want to unpack cybersecurity a little bit, since you, uh, opened that door for me with a beautiful segue there. I know we get these, uh, videos at my work, where we have to go through them at least once a month so that we're alerted to the latest and greatest ways that the, uh, they call them, the bad actors can get at your computer. And, man, there are so many, and they're so creative. So what are some of the most common vulnerabilities that you're seeing in small size?

Speaker B: Yeah, so I'm sorry to say we've seen a new trend this year where they're using remote control software. This is your PC anywhere, your Splash top, all these remote control packages that people use to remotely control their computer. And maybe they jump into their work computer from home or something like that. They're legitimate programs that got good use. But now what we're seeing is bad actors are sending emails with links. We all know not to click on bad links, but we're all human. You download something, it doesn't look like that, but it is. It is, let's say Splashtop, you install on your computer. And now that remote actor uses that bad actor, excuse me, uses flashtop in order to access your computer. And the problem is, it won't set off a lot of alarm bells because it's a legitimate program. It's not like it's a virus or something like that. So a lot of the systems designed to protect you won't recognize it as a threat. And I'm sorry to say we've seen that happen multiple, multiple times since the

Speaker A: beginning of the year.

Speaker B: It's their new, uh, favorite toy, so to speak.

Speaker A: Man, they just keep getting better and better. When the business owner tells you that they're too small to be a target, how do you respond to them?

Speaker B: You know, that's exactly the opposite. What's happened in the marketplace in the last, I don't know, five years is big business has really gotten their act together in terms of cybersecurity. You know, if you think about it, used to hear about the news, there was this big people that got hacked, this big bone hacked those news stories. They haven't stopped, but they've gone down. And that's because big business today really has their act together in terms of cybersecurity. So what's happened is the threat actors are looking to small business now, unfortunately, because they realize most of them don't have their act together. They're easy targets. Obviously they're smaller targets, but frankly, with the help of AI, they can now do more smaller targets, easier than they used to be able to. And they're really seeing those as their growth market.

Speaker A: Yeah. And a lot of those smaller businesses, besides being less sophisticated, don't have the funds to maybe necessarily make the investment. So what are some of. The. Call them the bare minimum cybersecurity measures that every company should have.

Speaker B: You know, I'll give you one that's. By the way you talk about the funds. It costs nothing. Okay. Every system out there has it and you absolutely should if you don't, which is two factor authentication on your email system. I walk into more businesses today that haven't even installed two factor because they say, oh, our users can't handle it or they won't know what to do with it or it's too much a pain in the butt. And the reality is that one simple thing that costs small business nothing makes a huge difference in people's ability to break into your email.

Speaker A: Yeah. So for those who may not be familiar, the two factor. Authentic. Authentic. That annoying thing where you try to log in and they need to send you a text message to boot.

Speaker B: Yep. They send you. Or sometimes you get it on an app. They say, give me a six digit code off an app. Yeah, one of those. It is annoying. I give you that. But it's a very simple thing you can do. And the other one I'll give you, and I like this one a lot because it is both helps with security and it makes life easier, is use a password manager. You know, use something to store your passwords that it works. It'll generate a random horrible password that no one can guess. You only have to remember one password, which is a huge relief. You don't know how many people I talk to who can't remember half their passwords. They just reset passwords all the time. Um, and it costs very little. This is very inexpensive. You're talking a couple of bucks per user per month for a really nice upgrade and protection and it makes your life easier.

Speaker A: Yeah. Uh, Keith, at what point does a growing company need to start thinking about moving away from, I'll call it the break it, fix it it model and into more of the managed services model? You know, you have a threshold.

Speaker B: You know, I wouldn't say there's a specific threshold. The threshold is when you say I can't afford to be down and most businesses today can't live without their Computers. If you say, look, if my computer blew up tomorrow and it would cost me thousands of dollars because I couldn't work for two days while I put this back together, that's when it's time to talk to someone about how to make sure that doesn't happen for you.

Speaker A: Yeah. So in my world, in the valuation space, a lot of times I'm talking with business owners, uh, about succession planning, exit planning strategy around things that drive value and succession. Uh, it doesn't often come up, but clearly it plays a key role in the scalability. So why don't you talk a little bit about the role of it, especially for those companies who may be prepared.

Speaker B: Yeah. And you know something? I see a lot in it, particularly with businesses that haven't thought about it much, is they don't even know where things are. A lot of the IT information exists as tribal knowledge, not as any kind. There's no documentation system. There's nothing keeping track of things. You'd be amazed how many people I talk to who don't even know where their website's hosted. You know, it's on their credit card, they don't know which charge on the card it even is. They don't have the password to it. And then they go to make a change or someone leaves who maybe knew that information. They don't even realize the password walked out the door when the person left. And, and it could be that, it could be their email system. It could be a whole host of things where. I see where if you haven't thought about, you know, keeping this stuff organized and keeping everything properly documented, um, in a way everyone understands, it kind of gets lost. I see this all the time with businesses often find sometimes I'll onboard a new client and half of what I'm doing is just getting them organized so they have everything in one place so they can, so there can be a succession to a next person.

Speaker A: Yeah. Part of what we talk about, or I talk about a lot, is the idea that the institutional knowledge that walks out the door. So we'll add the uh, the passwords to that list as well.

Speaker B: Uh, please do.

Speaker A: Those are things that you just, people just don't necessarily think about, you know,

Speaker B: and I get it. It like, you know, you have a website, it runs, everything's good, you're happy. You don't realize the fact that for five years no one's even know who's hosting it or how it's happening.

Speaker A: Yes, exactly. It's just the uh, the wizardry that happens behind the scenes.

Speaker B: Absolutely.

Speaker A: So, man, another great segue. Speaking of wizardry, I want to talk to you about AI. Uh, where are you seeing, we'll call it Real and Practical applications AI in your clients at this time?

Speaker B: Yeah, great question. So what I'm seeing is, I'll call it a push down of the ability to automate. So if you go back at the pre AI two, three years ago, what you saw was, you know, small businesses used off the shelf software. Medium sized businesses would use off the shelf software, but then interconnect them, make connections between them. They could afford to build those connectors so their software would talk to each other. Large businesses would build their own packages from scratch. They would write code and build businesses from scratch. And those levels still exist in the world. However, AI has made both writing code and interconnecting software easier and cheaper. So it's now becoming available to more and more businesses. So businesses that maybe before couldn't afford to interconnect their systems now can and are seeing efficiencies. And I'm seeing people getting first mover advantage in doing those kind of projects before their frankly competition realizes it's viable. People who couldn't interconnect are now interconnecting.

Speaker A: So I'm seeing that what's overhyped right now and what's actually delivering the real roi.

Speaker B: You know, what I'm seeing in AI is it has some huge abilities. But I think the real overhype, frankly is in what I'll call accuracy. The clients that I'm seeing who are going, no, AI doesn't work are those that have, I'll call it little or no tolerance for mistakes. I think lawyers are a great example of this where, you know, AI has, look, all lawyers do is process documents. AI is great at processing documents, but it also makes a lot of mistakes. And so a lot of lawyers are saying to me, look, this is fabulous. They wrote a brief for me, it's good, but it made three mistakes that could get me disbarred. So any field that has a high demand for accuracy or a low tolerance for mistakes, it still isn't there yet. It still isn't accurate enough. You know, the flip side is you look like people writing code. If you write code that's wrong, you see the bug, the human can fix the bug. It's a high tolerance for that mistake. It's not a big deal. So those are where you're seeing it and where you're not.

Speaker A: Yeah. It's interesting when you talk about the law firms, as I was, I Served lawyers all day long and had lunch with one not too long ago. And we were kicking around the idea of the AI in their business and how does it impact their fees? What are the client expectations? She told me that they bifurcated a little bit where in certain instances they will say we'll use AI for this and we'll reduce our fee accordingly. But man, to your point, it's trust but verify, verify and verify.

Speaker B: No, absolutely. The other thing we're seeing with AI, and I think this is even more interest, uh, interesting is I'm starting to see, and I've seen it in my own business and I've seen it some of my clients, it's helping develop people faster. Now when you give people this AI tool, um, now they have access to more information. Frankly, they spend less time running around the Internet looking for things and more time actually learning from the AI. And so I've seen my technicians are really growing at a faster rate. Um, I was talking to a lawyer client of mine who says, remember, junior partners are coming along faster than they used to simply because the AI is becoming a teacher and a tutor for these people. So it's really interesting.

Speaker A: Yeah, so since you brought that up, another anecdote that I hear in the market and conversations with CPA firms, it sounds like they've, they've spooled up their own AI models to the point now where they're, they're actually contemplating or already begun eliminating a lot of the junior level positions that used to handle that work. And those folks generally by nature aren't wired to necessarily be business developers. So what they're finding that the firms are finding is they now have these mid level managers who grew up not thinking about selling. There's no team underneath them to groom up. What's the next gen of the leadership of the organization going to look like?

Speaker B: You know, and this, uh, and my entry is the same thing, you know, the job I did out of college, that junior level developer who was writing code. That job is gone. And I think we're gonna have to find new ways to develop talent than what we used to because those early entry level jobs are now being taken up by AI. What's happening with AI right now I think is very analogous to the PC revolution that happened when you and I were kids, Dave. And what I mean by that is, you know, when I was a kid, every office had tons and tons of administrators, secretaries, there was a whole information, a uh, whole level of low level information workers that frankly disappeared when the PC came along. And to me, what AI is doing is stripping out the next level of those information workers, so to speak.

Speaker A: Yeah, man, we'll wait and see how

Speaker B: that one unfolds, but it'd be very interesting.

Speaker A: Yeah, it's not all that it's been cracked up to be. So listen, among other things, besides being that, that kid who always needed to be, uh, doing the tech stuff, if you're an entrepreneur and business, um, owner, and I want to tap into that part of the brain, so to speak. Um, and when we talk about business success, famous TV show, uh, the Profit with Marcus Lemonis talked about people, process, and technology, the three big things. Where does that formula break down most often?

Speaker B: People. Look, people, to me, are the most important and the most difficult part of any business. You know, I think hiring and good hiring is probably the toughest part of being a business owner. And look, I've been an entrepreneur my whole life. Um, and if I've learned anything is the right people, people will make a business and the wrong people will absolutely break a business, particularly small business, because each person has a larger impact.

Speaker A: You know, you're preaching to the choir on that. Let's continue that story just a little bit more. Talk a little bit about the role that corporate culture plays, not only in terms of performance, but in the wheelhouse of protecting digital assets.

Speaker B: So, you know, look, obviously corporate culture and how your people work make a huge impact on the bottom line and also like how your people feel about things, how, how your clients get treated huge amounts. But the other thing is, is, I'm sorry to say, today, cybersecurity, most of the breakdowns start with a person making a mistake. You know, they download something they shouldn't, they put their password in somewhere they shouldn't. And so having a corporate culture which is aware that cybersecurity is a problem you need to address is huge. If you put your head in the sound and say, oh, we hired a guy and he's got some systems on it, it's good, then your people will forget about it and they won't think of it. And that's how they make mistakes. If you have a corporate culture that says, look, this is a threat we need to manage, this is something that is important for the protection and continuation of our firm. Protect our clients data, and it's on top of mind. People are a lot less likely to make mistakes. You know, I had a client recently where there was a hacking incident, and the person who got hacked recognized it. Within seconds. They literally turned off their computer and called us within seconds. And that was fabulous. Because of that, what could have been a very horrible attack was totally mitigated and there was no damage.

Speaker A: You know, when I was thinking about that question, uh, and I started to really chew on it. In my first book, the New roi, New ROI Return on Individuals, one of the chapters I talk about is dealing with toxic employees. And the Gallup data seems like since the beginning of time shows that about 30% of the workforce is engaged. So 7 out of 10 people show up not really interested in being there. But some component of that 7 out of 10 are toxic. They're not just disinterested and scroll on uh, social media all day long. They're trying to actively destroy you and take you down. And with digital assets, cyber and all the password exposure you talked about, just maybe talk a little bit about that risk of the toxics who are uh, doing more than just trashing you on Glassdoor.

Speaker B: Yeah, I mean, because someone who's not engaged is not going to care enough to like double check a link they click on. They're not going to care enough to worry about, you know, is this the right thing to do? Or even just more so that not going to care enough. Oh, I can send this file that contains Social Security numbers, numbers or private other data out. They're just not going to care enough to do those things. And you know, the problem with a lot of these high performing a, and I won't use the word um, that a lot of organizations tolerate because they drive revenue or drive other things.

Speaker A: You can use the word. We've talked about not having the, or having the no assholes policy here. So it, it's well done.

Speaker B: I mean the high performing asshole I think is a trap that I think a lot of business owners fall into, particularly salespeople because they drive revenue or key operations people because they say they can't live without them. And the truth is no one in this planet is as important as you think they are. You know, I always tell the story of my own self, which is, you know, I sold a business about seven, eight years ago. I was the integrator to put it in the US terms of that business. I was the center of the company. I um, had, you know, overseen the rating of all the code that ran the business. And people who bought the business were very scared of what would happen if something happened and I wasn't around. And as part of the sale they tied me into an agreement and they made me sign a document saying would help them at a predetermined rate. And all this stuff. And then after the sale was over, they called me exactly zero times. So as important as everyone in that company thought I was, I wasn't that important. And I assure you, no one else is either.

Speaker A: Man, another great segue. Thank you for that. I want to talk about M and A and due diligence. So from your lens, Keith, how does it show up in due diligence when company is being wired?

Speaker B: You know, I think it's actually overlooked a lot, to be honest, because I've done a number of deals in my life and a lot of people look at the IT as almost an afterthought. We'll do the deal and then we'll integrate the IT systems, we'll figure out how to make it work. Um, and you never really know what's going on in IT until you dig deep into it. You know, some companies have beautiful IT that is easy to integrate or move or merge into another system. Other companies, frankly, have these dirty, messy systems that aren't well put together, that aren't well designed. And to try to just merge that data in is going to be a nightmare. To try to just get that system to go into their system is going to be a nightmare. And often I hear about, I get called in, frankly, after the M and A deal is done and they're trying now to do it, and they say we can't get their system to talk to our system. And I look at the new, the old system going, well, no wonder anyone who looked at this system before would have known that. But people just kind of assume, oh yeah, the IT geeks will figure it out. Not a bad idea, particularly if that is an important part of the deal. Get someone to do some due diligence on it before you do it.

Speaker A: Yeah. And what are the red flags that buyers are looking for in a company's IT environment?

Speaker B: You know, I think the number one thing is dirty data from a mergers and acquisitions point of view. If a client has well structured data and everything's put together, you'll have no trouble migrating it to another system. If you've got dirty data where things are not done properly, or there's multiple three different systems that don't really talk to each other, but we kind of keep them kind of, sort of in sync. Getting that kind of data over to another system into a new system can be a nightmare and take way longer and be way more expensive than people imagine. It would have been.

Speaker A: Good stuff, man. So for the business owner who's listening right now and maybe thinking about selling in the next two to three years. What should they be doing right now

Speaker B: from an IT stands, You know, get your IT house in order. And I'm, um, not, I'm not talking about cybersecurity. I'm talking about your data structure, your workflows, all those things that make for good operations. And by the way, these will also improve your operations. These will also make you more efficient as a running business. But it also means that if someone can come in and very simply lay out your structure, your workflows and your data structure, you're in good shape. If you got to go, oh, yeah, there's this, but we also do that and there's this on the side and this over here. That's when you're going to look. So anyone who's buying that business should see a red flag in terms of your.

Speaker A: It's awesome. Thank you for that. And just in terms of general IT advice, if you could give the business owners a simple. Call it IT checklist checkup checklist, what would you have on that?

Speaker B: Yeah, uh, I'm a big fan of, you know, keep it simple stupid. Meaning businesses that have fewer systems are usually much easier to run and run much more efficiently than a lot of systems. And I walk into business and they say, we got two or three systems on the business. That's great. When I walk in and they go, we got accounting, oh no, but Ars are over here and ah, APs over here and we use this for billing. That's when I know there's going to be trouble. You know, no small business is, I'll call it deserves to be complex enough to have 17 different platforms that they're running on. Keep it down to a few number of systems that work well. Like I said before, there's a lot of systems that have a lot of features today and then really leverage those systems to the hill. Most of the features in most systems are underutilized.

Speaker A: I'm sure when you go into, uh, to work with clients, you see a lot of things, we'll call them investments that turned out to be wasted time and wasted money. Talk a little bit about some of those types of things, what are some of the wasted efforts and then flip the coin for us and talk about an investment or two that really consistently pays off.

Speaker B: You know, I'm going to say someone, an old partner of mine once said, uh, cheap solutions cost money, good solutions save money. And what I mean by that is a lot of times I see business owners who they think they're, oh, I found, I know there's. This is the best solution out there and this works well. But I found this, and I think it's almost as good and it's half the price, but it's not as good. And they spend a lot of time and a lot of money trying to make it into something it's not. And they end up really spending more money in the long run. Or the whole thing fails and they have to throw the whole thing out. I've seen that multiple times. Or frankly, I get called in because this thing has failed and they go, why won't this work? And I'm going, it never was gonna, you know, and honestly, this is unharable. It happens more to the smart, the smartest people more than other people. It's the people who think they're too smart, who think they can outsmart the system and make it work that I see do those kinds of mistakes.

Speaker A: Hmm.

Speaker B: Um, the solutions I see that really work out there for businesses is when they spend the time to really understand their business. You'd be surprised how many businesses, Even small ones, 20 person firms, the owner doesn't necessarily really know how everything gets done.

Speaker A: Yes. Preach, Keith, preach.

Speaker B: And. But if you, when you put a system in place, talk to the people who are doing the process all day, every day and grill them. Because we talked earlier in this conversation about like, people getting stuck, those people tend to know exactly what's going on, but they also tend to be stuck in what they're doing and not being able to think like, oh, there's another way to do this. So the trick is to have a conversation to really understand what needs to get done and what the processes are and then work with them to kind of develop the new processes. If you're just working with the business owner, odds are you're going to miss them.

Speaker A: Yeah, absolutely. When you think about it from a strategic standpoint, how often should business owners be thinking about revisiting their IT strategy?

Speaker B: You know, honestly, not very often. Every couple of years is enough. Look, IT are major, major investments, you know, and if you're changing it all the time, you're probably spending more time running in circles than you are actually reaping the benefits of your systems. Don't get me wrong, things change, particularly in the last several years with AI, there's been a paradigm shift. If you haven't looked at your systems in terms of AI, you should. The flip side is, if you just did it last year, things haven't changed that much. You probably should wait a few more years before you look at it again.

Speaker A: Yeah. Interesting. You may just be chasing the new bright, shiny object before it's been fully vetted.

Speaker B: I call it the bleeding edge, not the cutting edge. You know, where it's not really ready yet.

Speaker A: Yeah, exactly. Bleeding edge, not leading edge. I've been on. I've been on that plenty of times.

Speaker B: You've been on the bleeding edge a few times in your career.

Speaker A: Many, many, many, many times. So, Keith, we're getting down to the short strokes here. I just have two more things for you, but, uh, this is big takeaways for the audience. No pressure here. But what is one thing that you wish every business owner really understood about it?

Speaker B: You know, you hit on it earlier. That it done right can really be a strategic advantage for the business. That it done wrong can really hold the business back. But the doing it right has more to do with understanding not about the shiny new tool. It's about taking the tools you have, using the hilt, and then most importantly, getting your people to actually use them and love them and say, this is a great tool. Um, and that's the kicker is getting your people to use them right and really make it part of your corporate culture, if you will, to exercise those tools.

Speaker A: Yeah, I know. We get it drilled into us every week. So it's. It's part of our culture for sure. And. And that's a good thing.

Speaker B: Yeah, no, I think that's great. I don't know too many companies that do that, and I think that's fabulous.

Speaker A: Yeah, for sure. So for the business owners who are listening right now and they can take just one thing away from this conversation, what should it be?

Speaker B: First of all, don't ignore cybersecurity threats are real. They're going after small businesses. If you haven't talked to a professional about securing your business, do it. Number two, think about your technology as a strategic advantage, not just a call center.

Speaker A: All right, well, because you've been so good and kind here, I'm going to throw one more question at you, if you don't mind. Um, another one big difference maker for the audience kind of actionable insights piece. But when you think about businesses that are truly leveraging technology well versus the ones that struggle, what's the difference in how they think about it at the leadership level?

Speaker B: The leadership is involved. The businesses I see that aren't succeeding is where they've pushed it down two or three levels down the chain to some lower level person. Just make sure it runs. The ones I've seen where they really make it shine are the Ones where the CEO COO are involved in the technology decisions.

Speaker A: Yeah, that's interesting. And how do you find that you get them actively involved in those types of things when maybe sometimes they're less interested in the IT element, more interested in driving top line?

Speaker B: Yeah, I think you've got it. They have. You have to get them to understand that this will drive top line and bottom line growth. And that's what that's about.

Speaker A: Really well said, my friend. Appreciate you being here, but before I let you go, I need you to tell the audience where they can find you, how they can connect with you if they'd like to learn more about your work.

Speaker B: You know, the best way to connect with me is on LinkedIn. I'm on LinkedIn. I post regularly on both technology and business. I'm, um, a fourth generation entrepreneur and I've been an entrepreneur my whole life. So LinkedIn Keith Tesla, just like my name.

Speaker A: Wonderful. And you do post some interesting things there. It's not just IT related stuff. Uh, folks out there definitely connect with Keith or at least follow him on LinkedIn. Keith, thank you so much for being with us today and behind the Numbers. Really appreciate it.

Speaker B: Thank you.

Speaker A: Alrighty. And thank you out there for listening to behind the Numbers. As I like to say, if you enjoyed the episode, please do leave us a review on Apple or Spotify. That really does move the needle and it helps future listeners find the program. Until next time, I'm Dave Bookbinder reminding you that the numbers tell the story, people bring it to life. Take care, gang. We'll see you next time.

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