Holistic Tech Advice w/ Elliott Friedman

Tech problems rarely start as tech problems. They start as messy decisions, unclear ownership, and tool sprawl that quietly turns into risk. We’re joined by Charleston-based business and technology advisor Elliott Friedman, who’s lived on every side of the table: founder, operator, CTO, and now a trusted guide for professional service firms and private equity teams navigating growth and complexity. 

We dig into what “holistic” advising really means in practice. Elliott shares the red flags he looks for when a company is headed for trouble, from leadership teams treating technology as a grudging expense to organizations dragging hidden tech debt and paying for SaaS bloat they barely use. We also talk about the difference between building clean systems from day one for a new firm versus reverse-engineering legacy environments during private equity due diligence, where the goal is to reduce risk and create long-term value. 

Then we tackle the topic everyone’s wrestling with: AI. Elliot breaks down ethical AI use for CPAs and other regulated professionals, why dumping sensitive client data into consumer tools is dangerous, and why “AI” can sound confident while being completely wrong. He also tells the story of “vibe coding” a purpose-built CRM on a flight, proving that the right-sized tool can beat a bloated platform when you only need a tight workflow that your team will actually use. 

If you care about cybersecurity, compliance, digital transformation, and practical AI strategy, hit play. Subscribe, share this with a founder or operator who’s drowning in tools, and leave us a review so more Charleston business leaders can find the show.

Transcript

Welcome And Sponsors

SPEAKER_01 0:00

Welcome to the Charleston Marketing Podcast, brought to you by the Charleston AMA and broadcasting from our friends at Charleston Media Solutions Studios. Thanks to our awesome sponsors at CMS, we get to chat with the cool folks making waves in Charleston. From business and art to hospitality and tech. These movers and shakers choose to call the low country home. They live here, work here, and make a difference here. So what's their story? Let's find out together.

Meet Elliot Friedman

SPEAKER_00 0:29

Hey guys, welcome to the Charleston Marketing Podcast, powered by the Charleston American Marketing Association. We're coming to you from the Charleston Media Solutions studio. Massive thanks to them for supporting Cama and our show. We also give a big shout out to the South Carolina Research Authority for their annual sponsorship, plus King of Columbus's for jumping on with us in Q1. That's very cool. And a shout out to the Mr. Jerry's Feel Good for the beats at the front of the show. Hey guys, what's up? Stephanie here, Stephanie Barrow of Stephanie Barrow Consulting. I'm excited to be here with my friend Tom.

SPEAKER_03 1:02

Hey there.

SPEAKER_00 1:02

What's going on, Tom? Who do we have in the house tonight?

SPEAKER_03 1:04

We've got Elliot Friedman today. You might recall that we had Tyler Friedman uh as a guest uh a few weeks ago. Yes. Uh the the the tour guide from Walk and Talk Charleston. Well, Elliot has joined us. He's he's the other half of that uh of that power couple. Let me let me read your bio. This is impressive.

SPEAKER_00 1:21

This is impressive bio.

SPEAKER_03 1:22

Absolutely. Uh Elliot is a Charleston-based business and technology advisor, providing holistic advisory support to professional service firms, private equity sponsors, and founders, navigating growth, complexity, and critical inflection points. His work centers on helping leaders make sound decisions across business structure, technology, and execution, particularly where risk, regulation, and long-term value intersect. Across his career, he has held executive leadership roles spanning technology, operations, and digital strategy. He's co-founded a media production company that was acquired in 2014. He later led technology initiatives for growing private equity medical practice or private medical practice, and most recently served as co-founder and chief technology officer of an education technology company through its successful acquisition in 2024. He works with private equity sponsors to assist with risk, scalability, and post-acquisition execution. He works with entrepreneurs and founder-led teams to provide them with guidance. He wrote the book, The Holistic Edge, a private cat uh private capital guide for founders and their professional advisors. And he's married to the fabulous uh uh Tyler Page Wright Friedman from Walk and Talk Charleston, as I mentioned, a former guest here on the Charleston Marketing uh podcast. Elliot, welcome. It's great to have you here.

SPEAKER_00 2:44

Tom out with a mouthful. What an intro!

SPEAKER_02 2:46

You got a lot going on, so it it leads me to believe I just need to do some more editing.

SPEAKER_00 2:51

No, that was impressive.

SPEAKER_03 2:53

There's not a lot of fat on that either, though. That's great. Well, thank you. Love to hear your your origin story, where you're from, where do you study, what led you to Charleston, uh, or if you're from here.

SPEAKER_02 3:04

Uh not from here originally. I'm from what I affectionately call the sixth borough of New York City, Boca Rotone, Florida. I'm familiar. So I I grew up there and um we moved as a family, my my dad, mom, brother, and I to uh a small uh town of about 7,000 people in rural Kentucky called Paris, Kentucky. Um not to be confused with the other Paris, of course. Very different place. Yeah, it's a very different place. Um but you know, the a lot of homage to the uh the revolutionary uh efforts uh that the French helped us out with. So most of Central Kentucky is named after a lot of different um French names. So Paris, Kentucky is in Bourbon County, named after the Bourbon royal family. It's next to Lexnia, Kentucky, which is in Fayette County after the Marquis de Lafayette. And we've got um we call it Versailles, but Versailles, Kentucky. Yes, yes, and then uh you know, went to middle school and high school there and uh had to get the hell out of a small town as a snot nosed dirtbag teenager. Uh one wanted to go somewhere more substantial and ended up at the College of Charleston chasing a um uh a jazz performance uh dream because I was a saxophone player. Wow, not part of my professional CV uh anymore, at least that's what it was.

SPEAKER_00 4:13

I was gonna say, are do you still play?

SPEAKER_02 4:14

I haven't touched a saxophone meaningfully in 10 years. It's uh it's something I I played a lot of you studied with, I think, one of the greatest jazz faculties outside of Berkeley here at the College of Charleston. Uh Quentin Baxter was my um advisor and a uh a dear mentor um for a long time, and of course Robert Lewis and the late Tommy Gill, uh Frank Duvall, all those guys. And so, but I was a dual major jazz performance and uh pre-med, so I'm a med school reject. Um, too stupid to get in medical school. So I my backup plan was computers and healthcare informatics.

SPEAKER_03 4:44

We're glad we're glad that that worked out for you. It probably wasn't so comfortable.

Why Holistic Beats Siloed Decisions

SPEAKER_00 4:50

When I started researching you and I went to your website, holistic business advisor. That is very cool. It's you know, they uh one of our guests uh years ago said the riches were in the niches. And I think that's oh you know Thomas Heath. I oh I do know Thomas Heath. Yes, that is Thomas Heath. He should probably have that on his tombstone. That's what I know him by. Um so that is quite a title. Can you tell us a little bit about that?

SPEAKER_02 5:13

Yeah, so uh my current, you know, um advisory offerings um are kind of a rebirth of uh a consulting work that I did between um I was an IT director for a vascular surgical practice here in Charleston, and then um went out on my own and hung my own shingle as an IT uh consultant for small professional services and medical practices. Um and then I met my former partners with the ed tech company that startup that we did. And so that was seven years of heads down grind it out, bootstrap, raise a little bit of angel money, um, figure out how to scale, survive COVID, and then um you know entertained an unsolicited offer for our uh our eventual acquisition about uh three two years ago now. Um what a blessing. Yeah, it was so look, I've I'm very uh fortunate to have had uh two opportunities to sell the companies that I had helped build. And um so since then I had to kind of relaunch with uh uh an idea and a branding around that. So I chose, I like the word holistic because especially in tech, you have way more than just the stuff that runs on electricity running the business. And so um I had spent a lot of time uh on high with high growth companies between my startups or the um the in the in the medical space. And so the idea was like we have to make sure that every decision we make on one side of the business, we understand how it affects downstream or upstream. And so that's that holistic approach is that no business is just a bunch of different isolated silos, it's everything working in in uh in harmony. And so um I use holistic business advisor as the umbrella term, but below that, uh like you mentioned, I do work with professional service firms as a fractional uh CTO or CIO or chief security officer for their compliance, and then in the private equity world, I work um as a tech advisor helping private equity firms kind of build the value in those companies that they're looking to sell eventually, which is their whole shtick. So the holistic is the umbrella term, and then it kind of trickles down into my um my tech advisory.

Red Flags: Tech Debt And SaaS Bloat

SPEAKER_03 7:04

That's great. So what when you're looking at a company, how can you tell whether they're doing all right or they're headed for trouble?

SPEAKER_02 7:12

A couple of things are dead giveaways. So um I unfortunately I work in the red flag business, and so uh whether it's due diligence identifying red flags and figuring out how to turn them green, um, you know, for depends on the company, but uh, you know, we always look at what is the leadership doing? Are they embracing um, you know, if I obviously I'm tech biased, are they embracing leading edge tech solutions to enhance what they're doing for their uh ultimate deliverable? So are they a B2B business? And then, you know, are they leveraging like today? Everybody's using AI, and you know, uh, we're also making sure are they um wrapping things around in a good cybersecurity envelope too? Because you have to protect your your company, your investment from all of the um evolving threats that we have. But uh, you know, the more direct answer to the question is is how are they using tech? Are they using tech as a uh an unfortunate expense line item for them? Um are they embracing tech? Are they using too much of it? So a lot of the work I do is decreasing SaaS bloat. So uh software as a service bloat where you have 10 different platforms that all do the same thing, but you're paying those licenses anyway.

SPEAKER_00 8:16

So it's kind of like the streaming services apps where they just get rid of it. Love it.

SPEAKER_02 8:20

Exactly. So, you know, looking to see are the you know, are they using the technology efficiently? Is the technology touching all of the company? Um does the operator understand the technology? It's one thing to say, you know, and and and I'll uh I'll I'll give a big shout out to um Stanfiel Gray, who was on the podcast a few weeks ago. And so he uses that ask uh who not how. Yes. And so um, if I don't hear uh operators asking who not how, then I realize that they're trying to do it all themselves. And um there's a there's a lot that you can do on your own, especially from the tech side. And I do have clients that like to kind of be the first decision maker on their tech, and then they come to me when it doesn't work or they can't figure it out or whatever. Um, but you know, I'm I want to know is the operator willing, is it are they coachable or are they willing to see, you know, the bigger picture, that holistic lens? And um it's not always about revenue because you can be making plenty of money and scaling, but um, if there's a lot of room for improvement and you're not aware of it, then I think you know it's a little bit of a red flag where you don't realize that you have a ton of baggage, we call it tech debt, uh, that you're dragging along with your company. So um those are kind of the filters I look at.

SPEAKER_00 9:25

So when you what is the process? So someone brings you on board and they come into their business, do you meet with all the employees? How what does the process look like?

SPEAKER_02 9:32

I mostly work day to day with really small operations and in the professional services, and those are attorneys, CPAs, you know, medical um uh physician or or uh practition-owned uh companies. So the teams are relatively small. And that's both a great and a bad thing because you know everybody wears a 50 different hats. And so um and I had that same experience, you know, in in in the in the private medical uh practice where you know I joined a team of about 13 people and we ended up growing to over 50 people and then expanding throughout the state. Um but you know, because I was dealing with IT, kind of if if it was powered by electricity, it became my problem. So I had to also wear the hat of a lot of the digital marketing, and I'd had this media production background, and we were doing, you know, short form videos. Um I love that. So working with uh you know, working with operators and their teams and and I come in ideally, I come in when people are just launching. That's why I like to work with founders. That's why I like to work with a professional service person like a CPA or an attorney leaving their law firm uh that they've been working for and starting their own law firm. That's an ideal opportunity for me to come in because I can help build everything from the ground up that's gonna support them. We're gonna find the technology that matches their uh the way that they practice law or CPA or or medicine. We're gonna um help get their team trained up on how to use the technology effectively. That way you're not wasting licensed, you know, dollars every month or uh finding yourself, you know, I can't use any of the tech because it's uh it's all too hard or too challenging.

SPEAKER_03 10:54

Yeah, yeah. That seems cleaner rather than dismantling something that is kind of working but but a little bloated, like to use your term, uh while keeping everything running. Is that accurate?

SPEAKER_02 11:06

Absolutely. Now on the on the private equity side, um I work with a uh a larger private equity advisory firm called IT Ally, and we're nationwide, we work with private equity, predominantly in the lower middle market, so private equity buying companies that are typically only three to ten million dollars and EBITA, which is kind of that uh you know that special formula for seeing how their um how their income actually uh works, excluding some of these extraneous factors. But when we come in, we're doing due diligence on the companies that they're looking to buy. So I do a lot of reverse engineering too. Um and that's fun for me because it's a little bit more challenging. It's easier to start with a clean slate and and build uh a tech um system that works from scratch. But when you come in, it gives you the opportunity to identify these uh what we call value creation opportunities. So uh a company using legacy you know software or legacy systems, uh it's working for them, they're making money. Obviously, they're they're good enough for private equity to take a look at them to buy them for millions of dollars. Um but our job is to come in and say, okay, well, maybe they're not at uh market expectations. They're not they don't have a plan for AI, they don't have a plan for cybersecurity, they're not you know using modern um systems that would be working far you know faster and more uh efficiently for them. So that's the value that we can kind of come in and create. So, you know, I do I do the reverse engineering as well. It is a lot more difficult, but it's a lot more rewarding because on the other side of that, you've got teams that are now more agile, you've got companies that are far more value valuable. I mean, that's the goal. Take a company that was worth X dollars the day that our private equity buys it, sell it for six times that five years later. And and tech is a big part of that.

SPEAKER_00 12:38

So when you're coming in with these recommendations, are you also coming in with training and people how to use the systems? Okay.

Compliance And Ethical AI Use

SPEAKER_02 12:44

Yeah, so in each engagement's different. Um, you know, we always tip of the spear is doing the diligence. So that's a single deliverable. We look at a prospective company, write up the diligence report, turn it over to the uh operating partners at the at the firm level for private equity, um, or for you know, in the professional services world, when you, you know, when you want all the things you need to start your firm, your a lawyer, you need obviously, you know, cybersecurity, you want to be compliant. Compliance is the world that I live in deeply. So uh whether it's you know um the Bar Association or HIPAA or the IRS or the SEC, these are all very heavy compliant organizations that force the use of certain technology and force the the safe use of that technology. I just gave a talk to the South Carolina Association of CPAs this week on um the ethical AI use for a CPA. And it's challenging because there's a lot of CPAs dumping their client um financial data into Chat GPT. Wow. I wouldn't have to be. It is terrifying a lot of people are using because we know that the technology is helpful, but we have to use it safely and securely. Um and so there are creative ways now to to use the technology at the same level, but you have to be using the enterprise version, and you want to make sure that you're wrapping it in some sort of um firewall between the the the database that you're dumping into these systems so they don't touch the internet, they don't feed the model, so there's no additional training done. Um there's a lot of uh you know, I I like to say AI is mostly A and very little I because it can't do judgment. And that's when I work with these professionals, that's they're that's what they're getting paid the big bucks for is their judgment. So um you can find a lot of people to crunch numbers with calculators and look at spreadsheets and all that, but it's that ultimate judgment a professional delivers. So I try to support that judgment. And AI can help a professional learn more by doing a lot of research for them. Um I should say they should by doing a lot of research on which sources that the professional should seek out. Um and then, you know, communications, streamlining emails, those are all wonderful things to use AI for. Uh, but you know, if you're plugging a uh tax return in and asking if this is the right deduction amount and all that, AI is gonna lie to you. And AI doesn't know it's lying to you.

SPEAKER_03 14:48

It's going to come up with an answer no matter what.

SPEAKER_02 14:50

It has to be the right answer, but yeah, I like to think of it like when you take a multiple choice quest test, there's five answers to each question. If you don't guess, you're guaranteed to get a zero for that question. But if you guess, you have a 20% chance of just randomly picking the correct answer. Oh, that's right. So when when AI trains, it's it's it's rewarded for at least guessing and not saying I don't know, because I don't know is a zero. Right. And they have a one in five chance in that scenario to get the right answer. So they're gonna put an answer in front of you and they're gonna sound authoritative and they're gonna reference sometimes fake uh sources for where they got that information. So it takes a lot of yeah, right, takes a lot of diligence um if you're using AI to make sure that the information you're getting is good. Uh Tyler and I play this game often because she's a historian and she's got a lot of deep uh knowledge about history. She spends a lot of time researching, and so we'll play the game. We'll ask an LLM, you know, what why is the Pirate House on Church Street called the Pirate House? And it will give you this beautiful story, and none of it is true. That's why she will go, AI is so crappy. I'm like, yeah, I mean it has its downfalls for sure.

SPEAKER_00 15:54

So she's like, I am not a believer.

SPEAKER_02 15:56

She's not a believer, and that's fine. Um, and so I try to bridge that gap. So she would be like an ideal client. She is my ideal client. Um, and so you know, I've helped her in many ways. Uh, I use a lot of AI and building, so I can, you know, essentially they call it vibe coding, but I can essentially direct AI to build custom applications. I do that for a lot of my clients.

Vibe Coding A Custom CRM

SPEAKER_03 16:13

And you did that for the AMA as well, right?

SPEAKER_02 16:15

Oh, yeah. So I uh this was a fun project. Yeah, so I um I I serve on a couple of different boards and committees, and one of them is uh a sponsorship committee. And so uh the the abbreviated version of the story is is uh Tyler and I were flying back from Mexico City a few weeks ago at a wedding, and um I'm working with a couple members on the sponsorship team, and we don't have a we weren't using a CRM, like a proper piece of software to manage all the contacts. Who have we asked for money, who we need to talk to, and all that. And so um, you know, the big players out there, uh HubSpot and Salesforce and all that, they're feature-rich, they're cumbersome, they're kind of ugly, no offense to them, but you know, they're just they're not particularly easy to use. Sure. And um, they cost money and all of these things. So we're getting on the plane, flying back to um to Charlotte, and uh I set up a little virtual private server on my hosting account where I have some website stuff hosted, and I connect my phone um to the uh through an SSH terminal to the uh server and I install Clog Code. So I get on the plane, and for three and a half hours on the plane, connected to Airplane Wi-Fi, I'm texting what I want this CRM or this sponsorship management software to be able to do. We land in Charlotte, I open the laptop, and for the first time I look at what Claude has built me, and it's this beautiful application with all these great rich features. So it's tracking how you know how you use track sponsorship leads. So um it has an AI tool in it. You can chat with the data that you have, you can tell it to you know create Mike Compton as a marketing specialist in my contacts list, and it will automatically do it. You don't have to click new contact, first name Mike, last name Compton. And then yeah, and then it I hooked it up to my email, so it polls my email for specific uh code words. So I use the word sponsorship or deal or progress or anything like that. And it brings those emails in. I can attach those to contacts or attach those to deals in the pipeline for sponsorship asks. Uh so I showed Mike, he says, this is great. I said, Okay, great, I'll make one for AMA. So I rescanned it, you know, white labeled it, all the AMA colors and that was very kind of fun. Yeah, these are very fun things because sponsorships are important. And um, when you go to a big CRM like that, um, like like HubSpot or Salesforce, for example, they have those features, but they're wrapped in 10,000 other features, and you know, you gotta do 50 clicks to get to just the little piece of it that you want to use. So I said, well, we'll just do one specifically. And then that's evolved now into a deal management um thing, and I'm using it for my own deals right now. So when I'm meeting with new clients and perspectives, I can track where I am in the conversation and all my emails are attached appropriately. These are all features that exist in other platforms. I just make it so it's really tight, so I can only see with the information I need to see. Right. And that gives me the unlimited customization. And then the AI component.