Scaling Through Constraint: Capital, Cash Flow, and Resilient Execution

Summary

00:00 - Introduction to Lou Rosabianca

02:12 - The Drive Behind Entrepreneurship

04:52 - Growing Up with Immigrant Values

08:01 - Educational Path and Career Beginnings

12:10 - Navigating the Financial Landscape

19:20 - Key Financial Metrics for Small Businesses

22:43 - Resilience Through Challenges

29:42 - Lessons from Business Failures

33:17 - The Role of AI in Business Scaling

36:47 - Future Goals and Aspirations

39:20 - Teaching Work Ethic to the Next Generation

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Full Transcript (AI generated and might include errors)

Jeff Holman (00:01.334)

Welcome back to the breakout CEO everybody. I'm Jeff Holman, your host with intellectual strategies and glad to be back with you guys again today. And I'm really glad that we've got Lou Rosa Bianca. Did I say that right, Lou? Awesome. Got Lou here. I was on the pod, their podcast, Lou and Matt's podcast a while back. And we just had such a good time when I, when I started my podcast, I'm like, man, I need to have these guys on. It'll be a good conversation.

Lou 'The Professor' Rosabianca (00:14.785)

Perfect.

Jeff Holman (00:30.06)

Mostly because you and Matt bring such a good energy and character to the show. But thank you for coming on the show today.

Lou 'The Professor' Rosabianca (00:38.359)

Jeff, thank you for having me. It's easy to have that energy because we like what we do and we're in the small business space. We offer lending and tax credits to the small business, small businesses of America. And it's just a wonderful time to be in this industry because you have to think outside the box. No two days are the same and every day brings a ton of challenges out there and small business is vibrant.

regardless of what you hear and say in the news, American business is thriving and we see it on a daily basis.

Jeff Holman (01:14.776)

Yeah, I love that. you use a different word than I use. You said it's vibrant. I believe that's absolutely true. I like to call it chaotic. And maybe I need to change my my verbiage because I'm like, it's chaos. Yes, it's both. both. It's a full energy chaos. But it's great. And we'll get into some of that because I know you've worked with a lot of businesses. You've grown your own business. You like you've seen and experienced the breakout moments. And I want to get into that with you.

Lou 'The Professor' Rosabianca (01:24.129)

No, no, it's chaotic vibrancy.

Jeff Holman (01:44.63)

Before we go there, I love to ask someone, guess, you know, an initial question to kick things off. And that is you're busy, you're, building your business. You've got, you know, partners, you've got clients, you, got everything outside of business in your life. You know, it's a, it's a lot to carry, especially when you're the CEO of the business or you're, you're in a role that's very demanding. I love to know, you know, what is it that drives you or motivates you from day to day? When you get up in the morning, you know,

Maybe it's what you already said. Maybe it's that vibrant community. But what is it that drives you and motivates you from day to day?

Lou 'The Professor' Rosabianca (02:21.283)

I'd like to come up with some sort of philosophically high-minded notion, but I'm too practical to say that. And I think the core drive for me comes back to my childhood. I'm first generation immigrant parents, and I was raised and inculcated.

with that idea of having to strive and thrive and grow and assimilate and become American and become successful. it was, there was one word that defined our childhood and it was education, right? I scraped my knee, I fell off my bike. Well, did you go to school today? my God, I fell off the slide. I think I broke my arm. How'd you do on the report card?

It was, parents and the grandparents had a one track mind, do well in school.

Jeff Holman (03:19.406)

Yeah, yeah, yeah.

Jeff Holman (03:24.046)

That's so funny. You know, my wife is not an immigrant, but her and her dad is not an immigrant and her, you know, but they have this immigrant mentality and there's a whole story around my wife. You know, I was just mentioning before the show, we went to Europe last year and we actually have connected with family, her family that didn't know she existed, right? So there's this aspect of a connection to people in a different country and it's not immigrant, but when you say that about education,

It reminds me of the first time that I, not the first time I met my father-in-law, but when we let him know, I didn't do things traditionally and go and say, work, you know, could I have your daughter's hand in marriage or whatever? Maybe I should have, but we were there together and we said, hey, John, you know, we're planning to get married. And he just stopped for a moment and he goes, looks at Brooke and he goes, you're going to finish school, right?

It wasn't like, congratulations. was like, school's important. You know that, right? So.

Lou 'The Professor' Rosabianca (04:24.107)

Yeah, can relate. I can relate. I think, Jeff, what happens is for them in their humility, that was the path to success. So it was the path to avoiding the grunt work. It was the path to avoiding the trenches. So I don't think my parents cared whether I went to architecture school or became a CPA or became a lawyer or became a doctor. I don't think they cared. So long as there was some sort of graduate degree involved,

That was going to be my gateway to success.

Jeff Holman (04:57.794)

Well, what was it like growing up then? Did you like, where did you grow up and what were the conditions? And cause cause you're making me think of my father in a lot of like they, grew up poor, quite poor in some ways. You know, he, he was weeding onion fields and throwing a hundred pound sacks of sugar before he was like 12. what was, what was your upbringing like?

Lou 'The Professor' Rosabianca (05:19.107)

Yeah, I grew up in Brooklyn. And I think one of the formative experiences for me is my dad was an immigrant and he came here when he was 22 years old and he still had a strong connection to his family. So every summer, either we would go as a family or he would send me to Sicily for the summers. And I gotta tell you, being a young man and having both sets of grandparents there, not only are you surrounded with love, but you learn work ethic.

Jeff Holman (05:33.902)

Mm-hmm.

Jeff Holman (05:47.661)

Yeah.

Lou 'The Professor' Rosabianca (05:48.707)

because you're on the farm. I mean, I don't care how old you are, you're contributing. So there's, I mean, I remember there was one summer I left like a roly poly kid and I came back like lean and mean and I had like muscles at eight years old. Yeah.

Jeff Holman (06:04.76)

You've been working. That's funny. That's funny. Do you have siblings too? Or did you go over there with siblings or?

Lou 'The Professor' Rosabianca (06:10.463)

Yeah, yeah, I'm the eldest. I have a sister who's three years younger and then I've got a little brother who's 15 years younger. Yeah.

Jeff Holman (06:17.888)

Okay, okay. Did he grow up in the same, with the same mentality or did he have a different upbringing?

Lou 'The Professor' Rosabianca (06:22.259)

No, no, of course not. No, very different. That's the irony, right? Because with immigrants, there comes work ethic, and with work ethic, there comes compound interest. And with compound interest comes success. So the mentality, I was born in 74, right? Is very different than the mentality maybe in the late 80s, early 90s, because then there's a little bit more creature comfort. So maybe we have two TVs in the house and

Jeff Holman (06:35.67)

You

Jeff Holman (06:40.034)

Mm-hmm.

Lou 'The Professor' Rosabianca (06:50.945)

the refrigerator is fuller, so things get relaxed a bit.

Jeff Holman (06:54.597)

Yeah. Yeah. Nope. That makes sense. I was born in 76. I have a brother who, my youngest brother, there were seven of us, he was born in 91. If I'm getting that right, it's 90 or 91. I'd have to stop and do the math. But yeah, he grew up differently than we did. So for sure.

Lou 'The Professor' Rosabianca (07:12.247)

Yeah. And I don't think it's right or wrong. It's just, different. it's, they're both loving paths to the same goal.

Jeff Holman (07:17.399)

yeah.

Jeff Holman (07:23.298)

Yeah, my oldest child and my youngest child might tell you they're right and wrong, but I'm not taking sides.

Lou 'The Professor' Rosabianca (07:29.677)

Well, with my three siblings, it was always the same debate. My two siblings would always call me the golden child and me and my brother would call my sister daddy's little girl. And then me and my brother and then, you know, me and my sister would always call my little brother, you know, the favorite baby, right? So there's always that dynamic with siblings.

Jeff Holman (07:45.9)

Yeah.

Well, and I, you know, my wife is from a Greek family, which is way more Greek than they should be given the, you know, the adoption of her grandmother in the United States and upbringing, you know, here. But they have a ton of Greek DNA to them. And I think if I'm not mistaken, there's some similarities between the Greek DNA and the Italian DNA. Hope I'm not, know, mischaracterizing that, but.

Lou 'The Professor' Rosabianca (08:11.745)

No, is the same except the breaking of the plates at weddings. Everything else is the same.

Jeff Holman (08:17.806)

Yeah, so family is very important. Connection is important and knowing your role, think so. Well, so how did you go from, you know, summers in Sicily, working on the farm to where you're at today? What did that path look like for you?

Lou 'The Professor' Rosabianca (08:39.885)

High school, go to college, I'm a graduate of St. John's University in Jamaica, Queens, also New York. I stayed local throughout. Went to Brooklyn Law School, I'm law school graduate. As you know, I don't practice, but I do lean on that JD. There's something interesting, of course, you're the poster child for that, but there's something interesting that happens to you in law school. You have more of an analytical mind. Besides the reading of the contracts, it's also...

Jeff Holman (08:48.994)

Mm-hmm.

Jeff Holman (08:56.994)

Mm-hmm.

Lou 'The Professor' Rosabianca (09:08.961)

the linear analytical assessment of problem solving, of negotiations, of dynamics. So there's something interesting that happens. I got real deep into the world of real estate, I guess in my 20s and 30s. And that's where Matt and I met because Matt was working for and then became partner at an investment banking firm.

And we would meet in the canyons of the financial district and there was a local watering hole there called Bobby Vans. And I remember the bartender would always say, we're always busy because during good times people need to celebrate and during bad times people need to commiserate. And that's where we met and a lot of deals would happen over the course of a beer or a shot or whatever it may be. And when we formed our podcast, we called it aptly the liquid lunch project.

Jeff Holman (09:52.654)

Yeah.

Lou 'The Professor' Rosabianca (10:06.199)

because it was an homage to those days where more deals happened over the course of a drink than in a Zoom room. And Jeff, frankly, I don't know which is right. I don't know which is wrong, but the romantic in me tends to think that that bar restaurant setting is a bit more apt for warm negotiations.

Jeff Holman (10:14.211)

Yeah.

Jeff Holman (10:28.398)

Yeah, no, I wish we... I don't drink necessarily, so I don't find myself in bars very often, but if we could sit down face to face somewhere for a bit, that would be fantastic.

Lou 'The Professor' Rosabianca (10:38.017)

Well, Jeff, this was my troubling dynamic, right? Because I played soccer and I played soccer competitively probably up until I was 30. So the idea of drinking for me was foreign. I am not jeopardizing my performance, so I am not drinking. So these guys were all on their third, fourth rounds and then they realized, is that a ginger ale? I think it gave me a slight competitive edge by fourth round and negotiating.

Jeff Holman (10:41.378)

huh.

Jeff Holman (10:46.115)

okay.

Jeff Holman (10:57.11)

Jeff Holman (11:04.769)

Yeah, that's funny. you still play by chance?

Lou 'The Professor' Rosabianca (11:08.565)

I do not. tore my ACL years ago and I probably see myself playing with my son, he's two years old now, so we'll run around at some point, but playing competitively is not. I've leaned more on cycling and tennis. It's less of a strain on the knees, believe it or not.

Jeff Holman (11:26.946)

Yeah, nope, I've done a little cycling, but I play tennis and soccer about three days a week each right now. They're my go-to sports. So I played soccer this morning. It's friendly, I didn't hurt anybody and I didn't get injured, so it was a fantastic success.

Lou 'The Professor' Rosabianca (11:33.25)

Awesome fun.

Lou 'The Professor' Rosabianca (11:36.973)

Great, how'd you do?

Lou 'The Professor' Rosabianca (11:45.203)

that's an ideal scenario. So if you could play in a championship game, what position would you play?

Jeff Holman (11:54.362)

you know, I'm I'm naturally a defender, so I I play in the back. My foot skills are not there. They're developing because we're playing a lot of futsal now, but yeah, it's it's fun. So I've gotten way more skills now than I ever had as a, you know, a 17 year old kid. But I'd be a defender still. You put me in that position. I just I can't run too far outdoors or maybe too fast outdoors because I will.

Lou 'The Professor' Rosabianca (11:57.741)

Okay.

Lou 'The Professor' Rosabianca (12:06.729)

smart. Yeah.

Jeff Holman (12:24.238)

pull my hamstring without a doubt. If I gotta chase somebody down.

Lou 'The Professor' Rosabianca (12:26.467)

Who are you rooting for next year's World Cup? If you have a team that you're...

Jeff Holman (12:30.87)

that's a great question. you know, I am a very, very, very casual fan of sports. there's tennis on or soccer on, I'll probably watch it, but I don't have a whole lot of rooting going on.

Lou 'The Professor' Rosabianca (12:43.721)

Okay, so we'll root for USA by default.

Jeff Holman (12:48.012)

Let's do that. If USA is playing, I will definitely root for them. I just don't know who's playing. So I was trying to avoid giving that away, but you know, called me in on it. So, well, so now you're doing the Liquid Lunch Project podcast for your business. Tell me more about your business that you run and it's you and Matt, and you have a larger team with you too, right?

Lou 'The Professor' Rosabianca (13:13.847)

Yeah, so Matt and I are principals and I'm blessed to have a great partner in Matthew. Matthew Meehan has, as I mentioned earlier, he's got an illustrious Wall Street background. So he brought the investment banking expertise to the business. I brought more of the operational, analytical side and together we formed Shield Advisory Group. Now, clients tend to come to us for strategic purposes, whether they're acquiring a business or they're looking to expand or...

They're looking to franchise and that one tool they always seem to lean on is working capital now working capital in 2025 has become an art form more than a science, right? So Let's get away from the big box shops, right? Because the big box shops are like one or two trick ponies They either have a line of credit and when I say big box It's the JP Morgan's the Wells Fargo's the TD banks like the big boxes that these are basically

Cash banks, all they wanna do is give you back your money at a four point margin. The reality is a client who needs working capital is better served with a more curated product that meets their needs. So for example, if you're in the construction field, you probably need some project financing to help you achieve that orbital thrust when the project is only paying you

on 120 or 150 day terms. There's no reason to park a 20 year term loan on the books when you only need financing for four or five months. If you have a manufacturing company, you probably need a factor because that'll kick in once the deliverables start hitting, right? So it's a matter of curating the needs of the business that match the cashflow. And then that tends to create loyalty because you're highly respecting the business's cashflow.

and that service vis-a-vis that loan product.

Jeff Holman (15:14.958)

Yeah. And who do, are those the type of companies that you, that you typically see? Just the, you know, kind of every day's and.

Lou 'The Professor' Rosabianca (15:20.385)

You would never hear the typical small business owner would never know about these products. mean, that's why we exist. We serve as that advisor liaison to try to find, like, I was just telling you earlier in the green room, like we went to a conference last week just to meet more of these hybrid lenders. Like you want these alternative solutions out there. I've come to the conclusion, Jeff, and it's an unfortunate one, that big banks

do not like small business. One, it's not very profitable and they tend to have a high rate of default or failure. Take those two elements and suddenly it's not a very attractive product. I'd rather give a credit card out or rather give a line of credit. It's a bit more secure.

Jeff Holman (16:10.936)

Yeah, line of credit backed by your own money.

Lou 'The Professor' Rosabianca (16:14.901)

Exactly, it's exactly right.

Jeff Holman (16:17.922)

Yes. Yeah, I've got a good friend who's just bought a business and structuring that, you know, pretty simple business, but every business has its intricacies. And he would call me be like, hey, do you know somebody for this? Or I need to, I'm working on this right now and I'm running into these problems. And you know, he's an attorney, he's a smart guy, but still navigating the financing side of it. I imagine it's a lot easier if you've got millions of dollars sitting around to do that. But for those of us.

Lou 'The Professor' Rosabianca (16:44.193)

No, but Jeff also, don't think it's like intelligence and IQ has no relation here. There's no correlation between I'm a smart guy and I could find better solutions. It's almost like saying you and I could not design your office, right? You need an interior designer. One, she or he may have some experience and they have more outlets and more.

experience in finding different solutions. Like maybe a longer conference room is better than an oval conference room. Experience has showed them that and also they are exposed to all these vendors that are constantly selling them. And the same thing with us. We're speaking to these lenders and there are new creative products coming out all day long. So when we find something that's really powerful, that would help small business, man, we add it to our arsenal and then we talk to our clients.

Part of that is also training our advisory team because the better knowledge they have about these products, the better that we can serve our clients.

Jeff Holman (17:53.516)

Yeah, that all makes sense. And how do you guys get the word out about this? Because that's, I mean, that was his issue. He's like, I've talked to this bank, I've talked to that bank. I need to find more people who have more solutions. And so I put them in touch with an independent broker, or I put them in touch with somebody I've done banking with, or, you know, I probably, if I had known, would put them in touch with you guys at the time.

Lou 'The Professor' Rosabianca (18:08.141)

Yeah.

Lou 'The Professor' Rosabianca (18:12.503)

You got to got to you know, unfortunately, you got got to you got to knock on a lot of doors, right? I mean, look at us. We have a we have a weekly newsletter that comes out every Friday on Substack the weekly. We do our weekly podcast that we were blessed to have you on as a wonderful guest. one of our favorite episodes. We do email marketing. We have a call center. Like there's no end. You know, we go to marketing events. We go to expos. We go to conventions. You do anything to get the word out. So yeah, I don't think there's

one solution. Like if you would have asked me that question maybe eight to 10 years ago, I'd say, it's Facebook ads and Google, you know, Gmail, It's email marketing. I think those tactics are antiquated at this point, right? It's all bots and spam. So you have to kind of think outside the box today.

Jeff Holman (19:03.726)

Yeah, and I'm sure that your newsletter and your podcast are helping kind of with that omnichannel approach to marketing. But that's one of the things that's always stumped me as I work with startups and smaller scaling companies. And some of these are investor-backed companies. I think that really the value to investors oftentimes isn't just the money. That can be helpful or hurtful sometimes.

But it's the network that they bring to it because they're in that game all day long and they can connect you with the right people at the right times. Whereas main street shops, mom and pop shops may not have the same network access, right? So plugging into people in the financing world and the legal world oftentimes is where they turn to.

Lou 'The Professor' Rosabianca (19:48.045)

Jeff, you're right. And part of it is educating them, right? Like sometimes when you're working with a startup, you're putting those documents and protocols in place to allow them to scale, whether it's intellectual property, whether it's copyright, you're allowing them to scale. And with us, how many times do we have conversations and say, well, look, this won't work today. However, over the course of the near future, respect these protocols.

Jeff Holman (19:53.464)

Yeah.

Lou 'The Professor' Rosabianca (20:16.819)

and undertake these tasks and you'll be in a great position come Q1 or Q2. So it could also be there's nothing available today, but you're right around the corner.

Jeff Holman (20:27.596)

Yeah, I'm curious to ask you because you deal with so many companies, like, because I've been thinking about this in part as I was working with my friend on some stuff and in this business purchase, but also in my own small business that I run as a law firm and, you know, other other clients I run with. What do you think that are the three, two or three or four metrics or characteristics that every small business owner needs to be managing? You know, is it profit and loss? Is it cash flow? Is it?

something else. What are those things?

Lou 'The Professor' Rosabianca (20:59.885)

I think it's real-time accountancy. So you need to be able to generate a profit and loss within a week or two. Like if I ask a business owner to generate a year-to-date profit and loss and it's dated August 31st, that's not a true metric, because so much could have happened in those two and a half months, right? So you need real-time accountancy. Besides real-time accountancy, you also need to measure cashflow. Like how much do you need coming in the door

and then respect that with accounts receivable. And another thing is I have a tough time with companies that do a lot of work on a timetable, whether it's 90 days, 120 days, 180 days, because you're basically financing that work. And the one thing that business owners don't take into account, you laid out a lot of labor and maybe even materials to be able to do that work and you're not getting paid for 120 days.

There's a cost of that labor, there's a cost of that capital. Excuse me. And usually the pricing doesn't take that into account, right? So it's just understanding what it costs to open your doors every morning.

Jeff Holman (22:12.526)

And that's interesting that you put that in terms of pricing. I mean, that is fundamentally a pricing issue. You've got to get the price right to cover the costs. Otherwise, you've got a cost problem that you've to deal with. what tools are...

Lou 'The Professor' Rosabianca (22:24.503)

The trades are notorious for not estimating properly nor billing properly. Because you're dealing with that human element. If that job required three visits instead of two and you only estimate it for two, well, there goes the profit margin.

Jeff Holman (22:34.935)

Yeah.

Jeff Holman (22:46.53)

Yeah, believe me, I know as a law firm where labor is the number one cost in the business, it's the same issue. So what are the tools that you see people using to deal with these factors? Real-time accountancy, cashflow, cost management, are there tools out there that you're seeing that are commonly used? Because I think when I talk to people, I'm like, you don't know what cashflow is. You're not managed or, you know.

Lou 'The Professor' Rosabianca (22:48.214)

You

Lou 'The Professor' Rosabianca (22:52.461)

Sure.

Lou 'The Professor' Rosabianca (23:13.667)

The tools don't matter. The tools do not matter at all. It's the data entry, right? So whether you use QuickBooks or whether you use Salesforce, there's so many wonderful programs out there today. Look, in 2025, a small business owner has a plethora of tools at his or her disposal that are, I don't wanna say free, but very, very user-friendly pricing, okay? It's a matter of the data entry. Why would a principal...

Jeff Holman (23:17.72)

Okay.

Jeff Holman (23:38.253)

Yeah.

Lou 'The Professor' Rosabianca (23:43.149)

who's responsible probably for sales and management. Dedicate four, five, six hours a week for data entry on bookkeeping. Hire a bookkeeper. No, but they've got that myopic mentality where no one can do it as well as I can. Of course they can.

Jeff Holman (23:58.51)

Yes, they can. They can do it better and cheaper and faster. So, well, I'm curious to kind of turn the conversation a little bit because, and maybe either from the framework of the businesses you've worked with or your own business journey, you know, I'd love to explore maybe some of these moments in your business where it was those, no, gotcha moments or,

Lou 'The Professor' Rosabianca (24:02.998)

Exactly.

Jeff Holman (24:23.288)

can't believe that worked or I didn't realize this, but once I figured it out, it really changed the business. Really the breakout moments in your journey. Have you had some of those along the way?

Lou 'The Professor' Rosabianca (24:33.251)

Yeah, but all out of necessity and 911 mode. I mean, we're pretty close in age, right? So we're children of the 70s, which means we've made enough mistakes to know what works, right? And I had my offices and businesses in Manhattan for years before I moved out to the suburbs. So you're victim of 911. On 9-12,

Jeff Holman (24:40.449)

Yeah.

Jeff Holman (24:50.243)

Yeah.

Lou 'The Professor' Rosabianca (25:01.389)

We thought we were out of business and we were for a few months. Now in hindsight, there's clarity. But at the time when you're walking through six inches of rubble, you don't know when you're going to reopen and your mind starts playing games with you. mean, do I close? Do I move? And you start going through this assessment and then, you know, everything, the dust settles proverbially and physically and then you move on. And then there's the economic crisis of 2006, 2007 and

Jeff Holman (25:20.291)

Mm-hmm.

Lou 'The Professor' Rosabianca (25:31.043)

and you start all over again. And then again, I'm making this conversation very New York specific, because that's where I was located. And then we had Superstorm Sandy. And don't forget, Manhattan is an island, and the island was flooded, and everything came to a standstill. Everything was halted for months. And you go through that same assessment. And then we go through the recession, and then we go through the pandemic again. So your mind almost develops this business callous.

Jeff Holman (25:59.586)

Mm-hmm.

Lou 'The Professor' Rosabianca (26:00.611)

the callous of business and knowing to take a punch and I guess a boxer has a better chin after 20 fights than after this first fight, right? You kind of learn to take a punch a little bit better. And I think a business owner must by definition be resilient. And I don't mean resilient where you let the stress roll off your shoulder. I mean resilient in knowing how to pivot.

I'll give you a perfect example. When the pandemic started, and I looked at each other and every bank was closed. Every bank across the nation was closed. mean, there was online banking, but nobody was underwriting loans because they didn't know how long this was going to last. Like, what's the debt service like? If the business is closed, how can they service the debt? So banks were closed. So we looked at each other like, what do we do? And then we started realizing the government was promoting all these tax credits. We said, well, you know what? Let's start offering tax credits. But what do we know about tax credits?

Jeff Holman (26:55.532)

Hmm.

Lou 'The Professor' Rosabianca (26:59.075)

So we took a big chance. We partnered with some accounting firms and we started offering our small business clients tax credits. And we thought it was a linear ancillary product. It was congruent to what we were offering. It was a tool for small business. And we did that for a couple of years and it kept the doors open for us. And thank God we had that insight. And then once everything reopened, now we have an additional revenue stream. Wow, this is great.

Jeff Holman (27:28.782)

What did that take to... Yeah, what did that take to... I mean, because you're right. These are all moments and some are New York specific and some are global and other people have other, you know, regional specific issues that they've dealt with.

Lou 'The Professor' Rosabianca (27:29.165)

They give you lemons, you make lemonade.

Lou 'The Professor' Rosabianca (27:44.013)

Now, fortunately for us, the ERTC, the R &D, the WOTC, the WOTC, these were all national programs. So it fit within our marketing funnels and our outreach. And it resonated because you basically put liquidity in clients' pockets that they didn't have the wherewithal to achieve or even know how it worked.

Jeff Holman (28:08.824)

But those are still, those aren't small undertakings, right? You've got to, you've fortunately got the platform, you've got the kind of machine in place, but you know, I've talked to a friend of mine who's in banking, a small regional bank, and he helped build out their program, and it did wonderfully for them over time, but I know how hard he worked at it. Like what went into that to build, or another...

Lou 'The Professor' Rosabianca (28:22.253)

Yes.

Jeff Holman (28:36.408)

thing like that, what goes into that from your team to build a new service offering? Because on the outside, just see, you know, we see other businesses.

Lou 'The Professor' Rosabianca (28:44.003)

It's all hands on deck 24-7 for a couple of weeks, right? Because you have to build out the flow. You've got to stress the flow. You have to work out all the kinks. And ideally, you do a soft launch, right? Just to kind of have maybe 10, 12, 20 pilot clients just stress the system to see what works and what doesn't work. But then ultimately, you have to execute. And you have to train your team literally overnight on new products. And that's not easy.

What's the alternative? The close up shop? That's why I mean there's gotta be resilience, right? There's something dangerous about a group that has nothing to lose, right? Let's go for it.

Jeff Holman (29:25.666)

Yeah, yeah. Were you guys in that situation do you think? I mean did it feel that way to you when the pandemic hit? It was, was, was, we, we pivot or, or we...

Lou 'The Professor' Rosabianca (29:35.511)

Yeah, because no one's coming to the office. You couldn't open the office legitimately and nobody wanted to work. So you had to learn to work remotely and there were no meetings. Now that I think about it, at the time there were a lot of these small business networking groups and associations that flourished in Florida and Texas.

Jeff Holman (30:00.898)

Mm-hmm.

Lou 'The Professor' Rosabianca (30:05.763)

COVID adverse states. And I don't think it's any surprise that those states ended up blossoming thereafter because they were most business friendly during the pandemic.

Jeff Holman (30:17.102)

Yeah, no, I remember our law firm, had, prior to that pandemic, we'd said, hey, let's structure everything so that we can work in a distributed way if we wanted to. We had an office, most of the people came into it, but when COVID hit, we just stopped going to the office. We worked from home. We did all the same things we'd been doing. And I'd talk to clients, I'm like, how are you doing? And some of our clients, it's just devastating to them, right?

just impacted everything that they do on a day-to-day basis. And then people would ask me, how are you handling it? I'm like, I don't tell me people this right now in the moment because it's kind of the exact same as it was prior to the pandemic for us because we had put the infrastructure in place to work remotely. A lot of our clients are distributed already, the nature of a lot of the law that we do, there's a lot of federal practice. so it was easy to, we just didn't

Lou 'The Professor' Rosabianca (31:05.773)

Very smart.

Jeff Holman (31:16.098)

go to the office anymore and eventually got rid of the office. But, you know, I felt bad a little bit in a weird way. like, don't want to promote to the world how easy this has been for us because I know it hasn't been for everybody else. And the shakeup and, you know, just the disruption and resilience was on everybody's mind there. So.

Lou 'The Professor' Rosabianca (31:38.923)

But I don't think that was luck on your part because you put the wheels in motion to be lucky. You saw or you or your partner saw that there was an alternative to that brick and mortar. mean, the problem with the service space pre-pandemic was it was so top heavy because you needed a lot of real estate and you had heavy wages. Right. So you just eliminated 50 percent of that equation. Kudos to you.

Jeff Holman (32:02.658)

Yeah, yeah, no, it's, mean, I think it's not for everybody. And I talked to owners and business owners, you know, I talked to somebody just last week, they run a 300 person business, they're adding another 80 this next year. And he said, we just, we're in office, or I don't know if you call it in office or office first, that's just how they operate. that's.

Lou 'The Professor' Rosabianca (32:24.119)

Those corner offices with a view and mahogany walls are pretty expensive.

Jeff Holman (32:29.134)

They can be, yes. Yeah. Well, so what are some of the insights that you've taken away from these moments where you're running into these issues? Because I know it's not, we always see the backside of it, right? Or I don't know if it's the front side. We always see the end result. And it's like, that worked out. We probably wouldn't be talking about stuff if your business wasn't.

going right now because you you probably wouldn't be out there saying, well, look at everything that didn't work out for me, right? So it's easy to hear all the good stuff.

Lou 'The Professor' Rosabianca (33:04.097)

You know, I think the biggest takeaway and the biggest lesson learned there is to just start. People are obsessed and business owners fall into this category. We are obsessed with getting things perfect. Let the market define perfect. So maybe the flow has five steps instead of four, or maybe that platform is a little tech amateurish. It's okay.

You'll get there, right? Because something happens with the market. The market has a visceral reaction to whatever you're offering. And if it works, just double down and evolve with the process. Like I'm certain that the Coca-Cola product today wasn't the same as it was 100 years ago, right? The viscosity was probably different. The ingredients are different. The important thing was just start it.

Jeff Holman (33:58.126)

How does, and you've got a background in strategy, right? You like to be, I think I read on your website between you and Matthew, you know, you got funding and you got strategy. Do you think that comes into play in the way that you approach problems? I mean, do you and Matthew approach problems? You're coming at it with the same objectives, but do you come at it from the same angles or do you guys come at things differently?

Lou 'The Professor' Rosabianca (34:20.279)

This is, I'm certain you've heard this in the past, the terms, Matthew is the visionary. He comes up with an idea and then I need a couple hours to figure out if I can execute on that idea. And then sometimes I say, Matt, that is asinine. This is never going to work. But sometimes you'll have these ideas like, wow, I can scale that, right? Because how do you scale any product or service? Break it down to its umpteenth degree and then times it by 10.

Jeff Holman (34:26.861)

huh.

Jeff Holman (34:33.422)

You

Lou 'The Professor' Rosabianca (34:51.233)

If you break every task down to its minute detail, then it's easier to understand and then you could scale that.

Jeff Holman (35:10.466)

I think I dropped for just a moment there. You were just talking about breaking things down. So we'll cut that part out. You want to start over on that? Breaking things down?

Lou 'The Professor' Rosabianca (35:18.541)

Well, you know what, just make a note of this time sent, this time, 3520. The good thing is Riverside records locally, so you'll hear everything I said on my side, and then guess your edit team can play with it a little bit. Yeah. Okay.

Jeff Holman (35:31.778)

Sounds good. If you finish that thought, we'll just start off there. you guys, so it's, I mean, you've really simplified scaling. Do you see companies doing it that way? Are they scaling that simply or are they trying to make it more complicated?

Lou 'The Professor' Rosabianca (35:48.707)

I think that is the aspiration of AI, because if AI can help you...

expand and multiply your efforts. I don't think the key to AI is, I have one person doing administrative work, let me fire that person or replace with AI. I think the hope for AI is that you'd be able to scale at such an accelerated pace and such an expansive manner that it becomes a game changer. So now you're able to punch way above your weight.

Jeff Holman (36:26.382)

I haven't thought of it that way, but I think you're right, right? AI is, I don't know, I've used a lot of AI in different ways and I'm trying to think if I've used it successfully to expand on something more than simplified. I think what I do is I use it to simplify, even if simplifying is getting the framework in place before expanding into, before adding my thoughts on things.

and going outward from there.

Lou 'The Professor' Rosabianca (36:56.163)

But Jeff, AI lacks judgment. So you may use, in your field, you may use AI to help you with the legal research and you can help it pull some cases for you and just to see what prior cases said on that topic. But at the end of the day, it's your judgment that's going to help you decide which path to take or how to advise your client. So I think it's almost as if AI will help you

Jeff Holman (37:00.387)

Yeah.

Jeff Holman (37:05.206)

Right.

Lou 'The Professor' Rosabianca (37:25.673)

organize your ingredients. But at the of the day, you have to execute on the cooking.

Jeff Holman (37:28.748)

Yeah.

Jeff Holman (37:32.502)

and judge whether or not it tastes good, So, well, this has been fantastic. I really appreciate your time here. Can we do a couple of quick questions? You were telling me that you did an episode on your podcast with some insights from the last year. Maybe we could add a few quick questions, types of, type of interactions here. You open to that? All right. So I'm going to start off with the easy one. You know, do you have a, do you have a favorite book?

Lou 'The Professor' Rosabianca (37:34.529)

Yeah.

Lou 'The Professor' Rosabianca (37:54.819)

All right, tis the season, let's do it. Let's have some fun.

Jeff Holman (38:03.008)

Is that an easy one?

Lou 'The Professor' Rosabianca (38:03.055)

boy, yeah, you know what? I'm a big Ayn Rand fan. I love Ayn Rand. so whether it's the fountainhead or, think I'm just a voracious capitalist. And the way she's able to explain the free market mentality just resonates with me. Just keep your...

Jeff Holman (38:20.675)

Mm-hmm.

Jeff Holman (38:31.864)

Okay.

Lou 'The Professor' Rosabianca (38:32.973)

Keep your eyes out of my bedroom, your hands out of my pocket, and let the market decide what works and what doesn't work.

Jeff Holman (38:40.268)

Yeah, so on that note, what has worked this year for you? What's something where you're like, hey, we really nailed that?

Lou 'The Professor' Rosabianca (38:47.413)

Huh, interesting in 2025.

I think we did a really good job in improving our technology internally, right? Not just inter-office communications, because we have advisors and team members everywhere, all over the place. So being able to smoothly interact and share documents and share communications with everyone has always been a challenge. We've gotten much better and focused on that.

Jeff Holman (39:08.621)

Mm-hmm.

Lou 'The Professor' Rosabianca (39:20.067)

in 25. And it's 100 % the success of our team, not Matt and I.

Jeff Holman (39:26.798)

Okay, yeah, team is huge there. And so if that's worked well in 2025, what's something you want to do with your business in 2026? Are you scaling? Are you optimizing? you cost cutting? What are you doing in 2026?

Lou 'The Professor' Rosabianca (39:40.055)

We wanna put fuel on the fire, right? The systems and processes are working, communication is working, our underwriting is working, the flows are working. We've got some wonderful dynamic lending partners. We just wanna pour a lot of fuel on our fire.

Jeff Holman (39:57.324)

Okay, is fuel funding or fuel just more of this, you've nailed it now, you're scaling it, is that what it is? Or what is the fuel for you?

Lou 'The Professor' Rosabianca (40:06.817)

No, yeah, so scaling for us means a couple things. One, more advisors. The more people we can speak to, the more business owners we can assist. Two, we have a lot of success with strategic affiliate partners. Affiliate partners by CFOs, CPAs.

Big box banks, believe it or not, big box banks like us because they love to issue denials and declines and someone's garbage is another person's treasure and we make hay.

Jeff Holman (40:32.504)

Okay.

Jeff Holman (40:41.144)

Right.

They do a service by giving somebody a referral to you guys after they tell them no.

Lou 'The Professor' Rosabianca (40:47.487)

Exactly. Yeah. And we make them look good because they maintain the banking relationship, but they get the working capital that they needed. I mean, just because you have a 650 FICO doesn't mean you don't have a wonderful business.

Jeff Holman (41:00.974)

Okay.

Lou 'The Professor' Rosabianca (41:01.068)

And the other theme is to try to go up market just a little bit, right? Just working with larger firms and larger enterprises.

Jeff Holman (41:14.722)

What size of deals or firms does that equate to?

Lou 'The Professor' Rosabianca (41:19.075)

Basically the same client base, just larger in scope. So if our target audience today is two to 25 million, we want to focus on that two to 40, 45 million.

Jeff Holman (41:23.447)

Okay.

Jeff Holman (41:31.982)

Okay, yeah. And that way you'll see maybe more deals or bigger deals along the way.

Lou 'The Professor' Rosabianca (41:39.095)

Yep, yep, because something tends to happen with inertia. That one to three year mark for businesses, you tend to have more failures. But once you get that forward momentum, it's easier for businesses to scale. They figured out the systems and processes, they figured out their products, their services. So it's easier to scale at that point.

Jeff Holman (42:05.198)

Yeah. Okay. My last question is this, and I usually ask what are some tips for scaling CEOs, but I'm to go a different direction with this based on the conversation we've had. In addition to the importance of education, what is one lesson you'd like to teach your two-year-old, you said, right, in the next five years?

Lou 'The Professor' Rosabianca (42:26.306)

Yes.

Lou 'The Professor' Rosabianca (42:29.761)

wow, what a wonderful question.

I think the one thing I could teach James, my son, at a young age is work ethic because left to his own devices.

Someone can outsmart you and someone can out strategize you. But if you decide, you can outwork everyone.

Jeff Holman (43:05.579)

Yeah. Time to get a farm, I think, or send them to Sicily.

Lou 'The Professor' Rosabianca (43:08.963)

No hope I hope not for his sake I hope not for his sake I gotta figure out an easier way

Jeff Holman (43:17.294)

I don't know, it's tough to learn more work ethic than on a farm, I believe.

Lou 'The Professor' Rosabianca (43:20.707)

Yeah, I think you're right,

Jeff Holman (43:23.832)

Well, Lou, this has been fantastic. I really appreciate you spending some time with me. It's been good to reconnect since we spoke last on your podcast and really glad that you've been willing to share some insights with our audience here on The Breakout CEO. So thank you so much for joining us.

Lou 'The Professor' Rosabianca (43:38.509)

Jeff, we thank you and we love, love, love your firm. We love your platform. I can't express enough how important it is for small businesses to get their legal house in order. And traditionally, you'd have a very expensive retainer with an hourglass being turned over and you've been able to crack the code and make legal services accessible to the masses. So thank you for what you do to small business community. It's tremendous.

Jeff Holman (44:06.412)

that's very nice of you. I'm just trying to follow the footsteps in the past of people like you who have also, they're catering to the same community, they're building, and you're making things accessible that need to be accessible. And, you know, my view is not to go off on a soapbox here, but you kind of open it up. You know, every small business needs to, you know, validate their product, validate their market, and then protect the freedom to operate their business. And that's where you and I come in, right? Legal.

finance, the other administrative, maybe less sexy parts of the business that are there to make sure the business can run, operate, grow without failing legally, without failing financially. So I think we're doing the same good work.

Lou 'The Professor' Rosabianca (44:49.603)

Jeff, will say the same thing in a much less eloquent fashion. Let the candlestick maker make candles, let the shoemaker shine shoes, let the mechanic work on cars, right? Leave all the administrative muck to firms like us. We'll handle it for de minimis cost.

Jeff Holman (44:54.67)

No.

Jeff Holman (45:10.318)

That's right. Yep. Let the business owners go and do the thing that they wanted to do in the first place that they thought was running a business and selling stuff and making some money. So, Lou, thank you again. Tell Matthew hi for me. And to all of you guys who joined us here today on this episode, thank you. Feel free to leave a review if you enjoyed this podcast. Send guests and send listeners our way. We love building.

up the community of startups and scaling CEOs and glad you joined us again and we'll see you again next episode.

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