Over the last 12 years, Jason Hershman led financial planning & analysis at successful, hyper-growth companies in the sports arena.
But his career started as a ballboy at the Philadelphia Eagles. It was a job he spent months pursuing at 14 years old. This experience taught Jason a key lesson. He says: “things that seem out of touch, out of reach are not, it just takes a little hustle, a little effort.”
This attitude has stayed with him as he has led multiple finance teams and embarked on everything from redesigning the chart of accounts, owning the month-end close, building financial models from scratch, raising millions in equity, renegotiated debt, to IPOs.
Finance highlights included leading the $400 million sale of Appetize, a B2B SaaS business in the sports industry (Appetize is the software provider for all of the MLB, NFL, NBA, NHL stadiums as well as theme parks such as Six Flags, Disney, and SeaWorld). After this, Jason launched his own fractional CFO business, Point FP&A, providing FP&A to some of the most exciting companies in the sports industry. He has the luxury of turning down clients who are not in the sports world.
In this episode:
- The Philadelphia Eagles as a ballboy for 5 years – things that are out of touch are not
- Learning accounting and FP&A on the job in my first online retail startup in New York – which eventually became public
- Getting hired at sports startup Appetize (B2B SaaS)- combining my passions for sports and finance + getting to exits
- The power of rebuilding a financial model as central to my career
- Going to market as a sports FP&A fractional CFO at Point The ideal balance and differences between accountancy and FP&A
- Secrets to rebuilding the financial model
- Being honest on my journey with AI and FP&A
Connect with Jason on LinkedIn: https://www.linkedin.com/in/jasonahershman/
Check out Point at www.pointfpa.com
Glenn Hopper:
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This is FP& Today. Welcome to FP&A Today, I’m your host, Glenn Hopper. Our guest today is Jason Hershman, a seasoned finance leader and entrepreneur. With over 15 years of experience driving growth and strategic success in hypergrowth companies, Jason’s career spans an impressive array of accomplishments, including leading a $400 million sale of Appetize, A B2B SaaS business in the sports industry, spearheading IPO initiatives, raising and renegotiating millions in funding and integrating acquisitions seamlessly. But beyond transactions, Jason sees himself as an operator where he uses finance to manage companies to their potential. Following the 400 million sale of Appetize, Jason left to start his own fractional CFO business. He now works exclusively with startups in the broader sports industry and is the operating CFO to a number of exciting businesses in the space spanning sports, media, startup leagues, beverages, software, and others. He loves being part of the broader fractional CFO community and wants to inspire those who have a finance background to apply their finance skills to things that light them up. Jason, welcome to the show.
Jason Hershman:
Good. Thanks for having me. Wow, what an intro that might, <laugh> might be the kindest thing anyone’s ever said about me, <laugh>.
Glenn Hopper:
I I was, it’s funny, I was talking the other day, like, I like to go on podcasts just to hear people say nice things about me. You know, <laugh>, it just, it’s an ego boost immediately. <laugh>. Yeah, that was incredible. I, I did love the last bit there about applying finance skills to things that light them up. And we talked before the show, and we’re gonna, we’re gonna get into this, but finding the ability to do that early in your career is such a, an amazing thing. If, I mean, you know, everybody listens to the show. We all love our, you know, finance and building models and doing all that, but if you’re doing it in a cause or a business or an industry that you love, it just makes it that much better
Jason Hershman:
For sure. It, it’s part of your identity, who you work with, and if that aligns with who you are, whether you’re creating the product or doing finance for the product, I think makes all the difference. And in my experience, a lot of finance people feel kind of like trapped, like they have to do finance, they have to do accounting. When without realizing that every company in the world, the companies that they love the most, the products that they wear, use, talk about all need, finance and accounting. It took me a little bit to figure that out, and I’m hoping to, uh, kind of shine the light on that and share that with others and encourage them to do the same.
Glenn Hopper:
And what I love that you said yesterday before the show when we were talking, is that you will turn down, if somebody comes to you that’s not in your wheelhouse of where you wanna focus in your fractional CFO business, you’re not taking that kind of business because you’re, you know exactly where you wanna be working. And I think that’s, that’s great and that to have the discipline, ’cause you know, you could do it in other areas, but it would probably take the fun out and you’d lose some of that passion.
Jason Hershman:
Yeah, for sure. You know, I talk to my wife about this all the time. <laugh>, uh, you know, it’s a privileged place to be, to kind of like pass leads off to other fractional CFOs. But, you know, part of the reason I’m doing this and why I’m out on my own is to build something that I wanna build, that I wanna be a part of that, you know, gives me excitement, doesn’t drain me. And there’s a lot of priorities outside of money that are important to me. And I’m, I like to think long term. Um, so maybe in the moment it stings a little bit, but I know that if I stay disciplined, consistent, I can build something that, you know, I’m proud to be a part of, proud to say that’s mine and proud to work in on a daily basis. And like I said, you know, aligns with who I am and lights me up, gets me excited, and that’s just what I gotta do and that’s why I’m out on my own a little bit <laugh>.
Glenn Hopper:
Yeah. Love it. Well, I, I guess let’s dive in because I wanna walk through your career journey to how you got where you are now. And I, uh, something that was very interesting, and I don’t, maybe not even related to the rest of your career, but can you walk us through your career journey? And I wanna go back to your time with the Philadelphia Eagles all the way to now where you’ve founded Point, and I guess, you know, within that kind of how you ended up moving into FP&A from that. But, and you, you might say, oh, the Eagles don’t have anything to do with it, but I still wanna <laugh>, I wanna hear the, I wanna hear the background all the way back to that, if you
Jason Hershman:
Don’t mind. Yeah, yeah, no, absolutely. It’s definitely like the coolest part, <laugh> of my career, I would say, you know, growing up in the Philly area, you know, the Eagles are everything, but, you know, as I, as I reflect on it, it actually had a huge kind of impact on how I go about my career. And let me explain. When I got that job, I was maybe 14 years old and my parents told me, Hey, you’re gonna be in high school. You know, I was going into freshman year in high school, and they’re like, you gotta get a job this summer. You can’t do anything or you can’t just do nothing. And my thought was, okay, well, I don’t wanna just do anything. All I wanna do is work for the Philadelphia Eagles. And this is early two thousands. You know, LinkedIn wasn’t a thing, Facebook was like, didn’t exist.
You couldn’t just Google anyone or get in touch with anyone. And I kind of just like hacked the internet a little. And I found one phone number to call the Philadelphia Eagles. And sure enough, it was like a receptionist in some random department. And I must have called this lady every day for six months until eventually she forwarded me, you know, three months in, she forwarded me to the equipment manager three months after calling the equipment manager every single day he brought me in, he said, Hey, you want a job <laugh>? I said, yes. He’s like, how about you be a ball boy, you’ll live with us for the summer. You know, that’s when they did training camp kind of away from Philadelphia and you’ll come to games and work the games and work the weekends. And I held that job for four or five years and it was amazing.
And I loved it. I loved every moment of it. And how that has impacted me in my career and specifically what I’m doing as a fractional CFO is like, I just, you know, from a very young age learned that like things that are seemingly un out of touch, outta reach are not, it just takes a little hustle, a little effort. You know, I apply that kind of like rigor to when I’m trying to go work with a specific company or get in touch with a specific person. And it’s been very foundational and it has put me in positions, situations, interacting with people that, you know, maybe, maybe someone who hasn’t had that like Philadelphia Eagle experience would think is not even possible. And now I just look at every opportunity as well. That’s possible. I just gotta put in the dedication, the consistency, and the effort. And so it actually has had a very, like, meaningful impact on my career.
Glenn Hopper:
That’s great. That’s great. I <laugh>, I’m just picturing you finding this number, dialing it in, and then, you know, someone picking up the phone. Mrs Donovan. This
Jason Hershman:
Is, yeah, exactly. Yeah, no, we had house phones and I remember when we like finally got the job offer, I wasn’t at the house. My mom picked up our house phone and I didn’t find out until my mom told me when I got home. So, uh, yeah, different times. And, um, that’s how it worked. I, you know, you say that I had Jevon Kearse as my voicemail and all my high school buddies would just call me all the time <laugh> and get upset with me when I would answer and not, you know, my voicemail. So <laugh>.
Glenn Hopper:
That’s awesome. Yeah, I mean, it sounds like you’ve had an idea and a focus and a kind of out of the box thinking and a drive early on so that that sets the stage. So now walk me through post-college Yeah, your career there.
Jason Hershman:
So, okay, so sure. Studied finance and supply chain management in college, and I did some finance internships. Your typical internships worked at JP Morgan. Truthfully, I did not love my internships. And so it was a very sexy time to be an investment banker. That’s all anyone wanted to do. You know, Michael Lewis’s books were blowing up, the, the financial crisis happened in 08 and we were all like, you know, starting to graduate college and people were just like obsessed with the investment bankers. And I felt like the oddball not having interned there and not wanting to do that. And so I wanted to find a way where I finance and supply chain management to my actual career. And I was looking for something smaller, something where I felt like I like actually understood what I was doing and the impact that was having. This is when like, Facebook was blowing up, Google was blowing up.
There wasn’t like this like startup culture, like startups weren’t, you know, a thing that people tried to find. And so I found this company on Craigslist that was doing the international e-commerce for every US retailer, and they were hiring their first finance guy in New York City. And I was like, oh, New York City, I want, that’s where I wanna move after college. <laugh>, this thing is e-commerce. So you buy things online, um, they ship it to you, that’s supply chain and they’re hiring a finance person. So I applied it was a one room startup, got the job, and uh, it was just like a huge learning curve for the first six months. So I, I got the job started and the reason I got the job was ’cause I wanted to avoid investment banking. And I ended up working investment banking hours anyway for a lot less money, but it was very, very educational.
Like I learned the intricacies of accounting. I did all, I set up all the accounting, all the financial operations. There was no like cloud software, so it was a homegrown accounting system. I had to do journal entries, I had to work with the engineers to make sure our systems were capturing transactions correctly, everything set up the accounting. And after like six months, I became the expert on the numbers and the results. And people started asking me how we did and why. And I started explaining things and then I started saying like, here’s what we might expect next month, next quarter, next year. And I started putting together all this in Excel. And before I knew it, I was like learning Excel and building financial model was talking to the CFO and CEO every day. And without even realizing it, I kind of started understanding fp and a and through the experience of one, getting the expertise in the accounting and the numbers.
Two, the influence with fp and a and three, watching this company grow, I kind of like really got a firsthand seat on the power that finance can bring to a young growing business. And I would say like, Hey, here’s what we need to change in our pricing, or here’s what we need to change in our product. Or let’s go get partnerships with this carrier in Japan to lower our costs so we can increase our sales. And I started like using finance to really just like kind of manage the company to its success and lead initiatives to its success. And we would implement these changes. And I started measuring the results of the changes. Was that a success or failure? And what we could do to kind of like tweak it. Long story short, you know, this company grew, we acquired businesses, we implemented systems, and eventually we ended up taking it public. So from the very get go at this first job, I kind of got the full span of what finance could do at a startup, and I was hooked. And that’s how I knew, like from there, this was like the career path for me. And also I learned a ton. So I just was armed with this knowledge for the rest of my career. And that has really shaped kind of what I do now, how I run companies, how I think about it, all those things.
Glenn Hopper:
Yeah. And that’s, you and I have a, a very similar background in that because I spent most of my career as a CFO in the startup space. And it’s, you know, I got an MBA and a master’s in finance, but nothing <laugh> you don’t, nothing teaches you like just being in a startup where you have to wear every hat in the company and you have to, there’s no one to pass the buck to, so you have to go figure it out. And I think such a, such a valuable experience and it’s, it makes you, uh, you know, if you’re doing that earlier in your career, you understand not just, you know, technical accounting and, and finance courses. You understand what an income statement is and what a cashflow statement is and all that. But in a startup, while you’re looking at your burn rate and you’re, you know, seeing the impact of all this, you understand, you know, the, the importance of the balance sheet and the cash flow and all that. And it, it just, and then also, oh, by the way, you have to know these systems because we don’t have an IT department yet. And you’ve gotta <laugh>, you know, get everything communicating and talking to each other and running these reports yourself and everything. It’s a, it’s a, it’s a serious learning experience. Yeah.
Jason Hershman:
Like in school, you know, whether undergrad or grad, sure, you learn accounting, you, you probably learn excel, you learn financial models, you learn what a balance sheet is, cashflow statement is. But in this experience, you learn how everything is connected, how those statements quantify pretty much everything that everyone is doing. And the purpose of those statements, why people look at a balance sheet to know that you have this much AP do and you know, this much AR coming in and how they might manage that on a month to month basis. You, you learn like why this number on the P&L is the way it is, and what decisions are reflected in that. And so in that experience, even though you’re doing journal entries, you’re doing financial operations, you’re chasing AR, you learn the importance of it because you know where it’s gonna land on the state financial statements and you know what that all means for the business.
Glenn Hopper:
So you go from the startup, startup goes public, and you move on through your, your, uh, next career stops. How did you go from there? And then, you know, to, to appetize and, and the experiences you had there and, and then ultimately deciding, you know, I’ve done this in a, in a several different companies, I wanna try now this fractional C-F-O-F-P-A fp and a as a service business. How did you kind of evolve into that?
Jason Hershman:
Yeah, let me, let me bring you up to speed here to where I am today. So company went public, was fully vested, longest tenured finance guy at the time, wasn’t really sure what to do next. So I went to business school, got into a really good program at Cornell University, did that. And following business school, I, you know, I’m still young and I, I didn’t really know what I wanted to do. Um, and I got recruited by a Cornell alum to come into a larger consulting firm. He said he was starting up a CFO practice. It’d be very similar to what I did at the startup, except more dollars more people, you know. And quite frankly, he was offering me a lot of money. And I was young, and I figured, all right, this, this actually sounds pretty cool. Um, I did that for four years.
Learned like the model, how to sell yourself as a finance person. I built up a great network of private equity professionals. But after, you know, four years, I, I quickly kind of like realized that I belong in a startup that’s, I’m seeking that opportunity again. At the same time I was getting married, I was done with traveling and didn’t wanna be away every week. And, uh, in my personal life, I was just like working out every day. I’m a big marathon runner, endurance athlete, you know, working for the Philadelphia Eagles, I’m into sports. And I kind of just like, was like, what can I do that’s gonna really excite me where I can also apply my skills? And so I looked for a sports startup that I can work with. And I got hired as the head of finance under a CFO at a B2B SaaS business in the sports industry.
And it was awesome. Uh, <laugh> loved it. And what I did there was I just, you know, kind of ran the same playbook. They had a controller and so I was kind of more on the FP&A side, but I would basically, I rebuilt their financial model. That was the first thing I did. And using the financial model, I kind of started telling, Hey, marketing, we need you to generate this many leads every single month because that’s gonna impact the pipeline in this way. Sales, we need you to close these deals this quarter. So ops, we can get these, you know, we sold to stadiums, we can get these stadiums live and we can start triggering revenue recognition. That’s how this model works. And here’s kind of like the budget for everything and here’s how many hires and all of that. And in the background, for several years, I was kind of running an m and a process.
’cause this was kind of right in the Covid area when stadiums were empty and people were like, wow, you got an awesome business. But like, we don’t know if people are coming back to stadiums. So we were in this m and a process, COVID happened and it kind of just drew it out for, for two years or whatever. Finally the acquisition happens, super successful exit. And at that time, after the exit, I was kind of like, alright, I got this itch to, to do my own thing. The only way I know how to make money is finance for startups, and I kind of wanna stick to the sports and fitness industry. So let me just like go to market as this like CFO and I’m gonna just like specifically target, you know, sports and fitness startups. And sure enough, to my surprise, there was a market for it, <laugh>. And within, you know, six weeks I was kind of off and running, had a number of clients and was just working as their fractional CFO. And that’s what I’ve been doing for the past two years now,
Glenn Hopper:
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You know, I love what just comes naturally to you. You’re much younger than I am, so you haven’t seen this kind of evolution firsthand like I have, but you speak very proactively about the modeling and what you’re seeing. And I think early in my career, the CFO, this is going back to say about the time you were with the Eagles was probably my first finance job. And, um, thinking back then, the CFO role felt very backward looking. And it was just, it was a passive role that was, you tell me what you want, I can do whatever kind of financial report you want. You want ratios, I’ll give you ratios, you want this. And then the rest of the management team would take what the CFO gave them or not believe what the CFO gave them <laugh> and then go to whatever, uh, you know, make their decisions.
But really over the last, we’ll say 20 to 25 years, and it’s, I’ve got a whole tangent I’ll say for another day, but I really think Sarbanes oxley and ENRON and sort of the CFO shifting and having to, uh, you know, sign the financial statements and sometimes be the adult in the room, I really think that this kind of led a lot or maybe accelerated some of the change in the CFO. But when you talk about you’re building the model and what you’re seeing, and then you’re going proactively to, whether it’s sales and marketing or operations or whoever, and telling them, you know, Hey, look, we’ve modeled this out. If you do X, Y, Z, we’re gonna see these results. And I think that that’s where the real value comes. And I think that leads to my next question. What sets point your FP&A agency apart from maybe a traditional provider and offering those high touch fractional CFO services?
Jason Hershman:
That’s a great question. And to be honest, I’m sure there’s like a ton of really good fractional CFO services out, but let me try and answer that question with following your logic a little bit. So I think, and this is a hypothesis of mine, and you could tell me I’m wrong, um, but like when you come up doing studying finance and accounting at a school, you do, I would say 80% of the people think that the only path is, you know, Deloitte, EY, PWC, KPMG investment banking, right? And that, that’s the path. And these are all financial services. These are service providers that are external to companies. And so what they do is they just make sure that the numbers are right. And I think when people like start their career in that path, they kind of just like get so focused, hyper-focused on the numbers.
You tell me and I’ll get you the numbers type thing. Whereas I kind of didn’t, I didn’t go that way. I kind of first like jumped head in and companies were like, we need to know the numbers. And um, you know, it was a little bit of my personality where I’m not great at just like, even like when in my first job was just like sitting there saying like, here’s the information I kind of get, you know, a little too involved <laugh>, which has helped me and hurt me a little bit, but like I was putting together the numbers and I wasn’t gonna do it for no reason. I would say, okay, like, why do you need this for, what do you need this for? And let me help give you the answers to that question. Here’s maybe a solution. That’s my hypothesis on that, like transformational shift, how I might separate myself.
Um, one, I like to tell my clients that you never know that we’re not full-time. I know a lot of fractional CFOs, they’re like, you meet with us once a week, twice a month, whatever it is, I, you know, my service isn’t, isn’t like that. And then similar to what I did at Appetize, what I did at that first company is I, I view finance holistically. And so if I’m building the model, I’m doing it in a way that, oh, like this is gonna be able to track information the way that everyone is talking and thinking about the business. This is gonna be able to answer everyone’s questions and also let me align the GL with that. Let me, like, this is all in harmony, right? So let’s reconfigure the chart of accounts. I’m not just sticking to fp and a, but let me reconfigure the chart of accounts so that we’re tracking everything in the same way that people are discussing about it and making decisions, right?
So people use the products that I’m creating, the p and ls, the forecasts, the models to actually make decisions to refer to it, to, to kind of assess what went right, what went wrong to give the company a valuation, to go out to raise money, to hold people accountable. So it, it’s starting to be that the clients I work with, finance makes sense to them. I’m able to explain it in a way that they think in a way that’s useful. I don’t know if that differentiates me, but that’s one thing that I’m pretty proud of. And then also simultaneously, if the GL is aligned one way, well then sales, your CRMs gotta track, you know, new, new clients in kind of a similar fashion, you know, marketing, you gotta give me the reports in the same way, you know, headcount, we gotta make sure each department is lined up with how we wanna track it and see it in the general ledger. So I’m not just touching finance, I’m coordinating functions across the business to align with how I know that people wanna see information, use information, make decisions. So whether that’s a differentiator or not, that’s just how I, how I run my business. Um, and I think I have good client satisfaction. So <laugh>.
Glenn Hopper:
Yeah. So I a again, I love you saying this and, and I can’t say this everywhere because of the, the groups I talked to, but because we are on FP and A today, not CPA today, I’m gonna go ahead and say this here, we’re <laugh> we’re gonna keep it within the FP&A Today community. But so historically, you know, the path to CFO was CPA audit, big four, you know, go, go through and, and do just the, the very strong accounting focus you are seeing in, in recent years, more and more people coming up through FP&A into the CFO’s seat. And I think I always said as a CFO, I was only as good as my controller is, but I didn’t wanna do any of the work that the controller was doing.
Jason Hershman:
Yeah.
Glenn Hopper:
And you know, I would, if I had to come in and talk to the auditors, it was <laugh>. You know, that was not where I wanted my focus to be. And I never, you know, in very young, in my career, I didn’t want to go get the CPA, I didn’t love the debits and credits of it. I wanted to do the, the modeling and all that. And I think your approach is what the modern CFO is doing. You have to have, you know, depending on the size of the company, you have to have that chief accounting officer and you have to have people that, you know, make sure that your, your base foundational GL is right and accurate. But beyond that, where the CFO’s office brings value, like that’s table stakes and that’s more and more what’s being automated. But where you’re adding value is I’m not just giving you the reports, I’m giving you my strategic insights and that’s where we’re adding value. And it sounds like that’s what you’re doing with point as well. Yeah,
Jason Hershman:
Exactly. Um, I never took the controller role. I do think I’m very good at accounting, but I know that there’s CPAs out there that just like know more than I do. And I have two controllers that work with me that are amazing. And honestly, I probably couldn’t do what I was doing without their support. Now what I like, the way that I assist them is I say like, Hey, here’s, here’s the AP process, here’s, here’s how we’re gonna set it up, here’s what we’re gonna do. Here’s kind of what I need from you. And how they help me is, you know, I’ll say like, Hey, if we wanted to track something this way, is that, like, how would you set that up in the general ledger? And they, they would be more of the expert on like, well, this should be a natural account. This should fall under here.
Lemme go create the account. They would do that stuff. And also if I’m trying to decide is this a cost of sales or is this an opex, is this something that we should amortize or does this just get immediately expensed? They they have really good like insights on the proper treatment of certain things when it’s not so clear. Now, I don’t think you could do the CFO and even probably the FP&A job without some sort of like concrete foundation in accounting. And I, I actually think FP&|A a teaches you a lot of accounting ’cause you kind of start to understand how PE things move through the financial statements. Um, yeah. But it’s for, for sure a different job, a different skillset. And to my point earlier, it’s not a hundred percent necessary if you wanna be the, the CFO to go down that path. And to my point earlier, sometimes it’s, it’s detrimental because of the way it shapes your thinking early on in your career. Yeah. I had a LinkedIn, sorry, I’ll, I’ll stop after this, but I had a LinkedIn post recently where most of my clients come to me because they’re not getting what they need out of their accountant <laugh>. So it’s not that they don’t have accounting, it’s just they need more.
Glenn Hopper:
Yeah. And you know, being in that startup space where you are, it’s funny because I’m, I’m not doing as much fractional CFO work now. I’m, I’m a lot more focused on the, the tech, sort of the FinTech, everything from software systems to an analytics and ai. But most of my fractional CFO clients, because I’d spent so much time, not always in the startup, but in the SMB say under 25 million in annual revenue, that’s where most of my career has been. You know, a couple bigger than that. But <laugh>, I got so many clients that came to me who I would be the first actual finance person they had. These are people who start, you know, who had a tax accountant and was, and then as the business got bigger, they were trying to get their tax accountant to do FP&A for ’em. And the tax accountant, all they’re trying to do is minimize your <laugh> your taxable income. Yeah. And they’re like, I don’t, I, I guess I’ll, I build you a budget. I don’t <laugh>. That’s not what we do.
Jason Hershman:
Yeah, yeah. Tax accountants, they’re trying to like, uh, minimize income. FP&A is trying to tell you how to maximize income. Um, obviously there’s a need for both. Like a really good tax accountant is like a really good resource. But I found traditionally that’s best to outsource and I don’t know, does not fit the CFO role in the same way. Just ’cause again, they’re just so focused on how to minimize taxes and not how to maximize revenue, gross profit, whatever, whatever metric it is that you’re going for.
Glenn Hopper:
Oh, yeah. So many of ’em, and one of ’em just jumps out right now, and this is a a, I won’t go too far down this tangent, but it was a, a company that their tax accountant were, were very good. And every year at the end of the year, they would say, wow, you’re sitting on so much cash, you need to distribute this. You need to prepay this and do all this. And they would dump all the cash outta the business at the end of every year. And then this company renewed their biggest software platform that was half a million or more a year, had to pay an annual like in February after they just dumped all the cash <laugh> Yeah. Outta the business. And it was, and it was, it, it took, you know, you come in and you see things like that. And that’s the difference between, you know, audience here knows, but the difference between the tax accounting and, and FP&A a was how about we look at it this way, may, you know, maybe we can change the contract if you want the cash outta the business at the end of the year, we can do this.
Uh, or we could go to quarterly payments, we could manage the cash flow better. <laugh> Yeah. All that. But,
Jason Hershman:
Uh, yeah, they’re focused on the 1231 deadline, which
Glenn Hopper:
Yeah,
Jason Hershman:
Is some ways a little arbitrary when you’re running a business for multiple years. I get that you gotta report and you gotta file taxes, but it’s not always the best strategy to follow a tax accountant’s advice when operating the business.
Glenn Hopper:
Thinking about operating the business, I, you know, one of our favorite topics here and, and for all fp a people is, is financial modeling. And you said earlier, you know, I, I’ve really hung onto that when you’re talking about when you would model it out and show, you know, that you would have a message to give to sales and marketing and operations or whoever. But let’s take into that a little more and like, how do you approach financial modeling to align it with kind of those strategic goals and inflection points in a business?
Jason Hershman:
I would say the, the most work that goes into a client is like the first 90 days when I’m, I, I like to rebuild the financial model from scratch. And it teaches me a lot about like the business, how the chart of accounts is set up, how people think, make decisions, um, how the business works, how the business makes money. And through that process of like showing people what I’m building, how it looks, feels, how it works, how accurate it is, I just learn about how people wanna see information and what information is actually important. You know, one of the realizations that I came to early on as a fractional CFO is when you’re spread across different businesses, you kind of focus on what matters. <laugh>, when I was doing FP&A for a specific company, I could forecast every single variable, make sure it gets updated with actuals, all that.
But then you start to realize that like maybe those variables aren’t that important and don’t, don’t need to like muddy up the forecast. So you start just having a number of conversations and people start thinking about the business in terms of geography, in terms of product, in terms of variable SKUs, how they price things differently from either one service to the next. And you start just like really understanding, okay, these are the key things and how we should probably set up the P&L and which revenue streams we should use. And then cogs should mirror revenue. And then opex, like which departments, what, what things should we break out in opex that are super critical? And from the P&L you, once you get that, you kind of create an skeleton of a P&L and then you can kind of walk, walk backwards and be like, okay, if I were to forecast this revenue, what would I need to know?
Well, all of these metrics now needs to be broken out by the different revenue streams. And so it just, it just becomes a unifor the model becomes uniform to align with how people need to see the P&L, how people think about the business. And then as you start thinking about how am I gonna update this? How am I gonna pull in actuals based on this way, you start saying, okay, is the general ledger set up to track information in this way? If not, what do we need to change? Do we need to change the chart of accounts? Do we need to make sure that every revenue stream that goes on the books gets, you know, booked with certain attributes? And if so, how do we ensure that in each of the systems? How do we automate that in each of the systems? And then you start thinking, okay, now that I have actual set up for it, how do I get forward looking information based on this?
And you start asking the marketing team, the sales team, Hey, can you design this report in this way in your system so I can use this as a key input? And sure enough, after maybe, you know, six months, the whole company is thinking about everything in the same way, using the same reports that are like filling into the model. And FP&A doesn’t become this aggregate reports, you know, create presentations type thing, but it’s like, Hey, you know, this person’s leaving. We’re we’re filling these roles, you know, this, we just got this in the pipeline. What would happen if this didn’t convert this month? And it becomes just very easy to refresh, tweak, give people answers to operate on different circumstances as things change, to compare it to a budget. It just becomes super simple and also a lot powerful, more powerful. So that’s, I think that answers your question on how I think about building the model and it’s, and its impact on the business.
Glenn Hopper:
Yeah. And you know, what I love is, you know, so there’s that Warren Buffet quote that what, you know, or accounting is the language of business or whatever. So to your point, to do good fp&a, you have to know accounting and then thinking about what we provide, where our value is to the business. I say, uh, you’re, you’re, uh, an FMVA right from CFI. Yeah,
Yeah. I’m, I, I was, I was thinking, I, I am too. And I, it’s funny, I went and got mine way later because I felt I’d been a CFO for years, and I got nervous that, um, I didn’t, I wasn’t spending enough time in Excel, and my team knew so much more about it, so I went back and got that certification later. But it’s, it was a great reminder for me in thinking about like, you know, you’re talking about the impact of, of one transaction or somebody leaving the company or whatever, the impact it has on the model and how it kind of flows through all the financial statements and the impact there. And that’s where the domain expertise is so important. And I think, you know, there’s more and more is automated, and obviously I talk about AI and machine learning and automation all the time, but for, for the time being that kind of domain expertise and that insight that you bring is where finance is gonna add the best value.
And that’s that it’s more than just human in the loop. It is a human at the wheel. You can use all the tools and technology to, you know, to help you with that. And I’m sure, you know, I, we all spend most of our time is in Excel right now. Some of us, yeah, you can do stuff in Python and other platforms, but really the most of the modeling to this day is still done in Excel. And there’s add-ins, you know, like datarails and, and others out there that you can integrate directly into Excel and, and get some more power out of it or, um, you know, power query and, and power Automate and, uh, all the, all the Power BI stuff and everything. I mean, there are new tools, but they’re not gonna go do this work them themselves. And I’m wondering, so you’re working with different clients and I’m sure they have different ERPs, different gls, different CRMs and all that. So you have to kind of be technology agnostic when you come in, in the way you approach ’em. When you come into clients right now, what role does technology, and I mean the, the financial systems, BI tools and all that, what does it play in when you’re doing the modeling or even trying to scale fp and a functions? Like where’s, where is that intersection with technology for you now?
Jason Hershman:
I’m very similar to every, everything you just described, where <laugh>, most of it all comes together in Excel, for better or worse. And I know I need to get better at that, and it’s one of my areas of focus for 2025 is how can I apply software to the whole process of aggregating everything in Excel. Now, what I will say, putting everything into Excel and aggregating it for me is not painful. And here’s what I do, regardless of what general ledger, what CRM, you know, what payroll system I have, I know what the inputs should look like. And I go as far as all these, all these softwares, you can design your own reports in them. So I know every payroll system has last name, first name, title, department, salary, you know, start date, end date. Every payroll system has it. Every GL has account number, account, you know, whatever it is.
So I, I design all those inputs, save them as inputs, and anytime I need to like refresh it, I could just download it, pop it in. And so regardless of what software stack each client’s using, I just gotten really good at knowing what works well as an input and I can use it. The magic, and this is why I like Excel, the magic is like, how are you gonna forecast the P&L? How are you gonna make it look, you know, you can design it, make it look, forecast it any which way you want, and grab those inputs in the same way. So that, that’s kind of like how I approach the technology is like, I have like standardized what inputs look like for different components of the p and l, the balance sheet, whatever. Um, that’s how I approach it.
Glenn Hopper:
I’m sure you kind of have your template and you, and you have where you drop in all your inputs and are you doing like index match or power query, or how are you
Jason Hershman:
Populating
Glenn Hopper:
That
Jason Hershman:
I, I find that if I’m using a complicated formula, I’m not letting the data out correctly. I should not be filtering data in a formula. I should be filtering the input before I grab it. So if I need to grab it from two separate inputs, then that’s on me. I like to keep it simple, keeping it simple in the formulas. Even though I can write complex formulas, I wrote some terrible looking formulas. But the problem is, they’re, they’re hard, hard to follow. Even for advanced people. They’re not easy to update, they’re hard to audit. Um, so I, I am constantly questioning myself. If I’m not using X lookup, SUMIF plus minus divide or multiply, then I need to lay the data out in a different way. Um, and that’s kind of how I try and keep myself in check.
Glenn Hopper:
Yeah, I think about that too. So going back to my days of modeling, thinking about, like, you, you end up with, you know, so many tabs in the spreadsheet, but linking to other spreadsheets and you’re emailing ’em around and somebody breaks a formula on one of ’em, and you’ve got a version control issue. And just, and thinking about how complex, you know, the, the massive nested if statements, <laugh> and crazy things going on that, uh, you know, we, we, when you have a team of a bunch of people who are really good in Excel, it’s almost like you’re trying to, um, you know, outdo each other with how complex your formula is. But then to your point, you have explainability, you have, you know, how, you know, you gotta tell the auditors what you’re doing here and all that. So Yeah, I, I hear what you’re saying.
Jason Hershman:
Yeah. Um, you know, and I don’t, I don’t link workbooks because of that issue. Like, if, if I need to compare to the budget, I take an output of the budget and I put it in my model and it’s a budget tab, and I can link back to that tab in the model. Um, so yeah, I do everything I can to make it stupid simple. I design all the reports in the financial model, so I’m never like every quarter updating this report, it’s just updating as I update the financial model. So try and keep it simple.
Glenn Hopper:
Yeah. Do all the, the groundwork early, and that way you’re just Exactly, yep. You know, one thing that I, I’m wondering, um, and I, and people ask me this all the time, so I always like to get inputs from people, especially in the fractional world where you’re dealing with, uh, you know, multiple clients and multiple software and everything. But are you, I guess the first question, are any of your clients asking about it? Or, or, and, and secondly, are you currently using any kind of AI or machine learning? Do you have a feel for this? Are your clients asking about it? Um, um, do you see, uh, you know, do you have a hint or an idea of how, where you think this might be going for FP&A, the AI and ml? I mean,
Jason Hershman:
Yeah, and this is something I wanna talk to you about. Um, I’m very behind on this. If I’m using ai, I don’t know about it now. Like if I’m using RAMP or QuickBooks and they started implementing AI and it’s made something a little sim, uh, more seamless or simpler, um, then great. Like, that’s awesome. If it’s embedded in the product and it’s like a new feature, and it’s just something like that, I log in, I’m like, oh, this is nice. Then maybe I am using ai, but I’m definitely not purposely using AI to apply to my situations right now. So I’m behind, and maybe you and I can detail some use cases and how we might go about using ai. But in preparation of this meeting, um, specifically for fp and a, I think there is a use case in financial modeling more on saving time and less on removing the individual from it.
So if I were to build a financial model, a lot of the, you know, 90% of it will be the same, like how opex gets spent, how headcount gets done. The difficulty comes in that last 10%, how things get tracked different amongst different companies, amongst different business models. And so I would love for like AI to kind of take a URL, you know, www.company x.com and, you know, identify this company is, you know, a SaaS business and their P&L should probably be set up in this way, and here’s like kind of public information about it. So we can kind of estimate these things or maybe fill in the blanks or maybe not, maybe just create a SaaS template specifically for that company. And I think AI should and could be able to do that. And then I think it’s important for a person, ’cause I haven’t seen AI get good at this, is getting specific, like right now, I could put it in chatFPT write this email for me, but it won’t be specific.
You’ll need to tailor it. So I would love for AI to get that 80% done, a person to improve the model with specificity, right? And design it, give it back to AI and say like, Hey, here’s the model, here’s the GL, here’s other information that you need to know. And maybe even like tell it what to do and produce like kind of results outputs, maybe charts that might be relevant. And so the way I would see AI most immediately in FP&A, and again, I’m not the authority on this, I’d love for you to tell me that this is wrong, right? This is too, uh, ridiculous or too easy, and I’m kind of behind the curve is ai, human ai. And you made a point earlier that I agree with is that human in the loop is critical. Like when I build the model, like I’m learning about the company, I’m able to learn about the company and then leverage my experience, which maybe AI has or doesn’t, but I’m able to combine what I learned with my experience and give good advice, give, you know, opine on good procedures, all that stuff. Um, I would hate for people to think that AI can take this end to end and not spend the right amount of time learning how things work in the company in order to like advise the company properly.
Glenn Hopper:
Yeah. And that’s, you know, what you, uh, what you talk about, this could almost this, this could and maybe should be its own episode of FP&A today, where we talk about very, very specifically, this is how you can use AI in FP&A. But the, the human in the loop right now it’s, I say human in the loop, but really it is the human is driving <laugh> AI is in the loop, but the way that I treat ai, and now you can get it to do some amazing things from Montecarlo simulations to, uh, you know, variance analysis to some, uh, some really good insights to, and forecasting, doing complex, uh, forecasting methods. You can do all this with AI, but it’s not on its own. So everybody’s talking about agents, you know, in, in 2025, and that may happen. But the idea that you just tell AI to do a task like you would a human being, and it goes off and does it and comes back, I, you know, everybody, uh, from from Microsoft to Salesforce, everybody’s talking about these agents.
Nobody has delivered it yet. Technology’s moving quickly. Maybe we will see it. But for right now, I, I treat AI like a very, very bright, but very, very green intern. And to your point on spec specificity, if you, you’re the domain expert, you know what you’re looking for in the knowledge that the AI has, there’s something buried in there. You can get it out of it, but you have to drive it and you have to coax it, and it’s not gonna go do it on its own. And you have to know the pitfalls to keep it from hallucinating and, and be, be, ensure that it gives you, um, correct information. And yeah, honestly, that, that might be a fun episode to do. And we would have to lean into video. We could, we couldn’t do it all just on, on audio, but we’d have to do like a screen share and video, but we could really, um, break it, break it down there. And I, I’d love to go into it more today, but we are, we’re getting close to the end of time and I’ve got a couple more questions that I, I want hit you with that we, we get, um, that we ask everybody. So let’s put a pin in that, and that might be fun. I’d love to have you back and we could figure out a way to do, uh, to do an AI breakdown of, of how it works in FP&A.
Jason Hershman:
Yeah, for sure. That’d be educational for me, and that’s one thing that I look forward to learning from you this year.
Glenn Hopper:
Great. Okay. So let’s go into these, these are a couple questions that we ask all of our guests. And the first is, um, and it’s, you know, we, we dove straight into the professional work, so we always like to touch on the personal side a little bit. So what’s something maybe that, uh, that not many people may, uh, may know about you?
Jason Hershman:
Well, one thing is like, I’m a pretty dedicated marathoner. Um, you know, I’m not like an Olympian, but I’ll run, I ran 2 46 on my last marathon, open a break, two 40 on my next marathon. So when I have a race, I stay pretty dedicated. Um, you know, fitness is a big part of my life, um, competition. I love it. So that’s probably one thing that maybe my current audience doesn’t know about me.
Glenn Hopper:
That’s great. I’m a, I’m a marathoner too. I’ve been a couple years since I did my last one. I’m, I’m getting older and I’m beat up all the time. I’ve had two, two Achilles surgeries at hernia surgery this year. I’m probably getting into too much information on this episode, <laugh>, but I’m, uh, I’m, I’m, I’ve two and
Jason Hershman:
A half every too. So that’s how, you know, you’ve been doing it a while. <laugh>?
Glenn Hopper:
Yeah, <laugh>. I’m doing a half coming up in a, in a few months, and I’m doing a, an Olympic triathlon in May and
Jason Hershman:
Oh, amazing.
Glenn Hopper:
So, which I do what I can, it’s way slow. And my, even at my peak, my, my best marathon I ever did was 3 27. So I wouldn’t even, you were, you were finished and showered and <laugh> and like having lunch by the time I got,
Jason Hershman:
Hey man, teach your own, I love that you’re doing it and would love to do a race with you one day.
Glenn Hopper:
Oh, that’d be a blast. Yeah. Um, I guess, okay, so we could talk about, that’s a whole other episode too, is our, our, uh, endurance sports episode. <laugh>. Yeah. What is your favorite Excel function and why?
Jason Hershman:
Oh, man, I don’t think I can live without SUMIFs it aggregates data. It, you know, if you set up data right away, it can serve as an X lookup. Um, it can count, it can add, you could probably, you know, use it in multiple different ways. And it’s also super easy to understand. So, um, it’s like probably the most powerful, most useful function that I used.
Glenn Hopper:
Love it. Love it. Well, Jason, I don’t say this to all the guests, but I’d honestly, I’d love to have you, uh, back on the show. I, I think maybe doing our AI episode might be something fun we could do. We’ll, we’ll look at doing that at some point, um, in the, in the near future. And, um, I, I love what you’re doing. I, I love your, your focus and, and approach to FP&A and, uh, the passion that you have and the way you’re able to take your business into an industry that you really, uh, really care about. So, uh, kudos on on all of that. Before we let you go, how can our listeners connect with you, learn more about what you’re doing at point and if, uh, any, any of our listeners are in the, uh, uh, sports, sports industry, um, in particular, how can I get in touch with you? Yeah,
Jason Hershman:
Thanks Glen. Thanks for having me. I’d love to come back on, we’re gonna do an AI episode together. Please send me some homework ’cause I gotta get up to speed on this and truthfully, gotta get up to speed on it. So, um, to the extent that you could educate me on all this, I’d love to try some things out and, uh, see where it goes. Um, yeah, appreciate you having me. Would love to come back on if anyone out there spores industry or not wants to follow me the best, the best way is hit me up on LinkedIn. It’s just my name, Jason Hirshman. My business is Point, if you can’t find me, but, um, should be pretty straightforward. I’m kind of out there in the open, so. Yeah,
Glenn Hopper:
We’ll, we’ll put uh, all your contact info in the show notes too, so people will be able to reach out to you. So Jason, thank you so much.
Jason Hershman:
All right. Yeah, thanks for having me. Talk to you later.
