Boris from Risk Management Show: Hello, ladies and gentlemen, and welcome to our interview with Jesse Rubenfeld. Jesse is the founder and CEO of FinOptimal, and Jesse and his team sit on the cutting edge of financial technology in the world of accounting and automation software. Jesse, thank you for joining us today.
Jesse: Thank you so much for having me, Boris. I'm excited to be here.
Boris from Risk Management Show: Absolutely, it's my pleasure. So I believe we will have a very thoughtful conversation about the current evolution of accounting and financial operations, and the ways in which automating accounting can allow growing and established businesses to refocus their energy on what really matters.
So Jesse, could you tell us in the beginning a short story about your career path? What brought you to where you are right now and what FinOptimal is?
Jesse:Yes, of course. Thank you, Boris. I'm the founder and CEO of Fin Optimal, which at its core is an accounting automation company.
I'm a CPA and an engineer who started an accounting firm, FinOptimal, as a side hustle. I wrote a lot of automation to grow my business quickly and run it efficiently, and now we're starting to put our software in the hands of other accounting firms who hope to do the same thing. At our core, and at my core, we're really looking to elevate the roles of more accountants the way I did in my own personal journey.
I played and sang a lot of music in college, but I also had dreams of starting and running my own business. Graduating college, I was unsure of what to do next. I was browsing Monster.com and I saw a business analyst position working for the family of companies owned by Mark Gorton, who is best known as the founder of Limewire.
Boris, do you remember Limewire? No, well it was a very, very popular P2P software file sharing. People love to remind me of all the risky viruses circulating P2P file sharing networks to the time everyone was using it. It was one of the biggest software names to college grads at the time. So I would've taken almost any role there.
But I'd done well in accounting and I'd enjoyed it. So I applied. I applied online, which at the time was relatively new. Okay. This was the twilight of expansive bays of resume drop boxes. Anyway, one day I get a phone call from Mark who recruited me personally. I immediately recognized his brilliance and success as an entrepreneur, which is something I aspired to be.
I was thrilled to join a young, clearly ascendant company, and in an office that was just so cutting edge and distinct, there were giant Buddhas and beautiful plants and iron and woodwork throughout the lofty space in Tribeca and a roof deck. And Mark did not sit in a private office. The job held a lot of allure for me.
Once I started though, I immediately realized that most of the job was nothing like my accounting classes. Most of my time was spent doing back office work, paying my dues. It was the the “getting coffee” of accounting, okay. Keying in actual paper vendor bills and then filing them in cabinets. And that element was the bane of my existence.
The gopher part. Go for this. Go for that. Go for coffee. At first, I felt disillusioned, as I'm sure many bright-eyed bushy-tailed college grads probably do a few weeks into their first job. It was a real source of frustration and anxiety. I had more to offer Mark and Liz, the CFO and controller. They trained me to close the books and what to look for in the process.
They would tell me I was the eyes and ears of the finance team. Now - that was the strategic element of my role and it helped me stay the course, okay. Limewire was an unbelievable workplace. Unbelievable. As in, I'd invite our friends to rooftop parties. We would be hanging out in the Moroccan room with hedge fund people, and they'd say “Jesse, I can't believe you work here!” Professionally, though, I still wanted more to elevate my role.
And that started with minimizing the data entry and digging through physical files. I got really creative with Excel and more strategic about how we all worked. People often think that strategy and finance is limited to valuation or deciding when to raise capital or consider M&A, but system and process choices are equally strategic because if you can't measure it, you can't move it or confidently grow by or sell it.
So after six years at Mark's companies, I left to become controller of D.E. Shaw Research, and that's where I really cut my teeth, optimizing accounting I was exposed to and taught myself Python, which allowed me to automate my full-time job down to a few hours a week. And that gave me a ton of time to pursue my music, go to business school, and eventually start FinOptimal as a side hustle.
The frustrations that I felt as a staff accountant early on at Lime and the coding skills I picked up at D.E. Shaw gave birth to the idea of a new kind of accounting firm. FinOptimal was born at the nexus of accounting and tech.
Now I want to wrap up my story with a question. Boris, when you think of accountants, what comes to mind? How would you describe them?
Boris from Risk Management Show: Yeah. The guy in the gray suit with a pen behind his ears sitting and making his calculations.
Jesse: Don't forget a pocket protector.
I remember a colleague referring to us as bean counters. But I was an accountant and an engineer and a performing artist to boost. And when you mix those particular hard skills with a creative mindset in the world FinOptimal is in, you're on a disruptive path in a stagnant industry.
Today we include in our ranks a host of creative artists and musicians, and we're building a culture of excellence and mastery of accounting and engineering.
Boris from Risk Management Show: This is an interesting presentation about yourself, especially from a guy who is working in accounting.
So it's a really mix of both creativity and mathematics. Both brains working very smoothly. So I believe today we will discuss more a topic related to accounting and the risk management. So might be more related to small business owners.
So Jesse, what is bad business posture from your point of view and how can people kind of. From their experience.
Jesse: Yes. Yes. Making bad business choices often leads to worse choices. When you have bad business posture, you lose sight of how you're doing and what matters most. Boris, do you have good posture?
Boris from Risk Management Show: I'm not sure
Jesse: Remember at the beginning of Covid when all of us basically left our jobs and got sent home in a flash? At first we were working on wooden stools, neck bent down towards our laptops, hunkered over the kitchen table, trying to get work done with kids and dogs and significant others, all celebrating our new ever presence.
We let ourselves go a little bit, and it took time to unwind. We had uncomfortable home setups, not meant for the work we were doing. Those tables and chairs weren't designed to stare down at tiny screens and work eight hours a day. So we found ourselves in bad posture. People do this all the time with their businesses and not just in response to business adversity.
It's often in response to growth, and it starts with putting process last. Failing to properly pair systems with people. Business owners have a goal or an idea, and they want to realize that ASAP by any means necessary, maybe it's a new product launch expansion into a new market, or maybe they're just rapidly growing.
They often apply brute force to keep track of their business, meaning having humans work outdated tools just to get it done, forcing an inefficient process around an unfit. They don't stop to think about what products to use and how to use them. They don't think about the marriage of the systems with the process, and I don't blame them.
Okay. Much of business is a race, but it can create bad habits, bad posture. I talk to businesses all the time, some with really bad posture. I remember one that was just trying to make themselves comfy rather than improve their posture. They were on a well known GL and they built a proprietary database that wouldn't integrate with it.
They decided to migrate to a less reliable GL because it could integrate. A few years later, they realized the database isn't as good as off-the-shelf tech, so they scrap it. They spent more money trying to integrate their new system to their gl. They incurred an incredible amount of systems debt because they didn't think about process system pairing.
If they had paused and said, what do we want to accomplish? What are the limitations? And explored them carefully. They could have prevented that mess, but they wanted to try and rush to get comfortable. You can get a cushy chair, but if it's too low, you're still straining your neck. A large client of ours came to us with bad posture and we helped them address it head on.
In this case, their proprietary database was a giant spreadsheet with all their clients and every invoice and receipts since inception. Amazingly enough, the giant spreadsheet wasn't the problem. Okay? It was great. It still is. It's called “$”. That was the name of the file, and it was a very, very cushy chair.
The problem was that it didn't integrate with QuickBooks. In addition to tracking everything in dollar sign, they had to key it into their general ledger and also make a ton of bank transfers by logging into the bank and clicking around endlessly. The chair was too low and they knew it. Invoices would get marked as paid when the money never came in.
You know, they would fat finger amounts, and this would happen to anyone entering the same data into three different systems. And they've paid out the wrong commissions, and sometimes invoices never went out, or receipts weren't recorded. Just reconciling the bank statement was a major monthly challenge.
In this posture, it was hard for them to even try to analyze high level reporting and map out growth. That's a risky proposition if your job is to be the eyes and ears of the finance team and the company.
Now, what's a risk conversation without talking about mitigation? Okay, we helped that client. Of course, seven years later, they're still on “$,” but now, instead of just trying to track their business, they control it tight.
They enter the data once and it flows to all the right places. There are hundreds of large transactions a month, but a person is still in the loop to review and approve them. They're sitting up straight and leaning forward. At the end of the day, it's about finding systems that work with you.
If you feel like you're developing bad posture, stop and ask yourself, what do I need accomplished?
What do I need to know to monitor my business? What am I missing? Talk to your people, the staff, the eyes and ears of your business. Push them to really think why things aren't happening the way they need to and address it. Understand the limitations of your current systems and the pitfalls of your current process.
From there, start your diligence. People are too eager to get comfy, and they don't want to address bad business posture. But at the end of the day, expensive software doesn't fix a broken process, which is the root cause. We've had prospective clients come to us and say they want a dashboard because they don't know how their business is doing.
They're losing sight of what matters. When we dig deep, we always uncover fundamental systems and process issues, and some people just aren't interested in addressing those. They want something flashy, colorful, and modern looking to monitor their business. They think it'll make them comfortable to see it that way, but when you try to get comfortable with bad posture, you lose sight of your business.
When you try to build dashboards for a business with poor systems and process, with data integrity issues, you're really just kind of Photoshopping a dumpster fire.
Boris from Risk Management Show: Yeah. This is kind of very poetic explanation of what you guys doing in the field of accounting.
Jesse: So thank you. I am an artist, after all.
Boris from Risk Management Show: Yeah you see you express your artistic feelings in the many fields of music and accounting/ So I have a question. I would like to ask your personal point of view, what is the commonly held belief as it relates to accounting or business business for, for small businesses say that you strongly or even passionately disagree with?
Jesse: That's a great question. In small business accounting, I think there's still a lot of people out there that yearn for a single system, a sort of monolith that, okay, if I just buy, you know, this general ledger, Then I can put all of my systems on it and everything will just work right to us.
It's much more risky to have a single point of failure to buy a single software package and expect it to address all your business needs. We're more interested in a distributed system with the best in class of each piece of functionality. That's probably the single biggest piece of common knowledge that we try to overturn.
Boris from Risk Management Show: Your main customers are small or medium enterprises?
Jesse: Most of our companies are small enterprises. Think south of a hundred million in dollars of revenue. 250 employees or less people that are gonna be on, are likely to be on QuickBooks online, but maybe are thinking they might be approaching an inflection point where it's time to buy a larger software package.
Boris from Risk Management Show: So this kind of potential customers of yours, what is one thing that they should start to prioritize right now that they are not doing currently? What would it be?
Jesse: I think companies that are doing a lot of double data entry into multiple systems. Companies that are trying to make more out of their QuickBooks experience in terms of reporting, but they're not exactly sure how to do it.
QuickBooks is a very powerful product in the right hands. Hire an accountant to use QuickBooks for you to get the most out of it, to give you what you want in terms of reporting, to give your tax accountant what they need, your auditor if necessary. So typically our prospective clients are looking for more out of QuickBooks than they know how to get.
Boris from Risk Management Show: So where do you think that the accounting as a whole is heading, what are the trends in this space and what should we expect from you guys in the near future?
Jesse: That's a great question, Boris. Because I think there's a lot of, there's a lot of differing opinions here. I think some people think “Wow, AI is just going to automate accounting all the way. Who needs accountants? It's just a bunch of people in gray suits.”
I'm glad I didn't wear a gray suit today. That would've been a huge mistake.
Um, but some people think “wow, accountants are going keep doing the same thing they've always done. It's an important function and they do it well and they're gonna keep doing it.”
We're in the middle, we think the accountants need to change the technology they use, the way they pair systems and people, and we want to empower the accountants to elevate their role so that the gopher roles, even at the entry level, you're more thinking strategically whenever possible, understanding how to connect the process to what really matters to the company.
And so we're trying to put the tools in the hands of the strategic and tactical decision makers so that they can do their jobs. We definitely don't think accounting is going away or getting automated. You definitely need a human in the loop, right? Think of the transactions, the hundreds of transactions, large transactions a month.
You just don't want lots of money flying in and out of the door without a person looking at it. You just want the person to be focused on the money, on the approval, the review, instead of pulling the levers and pressing the buttons and reviewing things that a computer can review and looking up and copying and pasting that, that's where we want to apply the technology, and that's what FinOptimal’s focused on.
Boris from Risk Management Show: All right, fantastic. So if they sum, summarize our interview, if someone who is listening to this interview would like to walk away with one or two major takeaways,
Jesse: I would say think about how your processes pair with your people. Don't look for a single piece of software that ties everything together.
Find the best in class of every piece of the puzzle that matters in your financial operation.
Boris from Risk Management Show: All right, fantastic. Jesse, those were all my questions. Perhaps if I forgot something to ask you that you feel is important, please go ahead.
Jesse: Thank you. Well, if your listeners are interested in how we helped the client that I mentioned and how we might be able to do the same for them, they're invited to set up a free consultation on our website: finoptimal.com.
Or just connect with me, Jesse Rubenfeld on LinkedIn and I'd be happy to tell them more.
Boris from Risk Management Show: Jesse, thank you very much. I hope to speak thank you maybe in the next few months or so to see how things are going.
Jesse: That'd be wonderful. I'd love that.