Industry Spotlight: Former Showrunner Turned Financial Planner

"Industry Spotlight" is our newsletter series where we interview professionals from across the entertainment industry about their current jobs and career trajectories. Our hope is that you will learn more about the positions you're already interested in, discover new roles you may not have considered, and utilize the wisdom of those who've paved the way before you to forge your own path for success. 

We sat down with Matt Fleckenstein, a former showrunner who now has his own financial planning practice partnered with Northwestern Mutual.

HOLLYWOOD RESUMES: Tell us about yourself. Where have you worked previously, and what are you doing now?
Matt Fleckenstein: Well, big nutshell, I grew up in Buffalo, graduated from Syracuse Newhouse School, moved out to LA and started schlepping coffees and driving scripts around town. I was lucky enough to enter the industry at a time when there was still a “ladder” you could climb. My “big break” was getting hired as a PA on Family Guy. I was eventually promoted to EP's Assistant, then Writers’ Assistant which led to my first freelance TV script. From there, I was able to land an agent and lock down my first full-time writing gig at Nickelodeon. Then things just ran from there. I worked for 20 years as a writer, producer and ultimately showrunner, largely in Kids’ & Family TV. It was a great run…until it wasn’t. So, in January 2024, I made a pivot into insurance and found my way into Financial Planning.
 
HR: What made you decide to pivot into financial advising?
MF: As we all know, the industry has changed fundamentally in the last 5-8 years. At the height of my career, I was producing 24-30 episodes of TV per year. The last show I created, it took 2.5 years to make and launch 10 episodes. The financial disparity between those two examples has just made the industry, for me, at this stage of my life, no longer viable. I have 2 kids in college and 3 more on the way. I needed a more reliably solid financial base for my family.

HR: What are the steps you took to make a career transition?
MF: The thing that helped me the most, hands-down, was to accept that the industry had changed so much and was never “going back” to what it was. It was a bit of a justification, an “it’s not me, it’s the industry” mentality, but it helped me feel less like a “failure” and more like someone who had built a lot of experience but no longer had a place to put it. This mental shift was huge.

I then thought about actors and how they ALWAYS have a day job. When a gig comes up, the go do it for a few days, weeks, etc. then go back to their day job. It was another helpful reframe because, for TV writers, the industry has become more about quick gigs than long-term jobs. So, this helped me position writing as a side hustle that was still there if I wanted it to be.

Once I got past all the mental junk, I thought about what marketable skills I have. I didn’t want another writing job. At all. I love writing and will write for the rest of my life, but I didn’t want to rely on it anymore for a paycheck. So, after a lot of thinking, I realized the other skill all writers have is sales. We sell ourselves, our ideas, our jokes, our scripts every single day. If you’re a writer and don’t think you’re a salesperson, you’re absolutely wrong. So, once I landed on the very broad tent of sales, that pointed me in a direction and gave me a focus.

I had spent the previous 5 years involved in a project to build soundstages in Buffalo, where I grew up. That project exposed me to a lot of different things, including a type of insurance called surety. Surety is bonding for construction projects, and I happened to have a friend who was working in surety. It was the strongest lead I had, so I took it. I got my Property & Casualty insurance license and my friend became my Surety Sherpa, introducing me to colleagues and ultimately helping me land a job working freelance for a bonding company. It was a steep learning curve, but I found people who were willing to teach me, so I dove in. However, as I scoured Indeed every day for full-time surety jobs, I found the harsh reality that employers wanted the 20-something fresh out of school. It became very clear I needed to find a career where my life experience was a value add.

So, every day while I was searching for full-time surety jobs online, I would get ads to apply to be a financial planner. I skipped over them routinely because financial planning was just not something I had any interest in. Or so I thought…one day, feeling frustrated and increasingly desperate to find something, I just decided to apply to two companies for financial planning. Within the hour, they both emailed asking to set an interview. In those interviews, I learned what the job actually was and realized it was a perfect fit for me. I got several offers and ultimately partnered with Northwestern Mutual because of the philosophy and soul of the company. And I’m so glad I did.

HR: What's your day-to-day like at Northwestern Mutual?
MF: Honestly, it’s 99% the exact same as it was as a working writer. I was very pleasantly surprised that the workflow was what I had been doing for 20 years. I spend the bulk of my day reconnecting with old friends/colleagues, networking, setting up “pitch” calls then prepping and ultimately “pitching.” But instead of TV series, I’m talking to people about things that are significantly more important and impactful to their lives.

HR: What are the skills you use from your entertainment background to succeed in your current role?
MF: I always said I wished I could get paid to talk with people and help them. That’s exactly what I do now, every single day. My mentor at Northwestern, who majored in finance, says, if she could go back, she would be a communications major. So, the two biggest skills that translate to this career are being comfortable talking with people and being able to present ideas in a clear, engaging way. I’ve come to realize these are the two greatest skills for success in any career, and they’re skills most people in the entertainment industry utilize every day.

HR: Do you still work in entertainment in any way? 
MF: So, I still have a comedy series in development at Sony. Obviously, I would love for the show to find a buyer, but I also don’t have to stress about whether or not it does. I can focus on growing my financial planning company and then figure out next steps if the show does move forward. Statistically, it won’t, so to not freak out every day, obsessively checking my email for any update, has been amazing for my mental health.

One of the great side effects of this pivot is that it has freed me up to write things because I want to write them, not because I think they’ll sell. I still write almost every day, but without the pressure of turning it into a paycheck. I still have reps and relationships in the industry, so if I have a script or a pitch I want to take out, I can still do that. But I get to do it when the right situation presents itself.

HR: How has your perspective as someone who's worked in the industry impacted your approach as a financial planner?
MF: I’ve found through my own experience and talking with friends and colleagues in the industry that no one ever talks to us about any kind of financial planning. We all know there’s some kind of pension when we retire and maybe some health insurance, too, but that’s it. Working in the entertainment industry is such an unstable career that it’s difficult to think long-term. If your focus is on “where’s my next job/paycheck coming from,” it’s impossible to think 5, 10, 20 years into the future. So, my main goal is to get people in the industry to realize they can build a solid financial foundation while navigating an unstable career.

Northwestern Mutual’s philosophy is that financial planning has to be tailored to the specific needs and goals of each client(s). So, when I work with clients, we talk about every aspect of their lives, careers, their hopes and dreams for the future, and then build a unique financial plan and recommendations based around what they tell us is important to them. Naturally, that means different things to different people. It may mean re-positioning saved up cash to help grow for retirement, shifting focus to college savings, ensuring income is replaced if they physically can’t work anymore, etc. I take a holistic view of my clients’ lives and ensure my team and I are guiding them to where they want to be.

HR: Do you have any money management tips for entertainment professionals navigating uncertainty or currently looking for work?
MF: I would never give targeted advice without talking to someone and seeing what’s important to them, but there are some very broad things I think people should keep in mind.

The biggest thing I tell friends and clients in the industry is to build up at least 6 months of savings. We all know there are long gaps in work, so having savings to bridge those gaps is critical. BUT – and here’s the harder part -- don’t be upset when you’re not working and you have to spend that savings. That’s what you saved it for! Spending your savings doesn’t feel like a win, but it actually is because it means you made a plan and stuck to it and you’ve bought yourself time to get to your next job.

The other thing is, do some digging into your pension plan. Depending on your age, you may be able to start drawing your pension early and then even pause the payments when you start working again. Each union is different, but it’s worth the time to dig through their site or even set up a call with a representative who can walk you through your options.

HR: Do you have any money management tips for freelancers? Specifically, how can freelancers who don't typically have access to benefits like 401Ks save for the future, while making sure they have enough financial security to hold them over between gigs?
MF: The biggest change we need in the entertainment industry is education. There’s no reason a freelancer can’t be saving for their retirement. My main goal in my career is to change the mindset of people in the industry and put talking and thinking about financial stability front-and-center. Whether you’re freelance or salaried, 20 or 60, you need to make thinking about your financial stability part of your routine. The industry is always going to be unstable, so you need to create a way to make it as stable as possible for you and your family. And financial planning does that.

There’s a basic barometer out there in financial planning. Undoubtedly, some of your readers have heard it before, it’s not anything I made up, but it’s the 60/20/20 rule. While it’s not tailored financial planning, it gives you guide rails to follow. The rule says whatever income you’re bringing in, allocate (roughly) 60% of it to your daily life (rent/mortgage, bills, food, etc.), 20% of it to savings (building up that rainy day fund) and 20% of it to planning (retirement accounts, insurances, etc.). I teach my kids to think of their paychecks that way and allocate as much toward each of those percentages as they can. Some months it’s easy, some months it’s hard, but at least you have guide rails keeping you focused on your goals.

For the short answer to your question, there are a number of retirement accounts anyone can open and fund, whether with a planner or on their own, right now. It’s not difficult to do. And if someone has an S-Corp, an LLC, a sole proprietorship, etc. that opens additional avenues to save for your future.

All of us, whether in the entertainment industry or not, need to stop confusing financial planning with wealth management. Everyone has a doctor they go to each year for a check-up, everyone should have a financial advisor they talk to at least once a year for a financial check-up. It’s that simple.
 
Thanks, Matt! For more information, please visit: http://mattfleckenstein.nm.com