Tiffany Jackman of HOBO Films: 5 Things I Wish Someone Told Me When I First Became a Filmmaker
An Interview With Edward Sylvan
Have multiple skills. I’m really big on knowing how to do multiple things. You don’t want to be a one-trick pony. I can write, shoot, edit and I love teaching. So when the pandemic hit and all shooting stopped, it was my editing that really kept money coming in.
Have multiple streams of income and start early. Film isn’t the only thing I do. I recently got into real estate — my uncle has taught me how to invest in stocks. I also help my family members with their businesses, and I am a film professor. You should always make sure you have multiple ways of making money.
I had the pleasure of interviewing Tiffany Jackman, Head of Film Development at HOBO Films.
Tiffany Jackman has had a love of storytelling from a young age starting while writing skits and plays for her classmates to perform during school assemblies. Playwriting evolved to filmmaking when she bought her first camera at 12 years old and has been a passion ever since. Through the years she has produced commercial campaigns for various Fortune 500 companies while working as a film producer at Grey Worldwide and Omnicom Health Group’s Link 9. She has also directed/produced web series, music videos, short films, three feature films and one TV series. She is an alumnus and current screener/mentor for the Multicultural Advertising Internship Program (MAIP) and a member of New York Women in Film and Television (NYWIFT). When not making films, Tiffany can be found teaching film to the next generation of filmmakers as an Adjunct Professor at The New York City College of Technology. Tiffany loves the thrill of filmmaking and is willing to tackle any project no matter how challenging.
Thank you so much for joining us in this interview series! Our readers would love to get to know you a bit better. Can you tell us a bit of the ‘backstory’ of how you grew up?
I’m the oldest of four girls, born in Queens, New York, to parents who migrated from Guyana. We moved to Atlanta, Georgia, when I was in elementary school and from an early age I showed a passion for storytelling. I used to turn my dolls into TV shows and force my little sisters to watch.
Can you share a story with us about what brought you to this specific career path?
In Atlanta, my sisters and I went to a small Christian private school where each week one class had to perform a play for the rest of the school. I started writing those plays for my classmates but would start to get frustrated when the performances weren’t consistent. One day someone suggested I film it so that when it is done right it will be that way forever. So at 12 years old, I got my first camera and that’s where the magic happened. I applied to NYU and moved back up to NYC. After graduating I took an interesting career path and became an Advertising Producer where I worked on various commercials from beauty to toys to pharmaceuticals. It was a great way to gain experience because since commercials are so short you can do many a year and each one is so different. While in film, you are working on the same thing for months. I met a lot of great people and traveled the world. But my passion was still filmmaking so I would still make movies in my limited “downtime.” I became friends with another producer who had the same passion and we began to work on small projects together. Eventually, he told me that he had an idea for a feature. I loved the concept because it tackled Immigration issues which both him and I could relate to. We made that film using all the advertising favors we could pull and that film made it on to HBO. Since then I did other films in my “downtime” and eventually got to the point where I decided I cannot reach my goals by only doing it part-time, so I left my advertising job. Just as I was leaving, Howard Bowler, the owner of HOBO Audio, who I had been working with for audio on my commercials and films asked if I could help him with his TV pilot, The System. I gladly said yes and I have been working on launching HOBO Films ever since.
Can you share the funniest or most interesting story that occurred to you in the course of your filmmaking career?
The funniest and most embarrassing story has to be when I just started interning at the ad agency Grey Worldwide. Anyone who works in film knows that sometimes you have to pick up the weirdest props. So they were doing a commercial and my boss asked me if I could go find a Blow-Up Doll. Mind you, I was a very sheltered kid, raised in Christian Schools my whole life, so I wanted to crawl in a hole. To top it off, the only places I could think that might have blow-up dolls are those seedy parts of the Village right around NYU, and since I just graduated there was a high risk I would run into someone I knew while coming out of a sex store. So I went and asked the clerk if they could help me. I made sure to tell them that it was for work and they gave me the “Yeah, okay” look. They gave me the blow-up doll and were kind enough to double bag It so that no one would know what it was. I rushed out of there like a bat out of hell and made it back to the office.
Who are some of the most interesting people you have interacted with? What was that like? Do you have any stories?
I’ve worked with lots of people during my time producing commercials and some very talented directors. When I was an assistant producer on Covergirl, they were working with Drew Barrymore and Queen Latifah. I have also met Ice Cube, Gordan Ramsey, Danny Glover. So many people. But honestly, the whole celebrity thing doesn’t phase me. Once you’re on set with people for 10+ hours it doesn’t really matter anymore. All I care about is people being nice and professional since you do have to be on set for so many hours.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
There were some really amazing people at my first job who really took me under their wing and mentored me to be the producer/director I am today. I learned a lot from their production styles. Lori Bullock was such a boss on set, Tricia Bowman was so organized and Rondell Westcott was always so cool under pressure. And now, Howard Bowler, who really has given me the creative freedom to pursue my dream.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
I once heard this Bob Dylan quote about success: “A man is a success if he gets up in the morning and gets to bed at night and in between he does what he wants to do.”
I love that quote because it doesn’t equate success to money. It brings it into you spending your most valuable resource: time doing only things you want to do. Not things you feel you have to do.
I am very interested in diversity in the entertainment industry. Can you share three reasons with our readers about why you think it’s important to have diversity represented in film and television? How can that potentially affect our culture?
Diversity is extremely important in film and television.
- It opens people’s minds to the experiences of people from other cultures.
Film gives us the rare opportunity to peek into someone else’s life. We shouldn’t waste that on seeing the same life story all the time.
2. It helps prevent the perpetuation of stereotypes.
I’ve seen this so many times in advertising where people made 100% avoidable offensive mistakes that would have easily been stopped if they had a person of color in the room to be like “Um no…don’t do that.”
3. It inspires the kid of the next generation to know what is possible.
One of my greatest moments as a film teacher was when one of my students came up to me at the end of the semester and told me that they really enjoyed my class, but what they really loved was seeing a black female producer because it made her feel like she could actually do it too. I swear at that moment I felt like I could retire like I did my job!
What are some of the most interesting or exciting projects you are working on now?
We just launched a documentary titled “Crawford: The Man The South Forgot.” It follows the story of a young woman from Chicago who journeys to a historically racist town to find out what happened to her great-great-grandfather who was one of the richest Black men in the South right after the Civil War and why he met a tragic demise. I’m also writing a TV show which is a modern-day version of All In The Family, but with a Black family and I have a few other projects in the works.
Which aspect of your work makes you most proud? Can you explain or give a story?
When a project is presented to me I always ask myself “Why does this story need to be told?” and “Who can it help?”. I believe that I am blessed to get up every day and follow my dream, but I think with that comes the responsibility to tell the stories of the people who do not get their stories told. My first feature film was about a man who was raised in NYC but gets a deportation notice because he was brought here illegally as a baby. People do not know what it’s like to be in that situation, but the director and I knew it because we grew up in those communities. So, I am proud to be able to speak for the unspoken.
Ok super. Here is the main question of our interview. What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.
- Don’t stress. We’re all just playing pretend.
When I was working in advertising I would often say to the team in stressful situations, “Guys it’s just advertising. Relax.’’ That didn’t always go over well when tensions were high but I was always able to look at the bigger picture. I had much more stressful things going on at home — with my dad being sick since he needed a kidney transplant, or when I would look at my neighbor who is a doctor and out there in life or death situations. It really put the petty office stuff into perspective.
2. Always do your best work because you never know who is watching.
When I was leaving my advertising job Howard Bowler pulled me aside and asked if he could take me to lunch. At that point, I had been contracting his audio company for over 10 years to do the audio work for my commercials and also my films. When we went to lunch he told me how he noticed how hard I worked and how dedicated I was, and since he was an audio guy and not a film guy knew I would do great work on his TV pilot. So that goes to say I had no idea I was essentially “interviewing” for him all those years without realizing it. And that has been the case since I left advertising. I haven’t had to formally interview for anything. Everything is based on recommendations or people remembering me from other projects.
3. Have multiple skills.
I’m really big on knowing how to do multiple things. You don’t want to be a one-trick pony. I can write, shoot, edit and I love teaching. So when the pandemic hit and all shooting stopped, it was my editing that really kept money coming in.
4. Have multiple streams of income and start early.
Film isn’t the only thing I do. I recently got into real estate — my uncle has taught me how to invest in stocks. I also help my family members with their businesses, and I am a film professor. You should always make sure you have multiple ways of making money.
5. Always follow your passion and things will work out.
I know it sounds cliché but it’s true. If you follow your passion you will automatically work harder and be more of a perfectionist in your work. When I was telling people at work that I was leaving my advertising job and not going to another corporate place, but instead following my dream, so many of them told me about the dreams they had. I saw this light in their eyes when they talked about their dream and then the light blew out when they came back to reality. It was so sad. They had reasons for their decisions (had kids to feed, etc.) but they were unhappy. All I can say is that once I left, I just kept pushing and doors opened up for me. Things just kept falling into place and I never had to go back to the corporate world. It’s not easy by any stretch of the imagination. I work harder now than I ever worked in the corporate world, but I am so happy doing what I do.
When you create a film, which stakeholders have the greatest impact on the artistic and cinematic choices you make? Is it the viewers, the critics, the financiers, or your own personal artistic vision? Can you share a story with us or give an example about what you mean?
For me, the story dictates it. As the story progresses you see it in your head and then it’s my job to get it out of my head and in a way that the crew can understand it. I guess that would be considered artistic vision but sometimes I don’t feel like it comes from me but just through me.
You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)
I would love to start a movement of financial independence in minority communities. Where more people of color owned businesses and property in their communities and where they had access to healthy foods and great education. That is why I love the documentary we did, “Crawford: The Man the South Forgot,” because it shows the story of a Black man who was born a slave but became a self-made wealthy man, he owned 427 acres of land and turned that into a successful family farm. It just shows what is possible. I would like my films to be inspiring to start movements and encourage people to make their lives and the lives of their children better.
We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. :-)
So many people — I’d love to meet with Shonda Rhimes or Ava Duvernay, or on the finance side anyone who would love to help Black people open their own businesses in their communities.
How can our readers further follow you online?
You can add me on Facebook under Tiffany Jackman or my Instagram at Tiffyjack85. See some of the work I’m doing at Hobofilms.org or on TiffanyJackman.com
This was very meaningful, thank you so much! We wish you continued success!
About The Interviewer: Growing up in Canada, Edward Sylvan was an unlikely candidate to make a mark on the high-powered film industry based in Hollywood. But as CEO of Sycamore Entertainment Group Inc, (SEGI) Sylvan is among a select group of less than ten Black executives who have founded, own and control a publicly traded company. Now, deeply involved in the movie business, he is providing opportunities for people of color.
In 2020, he was appointed president of the Monaco International Film Festival, and was encouraged to take the festival in a new digital direction.
Raised in Toronto, he attended York University where he studied Economics and Political Science, then went to work in finance on Bay Street, (the city’s equivalent of Wall Street). After years of handling equities trading, film tax credits, options trading and mergers and acquisitions for the film, mining and technology industries, in 2008 he decided to reorient his career fully towards the entertainment business.
With the aim of helping Los Angeles filmmakers of color who were struggling to understand how to raise capital, Sylvan wanted to provide them with ways to finance their creative endeavors.
At Sycamore Entertainment he specializes in print and advertising financing, marketing, acquisition and worldwide distribution of quality feature-length motion pictures, and is concerned with acquiring, producing and promoting films about equality, diversity and other thought provoking subject matter which will also include nonviolent storytelling.
Also in 2020, Sylvan launched SEGI TV, a free OTT streaming network built on the pillars of equality, sustainability and community which is scheduled to reach 100 million U.S household televisions and 200 million mobile devices across Roku, Amazon Fire TV, Apple TV, Samsung Smart TV and others.
As Executive Producer he currently has several projects in production including The Trials of Eroy Brown, a story about the prison system and how it operated in Texas, based on the best-selling book, as well as a documentary called The Making of Roll Bounce, about the 2005 coming of age film which starred rapper Bow Wow and portrays roller skating culture in 1970’s Chicago.
He sits on the Board of Directors of Uplay Canada, (United Public Leadership Academy for Youth), which prepares youth to be citizen leaders and provides opportunities for Canadian high school basketball players to advance to Division 1 schools as well as the NBA.
A former competitive go kart racer with Checkered Flag Racing Ltd, he also enjoys traveling to exotic locales. Sylvan resides in Vancouver and has two adult daughters.
Sylvan has been featured in Forbes, the Wall Street Journal, the New York Times and has been seen on Fox Business News, CBS and NBC. Sycamore Entertainment Group Inc is headquartered in Seattle, with offices in Los Angeles and Vancouver.
