We were lucky to catch up with Ashley Love recently and have shared our conversation below.
Ashley, thanks for joining us, excited to have you contributing your stories and insights. Earning a full time living from one’s creative career can be incredibly difficult. Have you been able to do so and if so, can you share some of the key parts of your journey and any important advice or lessons that might help creatives who haven’t been able to yet?
My grandfather, who lived through the Great Depression and was a very frugal and smart man, had a saying: “Be in the business of something people need everyday.” People surely don’t need what I do everyday, maybe, but our on-going clients do need their constituents’, clients’, members’, beneficiaries’ stories told and when you add up several clients with several retainers, the foundation is there to keep the company afloat. Especially since you know you can count on future business to make investments in the company, buying new gear, taking a risk, or doing a pro-bono project for a deserving costumer. With the steady stream of income in place, we know what our framework schedule is and then can fill in one-time contracts for events to fill in the time gaps and supplement our income even more. Sometimes those one-time gigs turn into several projects! Our repeat work can be connected to a person, a class of boats, a venue or an organization. Establishing a bond with each part of the puzzle helps us in the long-term.
It’s really about the people on the other end of the project. They may come and go from their roles, but they always go somewhere else after some amount of time and wherever they go may need our services too! The personal connection with the client, the people the project is about and everyone in between is focused on every step of the way to ensure our reputation is strong and word of mouth links us to new directions.
The other thing that keeps us employed is each of us being Jacks and Jills of all trades. We can easily morph into a wide range of deliverables to keep us attractive to clients, can split up and cover several projects at the same time with the help of sub-contractors and can keep costs and expenses low. We specialize in a very challenging niche: Sailing, so we figure if we can film that, we can film anything. Rain, pounding heat, snow, lightning storms, filming on powerboats, sailboats, helicopters, dealing with wet, salty spray, long days, long events while having limited access to power, internet, and the comforts of land are nothing out of the ordinary for us. The people we have met while under those conditions all have jobs and lives outside of this passion where they meet us. When something comes up in another avenue, so do our names.

Ashley, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
For over twenty years T2PTV has been creating content for the web. By the numbers that’s over 2,000 videos and over 7 million views, with over 5 million on YouTube. It’s experience that does count.
The company was originally started as a marketing firm to represent corporate America in the sport of sailing. That morphed into an Internet broadcast company hosting major sailing events worldwide before the advent of YouTube. Today T2PTV has branched out into a lot of different areas producing all kinds of content for all kinds of clients: Corporate, Institutional, Non-Profit, high-end real estate: Wherever there is a unique story to be told.
Our roots, however, are in the sailing world. We specialize in same-day regatta coverage, which has brought us all over the United States and the world. We do whatever it takes to bring the story to an audience. We aren’t just pretty shots. We aren’t just hashtags. We are content-creation with a delivery strategy to get results: sell things, raise money for a non-profit, get people to join, and/or build momentum for an on-going mission.
How’d you build such a strong reputation within your market?
Building our reputation is a big priority for us, especially since we’re in the creative space. New clients who are unfamiliar with our work, understandably so, can be wary of what they’re getting into picking us for their project. They know their story, their message, their subject matter better than anyone and we at T2PTV pride ourselves in being just the right size of a production company to fully tailor what we do to the client. We make it all personable and fun, while at the same time professional and thorough. We have always battled the elements and nature, heavily produced the projects as much as possible before-hand and educated out clients about, not only what we will deliver, but what we will need from them along the way to stay true to our word and meet their expectations. Their involvement at the right level and at the right times along the way can make or break an experience.
We also stand out because of our decades of experience, ability to wear many “hats” at the same time, hit the ground running to invisibly be in the right place at the right time and be low-maintenance. We meticulously archive our previous work so that we can bring up relevant examples for new clients, can film a wide range of things for a client while we are on site so that we can come back to it later to tweak for new calls-to-action or repackage things entirely for biographies, “about us” themes, capital campaigns, years-in-review or whatever is needed.
Filming sailing and being sailors ourselves is extremely important to being able to produce regatta coverage. We know the sport, we know the audience and we participate in the realm in so many different ways to keep ourselves relevant. This translates easily to other sports and to art, cars, real estate, charities, galas, concerts, anything, because sailing teaches you how to be a part of a team, how to anticipate, how to navigate through a challenge, learn from a mistake and have the patience while things are happening and debriefing skills after things have happened to be successful on any plane.
This type of work ethic goes a long way with a client and helps us keep existing clients and gain new ones. We’ve seen sailing video productions come and go over our tenure. We always remain, because we have a solid base of income to weather the storms, the reputation as an authority on what is relevant and ability to provide quality and quantity for a price that reflects our talents.

We’d love to hear about you met your business partner.
My business partner, Bruce Nairn, is the one who started the company back in 1999. I didn’t come along into the story of T2PTV until 2008 when I was assistant coaching the Hobart & William Smith college sailing team in upstate NY. I was making little videos for them to remind them how hard they worked and to celebrate their efforts and achievements. When I realized that I loved telling their story while being a part of that story more than the actual coaching, cold-calling alumni for money and attempts to recruit high school students, I new that my combined Theater and English major in undergrad was going to be used in real life: Storyteller. Sometimes I am a part of the story, sometimes I’m not, but either way, I’m combining my own passion with my profession and that story always turns out well.
While finishing up my school year at HWS, I saw a posting in sailing forum about T2PTV: Sailing on Demand needing interns. Having family friends based in Annapolis, MD, where the company is based, I came down for a visit and went out on a an Annapolis Yacht Club Wednesday Night Race with two people, who since then, became family to me. In that first meeting, though, I remember being in complete awe of the production. Big, shiny film boat with a suicide knob on the wheel. The commentator drove the boat and talked directly to camera being held by the videographer. We were right in the middle of the action without being in the way. Over 150 sailboats started, navigated a course and finished in tiny spit of water after about an hour of racing and the show these two guys made would have zero editing to make it up at the club and the bar that owns the film boat within the hour. Whatever the commentator said, whatever the videographer filmed went into the show. It’s white-knuckle producing and as a sailor who’d been racing forever AND an actress and story teller with barely any experience holding a camera, I was electrified with excitement. I couldn’t believe people were getting PAID to do something I’d see paying to get to do!
Soon after that trip, where I just watched and absorbed as much as I could, they invited me up to Newport, RI to film a big regatta happening up there. This is where I met my current full-time coworker, Bruce Nairn. He was the videographer and editor for this event and the commentator from my first Annapolis adventure, the other cofounder, Tucker Thompson, was there in that same role. They handed me a little camera and had me shadow Bruce. Only knowing how to hit the “record” and “stop” button, I started learning videography from square one. I watched how Bruce held the camera, moved around the boat, communicated with Tucker and positioned his body to keep a steady shot while waves moved the boat around.
On one of the days, Bruce handed me a camera with a ziplock bag taped around it and put me on one of the race boats. A big Swan 42 with an all-female crew. I had never been on a sailboat as big as that, nor had I ever really raced in the ocean. Off we went and while we were out there, I was running through Bruce’s instructions: “Only film what’s happening on board. Don’t pan and don’t zoom.” Close encounters at the starts, action racing up and downwind with sail changes and tactical battles blew my mind, but what really synched the deal of me deciding to do this forever was what happened in the third race of the day.
Around 2pm, several major thunderstorms formed around the race course and the wind started to pick up dramatically. It started pouring rain and the gusts got so strong that sails were shredding, but the racing hadn’t been cancelled yet. Our jib tore into 100 pieces and wrapped around the forestay, so the very brave bow girl climbed up there to try and get it untangled. While she was up there swaying back and forth being held to the boat with a measly harness and halyard, I had a tingly sensation creep up my spine. I knew I wasn’t supposed to film anything off the boat, but I, somehow instinctually, turned around to see another boat with their spinnaker up sailing a hotter angle (at a much faster pace than us) approaching our transom. They had to either gybe or speed up even fast to avoid colliding with where I was standing, so I turned the camera on their decision. Keeping myself in place holding the backstay with one arm and holding up the ziplock-covered camera in the other, I watched this boat capsize, the top of their mast falling, basically, at my feet in 50 knots of wind. And I filmed it all.
It was hard not to scream in the moment, but I somehow managed to do it, so as not to ruin the audio of the moment. When we sorted out our jib and were able to get back to shore safely, I ran to Bruce in the editing room and did start screaming. “BRUCE BRUCE!! You have to see what I GOT! Fast forward to timecode 16:09!” (We were still on tapes back then.) He did so and when he saw what I got, he responded, “Ashley, I got the same moment from behind on the film boat. We were right there!” I was hooked. Not only to this level of sailing or this medium of storytelling, but to being a part of a media team with Bruce. The first videographer and commentator I meant have become subcontractors and/or moved to other states, but Bruce and I are the back bone of the company all these years later (15). He and I share a bond that I bet few others have. Mentor/mentee, collaborators, creatives, we push and challenge and support each other to create some imaginative and incredible works that have been in film festivals, on TV and all over the internet. When the commentator left, I picked up the microphone and took the wheel to learn that job too, while still also playing the videographer/editor role, sometimes at the same event.
Contact Info:
- Website: https://www.t2p.tv/
- Instagram: Sailingondemand
- Facebook: Sailing on Demand
- Linkedin: Ashley Love
- Youtube: T2PTV: Sailing on Demand
Image Credits
Bruce Nairn, Shane Kilberg, Ingrid Harding

