History By Mail - Client of Downstage Media’s - Tests Its Brand Message on Shark Tank
When Messaging Meets a Once-in-a-Lifetime Moment
When I tell people that content strategy can change the trajectory of a business, this is exactly what I mean.
On April 4, one of my 1:1 Spotlight Strategy clients—Ari Siegel, founder of History By Mail—will appear on Shark Tank, pitching his unique, story-driven subscription service to a panel of billionaire investors.
Millions of people will be watching. The exposure is massive. The stakes? Even higher.
But this wasn’t about winging it or just “being passionate.” Ari didn’t just show up with a good idea—he showed up with a message. A clear, compelling, meticulously crafted pitch that took months of strategy, iteration, and preparation.
And I had the absolute privilege of helping him shape that message.
Because when your one-minute pitch is going to be broadcast to a national audience, every word matters.
A Quick Intro to History By Mail
What It Takes to Get on Shark Tank
The Messaging for the Pitch
The Art of Cutting — and What to Leave In
Real Mail, Real History, Real Impact
What You’ll See on April 4
How You Can Support History By Mail
Craft a Message for Millions
A Quick Intro to History By Mail
History By Mail is a monthly subscription that sends beautifully designed replicas of historical documents straight to your door. Each piece is carefully chosen, thoroughly researched, and printed on authentic-feeling paper. Subscribers also receive:
- A transcript of the document (in case your kids, like mine, can’t read cursive)
- A detailed historical explainer
- Optional themed add-ons—like Urban Legends or National Parks.
In a world of overflowing inboxes, it’s a delight to get real mail that’s educational, engaging, and yes—giftable.
At Downstage Media, I help business owners turn ideas like these into clear messaging and compelling content. But what Ari built? That was already a standout product. He just needed the right words to tell the story.
What It Takes to Get on Shark Tank
Let’s talk numbers for a second.
Every year, 20,000 to 40,000 entrepreneurs apply to be on Shark Tank. Less than 100 make it to air. Ari Siegel wasn’t just hoping for a lucky break. Instead, he reverse-engineered his pitch.
In our recorded interview, Ari shared just how intense his preparation was:
“I practiced walking down the hallway. I practiced every possible question. I made life-size cutouts of the sharks with different facial expressions—stern, smiling, skeptical—and rehearsed every answer in front of them.”
He also watched hundreds of hours of past episodes, wrote every question down on flashcards, and even created YouTube mock interviews with sharks reacting to his pitch.
That’s not just hustle. That’s strategy.
The Messaging for the Pitch
At Downstage Media, my work with clients goes beyond surface-level edits. I help business owners clarify their talking points, align their messaging with what their audience actually wants to hear, and create content that builds trust quickly.
That was especially important for Ari’s pitch.
“There’s the Shark Tank deal—but there’s also the ‘Shark Tank effect,’” Ari told me. “You get a one-minute commercial in front of millions of people. If the words aren’t perfect, the moment is wasted.”
So we went line by line, shaping a pitch that was:
Concise, while still being rich with meaning
Conversational, while still being confident
Entertaining while still being crystal-clear
We also used StoryBrand principles to position the customer (not the product) as the hero: Want to give Dad a unique gift this Father’s Day? Or help your classroom fall in love with history? Here’s how.
The Art of Cutting and What to Leave In
SHARK TANK – “1616” – Entrepreneurs pitch their innovative ideas, including a piece of history delivered, a virtual theme park experience, eco-friendly plantable pots, and a culturally unique greeting card. FRIDAY, APRIL 4 (8:00-9:01 p.m. EDT) on ABC. (Disney/Christopher Willard)
ARI SIEGEL
If you’ve ever tried to pitch your own business, you know how hard it is to edit yourself. You want to include every feature, every story, every special little quirk that makes your offer great.
Ari did too.
“I wanted theatrical elements. I wanted to tailor documents to each shark. I even spent six months licensing one specific document—and the shark I created it for didn’t care at all.”
But here’s what he learned: sometimes more is just more.
When we’re working with tight time limits (or short attention spans), clarity beats cleverness. That’s a principle I use in marketing strategy and content marketing all the time. You’ve got one shot. You’ve got one message. What do you want your audience to walk away remembering?
Real Mail, Real History, Real Impact
This whole experience reminded me just how much overlap there is between performance and content.
As a trained actor (BFA in Drama from NYU), I spent years learning how to deliver lines with intention, timing, and presence. These days, I use those same skills to help clients like Ari bring their pitches, videos, emails, and brand stories to life.
Because delivery matters.
So does research. So does preparation. And so does having a content strategist who’s wholeheartedly invested in your success.
What You'll See on April 4
SHARK TANK – “1616” – Entrepreneurs pitch their innovative ideas, including a piece of history delivered, a virtual theme park experience, eco-friendly plantable pots, and a culturally unique greeting card. FRIDAY, APRIL 4 (8:00-9:01 p.m. EDT) on ABC. (Disney/Christopher Willard)
Ari can’t reveal what happened in the tank (no spoilers!), but here’s what I can tell you:
He shows up prepared. He shows up polished. And the pitch you’ll see on Shark Tank is the result of thousands of hours of prep—including a whole lot of late-night sessions spent tweaking wording, adjusting tone, and rehearsing transitions.
The result? A compelling, memorable pitch that holds its own in front of some of the sharpest minds in business.
How You Can Support History By Mail
If you love history, storytelling, or just getting real mail again, head to historybymail.com and subscribe.
It’s a smart gift for:
Father’s Day (which comes up sooner than you think)
Graduation season
Teachers and classrooms
Anyone who geeks out on American history, historical documents, or National Parks (I know, me too!)
Ready to Craft a Message for Millions?
Whether you’re pitching to investors, launching something new, or just want to stop guessing at what to say—I can help. At Downstage Media, I work with business owners to clarify their message and build a strategy that actually gets their work seen.
Apply for the Spotlight Strategy Partnership—the same 1:1 support Ari used to prep for Shark Tank. It’s high-touch, high-impact, and built for business owners ready to make the most of big opportunities.
