4 Lessons I Learned from Being a Contestant on Shark Tank

Most people watch Shark Tank for the thrill—fast-paced pitches, high-stakes decisions, and fierce negotiations. But for me, appearing on the show wasn’t just a business milestone. It was a deeply personal journey that reaffirmed my values, my priorities, and my belief in something greater than myself.

As the founder of HistoryByMail.com, a subscription service delivering replicas of historical documents to mailboxes around the world, I never expected to end up on national television. And yet, that experience taught me four lessons—ones that went beyond entrepreneurship. Lessons about timing, sacrifice, identity, and kindness.

1. There’s Order in the Chaos

In January 2024, I got an email that seemed too good to be true: Shark Tank was interested in my business. I wasn’t even sure the email was real. But I’ve always believed in walking through open doors—you never know where they’ll lead.

As the process moved forward, delays kept popping up. The taping was scheduled, then postponed. Then scheduled again. Then moved again. Each shift felt frustrating—until I realized those extra weeks gave me more time to prepare: my business, my pitch, my mindset.

When I finally taped my segment, I landed a deal with Barbara Corcoran and Daniel Lubetzky, founder of KIND Snacks and son of a Holocaust survivor. Daniel—a proud Jew known for building companies rooted in values—resonated with me on a deeper level.

The night we finalized the deal after due diligence happened to be Tu B’Shvat, the Jewish holiday that celebrates trees by eating fruits and nuts. I quietly marked the occasion by handing out KIND fruit and nut bars at my Tu B’Shvat gathering, a small, private way to say thank you—for the moment, for the alignment, for the connection.

Ari Siegel

Taping a Shark Tank episode – even securing a deal – is no guarantee that your episode will air. Many pitches are filmed and only a handful are broadcasted. Weeks later, on Purim—a holiday that celebrates hidden miracles—I got the official news: my episode would air.

Looking back, what felt like a logistical mess was actually choreography. Everything happened in exactly the way it needed to. Sometimes what seems like bad timing is really perfect timing in disguise.

2. Never Compromise What Matters

After nearly a year of preparing for the show—including hours of daily rehearsal—I finally got the taping date. Then I saw it: Shabbat.

I keep Shabbat, which means I don’t work or travel from sundown Friday to Saturday night. That includes flying to LA and filming a TV show.

I told the producers I wouldn’t tape on Saturday. They said they’d try to accommodate me, but made no promises.

I was crushed. After all the preparation, was I really about to lose the opportunity of a lifetime?

But the truth is, I had already won. I had chosen not to compromise what matters most. And in that moment, I realized: success isn’t just about what you achieve—it’s about how you achieve it.

A few weeks later, the studio offered me a new taping date. More time, better prep, a stronger pitch. And a deal I wouldn’t trade for anything.

Sometimes standing up for what you believe doesn’t cost you—it elevates you.

3. Be Proud of Who You Are

I didn’t grow up religious. I only started keeping kosher, observing Shabbat, and wearing a kippah in college. Of all those things, wearing a kippah in public was the hardest. It made me feel different—exposed.

For a long time, I wore a baseball cap. But as the years passed, I embraced wearing a kippah more fully.

So when it came time to appear on national TV, there was no hesitation: I wore my kippah proudly.

I also dressed as President Lincoln as part of my brand’s historical theme, wearing a custom-made kapota, a long black coat worn by Hasidim. Mark Cuban took one look at me and said, “I wasn’t sure if you were Lincoln or a Rabbi!”

Ari dressed as Abraham Lincoln on Shark Tank

That moment—unexpected, humorous, but meaningful—was a reminder that we don’t need to preach or explain who we are. Just by showing up authentically, we can shift perceptions.

Millions of people saw that episode. I didn’t quote Torah or speak Hebrew. I just tried to be a mensch. Sometimes, that’s the most powerful way to represent your values.

4. Lead with Kindness

Daniel Lubetzky didn’t just invest in my company—he inspired me. He built KIND Snacks around a single, powerful idea: that kindness matters.

Daniel’s father was a Holocaust survivor. In a concentration camp, a German soldier once tossed him a potato—a small act of humanity in a place that had forgotten it. That moment stayed with him, and it became the foundation for a brand built on compassion.

It’s easy to think that kindness is soft. Or that it doesn’t matter in the high-stakes world of business. But it does.

A kind word, a thoughtful gesture, a moment of patience—these things ripple far beyond what we see. We don’t always get to know how they’ll unfold. It’s our responsibility to plant the seed and let God do the rest.

Final Thoughts

Shark Tank gave me exposure, opportunity, and a business deal. But more than that, it gave me clarity.

It reminded me that life—like business—isn’t just about numbers or strategy. It’s about staying grounded in your values. Trusting that delays have purpose. Choosing integrity over convenience. And believing that kindness, no matter how small, matters.

And if you pay attention, you might just find meaning in the most unexpected places—even on reality TV.

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