Behind the Raise: What Analysts Flag, What Investors Miss, and What Founders Can Fix, TipMaster Spotlight

At LionRun, we ask a lot of questions—not to make things harder, but to make sure the answers actually hold.

Lately, the same ones keep surfacing: Why this round? What does this product actually do? Why isn’t the deck landing?

So we pulled together three takeaways we’ve been carrying into our client work—and that might be worth carrying into yours.

Message from Jason: The Analyst Is Your Gatekeeper

Here’s what happens behind the scenes at a VC:

When you send over your materials after a promising meeting, that partner is not the one digging into the deck, model, or data room.

They hand it off to their analyst.

That analyst is the one reviewing your deck, diving into your model, and writing up the internal memo.

So if your materials are disorganized, unclear, or incomplete?

You’re putting your fate in the hands of someone who has every reason to pass, and little incentive to piece it together.

Your job is to make their job easy.

Because if the analyst isn’t sold, the partner never sees the deal again.

Thoughts from Mia: Power of Distribution 

It’s never been easier to build tech.

But distribution? That’s where the real game is.

One of the biggest gaps we see in founder materials is a lack of a clear, compelling go-to-market strategy.

A lot of founder decks we see spend 10+ slides on product, but barely touch how they plan to grow. 

Investors aren’t just betting on the product; they’re assessing your ability to win a market. Who are you targeting, how do you reach them, and why is that credible?

That’s why your GTM story has to be nailed. It’s often the real differentiator.

Insights from Nina: A Great Business Still Needs Great Packaging

We’ve seen too many great businesses get overlooked by investors because they didn’t package themselves properly.

The deck didn’t land.
The numbers weren’t clear.
The story didn’t come through.

And as a result? Investors didn’t take them seriously.

Most founders don’t realize this: investors aren’t experts in your technology. There’s a knowledge gap.

Fundraising isn’t just about the strength of your business. It’s about how clearly and confidently you communicate it.

You don’t need to dumb it down, just say what it does, then build from there.

Client Spotlight: TipMaster 🏆

TipMaster is building a verified sports betting marketplace that rewards transparency. After validating their model in Israel, they came to LionRun to position the company for a U.S. market entry and to raise their series A.

We worked closely with Bar and Polina to sharpen TipMaster’s positioning, clarify their GTM narrative, and craft a full suite of investor materials.

It’s always bittersweet when a client leaves the LionRun pack, but we’re proud of the story we helped shape, and excited to watch them carve out their place in the market.

Follow TipMaster on LinkedIn to keep up with what’s next.

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