When The Perfect Pitch Goes Sideways

When Anastasia Trofimova walked into The Pitch Room she had everything going for her...

Anastasia had the VCs wrapped around her finger. Three offers, from three VCs. Totaling over $1 million.

And yet... she walked away with nothing in the end.

This isn’t your typical startup story. It’s a masterclass in how human psychology, perception, and timing can derail an otherwise stellar pitch.

🎥 Want to watch this exact pitch unfold? Check out Anastasia’s full episode on YouTube

The Setup: All The Right Moves 🎯

Step 1: Founder sells everything she owns in Sweden and moves to Silicon Valley to start the "LTK for groceries".

Her startup, Sundae (formerly YourBeet), has massive market potential. Here's why investors' eyes lit up:

The timing? Perfect.

As Anastasia put it, “In 2019, just in the US, online grocery shopping was two or three percent of the total market. Now it’s almost 20 percent and it’s growing.” Meanwhile, social commerce has tripled in the past three years and is projected to grow 14x in the next five. The tailwinds are strong.

The model? Proven.

LTK already proved that influencers are desperate for better monetization tools. And they’ve turned that need into a company that’s valued at $2 billion. Anastasia is building the same toolset and revenue potential to food influencers. Makes sense.

But Sundae has a second customer, CPG brands who are desperate for data about who is buying their products. Anastasia’s first brand pilot increased conversion rates by 22x using Sundae's data layer, bridging influencer content and real-world grocery sales—a holy grail for CPG brands drowning in unattributed marketing spend.

The opportunity? Massive.

Global CPG brands spend over $2 trillion a year on marketing, much of it in the blind. Sundae made that spend measurable.

Anastasia checked all the founder boxes too: Domain expertise? ✓ Proven execution? ✓ Grit to relocate continents and rebuild? ✓

Jaws Hit The Floor 😮

The investor reaction? Electric.

“For those who can’t see, my jaw is currently on the floor.” - Kate McAndrew (Baukunst)

She offered to lead with $1–2M.

“You’re very clear, you’re very dynamic, you know your stuff.” - Elizabeth Yin (Hustle Fund)

She put $150K on the table.

Charles Hudson (Precursor): Offered a minimum of $25K with potential for more.

Even Ben Zises, who had to pass due to a conflict, called it “really impressive.”

Three offers. Multiple paths forward. What could possibly go wrong?

Don’t want to spoil the end? Watch the episode here.

Plot Twist: Everything Goes Wrong 📉

Remember that feeling I mentioned at the start? Here’s where it kicks in.

Kate’s enthusiasm quickly turned into a dead end. After promising a decision “by the end of next week,” she sent the dreaded email:

“We dug out compelling competitors in this space, and based on diligence calls made over the weekend, we don’t feel like we can make a high conviction pre-seed bet here.”

Anastasia was disappointed but quickly moved on to the next offer, from Elizabeth Yin at HustleFund.

On the diligence call the following week Elizabeth reiterated her offer to invest $150K at a $7M valuation. Anastasia pushed for $8M, but Elizebeth held firm at $7M.

Suddenly the perfect pitch turned into a painful choice: Take less money on tougher terms, or walk away.

Anastasia chose door number two.

The Strategic Decision

Taking HustleFund’s $150K offer would’ve meant:

• ✅ Her first U.S. institutional VC on the cap table

• 🔥Warm intros to a bunch of U.S. VCs (who could potentially lead her next round at a higher valuation)

• 🌲A massive founder network and access to HustleFund’s Redwood School that teaches founders how to fundraise

But it also meant higher dilution than Anastasia had planned—and a potential mismatch with her vision of the round.

So she walked.

What about that other offer? 

Charles Hudson offered to invest a $25K starter check. Then they jumped on a diligence call after the show and everything seemed in order. 

After that call, Charles passed in an email.

But those weren’t the only VCs Anastasia pitched 😏

The Sundae story will continue in the season 13 finale… which btw AIRS NEXT WEEK!

📩RSVP to watch the season finale as it’s streamed LIVE on YouTube next week at pitch.show/party

What Would You Do? 🤔

As Anastasia put it:

“I think building is the most exciting part of life. I mean, that is what life is about to me.”

The building continues, even when the funding doesn’t follow.

She may have walked away from the deal—but she’s not done building. Watch what went down on YouTube 📺