I presented terms + the recommendation to invest in **Startup X** at an approx. $18M valuation.

My recommendation was rejected.

Startup X is now worth north of $350M.

• My sisters use their products.

• My friends use their products.

• I use their products.

I freaking loved Startup X.

• Great product

• Addressed an unmet need

• Impressive & relentless Founders

• Excellent strategy

• Great terms

• And, I found Startup X via unyielding grit – they were totally overlooked

I was sold.

I thought my other stakeholders would be sold on Startup X, too.

But, they didn’t buy.

No deal in Startup X.

What I Could Have Done

1. Prepared My Stakeholders Sooner

   I introduced Startup X at a more formal investment meeting… I could have put the bug in their ear about Startup X sooner and more casually.

2. Prepared Alternatives to the Terms I Had Presented

   What if we worked out a convertible debt arrangement w Startup X instead?

3. Fought Harder for My Rec

   Respectfully of course… I was confident Startup X was a good opp.

What Startup X Could Have Done to Help Me Persuade My Stakeholders

1. Provided Educational Material on their Product

   I understood their Product — because I was their target market — but my stakeholders did not (they weren’t the target market).

   The Product research Startup X did send was comprehensive and very academic — not easily shareable.

2. Product-Market Fit Context

   Startup X was addressing an unmet need with remarkable upside…

   … but the supporting qualitative and quantitative data on the competition & appetite for target consumers to buy were not present.

3. Crafted Their Best Story

   Startup X’s branding was excellent, and their founders were “built different.” But that wasn’t showcased well in their deck and data room.

Since Startup X didn’t have 👆👆👆…

… it was left to me to explain and sell the product, market opportunity as best as I could with the information & resources I had.

You may be thinking…

“But dude, that’s your job… to thoroughly know and sell the startups you present.”

Eh, sorta…

The thing is:

• Startup X was 1 of 9 recs I made that day to meet quota.

• And they weren’t the only “let’s invest” rec on my docket — we would move forward with 2 at most.

• I had to be prepared to defend all 9 recs which is remarkably time consuming.

• I simply couldn’t build what I wasn’t given… said differently, I couldn’t become a product expert in Startup X’s space in a matter of days.

• Our charter was broad; wide net vs. deep net.

👆👆 most Founders don’t ask funds about this.

The Result? I Settled.

So instead, I settled for a future “I told you so” when my recommendation was rejected.

I could still earn some credibility this way or save face if Startup X flopped.

Not gonna lie, it felt sweet when Startup X crushed it, and I had my “I told you so” moment with my stakeholders.

But I would have much preferred the huge return.