Once upon a time, I met a startup team.

Let’s call it ABC Company with Manny, the Founder and CEO. I had had several conversations with Manny.

Throughout the process of conversation with ABC Company, Manny introduced me to an advisor to the company, David. This individual had stellar credentials and a strong pedigree. The interactions with all team members were positive. There seemed to be enough variables in the startup’s favor that I liked a lot of the components of the deal.

I invited them to the pitch meeting to pitch Tundra Angels.

With every startup that pitches to Tundra Angels, I help founders by offering pitch coaching sessions with them to put them in the best chance to succeed at the Tundra Angels pitch and beyond.

I won’t forget this. During that first pitch coaching session is when the relationship took a hard left turn.

A few minutes into the conversation, Manny suddenly began to push back. He spoke to his vast experience pitching to investors and said that my coaching was unnecessary. I felt confused. I’ve had founders tell me that they have a fine tuned pitch already and had questioned the value of coaching. But, even in those cases, the coaching had still added considerable value to their investor pitches for the Tundra Angels pitch and beyond. But weirdly enough, Manny didn’t even want to embark on the pitch coaching.

Next, Manny balked at the fact that the pitch was only limited to 8 minutes, and complained that he couldn't cover the materials in that time frame. He preferred 20 minutes minimum. I maintained that I had coached founders with far more technical solutions and helped the founders make it easily understandable. But Manny maintained his position and refused to do the coaching.

I then proposed that Manny do some work himself and come back with a shortened draft of pitch that we could jointly review. Then, we ended the call.

The founder’s lack of coach-ability, that previously went undetected, was now blaring like a red siren on my radar.

Two days before the pitch meeting, Manny emailed me out of the blue. He said that he was withdrawing from the pitch because it’s impossible to communicate these concepts in an understandable way in an 8 minute time frame.

I gave a huge sigh of relief. I communicated to the Tundra Angels the last month of conversations and how this company was no longer pitching to the group.

I thought that was the end of the story.

Several days after the pitch meeting, Manny reached out again. Essentially, he said that he had a change of heart and that it would still be good to pitch Tundra Angels.

We had a semi-heated email exchange that included Manny giving me the full court press to find another time to pitch. (Another red flag, by the way)

I wasn’t having it. Essentially, I communicated, “Manny, we’re done.”

I thought that this was the end of the story. But I was wrong again.

About a month after this exchange, I got an email from David, the advisor who I had met several weeks prior, who sent me this email, copied verbatim:

David: “Good morning 

I think I caused some confusion re our presentation with Tundra Angels

David Johnson

123-555-3873”

Weeks ago, I communicated to David the industry backgrounds of our group, none of which were in this specific domain that the startup was in. David was referencing that he had communicated this to Manny and that may have been the reason that Manny withdrew from the pitch.

But to me, it felt like a lateral pass to try to re-open a closed door. I was firm in my conviction to not invest, so I responded,

Me: “Hi David, 

Thanks for the email. I don't think you caused any confusion. 

We won't be investing in ABC Company. We wish you the best.”

I did not receive a response to this message, and so thought the story had ended…

Two months later, I receive an email out of the blue from Anna, someone in my network that I know and have had a handful of conversations with over the years.

Anna:

“Hi Matthew,

Hope things are good.  Without much warning, I’m reaching out from a new email address.

My last project wrapped up and so I found my next thing and have become President of ABC Company.

Manny’s work at ABC Company is impressive. Not many companies at that stage are so de-risked. I did quite a bit of due diligence on it before joining and continue to be impressed.

Sounds like you and Manny have already met, and maybe the conversation didn’t go great. Would you be willing to talk about it and maybe revisit interest now?”

Anna Smith

President, ABC Company

My initial reaction was, “Unbelievable. What does she mean that the conversation “didn’t go great?” What story did Manny sell to Anna?

More specifically, did Manny put this on me, like it is my fault he withdrew from the pitch? It sure seemed like it.

So I sent another email, even firmer in my conviction than ever.

My email response:

“Re ABC Company, the conversation went fine. For transparency, Manny withdrew from our Tundra Angels pitch two days ahead of time. We've moved on and have been re-approached numerous times since then but are still committed to our decision to not pursue ABC Company. I wish the team the best and hope it works out well for them.”

I literally haven’t heard anything on this company ever again.