Why We Passed on This Startup (Episode 4)

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.

The Pitch Coaching Call that Went Awry

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.

Coming Back Again

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.