How I Made Myself Feel Small

And What I Changed from the Experience

Not everybody thinks I am helpful. There is this one guy in the startup community who really dislikes me,” I said.

Here’s the story.

I met with a founder and his team in 2009. They were bright, talented, and chasing what looked like a big problem in a growing market. I was asked to join the meeting by my friend Mike who was interested in investing in the startup. He wanted to get my opinion on the team and the potential for this new business.

We met for a couple of hours. They presented, and then I made some observations. I spoke about their lack of industry experience and positional experience. I also asked questions around the partnerships which would have to be made with big players for the business to work. Clearly, there were lots of moving parts in the proposed business for it to work and reach profitability. This would make success hard and mean bigger risks to Mike, the potential investor.

In my mind, all of these comments were fair observations and concerns. The meeting ended. I didn’t invest but found out later Mike did. I didn’t pay much attention to the company anymore after the meeting.

In 2012, I read an article which described a $10mm plus VC investment in this company. I remember thinking, Good for them. They proved to me and to the rest of the world I was wrong about them. Although I believe my concerns were valid, they showed that, in spite of the realities I outlined, they could overcome and did. This multi-million dollar raise was the beginning of the building of a national brand which even today continues to grow to heights I could not envision.

So I wrote the founder an email in 2012 which said, “Congratulations! Good to see our local boys killing it. I’m so proud of you guys. This last raise really puts you in a whole new league. I wish you all the best.”

He wrote back, “Thx. Just wish the local community could have shown us some support.”

Being interested in how to make our community better, I wrote back and asked to meet and talk about it.

That’s when it happened.

He wrote back and told me I was one of the guys he was talking about. He explained that I was very helpful the first time he met with me on a prior business. But this meeting on this prospective business was altogether different. He told me, “You told us the business didn’t make any sense, had too many moving parts, and would require too much capital. I didn’t mind the business comments, but the personal assault was really uncalled for I thought.”

To tell you the truth, I didn’t remember the personal assault, but he did. I don’t think I went out of my way to make comments which would hurt and not encourage people. But that day I must have made those comments. The fact is, I’ve been reviewing startups and entrepreneurs for a long time and can’t remember being flat out insulting. That day was obviously different.

So I wrote back and apologized. Then I followed the apology with an explanation of why I said what I said. After hitting send, I thought, Now I apologized. Our relationship is healed.

Minutes later I got an email back from the founder. He outlined two points. He recommended I practice being the first Charlie he met with back in 2007 and not the second Charlie he met with in 2009. He then defended the guy he said I dressed down in the meeting. He said, “I’ve worked with him every day for four years, and partnering with him was one of the best decisions of my life.” That was the last time we communicated.

He was right, and I didn’t like it.

This founder is the only person in the community I believe steers clear of me. Most people consider me a friend to our startup community. But lately, while in conversations with close friends who are entrepreneurs, I’ve found myself telling this story. When I leave those meetings, I feel guilty for bringing it up.

  • Why am I gossiping?
  • Why does this email exchange of 2009 have such a hold on me?
  • Why do I feel it is important to talk about this experience?
  • Why do I keep breathing new life into something I feel guilty about?

I received this message the day after I told the story again to an entrepreneur who’s known me for thirty-five years: “You may have one or two critics, but remember 1,000s of people really love you! Not a bad average.”

Here is what I texted back, “Thanks. You made my day. Whatever I did in the past can’t be undone. It may be covered over with an apology. Maybe I can make the person I hurt question their opinion at some point in the future based on my new, consistent behavior. But in the end, his opinion of me and my relationship with him is not my choice. It is his. I must live with the consequences of my behaviors.”

This most recent recounting of the old story turned the corner for me. I accept today what he told me back in 2009. I hurt his feelings and the feelings of his team members. I assaulted them. Plain and simple, I was grandstanding in front of my friend Mike who was thinking about investing. I was trying to impress Mike, not help the founder and his team.

Here’s what I learned.

My focus always needs to be on the entrepreneur. He is my audience. He is my mission field. I am here to serve entrepreneurs. That’s my purpose and my market. When I am not doing this, I am serving myself, and that does not go anywhere good.

And don’t gossip. It makes me look like I feel. Small.

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One thought on “How I Made Myself Feel Small

  1. You may have felt small, but by putting this story out there for the world to see and potentially learn from, you have helped the rest of us who struggle in this same way all the time. The fact is, I do this kind of thing much more frequently than I’d care to admit.

    Why is it so hard for me to just own the things I’ve done that may have hurt others? Why can’t I just apologize and learn?

    It’s a lifelong internal fight, but when I see someone like you put your similar story out there, Charlie, it is sheer grace knowing that I’m not alone. It’s an act of courage on your part, and it feels like balm on my spirit.