Regrets Hurt

I have regrets. Lots of them. I have regrets from one hour ago. “I should’ve said this on the sales call”. I have regrets from growing up. “I should’ve asked this girl out”. Shoot.

Regrets limit our thinking. When we’re regretting, we’re living in the past. Punishing ourselves for things not done to our expectations.

I’ll write future posts on regrets. I’ll share regrets around business. Other posts will be how I try to deal with regrets.

Let’s talk about a business one. About 5 or 6 years ago I was partners with two other people in a firm. We were called Iconos. I loved the two other partners. We were trying to put together deals, mainly helping raise money. We never put one deal together. We were all part-time and probably not aggressive enough.

We did come across three deals where we could’ve done well. One of them would’ve been a competitor to Peloton. Peloton let’s you workout on your bike with other people across the world. You can race together virtually. They’re now worth north of $1 billion.

The competing company was based in Madison. The owner is a pretty brilliant inventor. He had bought the technology and continued to develop and enhance it. It was cool. It worked. It might’ve been ahead of Peloton at the time.

I feel like this was one of those I missed big time. The best thing about regrets is what you can learn from them, both from a practical and spiritual standpoint. Spiritually they let you practice letting go and relaxing with the regrets. Freeing you up to live now. Thank you regrets:)

Practically, I learned a couple of things from this:

1. I should’ve pushed the owner a little harder to raise money, clean up the operations. I was too nice. You can always be nice. But I wasn’t direct enough. You can be direct yet still do it with love.

2. This technology worked on pretty much any stationary bike. Peloton only works on their own bikes (or at least did at the time). I thought that limited their potential market. I was wrong. By integrating their technology into their own bikes they could control the hardware and software and the experience. We would’ve depended on third party companies to work with us. That would’ve been more of the Windows way. Peloton chose the Apple way.

If possible, I would’ve chose both ways and see which one gathered steam faster. We could’ve worked with a third party bike manufacturer to brand our own bikes.

This all seems easy in hindsight. But I know at the time the company was stressed to the max.

Regrets. Thank you and good bye until next time.

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