Silicon Valley VCs are discovering a text is forever

Texting and messaging feels casual, conversational…and private. It’s easy and natural to slide into making an off-color joke, or trying out a flirtatious compliment to see how it lands.

But unlike actual conversation, text messages leave a lasting. In a number of cases, accusations of inappropriate behavior by VCs such as Justin Caldbeck and Dave McClure have been backed up by messages, saved by the recipient, that show an inappropriate blurring of professional and personal boundaries.

Before the advent of smartphones, users could save only a few dozen messages, and old conversations were quickly deleted to make room for new ones. Getting a complete record of someone’s conversation usually required a subpoena to the phone company.

But now, years of message history are archived by default, and screenshotting and sharing awkward conversations is its own social media sub-category.

No mistake, Caldbeck, McClure and the likes knew their behavior was inappropriate, and there is a written record of their actions that supports the accounts of the women who came forward — at substantial personal risk.

However, not all cases of message sharing and shaming are so clear-cut. In talking to users, we’ve run across cases of bullying and shaming for unintended or simply embarrassing messaging mistakes. Insta feeds like Tindernightmares, which collects cringeworthy Tinder exchanges, are sometimes hilarious and cathartic, but they also flatten the difference between messages that are rude and inappropriate, unfortunate typos, or just awkward. The result is unclear expectations around when it’s ok, or even courageous, to share private conversations.

Users have largely been left by messaging providers to fend for themselves in this shifting landscape. Messaging doesn’t have privacy controls, the ability to delete old, regretted content, or even know when screenshots have been shared and passed on.

At On Second Thought, we believe it’s time to give users more tools to control their messaging experience, better suited to the variety and volume of conversations happening via messaging. The low-hanging fruit is the ability to take back obvious messaging mistakes before the recipient sees them. Tools such as our curfew ability can help people who know they’re prone to sending drunk texts they’d never consider sober.

But considering how you’d feel if that private joke or pickup line suddenly became very, very public, perhaps having a second thought is never a bad idea — and possibly might save your career.

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