Meaningful Conversation 2 – Talking to Family About Your Startup

I am running a social experiment to have more meaningful conversations. This is a recap of one of my attempts. If you want to see why I am doing this, please read this: My Experiment to Have More Meaningful Conversations.

I am genuinely excited by my pseudo-experiment (I don’t think I can officially call it an experiment because I have no real hypothesis). After my first success, I was ready for attempt number two. As opposed to a semi-stranger, I decided to play it safe and try my sister.

I want to include family because, for me, it’s always been tough to talk about Clippo with them. It’s their job to be worried about my well-being and since startups are a never-ending series of volatile emotional swings, it’s easier to just talk about something else.

I feel like I can already hear my psychologist roommate saying this is the exactly WRONG way to handle your emotions. My naïve method was to just email positive press and give high level updates. I am not really sure how I ever thought this was a good idea. I started doing it a few years ago when we were bootstrapping the company and I was working out of my apartment and living with my co-founder. I was having a real issue separating work from the rest of my life.

I wouldn’t be surprised if this is common for those that work from home, since there is no physical separation between work and home life. I created a plan to have designated “work” times and designated “no work” times. Admittedly, this plan does not work very well–I am always thinking about what products we are building and how to make them better. However, in my mind, having some separation, even an imaginary one, has become very important to me.

My conversations with family members easily fall into the “no work” category because there are so many non-work things to talk about. But to be honest, I really just don’t want to worry about them worrying about me.

This time, when, my sister asked, “How is Clippo going?” I came clean. I told her we had just launched a major bug-squashing update to the app and that our largest problem was figuring out how to acquire new users and bring back our old users.

I think my sister skews my experiment results for two reasons: 1) she is family, so is going to go out of her way to help me, 2) she knows tech and marketing – she worked in the industry for about 8 years and is currently a rising star at a very successful start-up. I was not exactly asking a random stranger on the street for user acquisition advice.

She had some really great ideas. My favorite was the #getweird campaign. We were trying to brainstorm a hashtag that we could “own” and would spark people’s creativity to make funny and shocking memes. The idea is to have people make Clippos of the weirdest things they see on the street, at work, late at night, or at home. (In fact, I’m going to be running around San Francisco next week making funny memes in offices, on the streets, everywhere. If you are interested in helping out, please email me.) I would definitely count this as a positive outcome for experiment trial #2.

Going 2 for 2 so far has my confidence about as high as it can get. After sharing drafts of this post with a few people, they asked some interesting questions that I do not have the answer to yet. I thought the best way would be to share them below. Hopefully, I’ll be able to better answer these in future posts.

• Are you worried how conversations like this impact your personal work/life balance?
• Are you going to reach out to her more regularly?
• Do you think these conversations will actually improve your relationship with her?

I think the next iteration for family is to talk to a non-tech knowledgeable family member and see if the result is as positive. I’m curious for anyone reading this – do you have problems talking to your family about your work?

Thanks to Vineeta Agarwala, Nick Meyer, Daniel Post, and Ritika Goyal for reading.