I went from “remote work will happen over the next 10 years” to “it’s already here, now what?” in under 6 months. To me, the shift was always inevitable but the timeline I could have never imagined happening this quickly. Remote work is here to stay.

Let me start by saying, there’s still a ton of things we don’t know about the impacts of remote work on our work and our lives. …

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This idea went from a text message “We should build this platform” to a full featured product in less than 4 months. It all started when Justin Kan, founder of Twitch & Investor, decided to quit drinking and start a community on Telegram. I called the best engineer and designer I knew and said “we need to build this product for Justin’s community. He has the community, we should build the perfect product.

We built it. And now we want to give it to you. The app (iOS & Android), the brand, the URL, everything.

On April 21st, 2019, Justin Kan wrote this Tweet thread about quitting…

I went from hating dating apps to kinda enjoying them again by changing one thing. It was so simple.

I forgot how fun it is to let friends play your Bumble. Flip through your Hinge. See your top 5 on The League.

Dating apps exploded when they became a game you played with your friends. It became the conversation at every dinner party. Your married friends loved to swipe your Tinder. People would even Airplay their dating app to the TV so everyone could be a part of the action.

This killed the stigma around online dating and made it social. It became an activity we liked to do with our friends vs the thing we hid from our friends because of the stigma. 5 years ago, I wrote an article about an idea I hoped someone would build to let friends play matchmaker. It never took off but I still feel like it should happen. …

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ask. celebrates 10 years with a blockbuster interview with Chase Jarvis. Next, David Marquet and others in a series specifically designed to go deep on the questions that define our lives and our work.

  1. ask. is back with a new podcast episode and a calling to let anyone host and be an interviewer.
  2. Here’s our first episode with new producers and the one and only Chase Jarvis celebrating his new book http://creativecalling.com

Grab this episode on the Apple Podcast app: https://podcasts.apple.com/us/podcast/ask/id1057357810#episodeGuid=tag%3Asoundcloud%2C2010%3Atracks%2F682865099

Spotify: https://open.spotify.com/show/7vu19eD9zFvJlgJnJZSCg5?si=SEX5nJM8Shy-oeoeONQwow

Or even Soundcloud: https://soundcloud.com/startbyasking/chase-jarvis-with-shane-mac

A simple idea then, and always. ask questions that reveal something important, personal, valuable to life & work. Today I’m dropping something insanely special, the personal side of Chase Jarvis for his new book Creative Calling. His message needs to be heard by everyone in the world. Especially parents who want to know how important creativity is for their children, and themselves, in this career landscape. …

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We are excited to announce an official partnership with Datawords.

This newly signed partnership will allow Datawords to help current and future clients integrate messaging and voice marketing tools to their digital marketing strategies. It will enable Assist to benefit from Datawords’ tech and multicultural expertise to deploy its platform at an international level by integrating new cultures, languages, etc.

When we think about taking brands global, being able to understand the local nuances of language is critical. This will ensure the highest quality, training, and understanding of the way people actually speak in different regions around the world.

We are just getting started but we are excited to help brands have great conversations anywhere in the world.

Read more about the partnership here: https://datawords.com/datawords-assist-partnership

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Machine Yearning posts its fourth episode this week, and already we’re breaking our format. We approach the podcast like everything in life: stay rigid, get stuck, nothing but problems follow…

We’ve used this podcast to jump start conversations about how much we don’t know about the worlds of AI, machine learning, and conversational commerce. We’re standing right on the edge of the talking internet and we can feel the wind at our backs pushing us forward. …

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Introducing Machine Yearning, our new podcast

In a world where no one is the expert and where everyone, even if they don’t want to let on, is scrambling to figure it out — why not come clean and get real?

That’s the point behind Machine Yearning, our new podcast. We’re launching Machine Yearning today with two episodes: Chris Messina and Kathryn Hume.

Machine Yearning is a place where we can gather together, talk, debate and dream about where we’re headed with AI, conversational commerce, our relationships with the machines and their impact on our language and culture.

We want the pod to be a place where you can hang with smart people who are guiding a fundamental reordering of how we interact with technology. …

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We’re excited to announce an official partnership with TimeTrade. TimeTrade is the leading intelligent scheduling platform for the enterprise.

Below is an interview with Cimarron Buser and Assist co-founder Robert Stephens. Cimarron Buser is SVP Business Development at TimeTrade. Since the day Robert founded GeekSquad in 1993, he has been thinking about selling time.

Enjoy the interview.

Cimarron Buser:

How does messaging and voice play into booking? Do you think booking is becoming more important?

Robert Stephens:

Well, let’s start at the beginning. Before there were death and taxes, the original constants in life were time and money. Even before the chicken and the egg conundrum, what came first, time or money? You know, there are really two things that people are doing in business: spending their money, and when they do it. In fact, in most commerce, there are really three questions that everybody asks of a business: can you do it, when can you do it, and how much will it cost? …

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8 years ago I made a video. I was young, excited, and starting to share things via video online.

I have no idea why I felt the need to send the video to Seth Godin. But I did. I don’t even remember what I said in the video I sent to him.

He responded. I couldn’t believe it. 8 years later I’ll never forget what he said or how he made me feel. He said,

“Did you know that they ADD the bubbles to San Pellegrino, I was amazed. Nice video shane.”

That’s it. That was the response. I remember it more than almost any email over the last 8 years. …


Shane Mac

CEO @Assist. Curious.

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