Barry O’Reilly goes solo in this season finale episode of the Unlearn Podcast. He answers listeners’ questions about perfectionism, permanent hybrid work, and letting go of the past, among other things.

Perfectionism In Startups

Q: How do you deal with perfectionism in the startup you’re working on at the moment? [Listen from 1:37]

A: There’s this notion that perfection is the enemy of done. One of the things I’ve definitely learned this year is that shipping wins; more so than anything else, delivering is a really great forcing function for all the components of what you need to make happen… What we’re finding is that the trick or the antidote to [perfectionism] is doing things smaller, sooner, and safer to fail, which becomes faster to iterate. [Listen from 1:45]



Content Marketing and Strategy

Q: How do you get the most out of the content you create under reach? [Listen from 3:30]

A: My tip here is ‘create once, use many times.’ Whenever I try to create a piece of content, the next thing I’m thinking about is how I’m going to slice it, dice it, cut it, triage it, put it on various different channels and in lots of different types, styles and formats. So I can do something once but it has a massive effect. [Listen from 3:34]

Takeaways From Podcast Guests

Q: How would you summarize the insights and learnings from your podcast guests about being change agents? [Listen from 5:39]

A: The three takeaways that I have from all of the episodes are: success doesn’t happen overnight, certainly isn’t in a straight line, and everyone’s stories are always interesting… A lot of their stories are about the heartache, challenges, twists and turns that sort of happened along the way because they’re real. I think the stories of how someone woke up one morning, went for a run, tripped over a stone and invented the next unicorn are BS. These people have hard, tough and lonely work at times, and they’re not afraid to talk about it. [Listen from 6:11]

Listen to The Innovation Stack with Jim McKelvey, co-founder of Square.

Impact of Hybrid Work

Q: Given that your move towards permanent hybrid work seems to be gaining serious momentum, how will this affect founders’ efforts to scale their businesses? [Listen from 8:49]

A: Get your team thinking about smaller, more frequent communication updates; create a culture that’s open and transparent about sharing problems and opportunities; be clear on what success is. Ensure that you’re communicating and regularly updating the metrics for success and how they’re pivoting the steps that you take; think more social media in terms of your communication style for companies rather than this archaic, once a month, all hands meetings where everyone gets together and does it. [Listen from 13:14]

Unlearning Process

Q: In the unlearning process, what encouragement do you have to counter the fear of letting go of the past? [Listen from 13:52]

A: I think one of the biggest fears people have about letting go of the past is they often tie their identity and their success to the things that have made them successful in the past. In many ways, the reason people have their current roles, positions, authority or perceived respect and identity is because of what they’ve previously done… A lot of my work was telling leaders not that what they knew was wrong, but that they needed to start thinking about how they can constantly adapt their behavior to changing circumstances. That was a much easier way to get them going. [Listen from 14:05]

Looking Back and What To Look Forward To

Q: What are you most excited about at the moment? [Listen from 20:34]

A: I am excited about the impending explosion of entrepreneurialism in the world. I see entrepreneurs popping up from the most unexpected places more so than ever before, [with the opportunity of] technology becoming cheaper, more accessible and more meaningful. I think the ability for people to come together to solve new problems with great ideas and actually enjoy the reward is going to be very unique. [Listen from 20:45]

Q: What kind of guests are you looking for for future episodes? [Listen from 26:21]

A: What I’m really looking for is to bring lots of early-stage, interesting innovators; people who’ve done it, people who are starting it. So if there’s anyone out there that you think I should be talking to, by all means, please introduce me and see who we can bring. The other small innovation we think we’ll do with the podcast next year is actually trying to have more panels; multiple guests, different people appearing on the show, getting a number of people having dialogue rather than just me speaking about one person individually. [Listen from 26:27]

Q: What’s the biggest lesson you’ve had so far in 2021? [Listen from 28:10]

A: For me starting out this year, I knew that I wanted to do something different; it was time to change… I knew I wanted to get back to building more and in many ways that was sort of my inspiration for making somewhat of the boldest bet of my life. I think the biggest lesson I’ve learned is that it’s all about the people. People are looking for a purpose at the moment, they’re looking to be part of something bigger, something more meaningful. [Listen from 28:13]

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