364 Jerry Colonna: It’s Not Enough To Be An Ally – You Have To Be A Co-Conspirator

This week we’ve got a special episode, a longer one than we normally do. But when you have an opportunity, to talk to the person who built the Rotman School of Management into the powerhouse it is today, you have to use every minute you get.  Roger L. Martin was told that the Toronto’s Rotman School wasn’t worth his time, that it was a quote – cesspool of intrigue. Roger himself will say that he didn’t do much in his 15 years as dean, just tinkering and prodding. He’s a bit of an understated enigma, as you’ll soon find out. But when Rotman’s prestige today ranks up there with Stanford and Harvard, you can’t really argue with his results.   There’s so much to mine in this conversation, we thought it would be a shame to cut it down and fit it within our normal episode length. If you have the time, I’d love for you to give it more than just one listen.  

Ask a thousand people how to make a house a home, and you might get a thousand different answers. Some will say it’s family; others say it’s all in the interior decor – neighborhood pride, or a furry friend, maybe.  Regardless of how you answer the question, you can’t just sit back and wait for it to become a home – everyone agrees that something needs to be done.  Our guest today is an expert on making that transition from house to home. Moving every 18 months or so, Ruth McKeaney raised five kids alongside her husband. Move into a fixer-upper, fix it up with the family’s help, sell it, rinse and repeat. It was only a matter of time until Ruth’s ability to structure her family’s systems came to the attention of book publishers. Hungry for Home is Ruth’s manual on building a home, everything from home restoration to frozen cookie dough.  

How many of us have mastered the skill of looking busy, at some point in our professional lives? It’s an art, really – moving from one tab to another with lightspeed, peering at the screen and making that face that you think communicates determination, drive, intent.    Our guest today says that it’s nothing to feel bad about. When a portion of the population moved from factories to cubicles, they still brought that factory-floor mentality with them. Look good in front of the boss, keep working, don’t stop moving. Cal Newport calls this pseudo-productivity – the art of looking busy.   Cal says there’s a way out, though. He calls it Slow Productivity – also the title of his new book, out now. How can we accomplish our dreams without the emotional and physical burnout that so many industries seem to take for granted?  

Many of us feel comfortable navigating a city. Whether it’s New York or Kyoto, the rules remain mostly the same. Count the amount of blocks you’ve walked, remember that the E train runs express to Manhattan, if you see the Duane Reade, you’ve gone too far. We can get lost, for sure, but there’s a joy in knowing that you have the freedom to get lost. A wrong turn could mean your new favorite Chinese spot, or a new friend. Now think about how you navigate the internet. We don’t explore and get lost as much as we stay within one small neighborhood – Facebook, Twitter, Instagram, LinkedIn.  Our guest today is fighting back against this centralization of our virtual city. Chris Dixon has been a partner at Andreessen Horowitz since 2012, most recently in charge of its crypto investing wing. From that birds-eye view, Chris has taken the charge on reimagining how we interact with the internet.  And now he’s out with a new book, Read Write Own, all about the Web3 revolution on our doorstep. So – a lot of buzzwords, and a lot of metaphors. But what does it all mean for you?   

In this episode, we wanted to bring you a redux of a conversation I had back in 2022. As a new mom, Brooke Romney left behind her roots on Capitol Hill to move to a new community, new friend –– a new S Curve.    But instead of making new connections, a normally extroverted person, Brooke found herself withdrawing from the community. Why? Well, she was surrounded by successful people, and Brooke fell into one of the most human traps there is – comparing yourself to others, and feeling she was coming up short.   As the new spring rolls around, this is a perfect episode to remind us to stop comparing. That little voice in our head can convince us that we’re coming up short, and only that little voice – your voice– can convince you that you are worthy, unique –– one of a kind.   

What makes a good story? Characters, plot, setting, sure – you can boil it down to those elements – but what makes a good story? Is it the moment where you’re up all night burning the midnight oil, because you’re dying to find out how it ends? Is a good story one you believe in? Our guest today believes in the power of stories. Donald Miller is the CEO of StoryBrand, a creative firm that specializes in clarifying a company’s message. In other words, taking a good story and figuring out how to make it great – how to make it one customers can genuinely believe in. Now Donald’s out with a new book, Coach Builder, all about how newly-minted coaches can write their professional story and succeed in the industry. Link to Coach Builder promo: www.coachbuilder.com/disrupt  

“True transformation, begins with a broken heart.” It’s something you’ll hear our guest today say a couple of times, this idea that a real crucible moment begins when something inside you breaks. When a force fundamental to you and your soul says – no more. Jerry Colonna has taken that message and run with it throughout his entire career, from the hallways of venture capital to his current venture in coaching. Today, he’s out with a new book on healing that break, titled Reunion: Leadership, and the Longing to Belong. But how do you harness the power of a broken heart in the first place? How do you turn that into fuel for true transformation?

When’s the last time you felt out of place? I’m sure a lot of us have sat with that feeling, whether that’s professionally or personally. It can hit you just as easily in a boardroom meeting as when you’re out with friends. So now that you feel like an alien that’s crash-landed, what do you do? Our guest today has built his career around finding community for these so-called “black sheep.” Peter Sims is a former corporate investor who became disillusioned with the high-powered world of finance and left to form his own creative firm – appropriately named, Black Sheep. It’s also the name of his new book, out in May, subtitled The Quest To Be Human In An Inhuman Time. What can we take away from Peter’s journey, to help us better navigate those moments when you feel the need to find a new tribe?

At DA, we’re all about discovering and harnessing disruption, but sometimes, disruption finds you. It’s a fact of life – our car skids on ice we didn’t see on the road up ahead. Your boat hits a reef at night. A business deal falls through out of nowhere, and there’s nothing you can or could have done. Now that your car’s in a snowbank, what’s next? Our guest today has been there and back. After the company she worked for collapsed while she was on maternity leave, Carol Fishman Cohen decided to leave the workforce for 11 years to raise her children. Today, she’s the CEO of her own company, iRelaunch. Carol’s had to fight through the nitty-gritty of getting back into the office, remembering and trusting in her capabilities, and today her company helps others make the same jump. Her story is, quite literally, a case study in how people disrupt themselves in response to being disrupted.

When we talk about robots, machines, artificial intelligence, it’s usually within the context of something theorists call the singularity. That’s the moment when AI figures out how to upgrade itself, and leaves us in the dust. After all, it can learn a library in an instant – the AI doesn’t need to stop for a snack and a nap.  In the world of the Terminator, it took Skynet a single day to become self-aware, destroy most of human life, and then send Arnold back in time to make sure no one could stop it. But in the end, The Terminator is one person’s vision of the future – a vision that’s also designed to sell well at the box office. Isn’t it just as possible to write a different version? Our guest today is spending his time doing just that. Paul Allen, the co-founder and former CEO of Ancestry.com, is asking instead – what if we saw AI as an ally, not an arms race? With his new venture, Soar, Paul is writing a different story, one where the robots aren’t sent back in time to strip away our humanity, but rather – they exemplify everything that’s unique about being human.