My friend Anthony Lee is incredible, and he’s had quite the week. He makes me proud. Let me tell you why.

Most investors dream of one massive exit in their careers. Anthony and his firm, Altos Ventures, have had two (Roblox and Coupang) — in the past two DAYS. After this week, I suspect the NYSE will have a plaque in his honor.

There are so many lessons to learn from Anthony and Altos Ventures. I picked five to start.

1. Character matters

Good, humble people can “own the podium.” Despite what the “Midas List” thinks, Anthony is one of the best investors…


Illustration by Laetro

“Dad, I think I want to be John King when I grow up.”

Yes, that’s an actual quote from my fifteen year-old-son, Jack. Big words from a kid that doesn’t want to do his English homework, I thought. But Jack was serious about his love for CNN’s indefatigable anchor and election map wizard. John King even earned the highest form of compliment from my teenager — a TikTok video. And I understand why.

There is nothing more inspiring than watching someone at the top of their game. As he nimbly works the magic board and engages talking head after talking…


Part 3 of 3: Adjusting Your Sails to Navigate Today’s Choppy Waters

Illustration by Laetro

For the last installment in this series, I want to return to that moment on the sailboat, the first time I found myself caught by the ferocious wind, the roller coaster waves I didn’t know how to crest. In that moment, when you’re faced with a new and seemingly insurmountable challenge, it’s easy to think: I’m not ready. I can’t make it. And in a way, it’s true. Because you can never really be ready. And you can’t make it until you do make it. …


Part 2 of 3: Adjusting Your Sails to Navigate Today’s Choppy Waters

Illustration by Laetro

A captain is only as effective as her or his crew.

It’s a lesson I’ve learned time and again in my career, through making the mistake of trying to go it alone. In a crisis like this one, you need a solid crew more than ever, not just to run a tight ship, but to keep you — the captain — on course.

In my last post, I shared five strategic insights from previous downturns and turnarounds. …


Part 1 of 3: Adjusting Your Sails to Navigate Today’s Choppy Waters

Illustration by Laetro

Growing up in a small Canadian town on the shores of Lake Huron meant sailing became part of my life from an early age. And though I am a decidedly mediocre sailor, I always enjoyed those hours out on the water, full of sunshine and sea spray. That is, until the first time I went out thinking I was in for a pleasant afternoon — only to be walloped by a ferocious wind and drenched by a thumping wave.

My love for sailing grew stronger through that first sloshing, and so has my tendency to find in sailing a great…


“If you build it, they will come.”

It’s a maxim that works for baseball diamonds in cornfields, not so much for building a bridge across the chasm between product-market fit and scalable growth.

In the canon of Silicon Valley mythology, no yarn is as durable as the garage myth: two brilliant Stanford dropout engineers have a “Eureka” moment in a rented garage and decide to start a company. Pretty soon they’ve developed a groundbreaking product and earned rave reviews from the first twenty customers, achieving the coveted “product-market fit.” And then, like magic, sales just go up-and-to-the-right because the product…


“The pessimist complains about the wind. The optimist expects it to change. The leader adjusts the sails.”

I think John Maxwell, author of one of my favourite quotes, would agree that the winds are blowing pretty hard at the moment. As salespeople, we’re used to facing many challenges — from listening to prospects and customers to understand latent needs, to engaging prospects with compelling storytelling and overcoming objections of every sort to deliver results each quarter. But the COVID-19 crisis has upended all expectations for the year ahead. Now, the table stakes are simply to survive.

Even as we face daunting obstacles, remember that every crisis is an opportunity to accelerate change and build a stronger team…


“We shall never surrender.”

So said Winston Churchill in 1940, facing likely defeat. Not “we’re winning.” Not “we’re about to win.” He told the truth and inspired confidence in the face of mortal danger. The British victory that followed was unexpected — but without his leadership, much less likely.

The crisis we now face might not be a military one, but it is testing our stamina like no challenge in recent memory. As we burn the midnight oil, trying to figure out how to survive each new setback, we must inspire confidence, while deep down we might feel unsure.

How…


May you live in interesting times. Well, “interesting” is one way to put it. Today’s crisis will touch all aspects of our lives, profoundly impacting human-to-human interactions.

Almost overnight, working and leading remotely went from fringe to mainstream — as did team bonding through virtual lunches and impromptu introductions to kids, partners, and pets. Unfortunately, fear and risk-averse behaviour have become mainstream, too. Though hopefully temporary, these understandable human emotions will have a very real impact on your sales pipelines and your optimal go-to-market strategy.

While there’s no playbook for dealing with the level of uncertainty we’re enduring, we’ll outline…


I’m excited to announce today that I’ve joined Sagard Holdings as a Partner at Portag3 Ventures.

I’ve been thinking about making the transition from operator to investor for some time, and after meeting Paul Desmarais III, Adam Felesky and the Portag3 team and learning of their desire to plant a flag in San Francisco, now seemed like the perfect time. I couldn’t imagine a better place to have fun and make an impact in the next phase of my career.

I’m excited to partner with exceptional founders to help turn their dreams into reality and support them at every stage…

Chris O'Neill

Partner at Portage Ventures. Board Member at Gap Inc. Former: CEO at Evernote, Leader at Google, Board Member at Tim Hortons

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store