12 Things I Learned in 2021

Mariah is on full blast, eggnog is in the fridge and my toddlers are trying to figure out what the excitement is all about. It’s the holidays. 

For my last message of 2021, I wanted to shake things up. 

Instead of writing about tech or social media, I wanted to write a smorgasbord of reflections from the year.

Some are personal stories. Some are career takeaways. And some are creative side projects.

But all of them sparked a memory as I thought back on the year.

As you read it over, tell me if you learn something new. I love hearing feedback. 

Let’s dive in.

12 Things I Learned in 2021:

1. Family Time is Fragile so Make the Most of It

There will always be another email to send, client to close and round to raise. 

Our family members grow older every single day and we can’t change that. So get in front of it. I carved out time for a sabbatical earlier this year and I couldn’t recommend it more.

Takeaway: Invest time with your family in the moments that matter most. Your laptop will be there tomorrow. 

2. The Most Rewarding Startup is Raising a Kid

Building startups are great. But have you ever had a kid? I had my second earlier this year and took off quite a few days off to soak up the moment.

My sincere admiration goes out to all the parent entrepreneurs that cared for their kids and their startups this year.

Y’all are the true MVPs.

My new daughter, Elliot, and I soaked up lots of naps in the early weeks. 😴

3. Catching the Web 3 Wave 

Early in the year, I wrote about how cryptocurrency is transforming the internet. 

From DAOs to NFTs and everything in between, every day I come across a new platform. CEOs are continually sharing their vision on how to integrate blockchain or crypto into their business model. 

As of today, Web 3.0. is a fairly large bucket… machine learning and AI, smart home devices, crypto, blockchain, defi, NFTs, DAOs and many more acronyms. 

All I can say is that it’s worth paying attention to. Every new movement at first sounds daunting, but after time becomes integrated into our DNA. 

Takeaway: do your own research to see where you fall.

4. Angel Investing in Solutions I Believe In

As an active angel investor, I love supporting early-stage startups. This year, I had the opportunity to promote a couple of my favourites and the milestones they reached. Here are a few I’m proud of:

Thinkific: This year the Thinkific team went public on the TSX and as an early investor, I couldn’t be more proud of the waves they’re making. I’ve been a big supporter of Greg Smith and the team from the early days. 🎉

Klue: I couldn’t be happier for my friends at Klue. When I heard they announced the closing of a $62M Series B, I was beaming for the entire week.

Bubble: the future of no-code platforms are here to stay. I bet on the team at Bubble and I couldn’t be more jazzed.

5. Tinkering on a Startup Idea Platform called Kern.al

You may have come across a couple of articles about a side project I’m spending some time on… The name of the project is Kernal.

It’s a platform to connect founders, investors and startup ideas in the earliest stage of its ideation. It’s been fun to watch it progress and I’ve created a custom invite code for the first 100 of you to test it out. Let me know what you think.

6. Don’t Overthink, Just Ship It

In an age of countless ideas, news outlets and social media feeds, there’s never been an easier time to share an idea.

But in the same breath, it’s never been a nosier world to build a team and execute the concept.

My encouragement to founders: ship your idea as early as possible. Life’s short and you never know what tomorrow will hold.

7. Podcasts Help Build Friendships

I had the chance to catch up with Dragons’ Den Arlene Dickinson earlier in the year and I noticed something: 

Podcasts are a fun way to catch up with friends.

I hadn’t seen Arlene for a while and getting to have a conversation with her about what she’s learning and sharing what I’m investing my time into was very meaningful.

A lot of our podcast revolved around starting and scaling side hustles but we also covered some fun things like how I lost my finger as a 4-year-old and the value of endless curiosity.

8. Solve a Problem You’re Passionate About

On video calls with founders, I’m always asked what’s the biggest lesson I learned building Hootsuite. Usually, I come back to the same answer again and again which is: “Solving a problem you’re passionate about”.

If you are: deeply curious, fascinated by the industry and wanting to solve for users you care about, building a product will be 100x easier. 

If you are: building a product (just for) a profitable return, in an industry you don’t care about and have no relationship with the users, you’re gonna hate going into the office. 

9. A Passion Project: League of Innovators

I started League of Innovators in 2017 and since then it’s been firing on all cylinders. Over the last 12 months we have:

• Hired a new E.D. named Melissa Allen
• Graduated 250+ startups in our programs
• Seen nearly $1 billion of enterprise value created
• Launched a venture fund called LOI.vc to fund more founders…

10. Launching LOI Venture: Canada’s Newest VC Fund for Founders Under 30

Last week I announced a new project with Manny Padda. He and I are teaming up to launch a $20M Pre-Seed Fund focused on founders aged 15-30 attending the LOI Program.

We’ve already made our first investment in WFHomie within 48 hours of launching and have a blog if you’d like to follow our updates.

Biggest learning: life’s short. Launch projects that matter most to you. This is definitely one that hits the spot for me: supporting young entrepreneurs.

11. Take a Week Off When You Need It

Our team at Hootsuite shut down for a full week earlier in the summer to launch a company-wide wellness week. Here’s why:

We can’t run back-to-back marathons without burning out and our people need a break.

My question to you: how are you going to be taking a break this winter? What is your break rhythm going to look like in 2022?

12. Mountain Biking is Good for the Soul

Don’t believe me? Try it out.

I was able to soak up some mountain biking when my hometown of Vancouver wasn’t pouring buckets of rain and every day was a complete joy.

I can’t wait to get out more next year. Tweet me your favourite gear if you have any.

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That’s it. That’s all.

I hope you enjoyed my 12 takeaways from 2021.

Did one stick out to you? Share it in a comment below or tweet me with your favourite. I’d love to hear what you learned this year.

Wishing you and your loved ones all the best this holiday season. 

Happy New Year and I’ll see you in 2022! 🎉

Onwards,

Ryan