Hey Friend 😊 

Today, instead of our typical founder deep dive I’m going to share more about this newsletter, looking back at what happened this year, some of my favorite editions, what’s next, and how you can get involved.

I sent the first edition of this newsletter to a few hundred friends in December 2022, published my first founder deep dive about Sam Altman in February 2023, and in May I quit my job at VITALIZE Venture Capital to work on Just Go Grind full-time.

Since then, this newsletter has grown to more than 23,000 subscribers, I’ve published 45 founder deep dives (several free podcast versions) and generated tens of thousands of dollars in revenue through a combination of sponsorships, a premium subscription, and affiliates.

It’s been, as expected, a grind, but I’m so happy I took the leap.

I’ve thoroughly enjoyed learning about so many different world-class founders as well as how to build a media company. Spoiler—I still have a lot to learn.

Thankfully, I’ve met some incredibly helpful people along the way who have been willing to share their insights. By the way, it’s much easier to find those people, and they’re much more willing to help you when you’re in the game.

Looking back at 2023, I’m proud of the work I published and with those 45 founder deep dives I wanted to share with you a few of my favorites.

Let’s get to it.

My 5 Favorite Founder Deep Dives

It’s a nearly impossible task to pick my favorite editions, each one takes so much time and energy and is unique in its own way, but I do have a few that stand out.

Tope Awotona's Unwavering Determination: How He Built Calendly Into a $3B Company

Tope Awotona invested all of his savings and maxed out his credit cards to build Calendly and I respect the hell out of anyone willing to bet on themself like that. His story is simply remarkable.

The Relentless Resourcefulness of Sara Blakely: Turning $5,000 Into a $1.2 Billion Company

Sara Blakely is such a creative entrepreneur, not only with her products but with her packaging and distribution. When I think of someone being relentlessly resourceful, Sara is one of the first people that comes to mind.

Tyler Perry: The Prolific Billionaire Media Mogul: How He Went from Homeless to Creating an Entertainment Empire

The creative production of Tyler Perry over his career is staggering. By 2020 he had already produced a total of 1,200 TV episodes, 20+ feature films, more than two dozen stage plays, and even two New York Times bestselling books. I love learning about founders who are prolific over an extended period of time like Tyler has been.

The Wisdom of Patrick Collison: Building Stripe Into a Multi-Billion Dollar Payments Behemoth

Patrick Collison is perhaps the most well-read founder I’ve studied so far and it shows. He’s brilliant and I was able to capture a fraction of his insights in this edition.

Travis Kalanick's Relentless Ambition: How the Uber Co-Founder Built A $68 Billion Empire

One of the most controversial founders I chose to cover this year, right up there with Dave Portnoy, Travis Kalanick’s story is well-documented and yet I was still able to find more gems in my research. I couldn’t pass up the chance to research a founder who created one of the most iconic tech companies in the world and his story didn’t disappoint.

What’s Next

First of all, I’m going to continue to write about world-class founders like I have been. I’m obsessed and it’s been so much fun.

If you have a world-class founder you’d like me to cover, please let me know in the form linked below:

After building a solid foundation for the Just Go Grind newsletter in 2023, I’ve been mulling over my options for the last few weeks for what’s next.

The newsletter will continue regardless of what option I choose, but I’ve tried to think more deeply about what I want from this business, whether I want to continue being a solo operator, and whether this newsletter is a door to another opportunity.

Candidly, the answer hasn’t always been clear.

Some options I’ve been considering:

• Continue to bootstrap Just Go Grind

• Raise money to accelerate the growth of the business

• Join a VC firm in a community or marketing role and write on the side

There are several reasons why I’d consider each path. One thing I’ve learned from growing this newsletter is that there are certain thresholds, let’s say 40,000 or 50,000 subscribers, which make it easier for ad agencies and sponsors to work with you.

Getting to that critical mass of subscribers seems to be a tipping point of sorts if you’re going down the ad-supported path.

With this newsletter at 23,000+ subscribers, we’re a bit short of that right now, but there are plenty of other opportunities to monetize through memberships, digital products, and events - things I’ve thought a lot about the past few weeks and which I’ll almost certainly be implementing in new ways in 2024.

Raising funding for Just Go Grind is a path I’ve also been seriously considering in the past few weeks.

While I don’t see Just Go Grind as a VC-backed startup like a lot of tech companies, raising money, potentially a mix of debt and equity, would provide an opportunity to accelerate audience growth and pursue other potential avenues like YouTube and podcasts as well as a few other ideas I have, making this into a very profitable cash-flowing business.

If you’re at all interested in learning more about investing in Just Go Grind if I ever decide to go down that path, fill out the form in the link below:

Finally, in 2024 I’m planning to roll out some new series in the Just Go Grind newsletter.

I’m still finalizing what these will look like, but two options include:

• A short email sharing just the insights from the founders I cover

• An interview “Q&A Series” sharing tactics and strategies from founders at different stages

If you’re interested in being featured in a Q&A style series at some point, please fill out the form in the link below:

Thank YOU!

Of course, I have to give a big THANK YOU to… you.

You made my dream of running my own business possible by reading this newsletter.

I hope you have a happy holiday!

Best,

Justin