Last Cast Letter #36: What An Idiot!

Hi All - Happy Thursday. It’s the last day of the month, which means it’s time for the Last Cast Letter.

Guess what tomorrow is?

Such a good GIF. You only get to use it 1x per year, so glad I got that out of my system. On a more important note, I’m excited to update you all on a new vertical we’re quietly launching.

It’s called Walk-On Ventures, which will provide early-stage investment opportunities for actively investing accredited individuals. That’s a mouthful. Let’s break that down:

• Early-stage opportunities: These are private investment opportunities ranging various stages, anywhere from early-stage to pre-IPO. Think venture capital, which can sometimes mean seed-stage investments or late growth stage opportunities. 

• Actively investing: we’re looking for individuals who are aiming to deploy capital within the next 6-12 months. 

• Accredited individuals: An accredited investor is an individual or entity permitted to invest in unregistered, high-risk private securities because they meet SEC financial criteria. Qualifications include a net worth over $1 million (excluding primary residence), annual income over $200,000 ($300,000 with a spouse), or holding specific financial licenses (Series 7, 65, 82)

If this general concept sounds interesting already, and you fit all 3 of the criteria above, click here to fill out our survey. 

If you qualify, you’ll be directed to my calendar to schedule a call. The call is a mandatory part of the process, given the confidential nature of some of the deals we are working on.

If you're curious why I’m interested in building this vertical, well then, here’s a slightly longer story:

When I left Blackstone in 2018 to work on building a "newsletter", more than a handful of people looked at me like I had three heads. 

"This guy is an absolute idiot", is 100% what many people were (slash probably still are) thinking. 

And who knows, maybe they're right because this story is far from over.

But the decision to leave Blackstone set me down a path that I don’t think I would have taken had I not made the jump. 

As a result, it opened up doors and opportunities that I don’t think I would have gotten otherwise. 

For example, when I first started working on The Street Sheet, I used an ESP, or “email service provider” called Mailchimp. It wasn’t bad, but it definitely wasn’t great. In fact, as the audience grew, I became increasingly frustrated with Mailchimp. So I switched. Then I switched again. Then again. Then again.

I soon realized that every ESP stunk. Poor customer service, poor design, poor automations, poor analytics & reporting. The list went on and on, and quite frankly, I felt like I was hitting a wall.

As timing would have it, however, I had recently become friends with a guy named Tyler Denk. Tyler was one of the earliest hires at Morning Brew and was responsible for building what was basically an in-house solution to all of the problems I described above. 

After a brief stint at Google, Tyler was itching to build his own company, so we met for beers in Midtown Manhattan to talk about it. His new company was going to be called Beehiiv, he told me. And the vision was to build and expand upon what he had created at Morning Brew to make Beehiiv the de facto leader in the ESP space. 

After outlining all the problems I was having with the other 10+ ESPs I had tried, he invited me to be an early Beehiiv user with The Street Sheet. My experience with every other platform had been so horrible, I said sure, what the heck. I had nothing to lose. 

So we moved our list over to this fledgling platform and clicked send on our first campaign. I had an immediate “ah-ha!” moment. It felt like the Joe Rogan reaction below. 

The deliverability was fantastic, the design was sleek and intuitive, and the campaign metrics were not only insightful but also just aesthetically pleasing.

From a customer service perspective, I could text the CEO and tell him what I liked and didn’t like. I can still do that TODAY, although I try not to bother Tyler as much. That said, they have a robust customer service team that responds to our questions and requests within the hour.

Beehiiv was and continues to be a literal night and day difference when it comes to operating our “newsletter” business. So here’s where it gets interesting and how it relates to Walk-On Ventures.

After using Beehiiv for a few months, Tyler reached back out to let me know that they were raising a seed round to help scale the business. 

He wanted to know if I’d like to invest. It was an immediate yes for me. Not only because the platform was so much better than everything else on the market, but also because I knew Tyler as a builder and founder and believed in him immensely. 

So I cut my first venture check into Beehiiv. A little over a year later, Beehiiv raised a $12.5 million Series A round in June 2023. Then, in April 2024, they raised another $33M in a Series B round. 

For context, one of Beehiiv’s biggest competitors is Substack. Last summer, Substack raised $100M at a $1.1B valuation.

I am extremely and transparently biased, but I truly think that Beehiiv blows Substack out of the water. 

Remember the part of this story where I tried like 10+ ESPs? Substack was one of those. We tested it with a small hockey newsletter I was running at the time called Pregame Skate. 

Substack felt extremely limiting in a lot of ways, so we ended up moving this newsletter to Beehiiv as well. 

What does this all mean? 

Well, let’s bring it all together. On paper, this Beehiiv investment has done well. I’m totally aware that these paper gains can vanish overnight because venture investing is inherently risky. 

That said, it’s an investment that I never would have gotten access to had I not left Blackstone. And it’s been fun to be a part of, so naturally I went looking for more.

To the second part, I have been working on a handful of venture deals to get more exposure to the asset class. As a result, I’ve met some incredible partners and built a growing infrastructure to source deals, vet founders, and invest on a one-by-one basis via SPVs.

This has all been done with a select group of people. Now it’s time to slowly expand and bring more interested parties into the fold. So, to reiterate: if you are an

• Actively investing

• Accredited individual

• Who is looking for early-stage opportunities

… I would love for you to apply to join. Fill out our survey and schedule a call, and we’ll take it from there. Looking forward to it.

— Brooks