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World-Eaters: How Venture Capital is Cannibalizing the Economy. We are still locking down a date. But if you're interested, hit reply. 

MONTHLY METRICS

Accredited members: 1080 (+12%)
Unique investors: 324 (+22%)
Total Investments: 722 (+18%) 
Total Dollars Invested: $2.6M (+13%)
New Dollars Invested this month: $307K

June's stats look great.

• This is our 3rd official $300K+ month of investing this year!!! 

• We have two 6-figure wires going out to founders this week.

• LymeAlert is a few investments away from raising more on Play Money than even Play Money has raised. 👀

• Hello Divorce is closing with more net Angels.

This is exactly what we hoped for when we started Play Money. 

But I worry that some of this is just vanity metrics.

Over one-third of the dollars and sign-ups this month fall into the category I dismiss as tactical revenue — friends, family, and colleagues of the founders who aren't prospects to be repeat Play Money investors. LymeAlert brought them in droves! 

Having 87-year-old Uncle Frank from Western Mass navigate his first angel investment was a hoot. 

But, it didn't move the needle towards our goal of systematically minting repeat investors to turn Play Money into a billion-dollar fluid fund of permissionless capital redefining early-stage funding. 

Then we received an inbound message from the founder of Hello Divorce...

"[I want to offer] to do a quick video for founders about the benefits of working with PM - it’s been the smoothest Angel process I’ve ever experienced!"

Which reminded me of this inbound from Modern Rebel/Cheersy...

"You may not realize it, but [Play Money] fundamentally shifted my fundraising strategy.  A lot of people talk a big game on showing up for founders but you + your platform are the real deal." 

...and I rethought my "vanity metric" stance.

The founder is the product.

So everything that turns founders into advocates is strategic.

You know what's also 'not a vanity metric'?

For the 4th consecutive month, we've ended the month with more money in the bank than we started with. 💪

But the goal is not to "barely break even." It's to crack the code on minting repeat investors at scale.

Here's what we did and learned as we pushed down that path....

I'm still mildly obsessed by our monthly dollars per member. It's a synthetic metric and not actionable, but it provides a fair pulse on the business while we learn how to control the levers of the business.

JUNE WRAP-UP

• Launched an expanded sign-up flow built around qualitative data from scores of repeat Play Money investors; ran one test/iterate cycle.
• Revamped site instrumentation to make super-targeted emails automatic.
• Handled a ton of customer service issues.

In June we processed 110 investments, which included a 80%+ increase in 1st time investors from our previous highest month. 

Not surprisingly, we encountered every edge and error case with our KYC/money movement partners.  We hacked together tools for better visibility and smarter backend error checking, so we are better for it, but it hurt for a few days.

We made progress on our more strategic goals. Although it always feels too slow. 

Early results were encouraging:

• Retargeting campaigns appear to have boosted investment 20%+

• Feedback from folks who didn't invest inspired changes to onboarding.

• Tests with our weekly emails boosted engagement by 40%+.

And I totally geeked out on new insights that came from all this work. Most specifically:

• 70% of folks on Play Money dig into an email or a deal on the site at least once a month. 80% of those are engaging weekly; half are primarily through email. 

That includes 60% of people who signed up in 2024 and haven't invested yet, and 75% who signed up in 2025 who haven't invested yet. 🤯

TLDR: We have a LOT of dry powder in our existing member base. 

JULY LOOK AHEAD

• Make the expanded signup flow look "on brand"; direct existing members to it. 
• Launch 1st and 2nd investment email sequences built around psychographics.

• Build a dashboard that lets us know what's moving the conversion needle.

• Bonus: Get all our great content out of email and onto more public discovery platforms (in advance of more top-of-the-funnel activity)

If anyone has effectively used LinkedIn, Substack, or Beehiiv for top-of-the-funnel marketing or has cracked the code on AI as a top-of-the-funnel discovery engine, we'd love to talk. 

And yes, we'll likely bringing in some growth marketing help in the near future. 

Have a great holiday week.

-- C2K 💎

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