Hey Contrarians,

If you’ve ever wanted to invest with us, this email is for you. (It’s also time-sensitive, so read it as soon as you can.)

So, I talk a lot about owning and investing in small, boring businesses. Last year though, we saw a different opportunity to layer in. One with even bigger potential: Launching a venture capital fund called Contrarian Thinking Capital.

The goal? To also invest (with YOU) in the startups powering tech evolutions across small business, investing, freedom, and more. Think car wash + modern software (wink wink, Shopgenie).

Boring businesses for not-so-boring returns. It’s all part of our master plan. Today we have updates on our progress and, possibly for the last time, details on how some of you can be involved in the next step...

Today in 5 minutes or less, you’ll learn:

✔️ TLDR: What you should know

✔️ Fund no-background: Media + Money + Machines + Small Biz

✔️ Our 3 secret weapons (you’re one of them)

✔️ A peek into our 16 investments so far…

✔️ How you can invest in the fund (until it hits its target)

TLDR: What you should know

I’m just gonna sum everything up for you right here: Our fund is raising an additional ~$5M and we’d love to see some of you invest if eligible. (Either way, this email should be a cool inside look into what we’ve been up to.)

Since we launched the fund last year, we’ve partnered with 16 tremendous founders and their startups (now collectively valued at $1.2B+). We’ve also confirmed that there’s a massive opportunity in “boring” tech with a small biz focus that we’re uniquely positioned to capitalize on (more on that in a bit). 

This capital will allow us to support more founders building for the next generation, especially those making a difference for small biz’s and their employees.

So feel free to check out the fund website (and fill out the “invest now” prompt if you know you’re interested), then come back to learn about our secret weapons, growing portfolio, and the details and risks involved in investing in this fund.

Background: Media + Money + Machines + Small Biz

Between myself, our media, and our biz-buying community, I’ve seen two trends happening across small biz acquisitions:

1. Retiring business owners are increasingly trading hands with the next generation.
2. As the next gen takes over, they’re bringing tech with them.

To me, tech + boring + 33M small biz’s (many of which will soon sell) = BIG opportunity.

At Contrarian Thinking, our goal isn’t just to invest in the laundromats, cleaning companies, and car washes of the world (and educate others on how to do the same).

We want to invest in the people building tech that takes these biz’s to the next level. The companies so innovative, that either their direct or indirect impacts on Main Streets can be truly profound.

By risking capital for these startups, we get a chance to own a piece of the future that may power businesses we love. We get a chance to have more skin in the game.

(And for the next couple of weeks, you might have a chance, too…)

Our secret weapons: You’re one of them

In a world where capital is a commodity, we have an unfair advantage. For starters, we do 3 things differently than most early-stage investors I see:

1) We’re building a top independent media and education brand in the small biz investing space. That means we can often assist with access to a top-of-funnel audience, small biz expertise, and even customers. Companies, top-tier VC’s, and other investors recognize this, too, and we’ve attracted impressive inbound deal flow as a result.

2) We find the beauty in the rough and boring. We prefer getting our hands dirty looking at the opposite of social apps, crypto, and the next tulip bubble. We aren’t looking for flashy PR stunts, we’re looking for profit-driven companies that quickly refine, commit, and deliver.

3) We think like owners, not venture capitalists. That’s because we are owners working on our own businesses, too. We know growth is paramount, but not at all costs. When we structure deals, we try to coordinate for additional upside based on the value we deliver.

Alright, and with that, it’s time. Drumroll, please…

A peek into our 16 investments so far...

Since that flashy GIF up top with a bunch of random names, colors, and logos means absolutely nothing to you, here’s a sentence on each (in no particular order because I don’t pick favorites):

• ​ShopGenie: The auto repair industry needs a time machine to take the customer experience to 2023, and this is it.
• ​Figure: You may be wondering why the heck we invested in humanoid robots. Five words: Labor shortages and worker protection.
• ​Nuvocargo: Nuvocargo’s US-Mex trading platform offers freight forwarding, customs brokerage, cargo insurance, and supply chain financing.
• ​Percent: Unlocking private credit deals for accredited retail investors via an easy-to-use platform. Helping folks invest like the institutions do.
• ​Beehiiv: Making building, growing, and monetizing a newsletter easier than ever.
• Numeral: Sales tax compliance is one of the most frustrating hoops for ecommerce biz’s to jump through. On Numeral, it takes <5 minutes.
• ​SkyFi: On-demand access to Satellites for all kinds of people and biz’s. Like Google Earth but way more robust and in near-real-time.
• ​Blindspot: The easiest way to advertise on billboards, making large-scale marketing possible for biz’s that otherwise couldn’t manage it.
• ​Ladder: A personal training app that centralizes access to some of the world’s best coaches for busy people who prioritize fitness. Huge fan.
• ​PostPilot: Leading the way in helping modern businesses send personalized, profit-generating direct mail.
• ​Here: Making it easy for anyone to invest in vacation rentals like stocks for as little as $250. (And they have scaled quickly.)
• ​Heatmap: Heatmap’s platform attaches precise revenue insights to website user behavior. The long-term goal? Self-optimizing websites.
• ​Release: All-in-one platform for simplifying multifamily real estate financing and banking, whether you own 2 units or 2k.
• ​Saronic: Autonomous vessels for emerging challenges at sea (aka badass boats for the DoD). The tech may one day have huge implications spanning the logistics and shipping industries.
• ​Basket: The ultimate ecommerce solution for consumers, bringing products from 100k+ stores into one organized list that tracks prices.
• ​Hone Health: Personalized care, insights, medications, and licensed physician consultations for men, all from home.

That’s our portfolio to date. 16 companies. Some are already profitable. The cool part about this is that if you invest in this fund (which we’re about to tell you is open), these companies are already in the portfolio.

How we invest (in plain English)

Here’s the thing about VC. It’s a totally different animal than investing in a small biz. To close a fund in the green, you can’t focus on reliable base hits. You need a couple of grand slams and it takes some time.

So here’s what we look for...

There’s no perfect formula, but if I had to list out what we tend to go after, it would be a company that:

1. Isn’t just an idea. It has a product with months of data (at least).
2. Has founders who have lived the problem they’re solving.
3. Has a well-rounded team across tech and business operations.
4. Has some funding already committed.
5. Has a clear plan for how they’ll deploy the capital.
6. Can point to specific metrics highlighting traction and growth.
7. Is on track for $100K to $10M in annual recurring revenue.
8. Has a large or growing total addressable market (TAM) and is building products to solve issues that have pervaded small businesses or “boring” industries.

Typically, we look to back founders raising equity at the pre-seed or seed levels, with our check sizes varying but usually ranging from $100k to $250k. Depending on the team, traction, and lead investors, we’ll occasionally invest in later rounds.

We also reserve some capital for secondary investments in companies that have established product-market fit. (This would have included opportunities like Pipe, Robinhood, and Homebase, and yes, I am still kicking myself for not investing because they were too late stage.)

Now my favorite part: How you can be involved

When we first opened this fund, we opened the door to those of you eligible to come along for the ride. Now, after our first 16 investments, we’re swinging that door open again. Some quick notes:

• You must be an accredited investor. Here’s what that means…
• 20% net carry: Carry is earned only if the fund is profitable.
• The minimum Commitment is $50k over 2 years but you will be prompted for 75% of your investment upfront ($37,500).
• The fund has a 2% management fee (2% annually over 10 years).
• We will close the door for commitments as soon as the fund target is met. First come first served. We’re raising a relatively small amount (~$5M), so we expect this to close fast.

🚨 The Adult Section 🚨 Investments can go to zero, and surely some of them will. We’re making long-term bets on the future of SMBs, the economy, technology, and consumer behavior. Expect us to do everything we can to pick companies we think will win.

Venture capital is a potentially rewarding long-term game. We’re looking for long-term people. If you want to learn more about the fund and get involved, head on over to our website by clicking the button below. Once you’re there, select “Invest Now.”

I signed off with this when we launched the fund last year, and my message hasn’t changed:

“I structured this in a way where I know that in 5, 10, 15, and 20 years from now I’ll still want to be betting on the future of business owners to make our world better. This selfishly is where I want to put my money.

After all, ownership is the key to wealth, I hope to open the doors to becoming an owner to more humans. I hope to help bring more companies we want to exist to our audience and to the world, one tiny little check at a time. 🙂

And for our founders, I hope to beat you up if you get ridiculous on your valuations or terms. Stick with the Silicon Valley VCs for blank checks. Let’s do this.”

-Codie

What’d you think of this week’s newsletter? Hit reply to let us know!

“That’s what it means to be an owner. To have skin in the game.”