This is kind of on the DL, but Tiny has made $10MM+ in venture investments over the better part of a decade.

Mostly just for fun. Our day job has been buying whole companies, so it’s a side hustle.

We think of it as a way to pay it forward and back friends we love.... 👇
In 2021, we’re taking our early stage investing more seriously.

As it turns out, when you have smart friends, investing in them goes well....
We’ve been lucky enough to invest in great companies like @Pitch, @Buffer, @Squarespace, @SpaceX, @Superhuman, Waking Up, and 30+ other awesome companies...

tinycapital.com/companies

(Click on Venture Investments)
While most venture investors have to hit the pavement and hustle to get deals, we’ve had three unfair advantages:

1.A big Twitter following and reputation

2.An openness to profits/cashflow vs. growth at all cost...
3.Owning some of the world’s top digital agencies like @metalab, @z1digitalstudio, @doubleupgrowth etc: meta.inc

All this has resulted in in us getting bombarded with deals, often with preferential terms because they want us in the round or to use our agencies.
Power law dictates venture investment outcomes. The top firms do the best because they get the best deals.

It’s a positive feedback loop:

Founders bring the best opportunities to Sequoia, Accel, Benchmark, Andreesen, etc, so they perform the best....
The same thing happens with design firms. They gain a reputation, and founders want access.

Over the past 15 years, MetaLab has become known as one of the top product design agency in Silicon Valley, helping design and engineer early versions of many now billion-dollar companies
As a result—similar to a top tier venture firm—many of the world’s best founders and startups want to work with MetaLab.

We get a first look and, usually, an opportunity to invest.

For example: some of MetaLab’s former clients include Coinbase, Pinterest, Shopify, and Slack...
Unfortunately, we weren’t doing venture back then, otherwise I’d be writing this tweet from the plush seat of my Gulfstream!

Today, we are making a few moves…

We are excited to announcing the Tiny Rolling Fund.
Yeah, yeah. I know. Everyone has a stupid rolling fund.

But ours is unique in a few ways:

1. We will be the largest investor at up to $2MM/year (significant skin in the game)

2. We will not be charging management fees or costs, only a carry (we win when you win)
3. We will be bringing our value approach to venture and investing in a wide range of opportunities: everything from cap table recaps, to cashflow focused bootstrappers looking for flexible growth capital, to traditional venture investments in companies we are excited about.
While it’s a bit of a meme to have a rolling fund, we think the alignment, unique deal flow, and flexible approach offer something a little different.

It also allows us to make some higher conviction bets and bring some friends along for the ride.
If this sounds interesting, we’d love to have you as an investor.

It’s super simple, just click on the link below and fill out the form, it takes about a minute.

You can commit as little as $5,000 per year by clicking here: angel.co/v/back/tiny-ro…
Would love to have you. 150 spots are first come, first serve :-)

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More from @awilkinson

23 Mar
One of the hardest things to balance as entrepreneur is WHEN to hire.

Hire TOO FAST and you end up with:

Toxic culture misfits 🤡

Middle management 👨‍💼👩‍💼

Parkinson’s Law: 🤼‍♀️

“Work expands so as to fill the resources available for its completion”

TLDR...
Your company gets does the same amount of work as before, way less efficiently.

Sometimes way SLOWER due to committees and too many cooks in the kitchen.

On the flip side...
Hire TOO SLOW and your life becomes a living hell 👹

You become Lucy in the chocolate factory, barely keeping up 😖

Your time gets consumed with unimportant tasks and decisions that are way below your pay grade 😩

And you don’t have time to be strategic or spot ice bergs 🗺
Read 6 tweets
18 Mar
Most founders are scared of marketing.

They think it's douchey.

Instead, they do Field Of Dreams marketing:

"If you build it, they will come".

They won't. You need marketing.

The problem is, most marketers are aggressive.

They think in clicks and funnels, not brand...
For years, we hired marketing agencies who would embarrass us with cheesy and overly aggressive tactics.

So, we stopped doing it. We focused on organic growth, and in many instances it meant that we lost out on huge opportunities to well funded and better marketed competitors...
This was profoundly stupid.

Finally, we came to our senses and, infomercial style, said "there's got to be a better way".

Last year, we co-founded @doubleupgrowth with @aidanhornsby to create a growth marketing agency that focuses on marketing great product tastefully....
Read 5 tweets
15 Mar
One of the most impactful things I've done in the past 10 years is join a business forum.

Every month, I sit in a room and pour my heart out about my business and life problems to a group of 5 other entrepreneurs.

It's the same group every time and it's 100% confidential...
I have multiple groups and do one most weeks for the past 10 years.

I've been in groups with people who run popsicle businesses, puzzle companies, woodworking shops, tech companies—you name it.

Entrepreneurs have oddly universal problems and I've learned something from everyone
We've helped one another navigate:

- Failed business partnerships
- Bankruptcies
- Divorces
- Fraud
- Health scares
- Lawsuits
- Exits
- Toxic employees
- Mental health issues
- Deaths in the family
- Issues with kids

You name it, we've dealt with it and learned as a group...
Read 5 tweets
15 Mar
So this oil prospector dies and goes to heaven. At the gate, St. Peter reads the account of his life and tells him that he's qualified for heaven, but there was a problem

"See that crowd over there? They're all oil prospectors who've arrived before you".... 👇
"And the way things work here, you can't get in until after them. So I'm afraid this looks like a long wait for you."

"Not a problem," replies the man. "I know how to get rid of that crowd..."
So he turns towards them and shouts, "Hey, did you hear? Oil has been discovered in hell!"

And sure enough, as soon as they heard him, every single one of them ran off towards hell....
Read 4 tweets
26 Feb
Every designer/developer in the world:
Read 4 tweets
26 Feb
One of the hardest things to figure out:

Do you want to chop wood (individual contributor) 🪓

OR

Build a sawmill (start a business) 🪚

Chopping wood is tiring but satisfying labour. You can work quietly and get into a flow state.

But...
It's 100% dependent on you. If you get sick, you can't chop wood, and therefore your income dries up.

😫No breaks.

🙃No delegation.

🤦‍♂️Limited to your personal output.

💸Hard to get wealthy.

On the flip side...
Build a sawmill and you can delegate.

Build systems.

Have others eventually do the work.

You can massively increase your output and become wealthy.

But...
Read 5 tweets

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