Robby Profile picture
Sep 15, 2020 9 tweets 3 min read Read on X
After ~1 year at Cowboy focused entirely on seed, my frameworks for investing at this stage have changed.

Still (and forever) learning, but sharing my current thoughts on seed investing ✍️
1/ Founder > market

Investing at seed often means investing when the market opportunity/size isn’t clear. I believe it’s more important to invest in amazing founders than amazing market opportunities*.

*network effects businesses excluded
2/ Partner w/ "Learning Animals"

I picked this one up from the queen of coining new terms @aileenlee. Founders with a growth mindset can adapt to changing market dynamics & develop into successful leaders at different stages of growth.
3/ Build for tomorrow

Founders at seed are building for tomorrow's world, not today's. They need foresight grounded in a deep understanding of the tech & market forces driving change.

This is framed very well by @m2jr in his piece on "Backcasting".

medium.com/@m2jr/how-to-b…
4/ Diligence should not convince you to make an investment

Using diligence to move from "no" to "yes" is dangerous. It can result in projecting a vision on founders that isn't theirs.

S/o to @twang for keeping me honest on this point.
5/ Why (this founder) now?

I used to obsess over “why now” but have edited that to “why this founder now”. At Cowboy, we look for 'earned insights' that demonstrate a founder's unique understanding of their space in addition to the tech/market trends supporting "why now".
6/ Find talent magnets

This extends to advisers, early engineers, other investors, and any other high-quality ppl the founders have convinced to spend their precious time helping them. This can be a huge point of leverage early-on.
7/ Invest in products w/ a fast 'time to wow'

This is so important for seed-stage companies to drive early adoption, usage, & customer/community love.
8/ Back companies that can get to Series A

Our companies usually raise multiple rounds & need to hit milestones to raise more $.

At Cowboy, we consider this in diligence & do an all-hands session post-investment to fine-tune milestones & have a path to get there (hiring, etc.)

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More from @amanda_robs

Jan 28, 2021
What qualities do the best founders have?

At seed, I believe being able to identify outstanding founders is more important than being able to identify outstanding market opportunities.

Sharing 10 things I’ve learned to look for below👇
1/ Can clearly articulate what success looks like

Founders who have a vision for where we want to be in 5 years.

They have a pointed view of the future & how their company will fit into it.
2/ Are ruthless prioritizers

Founders who won’t get bogged down by the demands on their time & can focus effort on what matters for the success of the company.

@Spotify CEO @eldsjal is known to aggressively manage his time👇

(found via @ProfileRead)

fastcompany.com/90213545/exclu…
Read 11 tweets
Dec 9, 2020
Sharing some of the most common reasons we've passed on B2B companies at seed/pre-seed 🌱

👇👇👇
1/ Depth of understanding of the problem space isn't clear

Why are you the best founders to build in this space? What's your unique insight? Why are you willing to spend the next 5-10 years focused on this problem?
2/ Massive company vision isn't there

What north star are you tracking towards? If you're successful, what will the company have accomplished in 5 years?
Read 10 tweets
Oct 6, 2020
At 🤠, we spend a lot of time with our seed companies on their Series A pitches. While most founders have a good sense of what needs to be in it (comp matrix, P&L, etc.) many miss the narrative top Series A firms look for.

Sharing views on a strong Series A pitch below✍️
1/ Proof of the billion+ opportunity

By Series A, you should have early data points that support a massive market opportunity (deal sizes, volume of deals, etc.). The picture may not be 100% clear, but there should be market feedback driving you to raise more venture capital.
2/ Clear framing of the “why now”

Seed investors are used to raw pitches. The presentation style is more conversational and we often discover the founder's perspective on "why now" through an open discussion. By Series A, this narrative needs to be clear and in the pitch.
Read 9 tweets
Jul 8, 2020
The past few years I've sat in a number of board rooms and watched some founders thrive and others struggle

Sharing some tips, particularly for first-time founders, on how to best run board meetings

Oh - and it's a THREAD 😉🧵
1/ Focus on a few strategic topics - leave general updates to a pre-read, board members can ask questions on those if they have them
2/ Use your board observers - most are dying to be helpful so whether it's taking notes or helping with one-off requests, ask them!
Read 11 tweets
Jun 30, 2020
Founders often ask about the value early-stage VCs can add

Reflecting on 4 years in venture, I’ve found it generally falls into the below categories

THREAD👇
1/ strategic advice

VCs work with multiple companies and have seen them through different stages of growth; they can share learnings to augment your strategy and prevent you from making the same mistakes as others (we advise a lot on GTM)
2/ future financings

Early-stage VCs will have relationships with later-stage VCs so have a sense of the milestones needed for a successful future raise; they can also advise on the best firms/partners for your space
Read 13 tweets

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