Robby
@amanda_robs
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Partner @cowboyvc investing in software infra seeds 🌱 II co-host @ossstartup podcast 🎙 II founder @themodernangels 💸
San Francisco, CA
Joined March 2020
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Pinned Tweet
Is your company ready for AI-powered phishing attacks?🧐
Since the launch of ChatGPT, there has been a 13x increase in phishing emails🤯
We look at this new wave of phishing attacks, the current anti-phishing landscape & opportunities for startups👇
5
6
45
Sharing some of the most common reasons we've passed on B2B companies at seed/pre-seed 🌱
👇👇👇
48
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1K
VCs & Founders:
Your friendly reminder that if a round is coming together, I have a list of almost ✨100 female & non-binary operator angel investors✨
&& they're some of the best-credentialed angels out there. Period.💪
⚡️DMs open!⚡️
66
97
1K
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 ✍️
40
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1K
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👇
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1K
Top cities to spend time this spring/summer:
1. NYC
2. NYC
3. NYC
anywhere I missed?
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1K
After 8 stressful years, your girl is finally a GREEN CARD HOLDER 🇺🇸🥹
This country still represents hope & opportunity to me and so many other immigrant founders, investors, and builders
Excited to continue investing in an American future ❤️
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Why do founders think their VC friends have all this money to angel invest🤔?
Homies, we're illiquid AF
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829
⚡️Founders looking for cap table diversity⚡️
I have ~30 extremely talented female / non-binary operators interested in angel investing
65
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749
Taking a $5M “seed” round instead of $1M - $2M won’t help you grow faster if demand isn’t there yet
51
40
703
For VCs looking to add diverse investors to their deals, I now have:
✨43 talented female / non-binary angel investors✨
As always... DMs open friends ☺️
29
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608
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 😉🧵
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❕VC friends❕
Your friendly reminder that we have a database of ✨97 female & non-binary operators✨ who are active angel investors
DMs open to yeah 😉
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Something tells me 2022 is going to be the:
💪Year of the Female Founder💪
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She’s a Cowboy… partner! 🤠
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A friend was told she wasn’t qualified for a job in VC.
👏To👏be👏clear - there are no set qualifications for VC.
Different firms look for different backgrounds & experiences.
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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👇
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VCs are well-positioned to add diversity to cap tables.
Recommend. Diverse. Angels.
I have a database of awesome female & non-binary execs who should get access to the best deals🚀
DMs open, VC friends!
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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✍️
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You’re a founder & your company is exiting
You’re creating life-changing wealth for your investors & that group is diverse, w/ people who will use this wealth to move their communities forward
I want every founder to be able to have this experience
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Pretty tired of the, "I care about diversity...but my whole cap table is white dudes" narrative
If you're a founder & don't know any diverse investors or angels feel free to DM me
I can make some intros
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And that wraps the most epic wedding weekend we could have ever asked for 💍🤍
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Distribution of wealth in silicon valley:
Male founders > become male angel investors > support more male founders 🔁
Let's break the cycle 😎
If you're a female or non-binary angel, hit me up 💪
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During COVID, my couple friends all got engaged and a puppy
My single friends all got bitter and a wine subscription
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✨There are now 50+ female & non-binary angel investors in our database✨
VC friends: would love to help you add these incredible 😇 to your deals!
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The up and coming female VCs are insanely impressive🤯
Very bullish on the future of our industry...
S/o to
@AllRaise
for being the community backbone💪
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Being single in your late 20s is accepting that any app with chat is a dating app
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So excited to announce our 2 new Cowboy funds totaling $260M of capital to support the next generation of incredible seed-stage founders 🎉😁💸
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Feeling so grateful for the best 30th birthday celebration I could ever ask for 💕✨
Sending love & gratitude to the friends I’ve made through Twitter the past few years - y’all are the best 🤗
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Following more smart women & underrepresented minorities on Twitter has significantly increased the quality of my feed 💫
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Releasing Cowboy's market map of the emerging generative AI infrastructure landscape ✨
Where are the biggest opportunities for startups?
What role will open source play?
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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
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Excited to announce our "Angel Investing 101" sessions for the 44 female & non-binary operators in our angel database 🥳
S/o to
@eladgil
&
@gilpenchina
for being our first 😇 experts
If you're a female or non-binary operator interested in angel investing, DMs open!
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Licensed to wed 🤗
Accepting any and all tips for the week before the wedding…
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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".
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*In general*, I'd define a pre-seed as:
Raising <$1M
Product in development, beta at best
Pre-monetization
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⚡️TOMORROW⚡️ I’m hosting an ‘Angel Investing 101’ session w/ the incredible ✨
@eladgil
✨
Female & non-binary 😇 slide into the DMs for an invite!
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👼Major "Modern Angels" Announcement👼
We just reached 180 female & non-binary investors🎉
Founders & VCs: this group is phenomenal - GTM execs, seasoned operators, product leaders & more!
You would be lucky to have them on your cap table 💪
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Can your open source company raise Series A?
We asked 18 of the top open source Series A investors what they want to see in order to lead a $10M - $25M round in today's environment
Here’s what they said 👇
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It’s awesome to see how many funds care about hiring women now (h/t
@AllRaise
) but so few are in leadership roles (GP / MGP / MD)
Waiting for the day senior men in VC will be willing to give up meaningful carry to give women major roles in their funds
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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.
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This is for the Female & Non-Binary Operators who have always wanted to invest, but didn’t have the access
👑Our community is for you👑
Spotlighting some of our incredible angel investors👇
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Celebrating 3 yrs at
@CowboyVC
🎉
Thankful to the BEST team - here’s to many more years with you as my cow-lleagues 🤠
Cc
@aileenlee
@Jillwillnyc
@allegra_v2
@twang
(+ our amazing EA Mae who’s not on TW 👑)
&& our incredible founders & community 🥰
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Given continued uncertainty around the fundraising environment, sharing 10 ways to increase 💸 runway without pitching VCs
THREAD👇
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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.
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Would love to see more female founders in infra software💪
Happy to spend time iterating on ideas with technical women considering becoming founders👩💻
DMs open ladies!
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Anyone else dying to hear more strong female / non-binary voices in tech…
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We’ve seen MANY incredible female founders lately
Ladies know that it’s time to build 😎
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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".
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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.
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BEYOND excited to host 100 female & non-binary operator angels at the Modern Angels Summit today
😆🤸✨🍾💃
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When multi-billion dollar funds do $100K checks into seed rounds, it just adds signaling risk.
If they want to lead your A, they can show value without being an investor.
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If biking through the streets of Manhattan at night isn’t magic I don’t know what is
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I wrote about an investment framework for evaluating early-stage developer tool startups in today’s environment
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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.
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For International Women’s Day, I wanted to give a shout-out to the ✨130+ female operator angels✨ who have joined our amazing community!
Female operators should get access to the same high-quality deal flow as male operators. Full stop.
DMs open if you want to join us 😇
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I started a new written series: Making Money from Open Source💸
The first post digs into one of the biggest challenges early-stage open source founders face - going from project-market fit to product-market fit👇
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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?
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Taking a moment to celebrate the growth in Modern Angels 😇
200 female & non-binary angels investing in the best venture opportunities 💪
VCs 👉 this group is for you to tap into!
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Y'all taking some major risks raising a ton of capital pre-product-market fit...
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The original 🤠
@aileenlee
is one of Forbes most powerful women!
On top of being a world-class investor, she has made our industry a more inclusive place helping countless women & underrepresented minorities find their voice 💪
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12/ trusted ally
Finally, being an early-stage founder can be a hard and lonely job; having someone you trust to bounce ideas off of and RIFF with can be super productive (& help keep you sane 🙏)
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You can’t get more Canadian than getting featured in Canadian Business Magazine 🇨🇦
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2 years in and couldn’t be prouder to be part of such an incredible group of investors & founders 🥰
Love my 🤠 team!
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Smart people score their result, smarter people score their process
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One of the biggest challenges open source founders face is determining the right business model💰
We dig into the history of open source business models (starting w/
@RedHat
), Open Core and Cloud Hosting models, and managing community expectations here👇
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Software infra has been hit hard in 2022 - the avg public co is down (40%)🤯
However, downturns are a great time to build & we at
@CowboyVC
are excited to find the bold founders taking this time to identify new opportunities💪
Some ideas from us here👇
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For female & non-binary angels: there are opportunities to deploy smaller checks (i.e. $5K) as more founders are prioritizing diverse cap tables
👉amanda
@cowboy
.vc w/ LI, check size, industry pref, investments (if any) & value-add to get looped in
Deals in the works already😎
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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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I get y’all hate SF but this city is damn beautiful when it’s 70 & clear✨
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It's been heartbreaking to read about what went down at Launch House. I'm so sorry to all of the women who had to experience awful things there. I see you ♥️
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Founders: we heard you 😇
My amazing 🤠 intern
@mathurahravi
created a process where founders can submit pitches to the female angel group to check out. No warm intro required!
Link here 👉
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At
@CowboyVC
, we often work with technical founders on GTM
@tnachen
& I interviewed the founders of
@thekonginc
,
@LightstepHQ
,
@HashiCorp
,
@LaunchDarkly
,
@algorithmia
, &
@D2iQ
on taking on their first 'Enterprise Dragon' 🚀
My top takeaways below👇
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I feel so understood by my team 💖
Barry’s classes + Levain cookies = the best gifts ever 😂💪
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1/ At
@CowboyVC
we’re excited about DevOps and used data from some of the leading DevOps companies to gather insights on how to build great teams
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The venture industry hasn't always been accepting or kind to women.
When I started in venture 5 years ago, organizations like
@AllRaise
didn't exist. The women I knew in the industry often felt excluded and were frequently the only woman in meetings and board rooms.
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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)
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Blown away by the up-and-coming VCs 🔥
&& this group is SO much more diverse vs when I started in venture 5 years ago
Huge s/o to orgs like
@AllRaise
@BLCKVC
@LatinxVCs
who make our industry more accessible to incredible diverse talent ✨
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Outside of growth, most important KPI is ✨CHURN✨
And it comes in 4 flavors 💁♀️:
1/ Gross ARR (or MRR)
2/ Net ARR (or MRR)
3/ Gross Logo
4/ Net Logo
@jomayra_herrera
wants me to try to be funny but I’ve chosen my path as an aspiring
#thoughtgurl
🦸♀️
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The kindest, most welcoming ppl I’ve met in venture have generally been women & URM; thankful for y’all 💕
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A MASSIVE congrats to our new Partner
@Jillwillnyc
🤗❤️🥳👑💪
You’re a core reason
@CowboyVC
is the absolute best place to be an investor!
Sending you so much 🤠❤️
1/ Super excited to share the very awesome
@Jillwillnyc
is our new Partner at
@CowboyVC
🤠! Pls send her 🎉💝...
& learn more about how awesome she is here (cc
@twang
@amanda_robs
@allegra_v2
)
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0
1
66
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?
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8/ Champion is unclear
Does your product span multiple departments (engineering + data + security)? What is the buyer/user dynamic? Whose budget will you come out of? Who will be required to implement and maintain your product?
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65