Brian Nichols
@b_nicks11
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Founder of Angel Squad @hustlefundvc | Invested $50M+ leading syndicates & helped others do the same | On a mission to make angel investing accessible to 10k+
Join 2000+ angel investors
Joined November 2019
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1/ I’ve become the go-to guy for anyone starting a “tech mafia syndicate” -- and I’m not mad about it. Tech mafia syndicates are groups pulled together by current/former employees that invest together in startups where we think we can add value (all of us use
@angellist
).
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@gokulr
Strong disagree on giving this blanket statement as advice.
For some people (like me) this process doesn’t work. Be impatient. Find the place where you feel most aligned and valued. Where your work is high impact. It’s very hard to know this from 2 on-site interview days.
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I hate when pre-seed and seed-stage founders trick themselves into thinking that they’re doing real work.
Lots of the “progress” I see in investor updates are what I’ll call “fake work.”
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I am so freaking excited to invest in startups this year.
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A founder just made my day.
He mentioned that I was the first believer in his startup and that he remembers where he was sitting when he got the confidence boost from our call that made him think "wow...we can do this." His company is on 🔥.
I take zero credit & I 💛 this job
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So what’s the real work?
• Talking to potential customers (discovery)
• Building and improving the product (retention)
• Hacking together distribution channels (customer acquisition)
• And ultimately, getting customers to pay for the product (revenue)
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This is such outdated advice.
You do you, fam.
DON’T BE JUMPY
Got this message from a CEO about a candidate: “I don't think they'd be a good fit. We have a pretty hard rule on no jumpy folks and their background looks like a alot of 1.5 years and then gone”.
Current and future job seekers: don’t be jumpy. Accomplish
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🍾Some personal news🍾 :
I’m thrilled to share that I’ve joined
@HustleFundVC
.
🧵about how a community of some of the great people in VC helped, and how the VC landscape has started to embrace operator angels -- because it has to.
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VC terminology is just too confusing.
It's a steep learning curve for founders and angels.
Here are 8 more VC terms you should know:
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Founders & operators who are also angel investors are the most useful people for founders to talk to. They have your back, especially very early on your journey.
Would recommend every founder chat with at least 2-3 of them before chatting with your first VC.
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💥ANNOUNCEMENT TIME💥
Hustle Fund and I have been quietly building a program for *new* angel investors 🤫.
New angels are an overlooked group that often punch WAY above their weight. We're bringing more of them into the fold 📈.
It's my pleasure to share with you: ANGEL SQUAD
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Calling it now: The next "thing" in venture will be small marketing consulting companies raising small funds to invest in their top performing clients.
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I was catching up with a friend of a friend this weekend.
His company raised $100M+ at a $300M+ pre-money valuation.
They're at $10M in ARR today. Burning $3M/month.
"The next 18 months are do are die" 😓
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VC Terminology is intimidating.
There are so many, and it's overwhelming for angel investors and founders.
Here are 10 investment VC terms to make it a little more accessible:
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Have you heard of Mike Walsh and Oren Michels?
They both invested $5,000 into Uber’s seed round.
Any guess as to how much that $5000 turned into?
~$25M.
A ~5000x return.
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Bootstrapping doesn’t get as much praise as it should.
Now, I’m an angel investor.
I love investing.
And I love companies that fit the venture model.
But bootstrapping is no less impressive than companies that raise big venture rounds.
And it’s hard.
If you’re a
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I can’t believe it’s been 2.5 years since we started Angel Squad.
Thank you, TechCrunch, for helping us highlight our amazing community.
From the very beginning, Hustle Fund and I wanted to make angel investing more accessible.
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In my first-ever meeting with a founder, I mentioned that I had an amazing network that he should tap into.
He said, “Awesome, who should I meet?”
I said, “Give me 24 hours and I’ll send you a spreadsheet that lists everyone”
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Here’s a startup secret.
Fundraising is easier for founders who angel invest.
Why?
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I only invest in founders with the next decade in mind.
We will be working together for a very long time, and I want to build the best relationships possible.
Choose the people you’re willing to go the distance with. Any less won’t cut it.
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Small checks lead to bigger checks.
Having an angel to champion your deals is important.
They do the introductions and help promote it to their friends.
This is a flywheel effect most founders miss.
That’s why you want to take checks as small as $1k.
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Angels who write $1k checks care a LOT about that $1k, and as a result, are among the most willing to roll up their sleeves.
Experienced founders who have worked with syndicates know this (and keep coming back).
One thing that has made Silicon Valley successful as a startup ecosystem are all the angels who write $1k checks into startups.
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You think early stage valuations are crazy now?
Just wait until the mass market actually understands QSBS 🤯…
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The harder things get, the fewer investor updates I receive.
Founders, this is backward.
I get it. I would’ve done the same thing.
But the answer is to run (sprint!) towards the pain. It’s telling you something and your company will do better if you listen.
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VC financial jargon is hard to understand.
I’m still learning new terms daily and wanted to make it more accessible.
Here are 8 more VC financial terms that founders and angels should know:
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Two of my closest friends from Lyft came over last night. We’ve been close for almost a decade.
I explained how much I LOVE working at
@HustleFundVC
+ Angel Squad.
They were both like “so you’re legitimately living out your dream!” and I was like “yup!”
Grateful 💛
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Founders spend time and money on something like “nailing our brand identity.”
When in reality, they are avoiding the real work.
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How you ask for intros to angels or VCs can dramatically impact your result.
The rate at which you fill up your round can greatly depend on how much of this network effect you capture.
This is what I would recommend for founders when you ask for intros:
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When a founder responds within minutes, it's confidence inspiring.
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Everyone starts somewhere.
Even Don Valentine.
Here’s how he grew his angel investing hobby into the VC empire is today at Sequoia:
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Founders should all make a habit of sending regular investor updates.
When a founder goes silent, it often signals that they need help.
Investor updates establish an open dialogue with your investors - for both asks and help on certain efforts.
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From all of the startups I’ve seen, the best founders do one thing in common.
They get out the first version fast.
Running a startup is a game of iteration, and the quicker you can improve, the better your odds:
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There’s a perception that founders who sell a fraction of their shares on the secondary market aren’t committed to the long term outcome of their company.
A 🧵 on why I believe that is having a net-negative impact on the ecosystem.
+ an experiment that I link to at the end 👀
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You don’t have that luxury.
The clock is ticking.
You should feel like your back is against the wall.
Founders must put some real points on the board (traction!)
Time is running out.
Stop spending time on fake work.
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You may tell yourself that nailing “brand identity” will help with all of the above.
And you’re right.
Eventually, that’s true.
But that’s not what you need to do in the 0 to 1 phase of building a startup.
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The bar is shockingly low to be a “helpful angel investor.”
Just staying out of the way makes you a top 25th percentile investor.
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Founders - we APPRECIATE you.
You excite us about the future. You inspire us with your work ethic.
Your infectious energy is the best part of angel investing.
Sincerely,
Angel Investors
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Today I celebrated hitting a pretty useless vanity metric -- 2000 LPs have joined the Lyft syndicate on
@AngelList
.
But what use is a vanity metric if not to celebrate it on twitter?
🧵👀
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As angel investors, it’s essential to recognize that some VCs don’t have the same incentives as you.
Most play the AUM (Assets Under Management) game, and you must understand how that impacts their decision-making
Here’s how it works:
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Building a company is hard.
Bootstrapped
Venture-funded
Doesn’t matter
As a founder, it’s important to have a support system.
Your support system might be an investor, an advisor, or a founder community you join.
But don’t go at it alone.
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VC financial terms are confusing.
There are so many to remember for both founders and angel investors.
Here are 10 more terms to add to your knowledge bank:
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As an angel investor, I don’t expect good news from founders whenever I talk to them.
If things are going great, that’s amazing! The good news is always fun.
But honestly, if you don’t share the bad news it almost feels like you’re hiding something. As a former founder, I know
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Angel Squad is my life’s work.
I put everything I’ve got into making it awesome for our members.
While most of the value can be delivered to anyone, anywhere in the world (we have members in 30 diff countries), the in-person events are what really bring the magic out.
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Angels tend to understand that the founder is the customer, not the investor.
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Startups fail, but founders don’t.
I’ve been around startups for nearly a decade now, and I’ve watched many of my friends (me included) fail at one or two startups:
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Founders: "When you are wisely ambitious, you do everything you can to succeed, but you are not attached to the outcome -- so that if you fail, you will be maximally resilient, able to get up, dust yourself off, and get back in the fray." - Dan Harris (10% Happier)
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Founders - take your calendly out of your signature.
If time is your most precious resource, then managing it is a top priority.
Sharing your calendar should be done with intention.
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Founders are desperate for any “shortcuts” that might make their journey just a teeny tiny bit easier.
One intro may unlock that opportunity.
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Has anyone built a
@rabois
chatbot where you can input a tweet about Miami and then it generates a totally uncalled for a-hole response back?
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It definitely feels like AI is getting the exact same "this technology will solve everything" treatment that crypto did.
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To better understand the VC ecosystem, you need to understand Capital Calls.
A capital call is how a fund manager (”general partner” or “GP”) collects money from their investors (“limited partners” or “LPs”) when the fund is ready to invest.
Here's why they're so important:
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If you genuinely believe in someone, make sure that they know that you believe in them.
It’s a small thing, but it goes a long way.
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The 6th of July is always tough for me.
In 2012, I hosted a 4th of July party for a bunch of my college friends. I lived in Hermosa Beach. It was a blast.
But two days later, one of them was gone, which deeply yet subconsciously changed my approach to life.
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Big checks will bankrupt you.
Most of the time.
A bigger startup portfolio is better for an aspiring angel investor:
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🚨NARRATIVE VIOLATION🚨
This is our application volume for
@HustleFundVC
's Angel Squad since inception 👀
Bottom line: Smart people who want to become smarter investors know that now is the time to strike.
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I just realized that I’ve interviewed well over ONE THOUSAND aspiring angel investors for our community (Angel Squad).
That’s over 15000 minutes of customer interviews.
Here's what I learned:
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Most first-time founders overlook this fact.
They are investors in their startups.
They are investing their most valuable resource: their time.
(and also investing their sanity and their partner’s sanity 😂 – shoutout to the founder spouses!)
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200k+ tech workers laid off recently. From Salesforce to Google to Meta.
If 1% of those people decide to start something in the next few months, we'll have 2000+ founders who have a chip on their shoulder working on cool stuff.
Plus, many of them will be pretty well-rested ;)
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Here’s a little startup secret:
Want to get better at fundraising?
Start angel investing.
Why?
- Angel investors build trusted networks of investors, making it much easier when it’s their turn to raise.
- Angel investors get to observe other founders pitch and pick up on the
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It’s no secret: People get into angel investing for the returns.
They want to diversify or become a startup investor.
But there’s typically a surprise along the way 😲:
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As a startup investor, the quality of your partnership with the founder is the most important part of your check.
Some angels write $1k - $5k checks and bring enormous value.
While some angels write $500k - $10M checks that bring negative value.
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Building a strong operator network is an overlooked aspect of angel investing.
Why?
Because 90% of the founder's “Asks” are for introductions.
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Angel investing is not a zero-sum game.
It pays to be a good person.
Word travels fast in this ecosystem:
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I’ve generated $1,000,000+ in fees for
@AngelList
since 2019 from my Syndicates.
And I plan to do it again.
Here’s why I’m getting the better end of this deal:
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I currently have 3 No Code experts diving into all of our systems at Angel Squad and building new applications to make everything run 10x smoother for our Ops team and 10x better for our members.
It's hard to put into words how exciting this is to watch.
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For me, as a former founder, I found that angel investing was a way for me to share my network with founders, and hustle to help them.
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By far the most frustrating part of leading a syndicate is the reliance of LPs to have a Tier 1 lead investing alongside the deal (especially at pre-seed).
That is obviously not how decision making should work, but it is.
Many angel investors will only invest in Pre-seed deals if Tier I Venture Firms are in the round.
Less than 5% of Unicorns were funded by Tier 1 at Pre-Seed.
Founders: You don't need a Tier 1 in pre-seed or investors who expect it.
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I’ve spent the last four years devoted to angel investing.
I've invested in over 100+ companies.
These are the top 3 things I look for as an angel investor and syndicate lead:
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@AngelList
@briannekimmel
End/ If you're thinking about starting a "tech mafia syndicate" let me know. I'd be happy to help, and can also connect you to the other syndicate leads who are equally excited to bring this approach to the startup ecosystem.
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At the beginning of Angel Squad, there was no budget to hire me.
We threw up a landing page, texted our friends, and, in a couple of days, got our first 100 people who applied. That was enough of an initial test for me to bet my career on it and take the plunge.
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Angel investors can look like anyone and come from anywhere:
• Chefs
• Doctors
• Students
• Founders
• Scientists
• Ex-Founders
• Product Managers
• Quantitative Analysts
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There’s a secret to making up to $10M tax-free.
And the best part?
The US government is incentivizing you.
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VC terminology is confusing.
In an effort to make it more accessible.
Here are the 9 VC investment terms all aspiring angel investors should know:
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In my opinion, founders can be the perfect people to become angel investors.
Not only are founders uniquely positioned to spot opportunities and red flags in potential investments.
But learning how to angel invest can also benefit your own company.
Which is why I’m thrilled to
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How do you invest $1K in a startup?
The easiest way to do this is to join a syndicate that offers this option.
Our check sizes in Hustle Fund’s Angel Squad Syndicate make it accessible for smaller investors to take part in the upside.
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At
@HustleFundVC
we're on a mission to educate founders and investors about what we've learned from trial an error as founders and investors ourselves.
We create programs and content to help everyone learn from our mistakes 1/n
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I’ll never get sick of coming home to hug my kiddos.
But I’m really sick of coming home to hug my kiddos and crying, knowing that other parents won’t ever get to do it again.
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Why is angel investing slower to take off in cities outside of Silicon Valley and other major tech hubs?
It comes down to two essential factors that enable the creation of an angel investing scene:
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- Angel investors build trusted networks of investors, making it much easier when it’s their turn to raise.
- Angel investors get to observe other founders pitch and pick up on the things that work well.
- Angel investors get an inside look at effective processes for fundraising.
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VC terminology is complex and confusing.
It’s a very steep learning curve.
Here are the 13 VC terms all aspiring angel investors should know:
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My brother is a hero.
He came in by ambulance short of breath. Already on CPAP by EMS. Still, he was clearly working hard to breathe. He looked sick. Uncomfortable. Scared.
As we got him over to the gurney and his shirt off to switch a a hospital gown, we all noticed the number of Nazi tattoos. 1/
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Founders: chat with at least 2-3 angel investors before chatting with your first VC - especially if those angels are also founders or operators too.
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HUGE Day for
@HustleFundVC
-- I could not be prouder to be part of this team and the special ecosystem we're creating together.
Hats off to
@dunkhippo33
,
@ericbahn
, and
@shiyankoh
for creating something truly differentiated, starting 5 years ago today.
Happy 5th birthday...to ME! (Hustle Fund) On this special day, we are excited to announce our newest fund, Hustle Fund III: a $46M fund to serve great founders at the pre-seed + seed stages. Quick thread (1/4):
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Taking the ferry from Oakland to the Ferry Building in SF is the most pleasant commute on the 🌎
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I wrote my first angel check 4 years ago.
In that time the Lyft syndicate has grown to almost 4,000 members. I currently run the angel investing program Angel Squad at Hustle Fund, which has 1500+.
Here is one thing I tell all aspiring angel investors:
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Decided today that I'll share a crazy story. I have lots...but this one is a fan favorite.
tl;dr - almost was lost at sea in Bali on my honeymoon 🧵
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At
@HustleFundVC
and Angel Squad, we have a culture of respecting each other’s personal boundaries.
Kid is sick? Log off and head to the doctor.
On pickup duty? We get it. We’ve been there.
Logging off early for a special birthday dinner? Tell them we said HBD 🎉
And because
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What Snapchat is for gen-z
@loom
is for grown ups.
I use it constantly.
Gen-z was just 5+ years ahead, per usual.
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I've been investing in startups for a few years now, and one thing I've realized:
Investing has made me a much better operator, and being an operator has made me a better investor! 🔁
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Angel investing has an excruciating feedback loop.
The average startup cycle is 8-12 years long.
Here’s how I get feedback quicker on my investment decisions:
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If you’re in need of an out of the box idea for a 2 year old birthday gift…
You’re welcome.
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As if startups weren't already hard enough.
Hang in there, founders.
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