Hustle Fund

Angel Squad is an angel investing community run by Hustle Fund that was created to teach how to invest in startups and provide access to invest in the most promising ones. TechCrunch referred to Angel Squad as the "YC of Angel Investing."

Angel Squad Co-Founder

Multiple companies

The best place to learn more is @ my personal website: nicholsb.com

I lead an active syndicate with 3.5k members that's deployed $25M+, and have formally Advised 5 companies.

Angel Investor

On Deck

Created, launched, and ran the first two cohorts of the On Deck Angels program. The program pioneered On Deck's expansion into verticals outside of the founder fellowship. 

The success of the program led to On Deck developing the org structure to hire Program Directors to lead verticals that were complementary to the founder fellowship.

Program Director, On Deck Angel Fellowship

- Responsible for procuring sponsorships for On Deck Founder and Angel Fellowships.
- Built and manage program to introduce our founders to investor partners as founders begin fundraising process.

Head Of Partnerships

BlackBird

BlackBird was acquired by Surf Air in February, 2020

- Instrumental in Series A fundraise ($10M from NEA)
- Focused on strategic partnerships / the future of flight (electric aircraft)

Head Of Business Development

- Grew team from 5 to 40+ full-time employees and contractors.
- Recruited and hired leadership from Lyft, Postmates, Uber, Caviar to support the rapid growth of the business.

Head Of Operations

First Round Capital

Angel Track is a masterclass and community for angel investors whose full-time jobs are in leadership roles at tech companies.

1 of 16 selected out of 1k+ applicants.

Angel Track

Zoox Inc.

Zoox was acquired by Amazon in June, 2020.

- Responsible for standing up remote teleoperation unit to support fleet of autonomous vehicles during live operation.
- Represented Zoox’s operations organization when meeting potential investors during our Series B fundraise ($500M, $2.7B valuation).

Operations Manager

Lyft

- Responsible for building out Lyft's local presence in all top 25 Lyft markets.
- Hired local leadership, scaled repeatable playbooks, and provided analytics solutions for Lyft's highest growth markets across the country.

Market Operations Manager (National)

- First Market Manager on the West Coast, drove efficient growth for all of the CA Markets
- Accounted for 50%+ of all Lyft rides

Market Manager, California

RewardTag

RewardTag was bootstrapped and acquired by STM Goods (https://www.stmgoods.com/).

Main partners included Logitech, Seidio, STM Goods which lead to over 2.5M RewardTag units distributed globally.

Co-founder

Over the last decade, I’ve helped build Lyft, Zoox, On Deck, and BlackBird past a combined market cap of over $5B, and helped raise $500M.

In 2019, I decided to try something new.

I decided to shift my focus from building businesses to investing in them.

I teamed up with Ann Miura-Ko to start Uplyft (Lyft alumni syndicate). I was so lucky to have such a great VC guide me when I was brand new to investing. 

It started with 300+ of Lyft’s earliest employees who have invested over $30M+ together.

I soon found myself becoming the go-to "alumni syndicate guy."

I helped Airbnb, Stripe, Pinterest, DoorDash, and many others get their alumni syndicates off the ground.

After opening up the Lyft alumni syndicate to the public (any accredited investor can join, regardless of affiliation with Lyft), I started to notice a trend. There were folks from all over the world, all professional backgrounds, who were investing alongside us.

These folks didn't have access to a network, the knowledge, and the guidance that I was lucky to have.

So, in October 2020, less than a year into the pandemic, I quit my job and joined Hustle Fund – my favorite early-stage VC – to build Angel Squad.

The results were pretty phenomenal.

In 2.5 years, 1,400+ people joined Angel Squad, and as a group, we have invested $21M+ in 50+ startups.

We have reporters, scientists, founders, and students from all over the world in our community. Everyone is welcome.

My portfolio:
-> I run Angel Squad, Hustle Fund's Angel Investing Community
-> I run the Uplyft Syndicate (aka the Lyft Syndicate)
-> I invest in and advise marketplaces and consumer startups

My results:
-> 1,400+ angels are part of the Angel Squad community
-> 4,000+ angels are part of my Uplyft Syndicate
-> $50M+ deployed in startups through Syndicates
-> 100+ startups in my portfolio

ANGEL SQUAD

- Hustle Fund shares their approach to investing 
- LIVE PITCHES from top portfolio companies, and you can invest as little as $1k.
- Meet other members at IRL events as well as get matched 1:1 online.
- Not yet an accredited investor? We pay for your Series 65 exam fee.
- We have a strict no a-hole policy.
- This is a membership offering, with 10 team members who support the program.
- Join 1,400+ others!
- Learn. Invest. Network.

→ GO HERE: www.hustlefund.vc/squad

UPLYFT SYNDICATE

- See 2-3 of my personal deals/month
- There is no community, education, or opportunities to support founders
- It’s free (but nothing like Angel Squad).

→ GO HERE: https://angellist.com/s/team-uplyft/OXf89

Twitter: @b_nicks11
Website: nicholsb.com

Brian Nichols

This is what a $5k angel check turned into.

One investor wrote that first small check. Made 5 valuable introductions that converted into additional checks totaling $170k.  

Those 5 introductions converted into 16 more checks totaling $530k.

So $5k turned into $700k...

People think small checks don't matter. This founder would tell you otherwise.

That angel who wrote $5k became the most valuable investor in the entire round. 

Not because of the money but because they made it their personal mission to get this company funded. 

I've watched this happen so many times now. The $5k check that somehow brings in half your round. The $10k investor who three months later introduces you to your Series A lead. 

The small believer who becomes your loudest champion when things get hard.

Check size and impact aren't the same thing.  

Some of the most helpful portfolio support comes from angels who can only invest small amounts but have networks that would make a GP jealous.

Founders: don't write off the small checks. They're often connected to the big ones. Sometimes they ARE the reason the big ones come in.

Aspiring angels: if you're sitting there thinking your $2k or $5k check is too small to matter, you're wrong. What founders need isn't just capital. It's someone who believes in them enough to spend social capital getting other people to believe too.
--
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Founder of Angel Squad | I write about startups, investing, and hard-earned lessons | Small Bets newsletter

Databricks recently crossed $4 billion in revenue. Growing over 50% year-over-year. Yesterday they made headlines - they are raising at a $130B+ valuation.

Unbelievable company...and it's still private.

Snowflake did $3.6 billion in revenue last year. Growing 29%. You can buy it on the NYSE right now.

So Databricks has more revenue than Snowflake AND is growing almost twice as fast. But retail investors can only access the smaller, slower option.

This drives me crazy. 

The best companies - the ones with the most insane growth - are staying private longer than ever.

Snowflake is a great company. But if you're trying to catch the real rocket ships - the ones that haven't already reached max velocity - you need to be investing in the private markets. 

The gap between what's available in private markets versus public markets just keeps getting wider. And most people don't even realize it's happening.

$5K investment in Uber's seed = $25M at IPO
5,000x return over 9 years

$5K investment in S&P 500 = $13K-$16K after 10 years (depending on timing)
2.6x-3.2x return over 10 years

But obviously there is WAY more risk in early-stage investing...
- Angel investing failure rate: 50-60% 
- Public market failure rate: ~0%  → the S&P 500 has never produced a negative return over any 20-year period.

So if you make 1-2 angel investments you're basically gambling. Roughly 50-50 chance of losing money on each investment.

If you make 20-30+ angel investments you're building a portfolio. Math starts working in your favor. One 1,000x return can cover multiple losses and still generate exceptional returns.

Elizabeth Yin has hammered home the message to me that the key to this game is smart portfolio construction.

Angel investing is about accessing the power law.

In venture capital, about 5-10% of investments generate 60-75% of returns. If you only make 1-2 bets, you'll probably miss those outliers.

But if you make 20-50 small bets ($1K-5K each), your odds of catching at least one rocket ship improve dramatically.

Mina Fung joined Angel Squad almost 2 years ago now.

She jumped right in, got involved, and now, is off to the races starting her own company.

This is a trend we've seen time and time again - start with curiosity about startups (and potentially about startup investing), write a few small checks, and then get the itch and decide to start one yourself.

That's a hidden benefit of joining our community. 

The energy is contagious. 

You start to realize: "hey, I can do that."

Maybe you start a company.

Maybe you Advise (with a capital "A") companies.

Or maybe you just offer to help founders when you can.

In all cases, we feel SUPER lucky to have created the ecosystem that empowers this for almost 2500 members in 40+ countries.

Join us: angelsquad.co

Kanvas

We make new ideas compelling, viable, and investible. We help innovative leaders and founders explore new products, services, functions (e.g. Innovation Labs), or ventures. 

"Kanvas for Start-Ups" -> 

We help founders secure funding, manage burn, and confidently make business decisions. We translate their vision into a compelling, viable, and investible business model.

We offer business model courses to our partner Venture Capital firms, accelerators, and universities to support their portfolio companies. Our capstone content is our six-week "Dreams to Dollars" program.

When we co-invest with our VC partners, we have a proven track record of directly contributing to multi-million dollar raises. 

Example engagements, services, and client references available upon request.

Founder + Partner

HF Scale Partners

Investing @ HF Scale Partners. HF Scale Partners invests in leading growth and late-stage technology companies through direct equity investments and secondary liquidity transactions. Investments include Canva, Anthropic, Epic Games, Eight Sleep, Anduril, ShieldAI, Pipe, Public.com, AngelList, Ellevest, Boom Supersonic, Possible Finance, Webflow, and more.

Principal

The Venture Mentoring Team

The Venture Mentoring Team (VMT) is a nonprofit educational 501(c)(3) dedicated to fostering the startup community by training and certifying mentors, and connecting them with the best and brightest entrepreneurs to help startups reach their full potential.  The organization is composed of 200+ experienced entrepreneurs and executives with corporate, legal, academic, profit and not-for-profit backgrounds who donate their time and talent. The VMT mentors startups to gain traction and sustainability up to their Series A funding.

NYC Chapter President

Certified Mentor for: eMerge Americas (Miami's premier tech conference), Target Forward Founders, Babson College, and more.

Certified Mentor

National Science Foundation (NSF)

One of my best career moments is serving as an Industry Mentor during the U.S. NSF's National iCorps Winter Cohort #3, 2024. Read for more:

About NSF I-Corps:

In NSF’s I-Corps competitive national program, top researchers in science and engineering fields are immersed in a hands-on experience of customer discovery — a key step in the entrepreneurial process that involves talking to potential customers, partners, and other industry stakeholders.

Selected teams are awarded up to $50,000 to conduct 100+ customer discovery interviews during a seven-week course. Through this process, the teams learn how to evaluate the potential for translating their laboratory invention into a successful product and/or service.

About the accepted research:

The Graham Test is a training and concussion assessment system that uses stability and reaction time in sport-specific positioning, with a primary focus on equestrians. As a lifelong equestrian, I'm deeply passionate about the impact this kind of system could have on our sport.

About the role:

NSF I-Corps Teams include a mentor – an experienced entrepreneur who can guide the team as they refine their business models, gain insights from their customer market, and pivot down alternate paths.

Industry Mentor (ICORPS PROGRAM)

Techstars

Mentoring startups on business models and go-to-market strategies. Since 2006, Techstars has worked with startups across a range of verticals, from aerospace to finance, logistics, and retail, connecting them to a network of successful mentors and partners. Each year, Techstars chooses over 500 early-stage companies to join one of their 3-month, mentorship-driven accelerators, investing $120K and providing hands-on mentorship and access to the Techstars network for life.

Affiliated Programs: Techstars New York Comcast

Mentor

Angel investing alongside Hustle Fund, seed to Series A. 
Focusing on systemic issues that keep me up at night (e.g. FemTech, financial literacy, digital health)

Angel Squad Member

Global Women in VC

The world’s largest global community for women in venture capital to connect, collaborate, and create new opportunities. Learn more here: https://www.women-vc.com/

Member

Forbes

Founding member of Forbes’ invite-only, private networking forum for leading women to exchange ideas, innovation, dialogue, and support one another.

ForbesWomen Forum

Day One

I participate in Office Hours and Group Mentoring sessions to help founders fine-tune their business models and pitches. It's a blast.

Day One is building an ecosystem to power the next generation of entrepreneurship. Our Fellowship program is purpose built for early-stage entrepreneurs to tap into a vibrant community, powerful network, and guidance from experienced operators, investors and founders.

Better.com

Learned a lot driving strategy and execution during hyper-growth. Highlights below:

+ Drove strategic planning initiatives across C-Suite to facilitate decision-making (e.g. 2020 strategy roadmap, investor relations, quarterly Board Meeting materials)
+ Orchestrated optimizations across the biz during hyper growth, including scaling onboarding capacity of the underwriting function by 200% (in one month!)
+ Managed weekly executive metric gathering and presentations. Became intimately familiar with things like CAC and LTV, and how their fluctuations provoke insights/action. Took a SQL course, too
+ Organized a new cross-functional Data Governance team to standardize company-wide metrics reporting. Motivated to make my weekly executive metric presentations a little easier (!) and to eliminate KPI confusion I saw popping up in different teams
+ Participated in investor meetings and crafted materials as the business prepared for its Series D raise ($200MN)

... caught the 'startup bug' while I was here. Passion projects evolved accordingly. Left to pursue them, and been an entrepreneur ever since.

Strategy & Business Operations

Founder & Partner @ Kanvas | Foster Innovation, Develop Business Strategy, Drive Growth

Katie Nowak

Honored to host a breakout at the All Raise VC Summit tomorrow on a topic we’re all navigating: what do you do when IPOs stall?

At "Choose Your Exit: Liquidity When IPOs Stall," we will be in dialogue on all things re: liquidity in venture!

Topics may include:

✨ how expectations around liquidity is shifting generally,
✨ secondaries-as-a-strategy (for investors and their founders),
✨ stories of founders and investors navigating off-cycle exits, and
✨ how to keep stakeholders (LPs, GPs, founders) aligned through it all.

We can't wait to share best practices and learn from each other.

If you’re at All Raise, we hope to see you there! 

Looking forward to co-hosting this important topic with Seyonne from Stepstone. 

I will be channeling our fearless leader at Altra, Jamie! 💫  

-

I'm Katie Nowak, an investor, innovation leader, and new venture designer sharing examples & lessons weekly.

Follow me + hit 🔔 to stay tuned!

Innovation Leader, New Venture Designer, Speaker @ Kanvas || Investor @ Altra Venture Partners

If you're in the Bay Area,
here's a holiday event you don't want to miss! 🤯 

I'm delighted to be a Founding Member at Aureum Leaders Circle, a community of founders, investors, and executives here in the Bay Area.

At our first annual holiday party, we will be reconnecting with old friends and building new relationships that will last a lifetime. :)

Here are a lot of communities out there, but I have been blown away by the quality of what Mohammad has created - he has an incredible gift of identifying smart, genuine humans...

...and keeping them engaged! The Aureum Leader Circle is officially my most active group chat.

Just one month into ALC, and I've:

✨ met rockstar founders (like Anatoly)
✨ made intro's to investors in my network
✨ received comp'd tickets to national conferences 
✨ attended events I never would have found otherwise
✨ brainstormed new investor events with ecosystem partners
✨ forged new ideas of how we can support the venture landscape

…and so much more.

So join us!!

December 4th, Fairmont San Francisco.
Seats are limited, don’t miss yours → https://luma.com/z2fuqofy
Comment "Founder Fuel" for an exclusive discount.

___

I'm Katie Nowak, an innovation leader, new venture designer and investor sharing stories & lessons weekly.

Follow me + hit 🔔 to stay tuned.

Join me @ Founder Fuel - Dec 4th, SF Fairmont Hotel

Here's a secret to selling faster,
no matter what industry you're in - 🤯 

Build trust, systemically.

Recently, I connected with a founder who said buyers pick his B2B solution because they trust him.

...but he noted that building trust takes time (sometimes months) and that slows sales cycles. Especially in new markets.

Plus, there are only so many 1:1 lunches you can do!!

So, we brainstormed how he could accelerate trust at scale.

Here are some examples we came up with:
✨ co-deliver with respected implementation partners
✨ build his leadership teams' personal brands (hi LinkedIn)
✨ publish thought leadership with real market insights/wins
✨ speak at industry panels or on podcasts customers follow
✨ host relevant discussions/roundtables within the industry
✨ bundle with complementary products already in customers’ tech stack
+ many more.

In all sectors, trust is the root driver of most deals and referrals.

When you find ways to build it at scale, your sales cycles shrink, and your credibility compounds.

Social proof is a ~ mystical, magical ~ thing!!
(Humming Benson Boone's song while I type that 😂)

-

How does trust factor into your growth strategy?

Which of these strategies are you going to try...

...and what else should we add to the list?!

Tell us below in the comments 👇 

—

I'm Katie Nowak, an investor, innovation leader, and new venture designer sharing examples & lessons weekly. Follow me + hit 🔔 to stay tuned.

2025 is the year of AI dominance in venture capital. 🤯 
These market insights make it official - 

According to CBI Insights Q3 2025 Venture Market Report:

✨ For the first time, AI startups command 50%+ of VC funding
✨ The U.S. market represents 85% of AI dollars invested, globally
✨ Mega-rounds are taking the lion's share (yes we see you Anthropic, OpenAI), so while dollars are up, deal count is down.

Venture aims to back the next wave of innovation - and this year, the data tell us it's a full-throttle bet with AI at the core.

...anyone surprised?!

Jokes aside, here’s what I’m thinking about:
+ How might these investments reshape how we live, work, and play?
+ What lessons will we look back on, five years from now?
+ How do we plant seeds for what comes next? :)

Would love to hear your reflections and ideas. Drop them in the comments!

(P.S. I’ll tag CBI’s full Q3 report below if you want to nerd out, too 🤓)

—

I'm Katie Nowak, an investor, innovation leader, and new venture designer sharing examples & lessons weekly. Follow me + hit 🔔 to stay tuned.

Thrilled to join the investor panel for Desafía SF’s 1:1 Office Hours on Nov 17!
Here's why -

Ten high-growth startups are flying in from around the world with big ambitions to scale in the US. The teams are building across hot industries like Fintech, CleanTech, HealthTech, and AI.

Their impressive innovations include:
✨  Zero-emission delivery fleets
✨ VR medical training & digital neuro-rehab for patients
✨ Grid optimization already used by 30+ utilities
✨ AI copilots for wealth management, dev automation & video intelligence
✨ A platform to launch institutional-grade funds in days

They’ve collectively raised $20M+, backed by global VCs, corporate partners, and real customers. 🤯 

Can't wait to meet the teams, understand their solutions, and help shape plans re: what it will take to grow in the US market.

Big thanks to Founder Institute and the wonderful Serephina Ha for bringing together this amazing lineup! I'm thrilled to be a part of it. 

-

I'm Katie Nowak, an investor, innovation leader, and new venture designer sharing examples & lessons weekly.

Follow me + hit 🔔 to stay tuned!

Desafía SF 1:1 Office Hour with Investors

Here’s the growth strategy hiding in plain sight, 
no matter what your company does - 🤯 

Your personal brand!! 

Here are three key takeaways from talking brand (and seeing it work):

✨ Your brand works harder than any pitch deck.

People do business with people, not logos. 

(Say it louder for the people in the back!)

A well-tended brand bridges cold intros, opens unexpected doors, and quietly shapes the narrative even when you’re not in the room.

Quick ideas to build brand:
+ Speaking on podcasts/panels
+ Sharing good vibes at industry events
+ "Giving" first when building relationships
+ Writing thought leadership content (LinkedIn!!!)

✨ Authenticity isn’t a buzzword... it’s your moat.

Trying to sound like everyone else? 
Using ChatGPT to write your LinkedIn?

We notice! And its unfortunately forgettable. 

Show up as you are. The quirkier the better IMO, as my followers know by now 🤣

Over time, consistency and honesty make you memorable (and magnetic) in a sea of sameness.​

✨ Treat your brand like a product your company offers.

...because it is!

Experiment, measure, and iterate your brand, just like you would any new offering.

For example - writing content online? 
+ Test messages and platforms.
+ Ask peers/colleagues for feedback.
+ Measure engagement metrics.
+ Double down on what connects.
+ Sunset/reword what doesn't land.
+ Offer real value to your audience along the way!

-

Over the last several years, I've invested in my brand and ended up creating my own business model design course, an ever-expanding business, and my dream role in venture. 

It's been the single best career move that I've made.

If I can build my brand, so can you!

-

So tell us - what’s one move you’re making (or resisting) on brand right now?

And if you posted on LinkedIn today, link it so we can support you!

See you in the comments 👇 

—

I'm Katie Nowak, an investor, innovation leader, and new venture designer sharing examples & lessons weekly. Follow me + hit 🔔 to stay tuned.

Today, Dyson is a multi-billion dollar household name.
...but it took 5,127 prototypes to get there. 🤯 

Here's what I love about the Dyson story:

✨ Patience brought the hardware moat to life.

A lot of people would have quit after 100 prototypes. 
Dyson made it to 5,126.
(The 5,127th worked!)

Ask yourself: 
+ What is your relationship with patience, today?
+ What areas of your business could use a learning mindset (focused on experiments, not fearful of failure)? 
+ How could you nurture that mindset over time?

✨ Boring problems can have exciting solutions. 

A vacuum sounds boring. 
...but solving it better changed an industry.

Ask yourself: 
+ What boring problems is your industry overlooking, today? 
+ What is the resulting opportunity, near-term?
+ Where could it grow, long-term? (Thank you, Dyson Airwrap!)
+ How are you uniquely positioned to solve it?

✨ Constraints force creativity.

Dyson had no funding. No manufacturer backing (because they wanted to keep selling vacuum bags ugh). No shortcuts.

...and look what he created!

Cheers to his wife for supporting him in the early days. 🥂 

Ask yourself: 
+ How could our perceived financial limitations actually be an advantage?
+ How might we generate revenue along the way to my North Star vision?

---

It's been awhile since I've highlighted another entrepreneur's story!

What inspired you from Dyson? And who would you want to hear about next?

Tell me in the comments :)

—
I'm Katie Nowak, an investor, innovation leader, and new venture designer sharing examples & lessons weekly. Follow me + hit 🔔 to stay tuned.

taplio

The Battle

Brian Nichols

Katie Nowak

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