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.
--
👉 For more content like this, join 55k+ startup enthusiasts by subscribing to Small Bets: https://lnkd.in/gPeXk6Eb

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

Wiley

Author of Amazon’s #1 New Release: “Your AI Roadmap"

Bestselling Author: Your AI Roadmap, Featured in Forbes

Clarity AI

Our Mission: To empower business leaders to craft AI roadmaps to future-proof their business
Learn more: HireClarity.ai

🎯 Your AI Roadmap Talk and Workshops Include:
🔷 Align AI Initiatives with Company Goals
🔷 Ensure Compliance and Data Privacy
🔷 Prioritize AI Literacy and Internal Trainings
🔷 Identify High-Impact AI Opportunities
🔷 Foster a Growth Mindset: Iterate and Improve

Clarity AI equips leaders with a proven, structured approach to AI roadmap creation. We align business goals with executive leaders with data and AI strategy. AI has hype, but how do leaders operationalize how to integrate new solutions into the business? We remove roadblocks and build clarity and alignment.

🧠 Are you interested in future-proofing your business? Struggling with AI strategy?
🎯Join Clarity AI to craft 10 Step Your AI Roadmap via Gartner operationalized framework
Boost revenue, increase efficiency, and future-proof your business

📨 DM me or visit HireClarity.ai to learn more

Chief Executive Officer

Perplexity

Business Fellow

Pluralsight

AI and Data Educational Courses and Code Lab: ChatGPT Enterprise: Advanced Data Analysis, Create Dynamic Data Visualizations in R, Advanced Data Visualization Techniques in R, ChatGPT Pro: OpenAI o1, Introduction to Statistical Analysis for Data Analysts, Generative AI for Colleagues

Technical Course and Code Lab Author: AI, Data, Code, Stats

3 Ridge Technologies

Strategic Advisor, Agriculture Innovation, GTM, ROI, AI Product and Data Strategy

Female Invest

Member

Women in Voice

Founded 501c3 nonprofit. Raised over $500k+. Partnerships with Amazon and Google. 65k+ Socials

Founder of Nonprofit, President Aug 2018-Aug 2024

Professional Speaker

CES, VentureBeat, VOICE Summit, AI Summit, GeekGirlCon, Women Who Code, WIT Regatta
Learn more: JoanPBajorek.com

Keynote Speaker | AI Expert

OneReach.ai 

OneReach.ai is a a B2B SaaS Platform in Generative & Conversational AI

Role: Served Customer and Internal R&D Projects for Data-Driven Optimizations Translating into Multi-Million Dollar Opportunities for Fortune 500 Companies
Cross-functional work on Data, Data strategy, Product Feature Roadmapping, Analytics, Case Studies, Reporting, Customer Success, Partnerships, Pre-Sales Enablement, and Evangelism

Data Science and Analytics Work
Analyzed Customer 400k+ Data Sets for Data-Driven Product Optimization Opportunities
Worked with Omnichannel, SMS, IVR, Multimodal Bots and Visualizations
Identified Upsell Opportunities, Increased Readability of Dashboard and Customer Reporting Tools Conducted Competitive Analyses of Partner Technology and System Integrations
Communicated and Unskilled Team with Collaborative and Responsible AI and Data-driven Mindset
Reviewed Data Pipeline and Practices and Made Data and Analytics Recommendation, 
Created Innovative, Descriptive and Predictive Analytics, Leveraged ChatGPT/AI for Code, Data Visualizations (Javascript and D3), and Descriptive Statistics
Wrote Case Studies Documenting $35M Use Cases, $3M Unrealized Revenue Potential
Leveraged Prompt Engineering to Generate Shiny App Prototypes

Storytelling & Evangelism
Speaking Engagements at Major Global AI and Networking Tech Conferences
Generative AI Webinar 2023: Co-Founder, CEO and Joan, 300+ registrants: https://www.linkedin.com/events/taminggenerativeaiwithonereach-7021526024400097280/
Conversational Collective 2023: Co-Founder, COO and Joan: https://www.youtube.com/watch?v=euRv4FM9o_w&t=2275s
Translated Technical Information and Projects to Senior and General Audience
Created Lead-Gen Opportunities with 300+ Registrations for Low CAC
Crafted Strategy, Grew Impressions 507% and Clicks 485% on Most Important Conversion Channel

Worked on Healthcare, Telecom & CPG Verticals

VP of Data and Analytics

Seattle Angel Conference

Reviewed 80+ startups in conjunction with other investors
Narrowed down startups to finalists to conduct due diligence

Investor

CEO Clarity AI 🔥 AI Influencer 👉 Built 80k+ Followers | 🎉 AI, Data, & Product Builder | Your AI Roadmap Podcast Host | x-VP, x-Nuance CES, VentureBeat | Women in Voice Founder | Investor | Linguist ☕️ 🐶 🏃🏽‍♀️

🏆 #4 Voice AI Influencer
🏆 Speaker at CES, VentureBeat, FOX4
🏆 Bestselling Author “Your AI Roadmap”
🏆 Featured in Forbes, HBR, Adobe XD
🏆 Perplexity AI Business Fellow
🏆 VP of Data and Analytics 🔀 Founder

Dr. Joan Palmiter Bajorek is an AI Expert, Keynote Speaker, and Bestselling Author ranked the #4 Influencer in Voice AI by Voicebot.ai. As an AI builder, Dr. Bajorek has 10+ years of technical experience in data and AI development for Fortune 500 clients, she has held senior roles at Nuance (acquired by Microsoft for $16B), Netavox, VERSA Agency, and as VP of Data and Analytics at OneReach.ai.

A highly sought-after speaker, Dr. Bajorek has spoken at CES, KATU-ABC, FOX4, VentureBeat, and Voice Summit. Her work is featured in Forbes, Harvard Business Review, Fox Business, Adobe XD, and UXmatters, and at Google i/O.

Recently featured in Forbes, her Amazon bestselling book, "Your AI Roadmap: Expand Your Career, Money, and Joy," was published by Wiley in Jan 2025. The book is a companion to her international podcast, Your AI Roadmap, featuring top AI builders from Google, Amazon, Microsoft, Upwork, Adobe, Intuit, and more.

With academic credentials including a PhD in Conversational AI from the University of Arizona and an MA in Linguistics from UC Davis, Dr. Bajorek combines cutting-edge technical knowledge with exceptional business acumen to deliver high impact and data-driven results.

Based in Seattle, WA, she is available for speaking and workshop engagements, consulting partnerships, and media appearances

DM and email joan.bajorek@hireclarity.ai

Dr. Joan Palmiter Bajorek

REVENUE GROWTH 611% in 2025 📈 EXACTLY how it happened 🎯
Getting close to fiscal end of year goals. I'm in a reflective headspace...

In a world that feels heavy— Layoffs ⚠️ Burnout 🥵 Uncertainty ❓

I just want to pause and say:
✨✨✨✨✨✨✨✨✨✨✨✨✨✨
I'm grateful. Deeply 🙏
✨✨✨✨✨✨✨✨✨✨✨✨✨✨

To the customers who see the work 👀
To the customer who said "for this value, I'd pay $10k-$15k more"
To the customers who give rave testimonials publicly 🤝
To the presales customer who ask ME for the followup call 💸

Here's what took my business to new heights compared to last year:

1. Author: In 2024, I spent 3-4 months writing the Your AI Roadmap book 📚✍️ (yes, worth it but MONTHS away from selling)

2. Business Coach: I hired a coach who for a whole month costs LESS than one therapy session 🎓💡 Her work has been invaluable in mindset, frameworks, and centering my health

3. Say No, so I could say HECK YES: Stepping back from a potential 9 figure potential project with LONG sales cycles and high risk while bestselling products close in 20-30 days

4. Clarity: I cleared my plate to focus on what customers LOVE 🎯❤️: AI workshops where customers see results and AH HAH moments galore

5. Testimonials: I have a WALL of testimonials 🗣️⭐

6. Simplify: I streamlined sales cycles ⚙️✨ less complexity, more clarity

7. Sales Work: Invested in my sales acumen—upsell, downsell, retargeting, standard opening questions 💼🚀 Less building, MORE selling

8. Listen: I listened DEEPLY to customer needs. THEN built workshops 👂💬

9. Referral Partners: I found quality partners for work outside my zone of genius 🤝💰 Win-win-WIN deals

10. No/Low Meeting Mondays and Fridays. Got to have time to actually do customer heads-down work!❤️🧠

One of my biggest "AH HAH" moments? 🧠🧠🧠

Coming back from vacation and seeing my business in a new light.

I was SHOCKED workshops were my bestseller 🤯
Where customers put down the money. Data don't lie 💯

3 AI Tools for 5x Productivity is our bestselling workshop of 2025
Folks LOVE it. Rave about it. Employees say "fun"
CEO says "Why didn't I know about this tool!!!"
My firm AI helps executives upskill in AI to future-proof businesses 🤝

It might look lucky 🍀
This is really about consistency  📅
This is really about learning from data 📊
This is really about being open to being wrong

It's about courage to take the business seriously
To make hard decisions and have tough convos ❤️

Not gonna lie, there were tears and nights of poor sleep
But the in weeks of tripling down 

The next months of consistent sales
Then tripling down again for our upcoming sprints..... let's go 2026!

Entrepreneurship is not for the faint of heart 🚀
If you're tired, rest… then keep going 🛌➡️🏃‍♀️
If you're wondering if it's possible
It is. 💥
Cheering you on towards your goals!


What's are you doing to scale? Share it!  👇

Photo: me holding the best focaccia of my life in Rome
See all the rosemary and salt crystals?!?!?
Joan bringing home the bread!

Woman with long brown hair wearing a teal cardigan and colorful striped shirt smiles while holding a metal pan containing golden focaccia bread in an outdoor restaurant setting

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