👋 Friends,
I just returned from Arizona, where I watched Nicole run 100 km over 15.5 hours. I struggle with running 10 km, so 100 km is unimaginable. What an absurd feat of athleticism and determination. Also, our annual Outliers Summit is THIS week! We’re excited to host 2,000+ of you. I genuinely hope this event has a big impact on your career and life.
📅 Upcoming Events
Nov 4 | ⭐ Outliers Summit VIP Day (NYC) – Meet and learn from the founders of Polsia ($8M ARR with 1 employee), OnDeck, PuppySphere ($14M revenue, bootstrapped), and the Media Mafia (20-year-old CEOs generating 7-8 figures)
Nov 5–6 | 🗽 The Outliers Summit (NYC) – A two-day gathering in New York for founders, builders, and creators bringing unreasonably ambitious ideas to life. Only 10 tickets left!
Nov 6 | 🎉 Outliers Summit Closing Party (NYC) – Hosted at Unveiled, one of the hottest nightclubs in Williamsburg.
Nov 9 | 🍽️ Junto Founder Dinner (NYC) – Apply to attend. Join a handpicked group of early-stage venture-backed NYC CEOs and founders for dinner on us.
Nov 10 | 🗽 The Shortlist: November Founder Showcase x Oak HC/FT (NYC) – Meet the founders/CEOs of the fastest-growing tech companies in the city. A special edition with Oak HC/FT.
Nov 19 | 🍽️ Future of Storytelling Salon (NYC) – Join a dozen brand leaders, marketing execs, and creators for a discussion on the future of storytelling.
Dec 9 | 🍽️ Junto Founder Dinner (NYC) – Apply to attend. Join a handpicked group of early-stage venture-backed NYC CEOs and founders for dinner on us.
• • •
I recently had dinner with a successful exec in his 50s. He moved up quickly in his career, became a manager at a young age, reached the C-suite, and made life-changing money through several company exits.
But one thing in particular stood out to me.
Unlike many other execs I'd met, he seemed truly happy and fulfilled, a contrast to the others who had scar tissue from decades in corporate that left them seeming worn out.
So I asked him what his secret was.
He told me he’d followed one rule for almost 30 years:
Work for someone who is both (1) highly competent and (2) high-integrity.
It made me reflect back on my time in corporate.
In the last fifteen years, I’ve worked for 10 bosses at six companies. 1 was horrible, 7 were ok, 2 were good.
A good boss is rare. So how do you find one?
Well, the bad ones are obvious. They gaslight you, give you the menial work, take all the credit, treat you like crap… like a toxic ex. But it is extremely difficult to distinguish the good from the great.
And if you’re wondering whether a good boss matters at all, let me tell you now:
Your boss is the single biggest variable in whether you love or hate your job. They’re either your source of energy or your source of misery – a great boss is the difference between waking up ready to take on the day and not wanting to get out of bed.
A few signs you’re working for a great boss that I’ve collected over the years:
They teach you something. Early in your career, you learn the basics: how to write good emails, run meetings, and deal with clients. Later, you’ll learn judgment, leadership, hiring, and management, but for the relationship to remain valuable, they need to keep growing too.
They give you visibility and credit. A great boss puts your name on your wins instead of their own, and makes sure the right people know it was you. If they keep you behind a screen, that’s a red flag.
They value you. They preemptively offer you paths to more money, more growth, and a bigger role, and they’ll fight to get you there.
They play to your strengths. A good leader recognizes that you’re naturally better at some things and steers you toward them, instead of forcing you into a mold. Strong managers build roles around people, not people around roles.
They give helpful feedback. They are genuinely motivated to help you become the best version of yourself. And btw, no feedback doesn’t mean you’re doing well; it means your boss isn’t trying.
They constantly challenge you. They can see when you’re deep in your comfort zone and push you to do more.
They are a strong communicator. They speak well, write well, or can do both. Most of leadership is communication, and if they can’t articulate their point, they can’t be effective.
They protect you from unnecessary politics. At Facebook, we called this “air cover.” A good boss will protect you from drama, politics, and bureaucracy, to let you do your best work
They give you autonomy and trust you.
They create psychological safety. You can disagree with them, admit mistakes, ask dumb questions, deliver bad news, and talk openly about your salary and your aspirations. They also make time for you. It’s hard to put an exact number on it, but my rule of thumb is at least 30 minutes a week on work, and an hour a month on your career.
The two great managers I had had all 10 things on this list. The ok managers: 5/10; the bad ones: less than 3.
If you find someone who fulfills all 10, keep them around.
A few notes:
It’s rare for someone young to be an exceptional boss. It takes EQ, empathy, and lived experience that come with time. Exception to the rule: former founders.
Young, early-stage companies don’t always have strong managers, and that’s ok. They’re flatter, mission-focused, and moving too fast to build good management structures early on. You’ll still learn a lot.
None of these are fixed traits. You should feel empowered to share feedback with your boss (yes, you’re allowed to), and you can often change a few of these things yourself.
• • •
📌 Things I’m Reading
Things that recently made me laugh, made me think, or left me amazed.
Who actually gets rich if Anthropic lists at $2 trillion? (post) – A financial breakdown of how much equity employees at Anthropic have. Hint: it’s more than you think and exposes how much startup employees can make if in the right place at the right time.
No Experience Necessary (book) – I met Ronnen (founder of Spinmaster) recently. He has a bizarre story. At 23, less than a year out of college and living at home with his mom, he started a company with his friends and $10K, selling children's toys. Today his co does around $2B a year.
What it’s like to make 45K in NYC (article) – I made $45K/year at my first job out of school while living in a HCOL (high cost of living) city and saved $200/month. I was lucky to break through and switch careers, and this was a good reminder of how much luck was involved.
The Final Lap, or What It's Like to Be 89 (article) – There’s plenty of “hustleporn” about grinding in your 20s from people who are just getting started, but what is it like to be at the end of your life? I’ve often heard that after 30, you feel 25 forever. This guy is still skateboarding in his 80s, so it must be true.
• • •
💃 Tech Community Plugs
Resources for entrepreneurs, investors, and tech professionals.
✍️ Your AI Head of Content. I’ve been using Stanley for months, and it’s the only reason I could run two companies and still grow 100K+ followers this year. It texts me what to post, tells me what’s working, and auto-schedules everything from my iMessage. Free to try for 30 days with code ANDREW here.
💼 Hiring top GTM & engineering talent in NYC? Apply to pitch at our monthly Shortlist founder showcase and meet the top 1% operators from my network.
🍽️ InKind – the ultimate dining app for foodies … earn up to 30% back when you eat out, plus get $50 off your bill every month at select spots. And as a bonus, we both get $25 free when you sign up. Sign up here.
🏢 Looking for an office space in NYC? I know of a few great spots opening up. Hit reply if you’re searching.
🚀 Forum Ventures is closing out their Winter cohort. If you have been thinking about applying, this is the last call. A few spots left for B2B founders who want a real partner, not just a check. Apply here.
🧮 Need a CPA? I’ll introduce you to Alex, who I’ve worked with for the past three years. He’s excellent and specializes in tax support for high-earning individuals and entrepreneurs. More info here.
🏦 Fidelity Private Shares is the best-in-class equity management platform with 409A valuations and a secure data room. With Fidelity Private Shares, you’re always fundraise-ready. To learn more, reach out to Charlie Stephens at Fidelity for support! Learn more.
🇺🇸 Looking for help with US immigration? Reply here – I’ll connect you with the attorneys and team I trust for visas, green cards, and all the corporate immigration matters.
💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.
📈 Investors – Looking for deal flow? Receive curated deal flow from my network in your inbox every month. Sign up here.
What other perks should I include? Let me know.
• • •
(Sponsored) 🤖 Hyphenate just raised $45M in Series A funding.
AI agents are starting to do real work inside companies, and finance might be one of the biggest opportunities.
Hyphenate is building an autonomous finance platform that uses AI agents to handle workflows across revenue, treasury, and accounting. Think less time spent on spreadsheets and manual processes, and more time for finance teams to focus on strategy. A pretty exciting glimpse into what the future of the CFO's office could look like. Read the announcement here.
• • •
🖼️ Behind the Scenes
I’ve always wanted to build my own board game. Preferably something tech-related (I’m a nerd).
So as a side quest, I talked to a dozen people about design, sourcing, manufacturing, packaging, and licensing. They told me it would take a year and cost $100,000.
Then I met the team at Accio, and we built a custom board game from scratch in ONE month. Basically:
Designed the full concept, board, and rules, with the tech theme baked into every tile and card
Generated all the artwork and visual design, no separate illustrator or studio
Sourced the manufacturing and materials, from the board to the pieces to the packaging
Handled the production logistics the experts said would take months
Went from idea to a real, physical, playable game in about 30 days.
A year and $100,000, compressed into a month. Pretty incredible.
P.S. Here’s a video we made of the whole thing