Read This if You’re Young and Ambitious
Lessons I wish I knew at 18, our next founder showcase & our SXSW preview.
👋 Hey, it’s Andrew.
Sorry for the hiatus. I took a short break from writing – I’ve been busy launching our new business, The Shortlist, planning for SXSW (see below), and sharing my unfiltered takes on TechTok, like this one: “Do this to be rich in your 20s.”
Today's piece was inspired by a recent conversation with a new grad who asked me, "How should I think about my career?"
📅 Upcoming Events
Feb 17 | 🍽️ Junto Founder Dinner (NYC)
Feb 23 | 🎙️The Shortlist: Feb Founder Showcase (NYC) – an application-only evening connecting six breakout CEOs with exceptional engineers, designers, and business leaders.
Feb 26 | ☕ Founder Breakfast Club (NYC)
Mar 12 | 🥂 “off menu” – a ceo dinner at a private mansion (Austin) – hosted at a private mansion 5 minutes away from downtown Austin. If you run a seed to series B company, you’re invited. We only have 12 spots!
Mar 13 | 🥂 “off menu” – a ceo dinner at a private mansion (Austin)
Mar 14 | 🤫 secret austin garden party (Austin) – our iconic secret party that we throw every year. Thousands of people come from all over the world.
Mar 15 | 🥂 “off menu” – a ceo dinner at a private mansion (Austin)
Mar 24 | 🍽️ Junto Founder Dinner (NYC)
April 6–9 | 🌉 HumanX (SF) – join me at HumanX, the most important AI conference of the year in SF. Use HX26P_FIBE for a discount!
What I would’ve told myself at 18
When I started my career, so many things held me back and kept me running in a hamster wheel. Some were small and silly. Others were existential and took me years to figure out.
But if I could go back in time, these are all the things I would’ve told myself at 18:
Stop asking “Is it true?” Start asking “Is it useful?”
A limiting belief is a story you tell yourself that holds you back - and you accept it as truth.
I’m not smart enough.
I’ll never be successful.
I don’t have enough experience.
I’m not the type of person who accomplishes big things.
I have them. Your role models have them. We all have them. They exist to protect you, but they’re not helpful. The key is not to ignore them but to say “Yes… and.” Yes, this might be true, and I’ll do it anyway. Then do the thing, prove yourself wrong, and those limiting beliefs won’t feel true anymore. Competence breeds confidence. Do it enough, and the little voice goes away, and your perception of the ‘truth’ will completely change.
Do you want to sound smart or be rich?
I had a college roommate who seemed to know everything. He was smart, well-read, but also deeply skeptical and judgmental. Every time I shared a new idea with him, he would shoot it down.
“This will never work because of X.”
And yes, he might’ve been right, and that made him sound smart.
But with that state of mind, he never took a swing at anything. Never took a risk. Because if you’re conventionally smart, you’ll always make the rational decision. Risk vs. reward. But chasing your dreams and pursuing the path with asymmetric upside is never rational. They’re emotional decisions that come from the heart.
If you want to be rich in the long run, you’ll have to forgo looking smart in the short run.
Never make decisions from a position of fear
Every bad decision I’ve ever made has been from a position of zero leverage.
My advice: If you recognize that you’re fearful, don’t make big decisions until you’re grounded.
Examples:
Picking a business partner because you don’t believe in your ability to do it alone.
Pricing yourself lower because you don’t believe you’re worth more.
Not asking for a higher salary because you don’t think you can get another job.
Choosing to be in a relationship because you don’t believe anyone else can love you (deep, I know).
Like sharks circling blood, people will smell your fear and take advantage. Recruiters, CEOs, investors, and dating partners.
Instead, make decisions from a position of power. How? Create abundance for yourself. Build yourself up to the point that nobody (not even you) can deny the value you bring. Be so good they can’t ignore you.
Don’t surround yourself with people with small ambitions
If you want to be extraordinary, you need to be around extraordinary people. The people around you set the standard for what’s possible.
When I lived in a smaller city, it was unheard of to start your own business. It was even more unheard of to scale your own business to millions in revenue. And it wasn’t until I moved to New York that I realized building a million-dollar business was the baseline for what some people achieve as hyper-ambitious. If what I said sounds absurd, then you should move to New York or San Francisco to experience it.
But I don’t mean to suggest you should ditch your day ones and leave home because your kindergarten buddy doesn’t aspire to be a billionaire. I mean to apply this to your professional network – the people you spend your working hours with.
Spend 20% of your time working toward the future
The most critical piece of advice I received when starting my business was to spend time working on the business, not just in it. This applies to careers, too.
Occasionally, lift your head up and allocate 20% of your time to thinking about the future. Some call this ‘personal R&D.’ Spend a day a week trying new things with no immediate return. That might be:
Tinkering with AI
Learning a new skill
Speaking on a stage
Expanding your network with people outside your existing community
Google once coined the 20% rule: Employees are to spend 20% of their time working on innovative, self-directed projects. The intended impact was for employees to be more creative, innovative, and to think about the future. The result led to the invention of Gmail and Google Ads.
Change your environment to increase value
We’re all familiar with the adage: A bottle of water costs $2 in the city but is priceless in the desert. Sometimes all you need to do is change your environment to increase your relative value.
I know people who are too ambitious for their own good to succeed at large corporations. They are seen as unpredictable, volatile, and difficult to manage. But this is the exact type of person to thrive in a startup environment. They’re described as: high-agency, proactive, hustler – night and day, from their relative reputation at a corporation.
It’s far easier to change your environment than to change yourself. It took me years working at large corporations to realize I was in an environment that limited my potential.
Soft skills are the new hard skills
If I had to give blanket advice to all young, ambitious people across all career paths, it would be this: work on your communication skills – your speaking, writing, and capacity to build relationships with others.
Working on these skills will give you the best bang for your buck in your career. And I believe this will be even more valuable as future generations spend more time behind screens.
Excellence comes in different forms
Form an image of a great salesperson in your head. What are they like? My guess is a charismatic, social person with slicked-back hair, a firm handshake, and well-dressed with a smile on their face. This is a common image. Strangely enough, the best salesperson I know is quiet, empathetic, an amazing listener, careful with words, doesn’t talk too much, but when she does, she sounds incredibly elegant.
Excellence can take many forms. Just because you don’t fit the traditional mold doesn’t mean you can’t be great. In fact, the greats break all stereotypes and create a category of their own.
Play the internet lottery
Third doors exist as shortcuts that give people a shot if they’re willing to risk looking silly and do something unconventional.
Playing the internet lottery is one of them. Social media has only been around for the last two decades and, as a viable income stream, for the last decade. Yet, so many career paths and tens of billions of dollars of economic value have been created by this new internet economy.
If you post on LinkedIn, YouTube, or TikTok weekly, that’s 52 chances a year to go viral, get clients, make money, get your dream job, or meet someone who might change your life. Yet the number one obstacle stopping most people from posting is the fear of looking cringe. Mr Beast posted 100–200 videos before anybody noticed him.
Everything is cringe until it works.
(This thesis is largely why I’ve been so active on TikTok)
Delusional optimism beats rational pessimism
In college, we learned about the efficient markets hypothesis.
The technical definition: Financial markets fully reflect all available information in asset prices, making it impossible to outperform the market using known information.
My interpretation: Everything in the world that can be done is done. There are no opportunities to create value because the markets are perfectly efficient.
For years, I avoided doing anything entrepreneurial because I believed everything in the world was already optimized to perfection, but this was a counterproductive and low-agency way of thinking. It wasn’t until I dispelled this belief that I started building and tinkering. I’m not a finance expert, so I don’t know if it’s actually true. But I do believe in delusional optimism when going after opportunities.
Finally, your problems will never disappear; you just get better problems
I have the same number of problems today running multiple companies (including a 7-figure company) as I did 10 years ago when I was making $45,000/year at a large company.
But my problems today are much more fulfilling to solve.
I used to think that with more success, your problems would disappear. That’s not true. You just get a different set of problems. Your level of stress will always expand. Translation: You will always be stressed about one thing or another.
The goal is not to eliminate your problems, but to find better ones.
🤠 Are you going to Austin for SXSW?
We’re back at South by Southwest from March 12–15 for our fourth year in a row. Once again, we’re hosting our iconic secret garden party and a series of founder dinners in our private mansion.
Events I’m hosting
Mar 12, 13, 15 | 🥂 “off menu” – a ceo dinner at a private mansion (Austin)
Mar 14 | 🤫 secret austin garden party (Austin)
Resources
📌 Unofficial Events List for SXSW 2026 — a curated list of events and parties happening around South by Southwest, updated daily (bookmark this)
📝 Submit your event to our events list: Submission form.
💬 Connect with others going to SXSW: Join our group chats.
Get involved!
🤝 I’m looking for FOUR young, ambitious people to shadow my team and help us with our March 14 party. I'll teach you everything I know, pay you for your time, invite you to our private mansion, and take you to lunch (what's the best bbq in Austin?). Please comment here if interested.
🙋 Apply to volunteer to join the A-team and help with our secret garden party on March 14.
📌 Andrew’s Bookmarks
My favorite links to help you be wiser and more creative.
Happy Ambition by Ben Casnocha – What’s the deeper reason why successful and wealthy people continue to sacrifice happiness for more money and achievement? Ben has a great take here.
In-Person Conversation Skills by Ben Casnocha – Soft skills are new hard skills, and with future generations spending more time behind screens, I’m afraid we’ll lose conversation as an artform. A useful refresher.
The 20 Greatest Decluttering Tips of All Time by No Sidebar – I hate clutter. I can’t work if my place isn’t clean, I can’t think if things aren’t in order, and I’m constantly optimizing for less. I subscribe to the belief that things can own you instead of the other way around. If you’re anything like me, you have to read this.
A Few Things I’m Pretty Sure About by Morgan Housel – Morgan just released his new book, so I’ve gone down a rabbit hole on this old stuff. He has some gems there, including this piece on life advice.
💃 Tech Community Plugs
Resources for entrepreneurs, investors, and tech professionals.
💸 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.
🚀 Have a startup idea you’re considering building? Builders Between Ventures is a validation sprint with Forum Ventures’ Studio to pressure test your thinking, understand the market, and get clarity on whether it’s worth pursuing. Apply here.
⭐ RARE OPPORTUNITY: My friend Andrew D’Souza is helping 100 founders raise their rounds before the end of the year. Fill this out.
🏢 Looking for an office space in NYC? I know of a few great spots opening up. Hit reply if you’re searching.
🧮 Need a CPA? I’ll introduce you to Alex, who I’ve been working with for the past three years. He’s excellent and specializes in tax support for high-earning individuals and entrepreneurs. More info here.
🗣️Wispr Flow – Your time is way too valuable to waste typing. Use Wispr Flow instead. This is by FAR my favorite productivity tool.
⌨️ Kondo – The best LinkedIn tool money can buy. Kondo is Superhuman for LinkedIn DMs. It turns your LinkedIn inbox into a lightweight CRM – you can label, sort, archive, and do a bunch of stuff amazingly fast. Get it here.
🤝 Looking to hire fast? My friends at Morpheus Talent specialize in helping you find GTM business and engineering talent at startups. Learn more.
🍽️ 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.
🏦 Fidelity Private Shares – 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.
🏃 Superpower – Achieve peak performance and improve your health by tracking 100+ biomarkers to get a comprehensive view of your body and get a customized action plan (P.S. I invested in this company!) Learn more.
🇺🇸 Looking for a US immigration lawyer? Reply here for an introduction to the lawyers I recommend for O1A/EB1 visas.
🚴 Equinox – Reply here for a free trial and discounted membership.
What other perks should I include? Let me know.
🖼️ Behind the Scenes
A few weeks ago, I launched The Shortlist, our new events and media company centered around hiring. We want to build the number one hiring event in New York: the place where breakout startups go to hire, and top talent goes to find their next opportunity.
Since then, we’ve hosted our first Founder Showcase with over 200 applications and six incredible CEOs on stage (see the recap here). Also, wow - this is my favorite video by far.
We also produced a print magazine, led by Maks on my team, and are now planning our next showcase on February 23.
One thing I’ve reflected on is how much I love the 0→1 of building a brand from scratch. Ideating, creating the concept, designing it, putting the team together, bringing it to life - and then seeing it manifest in the real world. It’s incredibly fulfilling. I haven’t felt energy like this since starting my mixers five years ago.
It’s a reminder to keep something in your life at the 0→1 stage. It might be a business, a hobby, or a new skill. We need something that brings back the childhood wonder of creating something new.
Andrew you want a young ambitious person for your events in Austin, look no further than me. I am obsessed. Check my references on jamesfloyds.world/references, or my LinkedIn.com/in/jamesfloydl, or my life resume Instagram.com/jamesfloydsworld
align your thoughts, feelings, intentions, and actions with expansion instead of contraction, alwayssssss