Join me live in San Francisco on Wednesday, June 17 to celebrate 400 episodes of the How I Invest podcast! Apply to attend 👉 partiful.com/e/9BxsWwarZx2uk… I’m bringing together an exclusive group of prior guests, allocators, and investors for an evening of drinks, hors d'oeuvres, and a toast to this milestone. It has been an incredible journey, and I’m grateful to the guests and supporters who have helped make 400 episodes possible. Space is limited, so don’t wait to register! Special thanks to our sponsor partner @sydecario. Date: Wednesday, June 17 Time: 5:30 PM – 7:30 PM PT Location: San Francisco, CA (venue shared post-registration) #HowIInvest #400Episodes #VentureCapital #PrivateMarkets #LP #Allocator

𝐁𝐑𝐄𝐀𝐊𝐈𝐍𝐆: 𝐖𝐡𝐚𝐭 𝐢𝐟 𝐭𝐡𝐞 𝐬𝐦𝐚𝐫𝐭𝐞𝐬𝐭 𝐢𝐧𝐯𝐞𝐬𝐭𝐨𝐫𝐬 𝐚𝐫𝐞 𝐥𝐨𝐨𝐤𝐢𝐧𝐠 𝐚𝐭 𝐭𝐡𝐞 𝐰𝐫𝐨𝐧𝐠 𝐝𝐚𝐭𝐚? We’re living in the most confusing market in venture history. LPs are trying to find “ground truth” — but when the ground keeps shifting, how do you anchor conviction? I sat down with Narayan Chowdhury, Co-Founder & Managing Partner at Franklin Park ($21B AUA), to unpack how elite LPs are navigating a world where: - The data sets everyone relies on are biased or incomplete - Founders have more power than ever - The next generation of managers will look nothing like the last Narayan breaks down: - How to separate signal from noise - Why founder “love” is the new moat - And how the best LPs quietly build an edge through relationships, not spreadsheets It’s one of those rare conversations that leaves you with more questions than answers — and that’s the point. We’d like to thank @AlphaSenseInc for sponsoring this episode! #HowIInvest #VentureCapital #PrivateMarkets #LPInsights #AIInvesting Link to Podcast in Comments Below 👇

BREAKING: What if your fundraise didn’t depend on luck… but on math? Most GPs think the goal is to “pitch better.” But top fundraisers like Yasmine Lacaillade know it’s about something else entirely — building a living, breathing LP pipeline that converts. Here’s what we uncovered :👇 - Why Fundraising Never Gets Easier — even at Fund VI - The 5% Conversion Rule (and why you need 700 active LPs) - How “Networking” beats “Nurturing” for long-term success - The math that makes or breaks a raise - And why the best fundraisers are secretly… enterprise sales pros Most people think it’s about relationships. The best know it’s about systems. #VentureCapital #Fundraising #PrivateEquity #LPs #HowIInvest

BREAKING: Most LPs think their only option for liquidity is selling their position. But what if you could borrow instead of sell? That’s exactly what Alex Simpson and his team at LiquidLP are building — NAV-based lending that lets investors unlock capital without losing their upside. Think: • 20–40% LTV against top funds like Sequoia or Andreessen • High-single to low-teens rates depending on portfolio quality • Weeks (not months) from application to funding • Fully bespoke terms for family offices, GPs, and smaller institutions It’s the next evolution of secondaries — discreet, efficient, and aligned with conviction-driven investors. We broke down: - When a NAV loan beats a secondary - How to diligence illiquid portfolios fast - Why purpose of funds matters more than people think - The “standby liquidity” model reshaping fundraising #PrivateMarkets #Liquidity #AlternativeInvesting #HowIInvest #Secondaries Link to Podcast in Comments Below 👇

Not all markets are efficient. In fact, there’s a $100 Trillion market that still conducts half its business over the phone. Yes, the phone. 📞 Meanwhile, equities, options, and futures have been automated for decades. 🤯 One team is working to change this… 💡 @djacksonparker and his team at @_MomentHQ, backed by Index Ventures with a recent $36M Series B 🚀, are rearchitecting how bonds are traded, portfolios are built, and wealth managers operate. Here’s what blew me away in our conversation: - Dylan knew nothing about fixed income when he joined Citadel. Within years, he was building their fixed income algo trading desk. - Today, nearly half of bond trading volume is still negotiated manually by phone (yes… still). - A custom muni bond portfolio for a retiree used to take 2 hours to build. Moment’s software does it in 5–10 seconds. - Tax-loss harvesting is even more powerful in bonds than equities — because bonds mature without creating offsetting capital gains. - Why the wealth management market (RIAs, roll-ups, aggregators) may actually leapfrog institutions in automation — because managing 10 million portfolios is literally impossible without it. - Culture matters: Dylan learned at Citadel that small teams of exceptional people >> huge teams of good people. That mindset is baked into Moment’s DNA today. This episode is not just about trading. It’s about the future of: - How retirees get predictable income - How RIAs and wealth advisors scale - How “boring” markets can turn into the next massive fintech wave 👇Do you think bonds will be disrupted in the next 5-10 years? Should I invest in this company if given the opportunity (genuinely curious)? Comment below #FixedIncome #WealthManagement #FinTech #Investing #HowIInvest Link to Podcast in Comments Below 👇

🚨 Ever wondered what really makes top Limited Partners (LPs) say “yes” to a General Partner? 🤔 👇 I just unpacked the “Top 10 Things LPs Look for in a General Partner” after a candid conversation with Matt Curtolo, CAIA (ex-Hamilton Lane, MetLife). You might be surprised which factors make—or break—the deal. 👀 Here’s a sneak peek: 🔑 Mission-driven vision (why you do what you do) ⚡ Conviction over consensus — who stands out? 🌍 Understanding your market role & unique edge 🤝 Real alignment with LP goals 📈 Track record and adaptability to trends But that’s just scratching the surface. Are you missing the #1 factor LPs value most? 👉 👇 Are you a GP or LP? Share your biggest surprise, or let me know if you’d add anything to the list. Special thanks to those who shaped this conversation— John Merrill and Brad Conger; Abe Finkelstein of Vintage for highlighting the importance of upside in co-investing; Steven Kaplan from Chicago Booth for his research on PE and VC; and Daniel Kimerling of Deciens Capital for his contributions. #PrivateEquity #Fundraising #LPInsights #VentureCapital #HowIInvest Link to Podcast in Comments Below 👇

🏆 What do Figma, Ethereum, and Loom have in common? (Hint: It’s not just billion-dollar valuations!) 🏆 They are all part of Peter Thiel’s Fellowship, where 1 out of every 10 companies have achieved unicorn status. ✨ Twelve years ago, Peter Thiel launched the Thiel Fellowship-an experiment so exclusive it’s ten times harder to get into than YC. 💡 Each year, just 20 visionaries get $100K to drop out and build. The result? ✔️10% of Fellows have built billion-dollar companies 🔥 1/3 have created $100M startups 🚀 Alumni include the likes of Figma, Ethereum, and Loom But here’s the real secret: The Thiel Fellowship has built one of the most elite peer groups in the world. 🌎 Every day, fellows and alumni crowdsource solutions to M&A headaches, scaling roadblocks, and other challenges that come with growing hyperscale startups. 🦄💬 I interviewed @zaidrmn, Founder & CEO of @FlexSuperApp on this and how to build an elite culture. We’d like to thank @juniper_square for sponsoring this episode! #VentureCapital #DeepTech #Startups #EngineeringLeadership #SpaceX #Entrepreneurship #HowIInvest #TechInvesting #HardwareStartups #ThielFellowship #Startups #AI #Fintech #Leadership #Innovation Link to Podcast in Comments Below 👇

🚨 Is the 60/40 Portfolio is Dead? I sat down with @BowmanJohnL, CEO of the @CAIAAssociation, to discuss this topic and to break down the biggest shift in asset allocation: the move to the Total Portfolio Approach. We talk about: - Why the 60/40 model no longer works 📉 - The trap of “false diversification” 🪤 - How too much liquidity hurts long-term returns 💸 - Why most family offices get alternatives wrong ❌ - The right way to build a private market program ✅ - How platforms like iCapital and Alto are reshaping access 🔓 - What cutting-edge portfolios will look like in 2030 🔭 John also shares what CAIA is doing to close the education gap as trillions move into alternatives. We’d like to thank @juniper_square for sponsoring this episode! #VentureCapital #AssetManagement #FamilyOffice #PrivateEquity #AlternativeInvestments #OpenLP #PortfolioConstruction #HowIInvest Link to Podcast in Comments Below 👇

🎙️ Just dropped another episode with @jamiegull of Wave Function Ventures and former long time SpaceX engineer. This was my first deep dive into how @elonmusk builds great organizations 🚀 Here’s a sneak peek at what we uncovered: ⬇️ - SpaceX Secrets REVEALED: 🚀 Jamie spills the beans on the insane culture, Elon's hands-on leadership, and what it REALLY takes to survive there! Ever heard of the "Responsible Engineer"? 🧐 It's wild. - Deep Tech Investing 101: 💰 Forget software; Jamie's betting on ATOMS! He explains why MBAs often fail, the Techno-Economics hurdle, and the ONE question that determines if a deep tech startup is investable. 💸 - Elon Musk's Playbook: 🧠 One-on-one meetings? Unblocking bottlenecks? Jamie shares firsthand experiences working directly with Elon and reveals his unique problem-solving strategies. 💡 Curious? 😉 ➡️ Listen to the full episode to learn: - The 3 types of people who work at SpaceX (and which one YOU are!) 🧑‍🚀 - Why technical expertise is EVERYTHING in deep tech. 🤓 - How SpaceX shaped Jamie's expectations and investment philosophy. 🌟 #VentureCapital #DeepTech #startups #EngineeringLeadership #SpaceX #Entrepreneurship #HowIInvest #TechInvesting #HardwareStartups #Innovation Link to Podcast in Comments Below 👇

🤯 How did Michael Kim and Kelli Fontaine of Cendana Capital spot a future VC star last year? (Hint: she was only 24!) 🤯 I just dropped an inspiring "How I Invest" episode with @paigefinnn of @behind_genius. Hearing how she built her fund and attracted one of the world's top LPs before turning 25 is mind-blowing! 🚀 This episode is gold for anyone navigating the world of VC, startups, or fundraising. 🔑 Here's what Paige revealed: - The "X-Factor": It's not just about the numbers. Cendana saw Paige's unique ability to build narrative gravity and community. ✨ - Media as a Magnet: Building a media presence (yes, even a children's book!) drew LPs in. 📚 - Turning "No" into "Yes": How Paige flipped Cendana's initial pass into an anchor LP position in Fund 2. 😱 - Plus, we dive into Paige's founder archetype and the surprising data from $100B exits. 🤯 “You either do or you don’t. There is no in between. Raising a venture fund is binary. You need a thesis with deep conviction and the ability to align LPs and founders around it.” - Paige Finn Doherty Ready to hear the full story and unlock Paige's secrets?🔑 See comment section for full episode! We’d like to thank @joinrepublic for sponsoring this episode! #venturecapital #founders #funding #cendana #paigefinndoherty #geniusventures #howIinvest #podcast #emergingmanagers #linkedin

Steelers took out Chubb to 🤦🏻‍♂️

Today I learned!

What's d probability that I'm able 2 predict demand-supply situation and hence, the future price of say, gold/real estate/crypto, vs what's d probability that I'm able to estimate continuing demand of paints (say), and the continuing market share for Asian Paints? #HowIInvest

If you'd use "mundane" to describe your financial life, I think that's a good sign you're doing it right! I received a beautiful framed version of this @behaviorgap sketch, which accompanied my chapter in the book #HowIInvest My Money. Thanks, @brianportnoy @ReformedBroker !

This discussion is full of powerful messages, especially for the newbies in the market. Kudos to @ReformedBroker, @brianportnoy and all the contributors in #HowIInvest My Money. Still halfway, but the book is full of gems. I really liked the picture illustrations by @behaviorgap.

I am sometimes guilty of saying things are "so much fun!" when they weren't actually that much fun for me. But this chat with @brianportnoy @ReformedBroker @morganhousel to discuss "How I Invest My Money" was actually quite a bit of fun! #HowIInvest youtube.com/watch?v=ZbU3VD51…

Squee! My custom @behaviorgap sketch for #HowIInvest arrived.

Look what arrived from my friends ⁦@harrimanhouse⁩. So excited to collaborate with ⁦@ReformedBroker⁩ & ⁦@brianportnoy⁩ on the project. A special shout-out to ⁦@behaviorgap⁩ his engaging illustration. #howiinvest

Just finished @DasarteYarnway's chapter. A real life freedom story. Using his powers for good to pour into others from bootstrapped entrepreneurs to developing neighborhoods in Liberia. Onward to greatness. (something that encourages me every time I see it) #HowIInvest

Look what arrived in my mailbox today. ⁦@behaviorgap⁩ ⁦@brianportnoy⁩ ⁦@ReformedBroker⁩ ⁦@harrimanhouse⁩ #howiinvest