“This is the last time you’re going to see me graduate”
Molly Cantillon stated these words to her parents at her HIGH SCHOOL graduation. They weren’t amused…
Years later, she dropped out of Stanford, moved into a hacker house (sharing just a mattress topper), and raised money from OpenAI.
I sat down with Molly, founder of NOX, a company rethinking how humans communicate in this AI-native world. Despite being the youngest guest on my podcast, she’s got the most confidence.
If you’ve ever wondered what conviction looks like in Gen Z form, this one’s worth your time.
Here’s what I learned:
1️⃣ Conviction beats credentials: Molly dropped out of Stanford not because she had a perfect plan, but because she had an unshakeable belief that AI was creating a once-in-a-lifetime opportunity. When ChatGPT hit, she saw it as "a complete level playing field" where time spent with the models mattered more than pedigree.
2️⃣ Hire for whimsy, not resumes: Molly's first hire was a 17-year-old from Canada she found in Discord communities. She looks for people who do have a deep love for technology, which is usually evident in their early years.
3️⃣ Delayed gratification reveals character: Molly and her team share a love for running. It's not a hiring test, it's a shared value. People who can work through difficulty knowing there's something great at the end naturally gravitate toward each other. Those painfully long runs become the perfect metaphor for the startup grind.
Timestamps:
(00:00) - Introductions
(01:08) - Dropping out of Stanford
(09:48) - Molly’s first fundraise
(16:30) - NOX’s many iterations
(24:23) - PLG + the current and future state of communication
(33:45) - Growing the team and culture
(38:42) - Love for technology + delayed gratification
(42:53) - Highlights
(44:25) - Ceremonial Final Qs
Where do VCs get money from?
Welcome to LP land. The mysterious world where people who fund VCs live.
Nate Leung, Partner at Sapphire Partners and Co-Founder of OpenLP, gives us a peek into the backbone of the venture ecosystem, and it’s wilder than you think…
Episode 049 is live.
Here’s what I learned:
1️⃣ Great investors ≠ Great fund managers. You can pick winners all day. But if you can’t deliver trust, consistency, and a narrative LPs can sell internally, you won’t survive as a fund manager.
2️⃣ GP-LP fit matters. LPs represent causes, initiatives, and interests. These relationships last decades. Partner with the organizations you’re aligned with.
3️⃣ Every LP has different incentives. Some allocators want access to innovation. Some want brand and prestige. Some would rather be safely wrong than boldly right. Work with people who are structurally incentivized to want your success. Ask yourself, how are folks on the LP side compensated?
4️⃣ Investment decisions are often team sports. You may write the best memo in the world, but without trust and credibility, you won’t get far. Circulate opportunities and gauge appetite before decision time.
Timestamps:
(00:00) - Introductions
(01:30) - Sci-fi novels + being a parent + time travel
(07:08) - Origin stories
(09:18) - Great investors vs. great fund managers
(12:03) - GP-LP fit
(16:03) - LP incentive structures + signaling
(18:41) - Liquidity and secondaries
(21:21) - Why is LP land so mysterious?
(22:53) - CalSTRS + conflict of interest
(28:02) - Portfolio construction
(29:43) - GPs switching strategies
(31:08) - Are platform teams actually valuable?
(33:30) - Raising Fund I from track record and references
(34:00) - Pools of capital still investing in <$50M funds
(35:20) - Who/what decides fund size?
(38:05) - “Value-add” LPs
(39:26) - What is the biggest compliment an LP can receive?
(41:02) - What’s something you learned the hard way?
(44:04) - Ceremonial Final Qs
VC is a young person’s game.
More time. More energy. Stronger pulse on what’s next. It’s one of the few industries where being young is actually your edge.
But here’s what most young VCs get wrong: They try to think like their partners instead of developing their own taste.
Chauncey Kerr Hamilton, Partner at XYZ Venture Capital, breaks it all down in episode 048 of New to Venture.
Here’s what I learned:
1️⃣ Time management is everything. If you like poker, host a poker night for your founder friends. If you have kids, take them on your work trip. Feed two birds with one scone. Blend personal and professional. It’s the only way to survive.
2️⃣ Your job as a young VC? Understand what your firm wants AND figure out your own taste in founders/companies, then find a way to marry them together.
3️⃣ Get good at explaining why you’re excited. You’ll need to convince committees, later-stage investors, and LPs. If you can’t articulate your conviction, you won’t close the deal.
4️⃣ Do post-mortems on failed deals. What went wrong? What did you miss? Your blind spots will haunt you if you don’t find them early.
5️⃣ Winning deals gets easier over time. More people in your corner = more references. Chauncey’s formula: Unvarnished feedback + unwavering support + speed to conviction. Speed IS support.
6️⃣ VCs will never know more than founders about their space. But they know the venture game. What gets funded? What do growth investors look for? What’s changing? A great investor should provide a birds eye view of the startup ecosystem.
Young VCs have the time, energy, and ability to relate to young founders. Use that to your advantage.
Episode 048 is live. Time to level up.
Timestamps:
(00:00) - Introductions
(01:03) - Chauncey’s path to venture
(04:02) - The Chief of Staff role
(05:26) - Gardening! + Parallels between life and investing
(09:42) - Time management
(11:53) - What changes with tenure?
(15:00) - Developing your taste in companies
(17:35) - Missing out + winning deals
(21:37) - Treating founders well
(24:30) - How Chauncey wins + Providing value
(27:42) - Consensus thinking
(30:52) - Mentoring
(36:43) - Highlights and lowlights
(40:42) - Ceremonial Final Qs
My first in-person podcast. Ever.
I kept thinking about it. A LinkedIn lurker who’d never posted. A kid with a computer and too many questions about venture.
Now I’m sitting across from Bryan Kim at a16z. Real conversation. Real energy. Pinch-me moment.
Bryan’s invested in companies that became the fabric of our society. Partiful, how we gather. Cluely, the AI assistant everyone’s talking about. ElevenLabs, the voice of AI. BeReal, the most authentic social media platform. Tune in to hear how he did it.
My key takeaways:
1️⃣ In a world where AI models are changing constantly, momentum becomes the moat. Momentum = Shipping velocity + distribution.
2️⃣ Super apps haven’t been built yet because they need their core competency to be at ~99% adoption first. Messaging, payments, and social media are all too fragmented.
3️⃣ Know your zone of competence. Own what you crush at, but also own what you suck at. It’s okay to not be good at everything.
4️⃣ Almost everyone in venture comes from somewhere impressive. Stanford, Goldman, Mckinsey, ex-founder. So what? Be a beginner. Nothing is beneath you. Do the work and soak everything up.
5️⃣ Your partners won’t always agree. If you think you know something and have done the work, have conviction. That’s why you have a seat at the table!
47 episodes ago, I started with a question. Today, I’m getting answers from the people shaping our future.
Sometimes you just gotta start.
Timestamps:
(00:00) - Introductions
(01:06) - The power of “Where are you from?”
(02:11) - Origin stories
(03:56) - Korean venture capital + Super Apps
(08:57) - Momentum is the moat
(13:49) - High quality distribution
(17:23) - Creating momentum
(24:15) - Bryan’s zone of competence
(27:46) - Highlights and lowlights
(35:13) - Ceremonial Final Qs
“If you have to ask someone to be your mentor, they are not your mentor.”
Meet Grace, a partner at Amplify Partners and the person that dropped that massive truth bomb. In our conversation, Grace didn’t hold back. And honestly? The VC industry needs more people willing to say the hard thing.
Here are some of my favorites:
1️⃣ Work-life balance in VC? No shot. To compete against the best investors, the game demands everything.
2️⃣ Young VCs need exposure, not expertise: Hear 1000 pitches. Meet 1000 founders. Taste and intuition comes from volume.
3️⃣ Belief compounds: ”Having someone tell you that you’re amazing 1000 times changes everything.” We drastically underestimate the compounding effect of belief. One person’s consistent faith can reshape an entire career.
4️⃣ The VC investor mindset: “I don’t think to win, I think to help." The best investors don’t keep score with founders. They aim to create value and showcase their loyalty.
5️⃣ The generalist VC is dying: Watch the exodus happening right now. Partners leaving mega-funds to build specialized, artisanal firms. The future belongs to those who pick a lane and own it.
What broke my brain?
Venture Capital is fundamentally a series of transactions. Buy equity. Sell equity. Repeat.
But here’s the paradox that Grace helped me see: The LEAST transactional VCs build the BEST portfolios.
Why? Because helping without keeping score creates trust. Trust compounds. In a game built on reputation and relationships, trust is the ultimate currency.
Grace's Spotify playlist: Raving 101 - there is more to love than GenAI
Timestamps:
(00:00) - Introductions
(01:58) - EDM & traveling
(06:42) - Grace’s new show: Get with it
(08:40) - Work-life balance and Grace’s outlook on venture friends
(10:23) - Grace’s career arc + mentorship
(17:06) - Specializing and being a technical investor
(21:38) - Menlo Ventures → Amplify Partners
(24:24) - Current state of venture
(30:06) - Grace’s mindset!
(32:07) - Highlights and lowlights
(34:33) - Ceremonial Final Qs
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When everyone said it was too early to invest, Manu Kumar, founder of K9 Ventures and HiHello, said it was too late. Meet the man who coined the phrase “Pre-seed.”
In 2008, Manu Kumar saw something others missed. While VCs were waiting for traction, the best founders were building in garages with credit cards. So he coined a term that would reshape how we think about early-stage investing: Pre-Seed.
In episode 045 of New to Venture, Manu and I dive deep into what it really takes to spot greatness before anyone else does. From his time building companies to investing at the earliest stages, his insights hit different. This conversation challenged everything I thought I knew about venture. The truth that stuck with me? “You cannot be in venture without having lowlights. The successes get amplified and the failures get swept under the rug.”
My key takeaways:
1️⃣ You never really learn to be a CEO. Every company and every problem is unbelievably nuanced. There’s no playbook, no shortcut. Each journey demands its own map.
2️⃣ Hire only when you’re hurting: Never hire in anticipation, wait until you feel the pain. Be slow to hire, fast to fire. Working with someone reveals more than any interview ever could. Implement trial periods during your hiring process.
3️⃣ Grit beats everything: Manu looks for “insane perseverance in the face of complete resistance.” Companies don’t fail because of competition or markets, they fail when founders give up.
4️⃣ Incubate, then trust your gut: Taking breaks from problems lets your brain solve them subconsciously. New information may sway your perspective, but hone your relationship between instinct and action.
5️⃣ Clear commands win wars: “If you’re commanding an army, you have to give clear directions.” Being a founder is about guiding people toward a shared mission. Ambiguity kills momentum.
6️⃣ Find your investor - strategy fit:No VC strategy is inherently right or wrong. It just has to align with who you are. Manu does high-conviction, concentrated bets on people. What type of risks excite YOU?
7️⃣ Job titles shape behavior: Give someone a title, they’ll do what that title entails, not whatever the company needs. Be intentional about how you label roles.
8️⃣ Same problems, different scale: Companies of vastly different sizes often face identical challenges. The scale changes, but the fundamentals remain.
9️⃣ Pick your hard: Fundraising for a venture fund is 10x harder than raising for a startup. But operating a company? That’s 10x harder than running a venture fund.
Timestamps:
(00:00) - Introductions
(01:25) - Manu’s love for dogs + How K9 Ventures got its name
(03:13) - Manu’s most memorable founder story
(05:18) - Origin stories
(08:23) - Tough moments along Manu’s early journey
(11:05) - Founder DNA
(16:35) - Trusting your gut
(18:05) - Founder behavior
(20:35) - K9’s investing approach
(24:45) - Similarities and differences between building a startups vs. investment fund
(30:02) - Chief Firestarter
(32:37) - HiHello
(36:51) - Highlights + getting acquired
(40:32) - Lowlights
(41:57) - Ceremonial Final Qs
🎯 Why Specializing as a VC Is a Game Changer 🎯
Natan Reddy, Principal at Ironspring Ventures, unpacks the hidden edge of being a specialist investor in industrial tech. In episode 044 of New to Venture, Natan and I get into the weeds of early VC life, from building your network from scratch to hosting high-impact events. If you’re looking to supercharge your first few years in venture, this one’s for you. Tune in!🎙️
Natan and Ironspring Ventures are hosting an invite-only digital industrial breakfast for NYC Tech Week on June 3rd. If interested, apply to attend here: https://partiful.com/e/ggOlgpdXwNcjgrCraFsP
My key takeaways:
1️⃣ Know how much of a software player you want to be: In industrial tech, hardware is lower margin and capital intensive. Decide how deep into software you want to go.
2️⃣ Blitzscaling rarely works in industrial: Long sales cycles and slow adoption are the norm. Don’t force consumer-style growth tactics where they don’t belong.
3️⃣ Specialization attracts community: Go deep in a sector you love. Passion and expertise naturally pull in people who align.
4️⃣ Master the networking flywheel: Organic connections, events, content, and pure outbound scraping, each fuels the next. Play the cycle right and your network compounds.
5️⃣ It’s all about the people: We all know people make or break the job. Be kind. Be high integrity. Be a high-quality human. Surround yourself accordingly.
Timestamps:
(00:00) - Introductions
(01:19) - Speaking at CB Insights healthcare conference
(04:34) - Origin stories: Bay area vs NYC
(07:59) - Origin stories: Career path
(12:06) - Industrial Tech
(14:10) - Challenges with investing in Industrial Tech
(18:14) - Great businesses vs. venture backable companies
(20:34) - Benefits of being a specialist
(23:26) - Why early-stage?
(24:26) - Growing and building your network
(31:29) - Highlights
(34:04) - NYC Tech Week Industrial Tech Breakfast!
(35:39) - Ceremonial Final Qs
🔥The Blood, Sweat & Capital Behind a VC Firm 🔥
Jonathan Lehr, co-founder and General Partner at Work-Bench, brings a rare mix of enterprise GTM expertise, community-first values, and long term consistency to early-stage investing. In episode 043 of New to Venture, Jon pulls back the curtain on what it really takes to build a VC firm from scratch, from Fund I to the recent $160M Fund IV! This episode is packed with practical wisdom for anyone serious about raising their own fund. Don’t miss it! 📈
My key takeaways:
1️⃣ Be Intentional About Hosting: Define the goal, curate the room, and design for serendipity. Collaboration follows when the right people collide with aligned incentives.
2️⃣ Serve Your Community: The more you give, the more chemical reactions you unlock. Momentum builds from meaningful contributions to founders, investors, and LPs.
3️⃣ Compounding is Key: Consistency and discipline in high visibility tasks separates the real players from the noise. It’s how you beat the masses and weed out the phonies.
4️⃣ Raising a Fund is Like Enterprise Sales: LPs are similar to long-cycle enterprise customers. It is all about building deep trust. Target 10x pipeline coverage!
5️⃣ Share Your Work: Take what you’re already doing and use it to create meaningful touchpoints. Share your theses, learnings, or processes. Eventually, your ideas and impact will draw the right people to you.
6️⃣ Sizing Your Fund: Take a bottom up approach. How many checks do you want to write? What ownership targets do you have? How much follow-on capital do you need? Having clear answers here will guide you to a target fund size. Not a random market number.
Timestamps:
(00:00) - Introductions
(01:24) - Jon’s NBA player comparison
(02:38) - New York Enterprise Technology Meetups + Hosting
(07:36) - Morgan Stanley to VC
(13:26) - Starting a firm without any venture experience
(18:30) - Naming the firm
(19:41) - Raising outside institutional capital
(26:54) - GP - LP fit
(29:24) - Fund size strategy
(34:09) - What changes and stays the same as you raise more money
(39:54) - Highlights and lowlights
(44:39) - Ceremonial Final Qs
🌱Lessons from a career crafted through serendipity 🌱
Bo Ren, Managing Director at SVB, has truly mastered the art of serendipity! In episode 042 of New to Venture, Bo takes us through the many twists and turns of her career and the valuable lessons learned along the way. We dive deep into mentorship, curiosity, and soft power. This one’s full of heart and wisdom, don’t miss out! 📚
My key takeaways:
1️⃣ Embrace Seredipity: Your early career doesn’t need to follow a rigid path. Although there is comfort in having a life plan, be open to unexpected opportunities and explore widely. Take on every side quest that seems interesting.
2️⃣ Bet on Yourself: Often, the safest path is the one with the least room for growth or fulfillment. Every meaningful pivot requires a touch of audacity. You won’t have all the answers, but betting on your curiosity and potential will almost always lead to a more fulfilling journey.
3️⃣ Your differences are your edge: Don’t hide what makes you unique. Your differences end up becoming your superpowers. Especially in venture. VCs are looking for people who can push against their line of thinking.
4️⃣ Redefine Mentorship: We tend to overcomplicate and glamorize mentorship. A mentor isn’t someone with all the answers. A mentor is someone who has walked a few steps ahead and is willing to share what they’ve learned. Don’t look for a “perfect mentor” rather start building relationships rooted in shared ambition, vulnerability, and genuine care. As a mentee, you should be building a “goodwill bank account.” Give when you can, help where you’re able, show up as your authentic self.
Timestamps:
(00:00) - Introductions
(02:43) - HBO series: Industry + Who do you identify with?
(06:34) - Setting intentions and New Years Resolutions
(10:02) - Key turning points in Bo’s career
(14:18) - Parents and taking the big swing
(15:53) - Falling in love with startups(20:15) - Getting vocal on social media
(24:33) - Creating a personal IP and an easeful life
(29:03) - Soft power and invisible power laws
(38:19) - Mentorship
(42:47) - Highlights and lowlights
(46:51) - Ceremonial final Qs
🚀 Tips from a “full-stack” VC investor! 🚀
Crissy Costa Behrens, Principal at the powerhouse Insight Partners, has done it all. From being an operator, early-stage investor, growth-stage investor, and board member, her wide-ranging experience gives her a unique edge in venture. In episode 041 of New to Venture, Crissy shares her journey and top advice for the next generation of VCs. Don’t miss this one! 🎧👇
My key takeaways:
1️⃣ Be smart and lazy: Optimize for actions that have asymmetric upside. Focus on the inputs that have the biggest impact.
2️⃣ Scrappiness wins: There is no one right way to do venture, but there are plenty of wrong ways. Hustle, creativity, and resourcefulness can be a valid differentiator.
3️⃣ Conviction closes deals: Whether you’re at a big firm or a small one, strong belief in a deal is what ultimately gets it across the finish line.
4️⃣ Get comfortable with no control: Startup outcomes are almost completely out of your hands. From market swings to global shifts to random circumstances, there is always unlimited uncertainty. Learn to embrace it.
Timestamps:
(00:00) - Introductions
(01:44) - Crissy’s travel through Patagonia
(02:59) - Crissy’s podcast: 52 Founders
(06:43) - Does having a child make you a better investor?
(07:49) - Origin stories
(11:25) - Key learnings from Crissy’s time at Primary
(12:26) - Transitioning to growth equity
(14:41) - Investing in Jasper
(17:22) - Do founders treat you differently based on firm?
(20:38) - How Crissy wins + having a prepared mind
(25:36) - Highlights
(28:25) - What does a good board meeting look like?
(30:00) - Lowlights
(31:43) - Ceremonial final Qs
Many of my venture friends have raved about Peter, Founder at Stellation Capital, and now I completely understand why. From founding Rough Draft Ventures, HackHarvard, and Harvard Ventures(just to name a few), he’s become a cornerstone of the venture community. I got my start in venture through the Boston startup ecosystem, and I’ve been so fortunate to experience firsthand the ripple effects of his impact.
In episode 40 of New to Venture, Peter and I take a walk down memory lane, breaking down the traits that make him such a standout investor. Plus, we geek out over Magic: The Gathering and modding gaming devices. Tune in!
My key takeaways:
1️⃣ Creators have an edge: All VCs allocate and advise, but few create. If you’re early in your VC journey, build something. It could be content, a community, an organization, an initiative, or a product. Creating tangible impact attracts mentors, opportunities, and meaningful connections.
2️⃣ Avoid a zero-sum mindset: Focus on creating value for the broader community rather than competing for a fixed pie. A rising tide lifts all boats; strive to be the force that elevates everyone.
3️⃣ Spot potential early: The ability to recognize greatness before the world does is a superpower. Don’t rely on pedigree. Trust your instincts and invest in people ahead of the curve. Also, playing a role in the rise of future leaders isn’t just good business; it’s deeply rewarding!
4️⃣ Specialize, then rotate: For early VC folks, master one or two areas while staying flexible. Once you have a strong grasp of the landscape, explore new verticals and industries. Get comfortable becoming an expert, over and over again.
5️⃣ Find your signature investing style: Whether it’s how you source, support, or select, develop an authentic approach that differentiates you.
6️⃣ Find your signature learning style: Discover how you absorb information best. Whether it is through books, podcasts, conversations, or other means. You should be continuously consuming information. The more mental models you integrate, the sharper your decisions and insights will become.
Timestamps:
(00:00) - Introductions
(02:30) - Magic the Gathering + Modding Xboxs
(07:02) - Origin stories
(16:26) - Traits helped Peter grow
(21:45) - The birth of Stellation Capital
(29:13) - Peter’s first firm hire
(33:46) - Highlights and lowlights
(38:08) - Ceremonial final Qs
This is the hidden truth about product growth & venture capital!
Episodes like this are why I started the show. Charley Ma, Co-Founder and Managing Partner at Pathlight Ventures, is a true master of product growth. From being the first business hire at Plaid to the Head of growth at Ramp and Alloy, Charley has helped scale some of the best companies of this generation! Charley has a sharp eye for finding great teams and products early. Learn how he does it on episode 039 of New to Venture!
My key takeaways:
1️⃣ VCs often say "Keep us updated as you continue to build" to maintain optionality. The best way to respect each other's time is by providing honest feedback.
2️⃣ Optimize your career by surrounding yourself with great people. It not only makes each day more enjoyable but also unlocks hidden exponential growth. Find a way to work alongside the smartest, most brilliant minds you can.
3️⃣ Raising venture capital is the easiest and fastest way to kill your company! The vast majority of companies should not be venture backed. VC backed companies have a unique set of expectations from their investors to grow rapidly. In the grand scheme of business, it is an unnatural way of building and scaling companies.
4️⃣ Charley looks for the following traits in founders: Hyper intelligence, extreme ambition, high resilience, and strong storytelling abilities.
5️⃣ There is something truly special about being a founder's first "yes." Being a first believer in someone's idea is a strong foundation for a deep relationship.
6️⃣ Refine your understanding of your gut instincts, both their strengths and weaknesses. Use rational frameworks to make sense of your subconscious feelings.
Timestamps:
(00:00) - Introductions
(02:08) - Japanese anime + Fansubbing!
(04:33) - The rebel alliance
(06:59) - Getting pitched live with an audience
(09:17) - Origin stories
(15:27) - Growing product
(21:16) - What does great look like?
(24:33) - Angel investing
(27:31) - Deciding to raise a fund
(30:14) - Value-add VCs
(32:48) - Branding as a VC firm
(36:29) - Hiring top talent
(38:33) - Highlights and lowlights
(42:38) - Ceremonial final Qs
VC relationships aren’t built in term sheets - they’re built over time 🤝⏳
In venture, the long game matters. Both in supporting companies from day 1 and in building lasting relationships. Megan Kelly, Partner at Threshold, joins me on episode 038 of New to Venture where we discuss tips and tricks to make the most out of your early years as a VC investor. Megan brings incredible insights from her time at First Round, Threshold, and beyond. Tune in!
My key takeaways:
1️⃣ Your network building strategies change over time. As a young VC, you spend your nights going to happy hours, events, pitch nights etc. The natural progression as you become more senior involves more curated and intentional gatherings.
2️⃣ When you start your first role in VC, join as many pitch calls with your manager as you can. Take notes of every question they ask. Asking the right questions is a huge part of the job and where mentors can be very helpful.
3️⃣ VC relationships are about the long game. Be intentional about the people you surround yourself with. Understand the qualities and traits of people you enjoy being around. The best way to find the right fit? Be authentic. It’s easier said than done in a world where deals are the currency, but it makes all the difference.
Timestamps:
(00:00) - Introductions
(02:01) - The other “Megyn Kelly” + VC Moms
(04:42) - Does having kids make you a better VC?
(05:47) - Work-life balance and priorities
(08:49) - Key turning points and origin stories
(13:44) - Swiss army knife vs. Specializing
(15:48) - Best practices for being a VC sponge
(17:44) - Questions to ask in a pitch call
(19:47) - Meeting special founders
(21:49) - Learnings from great organizations
(23:22) - Joining the Threshold team
(26:07) - Principal to Partner
(27:38) - how does Megan Kelly win? + Building genuine relationships
(32:01) - Ceremonial final Qs
“The mentee knows the rules, but the mentor knows the exceptions”
Derek Chu, Principal at FirstMark, is a wealth of knowledge when it comes to startups. In this episode of New to Venture, he shares his thoughts on the art of consumer venture capital, what “great” looks like, and his career journey so far. Some of my new favorite quotes are sprinkled throughout the episode, so don’t miss out!
My key takeaways:
1️⃣ Understand the value of asymmetric opportunities. What actions/projects have low downside, but limitless upside? How can you live an exponential life versus a linear life?
2️⃣ Organic usage in the wild is a helpful litmus test for a viral consumer product. Think about a product’s frequency of use, density and gravity. These are the markings of a truly special consumer product.
3️⃣ If your gut is telling you something that you can’t quite explain, keep thinking—relentlessly. Clarity comes with sustained reflection. As Voltaire put it, “no problem can withstand the assault of sustained thinking.” When it comes to your opinions, "I don’t know" isn’t a final answer, it’s just the starting point.
Timestamps:
(00:00) - Introductions
(02:20) - Derek’s turning points
(06:54) - Shifting into early-stage investing and technology
(08:27) - What does “great” look and feel like?
(11:26) - Missing out on Warby Parker and Uber?
(15:59) - Investing in Posh
(23:02) - Deep dive into consumer investing
(28:50) - Discerning top talent to join the investing team
(32:18) - The VC apprenticeship model + mentorship
(40:26) - Highlights and lowlights
(44:43) - Ceremonial final Qs
This conversation forced me to rethink my understanding of venture. 🤯
Yoni Rechtman, Principal at Slow Ventures, brings a keen eye and deep insight to the world of VC. In episode 036 of New to Venture, Yoni and I navigate between the nitty gritty and big-picture dynamics of the industry. His thoughtful approach and deep understanding of the game we play are on full display as he tackles some burning questions I’ve been dying to ask. This one was a blast.
My key takeaways:
1️⃣ Venture isn’t overly complicated. At its core, VC is about finding really awesome people with really awesome ideas and giving them money. If they’re right, they all can go on a nice vacation. Every firm has a different strategy that they deploy, but the nature of their work is always going to be the same.
2️⃣ Just because a deal is competitive doesn’t mean it's a good company. In fact, it could even be a negative signal. If a lot of VCs can understand an idea, many others can too, which usually indicates a super competitive category.
3️⃣ Mega VC funds and small VC funds play different games. Mega 5 billion dollar funds have to deploy $1.5B a year. They are in the business of deploying capital not parsing.
4️⃣ Study the history of startups, markets, and venture capital. It’ll help you understand what a good business looks like and whether it is the right time to invest. Understanding history is an important part to using pattern recognition the right way.
5️⃣ Think beyond the game – consider the meta game. It’s not just about who’s good and who’s not; it’s about understanding the deeper incentives at play. Who is structurally incentivized to collaborate with you? Why and how would someone work with you? Answering these questions are the first step to building the right founder and VC networks.
Timestamps:
(00:00) - Introductions
(01:55) - Yoni’s X profile picture + Strategic Online A**hole Theory
(06:22) - Slow Ventures’ approach to content
(09:26) - Competitive fundraises
(12:11) - Legible and illegible companies
(18:47) - Founder referral flywheels
(22:13) - Yoni’s origin stories
(27:17) - Best practices for thinking like a VC
(33:39) - What makes a Slow investor + apprenticeship model
(37:50) - Ceremonial final Qs
How pizza helped me land a legendary VC for my podcast?!?! 🍕
In late 2024, a once in a lifetime opportunity to work at the phenomenal Eniac Ventures popped up. It was a dream role for me. Being based in NYC, I overheard tons of positive feedback about the small, but mighty team and I was dying to be a part of their story.
If you’ve been tuning in to the podcast, you’ll know that networking is a key aspect to getting a job in VC. Through a few friends, I got connected with a member of the Eniac team and told them I’d be applying. They told me they had flagged my resume and I should be expecting an interview! I was unbelievably excited and couldn’t wait to compete for the spot…
One week passed, but no interview request came in. The timing was unlucky because it was a busy time for the firm and the person I originally connected with was out of office. Two weeks passed, and still no interview request…
If I didn’t do anything, I’d miss out on a chance to work with the people I admire. If it wasn’t a good fit, so be it. I at least wanted a shot on goal. I thought to myself “How can I be different?” and “How can I get their attention?” VCs get hundreds of emails a day, so a well worded cold email simply wasn’t going to cut it. So, I took a gamble and did the unthinkable…
I sent them a pizza. Delivered straight to their office. Using the name of the partner I’d hopefully be working with.
Moments after I got confirmation that the pizza was delivered, I started drafting up an email to them. Subject line: Did you enjoy the pizza? + I want to join your team :)
While drafting that email, I got an interview request.
Although things didn’t work out in the end, I got to meet the lovely Eniac team and got Hadley to join me on the show. Episode 035 is a very special one because the story of its creation starts with a NYC delicacy!
Key Takeaways:
1️⃣ It's a common pitfall to create false learnings from decisions. Good decisions can have bad outcomes and bad decisions can have good outcomes. There is a lot of unknowable information and a lot of luck in seed investing. Be very careful when drawing conclusions and relying on pattern recognition.
2️⃣ Companies make major pivots. As a seed investor, it's really hard to see what the company can become. Don’t kick yourself too much if you miss out early.
3️⃣ Gossip amongst investors creates a strong feeling of FOMO. FOMO is an incredibly powerful force. It can be the difference between a mega seed deal and a deal that barely gets done.
4️⃣ To be great at seed investing you need to have either a unique point of view/information or a unique relationship.
5️⃣ A partner should be able to do a deal by themselves. VC is a game of outliers. It is okay to shy away from consensus! This structure also allows for deals to get done quickly instead of partners having to play politics with the other firm decision makers.
6️⃣ Sourcing changes as you become more senior. Junior VCs start by communicating and networking with other junior VCs. It may be a good place to start, but those deals are usually already well known and competitive. Founder networks seem to consistently be the best for sourcing.
Timestamps:
(00:00) - Introductions
(01:54) - Mixing music and playing tennis
(05:51) - Does having kids make you a better investor?
(07:15) - Hadley’s biggest career turning points
(11:20) - Why build Eniac Ventures?
(13:29) - The importance of iteration and learning lessons
(18:42) - Being an early believer in AI
(20:35) - The essence of good seed investing
(23:31) - How the NYC ecosystem has changed
(27:28) - What separates the long lasting VC firms from the short ones
(28:54) - Eniac’s special structure and how they win
(33:23) - What it means to be a helpful VC
(34:48) - Sourcing and getting the right access
(38:35) - Highlights and lowlights
(41:09) - Ceremonial final Qs
There truly is no single right path into VC!
Christine Choi, Partner at M13, is one of the most interesting and introspective people I’ve ever met. From being on the founding team of Teach for America to putting together massive music festivals, Christine is a master executor! In episode 034 of New to Venture, Christine and I take a walk down memory lane as she shares lessons from the many different jobs she has had. Links to the episode are at the end of this post!
M13 is a phenomenal firm headquartered in LA. If you have the means, please stand with and support the LA community as they are going through a time of distress and tragedy.
Key Takeaways:
1️⃣ Get good at executing. If you have a track record and reputation of simply getting it done, the world is your oyster.
2️⃣ “Slow is smooth is fast” - Being thoughtful and having a prepared mind is a slow process, but it makes things smooth, which in turn, lets you move fast when the time is right!
3️⃣ Leadership doesn’t happen in a boardroom. Leadership happens in the real world where unexpected things happen. How you deal with it and how you empower team members defines a true leader.
4️⃣ You can’t build something substantial all alone. You need a strong team. You need to inspire, but also give them space to work their magic.
5️⃣ Good storytelling starts with authenticity, understanding your key differentiators, and where you shine. Some people show up well as a keynote speaker, blog writer, panelist etc. Find what makes you special! In a way that feels natural, find the proper medium to express your uniqueness. The last piece is understanding your audience. Where can they be found? What speaks to them? What are they looking for?
6️⃣ The VC comms and marketing world is so dynamic. It is extremely difficult to keep communication streamlined and efficient because there are so many different groups of people from founders, operators, other VC firms, internal team members, and LPs.
Timestamps:
(00:00) - Introductions
(02:14) - Traveling + Living an interesting life
(07:00) - Life is too short for a**holes
(08:56) - Being introspective + parents
(13:37) - Origin stories
(22:27) - Learnings from Richard Branson
(25:09) - Effective storytelling in VC
(27:39) - Why comms and marketing is so difficult
(30:00) - Highlights and lowlights
(33:22) - Ceremonial final Qs
This is the ultimate masterclass for building relationships with VCs!
In my many episodes of New to Venture, no one has been applauded as much as the illustrious Rebecca Kaden, General Partner at Union Square Ventures. It was such an honor to have her on the show to delve into VC relationships. Whether it is with a co-investor, board member, or friend, episode 033 will help take your relationships to a deeper level!
Key Takeaways:
1️⃣ A productive conversation amongst VCs has a high degree of trust, respect, and differing ideas! Young people in venture tend to have more transactional conversations, where sharing opportunities is the main priority. Push yourself to have conversations about ideas, interests and thinking. Hopefully, a conversation may sway your opinion on a company you’re looking at.
2️⃣ Networks get more valuable over time by what people contribute to them. The VC/tech ecosystem is a network. The more you put in, the more you’re going to get back 🙂
3️⃣ It's the natural course of a VC to start their network broad and then slowly find the people they can count on. Don’t feel the pressure to create your trusted circle, just let it happen naturally.
4️⃣ Although it may be nice to have co-investors who are low maintenance, have a good track record, and can follow on at high valuations, the best co-investors are believers, decision makers, and those who do the work!
5️⃣ Great board members “agitate when the water is calm, and calm when it is agitating.” When there is chaos surrounding the company, a strong board member will alleviate that stress. When things are calm, they push and help move the company forward.
6️⃣ Ultimately, deals are the currency of the VC world. If you want a fast-track to the top, get good deals done that your firm wouldn’t have seen if you weren’t there.
7️⃣ As a young VC, it's okay to have unoriginal thoughts. Just keep mashing and combining those thoughts with learnings from amazing investors until it sounds like yours! Simply put, that is what learning is.
8️⃣ Founder-VC calls shouldn’t be a VC bashing a founder’s idea. It should be two educated individuals sharing their hypothesis on the world and seeing if they are aligned!
9️⃣ A lot of VC investing is understanding the balance between patience and impatience. It's a hard, delicate, and nuanced dynamic. When is the right time to take things slow? When is the right time to throw the kitchen sink? Think about that balance as you grow your career.
Timestamps:
(00:00) - Introductions
(02:03) - Holiday traditions!
(05:00) - What makes a productive conversation amongst VCs?
(10:04) - Collaboration vs competition
(11:58) - Rebecca’s learnings from the legendary Bill Campbell
(13:55) - Collaboration vs competition pt 2
(16:16) - Good practices for finding your network
(22:04) - Good practices for being a good co-investor or board member
(26:47) - Rebecca’s origin stories
(32:57) - Building theses + original thoughts
(35:02) - Maveron → USV
(36:54) - Rebecca’s secret sauce
(39:51) - Ceremonial final Qs
Learn these 7 important things about VC from a legendary Midas List investor!
We’re starting 2025 with a bang on New to Venture! Nerd out with Ross Fubini, Founding Managing Partner at XYZ Venture Capital, on episode 032 about all things VC and beyond. This one is an episode for the ages because there is a heartwarming surprise guest appearance by another fantastic investor in the episode! Tune in 🙂
Key Takeaways:
1️⃣ Venture, even when successful, is very lonely! The feeling of success is very different from building a company. You are continuously “starting from scratch” with every new investment, while being a successful operator involves compounding baby steps forward.
2️⃣ The nature of Venture is lonely in a few ways. You either made the right decision or you didn’t. Your job as an early stage VC is completed long before the company ends up being successful. It's off tempo to the teams building the product, which is very disorienting.
3️⃣ Create systems and processes IMMEDIATELY after you didn’t get the outcome you wanted. For example, if you miss a deal due to timing, build protocol so you never miss a deal due to timing again. Use the emotional tension of failure to do something productive!
4️⃣ GovTech is a unique vertical. Good founders must have a notably strong GTM strategy. It is essential to win in this vertical.
5️⃣ Practice low-ego, high ability! Venture is notoriously filled with strong personalities. Having low-ego is a great way to be someone fun to work with.
6️⃣ Joining the right founder and VC pockets is a test of patience. Keep backing the best people in your current circles, then slowly climb up. JUST DO IT! The most efficient way to get good at something is to get started.
7️⃣ Figure out what your VC firm is good at and lean into it. If you join, wanting to shake things up and start new projects, it creates a ton of friction since your firm doesn’t understand it yet. Try your best to deeply understand how the firm thinks and makes decisions.
Timestamps:
(00:00) - Introductions
(02:04) - The Fubini Theorem and naming the firm
(05:19) - Ross’s origin stories
(09:31) - Building a tech company vs. a tech investing firm
(12:03) - Why Venture Capital is lonely
(17:45) - Creating smart processes
(20:50) - Surprise guest appearance! + GovTech founders + great people
(27:36) - How social media has changed Venture Capital
(31:48) - Breaking into founder networks
(39:42) - Highlights and lowlights
(43:32) - Ceremonial final Qs
What happens when a VC podcaster interviews another VC podcaster? 🗣️🗣️
It was such an honor to sit down with one of the biggest VC content creators in the game! Grace Gong, Host of the Smart Venture Podcast, has over hundreds of interviews with leaders in technology under her belt. Join us on Ep 031 of “New to Venture” to get the inside scoop on VC podcasting and beyond!
Key Takeaways:
1️⃣ “You are the average of the five people you surround yourself with the most.” People often think of this very literally, but this applies to content as well. If you spend a lot of time listening to a content creator, you’d be surprised how much it rubs off on you! Be a conscious consumer.
2️⃣ If you are thinking about making an angel investment, you must be very comfortable with that investment turning to 0.
Timestamps:
(00:00) - Introductions
(02:20) - Meeting famous people in tech and beyond
(03:14) - Origins of The Smart Venture Podcast
(05:50) - Our top 3 dream podcast guests
(08:48) - Angel investing
(20:08) - AI trends and markets
(23:44) - Grace’s venture capital course
(27:42) - Ceremonial final Qs