New to Venture

“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 QsSubscribe on YoutubeFollow on SpotifyFollow on Apple PodcastsFollow Taiki on LinkedIn

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/ggOlgpdXwNcjgrCraFsPMy 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

Didn’t make the Forbes 30 list this year?  Learn from a previous Forbes 30 under 30 Venture Capital Standout on Ep 030 of “New to Venture” and maybe next year will be the year! It was such an honor to have Paige Finn Doherty, founding partner of Behind Genius Ventures on the show. Paige is one of the most interesting people I’ve met. From being an author, podcaster, music festival VIP host, and of course a VC fund manager, we break it all down in this episode for the ages!  Key Takeaways: 1️⃣ In a world of AI tools, genuine personalized creativity stands out. Templative cold emails just don’t work the same. Get thoughtful, creative, and scrappy!  2️⃣ VCs are often judged on their access to good deals and their taste. If you want to build a brand from scratch on LinkedIn or X, aim to showcase those traits.  3️⃣ If you want to have a bias towards action, reduce friction in your processes as much as possible. Minimizing the effort and energy to start a task makes it much easier to complete. Timestamps: (00:00) - Introductions (02:18) - The Forbes 30 experience (08:03) - Paige’s college essay  (09:50) - Paige’s favorite podcast episode (11:42) - Odd jobs (13:40) - Sharing information in-person and online (19:59) - From syndicate to fund (23:14) - The vision for Behind Genius Ventures (27:38) - Growing the BGV team (31:09) - Paige’s favorite parts of the job (32:39) - Coming up with Behind Genius Ventures (33:51) - Ceremonial final Qs

What goes into creating a VC firm?  As an aspiring fund manager, this conversation was exactly what I needed! I sat down with Manish Patel, founder of Nava Ventures to take a walk down memory lane. From working with Google’s exec team (including Larry Page), teaching at Stanford University, and building Nava Ventures, Ep 029 is packed with great stories and even better lessons. Manish is incredibly sharp, thoughtful, humble, and passionate and it shines through in this episode. Tune in! Key Takeaways: 1️⃣ Find ways to manufacture luck. This doesn’t mean “get lucky” it means be prepared and ready to take the leap when the time comes! 2️⃣ Vulnerability goes a long way. It's hard to admit mistakes especially in the world of social media where everyone is perfect all the time. 3️⃣ Aim to have a board of mentors/advisors. It’s important to have people that you can have open and honest conversations with. Helpful tip: Make it interesting for your advisors and mentors by giving them a reason to be along for your journey. Both parties will get a lot more out of it 🙂 4️⃣ To create a multi-billion dollar company, you need to have the right foundation. Are you built on a house of cards? Or a stable platform? To reach rarified air, you need to be built on a solid foundation. Timestamps: (00:00) - Introductions (02:14) - Teaching at Stanford University (11:03) - Manish’s learnings from Google (15:54) - Becoming the Accidental VC (19:33) - Transition into VC (23:31) - Creating Nava Ventures (31:12) - Manish’s vision for the firm (33:58) - Traits of a Nava hire (38:34) - Highlights and lowlights (42:48) - Ceremonial final Qs

Here is some advice from one of the best operators turned VC! 🔧👩🏼‍💻💸 I had a blast sitting down with Lucy Deland, General Partner at Inspired Capital. As a NYC truther, she has seen the city blossom into the exciting startup land that it is today. Episode 028 of New to Venture is packed with great stories from creating the legendary Paperless Post to being in the same class as Mark Zuckerberg at Harvard! If you want to feel “inspired” make sure you tune in! Key Takeaways: 1️⃣  If you work in startups and VC, you don’t get the privilege of feeling sorry for yourself. Everyone knows that investing, building, and growing world-changing companies is a hard job. But It's a job you chose! There is no easy road to creating huge outcomes :) 2️⃣ The best operators can unlock other people’s superpowers! They put people in the best positions to make them over-deliver. They can create teams where people feel comfortable to take risks and big swings.  3️⃣  Great relationships stem from a combination of vulnerability and honesty. Who are the people you can be vulnerable with? Who are the people you can be honest with? Do they feel the same about you? 4️⃣  Great VCs can turn curiosity into intelligence quickly. They are quick to get up to speed on a given market or industry. Aim to practice that skill. 5️⃣  In startup land, there are many roles where you should be just looking to hire a super talented human. The role will change many times as the company grows. The more talented human is going to grow with you and point out areas of improvement. Timestamps: (00:00) - Introductions (02:06) - NYC startup landscape evolution (05:22) - Going to Harvard with Mark Zuckerberg (08:14) - Keeping up with trends (12:26) - Paperless Post war stories (16:07) - Founder to VC dynamics (18:58) - Good vs the best operators (23:24) - Inspired Capital (26:14) - Lucy’s favorite parts of the job (29:19) - Finding your people (31:14) - What makes an “Inspired” team member (34:09) - What makes an “Inspired” deal (36:30) - Highlights and lowlights  (38:35) - Ceremonial final Qs 

If people want to regulate you, you’re the real deal! 🧑‍⚖️🏛⚖️ With every large innovative company, regulation comes knocking. Think Coinbase, Fanduel, Bird Scooters, and Lemonade. The biggest companies of this generation all faced intense regulatory scrutiny. That's where Tusk Venture Partners comes in! On episode 027 of New to Venture, I sat down with Jordan Nof, Co-founder & General Partner at Tusk Venture Partners to talk about all things VC. This episode is chock-full of helpful tips, valuable lessons, and great stories! Key Takeaways: 1️⃣ When going to a VC or Tech conference, have a goal in mind! It’s a special opportunity to be around so many talented and relevant people all in one space. Strategize how to make the most of your time there. 2️⃣ Regulation always lags innovation. If you invest in a company that becomes relevant, there will be some form of regulatory scrutiny.  3️⃣  As a fund manager, your job is to stick to the strategy that you laid out to your LPs. LPs are filling out an early stage asset allocation hole when they give money to VC firms. LPs aren’t looking to invest in early stage fund managers who are going to take a bunch of growth stage swings! 4️⃣  Some people aren’t meant to work for large corporations. If you look at the founder world, their risk/reward profile is almost comically unfavorable, but the math isn’t the same when you have the desire to build and create. 5️⃣ If you are in a VC interview, make it crystal clear that you are BOUGHT IN to the firm’s investing strategy. You should be excited to put their strategy to work! 6️⃣  When a VC fund announces their first or final close, it may be an indication that they are hiring. Be on the lookout for these announcements and prepare accordingly.  7️⃣​​ Actively poke holes in your own investment strategy. A good VC investor is constantly rebuilding, rethinking, and reinventing their views on the future. Be aware of your biases and don’t rely on pattern recognition. Timestamps: (00:00) - Introductions (01:56) - Being on TV! (04:59) - VC conferences (11:00) - Jordan’s pivotal career moments  (14:30) - The origins of Tusk Venture Partners (18:55) - GP and LP interactions (24:38) - Being ready to start a firm (27:18) - Recruiting and hiring (31:46) - Understanding Tusk’s thesis (35:56) - Highlights and lowlights (42:55) - Ceremonial final Qs

Don’t be a know-it-all, be a learn-it-all! 🧠📖 Katie Jacobs Stanton is one of the most amazing people I’ve spoken to. I’ve learned so much about venture and beyond from this one conversation and I hope you do too. I left it feeling inspired, introspective, and hopeful! From being an early employee at Yahoo, Google and Twitter, working at the White House, to running Moxxie Ventures, we break it all down on episode 026 of “New to Venture”! If you want to feel inspired about a career in tech and VC, tune in. Key Takeaways: 1️⃣ Prioritization of time becomes crucial as you get older and shoulder more responsibilities. You should be constantly asking yourself, “How can I best spend the time I have to do important things that move the needle?!” 2️⃣ Think of life as a co-opetition not a competition! Don’t focus on competing against the best in industry, focus on learning from them.  3️⃣ Choose your networks carefully. Being an early employee at the PayPals, Googles, and Stripes of the world is an amazing thing. Alumni of those companies go off and change the world. Aim to be in those circles.  4️⃣ Once a relationship feels transactional, both parties know it.  5️⃣ Follow your energy instead of “passion.” Move towards the people, ideas and topics that give you energy, not drain it. 6️⃣ Be slow to hire, fast to fire. Even though you might need extra hands on deck at the moment, in the long run it’s way worse to hire the wrong person. Timestamps: (00:00) - Introductions (02:31) - Katie rocking out on the bass guitar (04:58) - Katie’s massive road trip (09:24) - Shaking things up (12:15) - Best practices for high achievers (16:10) - It’s all about the people (22:25) - Katie’s most transformative moments (25:56) - How pivotal life moments change investing strategy  (28:55) - Hiring and building a firm (32:37) - Finding greatness (37:21) - Where “Moxxie” comes from (40:13) - The difference between a good investor and a good GP (43:14) - Highlights and lowlights (48:17) - Ceremonial final Qs 

This is the story of the ultimate finance resume! 💰💼📈​​ From Harvard to Investment Banking at Goldman Sachs to investing at a PE Megafund to becoming a founding investor for Softbank and then creating a VC firm, Kevin Jiang, GP at Mangusta Capital has accumulated top tier finance experiences like trading cards. In episode 025 of “New to Venture”, we dive deep into his experiences working with some of the most storied brands and talented individuals in high finance. If you’re looking to take your game to the next level, give this episode a listen! Key Takeaways: 1️⃣ Working hard and putting in the hours are table stakes. What makes people stand out are communication skills. Good communicators are heard more clearly, more often, more loudly and can move the needle. 2️⃣ Hiring is one of the hardest things to do. Early on, having the right people on board will change the trajectory of your business. Find the people that aren’t afraid to step above or below their job description or their “weight class.”  3️⃣ When you are looking for a long term hire, fit matters. Trial periods where you can see how they work, gauge cultural fit, and answer any unknowns can be extremely helpful. It's a technique that larger companies can’t implement, but smaller companies may be able to, so use that to your advantage. 4️⃣ Expand your network wide and deep. VC relationships are everything. Your future self will thank you!  Timestamps: (00:00) - Introductions (02:08) - Investing in yourself (05:05) - Pulling all nighters (10:39) - Best practices to stand out in high-finance (14:18) - What “Mangusta” means (16:55) - Firm origin stories (21:23) - What Kevin looks for in founders (23:01) - Kevin’s interest in Vertical AI (26:37) - Electric boat sponsorship? (29:46) - What Kevin looks for in a new hire (36:40) - Highlights and lowlights (43:22) - Ceremonial Final Qs

This is what you learn from talking to the hyper-elite! 🤯 From interviewing the all-time greats like Stephen Curry, Will Smith, and Ray Dalio to leading brand and content strategy for a top VC firm, Melody has done it all! I sat down with Melody Hahm, the Director of Platform & Community at Harlem Capital to take a walk down memory lane. In this episode, Melody shares many important life lessons and the secrets to building a great brand in venture capital!  Key Takeaways: 1️⃣ Don’t be a fangirl/boy. At the end of the day, everyone is a human being. Pedestalizing others doesn’t serve you. In fact, it hinders you from making a real connection with the person you look up to. Find some common ground and be genuine!  2️⃣ The best of the best have an unwavering belief in themselves. Even if they don’t succeed, they will always get back up and maintain a relentless mentality that they can do it! Even if hundreds of people hype you up, what really matters is that you believe in yourself.  3️⃣ High level communication starts with asking good questions. A good question isn’t one that stumps them or forces them to think for a long time. A good question is one that yields a response that is 30% uncomfortable and 70% excitement to tell a story.  4️⃣ Storytelling is such an important skill in venture and beyond. The ability to tell a compelling story about your journey and your mission goes a long way. It gives potential advisors, mentors, and investors a reason to take a shot on you. 5️⃣ Not all VC firms need strong altruistic values. Ultimately, venture capital is a vehicle to drive returns for LPs. It is more disingenuous to virtue signal than to be honest about your firm’s goals and mission. Be okay with what you are!  Timestamps: (00:00) - Introductions (02:49) - The Unforgettable Gala (06:04) - Being around extremely successful people (07:57) - The difference between the greats and the best (12:21) - Best practices for public speaking (17:28) - Melody’s most memorable conversations on TV (23:08) - Similarities between entertainment and VC (26:11) - Reputation and storytelling (30:36) - Creating and instilling values (34:51) - Balancing VC returns and a diversity mission (39:37) - Ceremonial Final Qs

Venture capital and ROI are inextricably linked. But what about ROR? 🤝 This was one of my favorite episodes to record so far. I sat down with Heston Berkman, Founder and Partner of Banter Capital to go over his many learnings over the past decade. Episode 023 of “New to Venture” is an absolute cheat code for those starting in VC. From the importance of relationships, to building a VC firm this episode has it all!  Key Takeaways: 1️⃣ Your founder and VC circles change with time. You need to constantly refresh your networks, be open-minded, and not lean on pattern recognition. 2️⃣ It's okay to mess up, especially early in your VC career! You’re going to incorrectly prioritize your time. You're going to meet people who you think are legitimate, but aren’t. Your efforts may seem unproductive now, but VC is a long game. Your efforts just haven’t been productive YET.  3️⃣ VC is an ROR (Return on Relationships) business. Sure, you can focus on ROI (Return on Investment), but relationships hold immeasurable potential. Meet as many people as possible! 4️⃣ Many, if not all VC careers go through a Trough of Disillusionment around 2-4 years in. Competition gets extremely fierce as you are no longer competing against junior folks. Your brain has become wired to be social and hyper-connected. Your early investments start to hit road bumps. By the time you finally figure out the best use of your time and make the right decisions, it’s way harder to find your footing in a traditional role.  5️⃣ Get on the flight! If you’re excited about a founder and you’ve done all the research you possibly could, you better hop on a plane and get to know them in-person. Investing in early-stage founders is like a marriage. Make sure you get along as people, not just business partners.   Timestamps: (00:00) - Introductions (02:04) - Heston’s love for boating (08:00) - Is startup funding seasonal? (10:18) - Heston’s time at First Round Capital (12:23) - VC and founder circles change every 7 years (15:14) - Working with First Round and Dorm Room Fund (17:50) - What Heston looks for in founders (21:23) - Transitioning into full-time venture (25:25) - Best practices for those new to venture (27:31) - Getting operating experience (31:31) - Heston’s first angel check (33:00) - Heston meets an NFL football player (36:25) - Partner track vs. raising your own fund (39:23) - The origins of “Banter” capital (41:23) - What Heston looks for in an investor (44:58) - Ceremonial Final Qs

Video Games Meets Venture Capital?! 🎮 I sat down with my good friend Jonny Zhang, who may have the best job on the planet. Jonny invests in games at the illustrious General Catalyst as well as invests in the brightest student founders as a lead for GC Venture Fellows. Jonny found a way to combine his passion for video games with the world of venture capital. If you’re looking to do the same, make sure you give a listen to episode 022 of “New to Venture”! Key Takeaways: 1️⃣ Find a speaking style that works for you! For the introverts or people that want to break into venture, confident communication is an underrated skill. Take the time to find a voice that feels genuine and complements your energy. 2️⃣ Separate your personal opinions on a market or company from your due diligence. It’s incredibly easy for your personal tastes to bias your investment theses. Take a step back, get a hold of as much data as you can, then build your thesis. 3️⃣ Gaming has become an essential part of our society. Video games create communities, friendships, relationships, hobbies, and play a big role in pop culture. It is an exciting time for the world of gaming with so much room to grow. Timestamps: (00:00) - Introductions! (01:50) - Jonny’s love for Broadway and Common App essay (05:27) - Jonny’s path into venture (09:28) - Harvard Student Agencies + COVID Era (13:42) - How to get better at speaking! (16:54) - Transitioning to investor (20:19) - Intern to full-time (22:56) - Jonny’s outlook on games (26:17) - The reputation of games investing  (30:42) - What makes a gaming startup VC backable? (33:46) - The future of gaming (35:54) - Investing in student founders with GC Fellows (41:14) - A day in the life (42:48) - Ceremonial final Qs

This is the secret to making a top 1% podcast. Be stubborn.  Episode 21 of “New to Venture” marks a special milestone in my life. “If you make it to episode 21, you are in the top 1% of podcasters. Survival is more important than skill.” This was my north star for the past year and in celebration of achieving it, this episode is going to be different. No all-star VC guest. No questions asked. Just you and me. I talk about my learnings in VC so far, my learnings from creating the podcast, and general life learnings to close it all out.  To every guest that has joined me on the pod so far, thank you for taking a shot on me. I’m truly forever indebted. I can’t wait to make you all proud and finally duke it out in the same arena. Now, on to episode 52 🫡 Key Takeaways: 1️⃣ Posting is really hard and scary, especially on LinkedIn. Your high school friends, work friends, college friends, and sometimes even family members will all see your content. The thought of them thinking that you are “cringe” is extremely paralyzing. Remember that no one actually cares that much and your real friends will show love and support! 2️⃣ A good VC is always thinking of others. Being selfless and going the extra mile for your network makes you better at your job AND makes it 10x easier down the line. 3️⃣ Asking good questions and smiling are by far the two things that have gotten me the furthest in life. A good question is one that opens the door to stories and emotions, not one that stumps people. Smiling indicates warmth and that you are excited to be there. A conversation filled with emotions, stories and smiles is almost never a bad one 🙂 For more key takeaways, listen to Episode 21 of “New to Venture”! Timestamps: 00:00 - Introduction! (Who am I?) 15:36 - VC Takeaways 20:44 - Podcast Takeaways 26:46 - General Life takeaways 33:55 - Ceremonial Final Qs

This is the story of one of the great VCs of NYC🗽 I sat down with Brian Smiga, serial entrepreneur and co-founding partner of Alpha Partners, to take a walk down memory lane. From sitting in a hot tub with Marc Benioff to starting a TEDx conference in his town, Ep 020 of “New to Venture” is packed with stories and perspectives from a seasoned entrepreneur and VC. If you want to last a long time in this industry, make sure you give this episode a listen! Key Takeaways: 1️⃣ The VC world runs on karma. Pay it forward. Do good for others and expect nothing in return. Try your best to NOT make things transactional. 2️⃣ Get into the rooms with people smarter than you. Being intentional about the people you surround yourself with will supercharge your growth.  3️⃣ Develop a point of view. Get interested in something. 80% of VCs are specialists. Study up and come prepared with a sophisticated and educated perspective.  4️⃣ Relationships are everything. Seeing your peers grow is fulfilling. When you look back, you’ll remember the people you worked with, not the tasks. Timestamps: (00:00) - Introductions! (02:00) - Jack of All Trades (04:20) - TedxAsburyPark (07:02) - Blackbelt VCs (08:50) - Founder → Investor (12:19) - Alpha Partners Founding Story (15:45) - NYC Tech Ecosystem (19:05) - Traits of a Successful VC (23:34) - Good Karma (24:40) - Where to Find Smart People (30:23) - Highlights and Lowlights (35:01) - Ceremonial Final Qs

How you can become a Venture Capitalist … without ANY money! 🤯 I sat down with Alex Pattis, the King of SPVs and the General Partner of Riverside Ventures, to break down a unique way to invest in your favorite private companies. A normal VC firm pools capital together to create a fund and invests out of that fund. The syndicate system invests in startups on a deal by deal basis! If any of that is confusing to you, and you want to start VC investing without any of your own money, make sure you listen to Ep 019 of “New to Venture”! Key Takeaways: - Provide value first. Try your best to be helpful! Don’t just say it, find ways to do it. Many VCs are ridiculed for saying “Let me know how I can be helpful” but never actually being helpful. Try to not be that person.  - VC funds follow a 2 and 20 structure, meaning that 2% of the fund is given to the firm every year to manage the money and after the firm returns the fund they get to keep 20% of the profits. An SPV structure is similar, but there are 2 main differences. For early stage investments, usually the management fees are nonexistent, a one time fee, or lower than 2%. Second, SPVs don’t have to return an entire fund's worth of capital before they see a dollar of profit, just the initial investment amount.  - Signaling plays a huge role in the world of syndicates. Since a syndicate lead has to raise money from LPs on every deal, good signaling (strong co-investors) garner more interest. - When you’re young, you tend to be aggressive about helping with everything. Ultimately, that's a trap, be realistic with what you can actually provide and over deliver on that thing. Under promise and over deliver. - Staying top of mind is difficult. Some best practices include grabbing in-person coffee, quarterly calls, and posting content. Building an online presence is an underutilized method to staying top of mind! Timestamps: (00:00) - Introductions! (02:06) - Go Arizona Wildcats (04:38) - Sending Cold Emails and Getting Started (06:46) - Providing Value to VCs as a young VC (07:56) - Which VCs to reach out to (10:43) - Building a deal flow engine (15:01) - Origins of Riverside Ventures (17:09) - Institutional VC vs. Syndicate Lead (20:05) - Alex’s Newsletter - Last Money In (22:37) - Syndicate Structure (27:32) - Signaling in SPVs (32:52) - Chasing a Hot Deal (37:20) - Staying Top of Mind (40:27) - Most Helpful Investors by Category (44:06) - Ceremonial Final Qs

Is Imposter Syndrome actually a good thing? I sat down with the amazing Chelsea Zhang, Principal at Equal Ventures to share stories and lessons for the next generation of VCs. Almost every young VC struggles with imposter syndrome, but they’re not alone! This episode is jam-packed with comforting advice, harsh realities, tons of passion and even more honesty. If you’re exploring the VC career path, make sure you listen to episode 018 of “New to Venture”!  Key Takeaways: - Imposter syndrome runs rampant in the VC world. But that’s a good thing! It is a big responsibility to decide who gets money and who doesn’t. It takes a long time to know if you’re good at VC, so having imposter syndrome can keep you in check and indicate that you are actively trying to become a better investor.  - Banking, Consulting and many professional services are very structured. VC is the opposite. The scrappy, quick on their feet, passionate individuals are in a better position to succeed.  - There are so many compounding advantages in venture. Getting in the reps, talking to tons of founders, building genuine connections, creating content, building your brand. These all make you a better investor, but it doesn’t happen overnight. Keep having faith that your efforts will compound and show results down the line! Stay consistent! - Every VC fund has a very specific criteria when they hire. It is not an industry where the “spray and pray” application method works. Understand your best qualities and recruit specifically for VC funds that are looking for your skillset.  - Ramping up for the first time in VC is extremely intense. VC firms expect you to hit the ground running so try your best to “be a VC” before starting at a firm.  - At the entry level, extroverts have an advantage in VC. Having the energy to talk to founders, investors, and industry experts all day can make the job a lot easier.  Timestamps: (00:00) - Introductions! (02:46) - Sports Twitter and Sci-Fi Novels    (07:50) - Chelsea’s Path into Venture (11:48) - Applicable Skills from Consulting to Venture (14:41) - Learning Curve from Consulting to Venture (19:50) - Breaking into VC (24:09) - Imposter Syndrome (27:53) - Building Investment Theses (35:22) - How Your Role Changes with Seniority (41:00) - Highlights in Venture (43:00) - Ceremonial Final Qs

Harvard → Consulting → Growth Equity → Venture?  I sat down with Matt Hawes, an investor at 645 ventures, to talk about all things venture. What is it like to work at a massive firm? How does one build thoughtful investment theses? What does success look like as you rise up the ranks? Find out on Ep 017 of “New to Venture”! Key Takeaways: - Invest with discipline. Macroeconomic trends will change the standard of “a good startup” especially with regards to valuation and multiples. Stay disciplined, invest based on your thesis, not the market.  - Deal flow quantity and deal flow quality have a synergistic relationship especially for young VCs. Quantity is important so you can get the reps and a pulse on the startup ecosystem. At the end of the day though, it’s a quality game. Additionally, having deal flow quantity allows you to elevate your quality bar.  - One of the lowlights of being a VC is when you are deeply excited about a company, but are not able to invest. You’re forced to take a backseat and watch them grow instead of being in the trenches with them. Timestamps: (00:00) - Introductions! (01:40) - How Matt and I Met/Creating Music (05:58) - Matt’s Path to Venture (13:21) - Leaving Consulting for Venture (17:08) - Working for Insight Partners (21:45) - How Success Changes with Seniority/Firm Size (25:16) - Quantity vs. Quality (28:53) - What Attracted Matt to 645 Ventures (31:36) - Differences Working for a Big vs Lean VC Firm (32:43) - Do Founders Treat You Differently at a Big Firm? (35:15) - Matt’s Favorite Moments in VC (37:46) - Building Investment Theses (40:32) - Missing Out on a Company You Love (41:47) - Ceremonial Final Qs

Honesty is the best policy! I sat down with Julia Maltby, the Principal at Flybridge Capital Partners to have an honest conversation about the hardest parts of working in venture, the MBA experience, and building personal conviction. Episode 016 of “New to Venture” is jam packed with valuable lessons for the next generation of VCs and some fantastic stories! Tune in :) Here are some key takeaways from our conversation: - The world will test you with difficult times. Take note of the ones who stick by your side and those who make the extra effort to be there for you.  - Oftentimes, the best performing deals are the most controversial. If everyone thinks it’s a good idea, there may be more competition than you think.  - For MBA programs, you can prioritize social, career, or academics, but it's difficult to do all three well. Go into the program with intentions and goals! - Ultimately, VC is a game of weighing risk. Gather as much information as you possibly can. Make an informed decision. Then be as helpful to that company as you can.  - There will come a time when you do tons of research and diligence on a vertical, market, or company and arrive at a dead end. Although it’s demoralizing, understand all that work will be helpful down the line. Maybe it’s similar to another sector, maybe it helps you get to “no” faster, or maybe a new law passes and flips the entire market on its head. Write down key learnings from your research so you can refer back to it when needed. (00:00) - Introductions! (02:08) - Julia’s VC Tiktok Account (05:48) - Vassar’s Rugby Team (07:30) - Julia’s Path to VC (13:06) - The Wharton MBA Experience (14:28) - Ride-or-Die Friends (16:31) - Work/Life Balance in VC (17:54) - Flybridge, Deco Ventures, and Next Wave Funds (21:58) - Building Personal Conviction (25:00) - The Story of Blumen Systems (Julia’s Investment)  (28:23) - Ceremonial Final Qs

Legendary Football Player 🏈 + Elite Startup Founder🚀 = Top VC Firm!?! Here are some key takeaways from our conversation: - In the world of startups and VC, you’ll be surrounded by people with insane success, track records, seniority, and experience. Regardless, it’s important to follow your gut, advocate for your beliefs, and have confidence in your own abilities! - If you’re starting a career in venture, spend time with as many founders as possible. Founders help shape your investment theses and give you a pulse on the current startup landscape. I sat down with the amazing Michael Ma, Founding Partner of Liquid 2 Ventures. Michael has a resume that would make any techie swoon. From selling his startup to Google, working as a PM, then creating a top VC firm from scratch, Michael really has done it all. Tune in to episode 015 of New to Venture where we dive deep into family expectations, confidence, Michael's crazy journey and beyond! Here are some of Michael’s accomplishments: - Forbes 30 u 30 in VC - Exited Founder of Talkbin (Acq by Google) - MBA from Harvard Business School - Founder of CreatorDAO (Backed by a16z and Initialized) - Business Insider’s Top 100 Seed Investors Timestamps: (00:00) - Introductions! (02:39) - Micheal’s Immigrant Family/Asian Parents (10:34) - Starting Liquid2 Ventures with Joe Montana (14:19) - Why Start Your Own Firm? (19:41) - First Steps to Creating a VC Firm (21:35) - The Y Combinator Founder Experience (23:16) - Confidence and Imposter Syndrome (26:02) - Misses and Mistakes (28:10) - Highlights and Lowlights (30:29) - Ceremonial Final Qs

In the world of VC, people are everything! I sat down with the legendary Lily Lyman, General Partner at Underscore.vc to talk about all things people. How do you pick the right founders? How do you find the right VCs to join your investment team? How do you choose the right business partners? Find out on episode 014 of New to Venture! Here are some key takeaways from our conversation: - “Choose the professor, not the class.” Surround yourself with great managers and people you are excited to learn from. - Attitude, Aptitude, Ability. In that order, focus on sharpening and displaying these attributes. - Prioritization of time is the most difficult aspect of being a VC. Say “yes” often enough to put yourself in the path of serendipity and luck, but also have a hypothesis on which people and which relationships may be the most valuable/helpful. Additionally, saying “no” and setting boundaries on your time commands respect. Timestamps: (00:00) - Introductions! (02:53) - Lily’s Love for Traveling  (05:13) - Startup Similarities Around the World (08:33) - Lily’s Mindset on Prioritizing Your Time (10:38) - Picking the Right Investor/Founder to Partner With (14:01) - What changes as you become more senior in VC? (17:50) - A Day in the Life (20:15) - Lily’s Favorite Part of Venture Capital (24:18) - Building a Venture or a Venture Firm (27:31) - Evaluating Founders with Little Track Record (30:40) - Evaluating Founders vs. Hiring Investors (34:53) - Ceremonial Final Qs

There is SO much more to VC than writing checks❗ In episode 013 of “New to Venture”, I sat down with Katie Mulligan, the Director of Platform at Pillar VC, to go behind-the-scenes of one of the top early stage firms! Platform is the backbone of most VC firms, so I’m excited to give you all an inside look. In this episode, we also share fun stories like my experience interviewing for an internship with Pillar VC and Katie’s time as a TV show host. If you don’t want to be an investor, but still want to work in VC, give this episode a listen! Here are some key takeaways from our conversation: - Platform is a job that requires you to be the ultimate swiss army knife. You need a strong understanding of venture capital, marketing, operations, event planning and general business strategy.  - To be successful in a platform role, learn to comfortably jump from one project to another without losing much speed. - Brand and reputation is all about how people experience working with your company and your team. Building brand is about taking care of the founders you work with, not shouting your company values from the rooftops! Timestamps: (00:00) - Introductions! (01:45) - Katie’s time as a kids TV show personality (07:47) - Katie’s career path to venture (13:30) - Evaluating companies in the early stage vs. late stage (19:56) - What is platform? (23:33) - How the job changes over time (25:55) - Good practices for building platform (31:18) - The most fulfilling parts and the hardest parts of Katie’s job (37:46) - Katie’s favorite Pillar event (41:37) - Building reputation and brand (46:17) - Ceremonial Final Qs

Pro-gamer turned entrepreneur turned VC investor? 🤯 In episode 012 of “New to Venture”, I sat down with a friend and fellow Northeastern Alumni,  Kasey Zhang. Kasey is a VC investor at Audacious Ventures, one of the best up-and-coming early stage VC firms. Kasey has always impressed me with his drive, knowledge, and intelligence. I hope he does the same for you! Listen to two Northeastern Huskies share stories about startups, college, entrepreneurship, and VC recruiting! Here are just a few of his crazy accomplishments: - Founded and sold an Esports startup 🕹️ - Previous Managing Partner at Rough Draft Ventures 💸 - Ex-Professional League of Legends player 👾 - Ex-Director of the Husky Startup Challenge 🚀 Here are some key takeaways from our conversation: - If you’re looking to break into junior VC roles, you have to do more than just schedule coffee chats and send deal flow. Condense your expertise and value-add into two sentences, and use that as the pillar for your application. - VC is fundamentally a sales job! It is hugely relationship driven. Hone your ability to evaluate people just as much as you hone your ability to evaluate startups. - There are only a handful of deals that matter every year. Can you get access to those deals? If not, how can you get access? Answering these questions are key for VCs. (00:00) - Introductions! (01:50) - Building and selling Kasey’s business (10:15) - Highlights and lowlights of entrepreneurship (13:30) - Intersection between classes and real-world business (16:29) - How Kasey evaluates startups (26:19) - Kasey’s path to VC (30:33) - Rough Draft Ventures and young founders (34:40) - Junior VC recruiting and disproportionate representation (43:53) - Ceremonial Final Qs

Learn how this VC is lifting stigmas in frontier wellness!  Misunderstood markets and non-traditional verticals hold so much unrealized value! From breathwork studios, to cannabis tech, to MDMA therapy, most venture capital dollars overlook the massive value in these untapped markets. In episode 011 of “New to Venture”, I sat down with Helene Servillon, Founding Partner at JourneyOne Ventures. We dive deep into the world of misunderstood markets, frontier wellness, and the difficulties of building a VC firm. If you’re looking for new industries to invest in, give this episode a listen! Here are just a few of her crazy accomplishments: - Women Who Empower Innovator Award 💡 - Business Insiders’ Top Global Execs in cannabis 💰 - Marijuana Ventures 40 under 40 🧪 - Guest lecturer and speaker at top MBA programs 🎤 Here are some key takeaways from our conversation: - Being a VC investor and running a VC firm are two completely different jobs that require different skill sets and talents. - Be persistent! You’ll hear many “No’s” in your life, but sometimes those will change to “Yes’s”. - Emerging Fund Managers play the LONG GAME. It takes almost a decade to get results on whether or not you’re good at the job. Startup founders can build the biggest businesses in 10-12 years, but building the best VC firms takes much longer. (00:00) - Introductions! (02:20) - Playing D1 Volleyball! (07:50) - Helene’s career path  (15:19) - Helene’s North Star and “Why” (17:30) - The origins of JourneyOne Ventures (25:49) - Why being a solo GP is so difficult (32:17) - Why Helene loves VC  (38:22) - Diving deep into Frontier Wellness (46:42) - Misunderstood markets outlook (51:30) - Ceremonial Final Qs

So this is venture capital, but even cooler? 🤔 In episode 010 of “New to Venture”, I had the pleasure of speaking to Jane Chen, Principal at Blue 9 Capital. When people think of venture capital investing, they think of the big VC firms like Accel and Sequoia Capital. What people don’t know is that family offices also invest in startups and can perform just as well! VC is already such a secretive industry, but the world of family offices is even more secretive and maybe even more glamorous. Founders have to pitch to VCs, but VCs have to pitch to family offices! Tune in to learn the ins and outs of a top NYC venture capital focused family office! Here are some key takeaways from our conversation: - Family Offices investments tend to lean more towards capital preservation while VC firms look to return their fund with any given investment. This allows for Family Offices to be more fluid and flexible with interesting opportunities. 💡 - Family Offices are generally more low key due to security and safety concerns. For this reason, Family Office circles are tight and referrals go a long way! 🤝 - There is so much money in this world. Families have built massive generational wealth through means besides high finance, technology, and consulting. 💰 (00:00) - Introductions! (03:41) - NY Tech Week and generational wealth (05:18) - Jane’s career path  (08:28) - Transitioning from IB to VC (13:22) - What is a Family Office? (16:15) - Classic Venture Capital vs. Family Office (18:30) - Highlights of working in a Family Office (25:47) - Family Office value-add to founders (30:24) - Complexities of working with families (33:58) - Recruiting in Family Office investing roles (37:15) - The VC learning curve (37:55) - Ceremonial Final Qs

Ready to hear some of the best VC stories? 🤯 This episode of “New to Venture” perfectly encapsulates the very reason I created this podcast. In episode 009, Patrick Chung, General Partner at Xfund, shares some crazy stories from investing in Sam Altman, meeting the Prince of Wales, and seeing a legendary VC investor jump into a pool with a full suit on. Patrick is as sharp as a tack, extremely kind, super fun, and a fantastic role model. I’m so excited to share this with you all!  Here are just a few of his crazy accomplishments: - Obtained a joint JD/MBA from Harvard and MSc from Oxford 📖 - Youngest elected partner at New Enterprise Associates (NEA) 🌱 - Invested in household names like 23andMe, Plaid and more 💸 - Raised over $120M to fund the top university talent 🏫 Timestamps: (00:00) - Introductions! (03:38) - Patrick’s run-in with royalty (10:24) - Origin stories: Harvard JD/MBA → McKinsey → Startups (19:20) - Falling in love with venture (20:48) - Patrick’s first VC investment was to Sam Altman! (26:35) - How Patrick become the youngest partner at NEA (32:09) - The beginnings of Xfund (40:16) - Ceremonial Final Qs

Want to break into venture capital and startups?🦄💸 In episode 008 of “New to Venture”, I had a blast sharing stories with Aidan Kittredge, Program Manager at Techstars. Over the years, Aidan has taught me so much about being an upstanding member of the venture ecosystem and I hope she does the same for you! In this episode, Aidan and I discuss all things VC from the secretive recruiting process, building community, making friends, and sharing general advice. Aidan has some incredibly unique experiences and stories, make sure to tune in! Here are just a few of her crazy accomplishments: - BostInno’s 25 under 25 🤩 - Host of many VC panels and tech events 🥂 - Prev Managing Director of the Rines Angel Investment Fund 🪽 (00:00) - Introductions! (02:06) - Aidan’s middle school clothing non-profit (04:42) - Origin Stories (09:05) - Forbes article about the Rines Fund (12:21) - Aidan’s crazy post-grad path to venture (16:52) - Deep dive into Gutbrain Ventures and PBJ Capital (24:24) - Key learnings from VC career so far (26:41) - Becoming a VC swiss army knife (29:24) - Building community (35:11) - Tips to hosting great events (38:59) - Aidan’s experience with VC recruiting + tips (42:24) - Tips for networking (48:47) - Ceremonial Final Qs

What changes as VCs gain more experience? 🌱📈 In episode 007 of “New to Venture”, I sat down with the amazing Robin Li, Partner at GGV Capital. Robin has cemented herself as a pillar in the VC ecosystem especially within women and AAPI groups. Outside of being an elite investor, Robin puts in a lot of effort to nurture the next generation of VCs and build community. In this episode, Robin’s deep passion for venture shines through as she shares good practices for younger VCs, tips for keeping yourself intellectually honest, and her favorite parts of being a VC! Here are just a few of her crazy accomplishments: - Invested in multiple household names like ByteDance (TikTok), Poshmark, and Peloton🤩 - NVCA’s Rising Star Award Winner in 2018  🚀 - Board member or observer to 20+ companies 🛠️ - Host of Reimagined with Robin 🎙️ - AAPI Founder and Funder community leader 🧧 Timestamps: (00:00) - Introduction to Robin! (01:42) - Robin’s Show: Reimagined with Robin (04:26) - AAPI community and events (07:30) - How traveling helps you be a better VC (10:44) - How VC perspectives change over time (13:35) - Understanding long feedback cycles (14:56) - Good practices for young VCs (17:43) - Being intellectually honest and checking your biases (21:00) - What to look for in founders (27:03) - How a young VC can stand out (28:48) - Exciting moments as a VC investor (30:09) - What Robin loves about VC (32:25) - Ceremonial Final Qs

What’s the difference between great VCs and the best ones? 🔝😎 If you’re going to listen to any episodes of “New to Venture”, make sure you listen to this one. Jason Shuman, General Partner at Primary Venture Partners, keeps it real about the world of VC while providing practical advice to reach the next level. I definitely wish I could listen to this when I started my first VC internship. In this episode, Jason and I dive deep into creating investment theses, standing out as a young investor, and his career highlights! Here are just a few of his crazy accomplishments: - Forbes 30 under 30 🤩 - Venture Capital Journal’s Rising Star in 2020  🚀 - Previous founder and CEO or a lifestyle footwear brand 👞 - Board member or observer to 10+ companies 🛠️ (00:00) - Introduction to Jason Shuman! (02:20) - Jason’s DTC footwear brand (06:57) - Favorite parts of working as a VC (08:48) - Building brand (13:10) - How to avoid groupthink (15:09) - Building investment theses (20:01) - Rising up the ranks (25:10) - How the day-to-day changes over time (30:26) - Winning deals (32:23) - Why VC? (34:38) - Jason’s highlights and best moments (36:31) - Ceremonial Final Qs

What’s the secret to in-person networking? 🤝📈👥 I sat down with a staple of the New York City venture ecosystem and super-connector, Shai Goldman, to talk about the importance of building your network! With 20+ years of experience, Shai has built a reputation in the startup community as a big supporter of founders, doing all that he can to help them reach their next milestone. On this episode of “New to Venture”, Shai shares stories of the early days of his career, compares the startup landscape in the east and west coasts, and gives tips on how to make the most out of a networking event. Here are just a few of his crazy accomplishments: - Over 38k followers on X/Twitter by providing helpful insights 📲 - VC and angel investor in 30+ companies with multiple exits 💸 - Hosted countless tech events and conferences 🎉 - Founding member of the NYC Advisory Board of BUILD 🛠️ Timestamps: (00:00) - Introduction to Shai! (04:28) - Startup ecosystems in the Bay Area vs. NYC (08:45) - How to make the most out of a networking event (13:23) - How tech events have changed over the years (15:42) - Shai’s path to tech (18:11) - Shai’s experience at Silicon Valley Bank (SVB) (23:53) - Good practices for online networking (28:33) - The move to Brex + Key learnings (33:45) - Being an investor at 500 Startups (37:28) - Highlights and lowlights (40:08) - Ceremonial final questions

Where does Venture Capital fit within the finance ecosystem?🏦 On this episode of “New to Venture”, I sat down with Senior Vice President at UBS, Brenda O’Connor Juanas. My mind was absolutely blown when I attended her workshop at TheVentureCity summit earlier this year. You may recognize Brenda from TV as she appears frequently on major news outlets like Fox Business Network, BNN Bloomberg, and CNBC.  Brenda helped me connect the dots between macro-economic factors and how they trickle down to affect the VC space. It was a huge unlock for me and I hope she does the same for you! Here are just a few of her crazy accomplishments: - Countless appearances on cable business news channels 🎬 - Forbes Best-in-State Wealth Advisors🤩 - Forbes Best-in-State Wealth Management Teams👥 - Forbes Best-in-State Women Wealth Advisors👸 - Working Mother Magazine/SHOOK Top Wealth Advisor Moms👩‍👧‍👦 In this episode, we talk about building a personal brand, being on TV, understanding macro-economic factors, and her current market outlook! (00:00) - Introduction to Brenda! (03:17) - What’s it like being on TV? (09:03) - Brenda’s passion for being a financial advisor (11:42) - Where does Venture Capital fit in the financial ecosystem? (14:30) - The biggest risk to founders now: Fixed Income (20:46) - Understanding deal activity and valuations (24:23) - What’s happening today? (30:50) - How to gain knowledge on the financial markets (35:15) - Market Outlook! (37:47) - Ending + Lessons for young professionals

How do you differentiate yourself when applying to roles in Venture Capital? 🗣 On this episode of “New to Venture”, I caught up with one of the rising stars in VC, Jonathan Chang. About a year and a half ago, I remember watching Jonathan’s Tiktoks to prepare for my VC interviews! Jonathan has become a celebrity amongst the aspiring VCs of Gen Z. I can’t think of anyone better to have on my podcast about being new to venture capital! Here are just a few of his crazy accomplishments: - One of the first VC Tiktokers, now with over 11.3k followers 🤳  - Silicon Valley Business Journal’s Inno under 25 🤩 - Hosted countless events with Brex as an XIR 🎉 - Founder of GenZscouts 💫 - Creator of the SF IRL (a newsletter for top tech/startups/VC events in SF) 🎟️ - Angel investor in 10+ startups📈 In this episode, we share stories about VC job recruiting, the power of a strong network, and the important qualities of a young VC! Timestamps: (00:00) - Introduction to Jonathan! (02:15) - The beginnings of the “New to Venture” podcast (05:30) - Startup and VC communities (09:32) - Jonathan’s path to VC (19:09) - Slack communities for aspiring VCs  (20:33) - VC job recruiting (28:21) - Venturecapitalguy TikTok account and GenZscouts (33:30) - Juggling different jobs within the venture ecosystem (37:51) - Building community and hosting events with Brex (44:19) - Ceremonial Ending Questions

Have you ever wanted to create and build a VC firm?🧐 I talked to the wonderful Gisuseppe Stuto about his journey creating 186 Ventures, one of top up-and-coming pre-seed & seed stage VC firms. Giuseppe has been so impactful in the Boston startup ecosystem as well as mentoring the next generation of VCs. It’s such an honor to have him as a guest! Here are just a few of his other crazy accomplishments: - Serial Entrepreneur backed by top VC firms like Flybridge, NEA, and Bessemer 🚀 - Business Insider’s “Most Important VCs in Boston” 😎 - Boston Business Journal’s 40 under 40 🔥 In this episode, we also talk about the role of reputation in VC, highlights and lowlights of being a top CEO, and what it truly means to be founder-first.  Timestamps: (00:00) - Introduction to Giuseppe! (02:08) - Giuseppe’s journey to VC (07:02) - The creation of 186 Ventures (13:03) - Story of raising Fund I (19:17) - Pitching to LPs  (22:54) - Highlights and Lowlights of being a Founder and GP (34:02) - The role of reputation in VC (39:14) - Assessing your investments and VC feedback cycles (43:29) - Why build 186 Ventures in Boston? (47:59) - Ceremonial Ending Questions

I couldn’t have asked for a better first guest than the one and only David Kidder. I remember my dad used to read David's books to me every night before bed, and now he’s a guest on my show. Here are just a few of his crazy accomplishments: - Ernst and Young’s Entrepreneur of the Year in 2008  - Serial Entrepreneur with 3 exits - Co-author of multiple New York Times bestselling series - Angel investor in 70+ startups  In this episode, we talk about the keys to being a successful CEO, what he looks for when he invests in companies, and then we get introspective about career and personal growth.   Timestamps: (00:00) - Introduction to David! (00:48) - Introduction (02:38) - The story of Bionic (15:22) - Highlights and lowlights of being a serial entrepreneur (19:10) - David's investment thought process (29:17) - Building your network and providing value to others (37:24) - Legacy and "The way to Integrity" (43:00) - Words of Wisdom and a State of Being (50:30) - Shout out a VC that you admire! (51:26) - Shout out a startup!