Be the Quirky Underdog Obsessed About Building the Next New Thing

Adam Draper, Founder and Managing Director at Boost VC, shares stories of his family’s pivotal role in shaping Silicon Valley, from his grandfather’s pioneering work at Sutter Hill Ventures to his father’s global expansion of Draper Associates. Building on that legacy, Adam created Boost VC to back founders tackling endeavors of consequence — companies so bold they’re often dismissed as “too risky” by traditional investors. He explains how pre-seed investing differs from later-stage venture capital and why he loves supporting technically ambitious founders in frontier industries, crypto, space, and deep tech. He also reflects on how curiosity, not consensus, has guided some of Boost VC’s biggest wins. Adam offers candid insights on founder evaluation, the power of weirdness, and how taking risks can often lead to the safest path to freedom.In this episode, you’ll learn:[01:00] The Draper legacy: how one family helped shape venture capital[05:45] From steel to startups: the early days of Silicon Valley[10:45] Adam’s first startup and lessons from failure[13:30] Why Boost VC bets on “endeavors of consequence”[16:00] How Adam thinks about risk, luck, and curiosity in investing[18:30] The weird founder advantage: high agency and obsession as signals[22:45] How Adam evaluates founders beyond the pitch deck[27:00] Rethinking risk: why the boldest path can be the safestThe nonprofit Adam supports: The Ocean CleanupAbout Adam DraperAdam Draper is the Founder and Managing Director of Boost VC, a pre-seed venture firm in Silicon Valley that invests in founders building the future—across crypto, space, deep tech, and frontier science. A fourth-generation entrepreneur and third-generation venture capitalist, Adam has backed more than 300 startups including Coinbase, Amplitude, and Radiant Nuclear. Known for his enthusiasm for “weird ideas,” Adam is passionate about helping founders take bold risks and build enduring companies.  About Boost VCBoost VC is a Silicon Valley-based pre-seed venture capital firm dedicated to supporting founders building transformative technologies in crypto, deep tech, and frontier industries. Founded in 2012, Boost VC has invested in over 400 companies worldwide. The firm averages roughly one deal per week and deploys around $500 K in its lead pre-seed rounds, along with $50 K fellowship checks for emerging founders.Subscribe to our podcast and stay tuned for our next episode.

Jacques Benkoski, General Partner at US Venture Partners, shares lessons from decades of experience as an operator, CEO, and VC. He challenges common startup myths and offers a framework for market entry that emphasizes strategy over luck. Jacques explains why focus—not speed—is the key to building category leadership, and why the venture ecosystem has become noisier, faster, and harder to navigate. He also opens up about the psychological toll of startup leadership and why founders need thought partners, not just capital.In this episode, you’ll learn:[01:00] From Belgium to Israel to Silicon Valley: Jacques’ global path into tech and AI[05:20] “This time it’s different” is rarely true—how founders should think about hype cycles[11:00] Why more capital doesn’t mean an easier path for founders[13:30] The venture industry is now a volume business—but founders need depth, not scale[15:00] What founders get wrong about market entry—and why randomness is the enemy[17:30] Focused beats first: how Medigate won in cybersecurity by narrowing in on medical devices[30:00] The importance of reflection, walking without your phone, and finding a mentor[37:00] Jacques' nonprofit passion: creating dialogue between communities in conflictThe nonprofit organization Jacques is passionate about: TechnionAbout Jacques BenkoskiJacques Benkoski is a General Partner at US Venture Partners (USVP), where he invests in enterprise software, AI, and cybersecurity startups. He has over 20 years of experience as a VC, following a successful career as a startup CEO and tech executive. Jacques is also the author of Market Entry Strategy, a hands-on guide for founders navigating early customer acquisition. A passionate advocate for founder wellbeing and long-term thinking, Jacques mentors entrepreneurs around the world.About U.S. Venture PartnersU.S. Venture Partners (USVP) is a leading Silicon Valley venture capital firm with a strong focus on early-stage companies in enterprise software, cybersecurity, and healthcare. With more than $4 billion raised since its founding in 1981, USVP has backed over 500 companies including Box, Guidewire, Trusteer, and Medigate. The firm brings decades of operational expertise and deep sector insight to help founders scale with clarity and discipline.Subscribe to our podcast and stay tuned for our next episode.

Dave McClure, founder of Practical Venture Capital and co-founder of 500 Startups, dives deep into the growing role of secondaries in venture capital. Dave explains how today’s longer startup cycles and liquidity droughts have created opportunities (and confusion) around secondary markets. He breaks down what secondaries actually are, how Practical VC operates, and key trends shaking up the system. With his trademark candor, Dave also shares hard truths for both founders and VCs navigating this next chapter of private markets.In this episode, you’ll learn:[03:55] Dave’s journey to becoming an investor[06:30] The early evolution of accelerators and why “lots of little bets” took off[09:50] How cloud, open source, and low CAC changed the startup funding game[12:49] Why startup liquidity timelines have doubled—and what that means for founders and LPs[14:56] What secondaries really are (hint: not just one thing)[19:31] Does venture’s illiquidity attract the right kind of investors—or just the most patient?[22:06] The discipline of public markets vs. the opacity of private ones[26:37] What Practical VC looks for in a secondary opportunity (and the $50M–$100M revenue rule)[29:14] How Dave screens funds and companies for possible exits[33:37] What’s exciting (and worrying) about secondaries, stablecoins, and emerging marketsThe nonprofit organization Dave is passionate about: New StoryAbout Dave McClureDave McClure is the founder of Practical Venture Capital, a firm focused on liquidity through venture secondaries. Previously, he co-founded 500 Startups, one of the world’s most active early-stage venture funds. A PayPal alumni and self-described nerd turned investor, Dave has worked across engineering, marketing, and venture roles, investing in hundreds of startups globally. He’s known for his honest insights and bold bets on opportunities before they’re ‘cool’.About Practical Venture CapitalPractical Venture Capital is a Silicon Valley-based VC secondary firm providing liquidity to GPs, LPs, and founders through targeted secondary investments. Specializing in fund-level and company-level secondaries, Practical VC aims to shorten the venture capital time horizon by backing mature, revenue-generating companies with clear exit paths. The firm focuses on portfolios nearing liquidity and brings a flexible, creative approach to valuation, pricing, and structure.Subscribe to our podcast and stay tuned for our next episode.

Nadav Eylath, founder and managing partner of at.inc, shares his philosophy of early-stage investing rooted in trust, long-term thinking, and technical rigor. Nadav talks about backing founders at the very inception of their startup journey—sometimes even before they’ve left their jobs. He explains how asking questions like “What kind of company will this be in 30 years?” leads to deeper conviction and better partnerships. Nadav also shares his views on why venture capital needs to evolve and how a flexible, founder-first approach can reshape the industry.In this episode, you’ll learn:[01:49] From building treehouses to model airplanes: Nadav’s early love for tech and tinkering[03:26] How informal advising turned into full-time investing[04:57] The meaning behind the name at.inc and how it reflects the firm’s thesis[10:01] “What kind of company will this be in 30 years?”—the power of visionary questions[13:30] Building conviction: fast no’s, thoughtful yes’s[15:51] How early-stage founders can build a relationship with Nadav[20:14] Why Nadav says no: timing and fit[24:07] How venture capital should evolve to serve today’s foundersThe nonprofit organization Nadav is passionate about: Tel Aviv UniversityAbout Nadav EylathNadav Eylath is the founder and managing partner of at.inc, a venture capital firm that invests at the very inception of startups. With a background in data science, marketing, and company-building, Nadav brings an operator’s empathy and a long-term investor’s lens to early-stage ventures. His career spans roles at startups acquired by companies like Intuit, as well as over a decade of deliberate, hands-on venture investing. Nadav’s approach is grounded in trust, curiosity, and a passion for helping founders bring technically ambitious and globally relevant ideas to life.About at.incat.inc—short for “at incorporation or at inception”—is a Silicon Valley-based venture capital firm that backs startups from day zero. The firm invests in deeply technical companies with global potential, often writing the first check when founders are just forming their ideas. Generalist by design, at.inc partners with entrepreneurs across sectors, emphasizing long-term vision, high trust, and a hands-on approach. With a focused investment pace and founder-first philosophy, at.inc supports startups throughout their full journey, from inception to global scale.Subscribe to our podcast and stay tuned for our next episode.

Tomoko Ishikura, Managing Partner at Kicker Ventures, shares her unique perspective on investing in the future of healthcare. She talks about building a venture firm rooted in empathy, humility, and measurable impact. Tomoko explains how Kicker Ventures seeks science-backed innovations that move the heart, not just the market, and why strong communities are vital for startup success. She offers candid advice for founders on articulating impact, leaning into community support, and navigating a healthcare landscape that's increasingly collaborative.In this episode, you’ll learn:[02:00] Why Silicon Valley’s "uncertainty and possibility" drew Tomoko from Japan[04:06] Venture capital as a humble act of early belief—and why VCs are deeply interdependent[06:46] Kicker Ventures' mission to create a happier and healthier world through science-backed innovation[12:31] What founders must do in the first meeting to excite impact-driven investors[19:19] Why founders should build strong communities early and ask for help[26:00] Tomoko’s call to eliminate barriers to global innovation and unlock hidden talent worldwideThe non-profit organization Tomoko is passionate about: Kadampa Meditation Center SFAbout Tomoko IshikuraTomoko Ishikura is the Managing Partner at Kicker Ventures, where she leads investments in science-backed innovations shaping the future of healthcare. Originally trained as a pharmacist and molecular biologist, Tomoko transitioned into business development, consulting, and now venture capital. Drawing from her global experience across Japan and Silicon Valley, Tomoko brings a distinctive focus on empathy, impact, and community-driven success to the startup ecosystem.About Kicker VenturesKicker Ventures is a San Francisco-based venture capital firm investing in transformative solutions for the future of healthcare. Kicker backs science-backed innovations that foster happiness, empower individuals, amplify the work of health professionals and researchers, and create meaningful human connections. With a deep commitment to measurable impact, Kicker Ventures partners with visionary founders reimagining health and wellbeing for future generations.Subscribe to our podcast and stay tuned for our next episode.

Dave Anderson, founding general partner at Beat Ventures, discusses his approach to investing in tech startups targeting overlooked legacy industries. He highlights the role of AI in revolutionizing these industries, giving examples of predictive AI application in meat processing and generative AI in finance. Dave stresses the importance of building Silicon Valley networks for funding and hiring while maintaining close customer relationships for execution. Drawing from his unconventional journey into venture capital, he calls for more diversity in the industry to open up opportunities for both founders and investors.In this episode, you’ll learn:[04:40] Challenges legacy industries face in adopting new technology[09:15] Beat Ventures’ focus on niche markets with high growth potential[14:22] The importance of networking in Silicon Valley and proximity to customers[19:08] How democratized technology is fostering diverse founders and investors[21:47] Notable AI innovations transforming legacy industriesThe non-profit organization Dave is passionate about: San Francisco School BoardAbout Dave AndersonDave Anderson is a Founding Partner and General Partner at Beat Ventures. Dave previously served as an Associate at Toyota AI Ventures. Prior to that, he co-founded Bamboo Detroit, the city’s first and largest co-working space for entrepreneurs, and was the director of venture services at NextEnergy, an early-stage technology incubator. An electrical engineer with experience in advanced battery systems, Dave worked with Bosch Battery Systems and General Dynamics Land Systems. He’s recognized as one of Crain Detroit Business’s 20 in their 20s and featured by Huffington Post and ABC’s 20/20. He holds an electrical engineering degree from the University of Michigan and an MBA from Harvard Business School, where he helped launch HBS Accelerate.About Beat VenturesBeat Ventures is a San Francisco-based VC firm investing in AI-driven companies that enhance human performance in overlooked legacy industries. Focused on pre-seed and seed stages, Beat Ventures supports startups using applied AI to complement human ingenuity, rather than replace it. The firm believes the future's most impactful companies will blend technology and human creativity to advance business and society. Its portfolio includes Volur, Stack AI, Truewind, Bitpart AI, Treehouse, Fishtail, Theo AI, Bolo AI, Poka Labs, Safe, Dropverse, and Clockwork.Subscribe to our podcast and stay tuned for our next episode.

Yiğit Ihlamur, co-founder and general partner at Vela Partners, shares his unique venture capital approach, which combines data analysis with personal connections to identify exceptional founders. At Vela Partners, an algorithmic scan of companies helps narrow down investment choices, but final decisions hinge on assessing founder resilience and motivation during meetings. Yiğit explains that, typically, he has already decided to invest by the time he meets a founder; the meeting confirms his conviction. He also discusses AI’s role in shaping the future of productivity tools and offers valuable advice to founders on preparation and authenticity when seeking investment.In this episode, you’ll learn:[02:06] Yiğit's journey from Google to venture capital, and his unique approach to combining engineering and venture investing.[06:27] How Vela Partners integrates artificial intelligence and quant-driven algorithms to identify high-potential startups[10:21] The significance of a balanced quantitative and qualitative assessment in VC investing[12:41] How AI is enabling the next generation of productivity tools[19:08] Articulate your personal story, intrinsic motivation, and ability to articulate your commitment to solving a particular problem.[24:07] What should startups do to attract algorithm-driven funds like Vela Partners? [27:02] Slow decision-making pace in VC is a problemThe nonprofit organizations Yiğit is passionate about: American College Institute (ACI) in TurkeyAbout Yiğit IhlamurYiğit Ihlamur is a co-founder, general partner, and Chief Technology Officer at Vela Partners, a venture capital firm specializing in AI and product-led solutions. Prior to Vela, Yiğit had an impactful career at Google, where he led initiatives for Gmail, Chrome, and Google Workspace, focusing on product-led growth strategies such as self-service signups, activation, and pricing flows. Starting in Google's European headquarters, he initially worked on technical support for IT admins and created productivity tools for internal teams. Yiğit is passionate about advancing human productivity through technology. Outside his professional pursuits, he enjoys kitesurfing, skiing, running, and spending time with his family.About Vela PartnersVela Partners is a Silicon Valley-based venture capital firm specializing in product-led, AI-native startups from inception to Series A. Acting as an "AI startup investing in other AI startups," Vela leverages its proprietary AI to guide investment decisions and enhance its own returns. The firm’s investor-focused tools drive its fund’s performance, while self-service tools for entrepreneurs expand Vela’s brand and distribution channels. Its portfolio includes innovative companies like Vieu, Cartken, Goooods, Nominal, LeakSignal, Base Operations, Cerby, Lightup, Vartana, and Axiom Cloud, among others.Subscribe to our podcast and stay tuned for our next episode.

Lochan Alagh, co-founder of VC Nest, shares her journey from India to Silicon Valley, her work with nonprofits, and her transition into entrepreneurship and venture capital. She explains how VC Nest is addressing gaps in the VC ecosystem by supporting emerging fund managers through collaboration, networking, education, and thought leadership. Lochan emphasizes the need to prioritize founder support over just maximizing returns, fostering a healthier venture capital landscape.In this episode, you’ll learn:[1:51] Lochan’s inspiring journey from India to Silicon Valley[9:19] How venture capital drives innovation[12:19] Key challenges for emerging fund managers: fundraising, deal sourcing, and increasing competition[17:56] The pillars of VC Nest: focused events, curated VC-startup mixers, educational series, and thought leadership[22:50] Emerging fund managers are identifying future unicorns but still struggle with institutional backing (TechCrunch: 30 out of 34 unicorns were funded by emerging managers).The nonprofit organizations Lochan is passionate about: IIT Bay Area Alumni Association, Overseas Volunteer for a Better India (OVBI)About Lochan AlaghLochan Alagh is the co-founder and managing partner at VC Nest, a platform dedicated to supporting emerging venture capital fund managers and innovative startups. Before VC Nest, Lochan served as Executive Director at FalconX, where she fostered global innovation by forging strategic partnerships with accelerators and helping B2B startups establish a presence in Silicon Valley. She is also the Vice President of the IIT Roorkee Alumni Association (Bay Area Chapter), where she focuses on strengthening the alumni community. Previously, she led business strategy and operations at Cloud Harmonics, a rapidly growing startup, until its acquisition by Ingram Micro. Passionate about community service, Lochan is involved with nonprofits such as Overseas Volunteer for a Better India, working on water conservation initiatives, and New Leaders Council, which trains young progressives to become civic leaders. Additionally, she serves as a board member and secretary for the IIT Bay Area Alumni Association (2022-2024).About VC NestVC Nest is a Silicon Valley-based platform designed to empower emerging venture capital fund managers and foster the growth of the VC-startup ecosystem. It offers a range of resources, including networking opportunities, educational events, and fundraising support to help fund managers thrive. With a focus on collaboration and knowledge sharing, VC Nest provides fund managers with insider strategies on fundraising, access to Fund of Funds, and connections with fellow VCs. Additionally, it offers technology infrastructure, portfolio startup workstations, and actionable insights to drive the growth and success of both funds and startups.Subscribe to our podcast and stay tuned for our next episode.

Shreesha Ramdas, a successful serial entrepreneur and angel investor, shares his investment approach, which focuses on the individual stories of entrepreneurs rather than just their business ideas. He discusses the changing face of entrepreneurship in India and highlights the significance of community for founders through the story of how Funda, a thriving community of founders, investors, and operators, came to life.In this episode, you’ll learn:[2:17] “Silicon Valley—what I call Disneyland for tech—completely transformed my mindset.” - Shreesha Ramdas [5:36] New challenges for Indian entrepreneurs building global solutions[13:36] Founder stories matter[19:30] Funda: Building a strong community where founders can learn from each otherThe community activity Shreesha is passionate about: FundaAbout Shreesha RamdasShreesha Ramdas is a seasoned entrepreneur with a proven track record of launching and scaling products in highly competitive markets. He is the CEO and Founder of Lumber, a workforce management platform tailored for the construction industry. Previously, Shreesha was the CEO and Co-Founder of Strikedeck, a customer success automation company that was acquired by Medallia. Before Strikedeck, he served as GM of the Marketing Cloud at CallidusCloud and Co-Founder of LeadFormix, which was acquired by CallidusCloud. Shreesha also held leadership roles at Yodlee, OuterJoin, Catalytic Software, MW2 Consulting, and Tata. In addition to his entrepreneurial ventures, he actively invests in and advises several growth companies, including Workato, Enact, RevvSales, and others.Subscribe to our podcast and stay tuned for our next episode.

Rajan Maruthavanan, Cofounder and Managing Partner at Upekkha, shares deep insights into the dynamics of building B2B startups from India for global markets, particularly in the US. He discusses the strengths and challenges of Indian founders, such as thriving in vertical, niche markets versus struggling with infrastructure and dev tools for global adoption. Rajan emphasizes the importance of founders learning how to take advice and shares his thoughts on the key skills needed for founder success.In this episode, you’ll learn:[3:57] Building a new type of VC firm: The Upekkha story[7:36] Why Indian startups struggle to break into the US market[14:43] The Power of annual contract value (ACV): How ACV shapes startup strategy[19:03] The vertical advantage: Why Indian founders succeed in niche Markets[22:03] How biases and bad advice can trap founders into their biggest pitfalls[28:07] Changing the VC game by improving founder success ratesThe nonprofit organization Rajan is passionate about: Sitare FoundationAbout Rajan MaruthavananRajan Maruthavanan is the Cofounder and Managing Partner at Upekkha, with extensive expertise in guiding early-stage startups through their critical zero-to-one phase to achieve product-market fit. At Upekkha, he has made over 120 pre-seed investments in SaaS startups and assisted numerous founders with M&A activities in DeepTech and B2B SaaS over the past eight years. Previously, Rajan was an Operator and Head of Product for QuickBooks Global at Intuit, where he managed the India GST strategy and led iCombinator, Intuit’s internal accelerator. He also organized two notable conferences: SaaSx in Chennai (2014-2016) and StartupBridgeIndia at Stanford (2016-2019). Earlier in his career, he co-founded and served as CTO of a computer vision startup, developing a SIFT vector-based visual search for Nokia phones.About UpekkhaUpekkha, established in 2017, is an AI SaaS accelerator dedicated to helping Indian founders create global software brands. Currently in its 13th cohort, Upekkha has collaborated with over 165 startups and cultivated a network of more than 300 SaaS entrepreneurs. The firm has a diverse portfolio including companies like iMocha, Almabase, Kloudle, and Cloudbankin. Notably, about 25% of its startups hail from tier-II cities, such as Pune, Kochi, Bhopal, Chandigarh, Raipur, Vadodara, Jabalpur, Warangal, Coimbatore, and Trichy.Subscribe to our podcast and stay tuned for our next episode.