By Gopi Rangan
The podcast currently has 151 episodes available.
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 rates
The nonprofit organization Rajan is passionate about: Sitare Foundation
About Rajan Maruthavanan
Rajan 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 Upekkha
Upekkha, 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.
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Raed Masri and Rama Chakaki, general partners at Transform VC, discuss their unique approach to venture capital, focusing on impact-driven investments and supporting diverse, underrepresented founders. Drawing from their diverse backgrounds as entrepreneurs and investors, they discuss how they evaluate startups, form investment convictions, and challenge traditional industry norms. Raed and Rama also provide practical advice for founders seeking to make the most of their early meetings with venture capitalists.
In this episode, you'll learn:
[3:12] Moving beyond traditional Silicon Valley thinking to embrace global perspectives and diversity.
[7:21] Why Transform VC prioritizes founders who are deeply obsessed with their customers and solving real-world problems.
[11:15] How VCs build conviction through multiple interactions with founders
[17:54] Bridging the gap for underrepresented founders; what the industry can do to better support these entrepreneurs
[22:28] Practical tips for founders to maximize early meetings with investors
[24:41] Measuring impact in startups: Key criteria and questions for founders to consider when demonstrating their social or environmental impact.
The nonprofit organization Rama is passionate about: VIP Fund
About Raed Masri
Raed Masri is the founder and general director at Transform VC. Raed is a seasoned technology entrepreneur turned top-performing venture capitalist. As the founder of Transform VC, a Silicon Valley firm that has backed multiple deep tech startups, including four unicorns, Raed focuses on identifying untapped founders who can achieve transformative impact and exceptional returns. With a track record that includes two companies with 20x outcomes and three failed ventures, he brings a wealth of experience to his role as a hands-on investor. Raed aims to support 1,000 mindful tech founders to each impact a billion lives and make a billion dollars through deep tech for social and climate impact. He holds an Engineering degree from Carleton University and an MBA from Cornell University.
About Rama Chakaki
Rama Chakaki is a general partner at Transform VC. Rama is an impact-driven tech entrepreneur, investor, and philanthropist. As a partner at Transform VC, she supports tech founders using deep tech for climate and social impact, with a mission to empower 1,000 founders to impact a billion lives and make a billion dollars. Rama has been a key figure in developing the social entrepreneurship ecosystem in the Middle East and leads the VIP.fund, an edTech nonprofit aiding youth affected by conflict. Her work has been recognized in publications like Forbes, Bloomberg, and Arab Women Rising. She holds degrees in Computer Engineering and Engineering Management from George Washington University.
About Transform VC
Transform VC is a Silicon Valley-based venture capital firm that invests in, creates and builds sustainable businesses with a long-term investment view. They focus on mission-driven, determined, and authentic founders who use deep tech and network effects for social and climate impact.
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Aaron Webster, Managing Director at Cameron Ventures, shares his experience in the dynamic world of venture capital, with a focus on InsurTech, FinTech and Enterprise Technology investments at seed and Series A. He explains the evolving trends within these sectors and emphasizes the critical role of data infrastructure in driving innovation. Aaron shares insights into what he looks for in potential investments, particularly the importance of strong data management and the integration of technology with business models.
In this episode, you’ll learn:
[2:39] How Aaron's career in corporate shaped his approach to technology, business and startup investing
[7:55] Key elements of InsurTech 2.0: The shift from distribution to infrastructure and data management.
[12:40] The excitement around data infrastructure plays in the insurance space and why having good data is crucial.
[14:41] How Cameron Ventures sources and evaluates startups, with a focus on team dynamics and problem-solving capabilities.
[18:35] Common reasons for getting a 'No' from VCs and the importance of character and realistic valuations.
[21:48] Advice for founders in the current market, including the significance of understanding market trends and valuation issues
[23:07] The role of venture capital in pushing the economy forward
The non-profit organizations that Aaron is passionate about: United Way Oklahoma, Payne Education Center
About Aaron Webster
Aaron Webster is the managing director at Cameron Ventures. He backs founders who are building the new tech stacks for financial services and benefits and has been instrumental in Cameron’s investment in Castellum.AI, jawnt, YellowBird, Coverdash, XP Health, Certificial, and others startups.
About Cameron Ventures
Cameron Ventures is an Oklahoma-based early-stage venture capital firm with affiliate operating companies that serve customers across the United States, primarily in insurance, banking and asset management. The Cameron team is able to empower its portfolio companies with access to financial and strategic capital, seasoned real-world management teams and a substantial customer base. Companies in Cameron’s portfolio include NewRetirement, Coverdash, Castellum.AI, Certificial, jawnt, YellowBird, Method Financial, Surround Insurance, XP Health, among others.
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Ben Black, co-founder and managing director of Akkadian Ventures, shares insights into the venture capital secondary market. He highlights the distinct approach Akkadian Ventures takes, focusing on businesses with proven customer economics and strong technology moats. Ben elaborates on their strategy of gradually increasing positions and leveraging discounts from secondary investments. He also discusses the evolution and growing importance of secondary markets as startups stay private longer and new liquidity models develop. Ben also talks about Raise Global, a platform he founded to support emerging venture managers.
In this episode, you’ll learn:
[1:39] Silicon Valley thrives on meritocracy, where anyone with ambition, talent, and hard work can quickly connect and succeed regardless of their background.
[4:41] To succeed, emerging managers must proactively create their own opportunities, rather than waiting for them to be given.
[6:46] What is the venture capital secondary market? How is it developing, and what impact does it have on the broader VC ecosystem? What does the future hold for secondary investments?
[12:27] Key strategies for investing in the secondaries market
[22:00] The evolution and impact of Raise since its inception.
The non-profit organizations that Ben is passionate about: Mind The Gap
About Ben Black
Ben Black is a co-founder and managing director at Akkadian Ventures. He has extensive venture capital experience, having previously worked as an investor at Maveron, Rosewood Capital, New Cycle Capital. As an entrepreneur, Black served as vice president of corporate development at Harris Interactive, driving its transformation into a leading internet-based market research firm and leading to a successful IPO. He also co-founded Raise Global to facilitate connections between emerging fund managers and capital partners, enhancing investment opportunities in the venture space.
About Akkadian Ventures
Akkadian Ventures is a Silicon Valley-based direct secondary investment firm that offers liquidity to early employees and investors of venture-backed businesses. For more than a decade, Akkadian has pioneered secondary and opportunistic investments in growth-stage technology companies.
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Venktesh Shukla, Founder and General Partner at Monta Vista Capital, shares his journey from a reluctant immigrant to a successful entrepreneur and venture capitalist. He outlines his investment strategy at Monta Vista Capital, emphasizing deep due diligence, expert validation, adaptability, continuous learning, and leveraging networks. Additionally, he highlights the significant role of TiE (The IndUS Entrepreneurs) in promoting entrepreneurship, particularly among Indian and South Asian communities, and the importance of supportive ecosystems in fostering innovation and economic growth.
In this episode, you’ll learn:
[1:36] Driven into venture capital by a desire to focus on product and customer engagement
[6:53] Presenting unique and intriguing aspects of your field or venture appeals to VC's intellectual curiosity.
[8:36] Monta Vista investment philosophy: high conviction, concentrated investments; relying heavily on deep domain experts to validate investment opportunities.
[14:09] The founder’s motivation to tackle a market problem should be backed by concrete market insights.
[19:52] The IndUS Entrepreneurs - a comprehensive support system that has had a profound impact on the global entrepreneurial landscape, contributing to significant successes within the Indian community in Silicon Valley and beyond.
The non-profit organizations that Venktesh is passionate about: Foundation for Excellence
About Venktesh Shukla
Venktesh Shukla is the Founder and General Partner of Monta Vista Capital and also the Founding Chair of TiE Angels. Prior to investing, Venktesh drove rapid growth in sales, marketing, and general management roles, collaborating with over 50 startups. As a former president of TiE, he strengthened Silicon Valley’s tech startup network and continues to volunteer, connecting entrepreneurs with key customers. Passionate about supporting Indian startups, Venk influences policy through the Government of India's Startup Advisory Council and supports students through the Foundation for Excellence.
About Monta Vista Capital
Monta Vista Capital is a Silicon Valley-based venture capital firm focused on early stage B2B companies. Portfolio companies include StrikeReady, Uhnder, minds.ai, ConstructN, XY Retail, Eridan, Boomerang, Motorq, Sparkz among others.
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Gayathri Radhakrishnan, partner at Hitachi Ventures, shares profound insights from her journey and perspectives on venture capital and technology. Gayathri reflects on her early life in India and how her competitive spirit and supportive family shaped her path to challenging norms in male-dominated fields. She delves into her focus on impactful investments in AI, utilizing Hitachi Ventures' corporate strengths to strategically nurture startups. Gayathri values founder passion, problem understanding, and openness to feedback, and her advice to founders stresses preparation, boldness, and leveraging networks for lasting partnerships and growth.
In this episode, you’ll learn:
[1:54] The making of Gayathri Radhakrishnan: Challenging norms and building a strong sense of confidence and competitiveness.
[10:32] The responsibility and impact that venture capital has on shaping future generations
[14:10] Impact of corporate venture capital, when done right: Hitachi Ventures’ commitment to patient capital with a 10-year fund cycle further underscores their long-term support for startups.
[18:21] Trends and opportunities: Entrepreneurs should explore opportunities where AI can revolutionize industrial processes, enhance safety and efficiency, and contribute to sustainable practices.
[23:37] Passionately understand your problem, stay open to feedback, and ensure your solution has real-world validation and market potential.
[28:20] Aim for follow-up meetings and leverage the investor's network for potential introductions.
[35:15] What’s the immediate threat posed by AI?
The non-profit organizations that Gayathri is passionate about: SV2
About Gayathri Radhakrishnan
Gayathri Radhakrishnan is currently Partner at Hitachi Ventures, focusing on AI investments in Manufacturing, Healthcare, and Automotive. With over 20 years in technology, she has held roles at Dell, Corning, and Micron Ventures, and served as a Partner at Earlybird Venture Capital. Gayathri holds an MS in EE from The Ohio State University, an MBA from INSEAD, and is a Kauffman Fellow. She has driven strategy at Dell’s Software Group and mentored startups at TechRanch Austin and Techstars Cloud.
About Hitachi Ventures
Hitachi Ventures is the global venture capital arm of Hitachi Group. Hitachi Ventures invests in innovative companies that address society’s key technological challenges in areas like IT, industrial automation (robotics, sensor technology and IoT), cloud services (data management, cybersecurity), mobility (autonomous driving, mobility services, smart infrastructure and security services), energy, smart medicine (AIfor digital imaging, smart diagnostics, remote care), smart city, smart infrastructure and more. It’s portfolio includes companies such as Samsara Eco, Trustwise AI, WEKA, StrikeReady, Archetype AI, WASE, Cure51, Proscia, Thea Energy, Captura among others.
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Dan Kimerling, founder and managing partner at Deciens, talks about key principles that shape his current approaches to startup investments. He explains Deciens' strategy of leading financing deals with a concentrated portfolio, allowing for deep partnerships with entrepreneurs. Dan critiques the average venture capital returns and promotes a bold, non-orthodox strategy to achieve exceptional outcomes. He emphasizes the importance of alignment with entrepreneurs and LPs, advocating for a venture capital model that values courage, commitment, and long-term relationships over diversification and transactional interactions.
In this episode, you’ll learn:
[1:48] How growing up in Edison, New Jersey, influenced Dan Kimerling’s personal and professional life.
[4:07] Deciens’ philosophy: Concentrated, bold, partnership-driven investments.
[7:42] Founders seek genuine partnerships with VCs.
[15:54] Achieving greatness requires personal courage, not group consensus.
[18:28] Success in VC means investing in non-consensus deals with a robust framework.
[29:28] Strategies for better alignment among VCs, entrepreneurs, and LPs.
The non-profit organizations that Dan is passionate about: Albuquerque Community Foundation
About Dan Kimerling
Dan Kimerling is the founder and managing partner at Deciens. He is passionate about leading investments in transformative companies at their earliest stages and sits on the board of many Deciens portfolio companies, including Chipper, Therma, and Treasury Prime. He co-founded Standard Treasury, which was acquired by Silicon Valley Bank, where he led API Banking and Global Research. Earlier, he was an analyst at TechCrunch. Dan graduated with honors from the University of Chicago with an A.B. and A.M., studied mathematical finance at Booth, and received several awards. He was named to Forbes’ "30 under 30," is a Kauffman Fellow, and is active in the Young Presidents’ Organization.
About Deciens
Deciens is a venture capital firm dedicated to supporting early-stage founders revolutionizing financial services. The firm identifies visionary entrepreneurs at the inception of their journey, offering extensive support beyond funding to realize their visions. Deciens collaborates strategically with industry leaders such as Chipper Cash, Africa's largest fintech; Treasury Prime, a frontrunner in banking-as-a-service; and Therma, an innovator in industrial energy management. Through these partnerships, Deciens champions entrepreneurs driving the digital transformation of traditional institutions.
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Vishal Tripathi, investor at Next Legacy Partners, delves into venture capital dynamics, spotlighting Next Legacy Partners' unique blend of philanthropy and athlete-focused strategies. Vishal shares his journey into venture capital, underscoring the industry’s allure for innovation and human connection. He also discusses key insights including the importance for emerging managers to define their unique differentiation and adapt to investor preferences, evaluation criteria for managers, AI's transformative role, and the need for VC innovation amid challenges like prolonged private company timelines.
In this episode, you’ll learn:
[1:20] Venture capital allows you to engage with and learn from driven entrepreneurs at the forefront of innovation.
[5:14] Next Legacy Partners mission: linking philanthropy, athletes, and cultural figures with venture capital.
[6:49] Define your unique differentiation as an emerging manager.
[10:27] Emerging managers should align their strategy with their unique strengths and personal approach, remaining open-minded instead of adhering to any one-size-fits-all model.
[21:39] Emerging trends in venture capital, including AI's transformative impact and the need for innovation to address challenges like liquidity and evolving market conditions.
[28:03] VCs should prioritize founders as their primary customers and focus their efforts on adding value to them.
The non-profit organizations that Vishal is passionate about: Anjali, Smile Foundation
About Vishal Tripathi
Vishal Tripathi is an investor at Next Legacy Partners. Vishal analyzes and oversees venture capital funds and industries at Next Legacy, leveraging prior roles as a portfolio manager at Plexo Capital. With a background in financial engineering and quantitative research at J.P. Morgan, he brings extensive expertise in capital allocation and early-stage venture capital. Beyond his professional endeavors, Vishal finds enjoyment in reading DC comics, watching UK panel shows, developing computer games, and avidly following Cricket and Chess.
About Next Legacy Partners
Next Legacy Partners is a venture capital firm formed from the merger of Legacy Venture and Next Play Capital. It stands out with its dual mission to connect the philanthropic world with venture capital (Legacy Venture's focus) and to bridge athletes and cultural luminaries with venture capital (Next Play Capital's focus). Next Legacy Partners is highly community-driven and distinctively focuses on established large funds, direct investments into startups, and emerging leaders in the venture capital industry.
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Atlas Berry, founder and general partner at Mission One Capital, delves into funding mission-driven founders who focus on frontier technology solutions to sustainability challenges. Atlas discusses the significance of sustainability to him personally, highlights the specific areas of climate tech his venture capital firm targets, and explores current trends in the industry. He provides deep insights into sustainability opportunities and shares valuable advice for entrepreneurs interested in this sector.
In this episode, you’ll learn:
[1:41] 'Jason Bourne meets banking': The fascinating early career journey of Atlas Berry.
[5:22] How corporate development experience paved the way for a venture capital role.
[6:33] The inception of Mission One Capital: Identifying software-driven solutions to climate issues.
[12:17] Guidance for founders tackling climate and sustainability challenges: Understand the problems in these areas and respecting regulatory constraints.
[16:35] The importance of addressing human issues for successful sustainability solutions.
[20:22] Emerging trends in climate tech, including energy, mobility, carbon markets, circularity, and environmental management.
[26:00] Why timing is crucial in evaluating sustainability-focused investment opportunities.
The non-profit organizations that Atlas is passionate about: The Nature Conservancy
About Atlas Berry
Atlas Berry is the founder and general partner at Mission One Capital. He began his career in investment banking at JPMorgan, working in Mergers & Acquisitions across New York, Johannesburg, and London. Notably, Atlas established the venture arm for the Grammy-award-winning rock band Linkin Park, where he led investments in high-profile companies such as Lyft, Robinhood, and Impossible Foods. Additionally, he is a two-time TEDx keynote speaker, has mentored at Techstars and the MIT Startup Accelerator, and has served on the Technology Advisory Boards for New York City and Delta Airlines.
About Mission One Capital
Mission One Capital is a Silicon Valley-based early-stage venture capital firm specializing in ClimateTech and Equitable Access startups. The firm invests in seed-stage companies dedicated to creating a more sustainable and equitable future. Its portfolio includes innovative companies such as Zevvy, Twice, Helio, Cloverly, CHI, Derapi, UPFRONT, Carbonara, and others.
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Chris McKelvy, founder of K. Ventures and military veteran, recounts his journey from the military to tech companies like Oculus VR and Meta, culminating in establishing his own venture capital firm. Chris talks about his early involvement in JFK family's non-profit initiatives and getting inspired to start K. Ventures, focusing on the disabilities community. Chris also shares useful tips for founders on preparing for meetings with VC and encourages VCs to address societal challenges.
In this episode, you’ll learn:
[1:45] Transferring military leadership skills to tech and investing for social impact
[4:14] K. Ventures takes a unique approach to disabilities by investing seed capital in startups serving this community.
[6:22] Startup opportunities: The disabilities community is the largest underrepresented group in the world.
[9:23] It takes a lot of mentorship and support to learn the craft of being an entrepreneur.
[16:27] Feel comfortable in the way that you want to talk about your business and yourself.
[19:18] VCs are guided by their belief in the founding team's ability to lead and create something groundbreaking.
[22:35] More investors need to really think about the hard societal problems
The non-profit organizations that Chris is passionate about: Joseph P. Kennedy, Jr. Foundation, iMentor
About Chris McKelvy
Chris McKelvy is the founder and managing partner at K. Ventures. He has a diverse background spanning tech, business, non-profits, and the military. Notably, he led Oculus VR's partnerships & e-sports division, instrumental in its $2B acquisition by Facebook. Chris orchestrated multimillion-dollar partnerships with tech giants like NVIDIA, AMD, Intel, Unreal, and Ubisoft. A combat veteran with the 101st Airborne Division and graduate of Army Ranger school, he holds degrees from Harvard and Syracuse. Additionally, he served proudly as Vice Chairman of the Joseph P. Kennedy, Jr. Foundation for over eight years.
About K. Ventures
K. Ventures is a Massachusetts-based venture capital firm with a mission to catalyze the next generation of disability care. The firm invests in early-stage technology companies serving those with intellectual, developmental and learning disabilities. This includes down syndrome, autism, ADHD and dyslexia as well as other overlooked conditions. Portfolio companies include Juno, Juniper, Mightier, Finni Health, and NeuroNav.
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The podcast currently has 151 episodes available.