The Sure Shot Entrepreneur

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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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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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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Tommy Leep, founding partner at Jetstream, shares insights on climate tech investing and nurturing startups for a sustainable future. He delves into climate tech trends, opportunities for startups, and challenges that early-stage investors face (such as greenwashing). Tommy also advises founders on articulating their vision, avoiding the "founders' curse of knowledge" and the importance of sales skills.

In this episode, you’ll learn:

[2:05] Startups attract people who love to be part of disruptive innovation.

[4:53] Finding purpose in setbacks: the story of how Jetstream started

[9:59] Trends and opportunities in climate tech investing.

[14:03] Building a startup in the climate tech space

[19:47] Founders’ curse of knowledge - what is it? How can founders avoid the curse of knowledge?

[25:21] There’s something special about a founder who can influence an investor to make subjective decisions.

About Tommy Leep

Tommy Leep is the founder of Jetstream. He is a seasoned entrepreneur, investor, and business advisor with experience in startup funding and growth. He held key roles at Floodgate and Rothenberg Ventures before delving into venture capitalism. With experience at Meraki, Inc., Intuit, and Yahoo! Music, he brings a diverse skill set. Tommy advises startups like Around, Payable, and Patreon, and formerly led Rothenberg Ventures' SF office. He's also advised Orchestra Inc. (now part of Dropbox).

About Jetstream

Jetstream is a venture capital firm investing in pre-seed climate, sustainability, and biodiversity startups. Companies in Jetstream’s startup portfolio include Verdi, Pachama, Windborne Systems, Glacier, Albebo, Lightship, Pathways, Cecil, Wildgrid among others.

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Eric Sippel of Sippel Farb Family Office delves into the intricacies of investing in emerging managers. Eric outlines his meticulous emerging manager selection criteria, emphasizing his preference for specialists over generalists. He highlights key challenges of identifying good VCs as a Limited Partner (LP), and offers insights into the shifting venture capital landscape. In addition, he discusses the importance of supporting underrepresented venture capitalists for enhanced portfolio returns.

In this episode, you’ll learn:

[1:33] Venture’s main appeal is the ability to disrupt and create positive change.

[4:25] Is it hard to find a good VC to invest in as an LP? Why is that so?

[12:54] Eric Sippel’s emerging manager selection rubric; 3S (sourcing, selection, and stewardship/value add) - which is the most important S?

[26:18] What happens in the first, second meeting with an emerging manager? What questions should VCs expect from Eric?

[33:03] Investing in underrepresented VCs isn’t just ‘good’. It’s critical to having a broader aperture for outsized portfolio returns.

The non-profit organization that Eric is passionate about: Goodwill San Francisco Bay

About Eric Sippel

Eric Sippel invests in emerging managers through his family office, Sippel Farb Family Office. He’s also a philanthropist and current chair of Bay Area Goodwill.

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