Podcast Summary:

The Investor with Joel Palathinkal
Episode Title: Arun Krishnakumar: Partner, Greenshores Capital
Date: September 22, 2025
Featured Guest: Arun Krishnakumar, Partner at Greenshores Capital
Host: Dr. Joel Palathinkal

Overview

In this episode, Dr. Joel Palathinkal sits down with venture capitalist, author, and influencer Arun Krishnakumar to explore his journey from engineering and corporate finance to becoming a partner at Greenshores Capital. The conversation covers Arun’s path into VC, navigating career crossroads, building networks, the evolving landscape of fund management, investment strategies, cross-border challenges, and reflections on founder mental health. Students and early-career professionals in the audience also pose practical questions about industry learning curves and partnership dynamics in venture investing.

Key Discussion Points & Insights

1. Arun’s Path to Venture Capital

[05:47–08:43]

• Background: Originally an engineer from India, Arun spent 15 years in the UK, held senior roles at Barclays and PwC (in data analytics, blockchain, and fintech).
• Career Pivot: Launched a “soul searching initiative” around 2012, meeting over 50 professionals (bankers, traders, VCs, academics) to understand different deal-making roles.
• Transition to VC: Leveraged his tech and financial services expertise to move into fintech and investment after concluding he wanted to be in the deal-making space.

“I knew that I wanted to be in the deal making space. So, being a tech guy with a lot of financial services experience, my logical transition was into a fintech-stroke investment space.” – Arun [07:24]

2. Building a Network in VC & Writing His Book

[09:16–12:09]

• Network Growth: While writing his book, Arun interviewed ~50 people, starting with acquaintances and expanding by always asking each interviewee for “just one more introduction.”
• Relationship Building: Stressed the importance of quality, respectful outreach and organic yet well-prepared conversations for expanding networks and accessing big names in the industry (e.g., Brad Feld of Foundry Group).

“Every time we got someone to interview, we said, hey, can you introduce us to one more? … Our network started becoming wider and wider and people started introducing us to kind of like bigger, bigger, bigger names.” – Arun [09:43]

3. Approaching Cold Outreach

[13:29–14:08]

• Recommends short, relevant, and respectful messages that quickly demonstrate the sender’s research, shared interests, and agenda.
• Values personalized, to-the-point communication over generic cold pitches.

4. Why VC? Deciding Between Career Paths

[15:22–18:59]

• Grandparent Metaphor: Describes the VC’s role as “a grandparent” – can support and advise founders while keeping some distance, unlike the hands-on involvement of an entrepreneur (“parent”).
• Need for Variety: Values the intellectual stimulation from interacting with diverse founders and sectors; acknowledges getting bored easily.

“As an entrepreneur, you are a parent, parent of the organization you’re running. … But as a VC, you are a grandparent. You actually can take a step back when you want. You can pass judgment on the judgment of the parent.” – Arun [15:22]

• Challenges: VC fundraising for funds is often harder than raising for individual businesses; selling a “blind pool” requires significant trust in GPs (general partners).

5. Founding Greenshores Capital

[19:10–20:27]

• Arun is a founding partner; the brand originated with his vision.
• Started as an angel syndicate; initial cornerstone investors in his first fund became his future partners.
• Strong emphasis on relationship-driven firm formation.

6. The Future of Fund Management: Rolling Funds, SPACs, and Incentives

[20:45–23:48]

• Finds certain aspects of traditional fund models outdated, especially management fees.
• Rolling funds (like those on AngelList) provide early-stage managers a track record before institutional rounds; lauds the liquidity potential of SPACs even if not without risks.
• Sees room for improvement in aligning incentives for both GPs and LPs (investors).

“There are several things I hate about the fund model personally as fund manager, but I also hate some aspects of fund management from a startup perspective.” – Arun [20:45]

7. Greenshores’ Investment Focus and Process

[23:48–26:49]

• Stage: Prefers companies with some revenue and traction (pre-Series A or Series A); not “idea-stage” investors.
• Sector Breadth: Looks across fintech, healthtech, telecom, sustainability, climate tech—sector-agnostic but guided by interest and capacity to add value.
• Due Diligence: Particularly rigorous on fintech given partners’ banking backgrounds.

“We tend to be harsher on fintech deals because all of us come from a banking kind of financial services background. So it’s very hard for fintech companies to bullshit around the due diligence process.” – Arun [24:38]

• Conviction: Occasionally invests personally in deals rejected by partnership, later re-proposes them if results justify.

8. Cross-Border Complications (India, UK, US)

[26:51–30:06]

• India: Prefers using local funds for Indian investments due to cross-border complexity and taxation issues.
• UK: Investment vehicles (convertibles, notes) are similar. Challenges sometimes arise for US LPs or investors, necessitating offshore vehicles.

9. Learning Curve for New Sectors

[30:32–32:24]

• Strategy: Dives into research, seeks out friends and experts, conducts interviews to quickly understand unfamiliar domains.
• Due Diligence is Shorter for Non-Core Areas: Reviews are lengthier and more demanding for familiar sectors, lighter when learning anew.

10. Partner Alignment and Disagreements

[32:48–36:08]

• Process: Open dialogue, negotiation, and “whiteboard sessions” to balance concerns and mitigate red flags.
• Role of Partners: Knows which partners need more technical explanations or business rationales.
• External Experts: Hires auditors or subject matter experts for specialized due diligence as needed.

11. Secondaries and Fund Vehicles

[37:03–39:23]

• Embraces SPVs and Secondaries: Likes offering coinvestment opportunities to LPs and supports private market secondary liquidity solutions.
• Industry Trends: Predicts more digitized stock exchanges for private assets, and greater structural flexibility.

12. Mental Health of Founders and Investors

[40:15–43:45]

• Personal Focus: Talks about the centrality of founder mental health, especially in crisis situations – inspired by stories from interviewees like Brad Feld and Jerry Colonna.
• Advocacy: Stresses the need for more open conversations and less stigma about mental health challenges in entrepreneurship.

“…people don’t spend enough time on their mental health, especially as entrepreneurs. It’s like asking Usain Bolt to run this Olympic without a personal trainer.” – Arun [41:00]

Notable Quotes & Memorable Moments

• On Building Networks:
  “You can get to anyone in the world if you really keep hopping like that. Just one more intro, everybody.” – Arun [09:43]

• On Why VC:
  “I quite like that role if you like. But the other thing that helped me make the decision is I am a guy who gets bored easily, which is why I have different interests.” – Arun [16:08]

• On Fundraising for VCs:
  “Go out, you’re selling a fund, it’s really a blind pool of capital … it’s a much harder sale.” – Arun [18:27]

• On Mental Health:
  “Running a startup itself is a crisis. … There needs to be more stories that comes out about the mental health of entrepreneurs.” – Arun [41:00]

Audience Q&A Highlights

• How does the team get up to speed in unfamiliar sectors?
  Arun details a research- and expert-driven approach and prioritizes outside validation for highly technical sectors. [30:32–32:24]
• How do you handle internal disagreements?
  Open negotiation, whiteboard sessions, understanding each partner’s style, and sometimes enlisting third-party expertise. [32:48–36:08]
• Views on secondary vehicles and SPVs?
  Positive on secondary markets for liquidity and the evolving ecosystem of SPVs. [37:03–39:23]
• Complexity of investing in India and the UK:
  Cross-border is complex; local vehicles often preferred. [26:51–30:06]

Closing Thoughts

• Arun’s commitment to both intellectual discovery and personal connections has defined his career and investment approach.
• He advocates for a balanced life as a GP, continuous learning, and empathy towards both entrepreneurs and co-investors.
• The episode ends with a reminder to take care of mental health as seriously as business strategy, and an announcement of Arun’s upcoming book on navigating crises in startups.

For more about Arun Krishnakumar and to stay updated on his book release, visit his website or connect directly as shared during the episode.