Arun Krishnakumar: Partner, Greenshores Capital

Summary

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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

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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.

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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]

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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]

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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.

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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).

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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.

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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]

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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.

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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.

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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.

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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.

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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.

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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]

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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]

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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]

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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.

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

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Transcript

[Kelly Clarkson]

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[Arun]

Wayfair. Every style, every home.

[Joel Painkle]

Welcome to the Investor, a podcast where I, Joel Painkle, your host, dives deep into the minds of the world's most influential institutional investors. In each episode, we sit down with an investor to hear about their journeys and how global markets are driving capital allocation. So join us on this journey as we explore these insights.

[D]

Positions across startups. I've dabbled with game analytics and for the last five years have been in freight tech in Dubai itself. And currently I'm working with the folks who are making the world's first IVA for freight and I'm helping them raise funds and yeah, looking to make a shift towards fundraising for general industries, which is what brings me here.

[Joel Painkle]

Great. Yeah, thanks. So Arun, just so you can, we'll go around the room real quick if that's okay, that we can kind of get to know the audience.

[Arun]

Sure, sure. For people wondering why my name comes across as Mira. It's my daughter's name and we use my, my laptop for other things as well. Sorry about that, I haven't managed to change that.

[Joel Painkle]

No, no worries. I think one thing that we could talk about in a few is just work, life, balance, being a dad. Because, you know, this time was work made sense for you because I'm in the same boat. You know, 5pm is like family time. So I think we can, we can bring that up as a topic too. But why don't we just go around the room really quick? So Matthew, Ricky and Stephane, you want to just do like a, like a 30 second intro? Just introduce yourselves. That way Arun kind of can get to know the audience a little better.

[Matthew]

I can jump in quickly.

[Joel Painkle]

Yeah. Hey, Matthew, go ahead.

[Arun]

Hello.

[Matthew]

Yeah, so hi, I'm Matthew. I'm from South Africa. I was actually in Hong Kong before this and got exposed a lot to investment and VC training, et cetera. I'm actually in a startup at the moment, so I've learned a lot about the funding processes and yeah, I've really enjoyed learning from Joel. He's taught me a lot and really insightful to learn the other side of funding, not trying to source it, but actually looking into how it's sourced in the first place. So yeah, it's been really interesting.

[Joel Painkle]

Great. And Stephane, want to say hello?

[Arun]

Sure.

[Stephane Fouche]

Hey everyone. So it's Stephane Fouche and I've been working in Japan for the last five years and I relocated back to America last year. My specialty is strategy consulting. I helped a lot of Japanese corporates to enter the East African market and I also help them with a lot of crisis management. So when they have issues with marketing issues with like when it comes to like the US expansion problems internally. So I've been mainly mostly fixing the marketing side. So like the site that when they're facing with the public, relocated to the.

[Arun]

US not because I wanted to, but.

[Stephane Fouche]

I'm a green card holder so I had to relocate back to America to apply for citizenship. If not, I would be using my green card.

[Joel Painkle]

Cool. And Ricky, wanna say hello as well and then I think we'll kick it off.

[Ricky]

Yeah. Hi everyone, I'm Ricky. I am currently a junior at Cornell University, double majoring in applied Economics and management and Information Science. So I was born in Tokyo, I grew up in Shanghai and now I'm. I was supposed to be in the US but because of the pandemic I'm still in Japan and I'm still mainly exploring different career paths. And I'm really interested in finance just to learn more about it. And going through virtual venture capital training is really interesting and it's been very rewarding as well.

[Joel Painkle]

Great. And we got one more person that snuck in. So Gigi, want to say hello.

[Gigi]

Hello. Can you hear me?

[Joel Painkle]

Yeah, we can.

[Arun]

How you doing?

[Joel Painkle]

Good.

[Gigi]

Hi, Joe. Hi, Aaron.

[Joel Painkle]

How's it going? We're just doing quick intro. So if you want to. So you want to tell them a really quick intro on your background and then we'll kick it off with the room.

[Gigi]

Yeah, sure. So I'm from Taiwan and currently based in Hong Kong and I'm working for expert network called glg. And so we connect, we basically connect subject matter experts to the investors to solve their research topics or whatever company industry that they are learning with. And I think just based on this experience, I got interested into private equity and also venture capital world. So like taking on this program to gain some knowledge and experiences. So it's great connecting with you guys.

[Joel Painkle]

Really great. Awesome. Well, hey, Arun, we'll just kick it off, you know, I know you don't have too much time, so want to just spend some time to kind of just Help the students understand a little bit about maybe your career, how you navigated to vc. And then maybe we'll cover a couple topics like maybe your investment thesis and just managing, managing your life as a fund manager. How's that sound? So maybe you can just kick it off with a quick bio. And you know, I read your bio too. You've done a couple things too. I think you've written a book and you know, been an influencer in different areas. So we'd love to, you know, learn about some of those areas of your life as well.

[Arun]

Right? Okay, sure. So I'm originally an engineer from India based in this country for the last 15 years or so in the UK in London and in terms of my career path, was a corporate guy until about 201314 did most of my corporate career within Barclays and towards the end of my corporate career I was part of the Leadership team within PwC's Data analytics blockchain and fintech practice. Did a bunch of business degrees in the UK as well. And 201314 is when, or probably a couple of years before that. 2012 was perhaps when I started kind of launching a soul searching initiative where I knew I didn't want the career that I was doing at that time. I didn't want to be a corporate guy I didn't know out there. So I met up with about 50 professionals across investment banking, trading, risk management, fund management, private equity, hedge funds across the board, academia as well and was trying to understand what their day job looked like and 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. And that's how I've kind of navigated my career over the last eight years or so. So over the last eight years, the way it's now turned out to be, some of them were planned, some of them weren't. So the ones where 20 investments, five to five, six board positions and I'm also a board of trustees in an NGO in India focused on water conservation, although it's all been killed by the COVID at the moment. So we are. Okay, so that's the planned bit. The author bit wasn't as planned as I thought. I've always loved content creation. So I've done about 150 articles for Daily FinTech, about 100 podcast episodes for my my own podcast. But the author I just got headhunted to write a book about two years ago, but the process I thoroughly enjoyed. So I Just said, okay, I'm doing it. So I'm currently now in the process of closing off my second book. It's coming out in Jan. And so that's, that's my author career, my influencer career was completely unplanned. So it's like it just happens. Happened because I'm quite a. I'm quite vocal and I'm quite kind of. I can't keep things. I can't keep quiet. I just go on social media and make noise. So because of that, people just say, okay, you're an influencer. That's, that's completely a byproduct of whatever I do in the investor and author columns. Sure, yeah, yeah.

[Joel Painkle]

They all kind of, they all kind of support each other. Maybe you can give some insights or some special tips on how you're able to set up all these meetings. I think you and I met on LinkedIn and that's common for people in the investor ecosystem to kind of build new friendships. Sometimes they're cold and then they turn into warm friendships. But, you know, how did you connect with them? Was it mostly just LinkedIn messages and like informational. Well, when you set up all those meetings to learn about different industries. Right. I think you set up some meetings with some private equity professionals and, and bankers. Yeah. For your career. Yeah.

[Arun]

So, I mean, actually I. Instead of going back eight years, I can actually talk about the bit that I've been doing over the last six months or so. Right. When I started writing the book, it's. Writing and doing the strategy bit was largely my proprietary thinking. But I interviewed about 50 odd people and a good chunk of them I hadn't met before. Like, for instance, we managed to get Bradfield, the Foundry Group in the us.

[Joel Painkle]

Oh, wow, that's great.

[Arun]

When we started writing, and that's. That's the guy whose book I used to kickstart my venture capital career. To get him as a, as a interviewee of my book was amazing. But we didn't get there on day one. Every time we got someone to interview, we said, hey, can you introduce us to one more? Just one person? So that was our final question to every single person we interviewed. So our network started becoming wider and wider and people started introducing us to kind of like big, bigger, bigger, bigger names. And we got to the board of directors of Barclays. We got. I mean, you can get to anyone in the world if you really keep hopping like that. Just one more intro, everybody. And that was a strategy we used. It worked quite well for us, which.

[Kelly Clarkson]

Got us to Brand, it's Kelly Clarkson here to talk all things Wayfair. The best place to buy furniture, decor, and anything else you can think of to create a home you absolutely love. I know when I shop with Wayfair, I find options for every sty. Whether I'm feeling boho or farmhouse, modern, traditional, French country, I can find exactly what I need for my home and more. No matter your space, style or budget, shop wayfair.com to make your home way more you.

[Arun]

Wayfair. Every style, every home. Well, and he was super down to earth. Like, it was like this conversation. We could just speak to him like a mere mortal. Right, so.

[Joel Painkle]

So it sounds like your strategy was really, you know, building the friendship and then really asking, you know, for more of a warm intro. And then it kind of just turned into like a network effect of warm intros.

[Arun]

Right, Absolutely. And the other thing I would have, I would say is you need to demonstrate quality in the time that you actually have it. Right. So for instance, I. Who put us in touch with Bradfield was his friend Jerry Colin. Now whom.

[Joel Painkle]

Yeah.

[Arun]

And the conversation with him was amazing. He had 30 minutes. He said, Guys, I can only give you 30 minutes. But at the end of the 28th minute, he said, I'm quite enjoying this conversation. I can give you 15 more minutes.

[Joel Painkle]

That's a good sign.

[Arun]

And that he wasn't the first guy who did that. I mean, there were like bunch of other people who said, I have only 30 minutes. I would only have 45 minutes. And then say, I'm loving this conversation. Can we. I'll push my. Just give me a minute. My next meeting to a later date. And that really kind of is the validation to say, okay, you're having a really quality conversation and you're going to probably take away a lot more than.

[Joel Painkle]

Yeah. And it's probably important to be prepared too. Right. So did you have like a format that you. That you made sure you had prepared or was it more of like an organic conversation?

[Arun]

The conversation looks organic. It doesn't look prepared. But we do prepare a lot. So. And most people we interview, we kind of see being the VC space, we know most people who are in the VC space, the kind of job they have done, the kind of exits they have had. And all we do is then, for instance, when we spoke to Fred Destin at Stride vc, we knew he was a Zoopla investor. And the investment happened at the peak of the credit crisis in 2008.

[Joel Painkle]

So that just.

[Arun]

Sorry, that just helped us ask the right question to him saying, hey, how did you do that? Because it was the height of housing crisis, housing market was crashing, and you did it in a firm that was focused on how kind of the real estate industry. So he knew that we had done the research. So it was still an organic conversation, but it was, it was quite, quite fun. So you have to do the research. I mean, even in the introduction email, I don't mind cold pings. I see who pinged me out of nowhere, so. And as long as the cold ping is respectful, shows relevance, if someone writes to me saying, hey, do you want my IT services? I'm not going to even respond to that.

[Joel Painkle]

Sure.

[Arun]

But if someone is going to reach out to me saying, I did read your profile, I went through your website, this is what seems to be your area of interest. This is my core thesis. This is the core thesis of my firm. That seems to be synergies. Would you like to have a chat?

[Joel Painkle]

Yeah.

[Arun]

Very short, relevant, respects my time. I don't like, I don't read long, long. So those are the little things. And for instance, for all you know, if you ask someone else, they will tell you different things. But for me, this is, these are my criteria. It has to be relevant, it has to be quick. And it. And it has to tell me enough for me to feel interested about it as well.

[Joel Painkle]

Yeah, yeah, absolutely. I think just the etiquette and just really the delivery of the message and just the scope of it, you know, it really helps because you, because everybody gets so many messages coming into their inbox. And you know, funny story is this is how we're doing this podcast now. You know, I think I pinged you and we hopped on a call, you know, so I think the format that's worked for me with Deal Flow for building relationships is really like, hey, you know, are you interested in getting to know each other? Why don't we do like a 20 minute first call and then I think there should be some type of synergy at the end. Just saying, hey, you know what, let's, let's do a podcast together. Let's do something that's collaborative together. And I think that's always helpful if it's like a short, actionable point to look into. But that's great. And then one more question on the career front and then maybe we'll get into Green Shores. So as you were talking to all these different professionals, you're talking to private equity professionals, bankers, traders, and then probably some VCs. What made you end up finally deciding that VC is a career choice for you. And I ask because some people are really trying to think about what their next step is in the audience. So I think it'd be good to know what your frame of mind was. And it's like, you know what? I think VC is maybe the good next step for me.

[Arun]

One of the things I knew about myself was I kind of. What's the right way of saying this? So as an entrepreneur, you are a parent, parent of the organization you're running. So you've got to be hands on, you've got to be on a day to day basis in the ops. But as a vc, you are a grandparent. You, you actually can take a step back when you want. You can pass judgment on the judgment.

[Joel Painkle]

Of the parent if you know that's really interesting. I haven't heard that expression. So, so what you're saying is as a grandparent you don't have to, what you're trying to say is you don't have to directly tell the company what to do. You're trying to let the company just do their job. Where if you're a parent you'd be kind of ordering them around.

[Arun]

That's perfect.

[Joel Painkle]

Yeah, I heard that once.

[Arun]

I quite like that role if you like. But the other thing that kind of made help me make the decision is I am a guy who gets bored easily which is why I have different interests. Right. Writing, investing and of course social media. Talking about things on social media.

[Joel Painkle]

Yeah.

[Arun]

I need the same kind of variety in my portfolio as well. I can't get, I mean there have been multiple portfolio founders in my own portfolio who's offered me C suite roles and I'm sure lots of other VCs will tell you the same stories. But I can't tag myself to one one firm because I just get bored within. I know I get bored within a short span of time. And what, what I really enjoy in this journey and I knew this when I spoke to these people, is that you, you get to meet. I mean we used to be, we used to have these kind of crash or kind of fast crash date or quick date or whatever you want to call it. Like almost like a fast paced meetings like 45 minutes, 15 minutes debrief. 45 minutes, 15 minutes debrief. Like seven to eight entrepreneurs walking through the door in a day.

[Joel Painkle]

Sure.

[Arun]

And that is when all our partners are in the room in London and this happened until March and after that it's all zoom. But we, we used to have that and we used to have that variety of people coming in be it healthcare, fintech, telecoms, sustainability, climate change, I mean, climate tech. So so many different use cases, all coming to you with the energy, the passion and the love for what they're doing that, I mean, you can't ask for more, right? So you get to meet all these driven people and you learn a lot of all this. So that's really what made me fascinated about this industry. There are challenges, right? I mean, VCs have tougher time raising funds than businesses. If you have a very pure business that you want to go and raise funds for, I can sell it super easily because I know exactly what I'm doing, precisely what I'm doing, what my revenue model looks like, what my cost model looks like, and just have to demonstrate it's a viable business, a very easy sales process, I mean, relatively. But go out, you're selling a fund, it's a really a blind pool of capital and the people investing in the fund are people who are really investing in the founders or the gps of the fund, in the quality of the GPS of the fund. So it's a much harder sale. You ask any VC in the world, they'll tell you that. Of course, the sequoias and the A16Zs are in a different league altogether, but people who are still in the early stages of their VC career, like myself, they're gonna tell you it's, it's super hard to raise funds for a vc. So it's you, you've got to really know what you're doing. So that's the pros and cons of the game. It's not all rosy.

[Joel Painkle]

Rosy, yeah, absolutely. And I guess for the, for Green Shores, would you. Were you one of the partners helping to raise money or did you just come on as a strategic hire to kind of support my baby? Oh, it's your baby.

[Arun]

Okay. Yeah, I just pick it up at 4am on a day. I just said text to my partners. This is what we're going to call it.

[Joel Painkle]

Okay, got it.

[Arun]

The branding process, it just.

[Joel Painkle]

How did you pick your, how did you pick your team members? So were they just, you know, colleagues of yours? How did you guys come up? How did you guys decide to start the fund? Were they just, you know, other.

[Arun]

Both the funding members or. Sorry. Both the partners of insurers were my cornerstone investors in my first fund.

[Joel Painkle]

Got it.

[Arun]

So when we said, okay, we wanted to kind of create, we initially were like an angel syndicate, then put it into a fund structure and raise funds for that. And at that time, these two gentlemen were cornerstone investors. And then they were planning to set up a fund. And they kind of said at the last, our last due diligence meeting of the first fund, they said, hey, would you want to be kind of helping us out, set this all up? And you've done this once. Can you come in and do all this for us? We'll work on a partnership kind of model. And we said, yeah. I mean, like, I mean, this is the ex CTO CIO of Citigroup Consumer bank asking me, would you want to be my partner? Why would I say no? So that's amazing.

[Joel Painkle]

And what do you think the future holds for fund management? We're talking about rolling funds and we're talking about kind of everybody doing a portfolio of SPVs. So do you think that we got SPACs now so we don't even have to do IPOs anymore? We can just go directly to the IPO first without a company. Right.

[Arun]

So there are upgrades you could have across the board. 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.

[Kelly Clarkson]

It's Kelly Clarkson here to talk all things Wayfair. The best place to buy furniture, decor, and anything else you can think of to create a home you absolutely love. I know when I shop with Wayfair, I find options for every style. Whether I'm feeling boho or farmhouse, modern, traditional French country. I can find exactly what I need for my home and more. No matter your space, style or budget, shop wayfair.com to make your home way more you.

[Arun]

Wayfair. Every style, every home. I'm gonna fix all of them on day one. But the rolling funds are helpful for early stage fund managers because. Because it just helps them create the track record before they go into the institutional rounds.

[Joel Painkle]

Yeah, I think angel list also helps with some of the community building too. Right. Because people know about it. But I think, yeah, you're right. I think if you're just starting out and maybe you had an angel group, you know, that might be a quicker pathway than trying to meet a bunch of LPs, especially during COVID Right, Absolutely.

[Arun]

So a rolling fund is interesting. I love the SPAC model as well. I mean, that is probably creating some kind of a systemic, systemic risk there. But I love the SPAC model because of the liquidity angle. It become brings to the table quite early in the process. The other challenge is how do you expect retail investors to deal with the asymmetric flow of information? That's a philosophical question. And they also are less regulated by the regulators than the traditional funding vehicles, which are institutionalized funding vehicles. So those are all the pros and cons of the model. But in principle I love the SPAC model, maybe a slight variation of it, but I think the fund model I think is quite harsh on. I don't believe in this management fee thing because that should be a better way of incentivizing the fund managers. But at the same time making sure that the LPs feel that the money is going the right direction to the right set of people for the right. I mean I think that is probably, it's, it's something that can change. And by the way, I have a little bit, little bit longer. My board got over it.

[Joel Painkle]

Oh great. Okay.

[Arun]

So just I hadn't let you know because the change came in quite late, so.

[Joel Painkle]

Yeah, no, no worries. That's a good sign. I feel like, I feel like I gotta, I feel like I'm talking to Brad Feld here. You know, you're not tired of me yet, so that's good. No, that's cool. Okay, so that's the future of fund management. And then what you guys pretty much sector acknowledges. It sounded like you talked to a bunch of different sectors and companies. Probably mainly early stage, but open to a couple different key sectors.

[Arun]

So we like to see some, some revenue, some traction. Right. So we are not a deck in a deck investor, if that's what you call early. But early has a very, it's very broad these days.

[Joel Painkle]

Yeah.

[Arun]

So it's very hard to say say stuff. We tend to invest in firms where we know that there is an alignment of thesis with what, what we feel we kind of can contribute to and where there is an opportunity to make money. So those are the two broad themes. But in drilling down into it probably pre series A. Series A is our sweet spot, has been our sweet spot. And one thing I've noticed is we tend to be harsher on fintech deals than the other 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. If healthcare companies, CEOs come in, I often find them finishing the meeting in 45, 50 minutes and leaving. But if it's a fintech firm, it most definitely overruns.

[Joel Painkle]

And you guys only focused on the UK or you guys open to global as well.

[Arun]

We get deals from even the last last 12, 18 months we've been getting deals from us, from Asia, particularly India because, because of Our backgrounds. Yeah, Europe, a lot of them come in. But for some reasons we found very, very, we've just stayed within our comfort zone, largely invested. I mean what I have done is personally and all of us actually have done that with the partnership. So where I feel very comfortable with a particular deal and I want green shows to invest, but the other two partners or one of them is not comfortable. It doesn't go through the ic. I'll put my money, my personal money. Yeah, it's like saying, hey, although you guys didn't agree, I think this is a great investment. I'm going to put it in and in probably years time I'll bring them back to the IC and then see if we can do a deal with them. So that kind of has worked with a couple of firms. So I did it.

[Joel Painkle]

That's conviction too, right? You got, you know, that's part, that's a whole magic and ethos of VC too. It's like, you know what, I, I, this is how I see the world. I know you guys see it differently but hey, I got conviction. So I'm gonna, I'm gonna put it in and you know, talk, talk to me in seven years and we'll see.

[Arun]

With Yielders, I'm, I'm a angel and kind of an insurance. Yeah, we did that with front check and invoice. I, I was an investor and I brought it into the ic. I mean like early on. Gotta know, brought it in again. Gotta know, third time we got lucky and basically we got a check from the IC and I'm sure we, and Nikki AI, I put in my money, it came to the IC final stages. I didn't get due diligence. So I basically said I really love the company, I manage it. But we've not had an opportunity to bring them back to the IC yet.

[Joel Painkle]

Sure.

[Arun]

These things keep happening.

[Joel Painkle]

Have you guys done any stuff in India? I've had some, you know, myself and a few other people have had some challenges with just the vehicles. So I think there used to be, you know, some vehicles that you can use to go in through Mauritius and Singapore, you know, from the U.S. right. But I don't know if you have any inputs on just investing in India or if you guys have and any insights you have.

[Arun]

So we did actually. Can you give me a second? There's quite a lot.

[Joel Painkle]

Yeah, no worries. I can edit that out.

[Arun]

Sorry about that.

[Joel Painkle]

So no, no worries.

[Arun]

You're asking about India. Yes, we did actually see there are quite a lot of challenges in the, in the kind of cross border transactions. All my India deals have been based on the cash I have in India. I just transferred there. So I, I've never managed to do a cross, cross border deal at all so far. I mean we had some challenges in actually doing a cross border deal from the US to the UK and there were a bunch of US investors investing in one of the portfolio company. We had a challenge and we had one Silicon Valley investor as an LP in our fund as well. So there are, there were some challenges. But yeah, I mean from, from an India perspective, I've not gone through any kind of a Mauritius vehicle or anything like that.

[Joel Painkle]

Yeah, the issue I heard with India is just sometimes there's like double taxation, there's like a tax, the taxes get kind of messy. But that's all I heard. I'm still kind of looking into it.

[Arun]

So I hope I don't get in, I don't have the problem because it's, I don't know, I've not, I'm not actually bothered to check with that.

[Joel Painkle]

I haven't, I haven't invested in the uk. So what, what are some complexities or what are some big differences with like the investment vehicles? You know, is it, do you guys do the same typical safes and convertible notes? Is it all the same type of vehicles or are there different things that we need to think about if we want to invest in, you know, UK company?

[Arun]

From an investment vehicle perspective, they're pretty much the same.

[Joel Painkle]

It's all the same.

[Arun]

You have convertibles here, you've got similar style of mezzanine financing options here, but from a flow of capital from a, from a US entity into the uk. I know there are a few challenges because I don't remember off the top of my head so I have to say that, that particular question. But about a couple of years ago again we had an investor investing, trying to invest into Yielders which is a UK based, one of my portfolio companies. Yeah, we had to find some offshore vehicle that will take their monies and invest on their behalf and all that kind of crap. So we had to say okay, no to that because yeah, it was just not worth the message. But apart from that we've not had any major structuring challenges. Money has just come into the fund and it's because it's an FCA regulated vehicle that we've got at least we've just taken the money and the U.S. it's largely the U.S. investors who have to raise the flag saying hey, this may be a problem for us and for Us. Thankfully we've not had that. I don't remember if they transferred monies within the UK and Sterling, I don't know.

[Joel Painkle]

Cool. All right, so Gigi's got a question here, so I'll read it for you. Has your team ever looked into a company in a sector that your industry does not fully cover? If so, how did you and your team pick up the knowledge and make sure you can speak with the founders and I guess have better judgment? So I guess the learning curve, I mean this is probably what you do every day, right? Talking to new companies, doing new stuff. But how do you get through the learning curve?

[Arun]

So Gigi, I keep asking some of my VC friends who I look up to the same question. In fact, I asked someone this question about two weeks back as well. How do you manage to do that? See, there is no perfect answer to this. It's basically by getting into it, doing the due diligence, researching about it, interviewing people that you know who are experts in the space. So about last week sometime we had a firm based in Europe that are providing a particular operational software for cloud, but a specific cloud provider, OpenStack. And I hadn't really dealt with OpenStack in the past. I had dealt with Azure, I know AWS, but I hadn't really looked at OpenStack. So I had to reach out to a bunch of my friends who have done cloud and they know the whole, whole suite of things. And I found out what OpenStack was what the market.

[Kelly Clarkson]

It's Kelly Clarkson here to talk all things Wayfair. The best place to buy furniture, decor and anything else you can think of to create a home you absolutely love. I know when I shop with Wayfair I find options for every style. Whether I'm feeling boho or farmhouse, modern, traditional French country, I can find exactly what I need for my home and more. No matter your style, space, style or budget, shop wayfair.com to make your home way more you.

[Arun]

Wayfair. Every style, every home potential was what the challenges were and it was easy for me to then be sound educated during the due diligence meeting. So it is a learning process for us as well. But the. Which is why I said when, when, when it is a. It is a space that we don't completely understand. The due diligence process is shorter if it is, if it is a space that, that we are experts in. It just is like ruthless on the, on the entrepreneurs. Sometimes I feel bad for them.

[Joel Painkle]

Sure, that was a good one. Okay, so Deji, aside From the instances where you were able to invest in a venture individually, how else can one deal with disagreements with other venture partners? It sounds like you're trying to say, like, if you, I guess maybe what you're saying, Deji, is how do you get alignment with the other venture partners if there's a disagreement? Is that your question?

[Arun]

That's always going to be there, right? So when you get together to make a decision, it's not just in a business context. Even in life, you have the challenge. It's just about how you negotiate with that person and try to make sense. And I think it's more about listening personally. So within the Green Shows team, Deepak is the hardest guy to convince. If he's convinced, just generally means the deal is through. Because he asks all the tough questions, which are the most simplest questions. In most cases, which we forget, we get technical, we get too close to the deals, and we sometimes forget some of the basic questions which are very hard to kind of think about. He's very good at it. So in most cases, I just spend a long time talking to him about the deal, just, just talking about the benefits of the deal. Sometimes whiteboard sessions, asking all the writing, all the concerns, the pros and cons, and balancing them out. And if there are seriously big red flags, understanding what the mitigation factors are. So just basically going through the process of the concern that someone has and why they have it and how we can mitigate those concerns or address those concerns kind of helps. That's the process that you just have to go through that. And once you have done like, I mean, I've done 20 deals with the team, so once you've done like so many deals with these people, you kind of know where they generally come from. So you, even your due diligence process, even before the filtration process, you know, okay, Deepak is not going to sign this off. Let's not just take this to the ic, kill it. Then we go to the next deal. And only when you know that these people are generally going to be comfortable, there may be some point they'll pick, pick here or there. You generally take it to the ic. So it's generally the, the process of working and, and, and it's, it's worked well for us. It's really.

[Joel Painkle]

Do you often turn them, turn their whole view around or are they, are they pretty much like, hey, you know what? This is not something I believe in? Or like, have you been able to kind of, you know, help them, help them just kind of really Uncover where you're coming from.

[Arun]

Yeah, so many of them. Right. So Varnish and I often are quite technical, so we understand the technology aspects of it. And when it gets technically complicated, Deepak struggles a little bit. But Deepak comes from a very serious business background, so he asks all the right questions and you got it.

[Joel Painkle]

You probably have to trend. There's a translation layer. Right. So you got to kind of change the technical speak into maybe what the business problem is and help them understand. Hey, you know, this problem normally takes, you know, three months to do, but hey, this platform does it in two weeks. Right. So I think if you can simplify it on the business side, maybe that helps, I guess.

[Arun]

I think that Gyana Investment was a good example because it was a data science platform. Their algorithm was superior to Google, at least they claimed that at the time. So he wasn't convinced. It feels like, how can someone be superior to Google? And then we had to get a third party process to kind of go through that, their software, their code, and get us a report saying that. I got that, as they said, why they were kind of differentiated because I came from a data background. But for Deepak, it was hard and until we had that report written up, he didn't quite believe. So there are some ways you actually can turn things around and most, most, most people always have. Because you're giving away money and you're managing other people's money, it is even harder than giving away your own money. You've got to be extremely cautious and you have to make sure that other GPs are happy with it.

[Joel Painkle]

Yeah, that's a good point. Yeah. Because I think that is a common practice to hire maybe a data scientist or developer to do like a code audit. Any other experts that you think are good to kind of call out when you're looking at a technology. Besides, more on the technical side, we.

[Arun]

Did look at a tax startup focused on automation of tax. And I don't remember if it was Deepak Upanish. One of them weren't convinced with it. And we had to go through some of the tax experts that we knew. We got actually one guy from HMRC's board to talk to and he basically then said, okay, these are the challenges and these are the opportunities. And the challenges didn't quite sit well with us. So we said, okay, if those are the challenges, we don't want to take those challenges.

[Joel Painkle]

Yeah, that makes sense. So Akirthy has a question. So she's mainly. So I've seen this too. There's a lot of VCs now that are doing, they'll do like an SPV for SpaceX or an SPV for Airbnb. So what are your thoughts on gps? Maybe opening up vehicles for just access to a block of secondaries? Especially with everything that's going on, do you think it's a good idea, worth it or not?

[Arun]

See, I mean the tech, sorry, the VC industry is. It's lot more fuzzier than we all understand. I mean doing deals is not like, yeah, you go to someone, you pitch it and then you just get the check. It's not quite like that. Sure, you've got to be. You have to understand the broader game of how money comes to the VC to invest. And for us we have a bunch of LPs who just not invest through the vehicle, but they would want access to the deal. Sometimes in that case you have to open up that opportunity for them to go invest along with us. So they just rely on our due diligence capability to invest because they don't have the time or the ability to do it. So in that sense you have to be open to those things. Especially young VCs such as us have to be open to those kind of structures. And again, secondaries, I love the process of having secondaries in the private equity space because that just opens up, it just kills the liquidity question. Any firm, like for instance, actually we missed investing into the firm called Capdesk, which is a UK based company that are doing amazingly well in the secondary market. I think that is an excellent development. I think it's going to help the visa industry in a big way.

[Joel Painkle]

I think my opinion on that too, I think what it unlocks too is obviously if you're at the end of your fund, right, if you have a seven year fund and you're already on year seven, Airbnb has an ipo, yet at least you can just get rid of that and return that money back. And then I think on the founder side, some of those early founders, they may want to buy a house or something. They have those options too for early founders as well. So I think that just that liquidity helps. And I think with some of these platforms, you know, there are going to, I think eventually there is going to be like a stock exchange, you know, versus doing it paper based, some type of digital experience to.

[Arun]

I was so hopeful of the ico. I mean now I call it a bubble, but I was so hopeful of the ICO structure primarily for that. But unfortunately what happened was they started focusing too much on the money Making aspect of it rather than the operational efficiency it brings to this or the abilities that it brings to the table and kind of screwed it up. But yeah, that bringing liquidity to the private equity space with the right level of regulations and controls would be just awesome if someone can do it. That's a big market to go after.

[Joel Painkle]

Yeah, I agree. I'm going to open it up for questions. I just want to squeeze in my last question. So what type of life advice do you have? So any kind of key takeaway, looking back on your career or just talking to your mentor maybe from, you know, Brad Feld, you know, as far as what, what we should just take away.

[Arun]

From this conversation, I think personally because the book has been pretty close to my heart. This the second one especially. Yeah, because I started it with, with a view of writing about strategy really so looking at what the immediate term shot. So the book is about how startups can navigate through a crisis. So really strategies, business strategies, what they should be looking about and all that. But it turned, I mean one, one major find or takeaway for me personally has been the mental health aspect of the entrepreneur rather and through the interviews that I did, 50 interviews of some really amazing people, I mean amazing people across the world. And probably the biggest takeaway for me was that 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, personal advisor. Someone has to keep you at the top most. You have to be playing at your best and especially during. And running a startup itself is a crisis. So forget the crisis kind of. You've got to really be at the top of your game for as long as you possibly can. Your communication has to be in the right, in the right context, has to be in the right way. Your decision making has to be really good. I mean I've seen some of the best entrepreneurs I worked with fail at times. It's just so hard. It's not a joke. So mental health actually brings such a major dimension to the table, especially as a startup entrepreneur. So. And I think there needs to be more stories that comes out of some of the bigger names who've been through and Bradfield shared his episodes of depression with me and I think he's done it in the past as well. But it was such a, such a great thing, amazing thing to hear from people like that saying, I've been here, I've been successful life, I've had so many exits. Jerry colonna sits on 120 boards for the guy to say, I've been depressed and talk about it such so openly. Amazing. And he's done a. He's written a book on this reboot. I really recommend you read it. But the point is that I think there needs to be more conversations on mental health of entrepreneurs. There is enough on strategy, there is enough on iq, the technical aspects of running a business. There's so much help you can find. The ecosystem has matured a lot. What it has not matured on is the mental health aspect.

[Joel Painkle]

Sure. Now, that's what I love about doing this show as well. I mean, I try not to be too engineered. Right. I didn't really prepare to have this discussion with you, but when you do that, people end up opening up. So I've had past speakers talk about daddy issues and talk about other challenges that they had in life. And I think that's what humanizes the whole conversation. And that's just more pleasant to hear because it's more real, as opposed to just talking about an investment thesis or talking about the companies you invested in, which I think is good to learn about, too. But I think hearing the story, I think the beauty of it is really the storytelling. And I'm assuming you probably experienced a lot of that when you talked to a lot of the speakers that you did. Where can we find your book? So it's called Navigating the Crisis.

[Arun]

No, no, it's not released yet.

[Joel Painkle]

Oh, it's not. Okay.

[Arun]

To be honest, I'm not even sure if I'm supposed to be talking about in the public domain, but it is what it is. Right? So we've spoken about it now.

[Joel Painkle]

It.

[Arun]

Is coming out in Jan, so keep you posted.

[Joel Painkle]

Yeah, well, we'll just follow your website. You have a website? I think I found it online. So we'll just stay tuned and keep our mouths shut until then. Okay. So we'll see if anybody else has any final questions. I know you probably got to run soon. Anybody else in the room have any questions, you can ping it in the chat, too. All right. Well, hey, Arun, thank you so much for your time. This was awesome and really appreciate it. And we'll catch up soon.

[Arun]

Sure. I'll just type my email IDs.

[Joel Painkle]

Yeah, absolutely.

[Arun]

And feel free to get in touch. Super.

[Kelly Clarkson]

It's Kelly Clarkson here to talk all things Wayfair. The best place to buy furniture, decor, and anything else you can think of to create a home you absolutely love. I know when I shop with Wayfair, I find options for every style, whether I'm feeling Boho or farmhouse modern traditional French country. I can find exactly what I need for my home and more. No matter your space, style or budget. Shopwayfair.com to make your home way more you.

[Arun]

Wayfair Every style, every home.