Five lessons from my time as an entrepreneur-turned-investor

Rajiv Srivatsa, Investor and Partner at Antler India, candidly shares his learnings from his shift to the other side of the table - from being one of India's most respected founders to now starting his journey as an early-stage Investor

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Truth be told, unlike some of my founder peers, I had not invested in other startups when I was a part of Urban Ladder. It’s been only 6 months since I have actively started evaluating early-stage startups and made some promising investments as part of Antler. Nevertheless, as I start my years in venture capital, I want to reflect on my early learnings that are shaping the way I think about this space, my transition, and how I leverage my experience as a founder to now being an investor.


To begin with, I am thankful to all the founders, angels, and investors who spoke with me when I was making the decision to become an ‘investor’, and shared so many invaluable lessons firsthand. In addition, Nitin Sharma, my ‘co-founder’ at Antler India, has been extremely generous in sharing his insights on early-stage investing from his 12+ years in the VC ecosystem across the USA and India; having worked with multiple unicorn founders, helping companies go to IPO and delivering sizable M&A outcomes. This support has massively accelerated my learning curve.  

On a foundational level, my biggest advantage with Antler is that I am a founder here as well! Setting up a new organization from Day 1 to where we are today, just a year later - at 5 highly promising startup investments, 9 stellar team members, sizable capital raised & partly disbursed, 6500+ founders evaluated over the last 6 months, and several high-impact ecosystem conversations - has been an incredible founder journey in itself, albeit in a new avatar.

The other massive advantage is being able to truly and meaningfully empathize with founders, having personally gone through the good, bad, and ugly of the startup journey. Beyond figuring out some levers of success and early-stage patterns, my prior founding experience gives an astute window into a founder's ambitions, challenges, and what it takes to be on the founding journey.

As I wear the investor hat on top of my founder hat, here are my top five learnings, divided into two buckets.

In the first bucket, I will cover three areas, that as an investor I find different from my time as a founder -

  • Doer vs. Facilitator - Early on, I have come to terms with the fact that I am only a facilitator. I can neither hope to have the depth on customer-thinking, nor the context that the founder has on her own startup. As well-intentioned as my guidance may be, I put an honest caveat on my inputs to founders, telling them I know little and largely from my context as a founder in a different time and mostly a different space. Having said that, as an investor scanning the macro-landscape and long-term trends, I may still be able to guide and answer some of their challenges from a different perspective.
  • Ecosystem maturity - The founders, the VCs, in fact, all aspects of the Indian startup ecosystem have come of age. Just in the last 5 years, there has been a dramatic shift on every front, and not just in terms of the number of players or cheque sizes. Today, 22-year-old founders are sharper and more risk-taking than I was when I decided to start up at the age of 33, almost a decade back! All aspects of the ecosystem are advancing rapidly in lock-step, including know-how, networks, and startup talent, further accelerating the trend of more high-potential founders starting up than ever before.
  • Feedback Loops - In the founder world, we could float an experiment or an A/B test and get feedback, learn, iterate and launch features with very clear signals. In the investor world, true outliers could take over 5 to 10 years to show game-changing outcomes. So there’s no immediate feedback loop available beyond perhaps analyzing startups that have shown some early product-market fit or those who have raised the next round.

In this second bucket, I will talk about the two things that I borrow and carry forward from my time as a founder to, now, my time as an investor -

  • Playing to my strengths - I handled three areas at Urban Ladder - Technology & Product, People & Culture, and Brand & Marketing. I communicate clearly to our founders, right from day 1, that these are the functional areas on which I can provide value. In addition to helping them navigate the tricky ‘sine-wave of a founder's life, both personally and professionally, I am able to focus my conversations and go deeper on these three areas.
  • Humility & Curiosity - One thing that has not changed (and never will) is the ‘Day 1’ mindset I adopt every single day. In today’s time, when practically everyone is becoming an investor and making bold proclamations across social media or other channels in a bid to get attention, I understand and appreciate the value of keeping level-headed. Not getting ruffled, even in the midst of FOMO-inducing news or the hype cycles, and being curious about every founder and every new space, is something that I will always center myself on.

My journey has just begun and there is a long way to go - it has just been the first 6 months. But with the combined learnings of the team around me and the founder mindset that helped create Urban Ladder, I hope to create a meaningful institution in Antler India and help significantly impact hundreds, if not thousands of founder journeys in this decade.

Rajiv Srivatsa

Written By

Rajiv is Partner at Antler, where he is leading the deployment of Antler in India. Rajiv co-founded Urban Ladder, one of India's most beloved omni-channel brands that changed the way Indians shop for furniture online. Over ~8 years, Urban Ladder served more than 1 million customers, grew to 1,000+ employees, and raised over $100Mn in venture capital from top global VCs. Prior to Urban Ladder, Rajiv built cutting-edge products catering to international markets at Yahoo!. He has been featured on GQ Influential Young Indians and the Fortune 40 Under 40 India list. Rajiv loves working with early-stage entrepreneurs on product, culture and brand to build scalable companies.