Write the Cheque. Write It Off.
What Raghunandan Taught Me About Mental Prep in Angel Investing
In our last episode, we talked about what it means to move from public markets to private bets — from buying history (stocks) to betting on the future (startups), as Nithin Kamath put it.
This week, we go one step deeper.
Because after the cheque is written… then what?
That’s where this episode starts.
A conversation with Raghunandan G.
For those who don’t know Raghu — he’s been around from the early years of the startup ecosystem. He co-founded TaxiForSure and exited successfully to Ola.
I’ve known him as an angel investor and a backer to founders— he’s backed some exceptional early-stage companies. And now, of course, he’s building again — Zolve just raised $250M in funding.
But none of that changed the core idea he shared with me on The Private Market Show in 2021. It has been close to 4 years but the advice feels like it could have been the conversation from this month in 2025.
“Be mentally prepared for losses before investing.”
It’s not the most glamorous advice.
But it might be the one thing every angel investor needs to hear before they start.
Angel investing isn’t about managing upside.
It’s about managing your mind.
Raghu said it without hesitation:
“If you’re going to obsess over outcomes, this is not the asset class for you.”
You write the cheque.
Then you write it off — mentally.
That doesn’t mean you don’t care. It means you’re not emotionally tied to the outcome.
This is where angel investing becomes more psychology than finance.
Zolve just raised $250M…
And that brings me to a fun contrast.
Imagine investing in a startup.
Then nothing happens for 2 years.
Maybe you think, “It’s okay, small bet.”
You move on.
And then — the founder announces a $250M round, with global headlines, top-tier VCs. That’s Zolve. And that’s why Raghu’s advice holds up.
When you invest, it’s not about certainty.
It’s about staying present without being attached.
What we learnt from the conversation with Raghu:
Emotional Liquidity > Financial Liquidity
Most angels worry about how long they’ll be locked in.
But the real skill? Staying detached while staying involved.No Outcome = No Regret
You should be okay even if the startup shuts down tomorrow.
The value of the investment is in the process, not just the return.Conviction isn’t control
Once you write the cheque, let the founder drive.
Angel investing is not portfolio management. It’s early belief.
Why this matters
We live in a culture of exits, unicorns, and LinkedIn wins.
But most of the real angel journey is invisible.
It’s patience, ambiguity, silence.
And sometimes, a surprise email two years later that reminds you -
belief has a weird way of paying off. This still does not negate the fact that Angel Investing is risky, and does follow the portfolio construct, like in public markets. There can be no single winners - always a winner among others who did not meet your expectation on growth and return.
Key Takeaways
Write the cheque. Write it off.
Help if asked. Don’t hover.
Stay in the game long enough to see the outliers.
Celebrate the ones that win. But don’t measure yourself by the ones that don’t.
This episode reminded me that angel investing, like life, is easier when we’re not overly attached to the outcome — but deeply connected to the intent. We have a lot to learn about ourselves from watching how we work with founders, and other investors.
The Bhagavad Gita puts it like this:
“Karmanye vadhikaraste, Ma phaleshou kadachana.”
You have a right to your actions, but not to the results.
Thanks for reading. Keep learning.
Team LetsUnbox.
