3. What are some of the lessons that you picked up from your earlier career that make you a better CEO today?

• Move quickly and get comfortable with the uncomfortable. Building a company requires us to make quick decisions with the facts that we have at the time – even if it’s not the full picture.
• Maintain intellectual honesty. We strive to get to the right answer and we’re flexible enough to change our minds. We need to experiment and then analyze the data.
• Be persistent and patient. Not everything works out, but we need to make sure we don’t abandon our efforts too early. It’s a tricky balance that I’m continuing to work on! 
• Have Integrity. Life’s too short to do things that don’t feel right in the interest of a short-term profit.

4. How does Capitalize use technology to disrupt the retirement savings process?

One of the biggest pain points in saving for retirement is doing the right thing with your 401(k) savings when you change jobs. Unfortunately, millions of Americans “cash out” (withdraw) their 401(k)s prematurely, paying taxes and penalties in the process. Millions more leave them behind altogether.

That’s because the process of transferring those assets – known as “rollover” – is manual. We’ve digitized that rollover process, and we help users find and consolidate their old 401(k)s seamlessly so they can better grow their hard-earned savings – for free. We partner with some financial institutions in that process, and we’re excited to keep extending our product.

5. How did you know it was time to take on outside investors and what did you learn in the process of raising your Series A?

We knew early on that we wanted to build scalable technology that helped millions of Americans. To do that, raising venture capital seemed like a good way to grow the company and get the guidance of thoughtful investors in the process.

Before raising any outside money, I self-funded the company for a little under a year. I spent as little money as I could while also finding ways to validate some of the key assumptions behind the business, like whether there was demand for this, what the product could look like, and whether we could build a viable business. Once I felt good about that, I brought an amazing technical co-founder on board and we raised our first round of capital.

We learned several lessons in raising a Series A. Some of them:

• Focus on the investors you want, not on valuation. We’ve always tried to optimize for great investors, rather than the valuation of the company. Having good partners is a long-term benefit and something that pays dividends over time.
• Seek out people who challenge and support you. In finding your investors, try to find a group of people with different perspectives who are unafraid to challenge you. That’s how you’ll grow.

6. What advice would you give someone who’s interested in starting their own company? What would you tell them about fundraising in the current environment?

Starting and growing a company is an incredibly rewarding and thrilling journey. It’ll push you to grow in new ways – as long as you’re ready and excited for it. There are different phases of your life that might be more suited to doing it than others, so be honest with yourself about whether now is the right moment.

In the current fundraising environment, stay focused on finding the right partners and be patient. Be creative about ways to fund the business in the interim and really embrace the “lean” approach to company-building. Stay focused on your mission and on solving a problem, and that will hopefully shine through in your fundraising conversations.

Gaurav, thank you for your time and insights.