Next Gen Spotlight: Gaurav Sharma of Capitalize

December 13, 2023
  • Private Banking
In this Next Gen Spotlight, Relationship Manager Mack Dowling sits down with Gaurav Sharma, founder and CEO of Capitalize, to discuss career lessons and the importance of remaining focused on your mission.

Gaurav Sharma is the founder and CEO of Capitalize, the first online platform to help consumers easily transfer their retirement assets. By coupling proprietary technology with advice from their rollover experts, Capitalize aims to provide a seamless way for people to find, consolidate, and maximize their retirement savings. Before founding Capitalize, Gaurav honed his experience and passion for investing and entrepreneurship in the investment banking and hedge fund industries.

BBH Relationship Manager Mack Dowling recently sat down with Gaurav to discuss his journey to becoming a CEO, lessons learned, and the importance of remaining focused on your mission.

1. You were an investment banking analyst and then worked at a hedge fund before founding a company and becoming the CEO. What inspired you to make those career changes and then decide to go out on your own?

I’ve always been fascinated by finance and how it intersects with our lives. Like many others, I realized that starting off in the investment banking world was a great training ground. It opened many doors for me – one being the opportunity to work at some well-known hedge funds. I was fortunate to work for some amazing people who were generous mentors, and they taught me how to analyze situations, think about risk-reward, and make high-quality decisions with imperfect information.

About a decade into my career, I got the itch to use that knowledge and skill in different ways. I was noticing ways that Americans struggled with financial decisions in their daily lives. One thing led to another, and I set off to build Capitalize to help people better handle their retirement finances.

2. Personal finance can be overwhelming – what inspired you to start Capitalize and what is your company’s mission? How has your mission evolved as the company has grown?

One of the observations I had while working in finance was just how hard it was for most folks to save for retirement.The burden placed on us as individuals to do the right thing is significant – we need to decide how much to save for retirement, which account to save in, how to invest that money, and then how to withdraw it thoughtfully when we retire. These are tough asks for even the savviest financial professional – and yet it’s what millions of Americans are expected to do each day.It’s no wonder, then, that so many Americans enter retirement without enough money saved to live a comfortable life. That always struck me as a problem worth solving, so we started Capitalize with the mission of helping people save and invest for retirement.While our specific products and how we offer them may change over time, that mission will not. It’s what keeps us going.

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.

What’s Left Behind

When you change or leave a job, your 401(k) savings don’t automatically travel with you. Instead, you can either roll the account over into an individual retirement account (IRA), roll over the old 401(k) into a new one (if permitted by your new employer), cash out the old 401(k)’s assets, or leave the money behind. Unfortunately, many Americans tend to put off this decision for later, resulting in scattered 401(k) accounts, unnecessary fees, and even lost savings.

  • As of May 2023, there were an estimated 29.2 million left-behind 401(k) accounts holding approximately $1.65 trillion in assets.1
  • The number of forgotten 401(k)s has increased by over 20% since May 2021 due to heightened job switching.2
  • Two in three Americans don’t know what they’re paying in 401(k) fees.3

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.

Fall in love with a problem rather than a solution. Your actual solution or product offering will evolve, so you want to make sure you’re excited by the problem you’re working on and that’s what will keep you going.

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.

The other piece of advice I usually share is to fall in love with a problem rather than a solution. I’m not the first to give this advice, but it rings true. Your actual solution or product offering will evolve, so you want to make sure you’re excited by the problem you’re working on and that’s what will keep you going.


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.

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Read It

1 Capitalize. The True Cost of Forgotten 401(k) Accounts (2023). 14 June 2023. The True Cost of Forgotten 401(k) Accounts (2023) – Capitalize (hicapitalize.com)
2 Ibid.
3 Capitalize. 401(k) Fee Survey. 9 February 2023. Survey: 2 in 3 Americans are in the dark about their 401(k) fees (hicapitalize.com)

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