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Rajeev Singh-Molares: “Find a mentor or be one”

As a Hispanic entrepreneur keep a positive attitude. Have faith in yourself and keep going. This is true for any entrepreneur regardless of their background, ethnicity, or race. Find a mentor or be one. I have been advising and working with a Hispanic founder who left Venezuela after having a hard time just putting food on […]

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As a Hispanic entrepreneur keep a positive attitude. Have faith in yourself and keep going. This is true for any entrepreneur regardless of their background, ethnicity, or race.

Find a mentor or be one. I have been advising and working with a Hispanic founder who left Venezuela after having a hard time just putting food on the table. He is bootstrapping in Miami right now and building his company Babelus. Luis Juarez and Babelus are off to a great start with some impressive clients in the portfolio. I think he is going to create something spectacular.


As a part of our series about “Social Impact Investors”, I had the pleasure of interviewing Venture Capitalist Rajeev Singh-Molares.

A graduate of both Yale and Georgetown and former senior executive at Alcatel-Lucent, DHL and consulting firm Monitor Group, Rajeev Singh-Molares has been in venture for six years. His firm’s focus has been on Hispanic entrepreneurs. He’s on many startup boards including Returnly, Clarity AI, NNAISENSE, and RubiconMD.

Singh-Molares was born in Europe, grew up in New York City, and currently resides in Bellevue, Washington. He has a unique cultural background comparable to Vice President Kamala Harris. His late father was from India and his mother is from Spain.


Thank you so much for doing this with us! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

A startup founder needs coaches who will help with their journey. I do this and thoroughly enjoy it.

While I was working with startups during my time at large companies, I realized many founders need a lot of help with the management fundamentals like their ideas, products, people, growth strategies, and to adapt to ever changing environments.

Given my background as an immigrant I have some understanding for what it feels like to have to adapt to a new environment and be flexible. This is especially true for entrepreneurs from minority communities. Immigrants often don’t have access to as many resources or comfort with the venture community. I’m doing my part to alleviate this problem.

Can you share a story with us about the most humorous mistake you made when you were first starting? What lesson or take-away did you learn from that?

I remember a situation where I was convinced the start-up founder would be thrilled to meet me and begging for help.

I recall meeting Eduardo Vilar the Founder and CEO of Returnly for the first time. I was on my way to the Blue Bottle in San Francisco next to the U.S. Mint, a place with a gritty vibe to put it mildly. He asked frankly, “What do you need?” It was not what I expected to hear, but it became the basis for an eventual great working relationship and friendship.

I’ve been on Returnly’s board now for five years: Their customer acquisition growth has been admirable. I consider Vilar a role model for other Hispanics. [Editor’s Note: In April, Affirm Holdings Inc. entered into a definitive agreement to acquire Returnly for total cash and equity consideration of approximately 300 million dollars.]

Just because you are a VC with money and potentially valuable growth advice doesn’t mean you are going to be accepted right away. You need to be patient, respectful and explain your value. Just as an entrepreneur needs to be patient in finding the right VCs.

Are you able to identify a “tipping point” in your career when you started to see success? Did you start doing anything different? Are there takeaways or lessons that others can learn from that?

My tipping points include many personal life adaptations. I often didn’t quite fit in, for example, when I grew up in New York City. I was an Indian-Spanish kid born in Europe. There weren’t many others like me. Because of this, I can imagine what Vice President Harris must have felt like. There were instances when life was scary but I grew more confident over time. My advice is don’t fear the unknown.

None of us are able to achieve success without some help along the way. Is there a particular person or mentor to whom you are grateful who helped get you to where you are? Can you share a story about that?

Four people come to mind. My high school history teacher in New York, Judith Zinser taught me to structure my writing and to communicate clearly.

The late Jesuit Father James Schall, a philosopher, professor and author at Georgetown University had an impact on me. He never lectured: He always asked questions. Father Schall taught me the power of critical thinking.

Professor Gaddis Smith from Yale, who is retired, taught me a lot. I was a teaching assistant in his class. I probably learned more from him than anyone else at Yale. His ability to energize and captivate the class was first rate.

The CEO at one of the companies I worked for was hypercritical in forcing the team to get things done. I learned from that experience to take responsibility. Don’t make excuses. Don’t complain. Just get it done. A good motto for life in general!

You have been blessed with great success in a career path that many have attempted, but eventually gave up on. Do you have any words of advice for others who may want to embark on this career path but are afraid of the prospect of failure?

There are instances when life is scary. But my advice is simply this: Do not fear the unknown. And although it sounds like a Boy Scout motto, I’ll add, be thoughtful and prepared.

Ok, thank you for that. Let’s now jump to the main part of our discussion. The United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This is of course a huge topic. But briefly, can you share a few things that need to be done on a broader societal level to expand VC opportunities for women, minorities, and people of color?

Resources at every level need to be structured for equal access, for example, scholarships.

In society, role models are very important and great mentors can make a world of difference. It’s important that we create role models of success that a minority entrepreneur can truly relate to, for example, a Hispanic can be a positive role model to another Hispanic.

Unfortunately, key innovation hubs like the Silicon Valley are not flush with visible Hispanic entrepreneurs. They are there, but need help in connecting with the right people, developing their ideas, growing them and succeeding.

Investing time, effort and capital in these minority entrepreneurs is something I truly enjoy.

You are a VC who is focused on investments that are making a positive social impact. Can you share with us a bit about the projects and companies you have focused on, and look to focus on in the future?

Three examples of investments that have had a positive social impact are Clarity AI, RubiconMD and Returnly.

Clarity AI, founded by Hispanic female Rebeca Minguela, designs enterprise software for investors to gain better visibility on environmental, social and governance or ESG credentials.

RubiconMD, an eConsult service, democratizes medical expertise by making it easier for primary care physicians to consult with specialists. Gil Addo and Carlos Reines are co-founders of that company.

Returnly, a company that takes the pain point out of ecommerce returns and founded by Hispanic Eduardo Vilar, is another example. By the way, in April Affirm Holdings Inc. entered into a definitive agreement to acquire Returnly for total cash and equity consideration of approximately 300 million dollars.

All three solutions are founded by minorities and offer timely services due to what’s going on in the world. Focusing on the future we plan to invest in more companies like these, ones with timely services run by minority founders.

What you are doing is not very common. Was there an “Aha Moment” that made you decide that you were going to focus on social impact investing? Can you share the story with us?

Being of Indian-Spanish descent, there were not many people like me where I grew up, went to school or worked. My “aha moments” were the many times I needed to adapt to new situations.

Can you share a story with us about your most successful Angel or VC investment? Or an investment that you are most proud of? What was its lesson?

There are many! RubiconMD, created by a black and Hispanic founder, has enormous potential and we invested early in their history. They then went on to receive backing from established firms like Optum, which is a part of UnitedHealthcare, and Deerfield Capital Management. Returnly comes to mind as well: They’ve built up an impressive list of customers including Untuckit and Fanatics.

Can you share a story of an Angel or VC funding failure of yours? What was its lesson?

The lesson learned was to innovate with a keen awareness of what else is out there. Just because you have a good idea doesn’t mean someone else has not already done it or is out-executing you.

Is there a company that you turned down, but now regret? Can you share the story? What lesson did you learn from that story?

There are a few companies we turned down based on pure analysis. The lesson learned as an investor is trust your gut and not just the analytics. The people behind the company matter as much, if not more than the idea.

Super. Here is the main question of this interview. What are your “5 things I need to see before making a VC investment” and why? Please share a story or example for each.

I’m in venture but this advice is for the entrepreneur about how to find the right venture partners. Sometimes it’s not the people who have the big brand names.

  1. Stamina matters. You may have to knock on 50 doors before a pitch is accepted. In the case of entrepreneurs from minority communities it may be more than 50 doors unfortunately.
  2. Just secure the meeting. Persevere to get the meeting and then take it from there. The Blue Bottle meeting with Eduardo of Returnly may not have started with a bang but it eventually became productive. Likewise, I met the founders of RubiconMD in New York’s Soho and we developed a great bond over the years. That’s a health tech startup founded two minority founders, one Hispanic and one black.
  3. As a Hispanic entrepreneur keep a positive attitude. Have faith in yourself and keep going. This is true for any entrepreneur regardless of their background, ethnicity, or race.
  4. Find a mentor or be one. I have been advising and working with a Hispanic founder who left Venezuela after having a hard time just putting food on the table. He is bootstrapping in Miami right now and building his company Babelus. Luis Juarez and Babelus are off to a great start with some impressive clients in the portfolio. I think he is going to create something spectacular.
  5. Relaunch your startup every day. If you started a company, you’re going to encounter setbacks and lots of critics. Bottle the energy you had on launch day and reuse it often. You will get a lot of negative feedback along the way. But usually there is also positive feedback. Trust your gut, listen to your supporters, be humble and overcome the negativity.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

We need to create more powerful networks of Hispanic entrepreneurs across the U.S. There are some emerging groups but nothing quite scaled with powerful role models all working in unison.

If you could tell other young people one thing about why they should consider making a positive impact on our environment or society, like you, what would you tell them?

Give back and don’t wait until you’re successful. Being a role model doesn’t start with great success. It starts with modeling basic behaviors.

We are very blessed that a lot of amazing founders and social impact organizations read this column. Is there a person in the world with whom you’d like to have a private breakfast or lunch with, and why? He or she might just see this. 🙂

Gosh there are so many, but Marc Benioff, the founder of Salesforce, is both a successful entrepreneur and truly committed to social justice. It’s clear that he is passionate about justice, has the courage to act on his convictions, and leads by example. A great role model.

How can our readers follow you online?

My LinkedIn page is https://www.linkedin.com/in/rajeev-singh-molares-3163b72/

My Twitter profile is https://twitter.com/rsmolares

Thank you so much for this. This was very inspirational, and we wish you only continued success!

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