Why I Stopped Trying to “Break into VC” and Instead Began Looking For My Tribe

After Years of Failing, It’s Time for a New Strategy

The year was 2010, and I was about to graduate with my engineering degree from Columbia University. As commencement loomed closer, I was nervous about life after turning the tassel. A week before finals, I received a manila envelope in my mailbox. It was from my Mom, and written at the top in her impeccable penmanship was, “Reach for the stars! Your grandfather would be proud.” Opening it, I pulled out an old, worn-out, and discolored copy of what looked like a product brochure. It was from my grandfather’s business called Moreno Products circa 1950, and below is a copy of what the front page looked like.

It included marketing information in both English and Spanish to appeal to a larger audience. In it, my grandfather mentions his experience as a Navy veteran and how his background as a mechanic led to his innovation.

I’m not sure what became of the business, but it was a morale boost going into the last few days of college. I love looking at that brochure, specifically seeing part of my name: Moreno. It reminds me that dream chasing runs through my blood.

For years my Mother told me stories about her dad, a mythical man I never met as he died before I was born. What my Mother neglects to mention (and what I can’t see from this brochure) is how many times my grandfather attempted and failed to get his business off the ground. Perhaps the turning point came when he realized that he needed to add his own unique touch and style to separate his business from the rest. The business name, the story, marketing the product in both English and Spanish: these nuances differentiated Moreno Products from the competition.

My grandfather put himself into every aspect of his business, and that is what led to his success.

Like my grandfather, I too am a dream chaser. For the past five years, I’ve been focused on earning my spot in the elusive venture capital (VC) community, a business that involves finance, technology, teamwork, and investing in people with ideas. Since 2013, I’ve worked for two startups, interned for two investment teams, volunteered my time researching market opportunities for investors and founders, and have continued building my network and finding ways to develop skills valuable to VCs. I thought this is what it took to work in this field.

For five years I’ve submitted applications for various VC positions, and for five years I’ve failed.

I’ve been close. My interview experiences have included Skype meetings, phone calls, and even one 2 hour due diligence presentation. But “close” is the difference between making the last second shot and missing it. “Close” is the difference between success and failure.

I don’t want to be “close” anymore, I want to belong.

I’ve been told by many of my friends that I don’t have the right background or skillset to do this line of work. When I speak to them about venture capital and the next opportunity I’m applying for, I see their eyes glaze over either out of boredom or sadness. These looks send me the same message time and time again: Why can’t you get it through your skull? You’re too old with the wrong professional background. You’ll be so much happier when you stop chasing this silly dream and just enjoy life. Perhaps this goal of working in venture capital really is too extreme.

There is a difference between a dream and a fairy tale. I’ve learned fairy tales enter the mind sporadically, but dreams haunt until action is taken. At some point, the unabashed gall of dreams requires one of two responses: give up or go for it.

There is one caveat to chasing the dream: while consistent effort may be valiant, there is no straight line to making the dream a reality. There are twists and turns, bumps and bruises. The key is to keep revisiting the game plan, and be open to finding inspiration and new ideas. A month ago, I had just the experience I needed.

My Jerry Maguire Moment

In 1996, the movie Jerry Maguire was released. It’s a story about a sports agent on the precipice of a mid-life crisis, uncertain about both his professional and personal life. The main character is unhappy with his work and downtrodden about the prospects of what the future holds. In an act of defiance against the nature of what his profession had become, he writes a mission statement.

The mission statement was a new business strategy that focused to a greater extent on relationships rather than transactions. For those who haven’t seen this movie (I don’t want to give it away), let’s just say some of his colleagues appreciated his vision and others wrote him off.

“I wrote, and wrote, and wrote, and I’m not even a writer”

It’s hard sometimes to be bold. When we choose to take chances, we accept that not everyone will like our decisions and that we may significantly lower our prospects (or Facebook friend count). From that leap of faith though, we have a chance to find out who we are, of what we’re made, and for what we yearn.

A month ago, I had a phone call with an investor about her work in venture capital. I planned for the conversation similarly to other calls I’ve had, complete with detailed notes about the firm’s investment portfolio, the topics I wanted to discuss, and a final ask to close out 30 minutes, the allotted time most investors offer. As many entrepreneurs can attest to, sometimes expectations fall short of the mark, while others are blown out of the water. This call was an example of the latter.

It did not go as planned. Instead of asking about market trends or which startups I followed, she was more interested in my life story. Why did I want to be involved in venture capital? What motivated me to keep pursuing a goal that had been just out of reach for five years? What did I hope to accomplish in my personal and professional life? Why am I the way that I am?

My half-hour window for questions blossomed to an hour long discussion between two passionate individuals. My set of prepared questions had been tossed aside. This was not a transactional conversation but rather the start to a relationship. We laughed, shared startup experiences, and developed a sense of camaraderie. I felt comfortable sharing that I’d been attempting to “break into VC” for years. She made a very simple suggestion:

Don’t put so much emphasis on your skills, but rather focus on your gifts.

The advice hit me like a bolt of lightning. I needed a“mission statement”, a new strategy focused on my gifts.

Perhaps the reason I have not been successful in my VC search thus far is because I am trying to fit a mold, rather than embrace the contours of my professional background. I’m not a former investment banker or have an MBA degree. I can take Coursera classes and read books on financial modeling (which I’ve done), but my self-learning won’t stand up to a candidate who has three years of professional experience.

If I continue attempting to stand out on skills alone, the odds of earning my spot in the VC community are slim and none. I would need to compete on another level. Like my grandfather’s approach to his business, I would need to put every aspect of myself into this journey.

A Bold Alternative

Considering that I only have a handful of followers on Medium, I’ve decided to use my anonymity as leverage for speaking my mind. Venture capital, at the end of the day, is about people and relationships. If relationships cannot be built, deals cannot be made and returns will not materialize. Even if an investment opportunity is huge, a shaky relationship can lead to dysfunction.

The same can be said for VC professionals. Most firms are small, so the ability to connect with fellow teammates and develop relationships is imperative to success. Relationships are formed through mutual values and trust over time.

If the aforementioned statement makes sense, then the idea of “breaking into VC” is ill-advised. When a friend visits me, I don’t let him/her “break into” my house. My friend is welcomed inside because of the relationship developed. The same perspective should apply to the job search; a relationship with the VC needs to be established first. How do we establish relationships? Through mutual values.

My Break Through: Stop Trying to Break In

Remember that investor I mentioned earlier, the one who gave me an hour of her time? She has become a great mentor, and our conversations since have given me much to chew on. If venture capital is a business based on relationships and mutual values, then the first question that should be addressed in the VC search is: what are my values? If I know my values and can articulate them to others, then I can pinpoint those investors who share them and would be interested in building a relationship. My VC career strategy going forward is to “focus on my gifts”: staying true to who I am, speaking about my values openly, and reaching out to those investors who share them. In essence, I’m looking for my tribe.

As a first step in this new strategy, the following sections outline some of my key values.

GQ

One character trait that all entrepreneurs have is either high IQ or EQ. GQ (grit quotient) is a relatively new term, and has been getting more notoriety lately. GQ is made up of three components: hustle, elasticity, and vulnerability. I place them in that order because that is the process of how we learn from our experiences.

For example: for the past five years I’ve been working to earn a spot in the VC community, applying to jobs all over the country (hustle). I’ve been rejected more times than I care to remember. Nevertheless, I dust myself off and keep working on this goal, bouncing back from my failures (elasticity). I’m not afraid to admit my mistakes, as long as I learn from them (vulnerability).

Turn off the television, and get to work.

My tribe will consist of entrepreneurs and founders with high GQ. They are not afraid of admitting mishaps, and rise strong with greater knowledge and persistence. Brené Brown in her book Rising Strong has another term I like: “badassery.” My tribe is badass.

Equal Access to Venture Funding for All (including former Mariachis)

Entrepreneurs by nature are disruptors, and venture capitalists invest in startups focused on upsetting ecosystems that may be antiquated or inefficient. What is ironic is that the business of venture capital itself may be a bit old-fashioned.

While these numbers are changing, the vast majority of venture capital money is invested into a single demographic. As VCs are expert pattern matchers, it makes sense to bet large on the demographic with the best track record. However, is it possible there are business ideas with enormous potential that haven’t been tapped because the founders don’t fit the pattern? I think so.

My tribe is willing to look for those founders who can generate multiples from an early-stage investment, regardless of what they look like. They will search those areas where there is no pattern, and find those entrepreneurs who will become pattern makers. My tribe is visionary.

Multipliers

I read Fortune’s “The Broadsheet” daily newsletter about the world’s most powerful women and came across the professor and author Liz Wiseman and her book Multipliers. The premise of the book is the best leaders are not always geniuses, but genius makers; they make everyone else around them better.

Multipliers are hellbent on improving their team as a whole; someone may come in with “B” level skills, and multipliers turn those individuals into “A+” professionals. Multipliers liberate people from their own professional insecurities; they listen aggressively, and invest time and energy to create a deep level of trust. They guide when needed, but instead of providing the answer directly, they allow the answer to be found.

My tribe is full of multipliers. My tribe knows the success of the group is predicated on the efficiency of the team to share their knowledge; the faster they can learn, the more effective their investment making prowess. My tribe respects everyone’s intelligence.

The Whole Is Greater than the Sum of Its Parts

When I join my tribe, I want them to know who I am, what I believe in, and what I stand for. I do not wish to boxed in and identified solely by my professional endeavors. My moral compass is guided by my personal values, which can be summed up by the following themes:

Faith: I am a man of faith and believe the Almighty has a master plan. While I have not been successful yet meeting my professional expectations, I believe that His plan for me will become apparent soon.

Family: I was once asked if I ever became a wealthy startup founder what I would do with my money. The first thing I thought of was creating an education fund for my family. Not all members of my family have been fortunate enough to go to school, and I believe it would be a beautiful blessing to offer an undergraduate education to them free of charge with the goal they would help replenish the fund after graduation. Creating wealth is one thing, changing people’s perspective can create lasting impact.

Conclusion

More than sixty years after my grandfather started his business, I too am looking to change my stars. Earl Nightingale once said, “success is the progressive realization of a worthy ideal.” Pursuing venture capital within my tribe is worthy. One day I will be successful and find my place. When that day comes, I will hang the product brochure from my grandfather’s business up as a reminder of what it takes to be successful: stay hungry, stay humble, and stay true to your values.

I hope you have enjoyed this thought piece and if you’ve made it this far, I appreciate your willingness to share your time. If you’d like to get in touch, please follow me on Twitter @SerranoVentures. Thank you again.

Updated 2/1/2021:

I had been asked to provide an update since I first wrote this story in 2018. Please find the link to the update here.

I am now working as a Venture Scout with Vamos Ventures, a Los Angeles-based venture capital firm focused on early-stage companies. If you would like to learn more, I would be happy to share. Please reach out to mavila@serranoventures.com. Thank you!

Venture Scout with @VamosVentures, engineer, entrepreneur, investor, marathon runner, and founding member of Mariachi Serrano. Former: @joinrbl1, @fissionvc

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