From the Hood to Launching a Fund: Persistence Overcomes Resistance

Hi there! You’ve likely landed on this page because you heard that, along with my co-founder Jesse Middleton, I launched a venture capital fund called The Community Fund. You’re likely wondering “what is this fund about and who is Lolita Taub?” Well, the short of it is that through the fund, we’ll invest in community-driven companies destined to become unicorns through an investment team, taking a page from XFactor’s playbook.

As for me, I’m an unlikely VC fund manager. Yes, I have fourteen years of experience as an operator and investor in tech corporations, startups, and VC that equate to over $50M in sales and 38 angel and VC investments. But I’m also a Latina who grew up in the hood, survived cancer, and entered my professional career without the advantages of many. At the end of it, though, community, perseverance, and Twitter led me to launch a fund.

If you’re interested to learn more about Jesse’s and my vision for The Community Fund, the investment partner team, and our thesis around achieving outsized returns, you can read that here.

If you want to learn more about my personal story, it’s below. I’ll admit it was hard to write, but I’m sharing it because I see the value of you knowing who I am as a human and then joining me on a journey to move the needle. Once you read the post, I’d like you to ask yourself the Marie Kondo question: does this spark joy? If it does, I invite you to learn more and apply to join The Community Fund’s investment partner team and keep an eye out for when we start looking at startups for investment.

Multiple worlds and communities

My story starts with my feet in multiple worlds. I grew up in South Central LA and my first home was a garage that my dad turned into a one-bedroom apartment. If you’ve watched Straight Outta Compton, then you know exactly how I grew up: the hood. The difference is that my parents shielded me from joining a gang — but I was courted by one for sure and I had a nickname of Panda (I loved panda-shaped ice-cream pops). I had teachers who supported me. One actually paid for my first computer, which my parents repaid in installments because, otherwise, I would’ve never had a personal computer. And that computer was where I fell in love with tech. Another teacher encouraged me to apply to Phillips Academy, a boarding school in Massachusetts, and I got in and went on scholarship. I left South Central to live in New England with a community that represented a microcosm of the elite world. My mom was struggling in LA, counting dimes and nickels to buy a gallon of milk, and then there I was in Andover, going to a school where royalty attended and friends took trips to New York on private jets to get tans.

South Central Los Angeles. Mom and me.

This dichotomy of haves and have-nots was apparent and it boggled my mind that there was such an abundance of resources in my new community but not at home. Ever since then, I’ve wanted to establish a connection between the abundance of resources in the world and the communities that need them. And that desire has never left me because I was always taught to serve my community and family through servant leadership. There was that and the fact that my family’s and community’s economic disposition served as a reminder of the have-nots.

Community: We had an avocado tree in our backyard and when it was avocado season my dad would get empty paint buckets and fill them up with avocados for us and the community to eat. I would go door-to-door sharing our avocados with our neighbors who were grateful. Our neighbors did the same; when we didn’t have food, others would share theirs with us. Community, I learned, was important to survive and thrive. The community was something to take care of.

I was fortunate to graduate from college and land a good corporate job, which allowed me to help support my family after my dad died during the last economic downturn. That happened at the age of 23. It was really hard. I didn’t just lose my dad and have to help take care of my mom and my two younger siblings, but I was also diagnosed with pre-stage cancer. It was a rough time and I was just focused on surviving. Thankfully, through treatment, I defeated the looming threat of cancer.

It was around that time that I sat with my therapist (that thankfully my corporate job afforded me), and she asked me, “what makes you happy?” I couldn’t think of an answer outside of, “rocky road ice-cream from Thrifty.” I broke down into tears. My therapist told me it was okay and to spend some time thinking about it.

I reflected and the thought that kept coming back was, “wow, there is a world full of resources but yet there are those of us that don’t have nearly enough.” I couldn’t afford my family’s mortgage and two car payments, nor could they, and so we lost the house and one of the cars. I knew I needed to make more money.

So, I leaned into my job in corporate tech sales at IBM, and a couple of years later, I had the opportunity to do some soul searching through a project I worked on where I interviewed over a hundred female millennial entrepreneurs for the F SHOW and shared the interviews on YouTube. That gave me joy because after watching my videos, women were inspired to start their own businesses.

Community: I lost touch with any semblance of community when my dad died and I had to step up and do nothing but work to make money. But I always felt the need to create and be part of one. In retrospect, I believe that I used The F SHOW to find a community to belong to and serve. It happened. The women I interviewed for the show became my friends and community. And they set me up for entry into the startup-VC community.

That project led me to a role working for a female millennial CEO in Silicon Valley. That opportunity opened up my eyes to startups, venture capital, and unicorns (billion-dollar companies). And I thought, “this is the world I want to be in, where I could make a lot of money and where others make a lot of money, too.” The problem was, as my CEO pointed out, it was really hard for underestimated founders who weren’t white guys who dropped out of Harvard to raise money and that the check writers were of a similar demographic. There weren’t a lot of investors that looked like me: Latina, 5-foot ¼-inch tall, and the daughter of poor immigrant farmers.

Breaking into VC

That put me on track to thinking: as a businesswoman of color, I want to serve my community and I see opportunity in founders that the industry overlooks which would otherwise produce outsized returns. I need to become a check-writer and invest in underestimated founders. I kept working because I needed to pay the bills but I started thinking about how I could break into venture capital. As I did my research, I was told that I didn’t have the background for a VC because I didn’t know the business, came from no money, and had no connections. It was going to be really hard to break in unless I somehow proved myself to the VC world. So, I took a big financial risk and went back for my MBA so that I could prove that I had the finance and business skills to do the job.

The MBA program was hard because when I arrived and told my peers I wanted to be a VC, they told me that they didn’t think I was suited to be a venture capitalist. One, in particular, told me, “you’re better suited to be a soccer mom.” That reminded me of what many had told me before: Silicon Valley, as is, is not made for someone like me — a person with no connections or capital. But I didn’t let that deter me because of the determination of my parents.

Nothing deterred my mom and dad from leaving their farms and families in Mexico — not having any money, not knowing English, or not even having an elementary school education. Nothing deterred them from their dream to immigrate to the US to give their children a shot at the American dream. And I wasn’t about to let naysayers deter me from pursuing my dream. So, I didn’t. I pushed and persisted and I landed my first VC job in Madrid at K Fund.

Dublin, Ireland. InspireFest 2018. The Backstage Crew: Brittany Davis, me, Christie Pitts, and Arlan Hamilton.

When I came back to the US, it was a struggle to find a VC job, and I had to consult to pay the bills. But, I didn’t give up and eventually landed a job at Backstage Capital. That was a turning point for me because Arlan Hamilton, the Founder and Managing Partner, became my role model. Talk about not fitting the VC stereotype: she didn’t wear a Patagonia vest, go to Harvard, or anything like that. And she too struggled, but persisted and became a VC. Arlan, breaking the mold in the space and believing in me, empowered me to lean more into myself. As Backstage shifted its focus to an accelerator program, I started to look for another venture capital role with Arlan’s support.

Community: Arlan Hamilton and the Backstage Capital Crew welcomed me and reminded me of my roots: supporting, growing, and succeeding in community. At Backstage, we built a powerful network across the world, positioning underestimated founders for success in the global marketplace through the fund and the accelerator. This experience solidified one thing: supporting our community, of underestimated founders and investors, was going to always be part of how I approach things.

Operating and Investing

I met with a lot of VC funds and again I was faced with a lot of, “you don’t have the background for this VC investment role,” and where I did find a good fit (where the firm saw investment in pre-seed and seed underestimated founders as a business opportunity), the salary was going to be so little that I couldn’t pay the bills. At the same time, a VC and college friend introduced me to one of her tech portfolio cos, and I went to work at Catalyte, a company that aligns with my mission of enabling diversity in tech. I embraced being an operator because, truth be told, while I like funding great companies, I also enjoy rolling-up-my sleeves and getting to build — especially when the company is in tech, about profit, and serving the community. Since then, I’ve fallen in love with it and I plan to be there for a long time.

Source: Twitter

But I never stopped thinking of my venture capital dream. I continued to hustle beyond my day job — angel investing, serving the startup ecosystem, and becoming an Indie.vc scout and a NextGen Venture Partner. And then COVID hit and my pay was cut, and that pushed me to do even more hustling and side-hustling. I began publishing a bi-weekly Substack newsletter, online courses, and consulting, and it pushed me to ask myself how I could add more value to the community of underestimated founders and investors that I had started to meet on Twitter.

Tweeting

Source: Twittter

From all of that, I published a couple of tweets that got a lot of attention from both founders and VCs. One involved a call to action for all active investors to share their investment criteria for founders to find them. Another asked underestimated founders to pitch their companies in a thread. With my husband, Josh, I launched the Startup-Investor Matching Tool, which connects underestimated founders with investors.

At the same time, I was riding an emotional roller-coaster because of what happened with George Floyd and standing up for our community — in terms of being underserved, marginalized, and underestimated. I became even more obsessed with how to increase the dollars going to underestimated founders and increasing the number of investors from underestimated backgrounds.

Source: Twitter

And somehow — call it the universe responding to my obsession to make the community better, create opportunity, and serve — a VC partner, Jesse Middleton, at Flybridge reached out over DM and said they were working on creating a fund that would allow me — and others like me — to increase and empower underestimated investors to write checks. The goal was to recruit a team of investors to write checks to underestimated founders because of the opportunity to make outsized returns given underestimated founders are a blind spot for many VC firms. Jesse asked me if I wanted to co-found the fund and build out an investment team. My answer was an emphatic, “sign-me up!”

Launching a fund

So, now here I am: I have an operator role and I have a fund to co-lead. I’m grateful that I can do both because to me that’s my ideal. In fact, Arlan recently asked me what I wanted to do in 2021, and my answer was and continues to be: work toward my personal mission of leading sales at Catalyte and investing out of The Community Fund. And it’s happening!

The moral of the story is that the combination of community and persistence is unmatched. I now have an opportunity to live out my dream of increasing dollars going to underestimated founders through our fund (and through Indie.vc, where I will continue to funnel founders who fit their specific criteria). I also get to recruit the best of the best, up-and-coming investors — and I know that many (if not all) of them will come from underestimated backgrounds.

The struggle is real, no doubt, but we must push forward and continuously ask ourselves what we can do from where we are. We must never give up on our dreams. Our minds are powerful, and what we put out to the universe may just come back to us, as it has for me.

I’m so grateful and I want to pay it forward, not only because it’s the right thing to do in serving our community, but because I believe that when you give you get. I believe in abundance — I’ve seen it — and I do want to create generational wealth, and I do want to continue to support my family (especially as my mom ages and her health deteriorates and my siblings find their way out of the nest).

Call to action

I invite you to ask yourself, “what do I want to do with my life?” It doesn’t have to be startups or venture capital, but I recommend you be intentional in the goals you set because you deserve it and we only live one life.

Source: Twitter

And then, if venture capital is something that’s interesting to you, and reading this post has you pumped, I want you to learn more about The Community Fund and then submit your details here because I am recruiting investment partners for my venture capital fund.

— @lolitataub

P.S. At The Community Fund we invest in pre-seed and seed community-driven companies. And I really want the investment partner community we build to be full of trailblazers, full of hustlers who care about making returns for the fund, who care about creating generational wealth, and also care about making a huge impact in changing the status quo — shifting the needle not just for ourselves and our communities but also opening the doors for those who come after us.

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Also, here are some other ways I can help and you can reach me at @lolitataub.

About Lolita Taub

Lolita Taub is the Co-Founder and General Partner at The Community Fund and acting interim Head of Sales at Catalyte. She is a first-generation Latinx operator and investor pushing for diversity in tech. With 15 years working within the Silicon Valley ecosystem, she has accomplished +$50 million in sales and made 38 investments as an angel investor and VC at Backstage Capital. Lolita is also a Co-Founder of the Startup-Investor Matching Tool, a scout at Indie.vc, Venture Partner at NextGen Venture Partners, and an LP at Operators Collective. Forbes, Inc, and Entrepreneur have featured her as a women in tech promoting diversity. She has a BA from the University of Southern California and an MBA from the IE Business School. Most importantly, she is a dog mom to the cutest Dachshund mix, Choco.

From the Hood to Launching a Fund was originally published in The Community Fund on Medium, where people are continuing the conversation by highlighting and responding to this story.

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