When I told Adrianna Samaniego that I grew up in Tucson and had family in Agua Prieta, she immediately said, “get out of town.” She grew up in Douglas, Arizona, just across the U.S.-Mexico border from Agua Prieta. There are not too many people in venture who know of the place.
At Cherryrock Capital, Adrianna sees an investment opportunity among founders whose backgrounds may be similarly unfamiliar to other investors. The firm backs underinvested entrepreneurs at Series A and B, when they have built businesses with customers and traction but need larger checks to scale. Many newer venture firms concentrate on the earliest stages. Cherryrock wants to lead the rounds that follow, when a founder needs $10 million or $20 million to expand. I wanted to understand how growing up in Douglas shaped her ability to recognize those founders.
She mentioned her grandfather’s work in a copper mine. I told her that my grandfather had been an electrician in the copper mines of San Manuel. I called him my tata. She used the same word for hers.
Adrianna continued to tell me a story of how her grandparents had immigrated, worked and eventually became business owners. She spent time in their businesses as a child, and never once heard anyone describe what they did as entrepreneurship.
After a mine injury, Adrianna’s grandfather started a plumbing and construction business. Ownership offered a measure of control in a place with limited jobs and few safety nets. Her grandparents wanted something of their own because they couldn’t assume someone else would protect their livelihood.
Today, Adrianna sits across from founders asking questions informed by what she saw growing up. Can this person build a business and keep it going when circumstances become difficult? She expects the people she meets to be smart. She is trying to assess their judgment and ability to scale. How will they handle pressure and stress. And do they ultimately have what it takes to handle the distance between an ambitious plan and the company they actually have to run.
Growing up in Douglas gave her knowledge that has helped understand entire industries. Her family crossed into Mexico for groceries and medical appointments. She grew up speaking English and Spanish, moving between places that were separated politically but connected through the routines of daily life. Now she encounters companies working in what investors call medical tourism. As a child, she understood the same activity as going to Agua Prieta because braces were more affordable there. A market that needed explaining in an investment meeting had been an ordinary part of her upbringing.
At 16, she moved to a high school outside Atlanta. She had been near the top of her class in Douglas, but in the same advanced courses in Georgia, she found herself behind her peers. Nights and weekends became time to catch up. She had known the place she came from offered fewer opportunities; the move made those differences more visible. When she evaluates a founder’s progress now, she wants to understand the conditions under which it was made.
At Series A and B, customers, retention, churn and growth give her something concrete to examine. She pays particular attention to founders who produced those results without the access others had. Their progress can reveal judgment and persistence that a résumé might miss. Investors, she argues, can overlook that evidence when they feel more comfortable backing someone who reminds them of themselves.
I asked her why the opportunity she described remained available. Was it racism, sexism or something else? She said private markets were slow to update their beliefs, then acknowledged that this was the diplomatic way to describe it. Investors were comfortable with what they knew. Familiarity could make a founder seem validated before the business had received enough scrutiny. She had fallen into that trap herself, listening to founders who told a persuasive story and had the expected credentials, then discovering that they lacked the judgment to scale.
I asked why the firm had chosen Series A and B if access to capital was the problem. Someone had presumably already found these founders and written their seed checks. Adrianna’s answer was that many new venture firms had formed around the earliest stages. She had previously worked at Female Founders Fund, which invests early. There were fewer firms focused on underinvested founders that could lead when a company needed $10 million or $20 million to expand.
Cherryrock wanted the ability to write that term sheet, take an ownership stake and become a board partner. It would have to make up its own mind about the founder rather than wait for another firm’s commitment. When evaluating companies and founders, Adrianna prefers a conversation to a long presentation. She wants someone to explain why a customer’s problem persists, what they understand about it and where their own plan could fail. She notices founders who identify their weakest assumption before she finds it.
Her experience can help her understand a problem, but she still has to assess the business built around it. Adrianna grew up on Medicaid. Her grandparents fostered children for decades, and she remembered children she considered cousins struggling to receive appropriate care. When she discussed Cherryrock’s investment in Flourish Health, she brought that history alongside its growth and margins. The company closed a $26 million Series A, she said. She now sits on its founder’s board, helping it scale.
The firm also examines its own decisions. Each year, Cherryrock reviews how companies progressed from first meeting to diligence and term sheet, looking across sectors, gender and race. It records reasons for passing and asks whether bias appears in those reasons. This is the part of Adrianna’s argument that requires more than finding a founder relatable. Her background gives her a view into experiences another investor might miss, however, it does not exempt her judgment from examination.
Toward the end of our conversation, I suggested that founders who built and exited companies might become investors themselves. Adrianna took the thought further. She wanted to track who owned equity, including employees, and who eventually moved to the other side of the table to write checks. She was thinking beyond one fund’s life, toward a different group of people making investment decisions in 20 years.
We started our conversation with two grandfathers who worked in copper mines and the word we both used for them. Adrianna watched hers run a successful business. Today, she puts capital and expertise behind founders she describes as audacity, authenticity and accountability, guided by an understanding of ownership she first learned from her tata.
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