Trish Costello and the business of changing the guest list

Trish Costello calls herself a Kansas farm girl who got lucky. It is an appealingly economical biography for someone whose working life has involved entrepreneurs, government advisers, venture funds and the education of people who decide which businesses get a chance. Luck takes very little credit. Building an institution requires rather more paperwork.

The modest description also contains a useful clue. Costello has been interested in the conditions that let an idea become a company, and in the people who can change those conditions. Her career has moved across the table: entrepreneur, angel investor, educator, founder again. Each position offers a different view of the same transaction. Somebody sees a possibility. Somebody else decides whether to finance it.

At Portfolia, the company she founded in 2014, she has made the second person the subject of the experiment. Women invest together through professionally managed venture funds. They can listen to founders, follow the assessment of a business and bring their own knowledge into the conversation. The arrangement gives Costello's long preoccupation a practical form: more people participating in decisions about what gets built.

A Kansas beginning, without the mythology

Costello was born in Pittsburg, Kansas, and attended Pittsburg State University, where she served as student body president. She earned a bachelor's degree in 1978 and later an MBA in executive management at Rockhurst University. Before the Silicon Valley chapter, there was a record of taking responsibility in places where she already belonged.

Her account of growing up is striking for its lack of a conversion scene. She and her three siblings learned to treat a need as an opportunity. She has described believing, from childhood, that a good idea could be made to happen. That belief leaves plenty of room for mistakes; it simply assumes that action is available. An obstacle becomes something to work on rather than an instruction to stop.

Her early career included developing small business products and marketing strategies at AT&T. Later, she would direct Babson College's Arthur M. Blank Center for Entrepreneurship. Corporate work and entrepreneurial education might appear to occupy different worlds. Both ask someone to understand a customer, organize resources and make a proposition clear enough for other people to use.

There is something useful about a founder who has spent time around the machinery. The elegant idea still has to survive meetings, budgets and a Monday morning. Costello's route into investing began with experience as a venture-backed entrepreneur and then an angel investor. She had encountered capital as something a business needed before she began studying the people entrusted with allocating it.

Teaching the people who write the checks

In the 1990s, Costello helped create Kauffman Fellows at the Kauffman Foundation and became its first CEO. The program developed a way to educate and connect venture capital professionals. She remains its CEO Emeritus. Here, the object of her work was unusually indirect: help an investor improve, and that person's judgment can affect many entrepreneurs afterward.

The work was institutional as well as educational. Phil Wickham's account of the program's history places Costello and founding chairman Jason Green at the center of the leadership behind its move toward an independent Center for Venture Education. Building a curriculum was one task. Giving that curriculum an organization capable of continuing was another.

Costello also became the founding president of CVE Capital Corp, the holding company associated with a venture capital fund of funds. The connection between education and funding was deliberate: financial infrastructure could support the program's future. Her career repeatedly returns to this sort of construction, where the enduring result depends on a system rather than a single persuasive speech.

Women were part of that educational effort. More than a quarter of the fellows were women in the period examined in a 2020 case study of Portfolia. Yet Costello came to question how much those placements changed the wider industry. Getting capable people through the door could leave them working inside a culture whose assumptions they had little authority to change.

That is the tension at the heart of her next move. A training program can give someone expertise, confidence and connections. It cannot automatically give a junior investor control over a firm's priorities. The invitation and the agenda are separate things. Costello had helped improve the invitation. She began looking for a way to change who owned the agenda.

A fund with room for its investors

Portfolia carried the educational impulse into a different structure. Its members could invest in a portfolio of private companies while observing the work of experienced investment partners. The company offered access to pitch calls and diligence, with participation shaped around how much time an investor wanted to give. A busy person could remain an investor without acquiring a second full-time occupation.

The choice matters. Venture investing is often described through a moment of judgment: a founder pitches, an investor answers. Portfolia makes more of the surrounding process visible. What questions were asked? What did the team need to establish? Where did an experienced partner hesitate? Watching those decisions develop is a more useful education than receiving a polished explanation after everything has been settled.

“We’re backing companies where women make markets,” Costello said in 2019. The phrase gives the model its commercial logic. Knowing a market includes understanding how people choose, spend, recommend and reject. Someone whose professional or consumer experience illuminates those decisions brings information that a spreadsheet alone cannot supply.

The investor's contribution can therefore extend beyond money. Industry knowledge can sharpen a question. A connection can open a conversation. Familiarity with a customer can expose a weak assumption. None of those contributions removes the need to assess a business carefully. They give the assessment more material to work with, provided someone is willing to listen.

Costello discussed the structure at the SEC's Small Business Forum in April 2024. She described using a 2018 regulatory change that allowed a larger number of limited partners in certain small venture funds. It is an appropriately unromantic detail in a story about participation. A broad ambition eventually encounters a rule about how many people may sign up. The details decide whether the ambition has somewhere to live.

Experience gets a seat at the table

There is also a quiet challenge to the industry's preferred image of a founder. In a 2021 conversation, Costello described valuing experience, networks and resilience, with the entrepreneurs in her portfolio averaging their early forties at the time. The young prodigy could still receive a hearing. Years spent learning a trade could receive one too.

That preference fits her broader argument about whose knowledge counts. A person who has worked through several rounds of difficulty may have noticed problems that an outsider never sees. Experience is not an automatic qualification, but it is evidence worth examining. Novelty has an excellent publicist. Familiarity with a stubborn problem often has to introduce itself.

The company's investments include Madison Reed, Canela Media and GrubMarket. The list makes clear that Portfolia's interests reach across consumer businesses, media and other markets. Costello's work also includes sustainability and companies serving communities that conventional venture investors may overlook. The common thread is an interest in demand that becomes clearer when different people are doing the looking.

Her geographical experience supports that instinct. She spent years in Kansas City before building her Bay Area career. She also helped conceptualize the initial format of Kansas's PIPELINE entrepreneurial fellowship as an entrepreneur in residence. It is a reminder that her interest in connecting talent and resources did not begin or end within driving distance of Sand Hill Road.

At Babson's 2009 Entrepreneurial Energy Expo, she was scheduled to lead a conversation about green entrepreneurs and startup exits. The subject puts another piece of her career in view: an interest in what happens between an idea and a durable business outcome. Identifying an opportunity is the opening move. Getting a company built, financed and carried forward is the work that follows.

“Create your own rules.”

Trish Costello · March 2026

The mentor keeps showing up

Costello's public record contains a quieter kind of continuity alongside the funds and fellowships. In March 2023, she joined a five-person SHE-CAN mentor team supporting a young woman scholar from Cambodia in pursuing a US college education. She also served on the Motley Fool Foundation's board from 2021 to 2023 and has volunteered with the Mill Valley Art Festival.

These activities have different purposes, but they show a person willing to spend time inside the practical arrangements of a community. Mentoring is rarely dramatic on a calendar. It involves returning to a conversation, remembering what someone needs and helping with the next step. It suits a career in which teaching has kept reappearing, even as the audience has changed.

There is playfulness in her descriptions of the job, too. Asked about her life in venture, she once likened herself to someone on the bridge of Star Trek facing a difficult challenge. The comparison is cheerful without making the work sound effortless. A bridge is a place for a crew, instruments, decisions and the occasional alarm. Investors may prefer more dignified metaphors. This one at least makes room for other people.

The emphasis on company also runs through her public conversations about investing. At a 2017 women investors' forum, she spoke about the gathering and its lessons. In a 2022 podcast, the discussion returned to how Portfolia was designed and how a fund participant could learn within it. Across those settings, the educational question persists: how does someone move from interest to informed participation?

The guest list becomes the agenda

In March 2026, Costello urged her audience to “Create your own rules.” Her accompanying message pointed to thousands of women investing and contributing value to companies. The language was consistent with the decision she had made years earlier: use the skills people already possess to build an arrangement in which those skills matter.

By October 2026, Portfolia's website described a community of more than 2,200 women investors across 48 US states and 20 countries. Those are the company's reported figures, a measure of the reach of the community she set out to assemble. The venture has taken an idea about participation and given it a meeting schedule, investment partners and a membership spread beyond one region.

Costello's story offers an unusually concrete way to think about power. It can sit in the curriculum that prepares an investor, the fund structure that admits a participant, or the questions that make a founder's market legible. Each changes a small part of the decision. Together, they can change who is heard before the check is written.

The Kansas farm girl has spent much of her career organizing that conversation. Her next chapter remains tied to the same aspiration: women using capital, knowledge and connections to back companies they want to see succeed. There is no shortage of occasions to invite people into a room. Costello has made a business out of giving them something consequential to do when they arrive.