5-1/2 Questions for Trish Costello

CJ Cornell
9 min readJun 2, 2022

Trish Costello
Founder and CEO of Portfolia

Trish Costello is founder and CEO of Portfolia, the leading venture investing platform designed for women. Trish founded Portfolia with a vision to activate the capital of women to invest in the companies we want in the world. Portfolia now has 13 funds and has made 92 investments in 66 top innovative companies.

Trish is globally recognized for her pioneering work in preparing the next generation of general partners in venture capital. As the co-founder, long-time CEO and now CEO Emeritus of the Kauffman Fellows Program, the premier global leadership program for venture capitalists, she mentored hundreds of the world’s top VCs, and was referred to as the venture capitalist’s ‘godmother.’ She also served as Founding President of CVE Capital Corp, the holding company of a $1B+ venture capital fund of funds. Trish was on the start-up team of the Kauffman Foundation’s entrepreneurship center, led the Commercialization Sub-Committee of the National Science Foundation, and directed the Arthur Blank Center for Entrepreneurship at the globally-ranked Babson College.

Trish was recently recognized by INC. Magazine in its 15 Most Innovative Women Entrepreneurs of 2016; 17 Women Investors to Watch by the Center for Women and Wealth, and highlighted in Newsweek, Inc and Forbes for her work in activating women investors.

Trish’s lifelong passion has been in two areas: supporting and investing in innovative entrepreneurs and unlocking the personal and professional talents of women. She knows that women will be both highly successful entrepreneurial investors and bring along an entrepreneurial renaissance when they back the companies they want in the marketplace.

Portfoila — Investing Funds Designed for Women

Trish Costello — CEO of Portfolia

5-1/2 Questions for Trish Costello

1 — When you hear the word successful- what do you think of?

I view success on a broader basis — not just career and work. Certainly doing impactful work is a part of that. So it means being involved in your community, and also living a good balanced life. It means staying healthy, and also having friends and family, and also being able to do work that you think is your own special calling.

You know, I have a lovely family with grown daughters, so I think I’ve been fortunate to be able to have had satisfaction in all those areas. So success is not just about business, it’s about finding, excelling in several different areas. But I will add that it doesn’t all necessarily have to be at the same time!

2 — Tell us about an event or incident in your career that was your “big break”

I think there’s been a few, but if I have to say one big break — that opportunity for me was being a part of the Kauffman Foundation and with the startup of the Kauffman Foundation. It was such a singular experience. Before that I had been an angel investor, and before that I had been a venture backed entrepreneur — but being a part of the Kauffman Foundation at its inception was such a wonderful opportunity — to take that learning and knowledge, and to be able to look at how that could make a difference nationally, and perhaps even globally.

And so, just to give you a little context on this experience with the Kauffman Foundation — I know you know the history, CJ — how Ewing Kauffman passed away and left a billion and a half dollars to form a foundation to back entrepreneurship. This had never been done before. It was so so unique and so unusual that the IRS spent 18 months, and put an army of of agents on it to study whether or not backing entrepreneurs was “socially redeeming” (their words!)

And that was in 1994 when entrepreneurship as we know it really wasn’t well known.

Entrepreneurship was more about main street businesses, and so they were afraid that we were going to be taking nonprofit dollars and somehow using that to enrich [commercial] businesses.

Now we know so much has changed in entrepreneurship. There weren’t even university programs that there weren’t degrees, there weren’t accelerators like we know now, there weren’t angel groups at this level. And so it was really a very new space.

The Ewing Marion Kauffman Foundation is a private, nonpartisan foundation that works with communities in education and entrepreneurship to increase opportunities that allow all people to learn, take risks, and own their success. The Kauffman Foundation is based in Kansas City, Missouri, and uses its $2.6 billion in assets to collaboratively help people be self-sufficient, productive citizens. https://en.wikipedia.org/wiki/Ewing_Marion_Kauffman_Foundation

And so the opportunity to be on that startup team and really have that ability to come together with a great team. And look at how we could impact the whole practice of entrepreneurship was, I would say would would be the break of a lifetime.

Well, the IRS gave us 5 years. They said, well, we’re gonna go ahead and let you operate, and we’ll come back in 5 years and see if in fact, you did do something that was socially redeeming and made a difference. And if you, if you can prove that with outcomes and results, then you know we’ll we’ll let you continue to operate with that as your your philanthropic mission, and now you know 30 years later, there are dozens if not hundreds of foundations focuses on entrepreneurship.

3 -What do you do after you had a bad day?

A bad day for me, is one that drains your energy. You know there’s been so many challenges, and some of them are ones that aren’t going to be tackled with a decision. Sometimes it’s more like a climb up a mountain to come to an answer, which can be draining. So, what I do is get outside, and that’s what takes me into a different place, a different space, as I get outside and enjoy nature.

I’m really fortunate to live in the San Francisco Bay area where there’s a lot of beauty, outside and there’s beautiful hikes … And one of my great pleasures is I have a paddle board, and I’m able to get out on the bay, and you know, paddle out and be out in you know on the water and just you know times like that it’s like all of the problems kind of fade away. And you’re just you know in the moment you’re enjoying the outside, on the paddle board; You have to have your mind engaged when you do it a little bit, and so it helps.

You know, we can look at what’s happening right now, and there are a lot of things that can drain your energy, and things that are out of your control. You know the market is falling apart and that’s impacting how people are looking at investing. We have 113 companies in our portfolio, and some can weather a downturn better than others. And that doesn’t mean that fundamentally they’re not a good business. But you know sometimes it’s the luck of the draw, and so you know it’s those kinds of things where you know you have to remind yourself you you you know when we’re when we’re very can do entrepreneurial people.

We think sometimes we delude ourselves, and thinking we can control a lot of things. But there’s many things we can’t control, and we have to ride with it, right? You just have to go with it and continue to find solutions. and sometimes those solutions, you know, are not obvious. And so those kinds of days are the days, you know, that, I think can be really draining.

4 — What do GenZ’s get really right about life and career?

Well, you know I think it’s really interesting with the Gen Z’s because for a couple of reasons: Actually anytime you have a new generation, and they’re going to question and force all of us to rethink how we do things — the kind of context that we use when we make decisions, how we value and prioritize things.

And I feel very fortunate because I have a number of GenZ people in my world that are that are asking those kinds of questions.

I think they also know that they have a number of challenges ahead. Like sustainability — creating a green world is one of the largest — and I think they’re up for that challenge, you know.

So I’m glad to have to have the GenZ’ers with us, and that they are looking at what kind of world they want to build, and also that they’re they’re what they’re keeping things in balance.

Now, I’m one of the younger Boomer generation. We’ve talked about the negatives of young people as the generations moved up — you know, the millennials, and of course Gen Z. But I actually see a lot of great strength. We already have some some GenZ’s in in our workforce and in our community. And, for the most part I think they’re bringing a new way of looking at how to communicate, and new ways of looking at opportunity and connection. So I like all of that, and I think that we benefit so much when we listen to them.

They’ve had a hard go, you know, as young people in the middle of this pandemic and the fact that they’ve been as technologically proficient as they are, probably saved them. Now they have to be prepared to come in you know to the workforce and be a contributing factor. I’m here for helping them and mentoring them, and I’m here so I can learn from them.

5 — Does Theranos founder Elizabeth Holmes deserve a chance at redemption? Would you give her that chance?

I definitely think that Elizabeth Holmes deserves a chance for redemption. But I would maybe define it differently. You know Elizabeth Holmes may go to prison, for what the court has found that she has done. But I think everybody deserves redemption, the social good that they can bring after making some really significant mistakes.

Now I don’t think that Elizabeth Holmes deserves an opportunity to be in a trusted position in a healthcare field. I think she’s given that up, and I think the the lack of judgment, and the mistakes that she made should cause any investor to determine that she was would not be a leader to create another healthcare company. But there’s a 1,000 different ways to redeem yourself and 1,000 different ways to be a great contributor to the world besides being in a healthcare company.

5–1/2: …. And … the bonus question:

What movie or TV show might best describe your life?

Well, I’ll tell you what I’d have to admit that I am a Trekkie. I’m a Star Trek fan of all the shows — original, The Next Generation, Picard and especially Voyager. And interestingly, I get a lot of lessons and inspiration about mentoring from these shows.

Oftentimes what you would see is that a Captain Jean Luke Picard mentoring his young team, or a Kathryn Janeway (Star Trek Voyager Captain) — mentoring — having some big mistake that was made by (crew member) B’Elanna Torres, and Janeway would be kind about it and use it as a teaching moment.

I found it very helpful to take a television programs when I was in education, to take those kinds of programs, snip them and be able to show, you know, actually show these greater challenges as lessons.

There they are in this, you know, environment working with, you know, intelligent, creative, committed people trying to change their world and create something every week, with this opportunity to overcome some kind of crazy, wild surprise challenge.

And so I look at my life in venture and backing entrepreneurial companies, and growing our own company itself, and you know sometimes think that I’m on the bridge trying to overcome some great challenge and so yeah, that’s my life — on Star Trek on the bridge!

For more 5–1/2 Questions Interviews, see:

5–1/2 Questions” from CJ Cornell is a new series of mini-interviews with leaders in the entrepreneurship and innovation ecosystem around the world. In less than a half-dozen short questions, we’ll try to learn more about each leader, and what makes them successful and unique.

The questions are designed a little like a “Magic Eight Ball” (my GenX colleagues know what this is): A set of questions, posed at random. Plus, at least one question, or half-question, is designed to find out something about their personality that most people might never suspect (I mean expect).

CJ Cornell is a serial entrepreneur, investor, advisor, mentor, author, speaker, and educator. As an entrepreneur, CJ Cornell was a founder of more than a dozen successful startup ventures that collectively attracted over $250 million in private funding; created nearly a thousand new jobs; and launched dozens of innovative consumer, media, and communications products — that have exceeded $3 billion in revenues.

He is the author of the bestsellingThe Age of Metapreneurship — A Journey into the Future of Entrepreneurship.”

And the upcoming “The Startup Brain Trust — A Guidebook for Startups, Entrepreneurs, and the Mentors that Help them Become Great.”

Follow him @cjcornell or visit: www.cjcornell.com

CJ Cornell

Professor of #Entrepreneurship & Digital Media. Serial/Parallel Entrepreneur, Author, Speaker, Mentor, Angel Investor, #VC. Crowdfunding & #Startups Evangelist